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Discovering Me

By: lilythompson



I sat in the Bride's ready room staring at the mirror into the eyes of a stranger. That face, that narrow nose, big round eyes, and wide mouth seemed to belong to someone else. It was the face of someone who was in the middle of the happiest day of her life. It was the face of someone who would, in a few short minutes, be walking down the aisle toward her future husband. I didn't feel like that person.

I stood in the lobby of the church, its doors opened wide before me. Scores of people turned to see a bride dressed beautifully in white as I descended down the aisle to my new husband. All eyes were on me, mine tracked only to the ones that mattered – my best friend's.

I took my first tentative step forward onto the rose colored runner that marked my way to my new husband, my new home, and my new life. As my eyes lingered on Laura's, I felt a familiar flutter in the pit of my stomach and a tingle between my legs.

Memories rushed back like a flood, and I could feel her as if it was happening all over again...

* * * *

The moment her lips touched mine was electrifying. Her lips were soft, gentle as they brushed nervously against mine. Her bright green eyes stayed trained on mine. She pulled back slowly, and I could feel the slight tremble of her hand as she brushed my hair behind my ear then lay to rest around my neck. 

"I've never done this before," I whispered.

"Neither have I," she confessed. 

Hesitantly, I placed my hands on her hips. The room was charged with nerves and sexual tension as she moved toward me, her lips seeking mine. My head swam, dizzy with liquor and lust. Her lips were pressed intently on mine as her tongue flicked into my mouth. Our tongues danced and swirled together. I could feel Laura's mouth crushed against mine, the spice of rum beneath the sweet taste of her as I final broke past my reserve.

My fingers dug into her hips, and I pulled her toward me. I wanted to feel her. I wanted to feel every inch of her pressed against me. Need tugged as I became intoxicated with her scent. I pulled away and met her eyes. Panting and yearning, I stared at her. "I want you."

With that, she lunged at me, our lips meeting as we toppled onto her couch. She propped herself over me as her mouth began to explore my neck. She kissed and nibbled longingly along my jaw bone and over to my earlobes. A moan escaped my lips as my right hand pushed up the hem of her shirt and explored the open territory of her back. "I love the way you taste," she said hungrily. "I want more."

She began kissing over my collar bone and down to the curves of my breast, working around my tank top. My hands ached to explore her as I moved around to the front, under her shirt. My fingers found the lace bra that imprisoned her supple breasts, and I gave her left breast a timid squeeze. My thumb found the nub of her nipple and circled over it. She thrust her chest forward, pressing her breast roughly against my hand encouraging me. I massaged her breast and tweaked her nipple as small gasps escaped her lips.

Her mouth found its way between my breasts as she sucked and nuzzled. Her hot lips charged my skin and I could feel my need growing out of control. My fingers raced over her silken skin as I unbuttoned her shirt. The more of her tender flesh I revealed, the more I yearned. She pulled back and locked eyes with me as I slid her shirt over her shoulders. We both stopped and stared, sensing that we were on the precipice of the point of no return. As she reached back to undo her bra, I deftly pulled my tank top and sports bra over my head. We both sat, topless and staring, taking in the curves the lines, the sheer womanhood in front of the other.

I longed for the supple breast before me, craved to sample more of her, to explore the territory stretched in front of me. I remembered the quickening of my heart and the shallowing of my breath as I demanded and took more. My hands ran over those breasts, leading a hungry mouth over her nipples, over skin so intoxicating in its scent and flavor that I just needed more. I pushed her back, reclined her along the length of the couch as I reveled in my lust for her.

We tumbled, somehow, into an unexplored, unknown, unyielding passion as we continued to undress each other, pulling at hindering clothes and tore away at inhibitions. It was as I lay on her, sweat-slicked and ready that I felt myself fly free. I leaned into her, nipping at her lip, tasting, savoring, as I dipped into her. Laura's moan filled my ears arousing me to new heights as I pushing into her with a firm and steady rhythm. Her hands found my breasts, teasing my nipples to peaks. 

I could feel her hips grinding into my hand, edging unhurriedly toward climax, my excitement mounting steadily with hers. She gave my teat a spirited squeeze as she shifted her weight and threw my balance sending me onto my back and her on top. Her mouth replaced her hand as she send wave after wave of shocks through my body, my hips arching toward her. My mound brushed against hers, desperate yearning rolling through me as we rocked against each other, arousing each other, spurring each other on. She continued to suckle my breast, her hands caressing my stomach and hips, grasping for some semblance of control.

Laura's mouth followed her hands, nipping down my chest, her teeth scraping along my ribs, my stomach, and my hip. Her warm breath delivered ripples over my body. I began to tense in anticipation, yearning for that mouth to find me; waiting for it to find me wet, frenzied, and wanting more. She hovered, poised above my mound and looked up into my eyes. With a slow smile, she dipped her head down, keeping her eyes locked onto mine. A shiver rolled up my spine as I felt her hot breath spread over my lips. Tentatively, she brushed her tongue against my clit, and my head snapped back. 

I moaned her name, "Laura," and she continued with renewed energy. She began licking long lapping strokes over my clit. My climax built with each contact. My hips writhed beneath her mouth as she increased her pace and flicked her tongue. I closed my eyes and could feel each wave of pleasure crash over me. As her mouth explored my most intimate parts, her fingers touched my lips and sent shivers up my spine. She lifted her head and looked into my eyes as she pushed a finger into me. "God, yes," I groaned. 

My control was breaking as she continued her assault on me with her fingers and her tongue. My body tensed and my hands grabbed at the couch cushion beneath me as I could feel the warm glow of climax take over. As I pushed my hips up to meet her quickened fingers, I called out, "Laura, Laura, oh God." With that, she moved up and crushed her mouth to mine in a hot, wet kiss as she plunged her fingers deep inside me, holding them steady with her thumb circling my clit in time to my pulsing climax. Our kiss drowned out my moans as my hips ground against her hand and my orgasm steadily slowed.

* * * *

I blinked, once, twice.

Discovering Mistress Sarah's World



Chapter 1: Meeting Mistress Sarah

Joe's heart pounded fiercely as he stood at the door to his Mistress's house. He did not expect to be so nervous at his first meeting with her. After all he had known her for over a year. Mistress Sarah had been gracious enough to allow him into her world. He was fortunate to fall under the control of such a beautiful dominant woman. She had a gift for quenching his strong submissive desires. She had spent the past year molding him into an obedient and submissive slave through the use of e-mail, texts, and online chat sessions. At the insistence of Mistress Sarah, the time had finally come for a face-to-face meeting. 

Obediently Joe traveled by plane to her town in North Carolina He was somewhat calm all the way up until the point where he stood in front of her door. That's when suddenly his knees grew week and his heart pounded in his chest. He was excited yet nervous to meet her in person. He was about to knock when suddenly his cell phone started to vibrate in his pocket. 

'What timing,' Joe said out loud as he pulled his phone out, wondering who would be calling him. He was surprised to see that it was Mistress Sarah. His communication with her had always been electronic. He had never heard her voice before. He answered the call.

"Hello Mistress Sarah." The words seemed so natural to him, even though his voice wavered with nervousness.

Mistress Sarah's voice was a sharp contrast to his. Confident and bold she stated, "Hello pet. It's so nice to see that you are on time." Then she asked, "Are you ready to completely submit to me?"

Joe answered,"yes Mistress. I am very excited to submit to you."

"Good Kitty, then you may come in. You will go directly to the center of the living room and strip naked. There will be a bag on the couch. Put all your items into the bag. Be a good girl and fold your clothes neatly before putting them in the bag, okay pretty Josie."

"Yes Mistress," replied Joe. 

Joe adjusted his pants to accommodate his growing cock. Mistress Sarah's sexy and commanding voice instantly aroused Joe. Her reference to him as a pretty girl excited him. Mistress Sarah preferred girls over boys. She had made it clear to Joe early on that the only boys she played with were femmed up pretty boys. Mistress Sarah knew how to keep Joe in a constant state of arousal. That was her gift and it was a powerful gift that allowed her to seduce Joe into a feminized state simply to please her. Overtime she had conditioned him to be excited about being feminized. She even gave him a feminine pet name, Kitty, and referred to him as Josie instead of Joe.

Mistress Sarah continued her instructions. "Once you are completely naked you will get down on your hands and knees and crawl over to the stairs. At the foot of the stairs you will get into a worship position. You will kneel facing the stairs. You will stretch your arms straight in front of you, bend forward and place your palms flat on the ground. You will touch your nose to the ground. That's how I want to see you Josie -- naked, kneeling, palms and nose pressed against the floor, ready for worship. Understand pet?"

"Yes Mistress." Joe's cock was completely hard. Her direct commands had already put him into a submissive state of mind.

"One more thing pretty Kitten. You will not look-up, speak, or move, until I give you permission to do so, you will be quiet as a little kitty, and you will not be hard. Got it!"

"Yes, Mistress," replied Joe, uncertain that he could obey the last order. He was already very excited and aroused. He could not imagine how he could calm himself down. Resisting his Mistress was not an option and so he just had to figure out a way to make it happen.

"Good girl. Get to work." Mistress Sarah hung up.

Joe took a deep breath and quietly entered the house. The house was dark and silent. He slowly tip-toed into the living room, trying to remember all his orders. A brown fur couch caught Joe's attention immediately. He chuckled to himself, knowing the fur was one of Mistress Sarah's favorite indulgences. An image formed in his mind of her naked and rubbing her body over the fur, enjoying the softness tickling her nipples and pussy. Joe felt his cock twitch in his pants.

Joe moved to the center of the room and slowly and quietly peeled off his clothes. He felt a bit silly and awkward stripping in the middle of a strange living room. He wondered if anybody was watching.

The last thing he removed was his pink panties. Mistress Sarah preferred femmed up boys and so panties had become a regular part of his wardrobe. He paused for a moment, wondering if anyone was watching. He paused as if to show off his pretty panties. This excited him. Then he slowly peeled them off. In his naked state, he felt completely vulnerable and submissive and this caused his cock to throb. 

Joe glanced at the stairway to the right of the living room and remembered his orders. After placing his neatly folded clothes into the trash bag on the couch, he got down on his hands and knees and crawled to the stairs and got into his worship position. He waited patiently for Mistress Sarah's arrival. 

Mistress Sarah did not make him wait long. She savored the view of her slave kneeling at the bottom of the stairs. Her pussy tingled at the sight. She wanted to race down the steps and quickly take control of her slave but she knew that a slow descent would be more suspenseful and tantalizing to her slave. She liked to play games like this with Joe.

Slowly and deliberately Mistress Sarah walked down the steps, knowing that her slave was intently listening to each step and knowing that the closer she moved to him, the faster his heart beat and the more excited he became. When she was just above him, she spoke.

"Mmmm.. Now that's the way I like my slaves. This is such a perfect way for you to greet me for the first time, don't you think slut?"

"Yes Mistress," replied Joe. No other words seemed appropriate. He remained quiet.

"Look up at me slave," ordered Mistress Sarah in a quick firm tone.

Joe quickly looked up and took in the wonderful sight. She was wearing a black mini vinyl dress and black heels. That was it. Vinyl was his weakness and she knew it. There was something incredibly sexy and powerful about the tight, dark and shiny fabric. His will power completely drained the instant he saw Mistress Sarah standing above him in the vinyl dress and heels. His mind and body surrendered to her control.

With her standing directly above him on the steps, he could clearly see her shaven pussy. He had dreamed about worshipping her pussy over and over again. In the virtual world, Mistress Sarah had ordered him to lick her pussy many times. Now the real thing dangled above him like succulent fruit. His mind drooled at the sight.

Joe's eyes slowly worked their way up her tight body. Never before had he seen such perfect mounds of cleavage. The dress held her tits tightly, presenting them like a delicious dish. Joe was dying to see what was under the wrapper. Finally his eyes settled on her glamorous face. Her glistening red lips looked delicious. Her eyes brows curved perfectly overtop her deep black eyelashes. A hint of green eye shadow brought her beautiful green eyes. She looked so perfect. Joe guessed that her other slave, Julie did her make-up. He hoped he would get to meet Julie later.

"You look amazing Mistress," complimented Joe.

"I know pet. That is a perfect response from you," said Mistress Sarah. Joe was pleased of her approval. "You may worship my toes now."

Mistress Sarah held onto the stair rail and lowered her foot down to Joe's lips. He eagerly licked and kissed her freshly painted toes through her open toed shoe. Joe's soft wet tongue sent chills through Mistress Sarah. His obedience energized and excited her. She could feel the dampness in her pussy grow into pure wetness.

"Good girl," she complimented as he worshipped her foot. Then she teased, "Treat each toe like its own little sex organ pet. Give them lots of attention with your tongue and lips."

Joe enjoyed her direct orders. He drifted deeper into subspace. When Mistress Sarah was satisfied that he had given each and every toe enough attention, she lowered her other foot for worship. Joe was thrilled to obey. He felt completely submissive and this excited him more than ever. All he cared about was pleasing his Mistress. 

Joe's lips and tongue on her toes was quite relaxing. However, Mistress Sarah was not in a mood for relaxation. She wanted to tease and play with her pet. She pulled her foot away and ordered Joe to turn around. Joe obeyed and waited on his hands and knees. He felt the tip of her shoe trace his ass cheeks and then slide gently into his ass crack. 

"Cute little ass, slut," said Mistress Sarah. Then she gave a little tap on his ass with her foot and ordered, "Crawl over to the living room pet."

Chapter 2: Mistress Inspects Her Property

Joe crawled back to the center of the living room. Mistress Sarah ordered, "Stand-up. I want to inspect my property."

Joe stood up. At 6 foot 2 inches he was much taller than Mistress Sarah but his size was no threat to her. She had all the control. She had tamed him into a pretty and obedient kitty. Mistress Sarah placed a finger on the center of his chest. Then she slowly walked around him, her finger tracing his body. 

"Mmmm. Such nice property," she whispered.

When she was behind Joe she placed the palms of her hands on the back of his shoulders and gently slid them down his back. This sent chills through Joe's body. Her hands traced up and down his arms and gently squeezed his muscular biceps. 

"My property," she whispered into his ear. "My kitty."

Joe's cock throbbed. He was happy and excited to be owned. He liked the feeling of being her slave. Mistress Sarah hugged him tightly from behind. She whispered to Joe, "Say it Josie. Tell me whose property you are."

"I am Mistress Sarah's property. I belong to you."

Mistress Sarah kissed Joe's cheek. Her lips were wet and felt delicious against his skin. "Yes, you are mine," she said firmly. Joe could sense lust in her tone. He knew her pussy was dripping and this excited him.

Mistress Sarah's hands dropped down to his cock. She squeezed his hard cock and enjoyed the smoothness of his balls. He was completely shaved per her orders. She held his cock and balls firmly with both hands. Seductively she said, "hmmmm. Kitty's got a swollen little clitty. Didn't I say not to be hard," she questioned with disapproval.

Joe blushed at her reference to his cock as a clitty. It was another way for her to reinforce his feminization. She had trained him to always refer to his cock as his clittie in his e-mails. Hearing her say it out loud for the first time was humiliating but exciting for Joe. "Sorry Mistress. I couldn't help it. You're driving me crazy."

"Did you even try," she asked mockingly.

"Yes. Yes, I tried hard."

Mistress Sarah laughed and walked in front of Joe. "Look at me slut," she ordered.

Joe looked into her eyes. She locked eyes with him and said, "Let this be a lesson Josie. I own your clitty. You have no control over it, no matter how hard your try. Understand?" 

Her lips formed a devilish grin. She had clearly proven her point. Joe nodded in agreement. His arousal grew even stronger knowing how much control she had over him.

"Good kitty," she said approvingly. 

Her hands moved up to his nipples and gently teased and played with them. Joe moaned in delight. 

Mistress Sarah noted out loud, "Seems that you have very sensitive nipples Josie. Sensitive nipples, just like a girl." 

Then she pinched his nipples hard startling him and making him gasp. She laughed at his weakness and pinched his nipples hard one more time. The quick sensation was filled with pain and pleasure. Joe enjoyed the strange effect it had on him. He was thrilled at her power; at how she could make him flinch and feel weak in an instant. 

"Mmmm. I love that," cooed Mistress Sarah. 

Then she placed the palms of her hand on each side of his chest. She enjoyed the hardness of his pecs, even thought that was not her primary intention. Sarah pushed her hands inward, squeezing his chest together. His muscles formed a small amount of cleavage. She observed out loud, "The right bra or corset, will show off your tits nicely pretty Josie."

Mistress Sarah, released her grip and watched with amusement at how his chest muscles instantly sprung back to shape. Then she ordered, "turn around slut and let me see your pretty pussy."

Joe turned so that his ass was to her. She firmly placed her hand on the center of his back and pushed forward and commanded, "bend forward slut. Pull your ass cheeks apart for me."

Joe did as instructed. 

"Wider," demanded Mistress Sarah.

Joe took pleasure in the stretching sensation as he pulled his ass cheeks as far apart as he could. He felt completely submissive and vulnerable on display for his Mistress. Mistress Sarah gently blew into his ass and watched his sphincter muscle quiver at the unexpected sensation.

Mistress Sarah laughed, "See I even control your tight little pussy. Miss May is going to have fun breaking you in."

Joe's cock twitched at the mention of Miss May. She was one of Mistress Sarah's friends and lovers. Miss May had teased Joe online many times and continually talked of pegging him hard in his ass. Over the past few months Mistress Sarah and Miss May had transformed Joe into such a horny slut that he was looking forward to the moment when his 'pegging' would finally happen.

His fantasy thoughts of Miss May were interrupted by the jingle of a bell. "I have something special for my kitty," said Mistress Sarah as she walked in front of Joe. In her hands was a pink ribbon with a small bell tied in the center. She had Joe stand up and then she tied the ribbon around his neck.

Mistress Sarah smiled at the bell dangling from his neck and said, "Yes, a cute little bell for my pretty little kitty so that I can hear you prancing around. Mmm...and the pink ribbon looks so pretty on my delicate Josie."

She had Joe get down on his knees and walk around the room. "Come on kitty, prance around. Let me hear that bell jingle."

Joe crawled around the room, making sure the ribbon swayed so that the bell would jingle. He was delighted to hear Mistress Sarah giggle and clap with approval. Her pleasure and happiness is what he strived for and what excited him. She patted him on the head and complimented, "Good kitty...Good kitty."

Joe wished he could purr like a real kitten to show his happiness. Instead he just whispered, "purrr....purrrr."

Mistress leaned down and kissed him on the check. "That's what I like to hear kitty." Then she giggled and said, "but that was much too deep for my pretty girl kitty. Let me hear a higher pitched purr."

Joe purred a higher pitch. He thought it sounded silly and he blushed at the silliness but Mistress Sarah was delighted. "That's better sweetie. You really are my pretty kitty aren't you?"

Next Mistress Sarah retrieved her cat-o-nine tails whip and made Joe kneel on the couch, facing the back of the couch so that his ass was exposed to her. His cock rubbed against the furry fabric of the couch. The soft fabric felt amazing against his sensitive cock.

"Enjoying the fur," commented Mistress Sarah.

"Yes. It feels so good. I could hump your couch," joked Joe.

"Maybe I'll let you do that later slut, if you're good." 

Mistress walked behind Joe. The whip in her hands was named after its shape. Nine knotted strands of cotton cord dangled from the handle. Mistress Sarah lightly slapped the soles of his feet with the cat-o-nine tails.. 

It's time for a spanking," announced Mistress Sarah. "Kitty's been a little naughty, haven't you?"

Joe just knew to answer yes. Chills filled his body as she slowly traced the whip up his legs, around his ass, and up his back. His body tensed slightly, wondering when the spanking would start. Mistress teased him like this for a minute or two. Before he could get too excited Mistress brought the whip back and gave him a quick slap on the ass. This startled Joe and his whole body flinched. As he flinched his cock pushed into the furry couch and he was rewarded with a burst of soft pleasure.

Mistress Sarah laughed at his weakness. She whipped his ass again and again, harder and harder each time. Joe did not expect such harshness. He tried to be brave but he finally cried out, "Ow! That hurts Mistress."

"Of course it does," exclaimed Mistress while whipping him two more times. "I want you to take pain for me slut. Will you do that for me?"

Joe wanted to say no, but he knew better. "Yes," he responded.

"Then ask me to whip you slave."

"Please whip me Mistress," asked Joe in a wavering voiced.

Mistress Sarah whipped his ass again, taking pleasure in the bright red marks left from the chords. The she shouted, "Not good enough slave! Tell me you want to be whipped hard."

Joe tensed his body and responded, "Please whip me hard Mistress."

"Much better slave," replied Mistress Sarah. Then she gave him three hard whips across his ass and the back of his legs.

Joe cringed in pain. Then he felt the whip being lightly dragged over his hot skin. It felt soothing. Mistress Sarah kissed him on the cheek and whispered, "Good girl. It's all over now Josie. I am proud of you being so brave."

"Thank you," replied Joe, happy to get her approval.

Mistress walked behind the couch so that she was facing Joe. Her finger reached beneath her latex dress and dipped into her dripping pussy. She moaned and said, "Your whipping made me very hot Josie kitty. Your pain is my pleasure sweetie." Then Mistress Sarah placed her glistening finger up to Joe's lips and quietly said, "Taste how excited you made me pet."

Joe eagerly took her fingers into his mouth and tasted her reward. His cock had grown slightly flaccid during the whipping, but now suddenly it was hard and throbbing. 

Mistress Sarah had Joe stand up and then she reached down and squeezed his hard cock. Her fingers teased the tip of his cock and rubbed over the tiny hole until they were covered in pre-cum. Once again she moved her finger to his lips. Joe's mouth was already accepting her cum covered fingers when she said, "Seems like somebody else is a little excited too. Lick it all up pretty Josie. I know how much slutty girls like you love cum."

Being fed his own cum and called a pretty girl, had a profound effect on Joe's mental state. It was clear evidence of her power over him. Joe did not fully understand this strange pleasure but he liked it and could not resist it. Mistress squeezed more cum onto her fingers and brought them to his lips again. "Good girl," she complimented as he licked up the stickiness. She repeated this over and over again, making Joe lick up his cum. The more cum he licked, the deeper he fell into submission and the more he mentally transformed into Mistress Sarah's pretty girl.

Chapter 3: The Feminization Begins

Mistress Sarah took a step back and admired her slave's nakedness. Then she said, "Well, I have a blank pallet to work with. Are you ready to be transformed into a beautiful girl Josie?"

Joe blushed. He knew that's what Mistress Sarah wanted. That's what this weekend was all about. She had already partially feminized him as her online slave. It started as a fun game for Joe. He played along just to continue the online fun with Mistress Sarah. He never expected it to get too far but her sex appeal and seductive words were too irresistible for Joe and so he found himself feminizing himself more and more simply to please his Mistress. 

The more he pleased her, the more rewards he received. After wearing panties to work, he was rewarded with her sexy picture, which he gladly worshipped every morning.. Stockings earned him an online role playing session with her. One night she got him so horny and sexed up for her, that he agreed to lick up his own cum. The next day he was ashamed to think about what he did, but he was also horned up at how hot the session was and at how submissive and slutty she made him feel. Soon, licking up his cum after an orgasm became a regular routine for Joe.




Discovering Mistress Sarah's World Pt. 02



Chapter 4 : Introducing Miss May!

Miss May's arrival seemed sudden and quick to Joe. He heard the door close downstairs. Then there was the sound of somebody running up the steps. The bedroom door flung open and before Joe could look up to see anything, he heard an excited voice exclaim, "kitty-kat!"

"I think someone is excited to see you," laughed Mistress Sarah.

Miss May quickly approached the bed. "Stand up kitty-kat and let me see you."

Mistress Sarah had put Joe into a calm and placid state of mind. It took him a few seconds to adjust to the rush of excitement that had entered the room. He slowly rose from the bed. Miss May instantly hugged him.

Joe enjoyed the warm welcome. For a moment he felt like he was hanging out with an old friend. However, when her embrace ended and he was aware that she was fully clothed and he was standing before her in a teddy and stockings and sporting a hard cock, he reverted back into submissiveness. He wanted to come out with confident and suave greeting, but instead he shyly said, "hi," to Miss May while his cheeks blushed slightly and his eyes darted downward. 

Miss May stood back and took in the sight. "Look at you kitty. You're so pretty in your pink teddy and stockings. Such a cute little kitty-kat bell too." Miss May jingled the bell around his neck with her fingers. Then she looked down at his hard cock and said, "....and your clitty is so big. Excited to see me are, you?"

Miss May reached out and firmly squeezed his cock a few times. It was a welcome sensation that reverberated though his entire body. Before Joe could respond, she ordered, "Turn around kitty-kat. Let me see that ass of yours."

Ever since he met Miss May online, she had talked about pegging him in this ass. Joe had never experienced this before but over the past few months, Miss May had nurtured a strong desire within Joe to be taken by her strap-on and so it was thrill for him to turn and show her his ass. 

Joe felt a push on the center of his back. "Bend over slave," ordered Miss May. 

Joe's hands braced on the bed as he fell forward so that he was bent forward, with his ass on display. Mistress Sarah sat to the side of him on the bed and watched with amusement. Miss May kicked her foot against the inside's of his ankles and ordered, "Spread 'em slut."

Miss May pulled the fabric of the teddy to the side and gazed at his ass. "Yummy. Such a tight pussy Josie. I can't wait to peg you bitch. I bought a nice new strap-on just for you kitty-kat."

Joe's ass was tingling and ready for her strap-on. This was a moment he dreamed about for months. Joe begged, "Please fuck me with it Miss May!" 

Mistress Sarah interjected, "Calm down you two. We've got some more work to do on you Josie. You want to be nice and pretty for your first fuck date don't you?"

"Yes Mistress."

"Of course you do slut." Mistress Sarah turned her attention to May. "May, there's a sexy outfit for you in the other room. Hurry and put it on so you can help me transform Josie."

"You got it Miss S," replied May happily. Then she quickly headed off to get dressed.

Joe endured more teasing of his cock until Miss May returned. Miss May entered the room dressed in a black latex mini skirt, latex halter top, and high heels. A thin latex collar wrapped around her neck. Her hair was pulled back into a tight bun. One glance at her dominant and sexy look and Joe felt himself becoming weaker and more submissive.

"This is not fair," commented Joe in a light hearted tone. "You know how excited I get from seeing you in latex. You both look amazing. I don't think I can handle two beautiful dominant women at one time."

Mistress Sarah gave Joe's cock a hard squeeze and said, "That's the point slut."

May confidently walked over to the bed. "Thank you for the compliment kitty-kat. This outfit is very sexy. A good choice Miss Sarah. Thank you."

Mistress Sarah stood up and walked toward May. Talking to Joe she said, "She does look hot." 

Then Mistress Sarah leaned in and gave May a kiss. It started as a simple peck on the lips but quickly turned into a deep tongue kiss. Each of their hands rubbed each others bodies as they kissed.

Joe sat up on the bed and watched his two Mistresses. He loved what he saw. He was completely enthralled in the action. He could not help but stroke his cock as he watched the two beautiful dominant women kiss and fondle each other in front of him.

Mistress Sarah slid behind May. Both girls were facing Joe. May's skirt was so short it barely covered her pussy. In one smooth motion, Mistress Sarah pushed up the bottom of May's skirt and dipped her fingers into her pussy. 

Joe rubbed his cock through the teddy and excitedly watched Mistress Sarah's fingers slowly move in and out of Miss May. He saw Miss May's head lean back against Mistress Sarah's shoulder and her eyes close from the pleasure. He could see lust in Mistress Sarah's eyes. All this erotic imagery fueled Joe's arousal and desire to want more. He was glad to be where he was. 

While Mistress Sarah slowly pleasured Miss May, she looked at Joe and said, "This is all part of my plan Josie. I am letting you into my world. My world is full of sex, kinkiness, and excitement. It's what you want isn't it? It's what you dream about. The more you obey me and the more you let the pretty girl in you surface......the more I will let you into my world."

Mistress Sarah was quite the sales person because at that moment all Joe cared about was being in her world. He wanted it bad and he let Mistress Sarah know. Almost begging Joe said, "I want to be in your world. This is where I want to be Mistress."

"Good pet. Tell me what you need to do."

"I need to obey you and bring out the pretty girl in me."

"Yes. Now tell me you will do it."

"I will obey you and I will bring out the pretty girl in me."

"Say it again Josie."

Joe repeated, "I will obey you and I will bring out the pretty girl in me."

By now Mistress Sarah's fingers were glistening with May's juices and May was moaning softly from the slow continuous teasing of her pussy. Mistress Sarah brought her fingers to May's lips. Her seductive eyes never left Joe's. They captivated and controlled Joe. The second she looked down at Miss May, Joe's eyes followed. His cock throbbed in his hand at the sight of Miss May licking her own juices off Mistress Sarah's fingers.

"Good girl," whispered Mistress Sarah into May's ear. Then she gave May a kiss on the lips. Mistress Sarah looked at Joe and said, "The pretty girl is already here isn't she? You are pretty Josie right now aren't you?"

"Yes," replied Joe. 

"That's right Josie. We just need to give you a make-over and teach you to be prim and proper. There's quite a bit of work to do on you. Are you ready?"

"Yes Mistress. I am ready. I want to be a pretty girl for you."

"Good. Let's start with your legs. May, go get the Nair out of the closet," ordered Mistress Sarah.

While May left to get the hair removal cream Joe panicked, "I thought we weren't going to do anything permanent."

"Permanent," questioned Mistress. "There's nothing permanent about hair removal. It grows back."

Mistress Sarah savored the hesitant and concerned look on her pet's face. This was the game she loved to play. She loved to tease and toy with her pets. She knew that her beauty and feminine power could persuade a boy to do things he would never imagine doing on his own. This control is what filled her with lust to feminize boys. Her pussy quivered and dampened knowing she was challenging his will and pushing his limits. Mistress had already decided that his legs would be shaved but she let him think he had a say. She liked to tease him this way and get him to convince himself that that it was o.k.

"But what about the time it takes to grow back," protested Joe, already sensing his argument was in vain. 

Miss May returned to the room. She had heard the whole conversation from the hallway. She quickly chimed in, "Don't be such a 'wuss' kitty-kat. Swimmers shave their legs. Even body builders do."

Then Mistress Sarah threw in a zinger. "Besides, you don't want the hair on your legs to show through your stockings when were out in public, do you? Then everyone would know you were a sissy."

Joe's heart skipped a beat. He questioned with alarm, "In public?"

Mistress Sarah replied sweetly, "Why yes my pretty little Josie. I've got to show off my new princess slave to all the girls. You didn't think I'd make you come all the way down here and then hide you away, did you?"

"I guess not," replied Joe. He knew that a public appearance in full femme gear was inevitable. It was on his mind the whole trip down. It was just a scary thought at the moment.

Mistress Sarah reassured him, "Don't worry kitty, your big debut is not until tomorrow night and May and I are going to transform you into a pretty girl. When you walk by people are going to look twice. Not because they think you're a guy but because they just saw the cutest, hottest girl in the place."

While the words were still sinking in, Mistress Sarah took Joe's hand and led him into the bathroom. Joe followed with no resistance. He did not have the will or courage to resist. He was completely under her control.

Chapter 5: The Sissy Phase

In the bathroom, Mistress Sarah and Miss May stripped Joe out of his teddy and stockings and had him stand in the center of the bath tub. The garter belt was left on as a reminder of his femme state. Mistress Sarah supervised as Miss May spread the hair removal cream all over Joe's legs. 

As May covered his legs she commented, "Your legs are going to look so smooth and sexy Josie."

Joe stood in the tub confused at how hard his cock was. He was being emasculated, yet he was aroused and excited. He knew he could not stop what was happening and it excited him. He was also thrilled to be in the presence of two beautiful dominant women. Their shiny black latex outfits looked amazing against their bronzed skin and the outfits left little to the imagination. Joe had a perfect view of Miss May's firm tits while she was leaning over, covering his legs with the Nair. All the sexuality around him was a fantasy come true. 

While the cream tingled on his legs and worked it's magic, May tugged on his cock and played with it, keeping Joe aroused. Then she washed away the cream and Joe was left standing with hairless legs. Miss May then moved to his chest. "We are going to be showing off your cleavage tomorrow Josie. We can't have any hair here."

She quickly covered his chest and stomach with the cream. Joe just stood and let it happen. When his hair was removed, Mistress Sarah and May massaged a Cherry Blossom scented lotion all over his body, taking every opportunity to tease his cock and play with his nipples. Joe enjoyed the attention and soon his knees were weak, his breathes were deep, and he was on the brink of orgasm.

The girls giggled, knowing how aroused they made him. May leaned in and licked his earlobe and whispered seductively, "mmm. See how fun it is being one of the girls. You smell like a pretty cherry Josie, and your body is so smooth and girly now. I can't wait to rub my naked body all of yours."

Then Mistress Sarah scooped up some of the cum that was leaking out of his hard cock and put it up to his lips and said, "Have a taste of Joe's cum Josie." 

Joe obediently sucked his cream off her fingers. The way Mistress Sarah presented it to him as 'Joe's' cum was mind blowing. It made him feel slutty and like he really was Josie."

"Good girl," replied Mistress Sarah. "I'm so proud of you," she added like a caring mother.

With his smooth chest and legs, the girls could not wait to dress up Joe again. He was led back to the bedroom. Mistress Sarah pulled a large white box from under the bed and placed it on top of the bed. 

"This is special sissy lingerie for you Josie. I know you want to be transformed into a pretty girl, but tonight you will be just a sissy. This is a necessary step in your training pet. You need to experience all the moments of becoming a sissy so that it will shape who you are and prepare you for the next exciting step of being completely feminized."

While Mistress Sarah unpacked the box, May squeezed Joe's cock and said, "That's right sissy boy. This cock will always be a reminder that you are not good enough to be a girl." She reached up and rubbed her hand across the stubble on his face. "and we purposely left your face unshaven today so that everyone will know that you are a boy dressed as a girl."

As Mistress Sarah laid each item on the bed, Joe could see that it was truly sissy lingerie. There was lots of shiny satin, frilly fabric, and silky bows. Joe imagined the silk would feel incredible against his smooth skin. 

It felt surreal to Joe to be standing there completely aroused and submissive while the girls dressed him as a sissy. He was dressed in pink frilly satin panties, white stockings, and a white lacey garter belt. The white stockings had large silk bows at the top.

May admired his legs. The stocking enhanced his smooth well toned and muscular legs. She rubbed her hands along the stockings and commented, "Josie, your legs look so smooth and sexy in those stockings. You put other girls to shame."

Joe blushed but was actually proud of the compliment. He looked down at his legs and agreed with Miss May. They looked very sexy. "Thank you Miss May," he replied.

Next Mistress Sarah approached him with pink satin bra in her hands. In an excited voice she said, "Here's your first bra sissy. Put your arms out princess and I'll help you put it on."

Like a puppet, Joe obeyed. Butterflies filled his stomach and his cock twitched as Mistress Sarah strapped secured the bra. He felt completely emasculated and feminized with the bra on. He was nervous and excited from crossing over this threshold into the feminine world. The tightness of the bra, felt like bondage to Joe. He felt as if he was being locked into the feminine world and pushed deeper under Mistress Sarah and Miss May's control.

"Oh that is so pretty," commented Mistress Sarah as she admired her pet. 

His muscles contrasted beautifully against the pretty delicate fabric. Mistress Sarah's body shivered in excitement to see this strong man dressed so feminine and pretty and to see him so docile and submissive to her. 

"My pretty little slave girl," she said with delight and accomplishment. 

Mistress Sarah reached down and squeezed his cock through the panties and teased it a bit. She wanted to ensure he remained fully aroused and close to orgasm during his feminization. She knew keeping him aroused allowed him to be easily manipulated and trained to be her obedient feminine slave. 

Mistress Sarah continued to play with his cock and asked Miss May, "Why don't you get the special sissy dress for our slave May."

"My pleasure," responded May. 

Miss May pulled a large satin dress from the closet and displayed it for everyone to see. The dress was the most feminine and sissy looking dress that Joe had ever seen. It was made of high quality pink and white bridal satin. A white satin apron with pink ribbons was embroidered on the front of the dress. White shimmery lace trimmed the bottom of the dress and the sleeves. 

May asked, "Isn't this so pretty Josie. You are going to look so adorable in this."

Joe was very aroused and extremely excited to please Mistress Sarah and Miss May. He could not wait to try the dress on. He knew his thoughts and desires at that moment broke all the rules he was taught about being a man but he didn't care. Mistress Sarah had unleashed a new feminine desire in him that he could not hold back. He accepted his new fate to be a sissy and he eagerly slipped into the dress with the help of Miss May.

Miss May pulled the dress down around Joe and straightened the hems, while Mistress Sarah slowly walked around her new dress-up toy and admired 'her.' She commented, "What a lovely sight. You are so pretty and cute Josie. Mistress is very pleased with her sissy. Come look at yourself in the mirror."

Joe walked over to the mirror with Mistress Sarah. As he walked he was aware of many feminine sensations. The tightness of the bra against his chest, the silky stockings rubbing over his legs and stretching against his toes, and the dress rubbing along his thighs and legs as he walked were all wonderful new sensations that reminded him of his feminine state. His arousal grew stronger knowing that Mistress Sarah was purposely bringing out the girl inside him.

Joe never imagined he would be staring at himself in a mirror, dressed as a sissy. He never would have predicted or comprehended how exciting the moment would be. Beneath the pink shiny dress and underneath his satin frilly panties his cock throbbed harder than ever. He wanted to touch it stroke it desperately but he knew that was forbidden. Instead he flexed his PC muscle, causing his cock to pulse against the silky sissy panties. He felt completely submissive dressed as a sissy and surrounded by his two Mistresses who were dressed in tight sexy latex outfits.

Joe gazed into the mirror like a deer in headlights. He thought he looked silly but he knew Mistress Sarah and Miss May were pleased with his look and he knew that their pussies were dripping from his obedience and from his sissy look. This alone, made it worthwhile. He would not want to be caught dead dressed as he was, in front of his friends but in Mistress Sarah's world, he was thrilled, aroused, and excited to experience his sissy state.

Miss May and Mistress Sarah showered him with compliments. "You are so pretty princess," cooed Mistress Sarah.

Miss May added, "Pink is your color sweetie. We're going to have to paint your nails a nice pretty pink to match you dress."

"I have the perfect shade," said Mistress Sarah.

Everything happened so quickly. The girls had Joe sit on stool and each took a hand and went to work. In just a few minutes he had shiny pink finger nails. Miss May added a wig with long straight black hair while Mistress Sarah applied glossy red lipstick to his lips. Mistress Sarah brought a hand mirror up to Joe's face so he could see the results.

Joe had a good amount of razor stubble on his face. The wig and lipstick alone did not create a pretty picture. He simply looked like a man wearing a wig and lipstick. Joe asked, "Can I shave Mistress? Will you put more make-up on me so I look more like a girl?"

