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The Holiday Party

By: jack30341



As I am writing this, I still can't believe this happened to me. It seems like a story I want to tell about someone else. I mean, I'm the typical conservative-looking soccer mom type, who would never be suspected of going through with anything mischievous, much less scandalous.

At 5'8", and about 130 pounds, I have short blond hair and blue eyes, with what I've been told is a "cute" look similar to a Meg Ryan type. All I know is that I try to take care of myself and work-out regularly to take away the stress of being a single parent. 

My ex left not too long ago when we just could not stop arguing. It got to the point where my 21 year old son even knew my ex-husband was harrassing me too much and talked him into moving out. Before long, an amicable divorce happened. Then, my daughter left for college and my son, Bobby, stayed to attend a local college for a while like his older sister had before she left.

My son and I went in our separate directions for the most part, but now with him older, it seems we relate to each other more easily, and we try to do something together at least once a week to keep up with each other.

It was with this routine that he agreed to go to my office holiday party with me. I was complaining about having to go all alone, and he tried to lift my spirits by saying that I didn't have to go alone, that he'd go if I wanted. I thanked him and said yes, that I preferred that.

The party itself was okay. I work for a large corporation, and an entire ballroom was used to have it. There was dancing, food and plenty of drinks, which I readily had my part of.

So did Bobby. One of my friends was seeming to want to monopolize Bobby, but who could blame her. At 6'1" and a lean 195 pounds, Bobby is attractive, fit and ---well---only 21. My friend called him a stud to his face, and he only blushed turning to face me and shake his head.

He did manage to save a couple of dances for me, and really surprised me when he saved the last one for his certainly buzzed mom.

"Thanks dear," I was sure to tell him, "you are such a sweetheart."

"Mom, you make it easy to be," he charmed.

" Well, I'm afraid I've had too much good cheer," I confessed.

"Yeah, me too," he responded.

After some thought, we decided the best idea was to stay the night at the hotel. We got a room with a couple of beds and headed upstairs.

At this point, it did seem a little strange. He was older. An adult now. We'd danced together. My friend had talked about him in an adult way that had given me pause. But, he was my son ,and I thought nothing of us staying overnight rather than taking the risks of drinking and driving.

It was quiet in the room as we both got ready for bed. Ever the gentleman, he insisted I use the bathroom first. And when he went in, I was struck about what I'd sleep in. I quickly shed my clothes and crawled under the covers of my bed, feeling warm and cozy and content to sleep the same way I do at home.

He came out of the bathroom and he was at first perplexed, too. But after a short pause, he took off his watch and just casually pulled his shirt over his head. My gaze went to his chest and the light covering of hair that matted on his chest. Without thinking, my look drifted to where his tight abdomen met his trousers and the trail of hair that disappeared into his pants.

It was then that I noticed he was standing still. Facing me, I saw that he had a grin on his face as he looked back at me. I thought I would die. I realized that he'd caught me staring at him and I realized I'd taken my time with surveying his chest and stomach. I immediately looked away, embarrassed. 

I sensed him moving and looked back at him. He was undoing his belt and taking down his trousers right in front of me. I absolutely could not help myself, and I watched him. He knew I was watching and seemed to take his time. He pulled on his trousers and had them slide over his hips and then let them fall on down to the floor. 

As he looked down to step out of them, my jaw dropped as I looked at the sight of him in white boxer-briefs that now was the only thing covering him.

The underwear did little to really hide the bulge that protruded out and down the left side of the leg of the shorts. It looked as though he was confined there and that he would be exposed with much more movement. 

I looked to his face and he looked back at me. We said nothing. All I could think of was how I had openly stared. And how he was no longer just my son but certainly a man.

"Look, we should get to bed," I finally said.

"Yeah, you're right," he agreed and went to the light switch, turning it off.

I laid there and listened as he got in his bed.

"Thank you, Bobby. You were so swweet to go tonight." I said to him in the darkness.

"Sure. I had a great time. I'm glad I went."

"Me too."

The room stayed quiet a while, and I chastised myself for the clearly wicked way I had acted before. I felt horrible guilt already. I could hear Bobby toss and turn a little bit, and I did the same.

