0 comments/ 58987 views/ 4 favorites Dress Up By: StevesPet76 "The hunting sucked today." I settled more comfortably in the easy boy. "But this evening more than made up for it." James flashed me a smile and laughed softly. Gently I raised my foot and set it on his shoulder. His kissing and massaging helped me relax the day away, all the miles walked in the woods, the cold, and then the blinding excitement of what I found when I returned home. His hands deftly, expertly caressed the arch of my foot, my ankles. His soft lips kissing my toes and the bridge of my foot. Leaning back I closed my eyes and sighed. His applications had a medative effect on me. I noticed a tingling sensation beginning between my legs as my mind drifted... I pulled into the driveway and parked behind James' car. Looking at my watch I noticed that it was only half past three. I know James is not expecting me until six at the earliest. Yawning I rubbed my neck. I had been up since well before five am this morning when he surprised me with a big hunter’s breakfast. I smiled remembering the how sweet it all was. Belgian waffles with French vanilla ice cream, fresh strawberries, melon, and a steaming hot cup of coffee with French vanilla creamer, my favorite. There was a beautiful long stem rose in a small glass. I pulled the rose off my dash board and smelled it a soft romantic smile curved my lips. We had beautiful sex this morning, it almost made me want to stay home in bed. But with a soft kiss and gentle caress James insisted that I go have some fun, while he cleaned the house. He helped me into my hunting gear and kissed me gently as I got into my truck. Hmmmm... My breasts were aching for his touch, but my body was aching for a hot bath. I laughed out loud to myself. "Women can be fickle." "James I'm home." I called walking into the living room. It was quiet and I did not see him any where. Maybe he is taking a nap. That's cool, I though my heart beginning to race. I had been thinking all day what I could do to return this mornings adventure, now is my chance. I quietly walked to the bath room. The light was out and the door stood ajar. Flipping the switch I took down a towel and soap. Leaving them sit on the sink, I headed quietly towards the bedroom, the door was closed I stood outside listening. There was no sound from inside. An evil smile curved my lips. I’ll dash in and grab my cloths, and after my bath I’ll give him a wake up call he won’t forget for a while. Slowly I turned the door knob and pushed the door open. The sight I saw threw me into a state of total shock. James was sitting on the edge of the bed, slowly seductively sliding my black thigh highs up his leg. He fastened the stocking to the garter hanging down from my favorite black teddy. Slowly he was running his hands down his now stocking clad leg, caressing the feel of the slick material on his ankle and gently rubbing his foot. Moaning softly he brought his hands slowly back up his leg. I could see his taunt muscles rippling through the thin fabric. I stood slack jawed in disbelief at what I was seeing, but at the same time there was a heat growing in my abdomen. He moved slowly and sensually as he pulled the other stocking on and snapped it to into place. Standing now at the foot of the bed he smoothed the black fabric of the teddy. Turning towards the door I don't know who was more shocked to see who. "Brenn..." he stammered "you’re ... your home early." His face flushed a deep crimson, and he quickly bent to unsnap the garter. "No" I almost shouted. He jumped and looked at me. Taking a deep breath to get a hold of myself, I met his quizzical gaze. I walked over to the chair and sat there looking at him. Taking in the sight of him standing there before me in my sexiest out fit, the very same one I was just thinking of putting on, I almost laughed, but contained the giggle. "Do you like the way you look James?" I asked bending to untie the laces on my boots. When I did not get an answer I looked up at him, my hands still working the laces. I could not get the sight of him out of my head. Setting my boots to the side I leaned back in the chair. "Well?" I asked. He was flushed from head to toe and fidgeted a bit under my intense gaze. I gripped the arms of the chair to keep from touching myself as my desire increased. After an eternity of silence he finally answered softly. "I don't know." He stammered "I was just about to..." and his voice trailed off. Leaning forward in the chair to unbutton my coat. "You were just about to what James." I licked my lips. Taking a deep breath he blurted "Just about to look in the mirror, but when I turned around I saw you standing there." "Then close the door and look in the mirror James." I managed to keep my voice calm; I did not want him to know the great excitement he was stirring in me. Slowly he skirted the chair and closed the door. "Look in the mirror and tell me what you see James." I commanded. He had his eyes closed as if he did not want to see himself. "James look to me." I said softly my voice almost a whisper. He looked deep into my eyes, and I could see his body relax as he saw no ridicule there. "Now James look in the mirror and tell me what you see." Taking a deep breath he looked into the mirror. He stood there looking back at himself for a long time. "Pose yourself James." I commanded. "Let your body go, you may pretend I am not here if you wish." I whispered again. "Your presence touches every fiber of my being.” he sighed, “I could never pretend you were not here." He smiled that sweet smile that drives me crazy before looking back into the mirror. He turned slightly from side to side, and then turned around looking back over his shoulder in attempt at admiring his back side. "What do you see James?" I asked again sliding my jacket off. "I see," he breathed heavily "I see how sexy you feel when I look at you the way you are looking at me." Hmmmm. I purred and rising walked to the mirror to stand behind him. I took in our reflection in the mirror. James was just a little taller than I. The black teddy fit him perfectly; it stretched tightly across his well muscled chest. His erect nipples stood out beneath the satiny material. Hungrily my eyes devoured his body, and settled on his cock. Tho he trembled and seemed a bit shy to be dressed this way I could plainly see how aroused he was. His cock was swollen and jutting straight out from his hips. A tiny drop of pre cum stood on the tip. It was hard to contain myself, to keep from dropping to my knees taking his huge shaft into my mouth. Moaning softly, I diverted my attention, letting my gaze travel back up his body to his face. Looking into his blue eyes I could see the fire that sparkled there at the hot openly lustful looks I gave him. "Do you know what I see James?" My voice was rougher and more commanding. I raised my hand and trailed it down the side of his cheek and neck, continuing on down to his chest. Lightly fingering his nipples throughout the fabric I repeated my question. Moaning slightly James leaned back into me as my fingers brushed his hard nipples. "Do you know what I see James?" I pinched his nipples roughly, twisting them slightly. A slight whimper answered my question. "Answer me." I pinched and twisted a bit harder. "No." he breathed hard. I lightened my grip on his nipples acutely aware of my own straining beneath my hunting gear. "I see my little slut who will do anything to please his Mistress." A smile of desire covered his face and he whispered, "Yess Mistress Brenda." "Look into the mirror and tell me what you see James" I commanded him. He looked into the mirror as I tightened my grip on his nipples again. "I see," he sucked in a harsh breath of air, "I see your little slut, your fucking slut." "Good boy" I whispered releasing his nipples and stepped back. "Now you may be very comfortable in that sexy outfit my little slut, but I am very hot and bothered under all this hunting gear. I want you to undress me and then..." I ended with an evil sneer. "Now slut!" Quickly he turned to face me and began unbuttoning my many layers of shirts, slowly unbuckling my pants, and sliding each pair off. When he finally got down to my tee shirt, and stretch pants I caught his gently caressing my thigh as he pulled the final layer off my hot naked skin. "No." Smacking his hand away. I jerked his head up by the chin. "Did I give you permission to touch me?" "No Mistress Brenda, you did not." There was a hint of rebellion in his voice and a mischievous twinkle in his eye. Leaning closer and whispering harshly, "You had better not touch my flesh with your skin again, or I shall have to punish you." my voice holding a threatening note. "Yes, Mistress Brenda." Letting go of his chin he finished stripping me. I walked to the closet and picked out a black mini skirt, my favorite black bra and a white blouse, "My slut, I am going to take a shower. When I return I want you dressed, we are going out to the bar. You had better keep what you have on under your cloths. Understand." I looked to James. His eyes were wide in shock. "But Mistress Brenda..." he stammered. Setting my cloths on the bed I walked behind him. Whispering into his ear. "Yours not to reason why, yours but to do and die. Do you understand my little slut? You will put on your tightest jeans and a nice fitting shirt over your slutty little outfit. And I will spray some perfume on you before we leave. I want you to fit the part, understand my little fucking slut?" I turned the water on in the shower, and stepped under its hot flow. I ran my hand over my breasts, down my stomach and between my legs. Lightly probing I found my cunt hot and dripping wet. I lightly rubbed my clit, dipping a finger into my cunt. Sitting on the edge of the tub I rubbed my clit harder. Within seconds reached a hard orgasm. "Yesss..." I hissed through my teeth as the wave washed over me. I leaned back and let it take me. My muscles spasaming. I quickly finished dressing, and headed for the bedroom. James was kneeling obediently a few feet inside the doorway. Hands laced behind his back, head up face straight, eyes down, focusing on the carpet a few inches in front of him. He straightened a bit when he sensed my presence. He was dressed in his faded blue jeans, black Nine Inch Nails tee shirt, you could just make out the lines of the teddy beneath the shirt, and the garters stood in proud relief through his jeans. I looked to his crock and was met with a hard bulge between his legs. I smiled knowing he was enjoying this as much as I was. "Very good my little slut. But as I think of it there are a few things you need on as well." James whimpered, his eyes wide, looking me in the eye, he knew what was coming. I walked to the dresser and opened the top drawer. The toy box we jokingly called it. I scanned its contents quickly location the nipple clamps, vibrating butt plug, and cock ring. Taking the items in hand I walked back to James. “Raise your shirt for me.” He quickly obeyed. Setting the toys to the side and taking the nipple clamps and knelt down in front of him. Gently running my hands over his already hard nipples. I lean in and suck first the right. Gently biting it. Making the fabric of the teddy wet with my mouth. James breathed in hard, arching his chest to my mouth. Sliding the top of the teddy down I gave it one final suck and slid the nipple clamp in place. I let it settle softly into place and James moans as it closes tightly. I run my thumb around the nipple and lightly brush it. He rolls his hips to me his arousal very visible in his jeans. Letting the teddy return to