Miss May giggled at his requests. Mistress Sarah responded, "Josie, it's good that you notice these things sweetie. Wanting to make your face pretty and girly shows me how well you are progressing in your training and moving along your journey to girlhood. I am so proud of you for that but we will save the make-up and shaving for tomorrow. Remember you are sissy tonight and this is what sissies look like. You make a perfect sissy sweetie." 

"Yes Mistress," replied Joe. 

Miss May commented, "You are quite a sissy boy Josie and tonight you are going to be my little bitch aren't you? Tell me what sissy bitch you are going to be for me."

Joe knew what she wanted to hear. "I'm going to be your sissy bitch tonight Miss May. I'm going to suck your strap-on and I'm going to let you fuck me with it."

Miss May laughed and questioned his last words, "let me fuck you? There's not 'let' sissy bitch. I AM going to fuck you. You have no choice. Now say it again slut. Tell me you are going to be fucked."

Miss May's words were stern and unforgiving, but Joe loved it. It pushed him further into subspace. Joe replied, "I am your sissy bitch and I am going to be fucked by you tonight."

"That's my slut," laughed Miss May. "Now show me your sissy panties. Lift up that cute dress of yours and show me your pretty panties."




Discovering Mistress Sarah's World Pt. 02



Joe did as instructed. Both Mistress Sarah and Miss May slapped his ass and commented on how cute his ass looked in the panties. He was made to bend forward. Then he felt his panties being pulled down to his thighs. 

Miss May said, "This should help keep your mind on what's going to happen later tonight." 

Joe felt something firm poke at the entrance to his ass. Slowly Miss May pushed a lube covered butt plug into his ass. The wide bottom spread his asshole and filled his insides. Joe moaned in pleasure from the fullness. His cock twitched and dripped creamy cum from the carnal pleasure. Before Miss May pulled up his panties, she squeezed his cock a few times, causing Joe to shudder in pleasure. Warm cum oozed out onto her fingers. Miss May spread the stickiness all over Joe's cock and balls. 

Somebody's sissy clitty is all wet, isn't it," questioned Miss May.

"Yes Mistress," moaned Joe.

Miss May moved her fingers up to Joe's mouth and said, "You know what to do."

One-by-one Miss May pushed her fingers into Joe's mouth. Joe licked his cum off her fingers. 

Mistress Sarah stood to the side, dipping her own fingers into her pussy. Watching Miss May push the plug into Joe's ass increased her arousal. Now as she watched her pet lick his cum of May's fingers she said, "Good girl, Josie. Lick up all that boy cum. "

When Miss May's fingers were all clean, Mistress Sarah announced, "Now it's your turn to make us pretty Josie."

Chapter 6: Girl Fun

The girls had Joe undress them. He happily obeyed, enjoying the sight of Miss May's firm titties popping out of the tight latex top as he pulled it up. He was thrilled to kneel before her and pull down her skirt, revealing her swollen pussy. He was equally thrilled to peel the tight dress off Mistress Sarah. He felt like he was unwrapping the sexiest gift in the world.

The girls allowed a few moments of body worship. He gently licked and sucked their nipples and he spent a few minutes lapping at their pussies while they kissed and played with each other. Joe was in heaven being surrounded by such beauty and sex. Miss May and Mistress Sarah were also in sexual bliss from having their sissy slave kneeling and pleasuring them while they took pleasure in each others sensual kisses and warm bodies.

It took quite a bit of will-power but Mistress Sarah was able to stop things before it got too steamy. She wanted to have more fun in the shower with Miss May and she thought this would also be a great tease for her kitty. Mistress Sarah handed Joe a small plastic basket that was filled with various sex toys and vibrators.

"Follow us kitty," giggled Mistress Sarah.

Joe followed the girls into the bathroom. Mistress Sarah looked at him in deep thought and said, "Hmmm kitty, I want you to be kneeling by the tub while May and I wash each other but I don't want you to ruin your pretty sissy dress. May, why don't you help him get it off."

Miss May helped Joe out of the dress and hung it on a hanger for use later. Joe was left in his bra, pink frilly panties, garter, and white lacy stockings. Miss May lightly pulled on the large satin bows at the top of the stockings, admiring them. "These are so cute and pretty Josie. They really bring out the sissy in you. It's so sexy. I love it!"

"Thank you," said Joe enjoying the attention and compliment.

Mistress Sarah had turned on the shower and stepped in. She yelled to May, "Pick out a toy May and come on in. I want to enjoy your sexy body."

Miss May had Joe kneel by the tub and hold the basket of sex toys. She sorted through the toys and picked out a pink vibrator. "This will feel good in my pussy," she said happily and then disappeared behind the shower curtain.

Both girls were already wet and aroused from dominating and sissifying Joe and so their steamy shower got even steamier in seconds. Mistress Sarah devoured May the second she stepped into the warm stream of water. She pushed May against the wall and pressed her naked body against May's. Their tits pressed together in warm softness. Mistress Sarah passionately pushed her soft tongue into May's mouth and they enjoyed a steamy kiss as the warm water poured around them. Then she took the pink vibrator from May and turned it on and started teasing May's pussy with it. It was exhilarating for Mistress Sarah to have one of her pets pressed beneath her body while another pet was kneeling outside horny and waiting.

In the shower, May's mind relaxed and submitted to Mistress Sarah. Mistress Sarah made it too easy for her to switch from a dominant role with Joe to a submissive state. The vibrations in her pussy quickly brought her to the brink of orgasm. Her whole body was alive with pleasure. 

Kneeling outside the shower, Joe was intently listening to the buzzing vibrator, the sex sounds, and the erotic moans on the other side of the shower curtain. He wished he was in the shower with the girls. Joe reached inside his panties and played with his cock while he listened and imagined what was going on. 

Mistress Sarah pulled the curtain back for a moment to allow Joe a glimpse of the sizzling action. Joe was eye level with Miss May and had a perfect view of Miss May kneeling in the tub with her mouth pressed against Mistress Sarah's pussy. Miss May was the one with the vibrator now and as she orally pleasured Mistress Sarah, she also worked the vibrator into her pussy. Their wet shimmering bodies were a golden prize for Joe.

Joe looked up at Mistress Sarah and was immediately drawn to her eyes. Mistress Sarah purposely locked in on her pet and licked her lips. Seeing him kneeling and dressed as a sissy with his cock in hands sent her over the edge. It was hard for her to not close her eyes and sink into the deep pleasure from May's soft tongue but she wanted to see her Josie. She wanted him to see the lust and pleasure in her eyes while she climaxed. Mistress Sarah pushed May's head into her pulsing mound and moaned at Josie as her boy shook and shivered in pleasure. When her orgasm faded away she blew Joe a soft kiss with her lips and let the shower curtain fall back in place, leaving Joe throbbing and desperate to see more.

It was only a few seconds after the shower curtain fell shut that the pink vibrator was held out for Joe. "Kitty-Kat, give us the small white vibrator," ordered Miss May.

Joe quickly pulled the vibrator from his basket of toys and exchanged it for the wet pink one. As Miss May's hand disappeared into the shower Mistress Sarah ordered Joe to clean the pink one with his tongue.

"Lick off our sweet juices sissy slut. I want you to suck on it for a bit too Josie. Sissy's must learn to be good a sucking things. Then you can clean it in the sink with soap and water."

"Yes Mistress," replied Joe eager to please. 

Willingly he licked up and down the sides of the vibrator, delighted to know it was in both their pussies. Then he pushed it into his mouth and sucked on it. The curtain opened for a second and both girls giggled at the sight.

"Good girl," complimented Mistress Sarah.

"Push it in and out sissy. Suck it like a cock," ordered Miss May.

Joe obeyed. His arousal heightened from the humiliating order. 

"Mmmm, So nice. You're a good cock sucking sissy," added May. Then the shower curtain closed again.

Joe heard more giggles, moans, and humming as the girls played with each other in the shower. As soon as he finished cleaning the vibrator Mistress Sarah shouted over the curtain, "Sissy, get my strap-on ready. Miss May needs a good fucking."

"Yes Mistress", replied Joe.

"Hurry princess. Put a nice cock in that harness."

Joe found the harness and a cock shaped dildo in the basket. Quickly he secured the dildo into the harness. 

"It's ready Mistress," announced Joe.

"Lube it up really good slut. Hurry!"

The shower curtain opened while he was lubing up the cock. Miss May was facing the back wall in the tub and was bent forward with her hands pressed against the wall and her tight round ass pushed out toward Mistress Sarah. Mistress Sarah tossed the used vibrator at Joe and grabbed the strap-on from his hands. 

"Thanks slut," she said. "You know what to do with the vibrator."

The curtain closed but the hot image of Miss May's ass' sticking out for Mistress was seared into his mind. Joe stared at the curtain wishing he could see right through it. Slowly he licked the second vibrator with his tongue and listened intently trying to imagine what was happening just a few inches from where he was kneeling.

A quiet moan from Miss May echoed through the small room. "oohhhh. That's feels so good."

"Your ass is so delicious May," cooed Mistress Sarah.

Joe could hear the sounds of Mistress Sarah fucking May at a steady but increasing pace. As the pace quickened Miss May's erotic moans became quicker and louder.

Mistress Sarah spoke to Joe through the curtain. "Hear that Josie....It's what you are going to sound like later tonight. I bet you will scream much louder than May. She's going to make you scream and moan like a prissy little girl. Does that excite you slut?"

"Yes Mistress. My clitty is so hard and swollen right now. I can't wait. I wish she could peg me now."

"Mmm. That's a good bitch. Pull back the curtain and watch sissy," ordered Mistress Sarah.

Joe did not hesitate to obey. He slid the curtain back and watched Mistress Sarah pound her strap-on into Miss May's pussy from behind. The steamy shower water sprayed all over their wet bodies. Joe was too excited to even feel the water splashing onto him. He stroked his cock as he watched, not even realizing he was stroking in rhythm with Mistress Sarah's thrust.

"This is so hot! God I want to cum," begged Joe.

"Oh God, you horny bitch," Miss May moaned at Joe then she pleaded to Mistress Sarah, "Yes, fuck me...oh yes...you feel so good inside of me."

Mistress Sarah was enjoying having both her pets on the verge of orgasm. She had not planned on allowing Josie an orgasm but the moment just seemed right. 

"Do you want to orgasm Josie slut," asked Mistress Sarah.

"Yes! Please," begged Joe, hoping she was not just teasing him.

"Get the cup from the sink," ordered Mistress Sarah, still pounding May.

Eagerly Joe scooped the cup off the sink and got back into position on his knees.

Mistress Sara said to Joe, "You've been such an obedient little bitch for me Josie. You can follow May to an orgasm. I want all your cum in that cup, got it?"

"Yes Mistress. Thank you Mistress," said Joe, thrilled at his chance for release. 

Then Mistress Sarah said to May, "Cum when you are ready pet and once you start cumming, you can give the order to Josie."

Mistress barely finished her sentence when May's body started convulsing with pleasure. She pushed her ass back as Mistress Sarah pushed inward with her strap-on. May's pussy muscles gripped the strap-on and held on for pure pleasure. She moaned loudly and between orgasmic breaths ordered to Joe, "Cum bitch. Cum like a sissy."

May's and Joe's moans echoed through the bathroom as their pleasure erupted like a hot volcano. Sarah pumped May's pussy while Joe pumped his cock and filled the cup with his cum. His orgasm seemed to last forever. When it finally finished, he did what was normally expected. He lifted the cum filled cup to his lips but to his surprise he was stopped.

Mistress Sarah yelled, "Wait slut!"

Joe stopped and looked at his Mistress. She stepped out of the shower, her strap-on bouncing in front of Joe and intimidating him. She mused out loud, "Josie, you are so eager to drink up Joe's cum. You really are a sissy whore aren't you? I like that Josie. I like that you are eager to be my cum drinking slut. Pour some into your palm slut."

Joe tilted the cup and let the warm cum ooze out onto the palm of his hand.

Mistress Sarah thrust her strap-on towards Joe and instructed, "Good girl Josie. Now stroke my cock with it. Rub it all over the tip of my cock. That's it pretty. Get my cock nice and sticky. Make a nice creamy 'cocksicle' Josie."

Joe followed orders, knowing that 'cocksicle' was going to be for him. The order from Mistress came quick and sudden, "Suck it slut. Suck my cum covered cock."

Joe immediately obeyed. He took the cock into his mouth. Mistress slowly pumped just the head in and out of his mouth. Although he just had an orgasm, his cock was hard. What he was doing was so perverse and taboo that it thrilled him. He enjoyed being her fuck toy. Mistress Sarah fucked his mouth and called him her bitch, slut, and cum eating whore. By now Miss May had turned off the shower and joined in on the name calling. All these humiliating things fueled his arousal and made him want to be even sluttier.

He desire to be slutty was easily met. Mistress Sarah pulled her cock away and ordered, "put some of that cum onto your lips. Make them nice and glossy for me."

Joe dipped his fingers into the cum and rubbed them around his lips. May was not satisfied. "More cum on those lips bitch," she yelled.

Joe quickly complied, rubbing cum onto his lips until they were dripping. Then Mistress Sarah ordered him to pull out his butt plug. "Dip it in your cum whore. I want it dripping with Joe's cum."

Joe obeyed. He felt like a whore. He was excited to be a whore for Mistress Sarah and Miss May.

"Now push it back into your sissy pussy. Josie."

The plug slid back into his asshole easily. Joe felt dirty and slutty pushing the cum covered plug into his ass. His cock twitched as the plug pressed deep into him. Having his cum pushed into his ass mentally took him to a deeper level of kinkiness and submission.

"I feel so slutty," admitted Joe with delight.

"Good girl," encouraged Mistress Sarah. "You are a perfect sissy whore now Josie. You've got cum dripping off your lips and fingers and Joe's cum is in your sissy pussy. That's how a whore feels after a good night with a man. You've got one thing left to do Josie. Show me how slutty you want to be for Miss May and me. Drink up the rest of Joe's cum."

Mentally Joe had become their sissy whore and accordingly he obeyed Mistress Sarah's command with great pleasure. He tilted the cup upward and started to drink down the cum. Miss May put her hand on the cup it forced it back down slightly.

Seductively she said, "Slow down slut. You want to enjoy your creamy treat don't you?"

The creamy goo oozed into his mouth. He felt like a used whore and he loved it.

End of PART 2 



Discovering Mistress Sarah's World Pt. 03



Chapter 7: A Brief Digression 

Mistress Sarah sat naked, in a stiff padded chair in front of a large vanity. She waited patiently for her two sex pets to return. It was time for Joe to learn how to properly dress her for a night out and she wanted him in full sissy attire for the event. May had been charged with the task of getting him back into his dress. In the reflection of the mirror Mistress Sarah watched May help Joe into his sissy dress. May slowly circled Joe and pulled down on the pink silky fabric, ensuring the shiny dress cascaded around his legs smoothly and wrinkle free.

Mistress Sarah's fingers leisurely caressed her own breasts as she watched the show. Her thumbs rubbed over her nipples causing a brief shiver through her body. It was an arousing sight to see May naked and dressing her sissy. May's body was slender and tight. Each time she leaned forward, Mistress Sarah was rewarded with the sexy image of her round tits dangling beneath her slim body. 

May moved behind Joe, which gave Mistress Sarah a clear view of him. Mistress Sarah teased her nipples as she took in the sight. It was her chance to admire Joe without him being aware. He was caught up in the moment with May and did not notice Mistress Sarah staring at him through the mirror.

To Mistress Sarah, Joe did not exist anymore; at least not on the surface. He was tucked away deep inside Josie. That's where he belonged and Mistress Sarah intended on keeping him tucked away as long as possible. Josie was her creation and she needed to thrive and be free. 

Mistress Sarah's pussy began to dampen as she admired her silk covered sissy. He looked pretty and docile draped in pink and white satin. The pretty silk bows all over the dress looked cute. May even added white lace gloves to his ensemble that matched perfectly with his white stockings. Aside from his face and neck, the only skin showing was from his wrists to the top of his arms. Mistress Sarah loved this image. The image of his strong and muscular arms disappearing into soft silk and lacy fabric hit an erotic nerve within her that caused her pussy to quiver in pleasure.

Needing to satisfy the heat between her legs, Mistress Sarah's right hand slid down to her pussy. She lightly traced her fingers over her soft pussy lips as she reminisced about her first days with Josie. She remembered how unwilling he was to being feminized. He admitted he was a panty boy, as most boys do, but was resistant to go much further. However with carefully planned teasing and seduction, his panty boy days were a thing of the past. 

Mistress Sarah's fingers grew wetter as she played with herself and thought back to the first time she convinced him to buy tampons. He was nervous and shy but he could not disobey her orders. He bought tampons and he inserted one into his ass and wore it all day at work. This was an exciting moment for both Mistress Sarah and him as it proved he had the courage to move down the path of feminization. 

Now the once defiant boy stood behind Mistress Sarah dressed in complete sissy attire. Tampons were a monthly routine for him. He had grown fond of butt plugs and dildos in his ass. Standing up to pee, never crossed his mind anymore. Mistress Sarah took great pleasure in knowing that her power and sex appeal were the reason for all this. Josie was her creation and her property. She would continue to mold and shape his mind and body into a pretty submissive femme boy. This is what she enjoyed doing and it was the only way boys were allowed into her world.

With her excitement building her patience grew short. "Hurry pets. Come to me," she demanded.

May and Josie hurried over to Mistress Sarah and stood on each side of her. 

"Kneel at my feet," ordered Mistress Sarah. 

Josie kneeled down in front of his Mistress. His kitty bell jingled around his neck.

Mistress Sarah looked over at May and in a gentler voice said, "You to May. Kneel next to Josie."

With both her pets at her feet, Mistress Sarah spread open her knees revealing her wet and swollen pussy. The smell of her sex was strong and delicious. 

"You two have been naughty getting me exciting like this. You need to take of this problem...quickly so we can get ready," ordered Mistress Sarah.

Mistress Sarah guided May's head between her legs. Josie watched her tongue lick up and down the length of Mistress Sarah's shaven pussy several times. Then her tongue disappeared into the hot wetness. Mistress Sarah held May's head against her sex and moaned in delight as May's tongue probed deep insider her. 

Josie was entranced at the sight of May's pussy lips peaking out at him while she kneeled and serviced Mistress Sarah. He grew hungry for her. He wanted to taste her. Josie leaned forward and followed his craving. He licked May's pussy lips with his needy tongue. Her lips felt velvety against his tongue. She tasted delicious and naughty. May opened her knees slightly and pushed back onto Josie's tongue. A two-way tongue fuck ensued.

May pleasured Mistress Sarah while Josie pleasured May. Josie's cock hung below him hard, throbbing, and untouched. This did not bother Josie for he knew his purpose was to serve and please woman. That in itself was rewarding for him. Josie also received pleasure from the plug that was still pressed tightly into his ass. He rocked slightly on his knees as he tongued May's pussy causing the plug to press against his panties and push deeper into his ass. Josie savored this simulated fucking sensation in his boy pussy.

Soon Mistress Sarah erupted into orgasm. Like electricity, it only took seconds to flow through to May. May reached one hand back and pressed Josie's head into her pulsing pussy. Josie pressed his mouth and nose into her tight wet hole and used his tongue as best he could to satisfy her orgasm. May moaned into Mistress Sarah's pussy as her orgasm took hold. Josie kept licking and licking until May finally pushed him away.

Josie was left kneeling and aroused, facing the two girls. Both girls looked satisfied and relaxed. Josie on the other hand was horny, and attentive. Although his cock was hidden beneath the sissy dress the expression on his face was filled with arousal. May wanted to have a little fun and so she ordered, "Lift up your dress princess. I want to see your sissy cock. I bet it's so hard right now."

"Yes...very hard Miss May," admitted Josie as he slowly lifted the hem of the dress. 

His cock was twitching on its own from all the excitement. May moved her foot to his cock and gently rubbed the underside with her toes. She teased, "Aww. Look how excited our little bitch is. Poor kitty didn't get to cum."

Josie pushed his cock forward, humping her foot. 

May held her foot firm and said, "That's it slut. Hump my foot. You are so desperate to cum aren't you?"

"Yes Miss May. Please may I cum," begged Josie. He rubbed his cock up and down the underside of her foot.

Mistress Sarah crossed her legs and sat back and watched. She was delighted at how May was maintaining control and power over Josie while teasing him. May's other foot joined in on the teasing. Both her feet cupped Josie's cock as he humped away. Josie was amazed at how skillful May was with her feet.

Again Josie begged, "Please Miss May can I cum? I'm so close!"

May quickly pulled her feet away and laughed. "You've already had an orgasm once today Josie. I think that's enough. I want you to stay hot and horny all night. That way you will be begging me to fuck you with my strap-on later tonight."

Mistress Sarah smiled and petted May's head. She complimented, "Nicely done. Good girl."

May smiled both inside and out, from the compliment. She was happy to please Mistress Sarah and also thrilled at her power over Josie.

Chapter 8: Dressing The Girls

For the next half-hour all attention was on Mistress Sarah. May was already well trained on getting Mistress Sarah ready for a night out so she knew what had to be done. She ordered Josie to pick out 4 or 5 panty and bra sets from Mistress Sarah's lingerie drawer. While Josie gathered these items, May worked on blow-drying and brushing Mistress Sarah's hair. Just as May was finishing with the hair dryer, Josie returned with a handful of panties and bras. 

"Let's see what you picked out princess," said May as she stood behind Mistress Sarah, brushing her long blond hair. "Hold them up one at a time for Mistress to see."

Mistress Sarah had a large collection of bras and panties. Josie tried to pick a variety of styles and colors, hoping that at least one set would satisfy her. He started with a purple lace bra and matching thong.

"Mmm. I love that set," cooed Mistress Sarah. "Sexy choice kitten, but let's see what else you have."

Josie held up each panty and bra. Mistress Sarah and May giggled a few times and complimented on how cute Josie would look in some of the items. Mistress Sarah finally settled on a black lace bra with black silk boy shorts. 

May had Josie bring the items over to Mistress Sarah and ordered him to dress her. He knelt before Mistress Sarah and slid the panties up her legs. She lifted her ass slightly off the chair allowing Josie to pull the panties all the way up. Next Josie picked up the bra. He had taken many bras off girls before but had never put one on a girl and so he felt awkward with the bra in his hands.

May noticed his uncertainty and hesitation. She joked, "don't be scared Josie. It's just a bra. You can do it."

Mistress Sarah added, "Soon you'll be a pro with bras dear. They will become a regular part of your wardrobe pretty. We don't want your titties getting saggy do we?" 

Josie's cock twitched at the comment. He did not know how serious Mistress Sarah was about him wearing bras all the time. For some mysterious reason the idea excited him. He could not imagine how it would be possible but at the moment it seemed thrilling.

Mistress Sarah stood-up and put her arms out for Josie. Josie slid the straps up her arms. It almost seemed cruel to be covering up such beautiful tits. Before the bra covered her tits, Mistress Sarah ordered, "Kiss them."

Josie gladly leaned down and gave each of her nipples a soft kiss and gentle tongue licking. Josie cock was raging hard beneath his sissy dress.

"Mmmm. So nice," moaned Mistress Sarah.

After enjoying her tits for a few brief seconds, Josie moved behind Mistress Sarah and pulled her bra up. To his surprise, he managed to clasp the bra shut with only a slight bit of fumbling. 

Even May was impressed. "Good girl," she said in a complimentary tone.

Next Josie was ordered to fetch a pair of panties from May's overnight bag. She would go topless for now because that was the way Mistress Sarah preferred her. He fished through the bag and found a pair of cotton leopard print panties. Josie quickly brought them over to May and kneeled before her. May stepped into the panties and Josie slid them up her legs. On a whim, he gave her pussy a kiss and a flick off his tongue before pulling the panties all the way up.

"Very nice," cooed May. "Now let's get you started on Mistress Sarah's hair."

May handed him a brush and stood back to watch. Josie lightly brushed Mistress Sarah's hair. 

Immediately May ordered, "Harder! Don't be such a sissy!"

Both May and Mistress Sarah laughed at the unintended pun. "Oh, that's right... you are a sissy," said May, amused. "Try to be more like a man when you brush her hair. I know it will be hard for you pretty, but just try."

Josie blushed at the humiliating remarks and giggles. His red face seemed to be a visual gauge on his arousal and submission. The deeper he blushed the more his cock swelled and the more submissive he became. Obediently he firmly brushed Mistress Sarah's long golden hair. He felt like a slave worshipping a Goddess.

May went to work on Mistress Sarah's make-up while Josie continued with her hair. Mistress Sarah relaxed and enjoyed the pampering from her pets. It was blissful for her to not have to give out any orders. She reveled in her Goddess state as her pets gave 100% of their attention to her.

In between brushing hair, Josie had to fetch various make-up items for May. Although most of the items were within reach of May, she still required Josie to fetch them. This served two purposes. First, it was a learning experience for him and second, it reinforced his obedience and slave status with May. 

May applied most of the make-up. While she worked she explained to Josie what she was she was doing. She even let Josie help apply some of Mistress Sarah's foundation, blush, and lipstick. Josie found the experience to be very gratifying. He enjoyed pampering his Mistress and was eager to learn about make-up.

After Mistress Sarah's hair and make-up were done, Josie followed May to the closet. She sorted through the large selection of clothes looking for a sexy outfit for Mistress Sarah. She finally settled on a simple black tank top with spaghetti straps and a pair of white denim shorts. 

"Here you go sissy slave," said May as she handed the items to Josie. "Now run along and dress your Mistress."

"Yes Miss May," replied Josie submissively.

Joe dressed Mistress Sarah in the tight fitting clothes. The top clung nicely to here large breasts and provided a breathtaking view of her cleavage. The shorts were made of stretchy denim that hugged her round ass perfectly. Joe felt a bit jealous, knowing that Mistress Sarah would be hitting the clubs in such a sexy outfit without him.

Next he helped her into a pair of dressy sandals that were both sexy and comfortable. Finally, May laid out a necklace, ear rings, and bracelets for Josie to put on Mistress Sarah. 

Mistress Sarah admired herself in the mirror and said, "Nicely done girls. It will be fun teasing all the boys and girls in my sexy outfit tonight. Maybe I'll bring one of them home to play with. Wouldn't that be fun Josie?"

"Yes, very fun," admitted Josie, hoping she would bring home a girl and not a boy. He knew anything was possible with Mistress Sarah.

"I'm sure they would love to watch Miss May pop your cherry sweetie."

Seductively May added, "I would love to put on a show."

Mistress Sarah said, "Well then Josie, you better make Miss May look nice and pretty for the show. I'll meet you two downstairs when you are done."

Upon Mistress Sarah's exit, May sat in the chair in front of the vanity. "O.K. Josie. Start with my hair."

"Yes Miss May."

Josie dried and brushed Miss May's hair. Then he was instructed on how to apply her make-up. This time Josie did most of the application himself. Putting on her foundation and blush was easy and fun for Josie. When it came to the finer things like mascara and eye shadow, Josie was awkward and clumsy. Often times Miss May had to touch up his mistakes. 

Miss May was always firm, but understanding with her criticism. When she was not satisfied with her eye shadow she criticized, "Too much Josie. I want subtleness to attract the boys, not clown eyes."

"Yes Miss May. Sorry," apologized Josie as he watched her wipe some away and touch it up.

It took two tries with the lipstick before Josie could get her lips to look acceptable to Miss May. Josie thought the brown glossy color was a sexy and glamorous accent to her lighter colored skin.

After the make-up was done, Josie retrieved a leopard print bra from her overnight bag. Wanting to treat her just as special as Mistress Sarah, Josie spent a few minutes attending to Miss May's nipples before pulling the bra all the way up. Her breasts were smaller than Mistress Sarah's but they were perfect for her body size. Josie loved their firmness and perkiness. He could not resist cupping her tits in his hands while he teased her nipples with his tongue.

Miss May took pleasure in the attention. His soft lips against her sensitive nipples caused an exquisite burst of pleasure . She could feel her nipples swell with arousal. She arched her back and lightly held the back of his head encouraging him to continue.

A soft moan escaped her lips, "ooohh, kitty-kat."

Miss May was sinking into a sea of pleasure. Her pussy came alive and slowly she was being swept away. She did not want it to stop but she knew Mistress Sarah was waiting and would be upset if they took too long. It took all her strength to fight her sexual urges. Miss May pushed his head away and said, "enough kitty-kat. You're going to get me in trouble. Mistress Sarah is waiting. Hurry and dress me." 

"Yes Miss May."

Josie pulled up her bra cups and secured the bra. Next he helped Miss May into a white tank top and a gray pleated skirt. Finally, he kneeled before her with a pair of heels. Miss May slid each foot into the shoes and Josie secured the straps around her ankles.

Josie thought Miss May looked sexy and flirty. "You look incredible Miss May."

"Thanks slave. I bet I'll make a few cocks hard tonight. What do you think Josie? Will the guys being dreaming of fucking me tonight?"

"Most definitely Miss May. I would want to."

Miss May laughed and looked into Josie eyes. "Silly Josie, you're just a sissy boy. I know your little clitty is all hard and swollen underneath that pretty dress but when I'm at the clubs I flirt with real men who have real cocks."

Josie blushed with embarrassment. For a brief moment, he wanted to show that he could be a real man but part of him was excited at his predicament. There was a strange thrill in being humiliated and knowing that he was her servant, preparing her for a night of flirting and possible sex.

Josie was confused at these emotions. Before he could get his thoughts together Miss May continued, "Don't worry Josie. Sissies are special to me too. You don't get to fuck me but I get to fuck you and I am so looking forward to it tonight."

Josie's cock throbbed in his panties. "Me too Miss May. I can't wait."

"I know sissy. You are a slut aren't you? Tell me that Josie. Tell me how bad you want me to fuck you."

Miss May's orders energized Josie with lust and excitement. "I want you to fuck me real bad Miss May. I want to be your slut."

"Mmm. Are you my bitch?"

"Yes, I am your bitch. Pleas fuck your bitch," begged Josie, his cock throbbing harder by the minute.

"I'm going to peg you hard bitch! That's what you want isn't it?"

Josie hesitated. He had never been pegged in the ass before and was nervous about a hard fucking. His hesitation was noticed by Miss May.

Miss May scolded, "Say yes Josie!"

Overcome by her authority Josie, replied, "Yes. Please fuck me hard! Fuck me anyway you want too."

Miss May's tone softened, "That's a good bitch. Come here sissy. Let me touch you up before our guests arrive."

"Guests," questioned Josie with nervousness as he walked over to Miss May.

Miss May began to reapply red lipstick onto Josie's lips. "Yes darling. Mistress wanted everyone to meet at her house so that she could show you off."

Josie's heart pounded in his chest. He was nervous about meeting other people while dressed as a sissy.

"It's just a few friends. They have all seen Nellie prettied up before. They are going to fawn all over you in your pretty dress."

Miss May's words calmed Josie. He knew that Nellie was a reference to Mistress Sarah's boyfriend, Neil. Knowing that the girls were into sissies changed the scenario a bit. The thought actually became exciting to Josie. He was looking forward to the attention.

Miss May picked up a blush brush and said, "A little blush with your red lipstick will give you the perfect sissy look kitty-kat."

She brushed the blush onto each cheek and inspected her work. "Perfect," she said. 

Miss May made Josie look into the mirror. "You look like a boy in a wig who has been playing with make-up...a sissy boy. Any more make-up and you would start to look like a pretty girl." 




Discovering Mistress Sarah's World Pt. 03



The dressing up seemed fun until Josie saw himself in the mirror. He thought he looked silly. With more make-up he might at least pass as a girl. He lightly protested, "I'd rather have the pretty girl look."

Miss May giggled at his embarrassment. It was the reaction she hoped for. "Aww. That's so cute princess. I know how bad you want to be a girl but you've got to grow into that. Right now you're just a sissy. Be the best sissy that you can be and then maybe you can progress to the next stage of your training. Understand?"

"Yes," replied Josie.

Josie understood what she was saying but his mind was swirling from all the mind games that Miss May and Mistress Sarah were playing with him. He wanted to progress to the next stage of training because he was having fun and he was in heaven being under their control. What made his mind flip was when Miss May said how much he wanted to be a girl. Josie questioned himself; did he really want to be a girl or was being a girl just better than being a sissy and that's why he wanted to be a girl? 

His mind was both confused and excited. He enjoyed wearing the lingerie and silky dress. He actually felt sexy in his lingerie. He was even impressed at how good his legs looked when they were shaved. Deep down Josie was looking forward to being completely feminized. These thoughts would have never occurred to him prior to meeting Mistress Sarah. In a matter of months she had changed who he was. 

Even his fantasies had changed. His fantasies were now all centered around being feminized and being Mistress Sarah and Miss May's play toy and servant. As Josie contemplated all this and realized how much he had succumbed to the power and control of his Mistresses, a strong wave of arousal washed through his mind and body. He was in a great place.

Josie's thoughts were interrupted by a wet sensation on his neck. Miss May sprayed a small amount of perfume on Josie and then herself. 

"Now you smell nice and pretty Josie," announced Miss May.

Chapter 9: Meeting Mill and Ayla

May took Josie's hand and led him downstairs to the living room. Mistress Sarah was just finishing a conversation on her cell phone. She hung up and said, "Perfect timing girls. Millicent and Ayla will be here any minute."

Mistress Sarah and May sat down in the living and ordered Josie to get each of them a glass of wine. A chilled bottle of white wine and several wine glasses were already set out on the kitchen counter. Josie uncorked the bottle, filled two glasses half full and carefully brought them over to the girls.

Before sipping her wine, Mistress Sarah commented, "You make a good sissy maid even though you are not in a maid's outfit. That day will come soon though."

"You'll look so cute as a French maid," added May.

"Thank you," replied Josie, doing a small curtsey for the girls. The thought of dressing as a French maid sent an exciting chill through his body.

"You can practice tonight princess. Be a good little maid for my friends o.k.," ordered Mistress Sarah.

"Yes Mistress. I will be glad to serve them. I will make you proud."

"I know you will dear."

A knock at the door interrupted their conversation.

May smiled and said, "Let's see what you got Josie. Go see who's at the door pretty maid."

Josie's heart beat quickened. He nervously looked over at Mistress Sarah, almost hoping she would over-rule May's order. He was not ready to show his sissy side to the outside world. Mistress Sarah enjoyed the scared look on her pet's fast. It was fun toying with him and pushing his limits. 

She was quick to respond to his questioning look. "Go on slave. Do not hesitate when given an order. Hurry now. Don't keep my friends waiting."

Josie headed toward the door nervously. In the grand scheme of things, what he was doing was not a big deal. After all Ayla and Millicent were expecting to see a sissy. It was all the unknowns that frightened Josie. Many thoughts ran through his mind. What if it was someone else at the door? What if there were other people walking by? Would Ayla and Millicent laugh at him?

He had little time to ponder the consequences. He opened the door blushing and nervous. Two beautiful girls stood before him, smiling and taking in the sight of a sissy dressed in a pink and white dress, a brunette wig, and a touch of make-up. Josie quickly introduced himself, saying whatever came to mind. 

Shyly he said, "Hi I'm Josie. Welcome to Mistress Sarah's house. Please come in." His nervousness was evident in his wavering voice. 

Both girls could not help but giggle but their giggles were followed by a warm welcome. 

"Hi Josie. I'm Ayla. Sarah has told us all about it you. It's so nice to finally you meet you in person." Ayla was tall with a golden-brown skin tone. She had a beautiful exotic look.

The other girl looked several years younger than Ayla.. "I'm Mill," she said cheerily. Her eyes lit up as she stared at Josie. "I just love your pretty dress Josie. The lacing around the hem and sleeves is the cutest!"

Mistress Sarah and May joined the group just inside the doorway. Mistress Sarah beamed like a proud owner, "Isn't she adorable in her sissy dress. The shiny silk is so sexy and pink really suits her well."

Ayla leaned forward and placed a hand on the apron that was embroidered in white silk. "I love this apron. The bows around the bottom are so pretty."

"Turn around princess. Model your dress for Mill and Ayla," ordered Mistress Sarah.

Josie turned slowly in his dress. He did not expect this much attention from the girls. His nervousness and embarrassment washed away as they showered him with pretty feminine compliments. Josie noticed that the girls did not acknowledge him as a male in any sense. Right from the start they referred to him as 'her' or 'she' and this excited him for some unknown reason.

Josie's senses and erotic nerves suddenly came alive. As he slowly circled, he felt his stockings rubbing over his skin and he felt his cock straining against his soft frilly panties. His arousal grew making him more aware of the plug in his ass. Once his mind re-connected to the wonderful sensation of the fullness in his ass, it sent his arousal into overdrive. Josie was amazed at how quickly he became fully aroused simply from showing off his dress.

After Josie did a complete circle, May said to Ayla and Mill, "We did her nails also. Show them Josie."

Josie held up his hands, showing off his pink nails through the white lace clothes. Both girls admired them and complimented Josie on how well the pink color looked on him. When all the fawning and admiring finally came to an end, Mistress Sarah ordered Josie to pour two glasses of wine for the new guests. Josie walked away feeling more confident and excited about his sissy state. He was eager to please all the girls.

Josie obediently delivered the wine to the girls, who were now seated at the dining room table. They were chatting, giggling and working on some type of craft. The girls kept Josie busy with various tasks such as retrieving scissors and glue, refilling wine glasses, and bring out snacks. When he was not carrying out a task he was made to stand by the side of the table, hands behind his back, attentive and waiting for the next order. 

With a few glasses of wine in them, the girls became giddy and playful. After some giggling, Mill said, "Josie pretty, come over here. May told me you've got some cute undergarments on. I want to see them."

"Yes Miss Mill." Josie walked over unsure what to do. He looked at Miss May for direction.

"Go ahead pretty. Take off your dress."

Mill jumped to her feet taking an interest in Josie. "I'll help you," she said with a smile.

Mill unzipped the dress and helped Josie pull it over his head. The whole night was such an erotic tease for Josie that he could not control his arousal. His hard cock was clearly visible in the frilly panties.

"See what a horny bitch she is," commented Miss May. "She just loves being all pretty and prissy."

Mill reached around and squeezed his cock. Josie's body tensed with pleasure at the unexpected thrill. She rubbed it lightly though the panties. "What a nice big clitty you have, cooed Mill."

Joe sensed a deep lust in her voice. His eyes closed as he sank into oblivious pleasure.

"Carful Mill," warned Mistress Sarah. "She might just explode. Josie's new to all this and is very weak."

Mill whispered so that only Josie could hear her, "You are weak. Mmmmm. I like that." Then she gave his cock one last squeeze.

Josie was standing close to Ayla so she got a good view of him. She focused her attention on his stockings. "You have very sexy legs Josie. I'm jealous."

Miss May said to Ayla, "Aren't the big bows at the top of her stockings so sexy?"

"Yes, they are adorable and very bridal. We have a blushing bride," giggled Ayla.