"So are you sleeping in your underwear, too?" He asked me.

"I'm sorry, honey," I said in a low voice," I should have given you some privacy before."

"No, no. Don't worry about it. It's just I'm not used to sleeping in my underwear is all."

"Yeah, I know what you mean." As soon as I said the words, I figured I'd said too much. Did he take it to mean I'd taken mine off? I heard him get out of bed and heard him moving. I turned on my left side facing away from him and tried to listen for what he was doing.

The covers pulled down somewhat on my bed as he was climbing in with me. I was shocked. What should I say, I wondered.

"I can't sleep. Can you?" He asked in a low voice.

I was facing away from him and utterly aware of my nakedness. I could feel the warmth of him although he hadn't touched me. I tried to figure out what to do to gently tell him this wasn't a good idea.

While I searched for the right words, I felt his hand touch my shoulder. He gently rubbed the top of my shoulder and I felt my shoulder droop ever so slighly at his touch. What was happening here, I thought.

His hand squeezed at the shoulder and the skin at the back, giving little quick squeezes to try to massage the muscle there. He rubbed a little harder and pressed more of my back as he did so in a comforting and soothing way. I still said nothing.

After a moment of this, he moved his hand so that only his fingertips were on my skin. Then, he traced my bare back with his fingertips, first at the shoulders and then sweepingly across my back as if making light circular motions.

It felt soothing, and at once erotic, and I again told myself to come up with something to put a stop to this. Then, my mind reasoned that he was just being nice and that nothing more could come from it. Surely, he wouldn't try to do anything to his own mother laying there, I thought. I was probably taking all of this wrong. 

I felt his hand come to rest on my hip, and it struck me how he must now have known I was in the nude. The hand was at the place on my hip where it starts to curve outward.

His hand was still for only a moment. I breathed deeply, and I felt it go to my stomach. When his hand was flat against my stomach, I uncontrollably sighed heavily. I immediately wondered what he thought.

I had said nothing. I hadn't moved. His hand was on my bare skin. I felt my nipples responding, and a very familiar reaction between my legs, as I tried to anticipate what would come next. Surely, he was just being loving and would stop now.

His hand seemed to stretch out and I thought of its size. I mentally scolded myself for even thinking this way. He slowly moved his hand in a circular motion as if to stroke my tummy. On the third or fourth time around, the radius caused the last two of his fingers to brush my pubic hair. I knew that he had to have known he'd felt me there. 

Two more brushes around and his hand stopped there. I then felt him scoot his upper torso toward and felt his chest against my back. I said nothing, and I didn't move. I had to stop this, I thought. What is happeneing here? At what point will he stop? I thought about how I could move my hand to his and move him away. Yet. I did nothing.

His hand lifted again but his fingertips rested on my pubic hair there. I squeezed my eyes tight in the darkness as I felt his fingers stroke the top of my mound. I had said nothing, so he figures I'm condoning this, I thought. All I have to do is tell him to stop. When it gets too far, I'll have to tell him, I decided.

As if instinctively, my right leg moved a little back, as if on its own and I realized the message this must have sent. The movement left my right foot touching his foot and the touch there seemed to magnify the intensity of the situation. He and I both knew the effect of this little move with my top leg, exposing me ever so slightly more to his touch.

With this thought his hand moved further down and he cupped my mound. This was overtly and unmistakenly a sexual touch, as his hand held me there. 

"Oh," I whispered with a heavy breath.

His second and third fingers were far enough down to feel my slick lips there, and for the first time he was certain of the effect he was having on me. I again knew I should act to stop this, but I did nothing to resist. He gently squeezed twice, letting his fingers press to my wetness.

"Uuhhhhhhhhh," I couldn't help but respond as he manipulated my crotch with his hand.

He let his two fingers brush just up and down my dampness along my lips. I almost was panting I was breathing so hard. I knew I had to stop him now, I thought.

The very next thing I knew I felt his other hand at my back. He pushed there against my back and I felt my torso ease forward, moving until I was bent at the hips, while laying there on my side. I was bent over with my ass facing toward him.

There was a pause as I tried to orient myself to what was happening. My son had bent me forward with one hand and used the other hand to hold my pelvis to where it was still close to him and exposed to him.