place I slid down the other side. James moaned as I gently pinch the other nipple, beginning my torture anew. Moaning and grinding his hips fiercely to me, I slid the second clip into place. Tightening them lightly, bouncing them in my fingers. I looked at James his face a mixture of pleasure and agony. "That’s right my little slut, you love it don't you?" without giving him a chance to reply I ordered him to pull his shirt down and then stand and pull his pants down. He moved quickly to do so. He stood still with his hands laced behind his neck. I slowly walked around him, admiring the curve of the black satin against his skin, the lay of the garters to stockinged legs. As I passed the dresser I picked up the riding crop from the dwar. Walking back to stand before him, running the crop down his face to his lips. "Kiss it." I ordered. "Take it into your mouth and suck it." James’s eyes filled with tears as I forced it into his mouth, sliding it roughly in and out, fucking his mouth with it. He moaned as he sucked, his hips gyrated towards me. His hard cock standing out straight. "Good slut." I said taking it from his mouth again. Taking up the cock ring I buckled it on to his cock. Then I sucked roughly on the head making it throb. Moaning in pleasure James thrust his hips to my awaiting mouth. I ignored the first couple thrusts but when he began to pant and thrust harder, I pulled back out of his reach. "No. I determine what goes on here, not you my little slut." I stand up and walk behind him. Running my crop up his thigh to his ass, I saw him shiver. I pulled the crop back letting it fall forward cutting the air. I knew James heard it whip through the air because he tensed and gave a soft moan in anticipation. I stopped it short of making contact with the flesh of his ass. It popped softly making him jump and relax. As soon as his ass cheeks relaxed, I lashed out with a quick short stroke. It caught him totally off guard and he leapt forward a bit, yelping at the sting. Smiling I brought the crop across his ass faster and harder. His breath came quick; it did not take him long to start moaning and then softly whimpering at the sting on his skin. I lowered the crop to inspect my hand work. Leaning in close I ran my fingers across the welts that were forming. James flinched away from my touch and then moaning leaned into it. I took the butt plug and ordering him to bend over I began licking his ass hole, lubing it with my saliva. Taking the butt plug I slowly inserted the tip along with my tongue. Shoving it in and pulling them back out ever so slowly. Each stroke getting deeper, until it popped into place. I stood back and James thrust his hips back to me. "Please Mistress Brenda." He whimpered. "Please what my slut?" "Please fuck my ass Mistress Brenda and let your slut cum for you." I laughed and ordered him to pull his pants up and button them I wanted to go out. I slid into the driver’s seat of my truck. And waited for James to get in. He sat gingerly and I knew he was lost in a wave of feelings from extreme pain from the crop, to delicious pleasure from his other adornments. I smiled wickedly as we drove down the drive way. The bumpy dirt road caused him to whimper and moan at every rut and rock. Sighing in relief as we turned onto the paved road, he leaned back a little into the seat. The drive passed quickly and there was a look of fear on James' face as we parked outside our local bar. I smiled wickedly at him as we walked in. I saw a few people from town I knew and walked over to where they were sitting at the bar. Within seconds James appeared at my right side and set a Coors light down in front of me. I waved my hand slightly and he went off to greet a few people he knew. The night passed quickly. James kept a weary eye on me the whole night. Making sure that I had plenty of cigarettes and a cold drink. I watched him as he began a game of pool with a buddy. I could clearly see the line of the garters he wore every time he leaned over to take a shot. I was getting hotter and hotter watching him. I waited until he was about to sink the eight ball and I made my way over to the ladies room. As I passed the pool table I pinched his ass, whispering "you’re my sexy little slut." I laughed as he scratched as the cue bounced off the table, and missing the cue ball entirely. Ducking into the rest room, I took one last look at him, the bulge between his legs quite evident. He was as horny as I was, and gods above did I need relief! Exiting the rest room I caught his eye and with a slight movement I motioned that it was time to leave. He was beside me quickly, helping me into my coat, he silently paused as I walked away and then kept a three step pace behind me, I glanced back and his eyes were down cast. "Good slut." I whispered with a smile. As we pulled out of the parking lot I reached over and rubbed his thigh, feeling the lace from the top of the stocking underneath. Slowly I ran my hand up the line of the garter and between his legs roughly rubbing his still hard cock. Trying to conceal a frustrated moan he rolled his hips to my eager hand. Unbuckling his pants I freed his member, gripping it in my hand, I began stroking it. He leaned back in the seat moaning. First slowly and deep then wringing his hard cock in my hand making short quick strokes. I could hear his heavy breathing turn to a pant and knew he was close to cumming in my hand. "Don't cum slut.” I warned him, slowing my hand down to an agonizingly slow pace. "Don't cum on your Mistresses hand, do you understand?"A whimper was the only response. Gripping his cock hard at its base I growled. "You don't want to disgrace yourself in front of your Mistress do you?" my voice held a menacing threat. "No Mistress Brenda." He moaned through gritted teeth. The ride home seemed endless. I could not wait to get home and have James at my whim. As we entered the house I closed the door and locked it. I set my keys down and ordered him to strip. He slowly removed his jacket and hung it on the hook beside the door. Then turning to face me he started to pull his shirt off. "Give me a show slut." I ordered. He hesitated for a moment and then began to sway and gyrate his hips. I knew the nipple clamps were tugging on his nipples and each turn of his hips pressed the plug deeply into his ass. After a few seconds he seemed to get lost in the pleasures he was giving himself. Slowly he slid the shirt over his head and let it drop to the floor. Reaching down he began to un button his pants and unzipping them turned his back to me. Bending over he slid the pants down his legs and wiggled his hips showing off the pug still deep in his ass. He stepped out of his pants and turned once more to me, still swaying to a beat only he could hear. His eyes caressed my body as mine ravaged his. Moaning I ran my hand up my own thigh and gently caressed my wet cunt through my thin panties. His little show was driving me to the edge. But I wanted to savor my sweet slut. I stood and walked to him. His face a mixture of uncertainty and desire. Pulling him into my arms I kissed him deeply. My tongue possessing his mouth. Whispering hotly in his ear. "Come James, I want to fuck my little slut." Taking his hand I lead him to the bed room. Closing the door my mouth is once again on his. Dipping deeply into his mouth, playing with his tongue. He moans as I bite his lips roughly. Sliding my hands down his back I pull his hips closer to mine. His hard cock rides against my mound as I grind to him. I let my hand slide a little farther down and gently tug at the plug in his ass. Moaning James rocks his hips hard to my own. My hips grind against his erection. Moaning my kisses turn to nibbles and then to bites as i work my way down his neck to his shoulders and finally capturing his nipples in my teeth. Biting and sucking on them through the thin material. James gasps as I bite his nipples, his head leaning back arching his chest to my mouth. Sucking harder I slide my other hand down his belly to grasp his hard cock. It stains against the cock ring as I stroke it roughly. Dress Up I don't know how to explain it. I am not gay although I may be passive bi. I have had sex with men, but not a lot and I have always been the one receiving, you know once a friend showed me a pack of pictures of his wife from fully dressed in conservative suit to complete nude with some action photos, her sucking his dick and fucking her self with a rubber dildo. I thumbed thru them while he suck my cock. Later I fucked his wife while he took pictures, but that another story. What I want to tell you about now is when I was younger. I loved the feel of women's under garments. I would sneak into the bathroom or laundry rooms of my friends and dig through the dirty closes until I found their mother or sisters panties and bras. Then I would smell and lick the crouch and cups and even the parts of the bras that ran under the arms and rub them over my face while I jerked off. I love the smell of women. Then one day when my parents were gone out of town over night and left me at home by my self I got a idea. I went to one of my friends house down the street and while there asked to use the rest room, I knew that in there was hamper that was where his mother put her things when showered. Once by my self I opened the hamper and dug out her bra and panties, I held the panties to my face and breathed in the aroma from her long days work, my dick jumped to attention. I stuffed them down into my pockets and went back to my friends room and continued our discussion. After a respectful amount of time I excused myself and went back home. Once in my bedroom I quickly stripped off and lay across my bed, sniffing the crouch of my new prize, while I stroked my cock. Then the thought came over me I don't know from where, but I thought, Wanda, my friend's mom was as big woman, about my size with nice big tits, the bra was 38, c-dup, I was five foot eight inches tall with a slim build so I thought I might be able to get he under garments on, I just wanted t see how it would feel to whack off with her them on so I pulled the bra straps up my arms but found it hard to fasten the clasps in the back so I took them off of my arms and fastened them in front then I worked the cups back to the front and pulled the straps up onto my shoulder. Immediately my dick grew harder. I stepped into the panties then pulled them up my legs and over my muscular ass, my rock hard cock held the material away from my pubic area. I lowered the front of the elastic and started stroking my cock again as I lay across my bed. I soon realized that I was not getting to full effect from the panties so I took a knife and cut a slit in the front of the silky white under pants and poked my dick through then I lay back down and continued whacking off while with my eyes closed I played my nipples through the bra cups and rubbed the sticky crouch of the panties between my balls and ass hole. In just a few minutes I shot the largest loads I had ever had on the towel laying on my bed. From then own I was hooked. Ever change I got I took undergarments from my friends houses, some were too small for me to get on but I still jacked off using them. After a while just the under garments were not enough I began taking dresses, and I even got a wig from one of my Aunts, then I would dress completely like a woman and whack off. I know it sounds like I am gay but the weird thing is I never think about men when I dressed up I always imagined of what it would be like, being a woman fucking another woman. I began to collect a large amount of women's