"She's my bride," laughed May. "My little bride is going to get her first good fucking tonight. Show them your tight ass Josie."

Josie turned around. The girls commented on how nice his ass was and they could not resist touching it. Josie felt their hands rubbing and cupping his ass cheeks. Mill's hand slid between his legs rubbing his balls and the slid up the underside of his cock. All the touching and teasing was driving him wild.

Josie could sense that both girls were excited and turned on from admiring and touching him. This fueled his arousal even more. Mistress Sarah and May joined in on the fun. Mistress Sarah pulled Josie's panties down to his thighs, exposing his ass. "Isn't that beautiful," she announced.

Mill pressed on the plug that was in his ass, sending an erotic spark through his body. "You didn't tell us that her pussy was full. No wonder why she's all horned up."

May reached around and started playing with the plug in his ass. She gently fucked him with the plug. "We're getting the slut warmed up for later tonight."

Josie moaned at the pleasure. He was sinking deeper into an aroused and feminine state. "That's feels incredible Miss May." His cock was twitching and dripping, which did not go unnoticed by Ayla. 

Ayla rubbed her hand over the top of his cock and then massaged the dripping cum along his shaft. In just a few seconds his cock was shiny and wet all over. For a moment all four girls had their hands on Josie, caressing his ass, balls, and cock. It felt amazing and Josie did not want it to stop but he knew he could not last and he knew he was not allowed to cum.

"Please stop," he moaned. "I'm not going to last much longer."

The girls giggled and their hand slowly retreated from his cock. Mill's finger lingered a few seconds. She was the last to touch him and she pulled away not a moment too soon. Another second and Josie would have surely exploded. He was teetering on the edge of orgasm. The girls watched with delight as his cock twitched. His eyes were closed and it was clear that he was concentrating hard to not go over the edge.

There was not a dry pussy in the room. Josie's struggle was what brought all the girls together. Mill, Ayla and even May were drawn to Mistress Sarah because of her natural ability to craft situations that exploded with pure arousal and kink. To see Josie enveloped in uncontrollable stimulation and teetering on the edge was sheer ecstasy for the girls.

With the smell of sex in the air and with four pussies getting wetter by the second, the situation was on the verge of bursting into a sex-fest. Mistress Sarah was not ready for that yet. She had a plan for Josie and she wanted to stick to it. It was hard for her to not get carried away herself but she mustered up the strength to take control of the situation.

Chapter 9: Sissy Assignments After Josie's cock stopped twitching and his breathing became less laborious Mistress Sarah announced, "Well I think that's enough teasing for our pet now. We've got to hit the clubs so Josie can get started on her assignments."

"Assignment," questioned Josie.

"Yes precious," replied Mistress Sarah. "The girls and I have come up with some wonderful assignments for you to help with your femme training."

"We even made you a cute diary for you to track your progress and express your feelings through the transformation," said May. "Take a look."

May held up a small book. On the cover, in pink glitter, it said Josie's Diary. A silver princess crown and wand accented the cover. Josie looked at it and realized the diary was the craft that the girls were working on. Seeing his female name on the cover added a new sense of reality to what was happening to him.

Ayla questioned, "Isn't it cute Josie?"

"Yes, thank you. It's very pretty." Josie was impressed at their thoughtfulness.

Mistress Sarah then explained his assignment. "Josie sweetie, on the first few pages of your diary we have started a few entries in your diary. While we are out tonight I want you to finish the thoughts that we started. Be sure to fill all the blank pages in between entries, o.k. princess?"

"Yes Mistress," replied Josie.

"Some of the items you can start on right away. For example, the first page in your diary says 'When I first saw Mistress Sarah I felt....' 

You need to write a paragraph to complete that thought. You already know enough to do that. However a few pages back the entry says 

'I went through Mistress Sarah's panties and tried them on. My three favorite pairs are....'

Now you have not done that yet so obviously you can not complete this page yet. What do you think you need to do to complete this page?"

Josie said the obvious answer , "I need to go through your panty drawer and try on your panties."

"You got it! That is your assignment tonight Josie. Tonight is all about discovering the feminine world and the girl within you. I want you to explore through all my stuff while we are out. In order for you to blossom into womanhood you need to discover and experiment with girly things."

"Girls don't become women overnight," added May. "The same applies to sissies. Mistress Sarah and I have nurtured the feminine desires within you. Now you need to let Josie run wild with those desires and discover the wonderful world of womanhood. We are much more sensual then men. A woman's world is full of pretty scents, and soft fabrics...."

Ayla giggled and jumped into the conversation, "....and shades of lipstick and make-up.."

"...and let's not forget about pedicures, manicures, and pampering," chuckled Mill.

Everyone was smiling and having fun, including Josie. He was already starting to blend in as one of the girls.

Mistress Sarah continued explaining the assignment. "I want you to explore all those wonderful things. Go through my make-up, experiment with my lipstick and glosses and try on my panties, bras lingerie, skirts, dresses, and anything you can fit into."

Josie was becoming excited and aroused from his assignment. All these things seemed fun and exciting to do.

May added, "Don't forget about perfumes and lotions. I want you smelling pretty for me later. Fresh like a virgin for your fucking. O.k. Hun?"

"Of course," replied Josie in an erotic daze. 

Mistress Sarah continued. "Nothing is off limits Josie. Explore it all. Take your time as your explore and discover these things Josie. Think only of your senses. Pay attention to the scents, pretty colors and delicate fabrics. Submerse yourself in this secret dreamy world one step at a time. Make notes in your journal. What things do you like? What appeals to you? What makes your nervous or uncertain?" Mistress Sarah smartly questioned, "Can you handle it princess?"

"Yes. Thank you for this wonderful assignment. This is going to be fun."

"Of course it will be dear. Everything about being a girl is fun. Once you enter our world you are not going to want to turn back." 

"I'm already starting to feel that way," admitted Josie, somewhat surprised.

Each girl gave Josie a kiss on the cheek before walking out the door. Before Mistress Sarah left she gave Josie one final order, "Start with a bubble bath Josie. Spend 20 minutes soaking and thinking about how wonderful everything is right now. Then clean yourself up and go have fun."

End of Part 3



Discovering Mistress Sarah's World Pt. 04



Special thanks to Mistress Sarah and Miss May and Miss Mill who are my motivation for this story. Thank you for your guidance and wisdom and for the privilege of serving you and writing about you.



Chapter 11 Discovering the Girl in Him 

For the first time since he arrived at Mistress Sarah's house, Josie was left alone in silence. His cock was still throbbing from all the attention from the girls. It continued to throb as he thought about his exciting assignments for the night. He picked up the journal with his feminine name on it and opened it. 

Written in pink ink on the first page was, ''When I first saw Mistress Sarah I felt...." The remainder of the page was left blank for Josie to fill in.

Immediately Josie's thoughts went into action. He picked up the pink pen and started writing how exciting and nervous he was earlier in the day. He easily filled up the blank page. It was good that only 1 page was left blank. Otherwise Josie would have gotten carried away and filled the whole journal on the first entry.

On page two purple ink spelled out, "Today Mistress Sarah and Miss May dressed me as a sissy. I wore...." Several lines were left blank and then it read "My favorite part about being a sissy is..."

Josie thought it would be cute to match the ink colors on each page. He put down the pink pen and picked up the purple one. He described his sissy dress and sexy lingerie. Then he described how exciting it was to show off his pretty clothes to the girls. He admitted to loving all the attention as well as being covered in silky soft clothes.

Josie found that he was completely aroused at writing his thoughts in his journal. Reliving the erotic fun earlier in the day caused his cock to swell and throb in his panties. It was like Mistress Sarah was teasing him without even being there.

The next page had the sentence about trying on Mistress Sarah's panties. Josie could not wait to do this. Suddenly he remembered that Mistress Sarah ordered him to take a bath before he began. Realizing he was already disobedient by first writing in his journal, he quickly put the journal down and headed upstairs to the bathroom so that he could get back on track.

Josie was enthused about his assignments and really wanted to please Mistress Sarah by diving into the feminine world. Her words echoed in his head, 'you need to discover and experiment with girly things....a women's world is full of pretty scents...you need to submerse yourself in this secret dreamy world."

With her words of motivation, Josie was eager to experiment. He turned on the water to fill the bathtub and then explored the bathroom. He discovered bath salts and many scents of bubble bath. There were fragrances of Cucumber, Sweet Pea, Cherry Blossom and Sea Island Cotton. Josie smelled each one. Each scent that he inhaled softened his mind and melted him further into the feminine world. He loved the Cherry Blossom fragrance and decided to use this for his bath.

As the water filled and the bubbles foamed, Josie lit all the candles that Mistress Sarah had placed around the bathroom. He turned off the lights and stripped out of his bra, stockings, and panties. Finally he eased himself into the bath. 

The hot water surrounded and soothed him. The soft glow of the candles and the pretty scent from the bubble bath relaxed him. 'I could get use to this,' he thought. His manly traits drifted farther and farther away.

To his surprise, as he relaxed and his mind cleared, his arousal grew. There was so much arousal pent up inside that his cock hardened beneath the suds and beckoned for him to stroke it. He played with his cock and thought about how much fun he was having as a sissy. This was something he could never admit to his friends. It challenged his own principles but he was undoubtedly enjoying what was happening. Josie knew that he was deeply entangled in Mistress Sarah's seductive web and would not be able to escape. For reasons unknown to him her power and dominance fueled his arousal.

Soon Josie realized that soaking in the tub would lead to his demise as he would surely stroke himself to an orgasm. He made the hard decision to stop and move on with his assignment. After his bath he went right for Mistress Sarah's panty drawer and lingerie chest. Even though he had her permission, he felt naughty and perverted going through her panties and bras. 

Josie admired the many varieties of panties. He tried on silk, cotton, lace, and even mesh panties. There were boy shorts, thongs and French cut styles. Each time he slid on a new pair of panties his cock throbbed. He took his time, paying attention to their feel and look. The silk panties felt smooth and wonderful against his cock. Her thong panties tickled his ass. He loved how they felt when he walked and pranced around the room in them. Mistress Sarah had quite a selection of fur panties, which he enjoyed. The fur was on the outside of the panties but Josie could not resist turning one pair inside out and sliding them on. The fur felt amazing around his cock balls, and ass. 

He was horny and in a rare mood and was really enjoying the fur. Josie lay on his stomach on Mistress Sarah's bed and slowly began to hump the bed. The soft fluffiness all around his sensitive areas was mind blowing. His entire body shivered with pleasure as his cock and balls rubbed over the fur. It only took a few seconds to bring himself to the edge. It was hard for Josie to stop. He was desperate to cum and knew it would be amazing to orgasm with his cock buried on the soft fur. 

For a moment Josie thought he went too far. He could feel an orgasm coming on. He quickly raised himself up to his hands and knees to relieve the pressure on his cock. Josie struggled and concentrated on not cumming. He did not want to be disobedient. It took all his energy and focus to hold back and fortunately he was able to stop his orgasm. He slid off the fur panties and made a note in his journal about how much he loved them.

Next Josie moved onto bras. His shoulders were broad and so he could not fit into Mistress Sarah's bras and night gowns but he held them up to his body and admired them. He managed to slip into one long red silk nightgown that was obviously over-sized for Mistress Sarah. He enjoyed how the silk fabric contoured with his body. 

Josie made notes and comments in his journal while he played dress-up with Mistress Sarah's lingerie. He noted his favorite colors and styles. He commented at how sexy Mistress Sarah's red corset was. He even admitted that the thong panties felt nice rubbing along his ass.

The girls had laid out a roadmap for Josie to follow in his exploration into womanhood. The next few pages were presented like a self interview.

'My favorite perfume is....'

'My favorite nail polish is...'

'I thought I looked sexy in the following outfits....'

'I experimented with Mistress Sarah's make-up. I really liked....'

'I think my lips look sexiest when they are the color...' 

'When I go to the night clubs I want to wear....

Josie continued through the journal, experimenting with all the girly things and completing the sentences. Josie felt naughty and excited exploring all the girly things. His cock continually swelled and contracted as he played with Mistress Sarah's belongings.

He loved the fire red nail polish and glossy red lipstick. Although he could not squeeze into her clothes, he imagined himself as a sexy girl and thought about how much fun and sexy it would be to wear some of her skirts and low cut tops. As he immersed himself into her things, his mind transformed further into the feminine world. It had a brainwashing effect on Josie. Mentally he was starting to think as a female. He even convinced himself to start losing weight so that he would look sexy in Mistress Sarah's clothes.

Josie was having so much fun that he barely noticed the time go by. His cell phone rang and he was thrilled to see that it was Mistress Sarah. Josie answered it quickly.

"His Mistress Sarah." He could hear music and dancing in the background.

"Hello princess. Are you a woman yet?"

Josie blushed even though he was alone. "Getting there I guess."

"Yes you are doll. You're almost past the sissy phase of your training. Are you excited about that?"

"Yes Mistress," admitted Josie, not even sure what to expect next.

"Miss May needs to pop your little cherry for you to graduate to the next level of your training. Are you ready to be fucked by her strap-on sissy?"

Josie's cock swelled harder than he ever imagined as he realized the moment of his deflowering was approaching fast. "Yes, I can't wait."

"Neither can May. I made her wear a strap-on under her skirt so that all night she would be thinking about fucking you. I even let her fuck Mill in the back of the car on the way to the club, which got May even more horned up. She's been begging to leave all night so she can peg you."

The image of Miss May fucking Mill aroused Joe even more. The only words that came to mind were, "That's hot!"

Mistress Sarah laughed at his response and then gave a few orders. "We'll be coming home soon slut. Clean-up all my things that you played with. Make sure the place is nice and tidy and then pick out a pair of my furry panties to wear along with your kitty bell and garters and stockings. Be kneeling by the door waiting for us, o.k. Kitty?"

"Yes Mistress."

Joe heard Miss May's voice in the background yell, "Put a fresh coat of glossy lipstick on sissy. I want to see pretty blow-job lips on my cock."

"Yes Miss May," replied Joe. Then he heard giggles and the phone went dead.

Chapter 12: Josie's Deflowering

Josie kneeled by the door anxious for the arrival of his Mistresses. He could feel his ass pulsing around the butt plug in anticipation of what was to come. As he kneeled and waited he could smell the pretty floral scent of the perfume that he had sprayed on his neck earlier. He felt soft and girly from all the day's events. His was in a prime mode to be fucked like a sissy. Even though he was not touching his cock, it was pulsing and hard with arousal. He was both excited and nervous about being pegged. 

Josie heard faint voices outside. He tensed wondering if it was Mistress Sarah, Miss May, and Mill. The voices grew louder and he heard laughter and footsteps approaching the door. Josie's heart pounded in his chest and his cock pounded with its own heartbeat inside his furry panties. When the door pushed open and Mistress Sarah and Miss May walked in. His excitement and submissiveness suddenly intensified like a blazing inferno.

Miss May was also burning with lust. She burst into the room and sought out her kitty-kat immediately. 'Where's my fuck bitch? I've got a nice big cock for you!"

Before Josie could even think to respond, Miss May pulled up her skirt and pushed her strap-on towards Josie's lips. She grabbed the back of his head and ordered, "Suck my cock bitch-boy!" 

Her strap-on pushed into his mouth and she started fucking him. Having no experience with sucking a strap-on, Josie struggled to keep up and gagged. Miss May was full of lust and she was in a semi-drunken state from a night of fun. She was in no mood for patience. She continued fucking her slut, ordering him to keep up.

"Come on bitch. You can do it! I fucked Mill earlier. Suck off all her juices slut."

This was not how Josie imagined his night starting. Everything was happening so fast and furious. It was not the slow gentle introduction to a strap-on that he fantasized about. To his surprise Miss May's forcefulness and commanding words took him into a heightened state of arousal and submission. His cock was fully erect and throbbing. His tight furry panties pressed the hot flesh of h is hard cock against his stomach. He could feel his ass muscles pulsing against the plug in ass his ass. He felt like a total whore and he loved it.

As soon as Josie was able to keep up with his Mistress' rhythm Miss May increased her pace. To get more leverage she placed her left foot up on a chair that was next to Josie, held the back of his head firmly and fucked him hard. His kitty bell jingled in rhythm with the hard oral pounding.

"Good bitch. Your pretty red lips look sexy around my cock. Keep sucking sissy. Get my cock nice and wet for you sissy ass."

Josie felt completely used and at her mercy. Sucking her cock and keeping up with her rhythm was the only thing his simple mind could focus on at the moment. He was nothing but a fuck-toy. Josie was so focused on keeping up with Miss May that he did not notice that Mistress Sarah had left the room and then returned wearing nothing but a strap-on.

Mistress Sarah could see the lust and hunger in May's face and body language. Her pussy tingled at the sight of Josie's helplessness and arousal. To see May powerfully man-handle him was remarkable and exciting. She wanted to join in on the fun 

Mistress Sarah hugged May from behind, gently kissed her neck and pulled her back. She whispered to May just loud enough for Josie to hear. "It's so sexy to see you fuck kitty like that. Let's move her into the bedroom."

May was on the verge of an orgasm from the pure erotic pleasure of the power exchange with Josie. It was hard for her to pull away but she knew that was best. She did not want to wear out Josie to early. May was thankful that Mistress Sarah intervened when she did. May grabbed a collar and leash that was stowed away in a nearby closet. She quickly snapped the collar around Josie's neck, attached the leash, and led him into the bedroom.

Josie was made to kneel on hands and knees in the center of the bed. While May slid out of her skirt and top, Mistress Sarah reached beneath Josie and squeezed his cock through the panties. Then she asked, "Enjoying my furry panties slut?"

"Yes Mistress. They are very soft and smooth. I had fun with then earlier."

Mistress Sarah continued to tease his cock. She inhaled deeply and observed, "You smell very pretty kitty. You must have enjoyed my perfume. How was your night of girl indulgence?"

"Incredible Mistress. I had so much fun. Thank you for letting me go through all your things."

"A girl has to learn somewhere, right? Isn't our girl world so much more exciting and fun than the boring guy world?"

"Yes Mistress."

"I only play with soft pretty girls Josie. You will be that for me right Josie? You want to play with me and please me don't you?"

Josie was completely aroused and entranced by Mistress Sarah. His mind was mush and he wanted to do whatever pleased her and Miss May. "Yes Mistress. I want you so bad. I am a soft pretty girl ready to play with you."

Mistress Sarah's hands slid down to his balls. She squeezed his balls firmly causing Josie to gasp. Her tone became firmer when she spoke. "You're not a pretty girl just yet. You're still our sissy bitch Josie." 

Mistress Sarah laughed and then stood to the side of the bed so that her strap-on was right at Josie's lips. "Time to suck my cock sissy," announced Mistress Sarah. "Come on slut, show me what you got."

Josie obeyed and went down on Mistress Sarah's strap-on. Little-by-little he took the cock into his mouth. It was a much different experience than the hard fucking from Miss May. He had to think about what he was doing. All the day's events had mentally put him into a girl frame of mind. He became a whore. He wanted to be a good cock sucker. He licked and sucked the strap-on as sexily as he could.

"That's good sissy," complimented Mistress Sarah. Her compliment encouraged Josie on. Mistress Sarah ordered, "look at me while you are sucking my cock."

Josie looked up. He felt slutty staring into her eyes. She had a look of arrogance and smugness that brought out the whore in Josie. Mistress Sarah started to slowly fuck Josie's mouth while he sucked. 

"That's a good bitch. You'll make a good fuck toy Josie."

Miss May joined Josie on the bed. She kneeled behind him and slid his panties down off his ass. Josie felt the plug in his ass sliding out. His heart started pounding in his chest knowing that one of his most sought after fantasies was about to happen. His cock throbbed with excitement. He wanted to stop sucking Mistress Sarah's cock and prepare for Miss May's entry into his boy pussy, but that was not an option. Mistress Sarah was not going to stop.

Josie heard Miss May declare, "I'm going to enjoy pegging this tight little sissy pussy."

Then he felt her strap-on push into his ass. Wearing the plug all day, kept his ass stretched so that her initial entry was not too startling. However, as she pushed in deeper it stretched his insides and he tensed and moaned. His moan was muffled by Mistress Sarah's strap-on.

"Relax bitch," instructed Miss May. "Take it like a good sissy."

Miss May rested for a moment with her strap-on about 1/3 the way into her sissy's boy pussy allowing him to get used to the fullness. Then she pulled back and then pushed in again going deeper than the last time. Josie continued to moan in discomfort.

Mistress Sarah pulled her cock from his mouth and coached him with a firm commanding tone. "Focus Josie....relax and take Miss May's cock in. Come on slut, show us what you got."

Miss May did not ease up. Josie had no choice but to open up to her and accept her. Her rhythm picked up just as he was getting used to the fullness. A new carnal pleasure filled his insides and overtook his mind as she fucked him. Miss May took his leash in her hands and pulled back on it causing his neck and head to pull upright. She wrapped the leash around her hand, keeping it taught while she pegged him.

Now fully into the pegging, Miss May yelled in a half moan, "Yes...you are my bitch now Josie. You belong to me. You are my fuck toy...This is your life now"

Josie enjoyed being conquered both mentally and physically by Miss May. He surrendered to her completely. "Yes Mistress. I am your bitch," he proclaimed between deep breaths of pleasure.

"You're just getting started bitch boy,' added Mistress Sarah. She pushed her strap-on back into his mouth and began fucking him. Mistress Sarah and Miss May altered their rhythms. At first they alternated thrusts, with one going in while the other went out. Then they switched so that they were both thrusting in and out of Josie at the same time.

Josie felt so dirty and twisted and whorish being fucked from both sides. The innocent man that existed many months a go was nowhere to be found. His altered image was feminine, slutty, submissive and desperate to be used. 'She' was their slave, their bitch, their sex toy to be played with as they desired. Josie urges were raw and primal and 'she' was turned on by every desecration and was eager for more. 

The fast and continuous fucking and verbal torment from both Miss May and Mistress Sarah left Josie in a mindless state. There was no opportunity to think. He just kneeled, opened himself up for their pounding and surrendered to the dark pleasures. After several minutes of the raping, Miss May ordered Josie to roll over onto his back.

Once on his back, Miss May grabbed his legs and forcefully pulled him towards the edge of the bed. Josie felt powerless. Miss May ordered, "Spread your legs whore. I'm going to fuck you just like a girl."

Josie did not speak. He just obeyed. He spread his legs, opening himself up for Miss May. Miss May grabbed his ankles, held his legs wide and thrust her strap-on into his ass. Mistress Sarah placed her hand on the back of Josie's head and tilted his head forward so that he was looking at Miss May fucking him. 

Mistress Sarah whispered to Josie, "Look at your Mistress Josie. Isn't she sexy? She's fucking you like a slutty bitch. Your are sissy bitch, aren't you?""

"Yes Mistress," moaned Josie. Mistress Sarah was right. May looked powerful and sexy, completely naked and thrusting between his legs. The erotic image of the pleasure on her face and her hard nipples and firm tits bouncing was burned into Josie's mind. 




Discovering Mistress Sarah's World Pt. 04



Mistress Sarah reached down and squeezed his cock and said, "Your clittie is very hard." Mistress Sarah stroked his cock while Miss May fucked him.

The pleasure was intense. Josie's insides were full of erotic fire as Miss May's cock pushed in and out of his boy pussy. The thought of being fucked on his back never occurred to him before. This strange twist thrilled him. He became a girl with his legs spread, his pussy filled, and his clittie throbbing. 

The mental domination as well as the pleasure in his ass and the stroking of his cock were too much for Josie to handle. An orgasm was building fast. Josie pleaded with breathless moans, "This is incredible. Please may I cum?"

Mistress Sarah released her grip on his cock so that he would not be sent over the edge. "Beg like a girl," she demanded. "Beg for Miss May to MAKE you cum."

"Please make me cum Miss May. I want to cum so bad! I want to cum like a girl!"

Miss May continued pounding his ass and demanded, "beg like a girl Josie. You sounded like a sissy boy not my bitch girl. Beg me with a pretty girl's voice."

Josie was so close to exploding. He did not want to hold back. In his desperation he simply obeyed without thinking. With a high pitched tone he begged, "Please make me cum like a girl. I am so close!"

Both Miss May and Mistress Sarah burst out in laughter at the silly voice that came from Josie. Miss May laughed so hard that she had to stop pegging Josie. She rested with her strap-on pushed deep inside Josie. While the girls found humor in the situation, Josie was still completely aroused and turned on and so close to cumming. Miss May's strap-on resting deep in his boy pussy, did not make things easier for Josie. His insides were hot with pleasure and cum was dripping out of his 'clittie.' Josie felt like a total whore wanting nothing but to cum while the girls laughed.

"Please don't stop," he begged in his girl's voice.

"That was a little better Josie but you need to work on your girly voice," laughed Mistress Sarah,

Miss May kept her strap-on pressed into her bitch and said, "That was cute slut. You've earned an orgasm. Cum for me right now! Tell me you're my slut!" 

As soon as she gave the command, Miss May started fucking Josie fast and hard. At the same time Mistress Sarah placed the palm of her hand firmly along the side of Josie's cock so that as his body jerked from Miss May's pounding, his cock rubbed against Mistress Sarah's palm. The pleasure was intense. With his granted permission Josie did not hold back. 

Cum spurted from his cock and he moaned, "I am your slut! I am your slut! I am a sissy slut for you!"

Miss May changed to slower, deeper thrusts. "Keep cumming bitch! Cum for your Mistress bitch," ordered Miss May. 

"Yes Mistress. Fuck me. I am your bitch," moaned Josie. Miss May's deep thrusts continued to milk out Josie's cum.

Miss May moaned as an orgasm surfaced within her. She felt powerful and sexy fucking her slave with his legs spread like a girl. The harder she pounded him, the more pleasure she experienced. She pushed hard, rubbing her pussy against the firm base of the strap-on. Her bitch was already done cumming but that did not matter. Her pleasure was all that mattered and so she continued to fuck him enjoying her own pleasure. Her body shook and tingled and exploded in pure arousal as she pounded her toy.

At the same time Miss May was climaxing, Mistress Sarah scooped up as much cum as she could from Josie's stomach and chest and forcefully rubbed her cum covered hand over Josie's lips so that all the cum poured into his mouth.

"Lick up all your cum," ordered Mistress Sarah. "Mmmm. I know you love cum princess. You are such a slut for me."

The warm creamy cum oozed into Josie's mouth and coated his throat as he swallowed. He felt dirty, twisted, and completely submissive being force fed his cum while his ass was being pegged. Mistress Sarah pushed her fingers into his mouth ensuring he licked up every last drop of cum. She scooped up more cum and pushed four fingers at once into his mouth. Josie enjoyed the powerful intrusion. He relished his helpless and submissive state. He did not want the violations to his body to end.

When Miss May's orgasm passed she collapsed on the bed breathless. Josie was left lying on his back, the strong cum taste lingering in his mouth. Mistress Sarah stood over her two pets excited at what she saw and proud at how Miss May took complete control of her kitty-kat. She was also thrilled at Josie's complete surrender. 

Mistress Sarah removed her strap-on. Then she moved over to Miss May and gently slid off her strap-on. She dropped them by the door and ordered to Josie, "Go clean them up slave."

Josie was exhausted and did not want to move, but he knew he had to. "Yes Mistress," he replied obediently.

Mistress Sarah's pussy was still hot and wet with arousal. She locked the door behind Josie and turned back to May. May had a special glow about her. She looked sexy and luscious sprawled out naked on the bed. Mistress Sarah crawled overtop of her sexy pet. It was time for the burning hunger inside Mistress Sarah to be attended to.

End of Part 4 



Discovering Mistress Sarah's World Pt. 05



Chapter 13 Sinking Deeper Into The Feminine World

*** Prologue - Joe has made a trip down south to visit for the first time, his online Mistress. Over the past few years she has slowly feminized him with the help of Miss May. Upon his arrival at Mistress Sarah's house, she puts his feminization into full speed. He spends his first day is sissy clothes and receives his first strap-on fucking by Miss May. Part 5 starts the morning after his fucking. ***

Josie awoke in the morning wrapped up in a pink comforter. It was soft and comforting despite the fact that he had been sleeping on the floor in the hallway. He had been banished from the bedroom by the girls. After he had cleaned their strap-ons, he was told that it was girl-time in the bedroom and that he was still a sissy. He was sent to the hallway but he stayed close to the door listening to the sexual tones of Miss May and Mistress Sarah. However, exhaustion took over quickly. It had been a long day and the pegging by Miss May followed by his explosive orgasm had drained all his energy. There were several orgasms that occurred behind the closed door but Josie did not hear them because he had quickly drifted into a sound sleep.

When Josie awoke in the morning he unraveled himself from the comforter and admired the red silk night gown that covered him. The girls had dressed him in the gown before sending him to bed. It was a short and simple gown. Josie thought the shiny material looked incredibly sexy and feminine. He loved the feel of the smooth silk rubbing all around his body. His clitty started to swell as he became more aware of the soft sensation on his skin.

Josie remembered Mistress Sarah telling him that in the morning he was allowed to crawl into the bedroom and kneel by the bedside. If he was lucky, the girls would play with him. Not wanting to miss out on any fun, he crawled toward the door. The gown draped around his body as he quietly pushed through the door. He could feel a slight soreness in his ass, which served as a wonderful reminder of the pleasures that took place jut several hours earlier.

Josie crept towards the bed on his hands and knees in the quiet room. Mistress Sarah rolled over and in a hushed tone said, "...ahhh here comes our kitty." She beckoned him on. "Here kitty, kitty. Come on pretty kitty....hop up on the bed."

Josie hopped up and snuggled between Miss May and Mistress Sarah and greeted them. "Good Morning Mistress Sarah and Miss May." 

They were both naked. He enjoyed the morning warmth of their bodies under the covers. He moved into a spooning position, facing Mistress Sarah. He was excited to be sandwiched between two naked bodies and he could not control his cock. It grew fully erect and pressed against Mistress Sarah's ass. 

Mistress Sarah immediately turned and pushed Josie onto his back. She firmly grasped his hard cock and said, "This is not the feel of a pretty girl. It's getting in the way. We will have to something about it."

"Sorry Mistress," apologized Josie.

Then May reprimanded, "And what happened to that pretty girl voice? Greet us again with your pretty girl voice."

Josie hesitated for a moment, remembering how they laughed at him the night before. He wanted to sound more like a girl. He concentrated and with a raised pitch said, "Good morning Mistress Sarah and Miss May."

To his relief the girls did not laugh. Miss May said, "Better Josie, but it still needs work."

Mistress Sarah lightly stroked his cock through the silk nightgown and said, "Yes princess. You need to practice your girl voice. That's the only voice I want to hear from now on. Only prettiness comes out of those girly lips of yours, got it?"

"Yes Mistress," replied Josie with his girl voice. His cock throbbed in pleasure not only from Mistress Sarah's stroking but also from knowing that another part of his maleness was being wiped away by Mistress Sarah.

Miss May's hands rubbed over Josie's chest and found his nipples hidden beneath the silk. She rubbed and pinched them until they formed pointy tents in the night gown. Josie was not used to having his nipples played with. A new wonderful sensation tingled inside him. Mistress Sarah's words from the day before about taking his time and experiencing the sensations of womanhood echoed in his mind. He loved the womanly sensations he was feeling from his nipples.

"Very sexy nipples," complimented Miss May.

"Thank you," moaned Josie.

The girls continued teasing Josie's body, putting him a state of complete arousal.

Mistress Sarah asked Josie, "How is your pussy feeling? May gave you quite a fucking last night. Your inner slut was on full display."

"I am a slut," admitted Josie. "My pussy is a little achy, but it's fine. I had so much fun yesterday."

Mistress Sarah continued to lightly stroke his cock and explained, "It always hurts the first time your cherry is popped. That's part of being a girl. Tonight it's my turn to fuck you Josie. It will hurt again but eventually your body will learn to accept our strap-ons with full pleasure. Soon your pussy will be molded into a perfect fuck hole to be used solely for our pleasure. That is its ideal state, don't you agree?"

The future state which Mistress Sarah talked about excited Josie. Her words made him feel submissive and feminine. He wanted to be their fuck toy and slut. It was hard to maintain his female voice with all the pleasure running through his mind and body, but he managed to squeak out a girly sounding "yes Mistress."

For his compliance Josie was rewarded with Miss May's tits. She lowered her tits to Josie's lips. He took her nipple into his mouth and flicked his tongue over it. He could almost feel Miss May's body shudder with pleasure. "Good Girl," moaned Miss May.

Miss May moved her other nipple to his mouth and Josie enjoyed licking and sucking it just as much as the first one. He was in heaven being nestled between two beautiful girls, enjoying their bodies while they teased him. Mistress Sarah was playing with his cock with a combination of light strokes and long slow pulls. It was the perfect mix to keep him fully aroused without sending him over the edge.

When Mistress Sarah was certain that Josie was awash in arousal she commented, "This is what girls do in the morning. Isn't it fun? Aren't you glad to be one of us Josie?"

Josie could not argue with that statement. Everything that he had done since he arrived at Mistress Sarah's house was full of fun and pleasure. He did not want it to stop. Mistress Sarah and Miss May were showing him a whole new world and he was loving it. Joe was a long lost soul now. Only Josie existed and 'she' was one of the girls.

Josie's entire body shivered with pleasure from the confession he was about to make. His body tensed and his back arched as he fought off an orgasm. Josie confessed, "Yes I am glad to be one of the girls. This is so much fun. Thank your for bringing out the girl in me. You two are amazing."

Mistress Sarah and Miss May's eyes met and they both smiled calculatingly. There was so much emotion, arousal, and conviction in Josie's confession that they new their slave had mentally transformed into their slutty bitch. At that moment both girls shared a special thrill of knowing they had completely conquered him. He was not just a feminized boy anymore. They had much bigger plans for Josie. He was a toy for them to play with anyway they wanted. He was a slave willing to do anything they wanted. 

Knowing that their slave had reached a perfect state of arousal and obedience, the girls stopped teasing his body. Miss May said, "We have so much more girl to bring out in you Josie. Today you will be completely transformed. Are you excited about it?" 

"Yes Miss May."

"Well then we must get our day started. Mistress Sarah and I could go for a nice breakfast." Miss May instructed Josie to make bagels and cream cheese for Mistress Sarah and her. 

Mistress Sarah slapped his cock and said, "and get rid of this too kitty. Tuck it between your legs so it doesn't get in the way. You can use a pair of my panties to keep it in place."

"Yes Mistress," replied Josie. He went over to her panty drawer and selected a pair of red silk panties. 

As he walked out of the bedroom to get started on his breakfast duties, Miss May said to Josie, "Practice your girly voice too. While you prepare our breakfast say out loud over and over again, 'I am a pretty obedient girl slave.' Make your voice as girly as you can. I want to be greeted with a pretty voice when you serve my breakfast."

"Yes, Miss May. I am a pretty obedient girl slave," replied Josie with his feminine voice.

"Good girl," complimented Miss May with a small giggle. Then she kissed Mistress Sarah and said, "This is so much fun. Thank you for letting me play with Josie with you."

"There is much more fun to come my pet," said Mistress Sarah as she gently brushed her hand through May's hair and enjoyed the warmth of May's naked body pressed against hers.

In the kitchen, Josie was preparing breakfast and repeating 'I am a pretty obedient girl slave' over and over again. Each time he said the words out loud, he experimented with the pitch of his voice until he finally found a pitch that seemed naturally feminine. 

Practicing his girl voice and getting the bagels ready distracted his mind enough for his cock to soften and shrink. Josie took the opportunity to tuck his cock back between his legs and pull on Mistress Sarah's panties to hold it in place. At that moment he felt a deep sense of submission and arousal. Having his manhood molded and forced into a pussy shape stirred up a strange pleasurable arousal inside him. His 'clitty' began to swell but was held back by the soft panties. He could feel its heat against his inner thighs. It was a wonderful new sensation. He wondered if girls experienced a similar sensation when they were aroused.

Josie heard footsteps coming down the stairs. He had planned on serving the girls in bed but they had decided otherwise. Mistress Sarah sat at the kitchen table in nothing but a pair of black boy shorts and Miss May wore only a white g-string. Josie was thrilled at how free-spirited the girls were by walking around the house almost naked. He could get used to this life quickly. He thought to himself, if this was how girls lived together, then being a girl was much more fun than a guy.

In his practiced girl voice he said, "Good morning beautiful Mistresses. Enjoy your bagels." He served them bagels and poured them glasses of orange juice.

Mistress Sarah complimented, "What a beautiful voice Josie. Come here darling and lift your gown for me."

Josie walked over to Mistress Sarah and lifted his gown up to his waist. Mistress Sarah rubbed her hands between his legs and said proudly, "Just like a girl Josie. Now I can play with your clitty the same way I play with May's. You are turning out to be a wonderful addition to our family Josie."

"Thank you Mistress," said Josie. He was excited and thrilled to be accepted by Mistress Sarah. He was also excited about having his clitty rubbed. It was very kinky and perverse to have his cock shaped in the form of a clitty and for Mistress Sarah to finger him like a girl. Lately it seemed that the more kinky and perverse things were, the more Josie like it. In Mistress Sarah's world, Josie was quickly discovering how much fun it was to be feminized.

Miss May was sitting across from Mistress Sarah at the table and was sipping on hot tea while reading Josie's journal. Josie blushed when he noticed her reading it. He could not recall everything he wrote the night before but he knew that in the height of his arousal, he wrote many embarrassing thoughts about himself; Thoughts that would make him ashamed and humiliated if anyone in his 'real' world read them.

Miss May giggled as she read entry after entry in the journal. "Josie, it sounds like you had a great time playing with all Mistress Sarah's girly stuff last night."

"Yes, it was fun," admitted Josie in a shy voice.

"Better hide your furry stuff Mistress Sarah. Josie has taken a liking to your fur panties."

"That's my girl," exclaimed Mistress Sarah. "We'll have lots of fun with fur Josie. It really makes your clitty tingle, doesn't it?"

"Yes Mistress. I love the soft feel of it."

"Mmmm. I love have it feels to princess. We'll have to buy you a nice set of furry lingerie princess."

Miss May read several other passages from the journal, out loud to Mistress Sarah. Hearing his words read out loud about how he liked panties and what his favorite lipstick and perfume were, made Josie blush. When he wrote those things, he was aroused and in submissive and feminine state of mind. His thoughts seemed sexy and fun at the time. Now, a day later, hearing someone else read them, embarrassed Josie. Knowing that those feminine thoughts came from him made it seem so silly. He felt like a pervert and a sissy. It was something that he would have never fathomed doing prior to meeting Mistress Sarah and Miss May.

As much as it embarrassed and ashamed Josie, he knew he would continue to do these things. He knew that Mistress Sarah and Miss May were systematically feminizing him. Little-by-little his manhood was being stripped away and he was being molded into a feminine slave. Josie had never wanted to be feminized but over time Mistress Sarah helped him discover a deep arousal and pleasure from this transformation. Being controlled and manipulated through Mistress Sarah and Miss May's seductive powers was thrilling for Josie. He was addicted to their control and he knew that he would continue down the path that they had planned out for him.