The bed moved, as he positioned himself closer to me still. He moved his hand from my crotch to put it to my legs, reaching between my legs as if to pry at my ass.

Then, I felt it. I felt the warm hardness of him and immediately thought about his thickness. His head was resting against my lips, and he was moving it to rub hard against me there. Even though I was very wet, my lips didn't yield easily at first. He sawed at me, parting my lips, and I tried to stay still and not react, bewildered that this was even happening. But, I had to admit it. He had me as wet and wanting it as much as I ever had before.

"But, Bobby," I said weakly," I'm your mother. ..."

His hand at my hip pulled at my ass further and he thrusted, pushing his head and a couple of very hard inches into me.

"OOOOOOooooo," I exclaimed, sounding like I had been hurt suddenly.

He slightly pulled back and then thrust hard against me causing me to grunt. I was impaled on him and he was deep inside me, pulling my lips and my clit along with his shaft. His thrust had caused me to move over some on the sheets, and I pressed my hands down to brace myself.

He quickly pulled his hips back and my lips clung to his shaft as it moved. With only a brief pause, he pushed hard back inside me and this time he went all the way in me, causing me to moan uncontrollably again.

"OOOOOOoooo," I bellowed from my throat as he started moving back and forth inside of me. An orgasm shook me as he took me from behind. He could feel me, his mother, shudder as he swayed on the mattress, rocking his cock back and forth in my warm wet pussy that clung to him.

"Bobby," I was listening to myself and unable to believe it was me grunting back at him, "baby, that feels so good."

"Yeah?"

"Go ahead," I urged him on, past being able to start caring, "go ahead and give it to me."

With that he pushed harder and started fucking me in earnest, moving in and out faster and letting me feel the length of him push in and out.

He too started getting into a constant moaning and I wondered how much longer he'd last.

I could feel him deep inside on the up thrusts.

"Yeah, Bobby. You like that baby? You like fucking me?" I urged him on.

He fucked me harder and I again felt an orgasm coming on.

"You're goonna make me come again. ..." I told him, and it made him get louder.

"YYYYEEEEAAAHHHHH" he exclaimed as he came hard inside me, with me right with him shaking as he pressed inside of me.

"YEAH, yeah, give me all of it, Bobby."

Now he was shaking as he held tight against me. We stayed joined at our sex. 

I fell asleep this way, feeling him there.

Groggy, I came to a little later. Disoriented, I looked about in the darkness trying to remember. I was laying on my back and felt movement in the middle of the bed. I felt hands there at my legs pulling them apart.

Next, there was the unmistakeable feel of a mouth and lips kissing me at my vagina. 

The Holiday Party



I looked in the mirror at my handiwork. My wife had asked me to shave all the hair off my cock and chest and I wasn't in a position to say no. After eight months of no sex, I was going to do whatever she wanted if it meant I'd finally get a sexual release.

It looked funny, my body all bare for the first time in years. I felt kind of embarrassed, as if part of my manhood was stripped from me and dropped to the floor to be swept away. I felt both ashamed and excited at the night ahead.

Ever since she had the miscarriage things had been different. She kept me at a distance. I don't know if she was depressed or afraid but there was little I could do for her. Finally, I felt, she was coming out of her shell. Finally we would be together.

I slid my pants over the bare skin. She had said how sexy it would be if I went without any underwear tonight. The thought of her words sent a gentle throb to my loins. She knew how pent up I was and that even hints of sexuality were sending me mad. Carefully I pulled up the zipper, tucking myself in as best I could, though feeling it wouldn't help keep me in place.

I finished getting dressed and waited for her to come home. I was ready to go to a holiday party, but in reality I just wanted to stay home.

"You did what I said?" she smiled at me in the car on the way to the party. She was beautiful, big brown eyes, beautiful brown hair. She had worn a tight blouse that accentuated her breasts and made my cock shift uncomfortably in my pants. 

"Yes," I looked out the window at the festive lights and thought about how it felt. How badly I wanted this party to end so I could get on with the night.

"Let me see," she squeezed my leg. "No one can see, unbutton your pants."