clothing, and was afraid my mom might find them and I would be in deep trouble, so I asked if I could use the shed out back, that used to be a pump house years ago when my grandfather had a well where the got water. My parents said that would be ok, as long as I kelp it clean and took care was not drinking or smoking out there, little did they know. I would spend hours out there dressed up like a housewife, a hooker or even a cheerleader, whacking off to visions of hot slutty women. I had my friends over to what we called our clubhouse none of them knew what I was doing when they were not around. To prevent my secret from being discovered I made as trap door in the ceiling where I stored my alter ego's clothing. A pleasant surprise was that t the sun on the tin roof kelp the garments heated up and the smell of the women who had last had them on stayed with them for a long time, which help enhanced my experience. I would pull all the clothing around me while dressed up and smell, lick and suck on deferent women's panties and bras while jerking off, I even had pictures of the women whose clothing I had taken, that made it even better. Then one day I must have been in a hurry to get started and forgot to lock the door, because while I was in the middle of a extremity hot session, the door opened wide. There I was, with my wig on, the front of my dress pulled up my dick sticking out the cut slit in my panties my bra, filled with panties and pantyhose straining at the material of the red flowery dress, and my dick in my hand. I froze, my nineteen-year-old cousin, Joan stood looking at me with a huge smile on her face. "Hey Birdie, come and see what I have found!" She called to her sister as she stepped inside my Clubhouse. Then my other cousin looked in the door and broke out into a loud laugh. "Oh shut up and get in here!" Joan said closing the door behind her. "What are you doing, Johnny?" she asked pulling at the hem of my dress as I tried to hide my deflating cock. "Oh come on sis you know what he's doing, the little sissy is whack'n off." Birdie said walking over to my side and yanking the panties I had to my nose from my hand and pulling wig from my head. "I bet he would like to suck a big dick." She laughed. "Is that it?" the older sister asked sitting down beside me and taking my now limp dick in her hand. "Do you want to suck a dick?" "No!" I answered loudly, "I don't like dicks." "Lets see then." Birdie said pulling down her tight jeans, "If he don't want to suck a dick maybe he wants to lick my pussy." She said as she stepped forward and pulled my face between her spread legs. The smell of her hot cunt was intoxicating as she smeared herself up and down my face. I never dreamed it would be so arousing. My dick began to harden. I could not believe how much better panties smelled with a pussy in them compared to the used ones that I had here to fore been able to snatch from my friends' mom's laundry. "Look Birdie, you making him get hard again." Joan said as she took my dick in her hand and started to stroke it up and down. Her sister looked down and laughed, she then pushed me back until I was lying on the couch. "You can suck him I want his tongue in my pussy." She said dropping her wet under ware down and kicking them into the corner. She straddled my head and lowered her hairy cunt down on my face, spreading her pussy lips at the same time. Then I felt something wet and warm on my dick and I could feel hot air blowing the hair around the base as Joan's mouth moved up and down my cock. I licked my tongue up and inside my cousin's hot hole and then took her clit into my mouth and sucked down on it. "Oooh yeah! That it sissy boy, suck my clit like a little dick!" She ordered as she began to buck faster on my face, and her older sister took all of my cock deep into her mouth. While I was licking at Birdie's pussy Joan was going to town on my dick her wet lips were wrapped around my hard shaft with her hand squeezing the base, and her head moving up and down sliding it in and out of her throat. Birdie got two hands full of my hair and began to fuck my face with her cunt, shouting obscenities as she rocked back and forth. "That it eat me suck my hot cunt!" She yelled as she moved he wet slimy cunt back and forth on my face. I could feel my load building up inside of me then as my cousin pulled my mouth up tight into her opening and started gushing, her head flew back in orgasmic bless, I shot my first load deep into Joan's hot mouth, she swallowed it down then pulled back and stroked my cock as I empted my seed. She let me finish shooting high in the air and landing back down on my belly. When she was through birdie got off of my face and bent dipping two fingers into my cum splattered on my belly and shoving the gooey mess into my mouth. "There you go Cus, eat that cum like the sissy you are." She laughed then Joan joined her scrapping the cum from my body and feeding it to me. When they were through they both kissed me on the forehead and said we'll have to do this some other time and left me in the shed along. Over the years we did repeat the events in the shed, even to this day when one of them calls me I stop doing what I am doing and go to them, but that is another story. Dress Up He had been begging me since we met to take him out, dressed as a woman. At 6'3", it was going to be a challenge to make him look like any kind of a lady. She told him to lie on the bed, where she tied his arms and his legs to the bedposts. Her favorite position for him, face-up. He never knew what to expect when she did this to him. He couldn't help but get an erection, his cock always got hard when he was around her, it was involuntary, uncontrollable. He did as told, spread his arms and legs and felt pure bliss and joy as the cuffs went on. He was going into her space, his space, subspace. Heaven on earth, is how he described it. She didn't crawl on top of him, placing her crotch or her ass over his face. She didn't move over his cock, she slapped it, telling him to relax, this wasn't about sex. She pulled a chair over to the edge of the bed and began painting his fingernails. "Hold still," she ordered him. "I am doing this once and once only. If you mess the polish, tough shit. This is all you get." "Yes, Mistress," he closed his eyes and enjoyed the moments, each of them. Every minute spent in her presence meant another moment of happiness for him. The light touches of the nail polish brush on this fingernails was strange. He could just barely feel it, he was accustomed to something stronger, harsher from her. No matter, he waited for something greater. A stronger touch, another swat on his cock or a slap across his face. These were his favorites. She was expert at delivering them and she knew how much he enjoyed her touch - in any form. "Don't move your fingers, they are perfect." He stayed very still as she blew on his hands, his fingers, one by one, moving on both sides of the bed, climbing over his body, as if he were not there, naked, erect and excited. She moved the chair to the end of the bed and began painting his toenails, occasionally using the crop against the bottom of his feet. "Don't fuck up the polish," she screamed as his feet flinched each time they were hit. She blew on his toenails, alternating breath with slaps on the bridge of his feet. "Those will take awhile to dry. I'll be back," she yelled over her shoulder as she shut the bedroom door behind her. He laid there, naked, erect, and wondering what was next. He couldn't help but wonder why she had picked now to paint his nails. He waited and watched the sky grow dark. He didn't fall asleep, but this was a meditative place for him. It was truly the only time in his life when he could completely clear his mind, turn it all off and just live in the moment. He was responsible for no one, only responsible for providing Mistress' pleasure when she desired. That was the only reprieve he had in his life, the only break he got. She understood that and she made the most of it. He didn't know how long it had been when she reentered the room but she looked different than she had previously. She was dressed to go out - stockings, makeup and her hair was up and back, away from her face. This was how he liked her best, the lines of her jaw and her high cheekbones clearly visible. He still couldn't quite believe what they had managed to work out between them, how well this worked for them both. He knew what he needed, he knew, in his heart, that he was a sub...he was a man who needed to serve a woman, a woman greater and stronger than himself but finding her had been a challenge. He had all but given up hope when they met. He had made a joke about spanking in one of their earlier conversations, and she had picked right up on it. At that point she had only received spanking, she had been dominated by a ruthless, selfish, arrogant man and she had shied away, not only from the D/s world but from men as a whole. He had jumped at the chance to bring it up, to discuss it, to see if he could interest her in switching sides, so to speak. She had taken to it naturally, remarkable, really. Nothing about their relationship was simple or convenient but they both felt that it was what truly worked for them - anything else at this point would be a cheap alternative, filler, second best. They'd both had enough other relationships to know the bond they shared was real, vital, substantive. "Are you going out, Mistress?," he asked, wondering if he might have the chance to lick her pussy or suck her nipples before she left him there, wondering when she would come back, if she would come back. She liked that, to leave him. She liked the mystery and the power that it brought. He never knew when she returned if she would want to fuck him, be fucked or have him lick her clean of another man's cum. That was an amazing experience and one that he relished. They had come so far together that she could ask nothing of him that would be too much, over the top. She was perfect for him, in every way. To the outside world, he was a macho, alpha male and she was the only person who knew what he truly needed and wanted. A woman he could worship, treat like a queen and who would not judge him. Their bond was exquisite and they both cherished it. "Yes, I am going out and you are coming with me," she replied. He looked surprised as she had just painted his nails. Where could they be going, he wondered. She began to untie the restraints, instructing him to get up, get moving, it was late. He did as he was told. She lead him, by his cock, into the bathroom where she sat him on top of the toilet. Then she started to wrap his hair around a very hot curling iron. He flinched unsure that she was watching what she was doing. He hated burns and she had never taken that route with him. "Oh, don't be such a pussy! Women all over the world do this every day," she scolded him. She continued to play with his hair, curling, teasing, spraying and then the makeup bag came out. "Close your eyes," she said as she applied the liner, the shadow and finally the mascara. "So unfair, a man having eyelashes like that. Such a waste!," she slapped his face as she spoke these words. "Good, bring a little color to your cheeks." She followed up with some blush and then used the brush on the top of his chest, between his breasts. She also took the opportunity to squeeze and twist his nipples, causing him to cry out. She smiled at him, kneeling in front of him, running her hands along his thighs. "Let me take a look at you," she held his face in her hands. "One kiss before the lipstick goes on," and