One of the greatest powers of Mistress Sarah was her ability to wash away the embarrassment and make it exciting for Josie. "I am so proud of you Josie," she said with pride. "Your journal entries are so honest, open, and thoughtful. It is exhilarating to read about your wonderful transformation. I can see that your training is working and that pleases me very much."

Josie smiled at Mistress Sarah's compliment. He was glad that she was pleased.

Mistress Sarah encouraged him on. "Josie, it's important that you continue to write about what you are experiencing. It will help you discover more about yourself and will provide a great history of your transformation. I want you to write about last night. Describe how exciting it was to have Miss May fuck you for the first time in your pussy."

Miss May smiled devilishly from across the table. She slid the journal towards Josie. "Yes, it was very intense and exciting Josie. Write lots of good things."

Josie sat down at the table. "Thank you," he said. "I will write all about it."

The girls excused themselves from the table, leaving Josie alone to write in his journal. Josie's clitty was already starting to throb in its tucked away position as he began to re-live in his mind, Miss May's wonderful pegging. He put pen to paper and wrote all about it in his journal.

Chapter 14 Blowing Josie's Mind

It was late Saturday morning when Josie descended the steps of Mistress Sarah's house wearing red satin panties, black fishnets stockings, and red heels. Josie was still getting used to heels. He had to hold onto the rail of the steps and walk slowly. He was fresh from the shower and clean-shaven. His lips were painted a bright glossy red.

Miss May had gone off to work for a few hours so it was only Mistress Sarah who waited for him in the living room. She sat on the couch with her legs crossed, waiting for Josie to approach. Mistress Sarah was dressed in a simple summer outfit that consisted of a low-cut tank top and short skirt.

As Josie approached, she smiled with delight. "The lingerie I picked out for you looks amazing Josie. The red really brings out your inner-slut. Feeling slutty, aren't you princess?"

Simply dressing in the soft feminine items had an arousing effect on Josie. Mistress Sarah's words ignited more arousal. Josie's cock was still tucked between his legs beneath the sating panties. He was wearing a thong and the thin string barely held his cock in place as it swelled as much as possible in its bent position. 

"Yes Mistress. I am in a slutty mood. I want to be slutty for you," said Josie with complete conviction. He was looking forward to being her slut.

"Good girl. We will have lots of slutty fun." Mistress Sarah admired his lips. "You did a nice job with your lipstick princess. Your lips look so sexy and kissable. They are a nice slutty color to. It looks good on you."

"Thank you Mistress."

Mistress Sarah uncrossed her legs and leaned forward. She grasped his panties and pulled them down to his knees. Josie's cock came free and Mistress Sarah watched with amusement as his cock quickly straightened and grew erect right in front of her, without being touched at all.

Mistress Sarah leaned back again and crossed her legs. She smiled up at Josie and said, "That's what I love about you pretty. You're always so horny and eager to please." Mistress Sarah patted the couch cushion next to her and said, "Come sit Josie."

Josie sat next to her, his panties dangled at the top of his knees, his cock was fully erect. Mistress Sarah instructed, "Look between your legs Josie. What do you see?"

Josie looked down and saw his hard cock pointing up at him. He was in feminine mode and so he said, "My clitty Mistress."

"No..no..dear," said Mistress Sarah with a tone of laughter. "That is much too big and vulgar looking to be a clitty. Tell me what it really is Josie."

Josie was a bit confused. "My cock," he said.

Mistress Sarah corrected him, "It is a cock Josie, but not your cock. Understand?"

Josie giggled a little embarrassed, "ah..yes Mistress."

"Stare at it Josie," instructed Mistress Sarah. "Look out it and see it as not your cock. It is foreign to you."

Josie looked down as his cock and imagined that is was not his. It was a strange thought.

"Who's cock is it Josie," asked Mistress Sarah. 

"Your cock Mistress," replied Josie. 

"Well, I do control and own it Josie but it is not my cock. It is your silly man's cock Josie."

Josie looked over at Mistress Sarah with a confused look. She continued, "The silly man that you brought with you. It is Joe's cock, right Josie?"

"Yes Mistress," replied Josie, still trying to fully understand where she was going with it.

"Look at your pretty fingers," ordered Mistress Sarah. "Whose hands are they?"

Josie held is hands up. The pink nail polish that was put on the night before still shined like new. They were definitely feminine looking. He thought he understood this game that Mistress Sarah was playing but he was not sure. "Josie's hands," he said with uncertainty.

Mistress Sarah confirmed his answer, "That is right Josie. I want you to take your man's cock into your hands Josie. Squeeze it and tell me how it feels. Go on dear."

Josie gripped his cock as instructed. He had touched his cock many times before, but this time was much different. He was now paying close attention to what if felt like. "It is warm and hard Mistress. It's hard, yet a bit supple."

That's right Josie. Your man's cock is so hard and warm. Rub his balls Josie."

Josie rubbed his hand along his balls. It sent chills through his body. "His balls are very smooth," observed Josie. 

"Yes. It's good that you noticed that Josie." Mistress Sarah was also pleased that he spoke about it in the third person. He was already disassociating himself from his cock. "Now stroke Joe's cock Josie. I think that will make him very happy, don't you."

"Yes," replied Josie. He started stroking his cock slowly up and down.

"Good girl. You are my pretty little girl slut right now, aren't you dear? You are dressed in slutty stockings and a naughty red thong. You have fuck-me pumps on and your lips are a slutty red color. Your pretty girl voice is even sounding more feminine and natural. Stare at your pink fingernails as you stroke that cock Josie. See how your pretty fingers are stoking that strange man's cock."




Discovering Mistress Sarah's World Pt. 05



"Yes Mistress," replied Josie, acknowledging that he was obeying her. 

It was a very surreal moment for Josie. He was playing the role of slutty girl. He was stroking his cock but imagining it as another man's cock. His mind was never wired for thoughts like this. Naturally the more he stroked the more aroused he got. Mistress Sarah took full advantage of this conundrum.

"Do you feel your arousal growing Josie? The more you stroke that man's cock the more aroused you get. It is fun stroking his cock isn't it?"

Josie could not deny the pleasure he was feeling. His mind was being overloaded with mixed signals. Was it Joe or Josie that was getting excited? Was his arousal from stroking his own cock or was he getting aroused at thinking about stroking another man's cock. He could not even believe that thoughts like this passed through his mind. Mistress Sarah was in the midst of a deep mind game with him and she was manipulating him and bending his thought process. Josie was aware of this but could not stop it. In fact he loved what was happening to him. The control she had over him heightened his arousal even more. He had to slow his strokes down to keep himself from having an orgasm.

Josie whispered in an aroused daze, "This is fun Mistress. This is so wild. You are blowing my mind."

Without missing a beat, Mistress replied, "I know Josie. That is why you are here slut. I am breaking you down and then building you into an entirely new living being."

Mistress Sarah stood up. "Seeing you stroke your man's cock is making me hot Josie. Help me take my skirt off so I can get to my pussy."

Mistress Sarah turned around and Josie unzipped the back of her skirt. Mistress Sarah stepped out her skirt revealing white lace panties. Mistress Sarah sat back down next Josie and slid one hand inside her panties. Josie could see the outline of her fingers as they pushed into her pussy. "Stroke. that silly man's cock faster Josie. Show me your slutty side. Squeeze a little cum out of his cock and make it nice and wet."

Josie wanted to please Mistress. He liked that she was aroused because of what he was doing. He stroked faster and fought the urge to cum. It did not take much for him to squeeze cum out of his cock. He felt slutty and perverted as his hands rubbed the cum all over his cock. With Mistress Sarah's continual encouragement he imagined that it was not his cock that he was stroking and rubbing cum all over. The gooey wetness felt incredible all over his cock and brought him even closer to cumming. 

Mistress Sarah continued to mold Josie's mind while he was in his erotic subspace. "Good girl Josie. Keep stroking Joe's cock and playing with his balls. It's important that you please him. It's also important that you separate yourself from him Josie. You need to build a wall between Joe and Josie. Josie is everything pretty, soft, and feminine. That's what you are for me right now, isn't Josie?"

"Yes," admitted Josie in his girl voice.

That's right princess. That pretty girl always existed in you and now she is out and free. You have shed that boring and rough manly shell. You have tucked Joe away deep inside of you dear, haven't you?"

"Yes Mistress," said Josie, still stoking his man's cock.

"Good girl. We have let him out to play for awhile but that's all part of your training sweetie. There are times where Mistress will want to play with Joe. On occasions I get the desire to be fucked hard and rough and I may summon Joe for that. You may also have the desire to stroke his cock and that's o.k. too. 

When you are with me and when you are not playing with that silly man's cock you must keep him hidden away and pushed down deep inside of you along with all his manliness and toughness. Understand?"

"Yes Mistress. I will keep him tucked away."

"Mmmm. That's my girl. Now I want you to play with my pussy while you stroke his cock."

Josie was thrilled at this request. Mistress Sarah slid her wet panties off and spread her legs. Josie thought her pussy looked delicious all shaved and glistening wet. He slid two fingers into her wet slit. His fingers were immediately drenched in her wetness. 

"That's it," moaned Mistress Sarah. "Mmmm. That feels incredible. You're my little whore Josie...fingering me and stroking your man at the same time. I like that slut."

Josie was excited to be her whore. He wanted to be kinky and dirty for her. His arousal and desire to be slutty multiplied with each twisted order he obeyed. He was thrilled to be in the erotic fantasy world that Mistress Sarah had taken him.

"Lick Joe's cum for me princess. Lick his sticky cum off your fingers."

Joe immediately obeyed. The slut in him was happy to do this for her.

"That's it slut. I know how much you like cum. Squeeze some out of your man's cock and lick it up for me. I want to see it on your tongue Josie. Put it on your tongue like a whore and stick it out for me to see."

Josie squeezed a big glob of cum from his cock and wiped it up with his fingers. He sucked the gooiness off his fingers and onto his tongue. The strong pungent taste of cum filled his mouth. He felt very dirty and perverted and he loved it. He stuck his cum covered tongue out for Mistress Sarah."

"Look at all that cum. You are dirty cum slut. Mmm.. Keep licking up Joe's cum. Mmmm..finger me harder Josie. Make me cum while you suck on Joe's cock."

Josie was eager to bring Mistress Sarah to an orgasm. Giving her an orgasm was his prize for serving her. He fingered her harder and faster with one hand. With his other hand he continued to scoop up the dribbles of cum coming from his man's cock and lick it up. In the strange twisted world that he was in at the moment, he became the slut and whore that Mistress Sarah summoned. He sucked Joe's cock and tasted his cum while he fingered his Mistress.

"Yes Josie," moaned Mistress Sarah almost ready to orgasm. "It's just you, Joe, and me...a threesome sweetie." 

Mistress Sarah's words were replaced with breathless moans and screams as an orgasm took hold of her body. Josie fingered her faster, in rhythm with her rocking body. It took all his will power to keep 'his man' from having an orgasm. Mistress Sarah pinched her nipples increasing her own pleasure. Her orgasm was deep, intense and fulfilling.

When Josie was certain Mistress Sarah had finished her orgasm, he cried, "Joe wants to cum really bad Mistress. Can I make him cum?"

Even though Mistress Sarah just had an orgasm, her arousal simmered as she thought about the mind fuck that would occur if she let 'Josie' give Joe an orgasm. Joe was completely into his femme personality and his mind was so twisted that he was talking about stroking his cock like it was another man's cock. She was pushing him past his perceived 'manly' limits that existed in his mind. Mistress Sarah lived for the mind fuck but it would have to wait until later. Mistress Sarah wanted to keep Josie in a total horny and aroused state all day so that he would grow needier and weaker and continue to be completely submissive. 

Mistress Sarah replied, "Not now Josie. We want to keep your man horny all day. If he cums now he will be boring and sleepy, don't you agree?"

Joe wanted to cum so bad his balls were aching but he knew Mistress Sarah was right. Reluctantly he agreed, "Yes Mistress, you are right."

"That's my girl. You are learning," said Mistress Sarah with approval. Mistress Sarah retrieved Josie's journal. "Here you go sweetie. I want you to write all about your first hand job with a man while it is fresh in your mind."

Before taking the journal from Mistress Sarah, Josie looked at his hands. They were sticky from rubbing the leaking cum all over Joe's cock. "May I wash my hands first," asked Josie.

"Use your tongue Josie. Just like a kitty," giggled Mistress Sarah.

Josie was still feeling horny and slutty and so he eagerly obeyed. He licked his palms and each and every finger while Mistress Sarah watched and encouraged him on. "Good girl. I know how much you love tasting Joe's cum. You've turned into quite a slut Josie. I like that about you. Lick it all up slut; Lick between your fingers too Josie. Good girl. You are doing a super job."

Josie felt incredibly slutty licking the cum off his fingers. He didn't really like the taste. It was strong and pungent but he did like how slutty and perverted it made him feel. He liked that Mistress Sarah was excited at his sluttiness and so he was happy to lick away. 

When his fingers were more wet than sticky, he stopped and thanked Mistress Sarah for letting him lick up the cum. "Mistress Sarah replied to him, "Very good slut. Now get started with your writing. Here let me help you." 

Mistress Sarah opened his journal to a blank page and handed him a pink pen. Then she said, "Start with this Josie...Today I gave my first hand job. It was very exciting to stroke my man's hard cock."

Josie wrote the words and then looked up at Mistress Sarah waiting for more. She waved her hand for him to continue. "Go on Josie. You finish the rest. Write about how fun it was and how much of a slut you were."

"Yes Mistress," replied Josie, already starting to write his next sentence. 

"Good girl. Make me proud Josie. I've got to run upstairs and do a few things. When I come back down I'll read your wonderful slutty journal entry." Mistress Sarah walked away smiling and very pleased at how her session went with Josie. Having Josie write about it in his journal was the icing on the cake. She knew that him reliving the moments in his mind and putting it on paper would further mold and cement his feminine personality and breakdown the few male barriers that remained in his mind.

The thoughts and words flowed easily onto the paper in his horny state of mind. Josie found himself stroking his cock with one hand as he wrote about stroking 'Joe's' cock and pleasing his man. He was writing for quite awhile but it seemed like only minutes had passed when Mistress Sarah returned. 

Mistress Sarah noticed that Josie's cock was fully swollen and glistening with wetness. She immediately commented, "Look how puffy and wet your clitty is sweetie. You must have really liked writing about Joe's cock Josie."

Josie was so deep into his girly personality that Mistress Sarah's comment barely made him blush. Josie replied, "I am so horny right now Mistress. I really want to cum."

"I know pet. I know how being a slut arouses you but I am not ready to have you cum yet. I own your orgasm. I own you Josie. I decide when and how you orgasm, isn't that right slut?"

Mistress's words were so firm and controlling. Josie's clitty twitched as he felt her control surround him. It was a wonderful feeling. "Yes, Mistress. You decide when I orgasm."

"Very good slut. Now don't ask again pet."

Mistress Sarah took Josie's journal and read his entry. She was extremely pleased at what she read. It was written completely from a female perspective and it was filled with lustful emotion. Anyone who read the passage would have thought it was written by a very slutty female girl who loved playing with cocks. There was not even a hint of manliness in the way it was written. 

From Josie's writings, Mistress Sarah could see that the split personality she formed in his mind was working as planned. She had discovered with previous boys that this mind game helped men transcend their male egos and become accepting of their feminine personality and all actions that go with it. It was a powerful tool for getting men to break past the typical limits and fears of thinking about other men. 

Seeing this type of transformation occur in Josie is what Mistress Sarah lived for. As she read the emotions and confessions in his journal, she felt powerful and supreme. She had molded his mind at the core and this influence that she had over him gave her a rush of pleasure. Her body shivered in pleasure and her pussy instantly became wet from powerful feelings inside her.

"A beautiful journal entry, " commented Mistress Sarah. We are going to have such a fun day."

Josie smiled at the complimented. He was in a happy and aroused state of mind and he was exciting about what was yet to come. It was a wonderful feeling.



Discovering Mistress Sarah's World Pt. 06



Chapter 15

Joe's first 'female' public appearance as Josie was approaching fast. He was nervous about it. Fortunately Mistress Sarah had kept him busy most of the day so his mind was distracted. Shortly after his mind blowing masturbation session with her in the morning, she left to run errands and visit friends. Before she left she gave Josie a list of chores to do.

Josie spent the day cleaning the house wearing nothing but pink lace panties, stockings, and bra. His cock was tucked between his legs in its 'clitty' form. Mistress Sarah even had him put on lipstick, a dab of perfume and a touch of blush and eye shadow.

Josie found it to be quite exciting to do chores all femmed up. As he moved through the house cleaning, he could feel the soft lace rubbing over his clittie, he keenly was aware of the tightness of his bra and the soft tautness of the stockings around his legs and toes. The smell of his perfume was inescapable and made him feel pretty and soft. He was enjoying being a slave girl to Mistress Sarah and Miss May. 

Josie was alone most of the day, living in his own fantasy world. Later in the afternoon he was cleaning the kitchen when he heard the front door open and a soft voice say, 'Hello.'

Josie thought it was Miss May and so he hurried out to greet her. He was mortified when he found himself staring at a beautiful girl who was much younger than him. It was the first time he encountered a stranger in his feminized state. Josie turned beat red and tried to cover himself up with his arms and hands. The girl covered her mouth with her hand and giggled at the sight.

"I'm sorry," apologized Josie in a panic, as if everything he was doing was wrong. "It's not what you think." Embarrassed, Josie rushed back into the kitchen for cover. His heart was beating a mile a minute. He could feel the heat of the embarrassment on his face. Josie was trying to figure out what to do when the girl walked through the door.

"It's alright sweetie," she said in a cool calm voice. "I know Mistress Sarah likes to play with sissies and pretty boys. You must be the project Mistress Sarah was talking about." 

The girls' voice and nonchalant demeanor had a calming effect on Josie "Project," Josie said in a confused voice.

"Yes. Mistress Sarah told me to bring my stuff." The girl lifted up a large pink metallic case and put it on the counter in front of Josie. She opened it for him to see. The top of the case opened on both sides to reveal several tiers of trays and compartments filled with brushes, make-up, and other vanity items. "The girl giggled. She said she had a big project for me to work on."

Josie had never seen such a large collection of make-up. As he took in the site and calmed down, his mind began to work better and he suddenly recognized the girl.

"You're Julie," he said like he just discovered something important.

"Yes, that's me."

"Mistress Sarah has told me all about you. She has sent me pictures of you. They are all beautiful."

"Thank you." 

Josie continued, "I feel like I know you even though we've never met. I'm Josie."

"Ah, Josie," said Julie, finally realizing who the boy dress in panties and stockings was. "Mistress Sarah has talked about you as well. You're one of her favorite sissies."

Josie blushed and smiled with pride at the same time. His thoughts were interrupted by the sound of Julie's phone. She pulled it from her pocket and looked at the caller. "That's Mistress Sarah." Her eyes lit up with excitement.

Josie listened as Julie talked.

"Hi Mistress Sarah....yes, I'm at your place now.....yes I ran into Josie...She was very embarrassed...." Julie looked at Josie and smiled. She giggled at something Mistress Sarah said and then she said, "yes..her face turned bright red and she ran into the kitchen."

Julie tilted the phone away from her mouth and said to Josie, "Mistress Sarah is very pleased that I embarrassed you."

Josie blushed again and his eyes darted downward. Josie's cock throbbed in his panties from the revelation that they were talking about him and that Mistress Sarah was getting off on his embarrassment. Even the way Julie was referring to him as 'she' and 'her' made Josie feel submissive and girly. 

Julie listened to Mistress Sarah for a few seconds and then looked at Josie. "Come here slut," she ordered in a somewhat commanding tone. Josie knew the Julie was submissive to Mistress Sarah and he could tell that she was a bit uncomfortable taking on a dominant role with him. He knew that she was being instructed by Mistress Sarah and so obeying her was a must. He walked closer to Julie.

Julie ordered, "Pull your panties down to your knees pretty slut." Her eyes quickly shifted to the phone after the order revealing a shyness. 

Josie obeyed. He felt a new level of excitement at obeying a submissive girl. It made him feel even more subservient to be ordered around by Mistress Sarah's slave. His cock immediately swelled when it was freed from the tight panties.

Julie giggled glanced at him and giggled. She reached her hand down and lightly squeezed and stroked his cock. Josie's noticed her nails were long and flawless. They were painted a sexy deep red color. His body shivered at her light teasing touch.

"She's very naughty Mistress. Her clitty is vey puffy."

Julie talked and giggled for a few more minutes while she teased Josie's cock. When she hung up the phone she used two hands to tease him.

"That feels so good Julie," moaned Josie.

Julie gave his balls a quick light tap. It was enough to startle Josie. She said, "That's Ms. Julie to you slut." Her tone was much firmer now. She was already warming up to her dominant side.

"Yes Ms. Julie," replied Josie obediently. 

"Good girl. Mistress Sarah said for me to get started on you right away." 

"I hear you are a pro with make-up Ms. Julie. Mistress Sarah said you learned a lot from all the modeling that you have done. I hope you can make me pretty." Josie was hoping Julie could do wonders with his face so that he could pass as a girl and not be embarrassed by looking like a sissy.

"You already have a pretty face Josie. You have nice fair skin. I'm going to make you look even more beautiful. First I need you to get all that hair off your face and arms."

The next few hours were a flurry of activity. After Josie showered and shaved, Julie had him slip into a long silk night gown and then she went to work on his face. She pulled out brushes, pads, sponges, and powder puffs. She was an artist working on a masterpiece. Julie used tweezers to shape his eyebrows into perfect thin arches. Then she used foundation, powder, and concealer to cover up any signs of roughness. She painted his face in blush, mascara, and eyeliner. She even glued long black eyelashes onto his existing lashes.

Just as Julie was finishing up, Mistress Sarah walked into the bedroom followed my Miss May and her neighbor Millicent. Upon seeing Josie's transformed face, the girls all got excited and fawned over him.

The girls admired 'her' pretty face and complimented Julie on what a great job she did. Josie was treated just as one of the girls. There was absolutely no acknowledgement that a male was even in the room. Josie was anxious to see what he looked like. "I can't wait to see," he said to Mistress.

Just a few more things Josie, "said Mistress Sarah. She brought over a wig with straight blond hair and carefully placed it on Josie's head, tucking under any of his real hair that was sticking out. Miss May went to work brushing the hair on the wig to make it nice and straight. 

Meanwhile Mill sorted through Sarah's jewelry box and picked out a pair if dangly clip-on earrings and a silver necklace that prominently displayed the word 'princess'. Mill put the jewelry on Josie and gave him a kiss on the cheek and whispered, 'you are a pretty girl."

Mistress Sarah held her phone up and snapped a picture of Josie. "Ready to see," she asked.

"Yes Mistress," replied Josie with nervousness.

Mistress Sarah flipped the phone around and Josie could not believe his eyes. He did not recognize himself in the picture. Julie did an amazing job blending the make-up together into a natural feminine face. With the blond wig he looked like a completely different person. He thought he looked genuinely female and pretty too. "I can't believe it," he said with excitement.

"It is you Josie," said Mistress Sarah. "The girl in you is free. Come look in the mirror."

Mistress Sarah grabbed his hand and pulled him to the large mirror in the room. He looked into the mirror amazed. He did not see himself. He saw a pretty blond girl wearing a silk night gown.

Mistress Sarah said, "Josie is real now, isn't she?"

"Yes Mistress." Josie's nervousness about his first feminized public appearance started to fade away after he saw how pretty he looked. For the first time he was feeling comfortable that he could pull it off without his being discovered. He was starting to get excited about the night.

Mistress said with excitement, "You are a pretty girl now Josie. There is no turning back." She reached down and grabbed his cock through the silk night gown and said, "I even have something very special for this."

Mistress Sarah went over to her closet and pulled out a small plastic bag. From the bag she pulled out a pair of white panties. Josie was stunned to see a realistic looking vagina peaking out from the crotch of the panties. Josie was speechless as Mistress Sarah slid the panties up his legs. She tucked his cock back between his legs and pulled the panties up to his waist. They fit extra snug all around him and completely molded away his cock. The back of the panties even had pads sewn in to give him a perfectly round ass.

Mistress Sarah rubbed her fingers along his new pussy. "Mmmm. Now you have a pussy just like me sweetie." She licked his ear and whispered, "I like fingering you baby."

Josie hit another surreal moment with Mistress Sarah. His legs grew weak and butterflies filled his stomach. It was hard to fathom the transformation that was occurring to him. He looked and felt feminine. He was Mistress Sarah's creation. It was impossible for him to understand the excitement and arousal that coursed through his body. He loved what was happening to him. 

Josie was in such a daze that he barely remembered Julie squeezing his chest together and applying a tape-like fabric to his chest to keep it in place. She smiled and said, "This is a trick of the trade to give you more cleavage Josie. Josie looked down and was thrilled to see that the muscles in his chest had been molded into soft breasts. 

Miss May brought over a black bra and helped Josie into it. It was a special bra that further pushed his chest together and upward, enhancing his cleavage even more. The tightness in his chest was unnatural but the feeling was thrilling to Josie. It was symbolic of how he was being molded into something new and exciting. The tightness created a bondage-like feeling and brought to life erotic and submissive feelings in Josie.

Miss May also inserted small breast forms into the bra to fill out each cup. Then Julie went to work with her make-up using another trick of the modeling trade. She brushed dark powder around the insides of his chest and carefully blended in lighter powder as she went to the top of his chest. When she was done Josie's cleavage looked even more impressive.

Next it was Mistress Sarah's turn. She wrapped a pretty lacy corset around Josie's breasts and stomach. With the help of Mill, Mistress Sarah pulled the strings as tight as possible on the corset and secured them in place. Josie was bound tightly all around and shaped into a perfect hour glass. Finally Mistress Sarah made Josie put on a pair of black satin panties overtop of his 'pussy panties', black heels, and a pair of tight white shorts. The shorts clung tightly to his newly rounded ass. 

The girls were thrilled with the outcome. They all admired and complimented Josie. Josie felt very pretty and sexy and all the attention from the girls excited him and helped him fall deeper into his feminine psyche. Cameras flashed as they took pictures of the newly transformed Josie. It was like prom night at Mistress Sarah's house and Josie was the young girl heading off to the prom. They made Josie pose on the stairwell; they took picture of him by himself and some with him posing with each of the girls and group pictures. 

Josie did not see his final look until he was brought in front of a full length mirror. He was completely blown away by what he saw. His eyes were immediately drawn to his cleavage. It was natural looking and impressive. The corset hid his stomach and his legs looked shapely and sexy in his heels. Julie had also used powder on his legs to help give them a smooth feminine look. Stockings would have been ideal but were not appropriate for the hot summer night.

Miss May commented, "Wow Josie. You're cleavage is almost bigger than mine. The guys are not going to be able to take their eyes off you tonight."

Josie's heart stopped a beat at the comment. He was so excited at being able to pass as a girl that he did not even think about the possibility of being attractive to men. Suddenly he was worried about being too pretty and too sexy. He did not want that at all. He did not want to deal with men.

Josie looked at Mistress Sarah with nervousness and said, "Mistress Sarah, I don't want to be attractive to men. I want to be a lesbian girl."

Mistress Sarah laughed with amusement and delight at his comment. She put an arm around Josie and gave him a kiss on the cheek and whispered into his hear. "Mmmm. You are my lesbian slave girl Josie. You are pretty and sexy and that's what we lesbians like too. You do want to be pretty and sexy for me, don't you princess?"

Mistress Sarah's words had both a calming and arousing effect on Josie. He replied, "Yes Mistress."

"Of course you do sweetie. Dealing with men comes with the package. If a man hits on you tonight or buys you a drink, it just proves how beautiful you are right? We will then now that your inner-girl has fully blossomed."

Josie's nervousness came back again. Being the tigress that she was, Mistress Sarah sensed his nervousness and it made her pussy dampen. She enjoyed toying with Josie. seeing the fear in his eyes. He was weak and under her control and she got off on that.

Mistress Sarah comforted her pet, "Don't worry pretty. Miss May and I will be there to help you darling. We will protect you and make sure no silly boy takes you home tonight, o.k?"

"o.k.," replied Josie, still nervous.

Chapter 16 The Night Club

Mistress Sarah could feel Josie shaking as she held onto his arm while they walked from the car to the entrance of the night club. The music from the night club was so loud that it echoed into the streets and pulsed the air around them. Josie's heart seemed to pound in rhythm with the fast beat of the music. "It's going to be o.k. pet. You're surrounded by girls. You are blending right in."

Mistress Sarah was right but it did little to comfort Josie. He was a nervous wreck. When the group of girls approached the entrance the bouncer asked for ID's. Julie, May, and Mill all fished into their purses for their ID's. Josie looked over at Mistress Sarah in panic.

"It's in your purse darling," whispered Mistress Sarah.

A small purse hung from Josie's wrist. Mistress Sarah had given it to him just before they left the house. It was a cute Vera Bradley purse with a pink and black floral design that added to his feminine style. Josie did not know its contents. He opened the purse to find a lipstick, eyeliner, gum, and an ID. He was shocked to discover that the picture on the ID was him with a wig and make-up. He had little time to think about it as the bouncer reached for the ID. Josie handed it to him. He was blushing and his legs were shaking as the bouncer looked at him and inspected the license. It was only seconds but it felt like forever before the bouncer handed back the ID and allowed him to pass.

Mistress Sarah put her arm around Josie and gave him a kiss on the cheek. "See love, you made it in. You are all girl. I think the bouncer was even flirting with you." 

Josie felt a small rush of excitement that he had gotten passed the bouncer. This small win eased his nerves a bit. "How did you get this," asked Josie in amazement as he inspected his new ID. It was a North Caroline license and had his full feminine name on it. It even had his sex listed as female.

"Remember the picture I took of you earlier today when your make-up was all done and you looked so pretty? I e-mailed it to a friend who is a pro at making ID's. He did his thing and dropped it off while we were getting ready. It is a real license lover. Josie officially exists now. Isn't that exciting princess?"

"Yes it is," he replied. Having an official ID made his feminine transformation more of a reality. He felt butterflies in his stomach and his cock tingled in his panties at this realization. 

Mistress Sarah, May, Julie, Mill, and Josie causally walked through the crowd of people. Josie stayed close to the girls like a lost puppy. His steps were uneasy as he was still learning to walk properly in heels. He glanced around the room and noticed that the small entourage of beautiful girls that he was a part of was getting many glances from both males and females. A few guys even smiled at him. This was uncomfortable for him but at the same time he felt a sense of relief that he was being accepted as a female.

May grabbed his wrist and pulled him towards a bar. "Come on Josie. Let's get drinks for everyone."

She ordered a Cosmopolitan and four Mojitos. When the bar tender brought over the drinks, Miss May pushed the pink Cosmopolitan over to Josie and giggled. "I got a nice pink girly drink for you pet." 

"Thank you Miss May." Josie felt a bit awkward having Miss May pay for the dinks but he did not have any cash on him. All he had was the purse that Mistress Sarah gave him. At this realization, Josie felt a sense of helplessness and complete dependence on Miss May and Mistress Sarah. He was in a nightclub, dressed as girl, in a town that was completely strange to him and he had no cash or credit cards with him. He felt very vulnerable but he knew the girls would not let anything happen to him.

Josie helped carry the drinks over to a small table that the girls had commandeered next to the dance floor. It was quite a feat for him to carry the drinks while walking in heels. He also felt restrained by the tight corset and the way his chest was taped together. Most people probably would have been uncomfortable with the tightness. However, for Josie the sensations were bondage-like reminders of his submissiveness to the girls and so he took pleasure in them. Josie took much shorter strides than what he was used to and he walked a bit awkward but he eventually made it to the table without spilling a drink 

Mill and Mistress Sarah were already flirting with some of the guys standing nearby. May joined in with the flirting while Julie and Josie remained quiet and submissive. Every now and the girls would bring Julie or Josie into the conversation by asking them a question. Josie did his best to maintain a soft feminine voice. He must have been convincing because no one reacted to him strangely. He even thought one of the guys was glancing at his cleavage every now and then. 

In no time at all another round of drinks appeared compliments of the guys. Millicent raised her glass to the group and said to the other girls, "here's to Josie getting her first drink paid for by a man." The girls laughed and Josie blushed as he tapped glasses and drank his pink Cosmopolitan.

Eventually the girls ditched the guys and dragged Josie to the dance floor. Josie had fun dancing with the girls. As the night went on, more free drinks flowed in and Josie grew more comfortable in his girl persona. He became his new identity. He let his hair down, laughed and drank with the girls and had a blast.




Discovering Mistress Sarah's World Pt. 06



Throughout the night, Julie kept reminded Josie to apply his lipstick. Mistress Sarah had assigned her as his beauty consultant. At Julie's command, Josie would open his purse, pull out his lipstick and apply it. At one point Julie took Josie into the Women's room and touched up his face with cover-up and powder. 

Mistress Sarah noticed Julie and Josie going into the Women's room. She waited a few minutes and then went in. "Hello slaves," she said amusingly. "Mistress needs attending to. Come with me." Her commanding presence was immediately felt by Julie and Josie

Like well trained soldiers Josie and Julie followed her into a large handicap stall. Mistress Sarah put the lid down on the toilet and sat on it. "Show me your pussies," she ordered.

Without hesitation, Julie slid her shorts and panties down to her ankles and stood straight up for Mistress Sarah. Josie was taken by surprise at the sudden command and instant reaction from Julie. He found himself staring at Julie's cleanly shaven pussy. His mind seemed to be stuck. Mistress Sarah snapped him out of it. "Josie, I gave you an order!"

"Yes Mistress," replied Josie. Unlike the military precision from Julie, Josie clumsily slid down his shorts and first layer of panties. He left on the panties with the sewn in pussy. Julie remained at attention next to him with her pussy fully exposed to Mistress Sarah.

Other girls were moving around the bathroom. Mistress Sarah did not care. She was Supreme and need not be bothered with what other people thought. Her right hand massaged Julie's pussy and her left hand caressed Josie's fake pussy. "Mmmm. This is nice."

Although Josie was being fingered through a fake pussy, his arousal heated up. Seeing Mistress Sarah rub between his legs like she was fingering him, set his mind on fire. His cock swelled and twitched in its bent position and tried to break free. Josie could hear Julie moan quietly. Her eyes were closed and she was biting her lip. She started rocking against Mistress Sarah's fingers. Josie thought he should do the same. Slowly he humped her fingers.

"Good girls," complimented Mistress Sarah. Then she ordered, "Julie. Take off your shirt and bra." 

Julie obeyed and hung them on a silver hook that was in the stall. She was now standing in front of Mistress Sarah and next to Josie completely naked except for a pair of black heels.

"She has beautiful, perky tits, doesn't she Josie?"

Josie looked over at Julie. She looked amazing naked. She had a slender body with perfectly sized breasts and a tightly shaped ass. Her skin was flawless, smooth, and inviting. Her nipples were already swollen. "Yes Mistress," replied Josie.

"Lick them," ordered Mistress Sarah firmly.

Josie was enthused at her words. He leaned to the side and started to slowly lick and kiss Julie's breasts and nipples. Julie cradled the back of his head, holding him close to her breasts. She moaned. "Mmm. Don't stop Josie. Your pretty little tongue feels good"

Mistress continued to finger Julie and Josie in the bathroom stall. The girls were in their own erotic world. The sounds of women chatting and moving around outside their stall were barely noticeable to them. Mistress Sarah raised her glistening fingers to Josie's mouth. "Taste my pet's luscious juices," she commanded to Josie.

Josie eagerly accepted her wet fingers and sucked off Julie's sweet nectar. It made him hungrier for her. No words were spoken. Josie just knew what was expected next. He kneeled down on the hard tile floor between the toilet and Julie and pushed his tongue into her wet naked pussy. A soft moan echoed through the stall.

Mistress Sarah edged forward on the seat, her thighs and knees entrapping Josie between her and Julie. She pushed his head, forcing his lips and tongue to press harder into Julie's fleshy pussy.. Josie enjoyed the helpless feeling of being smothered between the two Goddesses. "Make her cum for me Josie," whispered Mistress Sarah.

Josie lapped harder at her pussy while Mistress Sarah reached up and pinched Julie's erect nipples. Julie's hands found the back of Josie's head and she held him tight while she humped his tongue and face and quietly moaned in rhythm. Josie could feel her pussy spasm against his flicking tongue. Her wetness covered his tongue, lips, and cheeks. Excitedly he lapped it all up like a puppy enjoying a new treat. He did not want to stop but Julie finally pulled away when she had enough.

"Thank you Mistress," said Julie. Although Josie did most of the work, she did not even acknowledge him. The purposeful exclusion made Josie feel objectified and it excited him. 

"You deserved it pet. You're too damn sexy. Now go fetch the other two girls."

"Yes Mistress."

Julie dressed herself and slid out of the stall leaving Josie and Mistress Sarah alone.

Mistress Sarah ordered Josie to turn around. She spread her legs and said "Now it's my turn slut. Come lick my pussy." 

Still raging and excited from the fun with Julie, Josie's tongue quickly lapped at Mistress Sarah pussy. She squeezed her legs tight around his head and firmly said, "slow down slut. Nice slow licks."

Sorry Mistress," apologized Josie. Under her direction he slowly licked her puffy pussy lips up and down and in between.

"Mmmm. That's good," cooed Mistress Sarah. "Keep that nice steady pace until my other two sluts arrive."

Josie only licked for what seemed like a few seconds before Mill and May made their way into the stall. There were a few excited giggles at what they saw. Then almost instantly they joined in on the fun. Josie continued to lap at Mistress Sarah's pussy while Mill and Miss May ravaged Mistress Sarah's lips and tits with lustful kisses.

No one undressed but shirts were being pulled up and shorts unbuttoned to allow wandering fingers and lips access to the most sensitive areas. Josie was at the center, on his knees, engulfed in erotic moans, arousing scents, and sinful pleasures. The girls were consumed with each other. No one was touching him. His clitty was still tucked between his legs beneath his panties but he was in heaven from al the sights, sounds, and scents. It pulsed and throbbed in his panties just like a real pussy. 

With Mill and May ravaging Mistress Sarah's tits and Josie pleasuring her pussy, it did not take long for Mistress Sarah's body to erupted with orgasm. When the magical wave hit, Mistress firmly pressed Mill and May's heads into her tits and she squeezed her thighs tight around Josie's head. She felt powerful and at the top of the world. Her followers were doing everything they could to pleasure her and bring her ecstasy.

Pleased, Mistress Sarah composed herself and said, "Josie slut, you've got two more girls to satisfy." She giggled and continued, "You wanted to be lesbian lover. Now you are getting lots of practice."

Mill and Miss May smiled delightfully at each other as Mistress Sarah left them alone with Josie. Josie's knees were beginning to ache from kneeling on the hard bathroom floor. He wanted to get up and stretch but Mill and May were too eager to continue with the fun. They each took turns fucking his tongue and cumming all over his face. 