I looked at her. She must be kidding. I glanced around at the well lit street, all the holiday shoppers bounding from store to store. Would any of them see if I showed her? I felt my loins stiffen. I wanted to show her.

I looked at her and fumbled with my pants until they were unbuttoned. I pulled the waist down to reveal my clean shaven abdomen. 

"Your cock silly," she squeezed my leg again and put the turn signal on to turn left. The car came to a halt.

I looked at her. Anguish filled my face but I reached to the waist band and with another hand pulled my cock and balls out for her view. I shuddered and quickly whatever stiffness I had failed me. While I was still turned on, the fear I felt of showing myself to her in public had trumped those feelings.

"It's sexy," the car slowly pulled forward and made its turn. 

"I want to tell you something hot," she leaned over and whispered into my ear before we got out of the car to go into the party. "Tonight the only layer between you and any of my coworkers is your pants."

Though I didn't know why, the words sent chills down my spine. 

"There's no underwear or even hair there," she leaned back and smiled, "so when they touch you, they're only one layer removed from feeling your skin. That is going to make me so excited all night."

My cock got hard and I knew that I couldn't hide it from view. I was going to have to sit in a corner all night. I could feel the power of her words haunt me as I entered the crowded room. I felt naked in a full room.

"Don't be shy," my wife grabbed my hand and pulled me into a conversation she was having with two attractive blonds. "This is Amber and Nicole. They're the new admins."

I smiled and nodded. I felt as if they were looking through me. Like I was small. I could barely manage a conversation. 

Then I felt my wife slide her hand over my butt cheek. My cock instantly sprung to attention inside the pants. I felt horrified and shifted unconsciously, trying to hide my embarrassment. 

"Honey, can you get more champagne," I felt her squeeze my bottom, sending my cock twitching. I prayed the girls couldn't tell. 

"There's a two drink limit," Nicole smiled and grabbed my hand, "I'll go with you."

I started walking, grateful I had Nicole to at shield, at least some of, the view. Though probably no one was, I felt like everyone was looking at me as I walked through the crowd. Looking at the uncomfortable stiffness in my loins, pressing freely against my pants. The thought was planted firmly into my head and I couldn't shake it.

The line was incredibly long and very tight. People squeezing harder and harder against me. I fought as hard as I could to lose the thought of how close my skin was to them. I felt naked, embarrassed and excited. 

Nicole stood in front of me making small talk. She was achingly close to my hips. It was all I could do to shift away from her as she was bumped or shoved towards me. I was in fear that she, or someone else, would find me hard against them and that scared me. It was torture, feeling them brushing against me, so close to my bare skin. I could barely function.

"It's our turn," Nicole smiled and turned towards the bar as we finally had reached the front of the line.

Suddenly I felt a shove against my back and my body was lurched forward. I froze. All the blood rushed from my face in fear. I felt my semi-stiff cock pressed lightly into Nicole's dress, right between her cheeks. I tried to pull back but, for at least a moment, there was nowhere to retreat. I gulped in embarrassment.

"Sorry," a voice called out from behind. 

I pulled myself back from Nicole and looked away. I was afraid of what she would think. Was she going to think I was excited talking to her? I wanted to crawl into a corner somewhere. Why did my wife do this to me? Why did she plant the thoughts into my head? At first I thought it was sexy, now it was excruciatingly painful.

"Here are your two," Nicole smiled and handed me two glasses of champagne. She looked into my eyes and smiled. How I prayed at that moment that she didn't feel me.

We walked back both of us balancing the champagne amid the crowded floor. Whether or not it was my imagination, I felt constantly brushed against and touched. I tried to stand clear of everyone, but someone would always shift at the last minute, pressing their body against mine and reminding me. It was both exciting and horrifying.

"That was an ordeal," Nicole handed Amber one of the champagnes, smiling. "I was just trying to order our drinks when your husband got all fresh with me."

I gasped. 

"All of a sudden he lurched on top of me," Nicole winked at me, "he tried to blame someone behind him, but I think he was being a bad boy."

What did the wink mean? Her tone was joking, but she had to had felt something. She wouldn't know, but the teasing was tormenting me. I was so embarrassed. I looked away, ashamed, afraid to look at any of them. I wanted to leave.