he could feel his cock standing to attention. She noticed as well and she lifted her skirt and slid her slick pussy down onto it. Oh, god, she felt so good, so warm, so wet. She didn't move for a long time, just stared into his eyes, smiling. "You make a beautiful woman, albeit, a woman with a hell of a cock but a woman nonetheless." She kissed him again and then her cunt muscles went to work on his cock. How she did that, he would never know. She was barely moving her body and yet, yet, her pussy was swallowing his cock whole. Causing him to shudder and spasm. She began to ride him, in earnest, and he could see that she was coming closer and closer to reaching a climax. He began to push up against her, trying to create some friction so that he could come with her but as soon as he began to move, she stopped, slapped him hard, first across the face, then around his chest. "Do not move a fucking muscle, understand me?," she whispered into his ear. He nodded and sat quietly as she, again, rode his cock, harder and deeper, using her muscles to drive him crazy with lust. When she came, it was unmistakable. The cries which grew louder and closer together, the gush of juices that came out of her, the flush of her cheeks and her chest. He had never known a woman to come with such abandon, with such flourish. He loved it, he lived for it. When she recovered, she told him to purse his lips and she applied a bright red lipstick. "Go look at yourself as a woman, in the mirror. You look pretty damn good, if you ask me. I mean, you could never pass as a woman, but that will be half the fun," she smiled at him, knowing that the thought of being caught, dressed as a woman, in his own community was a fear of his. She went into the bedroom and came back with a small g-string panty, clearly made for a woman about half his size. "Put these on," she instructed, knowing that his cock was still hard and wet from her orgasm, when she had refused to allow him to reach any sexual satisfaction. "Now, this," she said, holding out a dress that was black and long. "Oh, wait, you'll need a bra and some fake boobies," she told him, tweaking his nipples again. "Maybe a little rouge for your nips?" "Yes, Miss, please," he couldn't believe that he was finally getting his wish. Of course, he expected her to do this in a town where he didn't know anyone. He would never be able to hide behind the dress and the makeup. He could only hope that he wouldn't run into anyone he knew. When dressed in a bra and panties, his erection still evident, she turned him around to look at himself in the mirror. "Pretty ugly sexy, don't you think?" she teased him. "Yes, Mistress, as long as you are pleased that is all that matters to me," he answered, looking down. He couldn't believe how hot this was, how turned on he was. "Raise your arms into the air," his mistress instructed and she slid the dress down over his broad shoulders and newfound breasts. The dress felt silky and soft against his skin but he waited for her instructions before looking at his reflection again. "Put these on and your shoes are by the bed," she said, tossing him a pair of pantyhose in an extra-large size. "Lets hope these can help hide your erection. If not, I am going to have to beat it out of you. Now go put on your shoes, then come back in for another full-length glance at yourself." The red pumps with 3" heels fit perfectly but maneuvering his large frame on them would take some getting used to but he made it into the bathroom without falling and when he looked at himself, it took a moment to believe that it was really him. Tall, beautiful eyes, his silver hair looking like he had just stepped out of a beauty salon. The dress fit him perfectly, just the right length, covering his knees and the red shoes completed the outfit. He caught her eye in the mirror and they both began to giggle. Laughter was the thing that they always could rely on, finding the same things humorous, making jokes to alleviate some very awkward situations - laughter had been a glue for them in the beginning. "If I didn't know you, I'd want to fuck you," she whispered into his ear. "Hell, I do know you and I can't wait to fuck you," she added, grinning from ear to ear. Dress Up Ch. 02 She told him to follow her as they walked to the car. She held the passenger door open for him, telling him to get into the car. She made it clear that she was in charge, that she would be driving. He always drove, it was part of their routine. He was the alpha male, the guy in charge, to the outside world but not tonight. Tonight, she was the alpha female. She took the road towards the highway and he breathed a sigh of relief. "We are not coming back to the house later, I have a treat for you tonight," she told him. "Don't worry about anyone you know recognizing you. I want you to relax, enjoy the experience, be the woman you've always wanted to be. Leave it all up to me, trust me, put your faith in what I can do for you. Deal?" He nodded, exuberant in the possibilities and in what she could bring out in him. "How do you feel? Comfortable? How are your clothes? Is there anything else that might help you feel like more of a woman?" He shook his head. He was trying to revel in the moments, these moments of authenticity. "How is the plug? The one I slipped into your anxious and ready asshole earlier? Is it hurting you or does the stretching feel nice?" "It is all fantastic, thank you, Mistress," he answered. "I can't think of anything that could make me happier. I am so grateful to you." "Don't get all relaxed and grateful yet. This is only the beginning of our evening. I have things planned that I won't tell you about yet because I worry that you might jump from the car. It's going to be a bumpy ride - a magical, exciting, mind-bending ride," she smiled as she spoke the last sentence and reached over to rub his cock. It was exciting to feel his cock under the silk dress, the hose, the panties and his cock exhibited the same excitement. Her hand came down on his cock as swiftly as her reach over to rub it. "Did I tell you that you could get hard?" she demanded. "No, Mistress, you did not. I am sorry," he said, looking down at his very erect member. "Does a woman have a bulge in her panties?" she went on. "No, Mistress," he answered. "Well, then, you best get rid of that bulge in your dress before we arrive at the restaurant" and with this, another few slaps to his cock. She quickly pulled onto the side of the road, put the car in park, and moved on top of him, straddling his cock, rubbing her pussy against him. She kissed him, on the mouth, lipstick to lipstick, smearing his. She pulled her face back and looked at him, his beautiful eyes, mascara-laden eyelashes, and blush. "My, my, you do make a pretty girl," she announced. She kissed him hard again, pushing her tongue past his lips, searching, taking control, rubbing his cock into her crotch. One hand wrapped around his jaw while the other struck his cheek, causing his face to turn red from the strikes. "I thought I told you not to get hard," with each syllable out of her mouth, there was another blow to his face. She lifted her body off of his and looked down at the bulge in his little black dress. "What the fuck do you call that," she asked, squeezing his cock as hard as she could. His mouth opened but no sound came out, he was paralyzed by the pain. "Fucking answer me when I speak to you," she demanded. "NOW!" "I am sorry, Mistress, I cannot help it," he whimpered. "You are such a fucking pussy, you piece of shit. I always knew you were a pussy and this just proves it. Pull it together and get rid of that erection," she instructed. "You make me sick," she said, as she let go off his cock. She went back to her side of the car and opened her legs. One leg behind his seat and the other on his lap. Her back was against the driver's door and he could see that she was not wearing any panties. Her hand reached under her dress and she began to play with her pussy. He could smell her scent and that always drove him crazy. He couldn't believe what was happening. Headlights were shining into the car but no one stopped, no one seem to see what was going on in this car, parked on the side of the road. "Pull out your cock and play with it, now, here. We need to take care of this issue, this problem, this bulge in your dress," she whispered. He unhooked his seatbelt and lifted the dress up around his waist. He lowered the stockings and the panties and did as she told him to do. He began to stroke his cock, while watching her. He loved watching her masturbate. Nothing turned him on more than her hands in her cunt. "Lick my fingers clean," she said as she held out her drenched fingers for him to suck on. "That's a good little pussy man," she mocked. He licked her hand, between her fingers, sucking on the tips, so as not to miss every drop of his Mistress' juices. She was glorious, perfect in her ability to tell him what he needed, what he wanted. He adored her, as he had no one else. He was rubbing his cock, hoping to make cum so that he could walk into the restaurant without this bulge in his dress. He wanted nothing more than to walk and talk and act like a woman. This had been his dream, his fantasy, for as long as he could remember. He never dreamt that his Mistress would actually let him live out his desires, his wants. This was an amazing night already. "That's it, pussyman, rub your pitiful little cock, make yourself cum but don't get any of it on your black dress or you will have to walk around with a cum stain on it and don't expect me to clean it up or to suck you off. It's time you learned how to masturbate neatly, like a woman does," she spoke softly, almost as if she was pitying him and this only turned him on more. His body began to convulse, watching her fingers as she expertly pleased herself, feeling the stockings tight around his thighs, imagining what he must look like to his Mistress, it was almost too much to bear. He closed his eyes and he came. He came harder than ever and his cum spurt up and towards his chest, leaving a big messy glob between his "breasts." His hands were wet and as he tried to clean up the mess off of his dress, he only made it worse, smearing it, making the stain larger. She began to giggle and told him that he would have to ride the rest of the way to the restaurant like that, with his panties around his thighs and his dress hiked up around his waist. "Better hope we get there safely, pussyman, because you wouldn't want an officer finding you like this, would you?" she teased. He was still seeing stars from his ejaculation. He'd come so quickly, so hard, that he didn't have time to collect his thoughts before she had gathered herself back together and started driving again. She began driving very fast, weaving in and out of traffic, and the honks and hand gestures were frequent on their drive to the out-of-the-way restaurant. She did make a point of slowing down whenever they were beside a truck or a delivery van. She gave everyone on the highway a chance to see his shriveled cock hanging out of his panties, and all they had to do was look down into the passenger side of her car to see the pitiful man's even-more-pitiful cock. They received lots of honks and hollers, and he could feel the shame rising up in his face, causing him to blush. Finally they arrived at the restaurant. It was a little Italian place, and it looked very homey, like a neighborhood joint. She got out of the car, quickly, and she leaned in to tell him to pull up his hose and his panties and to come in when he thought he could look like a