When they were done, they had Josie stand and lean over the toilet with his hands pressed against the back wall. "We have a nice surprise for you Josie," said Mill with a hint of cruelness. Miss May pulled down his pussy panties allowing his cock to come free. It instantly grew hard and dripped cum from all the pent up arousal.

Miss May Squeezed his cock and said, "my, my, what a horny little slut you are." Her fingers expertly spread the oozing cum all around the head of his cock. The slickness felt amazing on his cock and he struggled not to cum. She moved her fingers up to his lips and without hesitation Josie sucked off all the stickiness. "Good slut. I know how much you love this," said Miss May.

"Time for your surprise," announced Mill. Suddenly Josie felt a plug being pushed into his ass. It happened so fast. In an instant he was filled. It was a startling but arousing sensation. 

Mill laughed in delight at how Josie gasped and jumped from the sensation. "We thought it would be fun to keep your pussy filled all night. You like that don't you slut?"

"Yes," admitted Josie. Both girls giggled. They pulled up his panties but did not tuck his cock back. 

Miss May looked at the unsightly bulge and laughed. "You need to do something about that slut. Hide it away before you come out." 

Mill added, "and fix your make-up. You're a mess."

It took about 10 minutes for Josie to return back to the table after Mill and May left him in the women's room. Miss May joked about how long it took him but she also complimented Josie on how well he touched up his make-up. Josie was happy to receive the compliment. He smiled and sipped his pink drink.

Still feeling devilish, Mill looked over at Josie and loudly said, "Josie honey, aren't there a lot of cute guys here?"

Not wanting to blow his identity among the crowd of people he bashfully responded in a shy girly voice, "umm...ahh....yes."

Miss May joined in on the fun. "Tell me sweetie, which guys do you think are cute?"

Josie blushed. He was quiet, unsure how to respond.

Mistress Sarah was pleased with the predicament that her girls had put Josie in. "Go ahead princess, it's o.k. It's just fantasy right? Which guy do you think is cute."

Wanting to please his Mistress Josie looked around the crowded room sizing up the different guys. He could have picked any guy but instinctively he wanted to impress the girls and pick a good one. Without really comprehending it, he found himself looking for attractive qualities in the men. He finally settled on one. 

In his bashful feminine voice he said, "The one in the red shirt by the bar is cute." Josie could hardly believe those words spilled from his lips.

"Why do you think he is cute," asked Mistress Sarah forcing him to blush even more.

"I don't know," mumbled Josie.

Miss May quickly jumped in, "There must be something that attracted you to him Josie. What do you like about him?"

Josie knew the answer. After all he did spend time picking him out of the crowd. It was just hard to admit it but he knew the girls would not let up. Finally he conceded, "Well, his arms are muscular and he's in great shape."

Mill giggled. "Yes he is. He got a cute butt too, don't you think Josie?"

"Yes, a cute butt too." Josie was surprised at the words coming out of his mouth.

Mistress Sarah agreed with Josie, "he is cute. Now pick out another guy Josie. If I were to bring home a guy for you tonight, who would it be?"

Josie's heart pounded fiercely in his chest. He knew Mistress Sarah was playing mental games with him and challenging his male psyche. The problem was he did not know how far she would go with it. 

Josie responded, "The guy standing on the dance floor over there." 

"Go on," she said. The other girls listened intently. 

Josie's cock twitched in his panties and his arousal level started to rise again. His horniness was not from the guy but rather from the situation his was in. Mistress Sarah was clearly in control of him and forcing him into an awkward situation. She was challenging his limits and he was too enraptured in her supreme power to resist. This was exciting for Josie.

This time Josie did not need encouragement. He was comfortable with his feminine psyche "he seems nice, he has a cute face." 

"Very good pet," said Mistress Sarah. Then she turned and walked toward the guy. She immediately engaged him in conversation. It was obvious that he was thrilled to be noticed by a Goddess.

Josie became nervous. He wondered if she was inviting him back. She was just teasing him he thought. Then Mistress Sarah pointed to Josie and the guy looked over. Josie glanced away and blushed. When he looked back he was surprised to see the guy walking toward him with Mistress Sarah.

Amazingly Josie stayed calmed. Deep down he knew he was at the Mercy of Mistress Sarah. She had a power over him that was irresistible. He was her puppet. He knew he would do whatever Mistress Sarah had wanted and that realization calmed him.

The guy came right up to Josie and said, "I hear you are the birthday girl tonight. Your friend here says you've got to do shots from strangers." He raised a shot glass filled with a blue liquid that had whip cream on the top.

Mistress Sarah winked at Josie. "Time for you to do a blow job," she laughed.

She made the guy sit down and hold the shot glass between his legs. Mill and Miss May cheered Josie on. "No hands allowed," yelled Miss May. 

By now the commotion had gotten the attention of several others in the bar. Josie leaned forward towards the guy's crotch. He could feel the plug in his ass pushing deep inside him as he bent forward.. Everything about the situation was twisted and perverted and in Josie's new world he loved every second of it. He put his lips around the shot glass and flipped his head back. The butt plug teased and pleasured him with every movement. Everyone cheered and laughed. Josie enjoyed the excitement of the moment. He smiled and laughed with everyone and licked the excess whipped cream off his lips.

Before he knew it another guy appeared with a big smile and the same shot. Millicent egged him on this time and soon Josie was doing another blow job shot to the cheer of the crowd. He did two more before Mistress Sarah and the other girls expertly shooed the silly boys away. Mistress Sarah and Miss May each grabbed one of Josie's hands and walked him toward the door. Mill and Julie followed.

"Time to go princess," said Miss May. "Your inner slut really came out there. Now it's time to put a show on for us. You're going to be our slut tonight."

Josie felt dizzy and aroused as he walked. The drinks and shots had put him into a drunken state. The liquor had also relaxed him, allowing him to fully immerse himself into his feminine persona. There was something about the way Miss May was talking to him the excited him. He wanted to be a slut for them. He wanted to be dirty and kinky and slutty. He was ready to do anything they wanted. 

Mistress Sarah added, "you were so sexy and slutty doing those blow jobs Josie. The guys were checking out your breasts and cute ass as you leaned over. I bet anyone of them would have licked the cream off your lips. I could tell you were having fun pretty. It is fun when you let the girl in you runs free isn't it.?

"Yes," admitted Josie imagining life as a girl.

Mistress Sarah quickly replied with a giggle, "Just wait until you do a real blow job."

Josie's mind was whirling with crazy thoughts and emotions and in his drunken state he could not process the thoughts. He did not know how to respond. Before he could think of anything Miss May said, "It's a good thing we saved you Josie. There's no telling what those boys would have done to you." Miss May laughed and added, "Another few minutes and they would have started whipping out their cocks. Then again, you're such a slut you would have probably liked that, wouldn't you?"

Josie was in a mood for impressing and obeying the girls and felt completely girly and slutty so he responded, "yes".

Everyone laughed. Mill said, "You really are drunk Josie. Perfect for us."

Chapter 17 Josie's First Lesbian Fest

Josie barely remembered the car ride home. There was lots of laughing and teasing of Josie. He was quickly whisked into Mistress Sarah's bedroom. Josie had the look of a helpless animal surrounded by a pack of wolves. In a matter of seconds the girls stripped down their prey to nothing but his panties. Millicent took pleasure in ripping the tape from his chest and seeing him flinch at the quick and sudden sting.

The girls also stripped off their clothes. Josie was the only one left with panties on. His cock was still pushed backwards between his legs in the shape of a pussy and his ass was still filled with a plug. The girls each took turns rubbing between his legs and kissing his nipples and telling him how pretty and sexy his was. While one girl rubbed another was lowering her tits to his lips and ordering him to lick.

Before meeting Mistress Sarah, Josie had never experienced a threesome and now amazingly he found himself in a room with 4 naked girls. The girl all knew what to do. Josie saw Julie licking Mistress Sarah's pussy. Mill was between Miss May's legs and Mistress Sarah and Miss May were both teasing and playing with Josie. Josie was overwhelmed and did not know what to do other than lay there like helpless prey.

Eventually his panties were pulled down and his cock sprung free and hardened instantly. Warms hands and lips pulled at it and teased it. Other hands pushed on the butt plug, teasing his ass. He was in complete heaven. Had it not been for the liquor he probably would have exploded into an orgasm almost instantly. 

Mistress Sarah was the first to lower her pussy onto his face. Josie lapped at her wetness while she humped him. At the same time Mill slowly stroked and licked his cock while Miss May and Julie serviced Mistress Sarah's tits. It was not long before Mistress Sarah's thighs tightened around his face and her pussy smothered him and convulsed into a deep pleasurable orgasm.

Josie barely caught his breath before Miss May assumed the position on his face. This time it was Julie teasing his cock and balls while Mistress Sarah and Mill played with May's tits. Josie continued to lick and fuck Miss May's pussy with his tongue, bringing her as much pleasure as possible. Soon Miss May was smothering him and cumming all over his face with her wet pulsing pussy. The scene was repeating again with Mill and then with Julie. Josie eagerly licked and pleasured each one of the girls. There was lots of laughter, giggles, moans, and teasing the whole time. 

All four girls had powerful and satisfying orgasms while Josie was left fully aroused and horny. His cock was so sensitive and hard from all the teasing and excitement that it was practically twitching on its own. The liquor was wearing off making it harder for him to refrain from cumming. He had a strong desire to cum but he knew he was not allowed. .

Mill and Miss May disappeared out of the room, leaving Josie with Mistress Sarah and Julie. "Go fetch my strap-on slut," ordered Mistress Sarah to Josie.

"Yes Mistress." Josie scampered off to get her strap-on. He returned with it and helped Mistress Sarah slide it on. Josie kneeled before Mistress Sarah with the rubber cock bobbing in front of his face. He was eager to lick and suck it for his Mistress.

"Very good slut. You will get your time with this soon enough." Mistress Sarah turned away from Josie and toward the bed where Julie was lying naked on her back. 

Mistress Sarah picked up a purple vibrating dildo that was lying on the bed. Josie heard it start to buzz and he watched as Mistress Sarah teased Julie with it. He had a perfect view of her pussy. With eyes wide-open and his cock hard as a rock, he watched Mistress Sarah slowly push the dildo in and out of Julie's pussy. Mistress Sarah used her other hand to play with Julie's nipples. Every now and then she would lean forward and suck her nipples or give Julie a long tongue kiss.

Julie could not help but writhe on the bed in erotic twists and moans. The vibrating pleasure forced her eyes shut and caused her lips to part in arousing breaths. She too wanted to cum. Josie could see the look in her eyes. He knew how she was feeling and he was jealous that it was not him lying on the bed, legs spread, and pussy throbbing for Mistress Sarah. He was jealous but he was also excited to see his Mistress in action with Julie. The mere sight of Julie's pleasure and Mistress Sarah's manipulative power kept Josie fully aroused. 




Discovering Mistress Sarah's World Pt. 06



When Mistress Sarah felt that Julie had been teased enough she turned to Josie and said, "Kitten, fetch me another strap-on. I'm in a mood to see one slave fuck another."

Josie retrieved a second strap-on, wondering which slave would be fucking which. Either prospect was an exciting thought. Mistress Sarah took the strap-on from Josie and turned to Julie. She carefully slid it up Julie's smooth legs until it was snug against her crotch.

"Ooohh. That looks sexy on you pet," cooed Mistress Sarah. "Stand-up and show our little slut your cock."

Julie's expression was filled with arousal and lust and she stood before Josie. She had used a strap-on with other girls before but never with a boy. She was submissive by nature but the thought of taking Mistress Sarah's sissy sub with a strap-on caused a sudden unexpected wave of pleasure to course through her.

"Doesn't her cock look delicious Josie," asked Mistress Sarah seductively.

"Yes Mistress." 

"You know what to do kitten. I know your slutty little tongue is dying to give it a lick."

Without hesitation, Josie took Julie's strap-on in his mouth. He looked up at her as he took it in. He loved the view of the underside of her naked tits. He could see her nipples swollen and pointing out. He could see her young and pretty face filled with uncertain arousal. He was sure he heard a soft moan escape her mouth when the tip of the strap-on disappeared into his lips. 

Julie was gentle as she pushed the strap-on in and out of his mouth. This was not acceptable to Mistress Sarah.

"Push harder," demanded Mistress Sarah. "She is a slut Julie. She can take it."

Julie quickened the pace but it was still not satisfactory. Mistress Sarah moved behind Julie. A riding crop seemed to magically appear in her hands. She gave Julie a light tap on the ass with the crop. Julie instinctively twitched and thrust her ass forward at the sudden slap, which caused the strap-on to quickly thrust into Josie's mouth. Josie accepted it with no problem.

Mistress Sarah said to Julie, "Much better pet." Then Mistress Sarah slapped her ass again with the riding crop and ordered, "Harder!"

Mistress Sarah continued to spank Julie's ass and command the she fuck her slut. Each swat became harder and quicker. She was in effect controlling the rhythm at which Julie fucked Josie's mouth. Julie's thrusts increased in intensity and her ass grew warm from the spanking. Julie felt like a puppet. She enjoyed this control that Mistress Sarah had over her. 

She also took pleasure in fucking Josie. It was her first time fucking a sissy and it was exciting seeing her strap-on push into his mouth and to see him kneeling and accepting it. She could tell he was struggling to keep up with the fast pace. This new power over him caused a mysterious pleasure within her.

The combination of submissiveness, power; pleasure and pain was overwhelming and quickly took Julie into a deep state of arousal. She could feel an orgasm rising within her. Her body and soul felt as if they were suddenly possessed by a lustful whore with a desperate need to cum. She grabbed Josie's head with her hands and began to thrust hard in and out of Josie's mouth. There was no escape for Josie. He simply had to accept Julie's strap-on and try not to gag. He was her fuck toy.

Mistress Sarah was delighted with Julie's sudden aggressiveness. She stopped spanking her and said, "That's it pet. Give her a good fucking!"

The mental pleasure of fucking Josie's mouth was uncontrollable. Julie moaned as she thrust her strap-on. The orgasm that ripped through her body took her by surprise. She did not think it was possible for the phantom cock to bring orgasmic pleasure to her. Julie held on tight to Josie's head and fucked him hard and moaned as her body coursed with pure pleasure.

"That was incredible," whispered Julie when she pulled her cock from Josie's mouth.

Mistress Sarah gave Julie a kiss on the cheek and whispered back, "I know. Sissy's are fun to fuck." She then turned to Josie and ordered him to kiss Julie's feet and thank her.

Mistress Sarah moved behind Josie while he was bending forward. As he was kissing Julie's soft feet, he felt a slap on his ass and heard commands form Mistress Sarah, "Get your ass up in the air bitch! Keep kissing Julie's feet."

Josie raised his ass and felt Mistress Sarah's lubed strap-on push into him. He was thankful for the plug that Miss May had pushed into him earlier. Although it was a bit painful when he initially took it, he was certain it was the reason why he was able to accept Mistress Sarah's strap-on with minimal pain. 

Mistress Sarah began to fuck his ass. "You're our bitch tonight Josie, aren't you?"

"Yes Mistress,"

"That's right sissy slut. Keep worshipping Julie's feet while I fuck your pussy. She is my slave but you are her bitch."

Josie did his best to kiss her feet. It was hard to concentrate on her feet with Mistress Sarah pounding his ass. Julie noticed his lack of attention. Not being shy with her new found power she pushed his head downward and said, "Kiss them bitch-girl. Smell my feet. Worship me!"

Josie inhaled deeply. The scent of Julie's feet took him deeper into submission. He enjoyed his predicament. Josie's mind was transformed into emptiness. He did not think. He simply did all he could to obey the commands that were spilling from Julie and Mistress Sarah's mouths. He loved that he was being used like a slutty girl. 

Subconsciously Josie's mind reeled in pleasure at the total degradation of the situation. Not only was he being emasculated by Mistress Sarah's strap-on and forceful words, but he was being required to submit to another slave. This contradiction established a new level of submission; a grander hierarchy in which Josie was at the very bottom. It seemed that the more he was humiliated and pushed down, the more he was compelled to obey and serve.

Mistress Sarah thrust hard and deep into his ass and kept calling him her sissy, her bitch-girl, and a slut. At the same time Julie pressed her delicate feet and toes into Josie's face for him to lick, smell and worship. Josie also felt Mistress Sarah's hands pulling and teasing at his cock as she fucked him. His cock was dripping and wet. He wanted to cum but he knew it was forbidden so he did all he could to hold back.

When he thought he could not hold back anymore he begged for release. He begged to cum. Mistress Sarah released his cock and thrust deep into his boy pussy. She laughed and sternly said, "No slut! Be strong for me!"

His denial seemed to fuel the fire inside Mistress Sarah. Josie simply braced himself and accepted her thrusts as Mistress Sarah pushed harder and harder and enjoyed her own orgasm at the mercy of her slave. Before finishing with Josie, she thrust her strap-on one last time into his sissy boy-pussy. She paused for a few long seconds, letting her cock fill his pussy and remind him of her power over him. Her strap-on demanded his attention and reinforced who owned him.

Josie's insides were alight with sensations. The strap-on milked cum out of the tip of his cock. The slightest touch on his cock would have sent him over the edge. He was at the mercy of Mistress Sarah. He hoped she would show mercy and allow him to cum. Before he could beg again she slowly withdrew her cock from his 'pussy.' He was left empty and wanting more.

"Please Mistress! Please don't stop," he begged.

Mistress Sarah laugehd, "You've turned into such a slut Josie. Pull yourself together."

Mistress Sarah slid off her strap-on and tossed it by the door along with Julie's. Go clean them up slut. We'll see you in the morning."

"Yes Mistress," whimpered Josie. He crawled over to the door, gathered the fuck toys and headed off to the bathroom. It was going to be another night of sleeping in the hallway, uncomfortable yet fully aroused.



Discovering Mistress Sarah's World Pt. 07



CHAPTER 18 A Life Changing Decision

Sunday morning was not much different than the day before for Josie. He woke-up on the floor outside Mistress Sarah's bedroom, dressed in a silk night-gown and his cock was hard and aroused when he awoke. Just like Saturday morning, he crawled into the bedroom. Mistress Sarah was waiting for him. She was lying on her side facing the door. She smiled at Josie and patted the sheets in front of her. 

"Come here pretty kitten," she said in almost a whisper.

The soft sheets were wrapped around Mistress's body, covering everything up to her breasts. Josie knew she was naked underneath. He could not wait to join her. He climbed onto the bed and Mistress unraveled the sheet and allowed Josie inside the warm cocoon. Josie gave Mistress a kiss on the lips. It turned into a long sensual kiss that made Josie's cock throb even harder.

Mistress playfully grabbed his cock. "Somebody's excited to see me. Don't you ever put this thing away," she teased.

"I can't help it. You make me feel this way," confessed Josie.

"Good girl," complimented Mistress Sarah.

Julie was in the bed also. Her arm draped over the side of Mistress Sarah. She was still asleep, exhausted from the night's events. She was in her own dreamy world but her presence alone added to the excitement for Josie. He was thrilled once again to share a bed with two beautiful girls. Life couldn't get better he thought.

Mistress Sarah made Josie turn over so that his back was to her in a spooning position. The warmth of the covers and the heat of Mistress Sarah's naked body pressed against his back were comforting. She slid up his night gown and slowly stroked his cock. Her strokes were long and steady like she was petting a kitty. Josie was growing fond of these 'stroking' sessions with Mistress Sarah. In his sleepy state they soothed him. He was her kitten and he purred inside.

Josie drifted in and out of sleep while Mistress petted him. His cock remained hard, his arousal level held at a steady soothing level. He was enjoying this comatose state of mind when suddenly it occurred to him that it was his last day with Mistress Sarah. He would be heading home later in the day. The thought was depressing.

Josie sulked quietly in his girly voice, "I can't believe I have to go home today."

"Why is that kitten?"

"I've just had so much fun with you these last few days. I can't believe it's over already."

"Mmmm," purred Mistress Sarah. She gave his cock a nice firm squeeze. "It has been fun. Once you let the girl in you run free, you discovered a whole new world didn't you princess?"

Josie hadn't really thought of it as letting the girl inside him free, but Mistress Sarah was right. That's really what the weekend had been all about. He truly was falling in love with all the feminine things that the girls had helped him discover. 

Josie thought out loud to Mistress Sarah, "Yes Mistress, it has been fun dressing in sexy clothes and hanging out with you and your friends. I just wish it didn't have to stop."

"It does not have to stop sweetie. I want you to continue to wear all these pretty things. You'll have to buy your own wig and continue to practice putting on your make-up."

Josie thought about what Mistress Sarah was saying. He responded, "Mistress, I want to do all those things. I just can't imagine doing them at home without you. At home I would be laughed at and teased. I would be so embarrassed."

"Kitten, there is nothing to be embarrassed about. Be a proud sissy. You have discovered an exciting part of you that is now free. Think of how much more fun you have had as a sissy. Much more fun that you had as a boring man, don't you think?"

Mistress Sarah skillfully changed the pace of her strokes. Josie barely noticed the lighter more teasing strokes. He was unaware that his arousal level was slowly rising until a quick charge of arousal hit him and caused his whole body to tense at the unexpected rush. His mind was already drifting into a blank subspace.

Josie was becoming more accepting of being referred to as sissy, but the term still caused him to twinge slightly with embarrassment. He thought about the last two days and how thrilling they were. He had been with four beautiful women and had the most thrilling sexual experiences of his life. If that's what it meant to be a sissy, well then Mistress Sarah was right -- being a sissy was much better than being a man. He just had to learn to accept it. 

Josie admitted to Sarah, "Yes, this weekend was by far the best weekend of my life. It's just so different with you Mistress. When I am here with you, it's like another world. You and your friends are accepting of me as a sissy. You make me want to be pretty and sexy and girly."

Mistress Sarah was pleased with what she was hearing. There was just a very thin thread holding him onto his past male world. She encouraged him, "You are pretty and sexy Josie." 

Mistress Sarah let Josie ponder those words silently. She continued to stroke his cock. She was keenly aware that her light teasing strokes were driving him crazy and bringing him to the edge. Josie was beginning to lightly thrust his cock into her hand in an effort to feel more pleasure. She was delighted at these futile attempts. 

Everything that was happening seemed spur of the moment to Josie but Mistress Sarah was not doing things completely off the cuff. She had her own specific intentions. She knew that her teasing was putting him into a weak state of mind. Pleasure was affecting his ability to think and making him completely open to her suggestions. She was leading the conversation to a very important decision for Josie. She was ready to sever the thread.

When she felt Josie's cock twitch and his body shudder with pleasure, she licked his ear and seductively sucked on his lobe and whispered, "It doesn't have to change Josie."

"What do you mean," asked Josie wondering what miracle solution she had.

Mistress Sarah tugged on his arm and made Josie lie on his back on the bed. By now Julie was awake. When she was in her semi-sleep state she was picking up bits and pieces of their conversation. It didn't take long for Julie's instincts to sense that Mistress Sarah was in tigress mode, which meant that she wanted something from Josie. 

Julie had experienced this once before with another guy. It was thrilling to watch how Mistress Sarah conquered others with her feminine seduction and power. Not wanting to miss the excitement, Julie lay quietly on the bed next to Mistress Sarah and listened intently.

Mistress Sarah lay on her side, along side Josie. Her full breasts were on display for Josie. Her beautiful face was only inches from his. Josie stared into her eyes and melted even more. She was sexy and hypnotic.

Mistress Sarah teased his cock until the point where his breaths became deeper and the pleasure caused his eyes to close so that he could take in the bliss and concentrate on not cumming. Through half open eyes he could see Mistress Sarah's tongue slowly lick around her lips like he was a tasty treat. Then she explained her plan in a slow and seductive manner.

"Well Josie, you don't have to leave sweetie." Mistress licked his ear lobe and slowly teased the tip of his cock. "You are part of my family now. You belong to me and so you have a place in my house."

Josie opened his mouth but before any words could escape Mistress Sarah put a finger to his lips and shushed him. "Shhhh princess. Just listen to me." Her other hand continued to tease his cock. "Mmmm. Your 'clittie' is so hard (giggles). I can tell you really like this. You really want it." Josie closed his mouth and sunk deeper into a thoughtless haze.

Mistress Sarah continued to explain. "Think about how exciting it will be to serve May and me every day...." Josie watched the tip of her tongue peak out and seductively glide across the bottom of her upper lip. "..pampering us and pleasing us. Playing dress up and always wearing sexy things for me. You are our slave, our maid and mmmmm, our sex toy. Just imagine how much fun it will be licking my pussy day in and day out - your lips against my lips..." Mistress Sarah let out muffled giggle.

Josie liked the mental picture she was painting. It was making him hotter and hornier by the second. It was definitely something he had fantasized about over and over again. It was hard to fathom that it could be real. To leave behind his job and friends on a whim was monumental and would seem foolish to any rational thinking person. As crazy of an idea as it was, Josie found himself considering it and wondering if he could really do it. Josie was so deep in arousal that he could barely talk. He whispered, "I like the sound of that Mistress." 

"Mmmm. You will make a good pet around the house kitten."

"What about my job," questioned Josie, forcing himself to try and be rational despite the onslaught of pleasure.

Mistress Sarah licked her lips again and stared into his eyes. Josie's mind grew softer, weaker, and more obedient as he gazed at her wet lips and hypnotic eyes. "Pretty pet, the only job you need to worry about is pleasing May and me. I will take care of you princess. Nellie has a partnership in his company and supports me financially so you don't have to worry about that. You're existence will simply be about serving us. Exciting thought, isn't it?"

It was an exciting thought. "Yes, it would be a dream come true, but what about my family and friends?"

Mistress Sarah corrected him, "It is a dream come true pet," she said, emphasizing the word 'is'. "It is happening to you lover. There's no turning back now. I know it's what you what. You can still visit your friends and family. Just tell them you met the love of your life and are moving to be with her."

"but my parents would have a hear attack seeing me as Josie."

"Oh Josie, don't worry about that." Mistress Sarah laughed and gave him a motherly kiss on his forehead. "That silly boy Joe is still a part of you. He's just tucked down deep inside. When you visit your family you can put on those boring boy clothes and pretend to be a boy. It really is a silly costume for you Josie but if that's what your friends and family want to see, then that's fine with me. I might even let Joe play with me every now and then. Often times I get the urge to be fucked good and hard. Mmmm. I'm thinking I need a good fucking soon...maybe tomorrow. You wouldn't want to miss that would you Josie?"

"no, I'd want to be there for that," answered Josie quickly. His cock throbbed.

"Your clittie is so hard Josie," exclaimed Mistress Sarah. "You want this. I know it."

Josie faced a fierce determination in Mistress Sarah that was unbeatable. The more he talked with her the more he wanted to be with her and obey her. The images she was painting in his mind and the continued teasing of his cock put him in a highly aroused state, making it hard for him to continue talking. He was losing any bit of control that existed.

He admitted, "I can barely think Mistress Sarah. You are making me feel so good. I want to cum so bad."

Mistress Sarah nibbled his ear. "I know sweetie. You don't need to think. Slaves don't think. They just do what I want."

"Yes Mistress," agreed Josie.

Mistress Sarah's voice changed from sweet and seductive to a firm and commanding tone. "This is a big decision Josie. I know you want it to happen but you do not have to commit to it just yet. Here is what you are going to do." 

Mistress Sarah stopped stroking his cock. Instead she grasped his cock firmly and held it in the palm of her hand as she talked. "You are going to spend a few more days with me. I have more training to do with you. You can not be left unattended right now or you'll go back to your silly boyish ways."

"Yes Mistress," agreed Josie without hesitation. 

Mistress Sarah's firm grasp on his cock was driving him crazy. The warm tightness around his cock felt incredible. He was overly aroused from all the teasing and his natural instincts were telling him to thrust against her hand but he knew that the slightest movement would send him over the edge. It took all his will power to remain still. He was teetering on the edge of erotic bliss. The urge to cum was so powerful that he wished he could stop being submissive, lose all inhibitions and just fuck with wild abandon. It was an intense mental struggle to stay still but the domination and control that Mistress Sarah instilled in him was strong and he remained at her mercy. 

Mistress Sarah continued with her demands, "You are going to call your work this morning and tell them you will be out until at least Wednesday because you have personal matters to take care of."

"Yes Mistress." Josie was mindless now. He simply agreed with everything.

"Then you are going to cook us a nice breakfast. May and Mill are about the house somewhere so make enough for them. Those cute little sluts are going to be hungry after all the fucking last night."

"Yes Mistress."

"While we eat breakfast you are going to write in your sissy journal about how much fun you had being a girl last night and about how you can't wait to move in with me."

"Yes Mistress."

"That's enough for now pet." Mistress released his cock. She slapped it playfully and said, "Put this away now. Find some panties to hold it in its proper place."

The slap to his cock almost sent him into an orgasm. "Please can I orgasm Mistress," pleaded Josie.

Mistress Sarah laughed, "No slave. You have things to do. Maybe once you make the final commitment to stay, I'll let you cum."

Desperately Josie exclaimed, "I'll stay Mistress! I want to move in with you and be your permanent slave." 

Josie was a little shocked at the words that came out of his mouth. In a move that was worthy of publishing in 'Reverse Psychology Today,' Mistress Sarah said, "Silly girl, you are just saying that because you want to cum. It wouldn't be fair for me to accept that."

She gave his butt a slap. "Now go and do your tasks. Calm yourself down."

Mistress Sarah's rejection made him want to cum even more. It fueled his desire for her and his desire to live with her. His eyes looked at her pleadingly. She slapped him again and ordered him out of the bed. "Get to work slave."

"Yes Mistress," sulked Josie. Ho got out of bed. His cock stood straight up against his silk night gown.

"Put that silly thing away," scolded Mistress Sarah.

Julie's pretty eyed peered over the side of Mistress Sarah. "It looks so vulgar," she commented in a sleepy voice.

Mistress Sarah smiled at Julie adoringly and petted her long black hair. "Ahhh, good morning pet. My pussy is dripping from all the excitement. Come attend to it."

Josie's watched Julie crawl over top Mistress Sarah's pussy. Her head dipped down and her tongue disappeared into Mistress Sarah's wet folds. Mistress Sarah let out a satisfying moan. Josie's cock throbbed, wanting to be a part of the excitement. He was pondering the idea of sliding back into bed with the girls. Mistress Sarah did not give him the chance. She shooed him away. Sternly she said "Run along Josie before I have to punish you."

Julie's head bobbed up and she looked at him with a devilish smile. Mistress Sarah pushed her head down to her pussy and moaned, "Don't stop pet. I'm close to cumming."

Against his will, Josie walked out of the room. He was jealous that Julie got to pleasure Mistress Sarah and Jealous that Mistress Sarah was going to have an orgasm. On the other hand, his cock was raging hard and dripping. He was thrilled to be denied and at the mercy of Mistress Sarah's control.

Even though Mistress Sarah had wanted him to stay for just a few more days, Josie decided to take the whole week off. He figured he would need a few days to recover. After he made the call to his work he headed to the kitchen to prepare breakfast.

The girls came down in pairs as the smell of bacon and eggs wafted through the house. First it was May and Mill. They both laughed at his erection. When Mistress Sarah and Julie ventured in, Mistress Sarah immediately scolded, "I thought I told you to put that thing away."

"Sorry Mistress. I can't help it. I'm super horny."

"I'll take care of it," announced May. She was in a playfully cruel mood. "Come over here Josie," she ordered.

May had Josie bend over and place his hands on the kitchen table. Then she took a wide spatula and started whacking his ass with it. All the girls were sitting around the table giggling as May whipped his ass. May took great pleasure in seeing Josie's body flinch with each swat of the spatula.

"Come on Josie, calm down," she demanded. "We're trying to eat here."

The girls giggled. May announced to everyone, "His ass is getting nice and red." Then she looked over at Julie and ordered, "Go get some ice Julie. Help me get rid of that nasty boy hard-on."

Within seconds, Julie was kneeling by the table and pressing ice cubes into Josie's balls. Josie moaned in discomfort at the sudden coldness on his hot balls. May responded to his groan, "That's right bitch-boy. I brought the heat and Julie has the ice. Fire and ice. Feel it bitch boy."

Being assaulted on both ends was extremely effective in extinguishing his arousal. Josie's cock shrunk and shriveled. Mill was the first to comment on it. Mockingly she said "Awww. His cock is all soft. What's the matter sissy, you don't like your whipping? You don't like having your balls iced?"

"Hold your clittie into place bitch," ordered May. "That's it bitch. Now Julie, pull up her panties. Hold that clittie in place."

Julie pulled the panties nice and snug around Josie's waist. The tight panties held his bent cock between his legs. Julie rubbed her hand between his legs, along the underside of his cock. Then she declared, "Her pussy is all ready."

"Very good," said May. She gave Josie's panty covered ass one last swat just for fun. May threw the spatula onto the table in front of Josie. "Now serve us our breakfast slave," she demanded as she joined the rest of the laughing girls at the table.

"Yes Miss May," responded Josie immediately. "Thank you for helping me," he said as he stood up.

Mistress Sarah leaned over to May and gave her a kiss on the cheek and complimented her. "Well done pet." 

Josie happily served the girls breakfast. Once all the eggs were served and drinks were poured, he stood at attention alongside the table, awaiting any requests or orders. The girls enjoyed their food and talked amongst themselves. Josie looked around the table and could not think of a better way to spend the morning. It was thrilling to serve four beautiful women and be able to admire them in their lingerie and pajamas. He felt lucky. The idea of moving in with Mistress Sarah was growing on him, even if it meant leaving his job and uprooting his current life.

Sunday turned into a lazy day. Julie headed off to the airport to return to NY. She had a modeling gig first thing Monday morning and needed to be back early so that she could rest and look refreshed on Monday. After Julie left, Sarah and Mill decided to hang out at the pool. Josie helped them into their bikinis. Mistress Sarah wore a plain white bikini but she looked far from plain in it. Her large firm breasts were barely contained in the small bikini top and her ass look incredible in the soft stretchy bottom. Josie knew she would be the center of attention at the pool.

Miss May wore an emerald green bikini with a stylish wavy like top. Josie thought the green color looked beautiful against her tanned skin. The bikini showed off her slender body and sexy hips when she walked. Since it was a pool day for the girls, Mistress Sarah insisted that Josie also be dressed in a bikini. She helped him into a pink metallic thong bikini. The bikini was decorated with a pink flower at his crotch and one on each breast. His cock was tucked back into its clittie position and breast forms were pushed into the skimpy top to give him real looking breasts. Mistress Sarah also made him put on the blond wig that he wore to the night club. She touched his face up with foundation, eyeliner, and pink glossy lipstick.




Discovering Mistress Sarah's World Pt. 07



Mistress Sarah made Josie slowly turn for her and Miss May. She admired her thong clad pet. The shiny metallic top and pink lipstick were a bright and fun combination. Mistress Sarah complimented, "Mmmmm. You look so sexy Josie."

When his ass was facing the girls, Miss May laughed at how the small v-back thong barely contained his large clittie. Miss May commented, "Be careful how you lay down princess. The boys might get all excited if they see your clittie hanging out like that."

Josie blushed. Being in a bikini was a new experience for him. He started to feel that strange excitement that he felt the first time Mistress Sarah had him slide on panties. This was another facet to his new feminine life that Mistress Sarah and Miss May were forcing him into.

Mistress Sarah had Josie put on a pair of clear heels. When Josie stepped into them Miss May rubbed his ass and said, "Your a beach bombshell."

"Thank You," replied Josie. He felt a bit self-conscious and vulnerable in the skimpy outfit. Her compliment helped put him at ease.

Mistress Sarah grabbed her pool bag. "Ready to go girls," she asked.

Josie looked at her with a panicked expression. "Do I have to go to he asked?"

"Of course princess, it's girls day at the pool."

"Please can I stay here Mistress. Please!" Josie begged desperately. "I will be so embarrassed."

"Don't be silly," said Miss May. "You have a beautiful figure."

"But my outfit is so skimpy. Everyone will know I am a man dressed in a bikini."

Both girls laughed. "Oh Josie," said Mistress Sarah in dramatic and mocking tone. "There is nothing manly about you. You are my girl now. They may think you are a sissy but certainly not a man."

Josie blushed. He was just about to resign himself to the embarrassing fate, when Mistress Sarah said, "You can stay behind sissy but you must stay in your bikini and heels and I expect you to make lots of appearances out on the balcony. May and I will situate ourselves so that we have a good view of the balcony."

May smacked his ass and said, "That's right sissy-bitch. You need to strut your slutty little tush for us."

"Yes. Mistress. I will do that. Thank you," replied Josie in a happy and relieved tone. It would still be embarrassing for him but it was much better than walking down to the pool in a bikini.

"Clean up while we are out sissy-maid. I want every room sparkling clean when we return or you'll get a nice hard spanking."

Mistress then grabbed Josie's wrist and led him out onto the balcony. The pool was quite a distance from where they were at. "Wait here and look for us Josie." She handed him his cell phone. Keep this handy princess. We'll be calling your frequently with instructions and tasks to do." 

Josie waited on the balcony until he saw the girls take their seats at the pool. Once situated, they both turned and waved at him. Josie wave back. His phone vibrated and looked down to see a text from Miss May. It read, "Get to work maid." 

Josie went to work cleaning the house while the girls relaxed at the pool. True to her word, Mistress Sarah called him every now and then and ordered him out onto the balcony. She would make him wave and shake his body and wiggle his ass. With Mistress Sarah and May looking his way and laughing, there were always a few people at the pool who would look over to see what was going on. Josie was conscious of this and was a bit embarrassed. He took some comfort in knowing that from the far distance no one would recognize him or even guess that he was guy. 

On one particular instance, two guys were talking with the girls when Mistress Sarah called. She ordered Josie to flash her tits and wiggle them for the guys. This was a bit tricky since he was wearing falsies. Josie managed to pull his bikini top to the side and hold the falsies in place while he jiggled them. He could see the guys at the pool raise their hands and cheer. 

"Good girl," said Mistress Sarah. "Now shake your ass for the boys like a whore." Josie turned and wiggled his ass.

"That's it slut. The boys are loving the show. Maybe I'll invite them up later for some fun Josie. What do you think? "

Nervously Josie responded, "uh...I don't know if I'm ready for that Mistress."

"It's all fantasy right Josie. Just say yes," demanded Mistress Sarah..

"Yes Mistress." Josie's cock swelled in his bikini bottom, knowing that she was exerting her power to make him admit humiliating things.

"Yes what," asked Mistress coyly.

"Yes, I would like it if you invited the boys up for some fun later."

"Mmm that's nice Josie. You would suck their cocks wouldn't you?"

Josie was blushing. He knew the answer that Mistress expected. "Yes Mistress. I would suck their cocks." Josie wondered how much of the conversation the guys could hear. He imagined they were getting excited, thinking that a girl was going to give them a blow job. He hoped Mistress Sarah was just teasing them and him.