"A bad boy you say," my wife smacked my bottom lightly, "we'll have to have a talk later."

I felt my cock begin hardening ever so slightly. It was torture the constant feeling of arousal amidst all these people. I felt dirty and used and at the same time I desired a sexual release more than anything in the world. I needed it.

The girls giggled. The thought of me being punished sent them into a teenage time warp that seemed to never end. They were giggling at my expense and only one of them knew what it was doing to me. I looked around.

The party went on for what seemed like forever. I tried to find a place to stand where my loins wouldn't be seen, but there were few tables and fewer chairs. I was stuck standing and when I wasn't being touched by my wife, people were constantly bumping into me.

Nicole kept looking at me and smiling. By this time I felt she knew I was hard when I fell into her. I wondered what she thought? Did she think I was dirty or was it exciting? I never knew what was going on in a woman's head and this time I was at a complete loss. 

The night wore on and my sexual tension grew and grew without abatement. The torment of being humiliated along with the excitement of knowing it was soon going to be done overwhelmed me. 

"Don't I get a hug?" Nicole looked at me smiling in jest, "Just like a man, love them and leave them."

She held her arms out and walked towards me. My whole body froze in fear before I could compose myself and lean out for a polite hug. I gulped, afraid she'd feel my stiffness and misunderstand. I reached around her.

She pulled me tight until our bodies were embracing in a friendly hug. I felt myself slightly stiff against her and gulped. I didn't want her to feel my like this. I felt so embarrassed.

"What about me?" Amber smiled. "You're hogging him."

The torment was excruciating. I felt my wife touching my back and rubbing me as I reluctantly leaned in to give Amber a hug. 

"I think I had too much to drink," Amber fell forwards into my arms and grinned, her nearly empty champagne glass tipping wildly left to right. 

I pulled her up and she quickly grabbed my shoulders in a tight hug.

"Thank you for saving me," she whispered into my ear, her body tight against mine. 

There was no hiding myself at that point. I knew she could feel me against her thighs. It felt like she was never going to let go. Her arms holding me in her shaky embrace.

"You're driving her home?" I looked at Nicole and slowly shifted Amber towards her. 

Nicole nodded yes.

As my wife and I walked out of the party, I finally felt like my night of torment was nearly ending and all my pent up desire would soon be flooding out. 

"You were sexy in there," she squeezed my hand tight, "really sexy."

The drive home was excruciating. She kept talking about how she could tell when I was excited because I kept shifting my body to avoid exposing myself. Her words kept coming, but all I could think about was the stiffness between my legs. How I wanted that to end. How I wanted to feel myself deep inside of her, my seed exploding from me.

"I bet you're ready to explode," she looked at me as she parked the car in the driveway. "Too bad you'll have to wait until I'm done with you."

I looked at her. What was she saying? I couldn't wait any longer. At that moment I was in fear that I would burst when I took off my pants. 

"I can't wait," I looked at her pleadingly, "I really don't think I can wait."

She smiled and opened the door without an answer. I wondered what she was thinking as we silently entered the house and went towards our bedroom. 

Finally she broke the silence.

"We're you excited?" she said, barely looking at me. 

"Yes," she knew I was excited. We had talked about it the whole car ride home. 

She slowly removed her skirt and began working on her nylons. 

"Would you be more excited if I told you that Nicole and Amber knew all about tonight?" She looked at me with a devilish grin. 

"You didn't tell them? Why?" I looked at her angrily, but wondering if she was joking.

"I thought it would be sexy if they knew what a great husband I had, who would do anything for me," she smiled and walked towards me in only her bra and panties. "You will do anything for me won't you?"

I looked down into her brown eyes and then into her bountiful cleavage. I felt my body shifting and uncontrollably excited. I wanted her so bad.

"Of course I would," I bent down to kiss her but she pulled away before our lips could meet. 

"That makes me so excited," she lowered her hand to my loins, "that you would do anything for me."

She gently massaged me until I could take it no longer. I wanted to release then and there, but I wanted to be with her so much more. I wanted to lie with her and feel myself in her warm embrace. I pulled away at the brink of ecstasy. No, I didn't want a release that way, not then.