lady. She asked for a booth and told the maitre d' that there would be one more joining her. "A big girl," was how she put it to the host. She sat down in the booth, ordered a drink and began to look over the menu. The host brought him towards her booth and she acted as though they had not driven over together. She greeted him/her enthusiastically and she ignored the looks of the host, the smirk. "Oh, honey, sit here, next to me," she stood up and insisted that he/she sit on the inside of the booth. "I will order for you," she told him as they began to look over the menus. The waitress came over and had a hard time not staring at him. It was so apparent that he was not a she. "My friend, here, will have a Shirley Temple," his Mistress told the waitress. The waitress almost laughed out loud but the look she received from his Mistress was scathing, so the waitress didn't let on that it was obvious he was a she. When the Shirley Temple arrived, she gave the waitress their orders for dinner. He did not speak, he did not even look up at the waitress. This was much more difficult than he had anticipated and he was grateful that his Mistress was handling everything so beautifully. "Just relax, babe, everything will be okay. Enjoy being a woman, you look fantastic and I would hope that you feel fantastic...I mean, aside from the huge cum stain on your dress, you look amazing," she whispered into his ear. He had completely forgotten about the cum stain and he began to blush, yet again. He had been so concerned with getting his cock back into the stockings and getting himself pulled together, as a woman, that he forgot that his dress was covered in cum. No wonder the waitress and the maitre d' were laughing at him. This was all more difficult than he imagined it would be, in his fantasy. "I think we should head into the ladies' room and get you cleaned up," she finished. "Oh, but before we do that, I want you to make your cock hard again because I need to be fucked. I got pretty excited back there in the car, when you were stroking your pathetic little cock. You know how much I love it when you suck on my fingers, wrapping your tongue around each one, the way that I have taught you to do. Your tongue is so talented, the way that it fucks my pussy and pleases my asshole. I know you long to do it now, to stick your tongue in all of my holes, don't you? You want to tongue-fuck me now, don't you, babe? You want to taste me, all of my juices, my cunt, my asshole...you want to service me, don't you?" she continued to say, softly, into his ear. She reached down to his lap where she knew that she would find him hard again and she was right. His cock was engorged, and he was ready to please her in whatever way he could, whatever way she would allow him to pleasure her. "I am going to head into the ladies' room and I want you to follow me in 60 seconds. When I stand up, begin counting and then walk over, very slowly, to the loo. I don't want you to try to cover your erection or your cum-stained dress, in any way, and if I find out that you have not done as I have instructed, be sure that there will be hell to pay," she warned. Before he had a chance to plead for another way, she had excused herself and began making her way to the bathroom. He felt as if every eye in the restaurant was on him. He looked like exactly what he was - a man dressed up as a woman, a 6'3", 220 lb man dressed up as a lady. He knew that he couldn't pass as such and this made it all the more difficult to slide out of the booth and to walk to the ladies' room. His erection was obvious and he was concerned that he would get called out by the management for indecent exposure. He felt even more immense shame at having to walk into the ladies' bathroom, as it was so obvious that he was not a woman but he did as he was told, not wanting to suffer the consequences of disobeying his Mistress. As he walked into the bathroom, he heard the door lock behind him and she put her hands on his head, forcing him to kneel on the floor. She pressed his face into her pussy and told him to lick her until she came. He began to lap up her juices, trying very hard to please her, to make her cum but each time she came close and he could feel her body begin to quiver, she would pull his head away. He knew how long they had been inside the loo and he was beginning to worry about the other patrons. More than once he heard a knock on the door and was surprised to her his Mistress yell out that she would be right out. "I'm coming," she would say, and then she would begin to laugh. This happened at least three times and it was hard for him to focus on his job at hand. She walked away from his mouth, his lips, his tongue and she walked towards the sink in the bathroom. She placed her hands on the sides of the sink and she flipped her dress up around her waist. Her spread her legs wide apart and she wiggled her perfect ass towards him. "Crawl over here, without ripping your stockings, pussyman, and suck my asshole," she said as she pulled the cheeks of her ass apart. "Make me cum and do it fast," she finished up before staring at him via the reflection in the mirror. He quickly crawled on the hard, dirty bathroom floor over to her ass and he stuck his tongue deep inside her asshole. He knew how much she loved his tongue in her back-hole and he was eager to make her cum but even more than that, he loved the feel of his nose in her crack, the taste of her ass, the smell of it all. It was, perhaps, when and where he was happiest, serving his Mistress. His tongue was growing sore but he would never dream of taking a break, he had learned the hard way that when she told him to do something, he best do it. Her consequences were swift and severe. He never knew what they would be, as she was by far, the most creative mistress he had ever served but she never failed to make him recall, for days afterwards, where he had failed her. He could never forget the board torture that she performed on his cock the time he had forgotten to return her phone call. He wasn't sure that his cock or his psyche would ever recover but he always called her at their appointed time after that. He could still feel the two unfinished pieces of plywood being slipped onto his cock and the screws that she used to slowly and methodically bring the two boards closer and closer and closer together. The pain was so sweet and so harsh that he couldn't help but get an erection, which only made it that much more painful. No, to this day, years later, he calls her when he is told to call her. He does whatever she instructs. He understands how difficult it is to be an excellent mistress, to put in the time and the energy, necessary, to properly train him. It's not an easy thing to do and she has made that perfectly clear to him each time he has fallen down on the job of being her slave. She tells him, usually with a crop or a switch in hand, how hard she has to work at being the perfect mistress and with each statement, she delivers a blow to his bare ass that brings him to the verge of passing out - with pain and with pleasure. He knows how difficult he was to train, what walls had to come down and how hard he fought against her every move - "two steps forward, three steps back" she used to say to him before he could admit to himself who he was and why, before he could completely and totally turn his sorry self over to her so that she could make him a better man and the man that she needed. His tongue was working wildly, circling, wetting, probing her beautiful asshole and her hips were reacting to his care. He asked her, politely, if he could use his hands as well and she screamed out an enthusiastic "Yes, god, just do what you have to do to make me cum!" His hands moved around her hips and while one hand pulled her ass closer to his face, making it easier for his tongue to stay fully in her asshole, sucking and slurping as hard as he could, his other hand went inside her sopping wet pussy. He found her g-spot, that spongey area that was unmistakable in her. He could tell by the movement of her ass that he had hit home. She reached back, wrapped her hands in his hair and forced his face farther up the crack of her ass. She was close, this much he knew, and when she stopped moving, when her hand went limp on the back of his head, he knew that response. He began to lick as fast and furiously as he could. Her juices were everywhere and he didn't need to be told to clean her up, he knew that was his job. He could rest assured that no matter who she fucked, how she came, whether by her fingers, her vibrator, his cock, his mouth or another man's cock, his job was always and always would be to clean her up. She was trying to steady herself against the sink as he spread her ass cheeks apart and lapped up all of her juices that he could. There wasn't a taste in the world he loved as much as her juices. The taste was intoxicating and mind-altering to him. He truly could turn into a different person, the real person that he was inside, when in her presence, when serving her. "Fuck me," she said, as he was just finishing his clean-up duties. "Fuck me now, from behind," she told him, as she readied herself with her hands, again, on the sink. He stood up, quickly, at the ready, always, and he lifted up his dress and realized how hot they both looked. Their reflections were in the mirror over the sink and their eyes met. What was said between them, at that point, without any words, was more powerful than anything they could put into words. Her love for him, her appreciation of him, her power to help him be who he truly was, all of that was evident in her eyes. His devotion to her, his true, inner desire to please her in whatever way she needed, his love and adoration for her was apparent to her when he looked at her the way he did at that moment. He held his dress up around his hips, he worked his panty-hose down and then the panties. He looked so beautiful to her and she couldn't wait to feel his hard cock in her cunt. He smiled at her as he slowly guided his cock into her waiting, hot pussy. She enveloped him. It was here where he felt most at home. She was his home, as much as he might want to deny it, he knew this is where he could live, forever. This was his sustenance, his love, his life-force. It was all here, between her legs, between her ears, in her soul. She knew him like no one else ever had and this was, truly, the biggest turn on imaginable. Nothing, nothing could compare to this piece of heaven in his hands, right now. After his cock was where it should be, in that place that made him happiest, where it belonged, his hands grabbing her hips, exactly as she had trained him to do, he began to slide himself in and out of her, slowly at first and then building up the speed, as he recognized her movements. He knew her body so well, he knew each quiver, each breath, what each sound meant. Her body always spoke to him - either through her gifts and kindnesses or through her punishments, which he knew, in his heart, were her gifts to him as well. His hand went to her mouth where she sucked on his thumb, wetting it, lubricating it. He knew just what to do and his thumb pushed its way into her asshole. This always made her a little crazy. Her hips were pushing back against his cock, grinding, humping, mad with desire. The farther his thumb made it up her ass, the deeper she wanted his cock in her cunt. Again, her body froze up and then her whole body began to shake. He knew her orgasms by heart, and she would next begin to ooze her juices down her legs, combined with his cum, if she allowed him to meet to