"You're a whore Josie." Mistress Sarah giggled. "Get back to work."

That was the last call Josie received. When Mistress Sarah and May returned Josie was relieved to see that no one else was with them. May squeezed Josie's ass when she walked in and said, "Nice job slut. You had those guys all excited. Your training has definitely paid off. Pretty soon you won't even remember what it's like to be a guy."

Josie wondered how true that statement was. In the back of his mind he was still pondering whether or not he should move in with Mistress Sarah permanently. She was amazing, beautiful, and fun. Not to mention all the fun he would have serving Miss May, Mill, and Mistress Sarah's other friends. What made him nervous was his feminine transformation. It was fun and exciting, but totally losing his manliness scared him. He was very confused and unsure whether or not his infatuation with Mistress Sarah would win out over his fear of losing his manhood.

Mistress Sarah was not confused at all. There was no doubt in her mind that the only reason Josie would be leaving in a few days, would be to pack up his belongings and move in with her. She had already determined that she wanted him as her 24/7 slave and fuck toy. She knew that he was weak and could not resist her. It was just a fun game for her now. She would toy with him and tease him and play all sorts of mind games with him and finally get him to beg to stay with her. In fact she had many things planned over the next few days that would break all his limits and transform him into a complete slut and slave for her. She had always wanted a blank mindless fuck toy to play with. It would only be a matter of time before Josie would fit that bill for her.

Mistress put her first mind game into motion. "Josie, sweetie, I want you to take my laptop out onto the patio and type up your resignation letter."

Josie's heart pounded and he looked at her a bit shocked at the request. Mistress Sarah responded to his expression, "It's just an exercise princess. I know you haven't decided just yet, but I want you to write the letter anyway. See what it feels like to get it on paper, o.k.?"

"Yes, Mistress," 

"Good girl. May and I are going to take a shower. You can show it to me when you are done."

Josie sat at a round metal table on the balcony and typed away. The small overhang on the balcony provided little cover from the hot sun. He was glad to be only in a bikini. 

Ever since Mistress Sarah had brought up the idea of him moving in with her, Josie had been going back and forth in his mind, debating whether or not he could really do it. Now as he wrote the letter it made him think even harder about it. He wrote the letter very general with sentences like "It's been a pleasure working here' and 'For personal reasons I am leaving."

When he finished writing it, he printed it. Before he could get up to get the letter, Mistress Sarah walked out onto the balcony wrapped in a fluffy white towel. Her hair was also wrapped in a small towel. Josie thought she looked sexy even in just towels. In her hand was Josie's letter that she retrieved from the printer. She was reading it while she walked onto the balcony. It was very brief so it only took a few seconds to read.

"Lovely letter Josie," complimented Mistress Sarah. She placed it on the table with a pen. "Now sign it," she demanded.

Josie looked up at her. Her look was unwavering. "Yes Mistress." He took the pen and signed it with his real name. He couldn't help but think that he was actually signing away his life at that moment. It was a scary but exciting feeling.

"That name looks so silly now doesn't it Josie. It might be the last time you sign it sweetie," laughed Mistress Sarah. "Now imagine that this was for real. How does it feel Josie? How does it feel to not have a job and to be 100% committed to serving me?"

Josie knew the Mistress Sarah was mentally manipulating him. He could feel her power and determination to control him and it excited him. His cock swelled in its bent position in his bikini bottom. He could feel the heat of his cock against his thighs. The thin thong string barely held it in.

"It is exciting Mistress. A little scary but very exciting," he admitted.

Mistress Sarah had him stand up. Then she pulled his bikini bottom down just enough that his cock came free. It instantly swelled into a fully hardened state. Mistress Sarah giggled. "That's was I thought."

She held his hard cock firmly in his hand and said, "Now, just for fun Josie, write me another resignation letter. This time tell the truth. Write how you met a Mistress and how it changed your life and that you realize your new calling in life is to worship the female and serve a Supreme Goddess."

Mistress Sarah raised her finger to Josie's lips. It was covered in his precum. Josie sucked on her finger. Mistress Sarah whispered, "Mmm....you are excited by this new world of yours, aren't you?"

"Yes Mistress," replied Josie.

Mistress Sarah giggled. "Get to work Josie. This next letter will make a nice addition to your sissy journal."

The second letter took longer to write. With his cock free, Josie could not help but stroke his cock while he wrote his resignation letter and about his new life. He could not believe how excited he was getting from imagining serving Mistress Sarah as a full time slave. At one point he got so excited and aroused that he had to stop writing, stop stroking his cock and he had to concentrate on not cumming. He was close to the edge but he managed to calm himself down.

This time when Mistress Sarah walked onto the balcony with his letter she had on a simple summer dress. Josie immediately admitted, "I am so horny Mistress. My clitty is aching."

"Your horniness is evident in this letter. It is very long and detailed."

Mistress Sarah handed him the letter and pen again. Josie signed it. Mistress Sarah leaned down and kissed him on the cheek. She squeezed his hard cock and said, "Look how hard and wet your clittie is. I think you want this more than me Josie."

"I do," admitted Josie. 

"Then it's settled. The only question now is which letter do I send to your boss?"

"You can't send the last one Mistress. I will be so embarrassed!"

"But it is the truth princess. Besides, you will be leaving your job. Who cares what your boss thinks."

"Please, no," pleaded Josie. "I don't want them to know about this part of my life."

Mistress Sarah laughed. Her laughter was filled with arrogance and dominance. "You are a weak little slut Josie. You still have a few more days here before I send you on your way to pack all your things up. Be a perfect little princess for me for the next few days and maybe...just maybe I'll let you hand in the first letter."

"Thank you Mistress. I will be a good princess. I promise."

"Gather up your things now slave. It's time for you to get a shower." Mistress Sarah walked off the balcony with both his resignation letters and a smile of success.

Josie's heart was pounding. Everything happened so quickly. He felt weak and helpless in Mistress Sarah's presence. She had a power over him that he could not explain or resist. He was now a permanent slave to Mistress Sarah. His cock was harder than ever as he thought about it. He wanted to desperately cum.

Inside, the girls had a good laugh when Josie stripped for them. "Josie darling, you've developed sexy tan lines," giggled Miss May. "Now there is no denying that you are sissy girl.

Josie looked down and sure enough there were two small white triangles on his chest. The little bit of time he spend out on the balcony in the sun was enough to give him a bronzed tan. The tan lines from the bikini bottom were less noticeable as his lower body was hidden from the sun most of the time.

"Turn around and let me see your ass." Demanded Miss May. She gave it a good hard squeeze. "Nice ass Josie but no tan lines. We'll have to work on that."

Mistress Sarah added, "by the time you leave, I want you to have a dark tan with clearly visible tan lines. Do it or I will send in your naughty resignation letter."

"Yes Mistress," said Josie. He knew he did not have a choice.

CHAPTER 19 Introducing Neil

It was only his third morning awaking at Mistress Sarah's house but it was already feeling like a ritual to Josie. He awoke in a silk gown with a raging hard-on and completely aroused just like the other mornings. And just like the other mornings he could not wait to crawl into bed with Mistress Sarah and Miss May. 

Josie crawled to the foot of the door and discovered a note and lingerie waiting for him. The note read,

 'Sexy lingerie for a sexy pet. Put it on and come join us.'

Josie held up the delicate items. It was a matching bra and panty set along with black stockings. The bra was purple and adorned with ruffle lace and a purple satin bow. The panty was mesh at the top. The crotch area was similar to the bra, adorned with ruffle lace and a satin bow. Garter straps were built into the panty. 

Josie thought the set was super sexy and could not wait to put it on. He quickly changed into the items. He felt feminine and sexy in the soft lingerie. His 'clittie' was fully aroused and almost dripping. The black heels he wore Saturday night were also sitting by the door. He strapped on the heels and crawled into the room.

Josie was excited to hear moans and see movement on the bed. He could not wait to join the fun. He remembered Mistress Sarah saying the day before that she was in the mood for a good hard fucking. Josie hoped this would be his lucky moment. His clittie throbbed even harder at the thought. 'Perfect timing' he was thinking but then he noticed one of the moans was a bit deeper than usual. 

Josie froze when he realized that Miss May was not the other person in the bed. It was a man, which Josie presumed was Mistress Sarah's live-in slave and boyfriend, Neil. Wanting to retreat, Josie quietly turned to leave but it was too late. Mistress Sarah had noticed him.

"There's my pretty pet," she exclaimed happily. "Come on over kitten. Come meet Neil."

Josie crawled slowly. Mistress Sarah encouraged him on. "Don't be shy kitten. Come over here."

Both Mistress Sarah and Neil sat-up in bed. They were naked but covered from the waist down by the bed sheets. When Josie was at the side of the bed he sat up on his knees. Mistress Sarah did a quick introduction. "Neil meet Josie. Josie meet Neil." 

The introduction was hardly necessary. They had never met in person but both knew each other through the many online exchanges they had together with Mistress Sarah.

"Nice to finally meet you," said Neil in a bold tone.

Josie replied, "hello," in a much meeker tone. He suddenly felt silly and awkward using his feminine voice in front of a man. 

"Do you like your new lingerie," asked Mistress. "It fits you well."

"Yes. Thank you. It is very sexy." Josie liked the lingerie but felt embarrassed in front of Neil.

This was not how he expected things. He had always imagined himself one-step above Neil in Mistress Sarah's hierarchy. After all, Neil was feminized long before Josie. When they were on-line Mistress Sarah often let Josie be dominant to Neil. Neil had even referred to him as 'Master' on occasions. Now the tables were turned. Josie was feminized and kneeling before Neil. Josie was at the very bottom of the submissive hierarchy.

"Turn around kitten, so we can see you from all sides," ordered Mistress Sarah.

Josie slowly turned on his knees. When his back was to them, Mistress Sarah commented to Neil, "Doesn't she have a cute little ass. She will make a good pet and slave for us, don't you think?"

Neil replied, "Yes, she is sexy. She will be a great addition to the family."

Mistress Sarah made Josie turn to the front again and then she said, "Very nice pet. You should thank Neil for the lingerie. He is the one who picked it out and bought it for you."

Josie blushed and was embarrassed to know that he was wearing lingerie that a man had bought him. "Thank you," he said meekly. 

Josie had noticed how Mistress said 'our pet' to Neil, implying that he was not only a pet and slave to Mistress Sarah but also to Neil. He was also keenly aware that Neil was referring to him as 'she'. Having another man disregard his manhood brought on a new level of embarrassment to Josie. Josie felt incredibly submissive and inferior kneeling before Mistress Sarah and Neil. It was a strange and awkward feeling.

He also knew that Mistress Sarah was enjoying the moment and getting off on putting him in this unexpected and awkward predicament. He could see the devilish pleasure in her eyes and this excited him. Despite his embarrassment, his cock was aching hard. 

"You are just in time princess. Neil was about to fuck me. Now you can watch."

Josie's heart dropped with disappointment, "but I thought I was going to fuck you," he said dejected.

Mistress Sarah laughed dramatically, highlighting how absurd Josie's statement was to her. "Oh Josie. Josie, Josie, Josie. You didn't think I meant you would get to fuck me, did you?" She laughed again. "Look at yourself princess. You're wearing panties and a bra. You even have heels on. You're much too soft and pretty. I'm in the mood for a hard fucking from a real man, not a prissy little sissy girl.'

Mistress Sarah pulled the sheet down from Neil's waist and made him get up on his knees so that Josie could see his cock. His cock was in a semi-hard state. Mistress Sarah started to stroke it. While she stroked she said, "This is a real cock Josie. See how he has control. He can sit next to me without being erect. He's not weak like you, walking around with a hard clittie all day."

Josie felt even more submissive and in the twisted world that he was now a part of, he was enjoying Mistress Sarah's humiliating words. She was right, that he was weak. He did not know how Neil could not be hard sitting next to Mistress Sarah in bed.

Neil's cock finally grew hard in her hands. Mistress Sarah commented, "Look how big his cock his Josie. Isn't that a nice big cock?"

"Yes," replied Josie.

"Maybe if you are a good girl, I'll let you suck it. You will be a good girl for me, won't you kitten?"

"Yes, I will be a good girl for you." Josie felt as if his answer to that question implied that he wanted to suck Neil's cock. Josie did not want to suck a man's cock but he was in awe at how Mistress Sarah masterfully manipulated the conversation in that direction.

"Pull out Joe's cock for me princess. Stroke your man's cock while I stroke Neil's."

Josie lowered his panties and started stroking his cock. He was excited that Mistress Sarah was going to play the mind game with him of stroking a man's cock. 

"That's it Josie. Let's stroke these boys cocks together."

Josie slowly stroked his cock in the same rhythm that Mistress Sarah was stroking Neil's.




Discovering Mistress Sarah's World Pt. 07



"Look down at what you are stroking Josie. Whose cock are you stroking?"

"I am stroking Joe's cock."

"My pussy is getting wet from playing with Neil's cock. Are you getting aroused too Josie."

"Yes Mistress."

"Tell me more."

Josie knew he could not get off that easy. He had played this game once before and he knew what Mistress wanted to hear. "I am getting aroused from stroking Joe's cock. His hard cock feels good."

"That's it Josie. Watch me stroke Neil's cock. You stroke in the same rhythm."

Josie felt as if he were watching a porno as he stared at Mistress Sarah's hand gracefully sliding up and down Neil's cock. He stroked his own 'man's' cock in the same rhythm.

"Whose cock do you think is bigger," asked Mistress Sarah.

"I don't know," replied Josie with little thought.

"Look at Joe's cock and look at Neil's. Whose is bigger?"

Josie stared at each cock. Both were decent in size. Neil's seemed to be a bit bigger. "I think Neil's is bigger," he admitted.

"Yes, me too Josie." Mistress Sarah held Neil's cock and said, "I want to be fucked by a big cock right now so this is the cock that's going to fuck me. Put Joe's cock away now and watch how a real man fucks."

Josie pulled up his panties, disappointed that he had to stop stroking his man cock. Neil wasted no time going into action. In a blink of an eye he was on top of Mistress Sarah. Josie watched his cock penetrate Mistress Sarah's cleanly shaven pussy. On the first thrust, Neil's cock was instantly covered in her wet juices. Josie could see his cock getting wetter and wetter each time he thrust into his Mistress's hot sex.

Mistress Sarah's body was hot with pleasure. The fullness of Neil's cock inside her was a special delight. She looked to the side and was pleased to see Josie kneeling and watching her be fucked. He looked sexy and submissive kneeling in bra, panties, stockings, and heels. The purple ruffles and lace looked incredibly pretty and sexy adorning his muscular body. She could see his cock straining against the tight panties. She knew he was desperate to cum and she took great pleasure in knowing that he was holding back all because of her power over him.

"That's right Josie. Watch your Mistress get fucked. It's something Joe will never do..at least not in the near future. Play with your clittie," demanded Mistress Sarah.

Josie started to stroke his cock. "What are your doing," asked Mistress Sarah in a disapproving tone. "I said play with your clittie, not Joe's cock. You're a lady remember? Rub it with two fingers like I taught you."

"Sorry Mistress." Josie rubbed two fingers up and down the underside of his 'clittie'. The two finger rubbing proved to be very torturous for Josie. He was so horny and aroused that he just wanted to grab his cock and stroke it hard until he had an explosive orgasm. Instead he was forced to rub his cock on one side, which resulted in a steady light tease that kept him on the edge. It took all his will power to maintain a steady rubbing and hold back an orgasm.

"Good girl," complimented Mistress Sarah. The pleasure from Neil's fucking was multiplying inside Mistress Sarah, causing her speech to become breathy. She spread her legs wider and moaned "Mmm...Josie..this feels so good."

Josie's arousal peaked as he took in the primal scene before him. Being there in person and hearing the raw moans and sounds of sex was far more exciting than watching the same scene in a porno. He begged to Mistress, "I want to cum Mistress. I don't think I can hold back. Please can I cum!"

Josie's desperate pleas added to Mistress Sarah's bliss. She could see the tip of his cock peeking out of the pretty panties, covered in sticky pre-cum. His fingers were glistening with the wetness. A pleasurable and devilish smile filled her face. "No. Suffer for me slave," she demanded. Then she moaned loudly and ordered Neil to cum inside her. 

Josie was both jealous and excited from watching Mistress Sarah and Neil erupt together in a frenzy of fucking and orgasms. He was so aroused that he had to stop stroking his 'clittie' to keep himself from cumming.

Immediately after her orgasm ended, Mistress Sarah transformed into a possessed demon. She pushed Neil off her and ordered Josie onto his back. Before he was even into position, Mistress Sarah was on top of him, pushing his head back onto the floor. She straddled his face with her pussy.

"Lick my pussy," she ordered like a drill sergeant. Without hesitation Josie buried his tongue into her wet creamy pussy. "That's it slut. Get your tongue deep in there. Lick out Neil's cum. I know you want it. Lick it up cum slut."

There was no time to think. Mistress Sarah was barking out commands and smothering his face with her pussy. She even grabbed his hair and pulled his face into her, smothering him more. Josie licked as hard and deep as he could but in her demonic state, Mistress was not satisfied.

"Lick harder slut! Get inside of me bitch! Clean out my pussy. Lick up all that cum sissy slut."

Josie did all he could to please her. He licked her wetness and the creamy cum inside her pussy. She was feeding him his first ever cream pie right in front of Neil and there was nothing he could do about it. He could barely breathe but he licked like there was no tomorrow because all he cared about with pleasing Mistress. He was in a mindless obedient state-of-mind.

"Get used to this sissy," barked Mistress Sarah. "This is your life now -- licking Neil's cum out of pussy every time he fucks me. You want this, right?"

Josie was smothered in her pussy to and too busy licking to answer, which did not please Mistress Sarah.

"Answer me slut! Say it into my pussy," demanded Mistress Sarah.

"Yes, I want this," said Josie. His words were muffled and barely audible from being smothered.

"Louder bitch!"

Josie repeated the words. Mistress Sarah pushed his head harder against her pussy. "That's right slut, and if May or Mill bring home guys you are going to clean out their pussies too. You are going to be the house cum cleaner, isn't that right?"

Josie yelled into her pussy again, "Yes Mistress!" 

"I own you slut, don't I," yelled Mistress Sarah as she grinded her pussy over his mouth and nose."

"Yes Mistress."

"And if I own you, then I own all your possessions and all your money. It's all mine slave! I will take what I want. Every dollar that you earn is mine. From now on, you exist just to serve me, got it?"

"Yes Mistress."

Mistress Sarah continued to ride Josie's face for the next five minutes, ordering him to lick deeper and continuing to verbally assault him about how she owned him and how he was a sissy that would do anything she wanted. It was a darker and crueler side of Mistress Sarah that Josie had never experienced but he loved it. He loved feeling helpless and completely controlled and owned by her.

When Mistress Sarah was finished having fun with Josie, she sent him off to get cleaned up. He washed off in a scented bubble-bath, shaved his legs and face, and put the lingerie from Neil back on. In another room Mistress Sarah laid out his clothes for the day. It was a simple outfit that consisted of tight clingy leggings pants and an oversized brown cotton shirt. Jose made sure to tuck his clittie back so that the tight pants did not reveal anything manly about him. Once dressed, Josie put on his make-up, wig, and heels, along with some costume jewelry that Mistress Sarah picked out.

Mistress Sarah was pleased with the look. She commented on how the leggings brought out his sexy curves and nice round ass. Then she announced, "Josie princess, I'll be spending the day with Neil since I missed him all weekend. I've loaned you out to Mill for the day. She has some shopping and errands to do. Be a doll and escort her around for the day, o.k. sweetie."

Josie was nervous about going out in public again. He was not quite as scared as the night before, but still nervous. By now he was well trained to obey Mistress Sarah and he knew better than to protest. "Yes Mistress," he replied obediently.

"Mill is a wonderful friend and I am feeling generous today. I'd like to treat her to a shopping spree. Don't let her pay for anything. Remember, your money is my money now so don't hold back. Buy her lots of stuff."

"Yes Mistress." There was a small voice in his head whispering to Josie that he should not agree to this but he cold not say no to Mistress Sarah. He was under her spell and simply lived to obey her. He was having so much fun living in this fantasy world and so he rationed with himself that it was well worth the money.

CHAPTER 20 Breaking Boundaries

Mill lived just a few doors down from Mistress Sarah. He walked quickly to her door and knocked. She answered the door with a warm smile and greeted Josie with a cheerful. hug "Josie, great to see you again. You look so pretty."

Josie blushed. "Thank you Miss Mill."

"Ready to go shopping girlfriend?"

"Yes I am," replied Josie trying to match Mill's upbeat tone. 

Mill and Josie spent the day hopping from store to store, shopping for clothes. It was a special treat for Josie to help Mill in the dressing rooms. He enjoyed the many glimpses of Mill in her panties and bra. A few times Mill even removed her bra to try on tops and dresses, teasing Josie with her perky breasts.

Every now and then Mill would pick out an outfit for Josie to try on. He tried on skirts, dresses, shorts, pants, and tops. Whenever Mill liked the outfit, she put it in the cart for Josie to buy. The first time they went to the register, Josie handed his credit card to the cashier. The cashier read the name on the card. Then she looked at Josie and smiled. "Got your husband's card today, huh?"

Mill giggled at the comments. Josie blushed and stammered, "Ahh...yes."

"Gotta make em pay when we can," laughed Mill.

"You got that right," said the cashier as she rang up the order.

Josie and Mill laughed as they walked away. "That was close," said Josie with relief. "I better hit an ATM and get some cash."

"No way," replied Mill. "It's more fun pretending it's your husbands card." She gave Josie a wet kiss on the cheek and squeezed his ass. "Thanks for the clothes slave," she said with a giggle. "You've got a few more outfits to buy."

Josie wanted to persuade Mill to let him get cash, but her kiss melted him and he could not find it in himself to argue with her. He spent the rest of the morning buying her and himself more outfits with his credit card. With each purchase he got another kiss, another squeeze on the ass and another 'thanks slave.' He also got another bag to carry. Mill had him carry all the bags and when walking from store to store he had to walk at least three steps behind her as a reminder of his slave status. 

When they finally arrived back at Mill's place, Mill immediately gave Josie a tight hug and then tongue kissed him deeply. Her hand reached between his legs and rubbed his 'clittie'. It started to swell in its bent position.

"Seeing you try on all those pretty outfits has made me so horny Josie."

"Me too," said Josie."

Mill pulled down Josie's stretchy pants. Her fingers grasped his panties at the same time. In one swift motion everything was down to his ankles and his cock was free and growing hard.

"That's what I like to see," said Mill in a lustful tone.

"This is a nice hard cock Joe," said Mill as she squeezed it hard. 

Josie was surprised to hear her refer to him as Joe. "Thank you," he said in his feminine voice.

Mill grabbed his chin firmly and looked straight into his eyes. In a firm controlling tone she said "I want Joe now. Lose that sissy voice slave. Give me Joe right now."

Confused, Josie said, "Yes Mistress," in his man's voice. Oddly it felt un-natural to Joe to use his natural voice.

"Good boy. Now get out those sissy clothes," demanded Mill as she pulled off his wig and flung it to the side.

Josie stripped off his top and bra.

Mill laughed. "Nice tan lines sissy boy. Come with me."

Mill smiled at Josie and licked her lips in a flirty manner. She grabbed his cock and pulled him back to her bathroom. In the bathroom she used make-up remover and special wipes to wash away Josie's make-up. Her left hand held his cock while her other hand cleansed his face.

As Mill slowly wiped away the make-up she looked into Josie's eyes and said, "I know you like to be all pretty and sissy for Sarah, but I want to see the boy that's hidden beneath."

Josie was confused and aroused from Mill. Mill continued, "You know, Sarah lets me play with Neil every now and then. I hear that you are going to be her full time slave. That means you and I will get to play too."

"I like the sound of that," said Josie in his man's voice.

"Every now and then I get the urge to suck cock. I love to suck Neil's cock. Have you seen it yet Josie?"

Josie was even more confused that Mill switched back to using his feminine name. He was not sure which voice to use now. He guessed that she wanted to hear Josie. In his feminine tone he said, "Yes Miss Mill. He has a big cock."

Mill did not correct his voice. She simply replied, "That's right Joe. It good that you noticed how big his cock is."

"Neil has told me about how you sucked his cock," said Josie, switching back to his man's voice. "I was always so jealous of him."

Mill smiled, "Mmmm. That's nice to hear. Were you jealous of this...," said Mill as she bent down. She took Josie's cock into her mouth.

Her tongue slid down his cock as her lips engulfed it. Her warm wet mouth felt incredible against his super sensitive cock. Mill sucked up and down his cock a few times.

"Oh..yes...that feels incredible," moaned Josie.

Mill looked up at him. "Of course it does sweetie." She held his balls lightly in her hands. "I can tell Mistress Sarah is teasing you. Your balls are so full and swollen." Then she took his cock into her mouth again. 

Josie was in heaven. He was not sure how long he could last without blowing his load. He wanted to hold out as long as possible. He was debating whether or not to ask Mill to stop when Mill's phone rang. She stopped to answer it. Normally the interruption would have frustrated Josie, but this time he was thankful because he may not have lasted another second.

It was Mistress Sarah on the phone. Mill gave her glowing report about Josie and let her know that she was having a little fun with him. She ended the call saying, "That sound great. See you in a few."

When she hung up the phone she said cheerfully, "Great news. Sarah and Neil are coming over to join in the fun!"

"That's great! I can't wait," said Josie, although he was half disappointed to lose his alone time with Mill.

"We are going to have lots of fun Joe." Mill pulled a box out from under the bed and removed a set of black leather cuffs and a collar. She started to put a cuff on Josie's wrist but then she hesitated. "Oh wait. Silly me, these are for Neil. I almost forgot you get the pretty ones."

Mill fished through the box and removed a pink collar with diamond studs and matching ankle and wrist cuffs. Josie sat obediently while she put them on him. "It's so cute that you are Mistress Sarah's kitten. You really adore being called her kitty don't you?"

"Yes Miss Mill. I like my nick name."

"Aww. Such a cute kitty you are." Mill laughed and pet his head. "You really are a sissy Joe."

Mill attached a diamond studded leash to Josie's collar. She pulled the leash forcefully toward herself causing Josie's face to be inches from hers. Mill kissed Josie roughly while she held his leash taught. Then she asked to see his kitty tongue. Josie stuck out his tongue for Mill and she playfully bit it while pinching his nipples. Josie grimaced at the sudden pain on his sensitive areas.

"Be a good kitty for me tonight or I will punish you with pain, got it?"

"Yes Miss Mill." Josie knew she was serious. He could tell Mill had a cruel side.

"Good. Now put your panties and bra back on before Sarah gets here."

After Josie put on his bra and panties, Mill pulled his hands behind his back and secured his wrists together. She also attached a short chain between his ankles. Then she tugged on his leash and had him kneel before her. Slowly she stripped in front of Josie, shaking her ass in his face. She stripped all her clothes off and stood completely naked before Josie.

"Do you like my body," she asked.

"Yes Miss Mill. You have an incredibly hot body," said Josie. He meant every word. Josie thought she could easily be a super model with her thin body and perky breasts. She had beautiful long blond hair and the face of an angel.

Mill shook her ass in front of Josie. "Kiss it," she demanded.

Josie leaned in to kiss it and she moved away. With his hands tied behind his back he almost lost his balance. Mill laughed. "Silly sissy."

A voice called from outside the room. "We are here."

Mistress Sarah and Neil walked in. Mistress Sarah immediately commented on Josie, "Oh you look so cute and helpless Josie. I love it! Let's get Neil all tied up too."

Mill and Mistress Sarah stripped Neil and put the black collar and cuffs on him. His ankles were chained together similar to Josie's but his wrists were chained together in front of him. 

Mill said to Mistress Sarah, "I was just enjoying Joe's cock. Seeing Neil's cock is making me even hungrier. Come here Josie. Let me show you what it's like to suck cock. You'll love it."

Mill kneeled in front of Neil. She pulled on Josie's leash forcing him to crawl next to her. Mistress Sarah was sitting on the bed and Neil was sitting between her legs facing Mill. He was sitting on the edge of the bed in a half sitting and half standing position. Mistress Sarah had been playing with his cock so it was hard and pointing straight up.

Mill held Josie's leash tight while she took Neil's cock into her mouth. Josie had no choice but to watch up close. Mill's pink glossy lips slowly devoured the hard cock. Mill looked incredibly sexy and hot kneeling naked, sucking Neil's cock. Her tongue teased the tip of his cock and then licked her own lips.

Mill looked over at Josie. "Isn't this hot," she asked. Mill did not wait for an answer. Her tongue and lips slowly descended on Neil's cock again. Josie heard Neil moan. He looked up at Neil. Mistress Sarah was kissing him and playing with his nipples. Pure pleasure filled his face.

Mill reached down and squeezed Joe's hard cock, bringing him into the chain of sexual pleasure. She held his leash tight and continued to suck Neil's cock inches from his face. Then she looked over at Josie and pulled on his leash and kissed him deeply. Josie's hands were tied behind his back and so he was helpless and at her mercy.

After the brief kiss, Mill returned to Neil's cock for a few seconds. Then she tongue kissed Josie again. She repeated this a few times, alternating between Neil's cock and Josie's mouth. Her right hand held his leash tight. Her left hand stroked Josie's cock.

"This is so hot," she whispered in between kisses and sucks. 

Mill was purposely shortening the time between kissing Josie and sucking Neil's cock. She was creating the illusion of Josie sucking Neil's cock through her mouth. To add to the illusion she asked Josie, "Can you taste his cock in my mouth Joe?"

"Ah...no," whispered Josie, not wanting to confess such a perverted thing.

His denial did not help his situation. It only made Mill more determined. "Here let me squeeze out a little cum for you," she with complete conviction. 

Mill stuck out her tongue and stroked and squeezed Neil's cock until a few drops of cum dribbled onto her tongue. Then with pure lust in her eyes, she tongue kissed Josie, pushing the cream into his mouth. Josie was completely confused and aroused. He knew Mill was purposely pushing his boundaries and this twisted kink excited him. He was horny which made him want to be twisted, kinky and slutty with Mill.




Discovering Mistress Sarah's World Pt. 08



Part 8 -- Complete Surrender

Chapter 21 Leaving Behind Joe's Life

Mistress Sarah was very pleased with Josie's training and feminization. She was anxious to have complete reign over him so she sent him home a day early to pack up his things and prepare to leave behind his life in the Philadelphia suburbs. 

"I'm sending May with you Josie," announced Mistress. "She will look after you and make sure things are done according to plan."

"Yes Mistress." Josie's heart pounded hard in his chest. His immediate thought was, 'this is really happening.' He was scared about the future but he was also extremely excited. His cock was rock hard as knowing that he would soon be fully dependent on Mistress Sarah.

May was thrilled to take time off work and be given ownership of Josie. Mistress Sarah gave them just over two weeks to take care of business and return home. Back in Philadelphia things happened fast as a blur for Josie. Although he had already taken off work for the remainder of the week, May insisted that he go to work on Friday and hand in his resignation letter.

Friday morning May gave him the envelope with his resignation letter and instructed, "Give your boss the letter and then text me and Mistress Sarah the moment you walk out of his office."

She was kind enough to let him dress in normal boy work clothes. However, underneath the clothes Miss May dressed him in a white silk thong and white stockings. His toes nails were painted a bright shiny red and his finger nails were coated in clear polish. It was enough to keep his new feminine side close by, without creating a scene at work. 

Josie felt strange walking into work. Being immersed in a complete feminine world for almost a week had changed his frame of mind and it seemed odd being back to his normal routine. Josie was nervous about resigning. He was nervous about how his boss would react. It was a silly reason to be nervous. Josie had no commitment to work and there was nothing his boss could do about the resignation, but nonetheless Josie's stomach churned uncomfortably.

He wanted to get the resignation over as soon as possible. He went into his boss's office early in the morning and handed him the envelope with his resignation letter. 

"This is not what I think it is," said his boss in a surprised tone. 

Josie laughed uneasily. Managers always seemed to have a mysterious ability to know when they were being handed a resignation letter. 

"Yes Dan, it is. I am resigning." Josie felt the need to apologize. He worked for Dan for over 8 years and it seemed like a crime to be leaving. "Sorry Dan. I have really enjoyed working here and working with you. It's just for personal reasons."

By now Dan was reading the letter. "This is a joke right," he said.

Dan's word's made Josie's stomach tighten into a knot and his face blushed red. It suddenly occurred to Josie that he did not know which letter Miss May had given him. He did not know if it was the serious letter that he wrote or the playful letter about how he was leaving to serve a Mistress and worship women. 

Josie's knees weakened. He was starting to panic when Dan said, "I mean I can't believe you are actually resigning. We are really going to miss you around here."

"oh...ah...yeah...Thanks Dan. I'm going to miss working here," said Josie. He could tell from Dan's reaction and tone that he was reading the normal letter. Josie's panic disappeared as quickly as it came. 

Josie spent the next half hour in Dan's office answering questions and discussing the resignation. Finally Dan conceded, "Well I guess if you've already made up your mind about moving away, there is nothing I can do here to make you stay. I'll just have to wish you good luck."

Josie felt relieved when he walked out of Dan's office. He went right to his own office and texted Miss May and Mistress Sarah, "Just left my bosses office. The resignation is official."

Miss May responded immediately. "Way to go kitty-kat! Feels great doesn't it? I will have a nice reward for you when you get home. For now your treat will be to stroke Joe's cock. Go into the bathroom, pull your pants down and play with your man's cock. Get Joe right to the edge and then stop. Wait one minute and do it again. This time when Joe is on the edge, squeeze out some cum and lick it up. Enjoy the creamy treat pretty kitty. I know it's what you want."

Josie's 'clittie' throbbed between his legs just from reading the text. He immediately went to the bathroom and followed May's orders. Someone was at the sink washing their hands but Josie did not care. He went into a stall and quietly stroked Joe's cock, getting himself right to the edge. Josie's urgency to follow May's orders and lack of nervousness in doing a perverted act in a public bathroom with others around were proof that Mistress Sarah's training and conditioning were effective. A serious transformation had already occurred within him. 

After a short rest, Josie took himself to the edge again. He squeezed out a few dribbles of cum onto his fingers and licked them up. The taste was all too familiar. He felt dirty and slutty. These emotions were comforting to him. The resignation of his job was starting to sink in. Another connection to his normal life was being severed and he was excited by it. He was standing in his work's bathroom in panties and stockings, with 'Joe's' cock in his hands and he felt good about. 

A strong desire was quickly growing inside to want to be dirty and slutty. He wanted Miss May to make him do all sorts of perverted things. He was unprepared for this strange emotion. He wanted to cum bad. He texted Miss May, 'I want to be your dirty slut. Please make me do slutty things. Please let me cum!"

Miss May texted back, "Calm down slut. Control yourself. See you tonight. Hurry home."

Josie was disappointed that Miss May did not want to play. He pulled himself together and went back to work. The end of the day could not come soon enough. At 5:00 sharp he raced for the door and headed home. 

Miss May greeted Josie at the door and she was a glamorous sight. She spent the day at the salon and went all out. Her short hair was styled in waves to give her a cute and sassy look. Her face was painted to perfection and shined with beauty and her pink nails matched her pink glossy lipstick. She wore a tight black dress with foil highlights that added a shimmery wet look. The dress hugged her curves in all the right places and stopped at her mid-thighs. A small triangle of see-thru lace went from above her bust to her neck, with two straps that tied around her neck. The dress was glamorous and bordering provocative.

Josie practically drooled at the sight of her. "You look breathtaking," he said. 

Miss May could not contain her smile. She glowed as she said, "Thank you Josie. This is a day to celebrate. Let's go have dinner."

Josie was already dressed in a suit so there was no need to change. Miss May had made reservations at the Devone Seafood Grille, an upscale restaurant in the city. Miss May and Josie both enjoyed a delicious meal and expensive wine as they celebrated Josie's resignation. After dinner, they headed to a nearby nightclub to enjoy drinks and dancing. Miss May was a bartender and knew her drinks well. She had fun ordering different variations of drinks for Josie to try. She was careful not to give him too much as she did not want him to be drunk for her planned evening event. 

All-in-all it was a fun night for Josie. He enjoyed dancing and spending time with Miss May. While they danced, Miss May enjoyed sneaking her hand down to his cock and rubbing it until he got an erection. Then she would tease him further by rubbing her ass against his hard cock. Josie was enjoying the fun and was a bit surprised at how normal the night was. Miss May had maintained a dominant role with Josie, but other than that it was almost like a date. They even kissed a few times on the dance floor. He wondered if this was part of his gift. Perhaps this was his last night to spend time with a woman as 'Joe', even though he was wearing panties and stocking underneath his suit.

When they arrive back at Josie's apartment, Josie, thanked Miss May for a wonderful night. 

"The night is not over sexy," she said with a devilish smile. "Come with me."

May grabbed both his wrists and pulled him back to the bedroom. In the bedroom she stripped him down. At the sight of his panties and stockings she smiled and said, "mmm. So sexy Josie." She rubbed her hands over the silk triangle that barely covered his hard cock. Through the silk, her fingers traced the outline of his cock up and down and up and down. Josie's body shuddered at the wonderful feeling.

"Does that feel good princess," said Miss May in a seductive and teasing tone.

"Yes Mistress," replied Josie.

"I bet you already want to cum, don't you?"

She was right of course. All the teasing and torment over the last few days had turned Josie into a weak ball of horniness. After just a few strokes of her fingers he was feeling the urge to cum. "Yes Mistress. You're making me feel so good."

Miss May laughed and ordered him onto the bed. She commented, "We'll leave your lingerie on. You look so sexy in them."

Miss May then proceeded to tie Josie down. His wrists were tied to the head board and his ankles were tied to the base of the bed. She did not tie him spread-eagle. She preferred to have him in a more relaxed pose with his hands straight above his head and his legs just about shoulder width apart.

Josie's eyes followed Miss May as she slowly walked around the bed admiring him. The click of her heels on the wood floor echoed in the room. Her hand traced across his chest and stomach, which sent chills through his body and caused his hard cock to twitch against the panties. Miss May was not pleased with the confinement of his cock. She pulled the panties down to his thighs, freeing his hard cock.

"Much better," she said as she stared at his throbbing cock.

She looked incredibly sexy in the tight shimmering dress. "You look amazing Mistress," complimented Josie.

Miss May smiled on the inside. To Josie she maintained a firm controlling image. "Of course I do slave." She laughed seductively. "You're in love with my body, aren't you slave?" Miss May swayed her hips side to side in a slow and sensual rhythm. She slid her hands from her waist up to her breasts. "You want to suck on my perfect breasts don't you?" 

"Yes Mistress."

Miss May stood on the bed above Josie's head giving him a perfect view of he black satin thong panties. Then she teased, "Do you like what you see Josie? Do you want to taste my sweet pussy? Do you want to lick my beautiful ass?"