I looked at her as I quickly removed my clothes. My eyes drifting from her face down across her entire body. I wanted to jump on top of her right then and there. There was no holding back.

"I want you," I moaned my pants dropping to the floor around my feet. My cock throbbed hard in full view. 

"I see that," she smiled, "but we have some unfinished business to attend to. Nicole said you were a bad boy."

I chuckled.

"I'm sorry," I played along. "It won't happen again."

She got behind me and shifted my body towards our dresser. The feeling of her hands on my naked body was driving me insane. No matter where she touched I felt my body jolt with excitement. I was playing along, but I wasn't sure how long I could hold out.

"I don't want my boy being bad," she rubbed her hand gently over my bottom, sending goosebumps all over me. "You need to learn to behave."

She spanked me. Not just a gentle spank either, a really good spank. I felt both excited and the sting of a slap. She had never done anything like this before. I wondered what had come into her.

"Tell me," she leaned over and whispered in my ear, "were you hard for her when you fell into her lap?"

I felt my cock jolt up hard.

She pulled back and spanked again and again not waiting for me to answer. Each spank sent waves of excitement and pain through my body. The need for imminent release slowly waning, but my cock still stood stiff. Finally, after several smacks, she stopped and panted.

"That should teach you to be a bad boy," she panted. "I don't ever want to hear anyone call you a bad boy again."

At that point I didn't want it either. I had never been spanked before and it stung. I didn't know what to make of my wife. What had come into her? It was exciting and disturbing. She was not the woman I was used to.

"Don't you want to be my good boy," she reached her hand between my legs and gently lifted my balls up. "I like good boys."

I nodded yes emphatically. I couldn't take it. Her hand reaching between my legs gave me feelings I cannot explain. I felt at her mercy, like she was controlling me. I felt vulnerable and at the same time it was exciting me beyond belief. I wanted to explode but she wasn't touching me to allow it to happen. My cock twitched violently searching for a release it wasn't allowed.

"Please," I moaned, "I can't take it."

She removed her hand. I saw her smiling in the mirror watching the torment on my face. 

"So soon?" she feigned a look of dejection. "What about me? You don't want me?"

I felt my cock go completely hard, my pent up juices welling up inside of me. I couldn't hold back but I had to. How I wanted to be with her but how I wanted this torment to end. My body ached in pain for release.

"No, I want you," I moaned, "I want you so bad."

"Then come here," she crawled onto the bed and slipped out of her bra. "Suck on them honey."

She had never been so aggressive about sex before. She had never told me to do something and all of a sudden I felt she was commanding me and I felt helpless to say no.

I reached my hands out and felt her breasts. They were so full and sexy. Usually she held them back from me. She had told me several times how embarrassed she was of them but I tried to tell her how sexy I found them. Now she was commanding me to take them. 

"Not like that," she shifted her body underneath me, "like this."

She pulled my head into her lap and gently lifted her nipple to my mouth, pressing it into me. I took the nipple into my mouth and started to moan. Her hands drifting through my hair, gently pulling my head tighter towards her breast. The feeling in my loins again abated from excitement as I lost myself in the comfort of her softness.

"Such a good boy," she cooed into my ear as she shifted my head to her other breast. "Such a good boy."

The praise had an odd effect. It made me feel as if I was pleasing her but it felt so condescending. I wanted her to stop but I wanted to suck on her breasts more. I wanted to feel her touching me so softly. 

I felt her hand drift further and further around my body. From my hips to my face her hands explored me, careful never to touch my stiff cock. I could feel it jerking with ever more ferocity. I couldn't wait to drill it inside of her warmth. 

"My little boy is so sexy," she smiled her eyes drifted down from my bare chest to my shaven cock. "I didn't know how sexy you would look like this."

My cock shuddered every time I hear the word boy. I felt embarrassed that I had shaven and now she was calling me a boy. The words stung more than the slap of her hand had on my bottom. How I wished she would stop.

"What do little boys like?" she slowly pulled my head from her breast. 

She looked down into my eyes, my head still resting in her lap. I could smell her sex and it was driving me crazy.

"Honey, I just, can't we?" I couldn't find the words but I knew she knew what I meant. I needed to be inside of her. It had been too long.