let go but he didn't dare without her okay. He was so close, he wasn't sure he could hold back but he did. Her face fell against the mirror and she told him to pull out and start cleaning her up, again. And he hit his knees in grateful servitude. After he had licked and sucked all of her juices, again, he stood up, looked into the mirror and saw that his face, his lipstick, his hair, it was all a mess. But not his Mistress, she looked fresh, relaxed, put together. She smoothed out her dress, pushed her hair behind her ears, and put her hand on the doorknob. "Come out when you get yourself back together," she smiled at him, grabbing his still-hard cock and kissing him. "You really are a mess, babe, see what you can do before you come back to the table." Dress Up Ch. 02 She knew that people were staring at her as she walked back to their table where their food was waiting. The waitress and the host gave her a disgusted look and she smiled at them, knowing that they would kill to be in her shoes, to have what she had. It was only jealousy that made people act this way - it was about their shame and their inhibitions, not hers and not his, certainly. They had found their way around all of that, done it together and built something so beautiful, so beyond anything that either of them had even begun to dream of, when they initially met. It had been a long, hard road but they had arrived. He came back out of the ladies' room and sat across from her, in the booth. "Do I have your permission to sit on this side of the booth?" he asked, ready to move if she so desired. "No, that is fine," she answered while moving his placemat and his food towards him. It was hard not to feel the stares but she rose above it and began to talk to him about how much he had pleased her. She appreciated his lack of questioning her decisions, her power over him and her uncanny ability to know what he wanted oftentimes before he did. "How is the plug, slave? Is it filling up your tiny manpussy?," she asked in a normal tone, as if she were asking him about his day at the office. "Yes, Mistress, it feels wonderful. Thank you for asking. I hope I was able to please you in the bathroom, it seemed to take you a longer time than usual to come," he wanted to keep the conversation going, to hear her tell him that he had done a good job. She hated when he fished for compliments as she had found that she could easily spoil him. She walked a fine line between withholding and rewarding. "Are you looking for a compliment from your Mistress?" she asked as her foot found its way to his cock. She was still wearing her highest heels and this is the part of her shoe that pressed against his member. He almost spit out the food that was in his mouth, the pain was so great. "No, Mistress, I am sorry for bringing it up," he struggled to get out, each word being a chore as his cock was being pierced by her heel. "Do not ever, ever ask me to compliment you. I have told you many times that if I feel that you have done an exemplary job, I might reward you but if you are doing what is expected of you, what I have trained you to do, you don't deserve anything but to please me. What is wrong with you? Have I spoiled you tonight by bringing you out, dressed as the woman that you are, deep down inside, the hidden self, the one you fear more than anything else in the world? I think I have," and her heel dug deeply into his cock. "I am so, so sorry, Mistress, please, please forgive me and my selfishness. I am sorry," he begged, as the tears welled up in his eyes. "Oh, poor baby, are you going to start crying, right here at the table? Just like a real woman? Go ahead, let those tears fall, and then people can really stare at you, wondering what the fuck is wrong with that pussyman at that table. Yes, I am guessing that people will be talking about you for years to come. 'Remember that big man we saw that night, dressed as a woman, crying at the table?' they will say to each other. What a pussy," she was shaming him now and he knew, in his heart, that he deserved it, every bit of it. He knew better than to ask about his performance, he knew that she would either punish him (as she was so brutally doing now) or she would let him be - a reward was rare, very rare but when it came his way, it was oh-so-good and he lived, he served, he loved for those instances when her expectations of him were not only met but exceeded. That is when he felt the most whole, the most complete, the most like the man he was put on this earth to be. She lifted her heel off of his cock and he took in a deep breath. She leaned across the table and wiped away his tears with her napkin, making a fuss over him, embarrassing him further. When his breathing normalized, his Mistress told him that it was time to go, throwing $100 bill on the table. They might talk about the two of them for years to come but no one would never say that she was a bad tipper. "C'mon, Frances, it's time to get out of here," she said, reaching her hand out to him to help him get up from his seat in the booth. They both felt everyone staring as they walked to the door and she smiled at him, placing her hand on his lower back as she opened the door for him, walking behind him before turning around to smile at the host, giving him a wink. Once in the car, she told him, again, to relieve himself. She had another place in mind, to go dancing, and she didn't want to feel his pitiful little cock pressing up against her when they danced. "Do what you did before. Pull your dress up, so I can see your little cock, pull down your panties. Maybe this time you can have better aim and not get it all over your dress again. Remember the time I had your hips up in the air, with a dildo up your ass, and your cum shot right into your mouth? You loved that, didn't you? Tasting your own cum. You just love the taste of cum, let's face it. You are my little cumslut. You will eat your own or another man's, that has been freshly deposited into my cunt. You don't care whose it is, you just want to eat it all up, don't you?" As she spoke, this way, to him, his cock grew harder and harder and more and more full of his own cum. She knew just what to say to him to make him do what she wanted. He was putty in her fingers, it was, she thought, almost too easy. "OH, yesssssss, Mistress, I do love cum, anyone's cum that has been inside you....yesssssss, Mistress," he cried out as he furiously rubbed his cock. Just then there was a tap at the window and a flashlight beam shone directly on his cock, his dress around his waist, his stockings down around his thighs and his panties. There was no hiding, he had been caught masturbating in the car, in the parking lot. The police baton tapped against his window again, just as his cum spurt out of the tip of his cock and landed on his hand. He didn't know what to do now. He looked over at his Mistress with a confused look on his face. "Put your hand in your mouth, eat your cum, and then roll down your window," she instructed. He liked his hand, trying to get all of the gooey substance off before using the same hand to press the down button on the door handle. He tried to cover himself with his other hand but it was too late, the officer had seen it all. He was mortified and his mind raced with nightmarish possibilities. Could this be any worse? Why had he trusted her to take care of these details? All hell was getting ready to break loose and what could she do to stop it? "Looks like you all have come here for all the wrong reasons," the officer said when he bent down and peered into the window. His flashlight surveying the scene in the car. "I am going to need you to get out of the car," the officer said. He struggled to make his legs work, to open the door and to stand up. His Mistress put her hand on the door to get out but the officer told her to stay put. "I will deal with you later, right now I just want your friend here, whatever he or she is, to get out and put his hands on the car hood." His Mistress looked at him and said, "I am so very sorry. Really, really sorry." He thought he might throw up as he took the most manly steps he could towards the front of the car, trying to hide his face as the officer pushed him to the hood. "Put your hands behind your back," the officer instructed him. When he felt the cuffs go on, he knew there was going to be no easy way to get out of this, talking wouldn't work, he was fucked. He felt the cool metal of the cuffs, and he had to laugh at the absurdity of it all. He usually loved the feel of the cuffs going on but not this time, this time it was for real. "Spread your legs," the officer ordered him, as his feet kicked his legs apart, as much as possible, with the pantyhose band around his thighs. 
 "Put your head down on the hood," the officer demanded. He did as told, closing his eyes, hoping when he opened them, this would have all been a bad dream. He felt the officer lifting up the dress and pushing his stockings and panties down to his ankles. Then he heard the unmistakable sound of a switchblade being opened. He felt the ripping of the stockings and the panties, as the officer tore them from his ankles. "Well, that ought to make this a little easier," the officer said to him, as he pulled the ripped and ragged fabric from his feet. "Open your mouth," the officer directed him, as he shoved the dirty, cum-covered fabric into his parted lips. Just when he thought it couldn't get any worse, any more shameful, he felt his legs getting shoved apart by the officer's feet. He looked into the car and saw his Mistress' face. She looked horrified, and she mouthed "I am so sorry," to him as the officer's hand forced his head nose-down onto the cold metal of the car hood. "She can't help you now, you fucking sissy boy," he whispered into his ear. "You don't want to know what we do to sissy boys, here, in this part of town, do you?" Tears welled up, again, in his eyes and he shook his head, unable to speak with her panties in his mouth. "Well, want it or not, I am going to take you in and that ought to teach you a lesson to not come back here dressed up as a woman. One of the ugliest women I have ever seen, too. You know, what happens to women who turn me on is I fuck'em. But since you don't have a pussy, I am going to have to think of something else," and as these words rang loudly in his ears, he felt the officer's fingers searching for his asshole. He closed his eyes, hoping to make it all go away but there was no denying the digits exploring his ass and as the officer's first finger found its way to his manpussy, he wanted to die. "Well, well, what have we here? Something is already in your fucking asshole. Yes, my boy, you are about the most fucked up man I have ever seen," he said as he pulled the plug, roughly, from his ass. The sound that was made as it exited was loud and horrific. There was nothing he could do but endure this humiliation. The officer set the plug right in front of his face. "Look what I found in your asshole, boy." He didn't want to look at the plug but the officer picked up his head, his fingers wrapped in his hair and he picked up his head and all put put out his eye with the plug. The officer placed his feet inside his now-opened stance and he roughly shoved one finger into his asshole. "Plenty of room in there, boy, maybe you'd like another?" the officer mocked him. He tried to shake his head, no, no, begging, tears coming down his cheeks but the officer either didn't care of ignored his pleas for mercy. Another finger went in and then a third. Frances raised his head off the hood of the car and screamed out but no