"Yes Mistress."

Miss May laughed at his response. She sat down on his chest and nonchalantly sighed, "Of course you do slave."

Josie was staring right at her crotch. Her dress was so short that it cinched up to her waist when she sat on his chest. She managed to wriggle out of her panties. She slid them off her legs and dropped them onto his face. Josie inhaled, trying to take in as much as her scent as possible.

Miss May laughed. "You're pathetic," she mused. "Here let me help you." She spread open the panties and pressed the crotch against his face. "There you go slut. Get a nice big whiff."

Josie inhaled deeply. The smell of her pussy was much stronger now and he loved it. Miss May held the panties firmly over his nose. "That's it slave. Smell it. You are so easily aroused slave. Just smelling my panties all day would make you happy wouldn't it?"

"Yes Miss May," mumbled Josie into the panties.

"such a slut," laughed Miss May.

Miss May let Josie continue to smell her panties while she retrieved a dildo. "I've got something special for you slave. It's part of your gift tonight." She waved the dildo over his face. "I know how much you've love to have your pussy filled."

Miss May lubed up the dildo and slowly pushed it into his ass. As the dildo filled his ass the thoughts of a normal night that entered his mind earlier in the evening drifted away. No normal man would be lying in bed in panties, stockings, and a garter belt, with a dildo in his ass. This didn't bother Josie at all. In fact he loved that it was not normal. The fullness in his ass was a welcome pleasure. 

Miss May pulled her panties away from his face and looked into his eyes. "How are you doing slut?"

"Very good. This is a wonderful gift."

Miss May smiled. Her hand lightly caressed Josie's cock. "Oh, this is not the gift Josie. You are going to really love the gift." The light stroking was putting Josie into a wonderful erotic trance. He wanted to know what his gift was but Miss May changed the subject. "Such a big clitty you have darling. Let's rub our clitties together, shall we?"

Miss May sat with her pussy on top of Josie's cock, pressing it against his stomach. Her pussy was cleanly shaven for the special night and Josie could see that her swollen lips were molded around the sides of his cock. Her pussy was hot and wet and it felt incredible pressed against his cock. Miss May slowly moved forward so that her wet pussy glided along the under-side of his cock all the way up to the tip. Josie let out a moan.

Miss May teased, "Did that feel good princess? Do you like when I rub my pussy over your clittie?"

"It feels incredible," moaned Josie.

Miss May slowly slid backwards all the way down to his balls. Josie let out another moan. Miss May giggled. She paused for a few seconds and the slowly slid up to the tip again. Miss May repeated this again but at a faster pace. Josie could not stop moaning. It felt so good that his natural instincts kicked in and he thrust his cock against Miss May. This proved to be a big mistake. Miss May instantly slapped his face hard. The sting to his check shocked him. He forgot how cruel she could be.

"Do not thrust slave," she yelled harshly. "Remain still!"

"Sorry Mistress," apologized Josie. Her slap was harsh and somewhat cruel but Josie loved it. It put him in his place and made him feel even more helpless and submissive. There was something strangely erotic and sexy about the way she instantly subdued him.

Miss May started sliding up and down his cock again. Josie focused on remaining still. Miss May's voice changed back to sweet and seductive. "Feels so good, doesn't it princess? It feels good for me too. I bet you want to cum right now. I bet you want to feel your cock inside my pussy, don't you?"

"Yes Mistress," whispered Josie.

"I want to feel it too Josie. Maybe just a little."

Josie could not believe her words. He was surprised that she used the word cock instead of clitty. He was even more surprised that she might actually let his cock inside her. For a second he thought she was just teasing him but then she lifted herself up and held his cock straight up so that the tip was positioned just below her swollen pussy. 

Josie watched the tip of his cock disappear into her hot pussy. The tight warn wetness around the most sensitive part of his cock sent waves of pleasure through his body. Her pussy was inviting and he wanted to thrust in deeper so bad but the warmness on his cheek was a reminder to remain still.

Miss May could see the struggle on his face. She lifted herself up and let his cock fall onto his stomach. She laughed cruelly. "You know it's a rare privilege to let a sissy's cock inside the pussy of a Goddess, don't you?"

"Yes," whispered Josie. "Thank You Miss May."

"Let's try it again sweetheart."

This time Miss May pushed down further allowing almost half his cock inside her. She paused for a second or two and then slowly lifted herself up. Josie's cock was so sensitive he could feel her pussy lips sliding along his cock as she raised herself up. It had been months since his cock had felt the inside of a pussy. The feeling was incredible. 

"That feels so good Miss May," moaned Josie.

"This is your gift sweetie. Tonight I will allow your cock inside of me. Do you think you can handle it?"

"Not without cumming," admitted Josie. 

The words were honest but Josie regretted saying them as soon as they came out of his mouth. He thought he blew his opportunity. However, Miss May just laughed. "You are so weak sissy. Let's let your cock rest for a moment. It may be the last time your cock is allowed inside a real pussy so I want you to at least last a minute or two"

Miss May moved forward and sat on his stomach. She undid the strap to her dress and let her top fall. Josie enjoyed the sight of her perky breasts and hard nipples. She leaned forward and Josie eagerly licked and sucked her nipples. Josie's lips were warm. The combination of his warmth and his wet tongue caused sparks of pleasure to shoot through May's body. 

Miss May was enjoying her powerful position. It was a thrill to have Josie beneath her, tied up, helpless, and on the brink of orgasm. It was a thrill to see him struggle to maintain control and to not orgasm. She knew that she could send him over the edge at any time and that he was so weak that she could make him cum on command. This was a thrilling and arousing power. Soon it was Miss May who was struggling not to orgasm. Her pussy grew wetter and hotter. She could orgasm if she wanted to, but she chose not too. She wanted to save her orgasm for just the right moment.

Miss May raised her tits a few inches out of reach of Josie's mouth. In doing so, her body edged backward just enough that her pussy rubbed the tip of his cock. Josie moaned. Miss May teased, "awww...does my pussy feel good? You want to cum so bad don't you sissy? Do you want you cock inside me again? I bet you want to cum in me. Do you think I'll let you cum in me?"

Josie was so aroused and confused from the teasing. He loved everything that was happening to him. He did not know what to say. He did not know how to answer, afraid that he might say the wrong thing and upset Miss May. 

Miss May pushed backward and the tip of Josie's cock pushed into her sopping wet pussy. Instantly his eyes closed and a moan escaped his lips. Miss May moved forward again and giggled as her pussy released his cock. Then she said in a seductive but commanding tone, "Pretty Josie, the next time your cock is in my pussy I am going to take all your cum."

Josie's eyes opened in surprise and delight. 'Was she really going to let him cum inside her,' he thought.

Miss May read his thoughts, "That's right slave, you are going to cum inside me. My pussy is going to milk every last drop of man cum out of you. That is your gift slave. When I take the last drop, you will forever be a sissy slave to Mistress Sarah and me, do you understand?"

"Yes Mistress," replied Josie. He completely understood and he loved it. Josie loved that his gift was a ritual signifying his new life. He knew that although Mistress Sarah was not there in person, she was the one who orchestrated the whole night and the ritual that was taking place. Mistress Sarah was a natural genius at the mental aspects of seduction and domination, which was why Josie could not escape her power. It was the same power that kept Miss May, Mill, Nellie, and Julie drawn to her. It is a wonderful power that no one wants to escape once they experience it.

Josie was completely under Miss May's spell but just like Josie, May was a pawn in Mistress Sarah's game, following her orders, carrying out her supreme plan. She used very specific words to emotionally dominate Josie. Josie's mind clung to these triggers - 'I am going take your cum,' 'My pussy is going to milk every last drop of man cum out of you,' 'you will forever be a sissy slave.'

Although Josie acknowledged that he understood all this, Miss May said, "Repeat it for me slave. I want to hear you say it. Say 'Miss May is going to take all my cum and when my last drop of cum is milked out I will forever be a sissy slave to Mistress Sarah and Miss May.' Say it now slave!"




Discovering Mistress Sarah's World Pt. 08



Josie repeated the words. As soon as he finished Miss May ordered him to say it again. She did this four more times. The sentence became a mantra to Josie and put him into a completely submissive mode. After the fifth time, Miss May said, "It's time to seal your fate." Then she slowly slid back onto Josie's cock. She let it penetrate her completely. Once his cock was fully engulfed she sat upright on Josie's stomach and began to slowly ride his cock up and down. 

Her pussy was hot and wet and it felt spectacular rubbing over his hard and sensitive cock. He could feel her pussy muscles clenching his cock and pulling on it each time she lifted herself up. His mind went blank and he saw fireworks each time the full weight of her body pushed down onto his cock. He wanted to thrust into her, but he knew that she expected him to remain still. She was on top, and she was the one doing the fucking. He was not going to cum into her but rather she was going to take his cum. Josie understood all this and obeyed. 

Miss May deliberately fucked him slow to show her power and control and to tease him unmercifully. Josie's hands gripped tightly around the ropes that went from his wrists to the head board. His back arched and his toes curled in pleasure. He was keenly aware of the soft stretchiness of the stockings around his toes and of the dildo pushing deep into his ass each time Miss May pushed down onto him. These were reminders of who he was now. He thought of Miss May's earlier words, 'This may be the last time your cock will be in a real pussy.' The words should have frightened him but instead they thrilled him. He knew he would long for this moment again, but to know that he would be denied this ultimate pleasure by two beautiful goddesses was exciting.

The gift in itself was twisted and perverse. At first Josie thought it was their way of letting him have his last male orgasm, the last experience of sex as a man. However, he felt nothing like a man. He was tied down beneath Miss May and forced to remain still while Miss May rode his cock. He was wearing panties and stockings and he had a dildo pushing into his ass. This was not the way a man would have sex. This was how a sissy slave experiences sex. At that moment it was clear to Josie that he would never again experience sex as a man. His new life had already begun. It had started the day he met Mistress Sarah, he just did not know it then. 

All these revelations flashed through his mind in seconds and they excited and aroused him even more. He was glad at what he had become. He savored the feeling of fullness in his ass. He loved the stretchiness of the stockings against his legs and he could barely handle the sizzling pleasure from Miss May's pussy. 

Then it happened. Miss May looked directly into his eyes and commanded, "Give me all of your cum Josie."

On command, Josie let go and for the first time in months experienced a full blown orgasm. He moaned loudly from the rare pleasure. Miss May timed her orgasm to be in synch with Josie. She bounced up and down and her pussy convulsed and gripped tightly around his throbbing cock. She moaned, "That's right Josie. Give it to me. Give me all your cum."

The orgasm seemed to last for ever. Even after Josie though he was done, Miss May continued to ride his cock. She pressed her hands onto his wrists and squeezed her pussy muscles as she lifted up. In a firm tone she said "Feel my pussy milk out all your man cum. I want every last drop of it."

When Miss May was finished, she leaned forward and kissed Josie on the cheek. "You are all ours now Josie," she whispered into his ear.

Miss May laid on top of Josie for a few minutes with his cock still in her pussy. Her body felt warm and comforting. Josie was exhausted and drifted in and out of sleep. He expected Miss May to slide up onto his face and make him lick the cum out of her pussy but she never did. She took his cum. It was the last of his 'man' cum and she was going to keep it. 

Eventually Miss May moved off of Josie. Josie was drifting deeper into sleep so he barely moved. He vaguely remembered her wiping his cock off with a wet cloth. It seemed like she was doing something else with his cock but he was tired and he did not pay much attention. The last thing he remembered was her untying his hands and sliding into bed with him. 

Chapter 22 Selling Off His Life and "Manhood"

Josie woke before his alarm clock went off. His awakening was gradual like waves slowly edging up onto the beach. He was in a sleepy dreamy state, reliving his magical night with Miss May. The sex was incredible but what was even more fantastic was how perfect she played the dominant role. Every move she made, everything she said, and even the firmness in her tone had put Josie into a euphoric state of submission. That night would live in his memories forever.

These thoughts and images aroused Josie. His arousal grew but something was not right. Something was pressing into his 'clitty' and keeping it from swelling. Everything felt tight. Josie lifted the covers and could see something around his clittie. It was hard to make out in the dark. 'It couldn't be,' he thought. 

Josie slipped out of bed and confirmed what he thought. He was wearing a chastity device and it was locked on with a padlock. It was meant to keep him from getting aroused but the discovery of it had the opposite effect. His arousal intensified at the realization that he was locked up. He truly was a slave. Miss May was right. Mistress Sarah and Miss May owned him now.

Josie's movement caused May to wake up. In a sleepy voice she whispered, "Like your new clitty cover?"

"Yes...I guess," answered Josie unsure if this was a good thing or bad thing.

"You better learn to love it," replied May amusingly. "You're going to be wearing it all of the time now. You'll only be allowed out when we want to play with you or when you're ready for your milking."

"Milking?" Josie questioned this but he already knew the answer.

"Yes princess. Last night was your last full orgasm. That is unless you get Mistress Sarah in a very generous mood but I can tell you those times will be rare. From here on out you will be milked of your cum every few months."

It was another moment where Josie thought the he should be scared and running away, but instead he was aroused and excited at what Miss May was telling him. Mistress Sarah and Miss May's power and control were squeezing tighter and tighter around him and he loved it. Being milked like an animal by a beautiful Mistress was thrilling to Josie in some perverted and twisted way.

Josie was excited and confused. All he could think to do was respond, "Yes Mistress."

May was still tired. She closed her eyes and enjoyed the comfort of the warm covers. Before drifting back into sleep she commanded, "Shower yourself slave and then bring me some breakfast. We have a busy day so don't keep me waiting long."

Josie immediately obeyed. After breakfast, May had him dress in pink panties, pink stockings, and a matching pink bra. That was his work outfit for the day. May on the other hand was dressed comfortably in jean shorts and a t-shirt.

May was spot on about the day being busy. It started with a phone call from Mistress Sarah. Miss May put her on the speaker phone so the Josie and her could hear the instructions together. When the phone call was over they were clear on what had to be done. The main task was to get everything in Josie's apartment either packed-up and ready to move or put out ready to sell. 

Josie was allowed to pack one medium size suitcase with his silly man clothes. Mistress Sarah emphasized, that this suitcase would be locked away at her house and would only be brought out if necessary, if he was visiting friends or family. He was also allowed to fill two boxes full of personal items that he wanted to keep. Everything else had to go. All furniture, clothes, pictures, appliances, plates, and other items were to be put up for sale. Anything that was not sold would be donated or trashed. 

Josie's whole weekend was spent packing and getting ready for the moving sale. While he sorted through things, Miss May set-up tables and put prices on the items for sale. Everything was priced to go. It was a bit disheartening to see his dining room table priced at $400 when he bought it for over $1,000 just a few months earlier. Josie mentioned this to Miss May and she simply shrugged her shoulders and said, "We need to sell if fast Josie. Besides, this is all Mistress Sarah's property now, so your opinion does not matter slave."

She was right of course. There was nothing Josie could do about it. A few items were tagged with Miss May and Mistress Sarah's name. It didn't take much for Josie to figure out that these items were being claimed by his two Mistresses. Miss May wanted his flat screen TV, stereo system, and a few crystal vases. Mistress Sarah's name was attached to a beautiful china cabinet, and his kitchen set.

By the end of the weekend almost everything in the apartment was marked and ready for sale. On Sunday night Miss May had Josie hang 'Moving Sale' posters around the neighborhood. Unknown to Josie, an ad had already been placed in the paper. Mistress Sarah and Miss May planned for a big turn-out for the sale. The less they had to give away at the end meant more money for them.

People were already showing up for the sale on Monday morning when Josie left for work. Miss May greeted them with smiles and dollar signs in her eyes. As Josie drove off to work, he wondered how much of his life would be sold off while he was away. 

Word spread quickly at work of Josie's resignation. Most of his day was spent fielding calls and visitors inquiring about his resignation and wishing him good luck. Although he was paranoid about wearing the chastity device, with all the visitors he had little time to think about it during the day. Occasionally he would glance down at his crotch to make sure it was not noticeable. He was impressed at how easily it was to go to the bathroom with it on. He had to sit down to pee, but that was expected of him anyway. At least now Mistress Sarah could be certain that he was not standing like a man. It gave new meaning to the idea of forced feminization. 

Josie did not get much work done, nor did he care about getting work done. Mentally he was already checked out and he couldn't wait to get started on his new life with Mistress Sarah and Miss May. The end of the work day came quick and he hurried home to see how the sale went.

When he arrived at home, Josie could see a few men loading into a pick-up truck, what used to be his couch and loveseat. A young woman was exiting his apartment carrying brass lamps that he had owned for over 10 years. Apparently the sale was going well. The inside of his apartment was filled with strangers. Josie was surprised at how much of his stuff was gone. It took him a few minutes to find Miss May.

When Miss May spotted him, she exclaimed, "Kitty Kat!" and she ran up and hugged and kissed him. Josie blushed as a few people looked their way. "The sale is going great!"

"I can see that," said Josie. 

For the next hour Josie helped with the sale. At 7 pm they shut the door so they could unwind and relax. The sale would resume again first thing it the morning. Miss May's first order to Josie was to strip down to his panties and prepare dinner. Josie baked a full meal of chicken, potatoes, and corn. He served it wearing nothing but the white cotton panties that he had worn under his work clothes all day. After dinner Miss May insisted that Josie freshen up with a bubble bath and by shaving the stubble that had grown in on his face during the day.

After his bath, Miss May adored his chastity device. She tapped on the hard clear cover with her nails and giggled. "It's such a cute clitty cover." She even leaned down and kissed it. "I bet you wish you could feel my lips against your clittie Josie."

"Yes I do Mistress. Please let me out," begged Josie. He voice was filled with pleasure and pain. His arousal was growing causing his cock to swell against the hard tube.

Miss May put her lips over the clear tube and rubbed her tongue over the tip. Josie could barely feel her tongue on his slit. He moaned. "Please let me out."

Miss May was enjoying torturing Josie. "Aww. What's the matter princess? Does your little clitty want to be all big and swollen? Do you want to feel your clitty in my mouth?"

"Yes, please," begged Josie.

Miss May's hands tickled and teased his balls. Josie felt like his cock was going to burst the chastity device but it held firm. He had only been in the device one day and already he was desperate to be free.

"Well we did have a good sale today Josie. Maybe as a reward I can let you free for a bit. I made almost $2,000 today. I should be able to buy some nice clothes and jewelry for myself with that money. Maybe if you're good, I'll buy you a pretty bracelet and necklace. Would you like that princess?"

"Yes I would like that," replied Josie feeling even more submissive. Josie figured he would not see a dime of the money from the sale of his things, especially after Miss May had indicated earlier that all his possessions belonged to Mistress Sarah. He also knew that Miss May purposefully mentioned spending the money as way of reinforcing her control over him and perhaps to test him to see if he would challenge her. 

Josie of course did not challenge her. He accepted defeat and his future as a slave to her and Mistress Sarah. He agreed to what she said and awaited her next words. Miss May teased his locked up cock a bit more. Then she disappeared from the room and returned with the key. She held the key up and smiled. "I will unlock you as a special treat but there will be no cumming for you sissy, understand?"

"Yes Mistress."

"Good sissy. I want all your attention on me tonight. I've had a tiresome day selling all this stuff. I need some pampering and then the cover goes right back on, got it?"

"Yes Mistress. Thank you Mistress!"

Miss May unlocked the padlock and slowly removed the hard tube and ring that held it secure around the base of his cock. Josie's cock immediately grew hard. Josie was happy to be free. "Thank you," he said again to Miss May.

"Your welcome pet. Now start rubbing and licking my feet."

Josie went to work on her feet. He spent the next 30 minutes slowly undressing and massaging Miss May's body. His cock remained hard the entire time he worshipped her body. He loved seeing her completely naked. Her body was slender and delicious looking. Miss May let him spend extra time massaging her breasts and nipples. 

Miss May pushed him down to her pussy and he eagerly lapped at her wetness until she came with a tremendous force. The minute her orgasm hit she squeezed her thighs tightly around his head holding him tight against her pussy. Her hands pressed into the back of his head forcing him deeper into her pussy. Josie was weak and helpless between her legs. She used him selfishly for her pleasure. Even after her orgasm passed, her thighs remained clenched around his head, holding him close to her pussy.

Miss May could feel his deep breaths blowing across her pussy lips. His face was only inches from her hot sex. For several minutes he was forced to stare at her pussy and breathe in her scent. This was his place in life. He was at the mercy of her pussy.

"Thank You Miss May. That was great," complimented Josie. He did not have an orgasm but he truly enjoyed pleasuring his Goddess and it was thrilling to bring her pleasure while being denied.

"Why don't you thank my pussy while your down there," ordered Miss May smugly.

Josie stared into her pussy and said, "Thank You."

Josie felt her thighs squeeze tightly around his head and then release slightly. "Who are you thanking slave?"

"Your pussy," replied Josie feeling somewhat silly.

"Then address it properly slave."

Josie replied, "Thank you Miss May's pussy."

Miss May laughed arrogantly. "That's good. Say it again."

Even though it was just him and Miss May in the room Josie felt a twinge of humiliation at talking to her pussy. He repeated. "Thank You Miss May's pussy."

Miss May was having fun. She released his head and rolled over slightly so that her ass was in front of his face. "Now thank my ass Josie. Give it a big kiss first."

Josie kissed her right on the pucker hole and said "thank you Miss May's ass."

Miss May laughed again and said. "It's amazing what you slaves do. Get up on your hands and knees dirty slut!"

Josie did as instructed. Miss May slipped on a strap-on, lubed up his ass and went right to work fucking him. Josie was quickly getting used to being fucked in the ass. Each time it was becoming more enjoyable. The fullness inside him was naughty and delicious. 

Tonight she pounded him hard and fast. There was no orgasm waiting for him and there was no orgasm for her. It was all about him being a fuck toy and Miss May proving her dominance over him. As she fucked him hard, she pulled his hair, forcing his head to look up. "That's right slut, tonight you are all mine! I own you. I'm taking your possessions and I'm keeping every dollar earned from this sale! Isn't that right slave?"

"Yes Mistress!"

Miss May's fucking slowed but she penetrated deeper into his boy pussy. "Mmmm. You are my bitch! I'm going to fuck your sissy pussy every night and you are going to enjoy it! I'm going to keep you locked up and dress you like a pretty sissy! You are so weak slave! My weak little sissy slave!"

Miss May repeated these words over and over again while she fucked Josie. Finally she dismounted him and pushed him away. She threw him the strap-on on and ordered him to clean it and then lock his chastity device back on.

The rest of the week went in a similar manner. Each day he went to work and then came home and helped with the sale. He would then shave, take a bubble bath, pretty himself up and spend the rest of the night serving and pampering Miss May. Each night Miss May pegged him in the ass with a strap-on. By the end of the week she had moved up to a larger strap-on, congratulating Josie on how well his boy pussy was molding into the perfect fuck toy. 

The only thing that remained different from his Monday routine was the Miss May did not let him out of his chastity device. She took great pleasure in pegging him and demeaning him while his cock remained locked-up.

Josie's apartment cleared out quickly during the week. Miss May ended the sale on Saturday evening. That night Miss May allowed Josie to drink champagne with her to celebrate how successful the sale was and how much money she made on the sale.

On Sunday, Miss May had Josie dress in completely feminine attire. He wore a plain shirt with a black skirt. Underneath he wore pantyhose and a lace bra that was filled with his false tits. Miss May require him to put on his blond wig and a full face of make-up with glossy red lipstick. He was also required to wear his black heels. It was not the most comfortable outfit for working around the house, but comfort was not Miss May's concern. 

When Josie was dressed, Miss May informed him that someone would be coming soon to look at his car and he was to be on his best behavior. At this news Josie gave her a calm and obedient 'Yes Mistress.' However, on the inside he was shocked and panicking. It was shocking because he did not even know she was going to sell his car. He was panicking because he was going to meet someone while dressed as a girl. He did this at Mistress Sarah's house but this was much different. He was in his home. He was in his hometown. What if he knew the person? What if the neighbors saw him?

There was a knock on the door and Miss May looked over at Josie with an amusing smile on her face. "Get the door for me slave."




Discovering Mistress Sarah's World Pt. 08



"Yes Mistress."

Josie walked to the door slowly in his heels. His heart beat wildly and his face already started to flush with embarrassment. He took a big breath and opened the door. "Hello, can I help you," he asked in his well practiced feminine voice.

On the door step stood a man in his mid thirties. Josie was certain the man gave him a strange look. The man said, "Yes, I'm Rich. I'm here to look at the car. Are you May?"

"No sir," replied Josie. After the word 'sir' escaped from his lips, he wondered why he said it. He did not want to feel inferior to another man, but from all his training and in his current state it seemed like a natural thing to do. "Miss May is inside. Please come in."

Miss May introduced herself to Rich and then took him outside to show him the car. She made Josie come outside as well, just for fun. Josie followed Rich and Miss May around the car like a lost puppy. He felt silly being the only one that was dressed up and wearing a short skirt. He felt like a tramp as he clicked around in his heels. Josie kept to himself, nervous about being exposed and nervous about his neighbors seeing him.

May was thrilled when Rich decided to buy the car. When he wanted to talk price, Miss May said to Josie in an commanding tone, "Josie, clean out the car while Rich and I discuss the price." Then she grabbed Rich's arm and pulled him toward the house. 

When Josie finished cleaning out the car he went into the house. He was immediately taken aback at what he saw. Miss May and Rich were sitting together in an oversized chair, one of the few pieces of furniture that remained. Miss May was half sitting on Rich with his cock in her hand. Josie immediately apologized, "Sorry, I did mean to interrupt. I will come back later." 

Josie turned quickly to leave but Miss May stopped him. She ordered, "No! Stop slave! Get over here!"

Josie obediently walked over to Miss May. His eyes were cast downward. His face was blushing with embarrassment at being dominated in front of a male stranger. The look on Rich's face was one of amusement and disbelief.

"Kneel," commanded Miss May. 

Josie obeyed, kneeling in front of Rich and Miss May. Miss May slowly stroked Rich's cock as she spoke to Josie. "Rich here has decided to offer us more than what we asked for the car. Isn't that nice princess?"

"Yes Miss May," replied Josie still embarrassed but snickering quietly to himself. He knew that the offer was not out of Rich's generosity but more Miss May's ability to manipulate and seduce him.

"He is even being kind enough to let us hold onto the car for the rest of the week until we leave for home. I think we owe him a special treat for his kindness, don't you princess?"

"Yes, of course," replied Josie, unsure exactly what she meant. He was certain it would involve something humiliating for him.

"Good. Why don't you stand up and show Rich the sexy lingerie you are wearing."

Josie heart pounded in his chest. He wondered if Rich knew he was really a man. He was scared at how Rich might react when it became obvious. Josie slowly stood up. Miss May ordered him to turnaround and slowly peel down his skirt. "Be sexy for us," demanded Miss May.

Josie felt silly trying to be sexy for another man but he knew he had to do it. Miss May would surely punish him and embarrass him even more if she was not pleased with his performance. Josie slowly pulled the skirt down and wiggled his pantyhose covered ass.

Rich was watching with wide eyes while Miss May played with his cock. She said to Rich, "See how slutty she is. She is not even wearing panties. She does have a cute ass doesn't she?"

"Yes," replied Rich still in disbelief at what was happening.

"Unsnap that bra princess. We want to give our client here the full show."

Josie kept his back to them and slowly undid his bra and slid it off. The falsies fell into the bra cups. He quickly folded the bra over and threw it away from him so that Rich would not see the evidence of fake tits. Josie hoped that Miss May would keep playing the teasing game with Rich and not make him turn around. He was very nervous about Rich discovering his true identity.

Little did he know that he was the one being teased and tormented. Miss May had already revealed to Rich that he was a sissy. She knew that Josie was panicking and she loved to see him so scared and weak. 

After what seemed like an extremely long moment of silence Miss May ordered, "turn around slut. Show Rich your clitty."

Josie slowly turned. His face was beet red. His eyes were glued to the floor, afraid to look up. He heard Rick exclaim, "Oh My!"

His heart seemed to stop. He did not know if Rich was surprised, angry, or happy. Then Rich laughed and said, "I didn't believe you. I wouldn't believe if I didn't see it. Your sissy really is in a chastity device. I never knew such a thing existed." 

Josie became even more embarrassed but he was filled with relief. He was relieved that Rich did not freak out. Miss May waved Josie to come closer. Then she reached out and peeled down his pantyhose to his thighs.

"Isn't it cute," she said to Rich while tapping the hard tube with her fingernail.

"This is wild," Rich said. He reached out and squeezed his fingers around the hard tube that encased Josie's cock. Josie looked up at Miss May startled and surprised at how forward Rich was with him. Had it been another girl grabbing his cock, he would have thought nothing of it, but to have a strange man hold his locked up cock in his hands was humiliating and strange for Josie.

Josie found no comfort in Miss May's eyes. In fact she smiled wickedly at him enjoying his predicament. In a matter of seconds Josie went from snickering to himself at how Rich was being manipulated to suddenly finding his cock firmly held in Rich's hands. Josie felt weak and submissive in front of Rich and this ashamed him.

"Let's go to the bedroom," ordered Miss May. "Playing with Rich's big cock has made me very horny. I want to taste it."

Josie followed Miss May and Rich to the bedroom. They had to use the spare bedroom since the bed and furniture in the Master bedroom had been sold during the house sale. There was just a small single bed in the spare bedroom. Seeing that there were no sheets were on the mattress, Miss May ordered Josie onto the Mattress saying, "I can't lie on a bare Mattress. Sissy slave you will have to be my sheets. That's about all you're good for with Rich and I. Get on the bed!"

Josie lay on his back on the bed. Both Miss May and Rich stripped off their clothes. Miss May laid on top of Josie in a missionary type position. Her naked body felt delicious and inviting against Josie's bare flesh. Having the chastity device on was extremely frustrating for Josie. He really wanted to feel his cock grow hard and he desperately wanted to push it into Miss May's dripping pussy. Josie never imagined how horny he could get while in a chastity device. His feelings were irrelevant anyway. Miss May was here to have fun with Rich. Josie's only purpose was to be her sheet and to be humiliated for Miss May's pleasure.

Rich stood at the end of the bed. His hard cock bobbed over Josie's face. Miss May grabbed his cock and took it into her mouth. Josie could do nothing but lay there and watch as Miss May sucked a hard cock inches from his face.

Miss May teased, "Josie, if you had a big cock like this, maybe I'd suck it too."

Josie thought for sure that Miss May would eventually force Rich's cock into his mouth. He was prepared to suck it if that what Miss May wanted. It ashamed Josie at how easily he was ready to accept this. He was also confused at how aroused he was at the moment. He wanted to think that his arousal was strictly related to the erotic sensations of Miss May's body sliding over his while she sucked Rich's cock. However, there was a part of him that was aroused at the prospect of being forced to suck a strange man's cock. He wanted to be slutty and prove to Miss May that he could be a good cock sucker. These feelings were a new twisted part of his mentality now. Josie's mind had been conquered by Mistress Sarah and Miss May and was being rebuilt into something unrecognizable by Josie.

What made the situation even more perverse was that Josie was actually disappointed when Miss May did not require Josie to suck Rich's cock. Instead Miss May turned around so that her pussy was over Josie's face. "Do you like my pussy, slut? Do you want to lick it," teased Miss May.

"Yes Mistress," begged Josie.

Miss May laughed arrogantly. "The only way you are licking my pussy is if it us full of cum. You do want a nice creamy cream pie don't you princess?"

"Yes Mistress."

"Then you better beg Richey to fuck me. Go ahead princess; beg him to fuck me so that you lick his cum out of my pussy."

Even though he was embarrassed to do it, Josie begged, "Please fuck Miss May's pussy Rich! Please cum in her pussy so I can lick her pussy."

"Josie," exclaimed Miss May in a dramatic tone of disappointment. "You are in no position to talk the Rich like that. A slave like you should address him with respect. Call him Sir," demanded Miss May. "And don't sugar coat the task that you want to do slut. We all know you don't want to just lick my pussy. You want to lick his cum out of my pussy. You want to taste his hot creamy cum. Say it slave!"

Rich laughed at Miss May orders to Josie. He quickly added, "That's right sissy boy, let me hear you beg for my cum."

Josie could not believe what he had said. He could not believe Miss May was letting Rich join in on the humiliation. Josie was trying to process it all in his mind. He was not moving quick enough. A hard slap to his balls snapped him to attention. "beg slave," demanded Miss May.

Josie responded obediently, "Please Sir...please fuck Miss May's pussy so that I can lick your creamy cum our of it. I want to taste your hot creamy cum Sir."

Miss May slapped him again and ordered, "again slave!"

Josie begged more. Each word made him sink deeper into submissiveness and deeper into humiliation. The deeper he sank the more he aroused he became and the more he craved Miss May's domination and control.

Finally, Rich pushed his cock into Miss May's waiting pussy. He fucked her hard right over Josie's face. Miss May moaned and bucked and pushed against Rich's cock. Rich grabbed her ass and pounded her hard. Josie watched, knowing that he would never get the opportunity to fuck Miss May or even another girl like that. He was envious out how Rich fucked in a hard manly way. He was envious at how Rich made Miss May reach orgasm so quickly and how Rich exploded inside her without being ordered to cum or without even asking permission to cum.

Rich pulled his cock out of Miss May's pussy and a glob of his hot cum dripped onto Josie's face, landing right on his lips. "Oops, I dripped on her," commented Rich.

"That's o.k.," mused Miss May. "The slut loves it." Then Miss May positioned her pussy right over Josie's mouth and said, "Open up pretty. Here comes some more."

Josie opened his mouth and caught the cum that dripped out of Miss May's pussy. It was still warm from being inside her. Miss May watched the cum drip into his mouth. She complimented, "Good girl. Eat it all up." 

Rich laughed and remarked, "Unbelievable." 

After a few big drips came out of her pussy, Miss May sat down on Josie's face and wiggled a bit. "Get your tongue in there slut. Clean me out. Eat up all those sperrmies."

Josie obeyed like a good girl.

While Josie continued to lick her pussy, Miss May said to Rich, "Why don't you write out the check while my little whore finishes eating up all your sperm."

"Sure," said Rich, still amused at the scene before him. Rich retrieved his check book from his jean pocket.

"Make sure you write the check out to me," said May. She pressed her pussy harder against Josie's mouth and said to him, "It's all my money now, isn't it sissy bitch?"

"yes," replied Josie into her pussy.

"I don't think Rich heard you."

Josie yelled into her pussy, "Yes, It's your money."

Miss May laughed. "That's right slave. My money to spend how I want to. Keep licking up that cum. You own nothing now. You are the property now slave. My property and Mistress Sarah's property. You're just a worthless cum licker." 

Rich walked over to Miss May with the check in his hand. He was still naked but now his cock had shrunk. A drip of cum was on the tip, which did not go unnoticed by Miss May. She lifted herself from Josie's face and carefully position Rich's shrinking cock over his mouth. "Open up slut. One last drop."

Miss May squeezed Rich's cock and the drip of cum oozed out. It was not like a drip of water but more like a long sticky drip of glue. Miss May had to use her finger to detach it from Richs' cock. She pushed her finger into Josie's mouth and he sucked on it. "There you go princess, fresh from the tap. I know that's how you like it."



Discovering Mistress Sarah's World Pt. 09



Part 9 -- The Final Part

Chapter 23 Leaving Work

Josie's last week at work and concluding week of his normal life went quick. At work he spent time getting things in order for the next unlucky person to take over his job. Mentally he was already checked out of work. All he cared about was getting on with his new life. 

Miss May played a big part in ensuring his sissy life remained intact while he was back at work. Each day she sent him to work more feminized and enslaved. It started with the usual panties and stockings under his clothes but soon progressed to him wearing eye liner and a small amount of blush. On Wednesday she had him wear a pink dress shirt and by Thursday he was wearing women's business clothes. The clothes looked gender neutral but the labels were women's brand. 

Miss May also announced to Josie's that it was his time of the month. She sent him to the store Wednesday night to purchase tampons. It was a simple task but Josie found it to be extremely embarrassing. Two women were in the tampon aisle when he first entered the store. He cold not get up the nerve to walk down the aisle while they were there. Instead he milled around the store until the aisle cleared. When it was empty, he quickly walked into it and scanned the products. There were many choices of pads and tampons. After a few uncomfortable minutes of analyzing different boxes, he settled on a pink box with 10 tampons. Before picking the box up he glanced to the left and right to make sure no one was looking. Then he quickly swiped it form the shelf and headed to the cashier. 

His heart pounded as he walked through the store. He was already feeling embarrassed. He wanted to buy a few other things to make the tampons seems less conspicuous but Miss May made it clear that he was to only buy tampons. Josie tried to reason with himself that it was not a big deal and that guys bought tampons all the time for their wives and girlfriends. As much as he tried, these thoughts did not calm down his nervousness. What if one of his friends or neighbors came into the store, he thought. They knew he was not married. Josie was also very conscious that he was wearing eyeliner and a little bit of blush.

He walked to the register trying to look calm and relaxed but he could feel the redness on his face. The cashier acted normal when he put the tampons on the counter but Josie could barely look into her eyes. He quietly paid and then left the store. Josie was certain the cashier was laughing at him under her breath.

Thursday morning before work, Miss May had Josie bend over while she inserted the shell of the tampon just inside his boy pussy. It hurt at first, but then Miss May held the shell and pushed the "tail" forward forcing the firm cotton tampon out of the shell and deep into his ass. Josie felt a twinge of embarrassment at how good the cotton felt inside his ass. When his mind cleared of the sinful pleasure, he noticed the pretty feminine scent from the tampon package, which filled the small bathroom. The feminine scent combined with the feeling of the tampon inside him, mentally put Josie into a girly mood.

Miss May had him dress in pink panties, pink stockings, and a garter belt. She allowed him to wear socks to cover the stockings, but the socks had frilly lace at the top. Josie worried that if he sat down at work, his pants legs would ride up just enough for someone to see the lace. 

Concerned he said to Miss May, "What if someone sees the lace on my socks?"

Miss May laughed. "Well then they'll know you are a sissy. I'm sure they've figured it out already sweetie. Your feminine side is really showing this week."

Josie remained quiet. He knew there was no arguing with Miss May. She was enjoying putting him in these awkward situations. Miss May also dressed him in women's pants and a woman's blouse. Then she penciled in a thin line of eyeliner above his lashes and dabbed a hint of blush on his cheeks. 

Miss May handed him an individual tampon which was still in the pink plastic wrapping. "You're going to need this princess, just in case you have your period and need a fresh tampon."

The notion of him having a period was silly but it made his confined clitty twitch in his panties. Josie would be thinking about his period all day. He took the tampon and dropped it in his work bag. The tampon fell next to his small purse, which was filled with red lipstick, a small bottle of perfume, and a few make-up items. Josie was not allowed to leave the house without his purse on hand. He was thankful that Miss May allowed him to keep it inside his work bag and not in plain view.