sound escaped past his gag. He noticed some people leaving the restaurant and them looked over, curiously. Frances begged them with his eyes, "please save me," he seemed to be saying but once the patrons realized who it was that was in handcuffs, they were happy to know that justice was taking place in their little town. "Nobody is going to come to your rescue," the officer said, softly whispering into his ear as his fingers roughly and painfully probed his asshole. This was the beginning of a very, very long night. Dress Up Day Ever since the first day that Sean began to work at the office, he had a deeply imbedded, wanton curiosity about the office Manager, Sally. Sally always dressed professionally, and always wore business attire. Her skirts were usually mid thigh and her blouses were perfectly matched with her jacket and skirt. She was in her late thirties to early forties, and in very good physical condition. Her body was well proportioned, and she maintained all of the right curves in all the right places. Her face showed a few signs of her age, but her cosmetics were applied in a way that one couldn’t notice the small crows feet at the corners of her eyes. Her dark brown hair hung at the tops of her shoulders and always had a very soft scent to it. She either was naturally dark skinned or her tanning sessions were timed to the second to maintain her sensual warm, healthy glow. Sean often wondered if she had been a model in her younger years, in fact, he sometimes caught himself fantasizing that she was. Sean was no slouch himself. His tender years of middle twenties helped him keep his physique toned with the chiseled look after his many hours he spends at the gym. Before he entered college, he often considered a career in bodybuilding or some sort of trainer at a spa. But after giving that idea some thought, he set his sights on a career in business management instead. His five feet, ten inch frame was one of the biggest reasons that he abandoned his thoughts of bodybuilding. He, like many other males, figured, if he couldn’t be the biggest, then why bother. This day found him in the company of his Manager, Sally. Being that he was a Junior Executive, Sally chose him to work with her, hand in hand, on a new project that their firm had been assigned. He was nervously happy when she had told him about their closer working relationship. He had hoped that he could keep his mind on the task at hand, and set aside his attraction to her. It wouldn’t be until a day later from a co-worker, that he would find out that Sally had just finalized her second, brutal and bitter divorce. So, the new team of Sally and Sean began the new assignment on a Monday. Sean arrived a half an hour early to work, only to be surprised that Sally was already in her office and leaning over her desk, peering at some papers. When sally had sensed another life form, she glanced up, then smiled brightly at Sean. “Good morning, Sean.” “Good Morning!”, he replied through his surprise. Sally’s soft perfume wafted through the air. Sean stood at the door and breathed in her wonderful aroma. He instantly noticed that Sally had already removed her jacket and managed a quick glance at her cleavage as the soft fluff of her white blouse accented her tanned breasts, while she leaned over her desk. “I. I'll be right back. I just need to...”, Sally cut him off and told him to relax and to come back after he settled in for work. His emotions were running wild. A new assignment, the first time he worked hand in hand with the boss, and to top it off, a raging hard on! By the time he made it back to Sally’s office, she was now sitting behind her desk with a cup of coffee, and appeared to be relaxing. She asked him if he would like to get a cup of coffee or tea. He opted for the tea, and went to the credenza and nervously proceeded to make a cup of Earl Grey tea. “So, how was your weekend?” she asked. “It was Great! I went to the family cabin in the North Woods. Got in some good hiking and some kayaking on the Silver Dollar pond. It was very relaxing.” How was your weekend?” he replied. Sally smiled, “Mine was the best I’ve had in a very long time. Since February, a year ago, I’ve been embroiled in my second divorce. It has been a very nasty one this time. But Friday, it was finalized. I spent the entire weekend purging my thoughts of it. I don’t think there was a single time from Friday, until this morning, that I wore a single stitch of clothing. I felt more free this weekend than I have in ten years, and that was my way of symbolizing my feelings.” Sally had noticed Sean’s glances in the past, and just couldn’t resist playing on them. She watched with glee as he squirmed in his chair when she told him about being nude. It had been a long time since she felt like dealing with the hunger of a males desire. And she was enjoying this play. The two got busy on their new co-project and the time whizzed by. They had lunch together each day, and were virtually inseparable for the entire week while at work. Finally, Friday rolled around, and it was just after lunch. They were only an hour away from finishing the arduous work. The ensemble that Sally wore this Friday, was an outfit that she hadn’t worn in about a year. It was the same business type suit as were all of her others, but the cut was different. The skirt was about three inches higher than usual, placing the hem line at the high thigh area. Her blouse was a plain cut, sleeveless with a low vee front. Her ample breasts created a full, deep crevasse for cleavage. And her make up was impeccably applied, her hair with a beautiful healthy shine, and of course, her perfume dabbed on every pulse point. Sean had found himself having a great deal of difficulty in concentrating on their work because of his rampant desire. In fact, Sally had asked him a couple of times during the morning if he was okay. He would reply quickly, that he was fine and just fatigued from the grueling pace that they had kept all week. He may have thought she believed that, but he was wrong. Sally walked to the window of her office and opened it partially. When she did, the papers on her desk, their project, began to blow onto the floor like confetti. She quickly pulled the window closed as Sean began to kneel and scramble around, collecting the scattered papers. Sally watched as Sean gathered them. She noticed the thick muscles work in his forearms, as the shirt sleeves were rolled about mid way up his forearms. She gazed at his neck muscles and his broad back while he collected the papers. It had been a very long time since she had been with a man, and she was becoming very aroused. His innocence, his age and his desire inflamed her depths. Sally waited for Sean to move to the last few papers on the floor while he was crawling around before she walked right up to the remaining pile. Sean retrieved the last clutch of papers at her feet, then slowly began to rise. Her shapely legs were an inch or two from his face. When he lifted up, slowly, he looked at every inch of those beautiful nylon covered legs. He was now at the hem line of her thigh high skirt, just several inches away from her womanhood. He noticed a shiny small streak at the inside thigh of her nylon on her leg. At that very instance, he knew what it was. It was excitement that had trickled from her punani onto her nylon. He breathed in deeply. He could smell her excitement! When he stood up, Sally smiled and said in a coy voice, “Oops”. Her face told him what he had hoped, as she was staring directly into his eyes. Her eyes were becoming almost iridescent with their coloring from her excitement, while his were almost glazed from his desire. He was aware, but didn’t care that his rock hard erection was creating quite a bulge in his trousers. He thought through the quagmire of desire and lust that engulfed his mind and body before he spoke. He wanted so badly, to throw her down onto the desk and take her right then and there, as if they were doing a scene in a Hollywood movie. Instead, he offered her a weekend at the cabin in the North Woods. After all, it had been a very long and difficult week, and her look of enticement when he told her of his weekend there. He felt that if she accepted, then they could become perhaps, closer in a more relaxing atmosphere. He was elated when she accepted. But there was a catch. She asked him if he would accompany her to the parking garage to help her with her car. It seems that it has been not wanting to start and she didn’t want to be stranded. Of course he agreed to help. So they gathered the papers back onto the desk, and left the office. She told him to meet her at the Executive elevators after he gathered his Jacket. Because they left an hour or so earlier than the rest of the office, they were the only ones at the elevator doors, and because Sally headed there first while Sean gathered his belongings, no suspicions were raised. The elevator doors silently slid open, and the two of them entered the cube. The walls and ceiling were adorned with gold tinted mirrors, and soft jazz music played on the overhead speakers. The doors closed as silently as they had opened, then the car lurched ever so slightly as the car began to descend to the garage level. Sally went to the opposite side of the large cube from where Sean was leaning against the tinted wall. She had removed her jacket and had it draped over her arm along with her small purse. She kept direct eye contact with Sean. She then stood against the opposite wall, legs about shoulder width apart, then leaned backward. Her skirt rose as she leaned. She smiled at Sean as his eyes devoured every morsel of her exposed flesh. His eyes gleamed as he looked directly at her hem line. He could see now, why there was that little streak of moisture on her nylon. She had no panties! He licked his lips as he leered at hers. In the shadow of her skirt, he could see the curvature of her of her pouting lips as the blended back to her backside. Sally motioned for him to come to her with her extended fore finger. He walked to her eagerly, and pressed his body against hers. Sally pulled the emergency stop button, causing the elevator to glide quickly to a halt. They breathed in each others intoxicating scents, as their bodies began to writhe against each others. Sean tugged upward at Sally’s skirt, while she adeptly yanked Sean’s trouser zipper down. His hand began to caress Sally’s wet hot pussy as her hand grabbed, then pulled his solid steel like cock from his boxers. Her leg lifted as he pressed forward. His throbbing cock entered her soft hot pussy, easily. They were completely coupled and he began to jab at her feverishly. Her hips bucked back at his onslaught as she wrapped her arms around his neck, pulling him into her tightly. Within a minute or two, they both were releasing their energy of lust and passion from their bodies. Sean must have fired off four or five long hot bursts of cum deep inside of Sally. Sally’s pussy grasped at his cock, convulsing several times very hard and quickly, before subsiding into slower deep twitches, bathing his spewing cock shaft with her juices. They separated after holding this position for several minutes. As they regained composure and straightened their clothing, Sally pushed the stop button and the car began once again on its descent. Once at her car, Sally asked what time would he pick her up on Saturday to go to the cabin. Sean smiled and replied around ten. He then opened her door and made sure the car started before walking to his vehicle. Sally stopped as she rode past Sean. She smiled and asked,” Should I dress up for tomorrow?”, then sped away. please give feedback, good or bad. Dress Up For The Girls Next Door I’m just your ordinary guy, you know the type, women love me, I’m an electrician by trade and there isn’t a single or married woman out there who hasn’t asked me, “Can you really install my ceiling fan for me.” 6’, 200 lbs, brown hair, blue eyes, I keep active so I’m not out of shape. So what happens with the ones I hook up with, why do they end up dumping my ass? Usually, it starts out real simple. I forget something. Then, it’s because I just don’t care enough to listen to her. And then it’s because I’m just not mature enough to have a serious relationship. Why, because I like to go to concerts and the ball game? Because I laugh at fart jokes, because I can quote lines from Animal House but I can’t remember to make plans for the weekend. So I like to fish and play pool. So I like to “waste” money on my 68 Camaro or ride my quad with my buddies in the woods. Hey, I work hard and I play hard. I do stuff with my girlfriends all the time, so just give me space once in awhile and don’t analyze everything I do. Your comfortable going to a counselor, that’s cool. I tried it, it didn’t get me anywhere. So the sex is the best you ever have had, I love pussy and getting you off is my number one priority. But you had to go and ruin it by saying your no good because I won’t cum inside you. I do, sometimes. She likes to suck my dick and that got me off all the time, except for when you would push my hand out of the way, hell, you stopped using your hand all together because you felt like I did that enough. So if it got me off, what’s the problem, oh that’s right, you feel like I don’t need you. Then you wonder why I won’t fuck you anymore, because why bother if your just going to get all emotional when I don’t cum in you. Go to a doctor, blah, blah, blah. Then I met Lisa, and she changed my life. She was like no other woman I had ever been with. Hot looking, 42, twice divorced, she held up very well. And what was it you might ask that kept me coming back for more, it quite simple, you see she takes control, total control. Lisa worked in the office next door. Her and Karen had a nice business going. They had been friends for 20 years. Lisa brought her onboard and the business took off. What they imported was beyond me, but there they were, two hot blondes working next door. It started out easily enough, our conversations often turned to sex. I’d talked to them alone and together. I’d tell them anything and they shared their desires as well. Karen was the more reserved of the two, but what a set of tits. They were big and round and firm. They bounced when she walked. The summers were the best, they wore the hottest clothes, and let’s not forget about the sandals! You see, I have a fetish for open toed sandals. So when the packages came from Spiegel and Victoria’s Secret, I was always asked my opinion. So Lisa and Karen were changing in the bathroom when I walked in the office. “Close the door and sit down”, I did as I was told. Out comes Lisa in a very hot two-piece bikini, with Karen right behind her in the same. I said nothing, but my mouth was open. They walked in front of me and turned to show me their ass. Lisa bent over and Karen did the same. Lisa walked over to my chair and straddled me, pinning my arms down. She looked me in the eye and smiled, she leaned forward and shook her tits in my face while slowing beginning to gyrate on my lap. A lap dance, and she was very good. Her hips gyrated into mine, her pussy rubbed against my stiffening dick through my pants. I started to speak, when she leaned forward and said, “ssssshhhhh, just watch and enjoy.” Karen and Lisa returned to the bathroom, which was around the corner. The suits they had been wearing came flying across the room. Did I mention the giggling, they were giggling like college girls. They came back into the room, oh those bikinis were hot. There was nothing to them and this time Karen came over to my chair. Her tits were barely covered, I could see her hard nipples stretching the skimpy cloth. She straddled me and I was able to reach up and play with her tits. She moaned as I kneaded her nipples and massaged them, all the while trying to work her top off. She let me work my hands under the top and let those tits free. What a sight! Then she totally surprised me by leaning forward and letting me suck on her nipples. I was in heaven. And just like that, she went back to the bathroom, giggling away. Lisa had made her way out, she was wearing a very hot bra with very skimpy panties. The black thigh highs outlined her perfect legs, she even wore some very slutty black pumps. She told me to relax and enjoy myself. She straddled me and once again began to give me a lap dance. I reached up to play with her nipples and she slapped me across the face. Her hand grabbed at my now hard dick as she leaned forward and spoke to me. “You like this don’t you. I’m in control, do you understand.” All I could say was, hell yes. Her tits were let out and once again I reached up to touch them. She slapped me harder and I turned away. “In good time,” she said. Her ass is so hot. She had bent over in front of me. The outline of the back of her stocking was such a turn on. Between her bending over and fingering her shaven pussy, I was going to lose it. Somehow, I had unzipped my pants and pulled out my dick. Lisa turned and saw me playing with myself. Then she turned and left me, with my dick in my hand. More giggling from the bathroom followed. Karen and Lisa both called to me and told me to join them. I pulled my pants up and walked towards the bathroom. There standing before me were two of the hottest women I had ever seen. They were dressed in leather, Karen was topless. Her tits were beautiful. Lisa had a tight leather skirt on and a very skimpy top on. They were both wearing fishnet stockings and garters, and the boots, oh the boots, were just too hot. Lisa took a swipe at my ass with a riding crop she held in her right hand. “Strip”, that’s all she said. I stood there naked for a few minutes. They were kissing, French kissing, very slowly. My dick was getting hard once again. That’s when they started to talk about what they were going to do to me. “We saw you watching porno on your computer, you’re pretty fucking kinky.” Lisa was sucking on Karen’s tits. “Jerk off for us.” They didn’t have to ask twice. Karen was told to get on her knees. She did, in front of Lisa. “Join her” Lisa smacked me with her riding crop. I joined Karen in front of Lisa. “Keep your eyes straight ahead”, Lisa ordered. Karen and I lifted Lisa’s skirt, she had a strap on dildo staring me straight in the eye. “Suck it, you know you want to.” I had spoken to Lisa about this once before, about her dominating me. But never in my wildest dreams did I think this would happen. I didn’t hesitate, I took the tip and put it in my mouth, then I took the entire length. Karen reached down and began to stroke my hard on. She whispered in my ear, you’re so good, I know all about you. I worked the dildo like a real dick, sucking and licking, nibbling on the head. Lisa grabbed the back of my head and worked her hips into my open mouth. “That’s it, suck my dick slut.” Karen was letting me play with her tits as I sucked. She slowly removed my hands and led them down her belly. She began stroking my dick and leaned into say something to me. “We are going to treat you like the whore you want to be.” She took my hand and placed it on a strap on dildo she had between her legs. She made me stroke it as I sucked Lisa deeper into my mouth. We went upstairs, they locked the door behind them. There was a couch and a desk up there. They were both very turned on, as was I. “Put these on”, Karen handed me a bag. Black thigh highs, a lacy bra and panties, I quickly put them on. I had told Lisa I liked doing this, I made a video of me wearing her panties and stockings. I jerked off and swallowed my cum for her. I told her I would do anything for her, even suck a real dick. That was months ago. Karen then told me to sit at the desk. She began to apply lipstick and rogue. The eyeliner followed and then the wig. The black pumps were a little tight, but I managed. They both stood back to admire their work. “Look at that slut. I bet he will let us do anything we want to him.” They were right. “Stand up slut,” Lisa ordered. Her hand was on my ass, probing at my hole. She worked her lubed finger in and I exhaled. Karen was slowly stroking my now hard dick, which she had freed from my panties. Lisa led me over to the desk and ordered me to bend over. Two, then three joined her one finger. I moaned a little more. Karen had jumped up on the desk and began working her strap on into my mouth. Then I felt Lisa begin to work the head of her dildo into my tight hole. I was in heaven and she knew it. Some of my lipstick left a red ring on Karen’s dildo, they both laughed as Lisa began to fuck me. She worked the dildo all the way in, I moved my hips in unison with hers. “Your such a slut, you like getting fucked in the ass, don’t you sissy.” Lisa smacked my ass as she fucked me harder. “Look at you with your pretty panties down around your ankles, look at you suck Karen’s dick. You’re a cock sucking whore.” She started to fuck me faster. “Tell me you want it, tell me you want me to fuck your tight ass like a pussy.” Her hips were pounding into me. “I want it, I want you to fuck my ass like a pussy.” I couldn’t say much more. I looked to the side and caught myself in the mirror. I was sucking and fucking like a whore. “I want you to be ready because you’re going to suck a real one for us, right slut.” I muttered yes, Karen was working her hips into my mouth and she was getting off. “And from what I can see you would have no problem taking a real one up your ass either.” I muttered yes again. “That’s good, real good.” Lisa was a fucking me and spanking my ass. My dick was ready to cum. Karen had stopped working her dildo into my mouth to concentrate on my dick. She took it into her mouth and I exploded. She took all my cum and milked me for more. Lisa was still fucking me the entire time. I couldn’t stop cumming. The white streams filled Karen’s mouth. When I was through Karen brought he lips to mine and shared the load with me. It was a lot, we kissed and she gave me all the cum. Lisa told me not to swallow it, not yet. She began to slow her pace and then removed the dildo from my ass. “Open your mouth slut.” She looked in and smiled. “Good, now swallow it just like you did in the video.” I loved every second of it. Lisa had shared my video with Karen and they had been planning this for some time. I would often IM Lisa and Karen was right there, reading the messages the entire time. She knew all along what I had dreamed about doing. The girls looked down at me with satisfied faces. Lisa then bent over the desk and Karen began to fuck her very wet pussy. I played with Karen’s tits, sucking on her nipples. She began to pick up the pace and fuck Lisa hard. My finger found Lisa’s clit and I rubbed it in time to Karen’s dildo going in and out. Lisa let out a scream when she came, my dick was hard once again and I wanted to see if she would suck it for me. I positioned myself in front of her and she took my dick in her mouth without a fight. She stroked it and worked it nice and hard. Before you knew it, I exploded into her mouth, except for this time she swallowed it all. We were all sweaty and panting. The shower downstairs worked and we all headed down to clean up. This was just the beginning of a wonderful summer.