On his way into work, Josie wondered how much truth there was to Miss May's comment that his work associates probably figured out he was a sissy. Miss May had kept him in an aroused daze all week and his feminine side was still a fantasy world to him. All week he was living under the pretense that no one at work would notice the changes in his clothes and looks. Now he wondered whether he was living under a false pretense the last two weeks. 

He looked into his rear-view mirror and did a reality check. The eyeliner was barely noticeable. The blush was a natural beige, but it was noticeable and gave his cheeks a natural feminine glow. Josie felt embarrassed, realizing that some people must have noticed the blush. He rubbed his hands over his cheeks, doing his best to blend the blush into his skin and make it less noticeable. Then there were his clothes. He was literally dressed head to toe in woman's clothes. His top and pants were neutral but they were still woman's clothes. Josie could not believe he let things go this far. He had wanted to keep his feminine life out of his work life. He hoped that he could resign with no hint of the life that he was going to embark on. Now he realized that this hope was compromised. He wondered what his co-workers thought of him now.

As he parked his car in the parking lot, he thought about abandoning work. He could come up with an excuse to not show up for the last two days. The more he thought about it, the more he knew it was not an option. It was not the proper way to leave the people he worked with for many years. He also knew that Miss May and Mistress Sarah would never approve of it. He was sure this was all part of their plan with him. He knew they got off on controlling and embarrassing him. It was exciting for him to know that his humiliation fueled their desires. The excitement motivated him to finish his day at work.

Josie was full of emotions during the day. On the surface he did the best he could to maintain his male identity. However, the tampon inside his boy pussy was weighing heavily on his emotional state. Feeling the intimate womanly item inside him all day created a stronger bond with his girl personality. The soft firmness inside him could not be ignored. Josie enjoyed this connection with womanhood that he was feeling. 

Friday Josie returned to work wearing another tampon and dressed similarly except for one change. His chastity device was removed. Mistress Sarah had sent a message the night before that Miss May could remove his chastity device for the day as a reward for his obedience during the week. Josie was thrilled at the news and was excited Friday morning when Miss May unlocked the device and removed it.

At first Josie thought it was a great reward. However, he quickly discovered it was pure torture. His pent-up arousal escaped the moment Miss May removed the tube from his cock. He drove to work hard as rock. He spent several minutes sitting in his car in the parking lot, willing his cock to shrink. When he finally calmed down he reached into his pants and pushed his cock back between his legs and pulled his panties tightly up around his waist to keep his cock in place. He figured this would be the only way to keep him from walking around all day with an embarrassing hard-on. 

About mid-way thought the morning, Joe received a call on his cell phone from Mistress Sarah.

"I miss you a lot slut. How's your morning going," asked Mistress Sarah.

Josie's cock twitched in his panties at the sound of his Mistress' voice. He replied, "I miss you too Mistress. Thank you for letting me out of my chastity device."

Mistress Sarah corrected him with the quickness and firmness of a drill sergeant , "It's not a chastity device Josie. It is a clitty cover. You will refer to it as a clitty cover from now on, understand?"

"Yes Mistress."

"Good girl. Are you enjoying your freedom?"

"It's nice but I am super horny. I had to tuck my clitty between my legs to keep calm."

Mistress Sarah laughed in amusement. "It's nice to see you are reverting to your natural state. It does feel so natural to be tucked away in clitty form doesn't it princess?"

"Yes Mistress," admitted Josie. 

"I am proud of you for realizing how you should be but I think Joe needs to make an appearance for his last day of work. Take him out for me now."

Mistress Sarah's voice and commanding tone were hypnotic to Josie. He almost forgot where he was. He was ready to obey without thinking. Thankfully he came to his senses for a brief moment and closed his office door. Then he unzipped his pants and pulled out his cock. It immediately swelled in his hands.

"I have Joe's cock in my hand," he replied into the phone.

"Mmm, that's my girl. Stroke him for me Josie. Make your man happy on his last day of work."

Josie obeyed. It only took a few strokes before precum was dripping out the tip. Mistress Sarah made him rub the stickiness all over Joe's cock until an audible squishing sound could be heard from the wetness.

"Can I make him cum?"

Mistress Sarah laughed at how quick the request came. "No silly. You are a desperate slut. That's how I like you to be and how I want you to feel the rest of the day. Lick your hand clean for me."

"Yes Mistress," replied Josie. He licked the stickiness from the palm of his hand. 

Mistress Sarah encouraged him through the phone, "That's it princess....lick up Joe's stickiness. I know you love it. I know you want to taste his cum. That will be your treat when you return home to me."

Josie loved how Mistress Sarah made him feel overly slutty and horny. "I can't wait to see you again Mistress. I already miss you."

"I know pet. You will be with me soon enough. I have lots of training to do with you. Now put Joe's cock away sweetie and get back to work."

Josie was disappointed for the fun to end but he obeyed. He zipped up his pants and started cleaning up his office. The afternoon went by quick for Josie. When he was ready to leave for the day he sent Mistress Sarah and Miss May a text indicating that he would be leaving in about 10 minutes. His phone rang immediately after the text was sent. It was Mistress Sarah.

Mistress Sarah's said, "Pet, another chapter in your life is ending. Are you sad?"

"A little sad, but I'm very excited about the next chapter."

"Me to princess. This is where the story starts to get fun."

Josie's cock was already swelling in his pants from hearing Mistress's voice. He sensed that she was not calling just for condolences. He knew there would be some task or assignment coming. His instincts were exactly right. Mistress Sarah ordered him to pull out 'Joe's' cock again. Josie shut his office door one last time and obeyed. He started stroking on her command.

Following Mistress Sarah's instructions, he brought himself to the edge several times. When Mistress Sarah was convinced that he was in a complete state of arousal she said, "Josie, I want you to have nice pretty glossy lips when you walk out of work today. My princess needs to leave with a great impression, don't you think so slut?"

"Yes Mistress," he replied obediently. 

"That right pretty. You know what to do. Squeeze a bit of cum from Joe's cock and make your lips nice and shiny for me."

With all the edging, it was an easy task to do. A few squeezes on the tip of his cock caused a small gooey string of cum to ooze out. Josie let it drip onto his fingers. Then he rubbed the cream over his lips. He updated Mistress, "My lips are nice a shiny now."

"One more time pretty pet. Put another coating of cum on your lips. Don't be shy about it."

"Yes Mistress." Josie obeyed her command. Now his lips felt wet and sticky.

"Good girl. Now walk out of there nice and proud Josie. I will see you soon."

Josie said his goodbye to Mistress Sarah and then headed out of his office. He did not have a mirror so he did not know what his lips looked like. He hoped the cum blended in well. It was his goal to get to his car as soon as possible without drawing attention to himself. This proved to be an impossible feat on his last day of work. The first few people he passed did not bother him and did not make any strange faces at him so he assumed that either the cum blended in well or that they just did not notice.

Before he reached the elevator one of his female co-workers intercepted him to say her good-bye's. She hugged him and even gave him a kiss on the cheek. Josie was paranoid about his cum covered lips. While his co-worker hugged him he quickly licked his lips. A naughty and embarrassed feeling filled his body. He could not wait to get home to Miss May.

He endured a few more good-bye's before finally getting to his car and heading home. An almost empty apartment greeted him. With the exception of a few shopping bags on the living room floor, the place was empty. Whatever was not sold at the sale had been packed in the moving truck or taken to the local Goodwill store. Miss May had proudly informed Josie that she went on a shopping spree with all the money earned from the sale. 

She was excited to show off her new items. She immediately ordered him to strip to his panties and bra and kneel before her. Before she started the show Miss May ordered, "stroke your clitty for me sissy. I want you to be excited from all the things I bought with your money."

Josie slowly rubbed his clitty through the soft panties. It swelled instantly. He was happy to be out of his chastity and able to play with himself. Miss May modeled dresses, sexy club wear, and lingerie. She looked amazing in each outfit. Josie enjoyed seeing her wearing the different lingerie and tight sexy outfits. Miss May made it a point to emphasize how she used his money to buy the clothes. Then she thanked him mockingly at how his submission was giving her a better life. In between outfits she made him kiss and lick her feet and her ass. While he licked her ass, she teased, "This is your place in life slut...beneath a woman, worshipping me, worshipping Mistress Sarah, and giving us whatever we want."

Josie continued to lightly stroke his clitty while he worshipped Miss May with his tongue. His arousal was high and still growing. Miss May's words were hypnotic visions for Josie. His mind absorbed them and held on to them. With no job and all his possessions sold or given away, he easily bought into Miss May's visions. He was happy with his new place in life.

Miss May showed off more than just clothes. She modeled bracelets, necklaces, rings, earrings, and shoes. She even bough herself a new camera. Miss May also showed Josie bags of expensive clothes and accessories that she bought for Mistress Sarah. She showed no restraint with spending all the money. All Josie's possessions had been sold off and the money used for a lavish spending spree for his Mistresses.

She saved this best for last. With a gleaming smile she produced two sets of diamond jewelry. Both were complete sets that included diamond studded rings, diamond pendant necklaces and matching earrings. The diamonds glowed with magnificent brilliance in the lights of the apartment. 

"Aren't they beautiful," beamed Miss May.

"Yes, they look amazing."

Miss May picked up the diamond pendent on the left. "This set is mine. The other set is for Mistress Sarah," she said as she secured the necklace around her neck. Her fingers toyed with the pendent and it shimmered in the light.

"It's beautiful," complimented Josie. 

"Much nicer than your car don't you think," teased Miss May.

"Yes Mistress," replied Josie submissively..

Josie was keenly aware that Miss May's excitement was about more than just the shopping spree. The shopping spree represented complete dominance over Josie. Josie had heard about financial domination before but he never understood it. He never imagined how a guy could let that happen to him or even enjoy it. Yet, he was in that very spot right now. He was stroking his cock while Miss May deliberately showed off every item she bought with his money. 

His cock was raging hard. Miss May was pushing him into a deeper, newer submission. He could not stop it. The thrill he was experiencing at the moment had a strong hold on him and he did not want to let it go. He lived in the moment, not caring about what would happen next, and not even thinking that Miss May could just walk away anytime leaving him with nothing.

Chapter 24 Returning to Mistress Sarah

Josie's heartbeat quickened when he turned the moving truck onto to Mistress Sarah's road. A new life awaited him at the end of the road. He was both excited and scared about his future. He knew Mistress Sarah would open his eyes to a whole new world. She had already taken him into a wonderland full of pleasure that he never new existed. He was excited to experience pure sexual bliss with her. 

Josie was also aware that once he set foot inside her door, his freedom and identity would disappear. He knew that her presence alone rendered him weak and helpless. He could not resist her beauty and commanding power. She was clever and manipulative and could read him like an open book. He would be putty in her hands and do anything she wanted. It scared him at how her desires and the need to please her were wired straight to his brain. 

Even with the risk of losing everything and being completely emasculated and humiliated, he could not stay away from her. The pleasure and excitement that he experienced with her far outweighed the risks. Josie followed Miss May up to the door. He was so excited and nervous about seeing Mistress Sarah again that he did not even think twice about the fact that he was completely feminized in public. In the morning, Miss May had ensured he was in full feminine attire, including his wig, false tits, and 6 inch heels. At the last rest stop, she spent time touching up his make-up and lipstick. She wanted him to look perfect for Mistress Sarah.

The skirt she had picked out for him was so short and tight, that he could only walk in short steps. Josie was proud of himself at how easily he could walk in the heels. It took some practice but he mastered the right step and balance. Miss May walked inside without knocking and Josie followed behind her. They were immediately greeted with big hugs from Mistress Sarah.

Mistress Sarah beamed, "I missed you girls. How is my pet?"

"Very good Mistress. I missed you a lot," replied Josie in his girl voice.

"You look stunning princess. Miss May did a fabulous job with you."

"Thank You," replied Josie. His face blushed at the compliment. His cock started to swell. He was excited and aroused to be around Mistress Sarah again. It only took a second or two before his cock was bulging against the hard chastity device, trying to break free. The hard plastic held firm. Josie grimaced and waited for his cock to retreat.

Mistress Sarah gave Miss May a big hug and deep tongue kiss. When they broke the kiss, they looked at each other with hunger in their eyes. They had been away too long. Josie thought for sure they were going to strip down in front of him. Instead, Mistress Sarah dismissed Miss May saying, "Go find Nellie. Have him call some of his boyfriends to unload the truck. I have catching up to do with Josie."




Discovering Mistress Sarah's World Pt. 09



With disappointment in her voice, Miss May responded, "Yes Mistress." Then she hurried off through the house looking for Neil.

Mistress Sarah grabbed Josie's hand and said, "Come with me pretty pet."

Josie followed without comment. He could barely contain his excitement. He knew Mistress Sarah had something exciting planned. She led him down a hallway and into a room he had never seen before. The room had steel cabinets lining the walls. A few odd shaped padded benches were scattered around the room. Josie was sure there were many kinky purposes for the benches. In the center of the room hung two chains with black fabric loops attached to each one. Josie did not understand the purpose of the chains and fabric but he would soon find out.

Once in the room, Mistress Sarah turned to him and smiled devilishly. She moved close to Josie, her perfume was sweet and intoxicating. Mistress Sarah looked into Josie's eyes and slowly started unbuttoning his blouse. Quietly she said, "You look super sexy Josie. It's a shame to undo all this but I have other plans for you tonight."

Josie remained quiet as Mistress Sarah slowly undressed him. She peeled off his blouse. She kissed around his neck, undid his bra and slid it off. Josie felt like a girl who was being ravished by her date.

Mistress Sarah tweaked his nipples and sucked on them. Then she whispered, "You have beautiful tits princess."

Josie's body shivered. "Thank you," he whispered back.

"Let's get you out of that tight skirt. I want to see your pretty ass."

Mistress Sarah unzipped the back of the skirt and helped Josie shimmy it off. Her hands rubbed over the black satin panties that Miss May had dressed him in. She squeezed his ass and rubbed his crotch. When she felt the hard chastity device, she smiled and said, "Get used to this pretty. You will be wearing it a lot. It's the best way to keep those silly boy tendencies from surfacing, don't you agree pretty?"

"Yes Mistress," replied Josie. The comment made his cock swell again. He should have been running scared at the implication of being locked up on a permanent basis. However, instead his body was swarmed with arousal. He loved that Mistress Sarah was taking complete control of him. Mistress Sarah pulled his panties down and admired the device. She gave it a quick tug and giggled, "your clitty looks so small and cute." The arousal continued to swarm inside Josie.

Mistress Sarah pulled off his heels and peeled down his stockings. Then she tossed his wig to the side. When he was completely naked it she took him over to the chains and had him reach up as high as he could and grab each chain with each of his hands. Then she carefully tied his writs to the chains. When he was secured she slapped his ass with her hand and ordered, "pull up!"

Josie hesitated and looked at her confused. She slapped his ass again. This time it was a harder slap and harsher tone in her voice. "Pull up slave and put your legs through the fabric loops."

Josie tried to obey. He pulled his body up. The chains swayed, making it difficult to put his feet through the loops. His feet fell back down to the floor. He struggled again to do it.

Miss May watched with amusement. "Come on slave, do it!" She was amused seeing her naked slave struggle to get in position. After about a minute she left the room. On her way out she said, firmly "I'm going to change into something more appropriate. You better be in position by the time I come back."

Fifteen minutes later when she returned, Josie was in position. It took him several minutes but he eventually figured it out. He pushed his feet and legs through the fabric loops until the fabric rested half way up his thighs. Then it was clear to him, that the chains and fabric were nothing more than a swing.

Josie hung freely on the swing while Mistress Sarah walked around him. She wore black heels that shined just as lustrous as the latex mini dress that she was wearing. Latex was his weakness and Mistress Sarah knew it. Josie had confessed to her many times at how incredibly sexy and dominant women looked in latex. Her hair was pulled back into a tight bun, further emphasizing the dominant look. Mistress Sarah's bulging tits added to the sexiness and to Josie's demise.

Mistress Sarah silently circled Josie. He was still breathing hard from the struggle with the chains. She liked this. His muscles bulged from the physical exertion of lifting his body over and over again. Although she liked girls and preferred her boys to be soft and pretty, she did take gratification every now and then to see their hard shell appear. 

The chains and muscles provided a nice image. Her pet...her animal was restrained and under her control. Mistress Sarah could feel her pussy heating up from the sight of her helpless pet. She was rather amused that even with his muscled bulging, he was still not completely a male creature. His face was still painted with make-up and his cock was restrained. 

Mistress Sarah squeezed his biceps and said, "The boy in you wants to come out...", her hand slid down to the chastity device and squeezed it, "... but all I see is a girl with muscles...." She traced her fingernails over his thin arched eyebrows and down his blushed cheeks. "You may have muscles but there is no hiding that pretty face."

Mistress Sarah grabbed his chin and raised it up and then gave Josie a deep tongue kiss. Her tongue was forceful and probing inside his mouth. Josie's insides melted at the powerful and intimate kiss. His tongue softly rubbed against hers. He knew not to be as aggressive as her. He felt completely submissive hanging on the swing with his wrists tied above his head and her hand firmly gripping his chin while she took pleasure in him. He did not want the kiss to end but eventually she pushed him away, causing him to swing back and forth.

Mistress Sarah let out an evil laugh. She had a look of hunger and dark dominance in her eyes. The kiss had sparked a deep arousal and desire to control. It was a pent up desire that had been waiting to break free. She walked behind Josie and abruptly stopped him from swinging. She reached around and pinched his nipples hard and bit his ear. Just as Josie gasped from the sudden paid she whispered into his ear, "You are all mine slave!"

Mistress Sarah attached another long chain around Josie's left ankle. She made a loop around his ankle and secured it with a clip. She pushed the other end of the chain through a large eye hook in the ceiling above the swing. She pulled on the chain, causing his left leg to bend behind him. Then she pulled his right leg behind him and looped the other end of the chain around his right ankle. 

Next she pushed an open mouth gag into his mouth. The gag had a metal frame that forced his mouth to be open. Mistress Sarah, tightly secured the attached rubber straps behind his head to ensure the gag did not fall out. Mistress Sarah stood in front of him with her evil smile. She laughed and said, "You are all mine now Joe."

Josie was confused at why she referred to him with his male name. She walked over to a drawer and pulled out a piece of cotton and make-up remover. She took her time soaking the cotton with the remover. Then she slowly walked over to him still smiling devilishly at him. 

"Let's get this silly make-up off you." Mistress Sarah swabbed the cotton over his face until all the make-up was removed. Then she wiped away his lipstick. By now, Josie was slobbering from having his mouth forced open so long. 

"You're a mess Joe," teased Mistress Sarah. She wiped the drool with her finger and then rubbed it on his nipples. "It is quite embarrassing, isn't it? Drooling all over yourself. That is the point of course. I do like embarrassing you and humiliating you Joe."

Mistress Sarah walked behind him and roughly pushed her finger into his ass. Joe yelped and flinched at the sudden intrusion. Mistress Sarah grabbed his hair and pulled his head backwards. "I am going to have so much fun raping your ass Joe. Your ass belongs to me! Your mind belongs to me! You are my property slave!"

Joe's heart was now pounding hard. He had never experienced this side of Mistress Sarah before. Her tone was filled with a hint of evil. He did not know what to think. He was fearful but his cock was growing and pushing hard against the chastity device. He was overcome with arousal. The fact that he could not get fully erect was maddening.

"Are you wondering why I am calling you Joe," she asked. She did not wait for an answer. "I am calling you Joe because I want you to be Joe right now. You will be what I want you to be when I want you to be. You are my slave and slaves do not think, they do! I want you to swing right now."

Mistress Sarah pushed Joe and he swung back and forth. She laughed. Then she said, "I want you to stop!" She abruptly stopped him from swinging. She laughed again. "You are under my complete control. Get the point?"

"Yes," mumbled Josie through the gag.

"From now on you are blank. You are not male and you are not female. You are genderless. You simply exist as a being. You exist as my slave. Each day I will decide how to shape and mold you. I will decide what your name is. I am losing interest in Josie. It is much too similar to your male name. Maybe you will be Jenny or Becka. We'll see. Some days you will be human, some days you will be my pet, and some days you will simply exist as an object or toy for me to play with. Do you understand slave?"

"Yes Mistress," shouted Josie as best he could.

Once again Mistress Sarah was introducing mind blowing thoughts to Josie. She was tearing down what he thought was his future and re-creating a new path for him. It was this constant change and unknown that made Mistress Sarah so exciting. In less than an hour she had him fully restrained and gagged. His cock was locked up and she had spouted off rules and conditions that took away all his rights and forced him to completely surrender to her. It was clear to him that he was now a real slave and yet at that moment he felt completely free!

The End.



Discovering Mistress Sarah's World



Joe knew the feminization was going to continue and he kept telling himself that at some point he would put an end to it. The problem was the he was having so much fun that he kept pushing the ending point out. His will power was no match for Mistress Sarah's sexual power and carefully planned incentive system. She was transforming Joe into her sissy slave and he could not resist. 

Even his mind was transformed. Mistress Sarah encouraged him to think from a girl's perspective. When he commented about how nice her breasts were, Mistress Sarah scolded him for thinking like a man. She said, "Don't tell me I have nice tits. Say that you wish you had tits like mine." 

It felt odd at first for Joe to make a comment like that. However, Mistress Sarah continually corrected his comments and made him repeat things from a female point of view. His mind was slowly reprogrammed to think this way and each week the female point of view became more accepting to him and more real to him. The 'Josie' persona was growing and blossoming inside him.

So as he kneeled naked and horny before Mistress Sarah, with the taste of cum in his mouth, it was not a surprise to hear Mistress Sarah ask him if he was ready for his transformation. The answer was obvious. In fact they both knew that the transformation was already well under way. Joe obediently answered, "Yes Mistress. Please transform me into a pretty girl."

Mistress Sarah walked behind Joe and rubbed her hand over his round ass. "Mmmm. So nice to hear you say that Josie. You've come a long way, haven't you? You used to be so resistant, but now you want it don't you pretty? You've learned how it exciting it is to be a sissy, haven't you?"

"Yes Mistress," replied Joe with total surrender.

Sarah's pussy tingled and dampened at Joe's admission. She was thrilled to know that she had conquered the 'man' inside him. His acceptance of his sissy state was proof of Sarah's control and power over him.

"Good girl, Josie. We are going to have so much fun this weekend. A weekend of girl fun. Let's start with some sexy delicates panties. Follow me kitten."

Joe crawled after Sarah, following her up the stairs and into her bedroom. Once in the bedroom Mistress Sarah had Joe stand up and face the bed. An assortment of lingerie and accessories covered the bed. Joe's cock twitched as he took in the variety of feminine items that covered the bed. Everything looked soft and pretty. Mistress Sarah selected a pink teddy from the bed and held it up for Joe to see. She smiled and said, "I this will look so sexy on you Josie."

Joe had never worn a 1 piece outfit before. It had always been just panties and stockings. The teddy was very pretty and feminine with ruffles and lace. Joe stared at the delicate item and imagined how sexy it would look on him. Being in her presence and knowing how excited she was for his feminization, made it easy for him to want to wear it.

Mistress Sarah helped Joe slip into the teddy. Joe enjoyed the feel of the soft fabric encasing his body. He enjoyed the snugness of the teddy against his crotch and balls. Next she handed him white stockings. Mistress Sarah watched with great pleasure as her sissy slave pulled on the stockings and attached the garter clips that dangled from the teddy.. It was thrilling to see a man be so dainty and cute. His demeanor was docile and slow. He was hesitant and shy. Mistress Sarah loved this effect on Joe. She could tell that he was slipping into an erotic subspace and this made her pussy drip.

Mistress Sarah made Joe slowly turn and curtsey for her. She thought his ass looked cute in the tight teddy. His excitement was obvious not only from the outline of his hard cock in the lacey fabric, but also from the large wet spot that turned the thin fabric transparent right at the tip of his cock. Seeing the pinkish color of his cock head through the transparent fabric was a hot and erotic image that caused Sarah's pussy to quiver with need. She ran her fingertip along the underside of Joe's cock, causing it to twitch and send chills through his body.

She commented, "Seems like my little princess has wet herself with excitement. We're going to have to do something about this big clitty dear. It's so vulgar swelling out like that. It needs to be tucked away like a real girl's pussy. You're much too excited now princess. I'll deal with it later."

Mistress took a step back and pulled up the bottom of her tight dress, exposing her pussy. She placed one foot on the top of the bed, giving Joe a nice wide view of her sex. Then she said, "I'm a little wet myself Josie you need to attend to my pussy."

Mistress Sarah pushed down on his shoulders. Joe did not resist. He had dreamed of tasting her pussy for months and was overjoyed to finally get the opportunity to please her with his tongue. He kneeled in front of her and gazed at her bare pussy. Her lips were swollen and puffy. He could see them glistening with wetness and he could smell the strong scent of her arousal. The sights and scents of raw sex triggered his carnal instincts, awakening a deep hunger for his Mistress. 

Mistress Sarah pushed his head into her wet mound. Her wetness covered his face. Joe pushed his tongue deep into her warm folds, and tasted her sweetness. He breathed in her primal scent. 

Mistress Sarah moaned, "mmmm. That's it sissy. Enjoy my honey pot."

Mistress Sarah held his head against her mound while she grinded her pussy into his face. There was no escape for Joe. He could barely breathe as he serviced her pussy. He enjoyed being held tight against her sex and feeling her control. He reveled in his helplessness as she humped his face. 

Mistress Sarah moaned and grunted with pleasure. "Yes...fuck me with your sissy tongue...show me what a good tongue slut you are....yes....deeper slut...mmmm"

Joe pushed his tongue in deep, exploring her insides, and teasing her clit with his tongue. He could not get enough of her juices. The more he explored the more intense her moans become. Soon Mistress and slave melded together into a natural fucking rhythm. 

Joe's cock strained against the tight silkiness of his teddy. Although there was no one touching his cock, it was completely aroused and sensitive just from the mental joys of orally pleasuring his Mistress. He could feel the slightest movements of the silken material rubbing over his sensitive shaft and head and this was bringing him close to orgasm. The soft material also rubbed over his nipples. This was not a sensation he was used to and it even furthered his excitement. He strained to hold back from orgasm, for he knew that his orgasm was forbidden without his Mistress's consent. Her pleasure and her orgasm were all the mattered.

Joe barely managed to control himself as he fucked his Mistress with his tongue and face. He stayed in rhythm with her, moving faster and faster as she did. Her orgasm was obvious, as Joe could feel her pussy and body shiver with waves of pleasure. Her grip around his head tightened as her orgasm intensified. His tongue, mouth, and nose were smothered into her warm wetness until the orgasmic pulsing subsided within her.

Joe was almost ready to pass out from lack of air, when she finally released him. He took a deep breath, recovering himself. Mistress Sarah was also breathless from the intense orgasm. She sat on the edge of the bed, getting her breath back while Joe kneeled at her feet.

"Mistress is very pleased with your tongue," said Mistress Sarah with deep breaths.

"That was incredible," said Joe, confirming the obvious.

"Yes. I've been waiting for that for months Josie."

"Me too. You are so awesome Mistress Sarah," complemented Joe.

Mistress Sarah smiled at her slave's compliment. "Good girl."

Mistress Sarah was pleased and excited to see her slave kneeling and fully aroused at her feet. She loved that he had given her an orgasm, without expecting one in return. It proved that his training had worked and it confirmed her control over him. 

Mistress lifted her foot and lightly rubbed the tip of her shoe along the underside of Joe's cock. He breathed deeply and his eyes closed as wonderful sensations filled his body. He was still fully aroused.

"I'm so proud of you for not cumming Josie. It's so exciting to tease you like this princess."

"I like it to," commented Joe. 

"I know you do slut. I know you love to be horny all the time and I'm going to keep you that way all weekend. Your horniness makes you weak and trainable and that's the way I need you to be this weekend. When you leave in a few days you will be a different person Josie. You will be soft, prissy, pretty, and completely submissive to me. You will be like this not only on the outside, but also on the inside. Your mind is mine now Josie and I am going reprogram it to think like a girl Josie. That's exciting, isn't it.?"

Joe surprised himself at how quickly the word, 'yes' escaped his lips. He should have been scared, nervous, and even embarrassed at the things Mistress Sarah presented to him. The man in him should have been running for the door but instead he remained kneeling and his excitement grew. His arousal intensified the more Mistress talked about training and transforming him. Her words were magic. They held a power that entranced and hypnotized him. He was wrapped up in her world, oblivious to the outside world. 

Mistress Sarah's toe continued to trace his cock through the soft material of the teddy, keeping Joe in an intensely aroused state. Softly she said, "I'm glad we had this alone time together pet. It was important for us to bond like this. Soon Miss May will be here and we will resume with your training."

Joe was so close to the edge the way he was being teased by Mistress Sarah's toes and her powerful words. He was concentrating so hard on not cumming that he could not talk. He simply let Mistress Sarah's words sink in. He was glad to hear that Miss May would be coming. He could not wait to meet her in person. She had been a key part of his training up to this point.

Mistress Sarah made Joe lie on the bed and then she continued to tease his cock and talk about his transformation and how she wanted him to be completely submissive and pretty for her. She stroked his cock in a slow rhythmic pattern. Her voice was soft, soothing, and steady. Together, her voice and teasing put Joe's mind into a hypnotic and mesmerized state.

Mistress Sarah purposely asked many questions about his feminization and obedience that all required a 'yes,' answer from Joe. Each time he agreed with her, his mind opened up more for her control. By the time Miss May arrived, he was completely under her spell and eager to continue his feminization.

END OF PART 1



Discovering Mom's Secret



My name is Andy. For as long as I can remember, it has just been my mom and I. She married in her late teens, only to divorce my good-for-nothing father a few years later. I came along during the early years of the marriage, and my mom raised me by herself, with no help from my deadbeat dad. I grew up in the Midwest, but my mom moved us to Atlanta when I was in my teens. I am now 22 and my mother is 40.

My mother worked a series of clerical jobs during my early teens, and we struggled from month to month to pay the rent. In the last few years however, our economic situation has improved dramatically. Mom has started traveling around the country a couple of weeks each month, on what she claims is "public relations" work. I was puzzled by her new job at first, because my mom never even graduated from high school, but I enjoyed our new-found wealth so much that I didn't ask many questions.

My mom has always been a beautiful woman. Even at 40, she still maintains her youthful looks. She is about 5 feet 6, with blonde hair and natural D cup breasts. (I stole one of her bras and checked.) She constantly works out, and possesses a tight body that a woman ten years younger would kill for. All during my youth, she constantly had men in her life, who would take her on exotic vacations and buy her expensive presents. Somehow though, these relationships never seemed to last more than a month or two, and then a new man would enter her life. This all ended when she began traveling around the country doing her public relations work a few years ago.

Anyway, as the money kept rolling in, I started getting more curious about just exactly what mom did on her business trips. At first she was evasive, but then she opened up a little and said that she accompanied men to business and social gatherings. She hastened to assure me that these men were perfect gentlemen who just needed a beautiful woman to impress their colleagues or bosses, and that nothing inappropriate never happened. Being a naive young man, I bought her story hook, line and sinker.

My eyes were opened to the true nature of my mother's work one day when I received a manila envelope in the mail. Inside was a letter and an envelope with what felt like pictures inside. The contents of the letter hit me like a ton of bricks when I read it. I quote:

"Dear Andy: I am a longtime acquaintance of your mom's. We see each other every time she comes to Philadelphia. She has mentioned you many times in the course of our conversations and that is how I know of you. When your mom first told me that she had a grown son, I got incredibly turned on. You see, she informed me of this while we were in the middle of an incest role-play scenario in which your mom was sucking my cock as I pretended to be her son. You see, Andy, your mom does not work for a public relations firm. Instead she works for an escort agency called Intimate Pleasures. Men such as me hire her out at $400 per hour to fulfill our fantasies and have incredibly nasty sex with. I have seen your mom at least a dozen times in the past few years, and we have done it all. Besides giving me some incredible blow jobs, your mom has let me fuck her in the ass, come on her face, and swallowed my cum more times than I can count. Your mom also enjoys being the center of attention at small parties I host, taking on each of the men that attend, usually between 6-10. I have personally seen your mom take three cocks in her at once, while 3 other men jerked off on her face." 

"I am sure that this news must come as quite a shock to you, but I assure you that I am telling the truth. If you don't believe me, you can check out the escort agency's website or even better, look at the photos I have included in the envelope. Why have I told you this? Simple. I am very turned on my the idea of incest, and I would love to know that you and your mom were having sex. I must tell you, that she REALLY got into our incest role-play fantasies, so I think you might have a chance at seducing her if you play your cards right. Good luck! -- Mr. X"

I stared at the letter in shock and disbelief. I desperately wanted to not believe it, but it all made sense. This was how my mom made all that money every month. She was working as a whore! I started to throw the envelope and the letter away, but then my curiosity got the best of me. With trembling hands, I opened up the smaller envelope that held the pictures. There were about 15 of them in there and they were definitely of my mom having sex with different men. There were a couple of shots of her posing nude that got my cock rising in my shorts. Geez, does she have an incredible body! There were several more that showed her on her knees, with various cocks in her mouth, including one photo with the largest black cock I have ever seen. That sucker must have been 12 inches long! Several more photos confirmed the letter's contention that my mom liked group sex, as they showed her with cocks in the mouth, ass, and pussy at the same time. The final two photos were the most amazing: they showed my mom's face literally covered with cum. What made it worse was that she had a huge smile on her face.

Still not believing what my eyes had seen, I got on the internet and went to the web site that Mr. X had mentioned. Sure enough, there was my mom, wearing a string bikini and calling herself "Taylor". The web site mentioned that her rate was $400 per hour and that she was their most uninhibited and popular escort, specializing in a BBBJTC, which I soon learned stood for "bareback blowjob to completion".

At this point, I tried to get mad at my mom for being a lying whore, but the erection in my pants was dominating my thought process. I whipped out my cock, and while looking at the nasty pictures of my mom, began jerking off. As I did so, I wondered what it would be like to actually fuck my own mom. As soon as this thought entered my mind, I exploded and shot cum all over the photo of my mom with a cock in each of her holes.

After quickly cleaning up my mess (as well as the photo I had stained), I started thinking about what to do next. Should I toss everything, or confront my mom? If I confronted my mom, what would her reaction be? Sure, she was a wild woman who loved sex, but I was her son. She had never even hinted about wanting to fool around with me, even during all those years we were alone. She was due back from her "business trip" to Philadelphia tomorrow, so I didn't have much time to decide what to do. In the end, I decided to play it cool, and see if she would admit on her own what she was really doing for a living.

The next day, I picked my mom up at Hartsfield airport, as I always did at the end of her trips. She greeted me with a big hug, just as she always did. However, I now looked at her in a totally different light, not being able to get the image of those nasty photos out of my mind. I found myself staring at her large breasts, her long legs, and especially her beautiful face, which I imagined covered in my cum. I found myself getting hard as I drove us home, and shifted uncomfortably in my seat. Mom noticed my discomfort and my silence and asked if everything way OK. I just nodded and kept on driving.

When we got home, mom announced that she really needed a long shower. I imagined that she needed it because she still had loads of cum all over her body from a hard week of fucking strange men for money, but of course I didn't mention this to her. As she showered upstairs, I made up my mind. I would leave the photos out on the table and take it from there. 

Mom soon came back downstairs, with a towel in her hair and a silk robe on that hugged her womanly curves. Damn, why didn't I ever notice how sexy she was before? She sat down at the table and started asking me about my week and whether I had deposited the money that she had sent home ahead of her. As she chatted and dried her hair, she noticed the envelope on the table. She asked what was in it and I told her to take a look. When she did, her eyes quickly grew as big as saucers. Glancing at me, she quickly leafed through all of the photos in the packet. When she was done, she looked at me with the saddest eyes I have ever seen. Almost crying, she asked me where I had gotten the pictures. I told her about the letter I had received from Mr. X from Philadelphia and how it told everything about her secret lifestyle. I handed her the letter and she began to read. When she finished, she crumbled it up and threw it in the wastebasket. "Goddamn that Fred Jones!", she screamed. "I am going to kill him next time I see him!" With that, she broke down and started crying.

I then informed mom that it was time for her to level with me. First, I asked her if everything in the letter was true. She nodded that it was. I then asked her why she did this for a living and she replied that it was the only way she knew how to make a sufficient amount of money. Looking me stright in the eye, she declared that she made over $100,000 last year only working two weeks per month. I wanted to know if she enjoyed her work as much as the letter and the photos indicated and she once again nodded yes. She explained that she was always a very heavily sexed woman, and this was a way to make a good living while taking care of her needs.

At this point, I got a little more inquisitive. I asked her specifically what parts of her job she enjoyed the most. At first she hesitated, but then I informed her that I had a right to know everything. She proceeded to tell me that she loved to suck a man's cock and swallow his cum. She also mentioned that she loved really large cocks and liked the feeling when she had a cock in her ass and pussy at the same time. She also said that she loved being an exhibitionist at small parties and that she felt empowered when several men wanted her at the same time. She also volunteered that she had gone out on several two-girl calls, and found that she enjoyed having sex with other women as well.

As mom detailed her wanton ways, I pulled my cock out and slowly began masturbating under the table. I then informed her that she still hadn't discussed one aspect of her job and that was the role play fantasies, specifically the mother-son fantasies that she took part in. She replied that it was all a part of her job, that different men had different kinky fantasies and that she did her best to go along with whatever it was they fantasized about. With that, I stood up from the table and continued my masturbation. My mom's eyes grew wide and she tried to get up and leave. I roughly told her to sit back down. Somewhat to my surprise, she did. I then told her to take off her robe and show me the body that she had shown so many other men. She protested, but quickly complied after another stern look from me. My mom now sat before in all of her naked glory. I couldn't help but stare at her beautiful tits, and the sexy tan lines on her body. My mom then surprised my by squeezing her nipples. She then moved a hand down to her crotch and began playing with herself. My god! My mom was as turned on as I was! I quickly walked over to where she sat and waved my cock in her face. She smiled at me and asked me what her little boy wanted from his mommy. I told her to suck my cock and she leaned down and began gently sucking the tip of my cock.

I stood at the table transfixed as my mom began giving me the best blowjob of my young life. As she sucked, she reached one hand around my back and slowly inserted a finger in my ass. "Just a little trick of the trade", she mumbled between sucks. That did it. I exploded into her mouth like Old Faithful at Yellowstone National Park. I heard my mom gulp a couple of times as she swallowed it all down. When I was finished, she stood up, took me by the hand, and led me upstairs to her bedroom. On the way, she told me to fetch the digital camera if I liked. We spent the rest of the weekend sucking and fucking in every position imaginable, including a couple that weren't already documented in her photos. As I drove her to the airport Sunday night for her next trip to Philadelphia, she gave me a wonderful blowjob in the car. I asked her at the drop-off point if she was still going to kill Mr. X when she saw him. She shook her head no, and replied, "I can't believe the bastard won the bet!"