"Does my little boy want me to touch him? Does he want me to lick him?" She watched my cock twitching with every word. "Does he want me to wrap my breasts around him until he explodes with joy?"

I lurched up. She knew she driving me mad. I wanted all those things but most of all I wanted to be inside of her right then. I wanted to explode deep in her and I wanted to do it then.

"I want to fuck you now," I groaned and started to shift my body on top of her, reaching for her panties.

"You don't talk like that," she pulled away and shoved me off the top of her. "I can't believe you would say that word to me."

I sat there in disbelief. My cock was throbbing and I was aching to get inside of her. I felt like she was taking this game a little far.

"Honey, I need you," I moaned trying to work my way back on top of her.

"Good boys don't say that word," she looked at me and waved a finger menacingly towards me. 

My mind was in a frenzy. I wanted her so bad I was going to burst and she was still playing her little game. It was driving me nuts. Every move I'd make to get closer to her she'd shift to make it nearly impossible for me to get near her. 

I pawed up towards her, trying to pull her to me, but she shifted yet again.

"Are you going to promise to be a good boy from now on?" She looked at me still waving the finger. "Are you going to be my good boy?"

"Yes, yes, anything," I stammered, pulling on her panties. "Anything just let me inside of you."

"Come to mommy," she moaned and I felt her hands reach down and shift the panties off until she was completely nude before me.

I fell on top of her. I was unable to contain my lust any longer. I eagerly entered her and began pushing up and down her with fury. In a matter of seconds I felt my seed spill from my loins. I couldn't wait.

She wrapped her arms around me and pulled me tight to her. My hips pushing up and down spilling every drop of my being into her moist warmth. It was as thoughts of her had filled my entire being. From everything I felt to everything I thought, I just wanted to explode inside of her. Over and over again I thrust into her until I was unable to move. 

I collapsed onto her, my head resting on her heaving chest. 

"Now that's my good boy," I felt her rub her hands through my hair. "You like being my good boy don't you?"

I gulped and turned my eyes to meet hers. She rubbed my cheek with her soft hand, bringing her breast to my mouth. I felt my cock twitching all over again. She was driving me mad.

"You like being my little boy, don't you," she rubbed my hair as I pulled the nipple into my mouth. Her other hand reaching down to my soft damp cock. "I like you being my little boy."

I felt my cock stiffen.

Why was she doing this to me? Why was I excited?



The Holiday Party



Author's note: I love writing first time stories in the f/f genre. This story is similar to my others, but not so much that you'll be annoyed if you read my other work. Full disclosure: there is a brief m/f encounter halfway through that is essential for the plot. Skip over it if you like; the main idea of this is f/f. I really take my time with this one. But if you stay with me until the end, I hope you will agree it was worth it. Let me know.

*****

I was 23 when I woke up and started to change my life. I was a little thick ever since I was a kid. I kept it under control in high school and even went to a small college in the Midwestern U.S. on a volleyball scholarship. But my weight got worse as I focused more on my studies, and I was cut from the team my Junior year. Picture the leggy blonde Kerri Walsh from the U.S. Beach volleyball team in her cute little bikini bottom. Yeah, that wasn't me. When I moved to Atlanta for my first job out of college, all exercise stopped, and my weight started to balloon. In the culture of the American South, I fit right in with little incentive to change.

Professionally I was doing great. I was one year out of college and had already been promoted into a first line management position and was being groomed for advancement. Spiritually I struggled like any good church-going youth, but I'd like to think I was on target there. But I had failed to develop any close friendships or find a boyfriend in Atlanta.

The boyfriend issue was really starting to annoy me. I was just over six feet tall, so naturally I blamed my woes on height. But I knew that wasn't it. I was overweight and unattractive. That might not be a deal breaker for a shorter girl in the dating world, but on a tall girl like me, it just made me look gigantic in a bad way. This started to affect my mood and self-esteem. I wanted a family one day. I wanted a career also, and while I knew hard work would pay off to a point, advancement to the top levels would require me to have all aspects of my life in order.

I joined a local Gold's gym, and I was at the end of a 90-day boot camp with my new personal trainer, Elena. I combined as many private sessions with her as I could reasonably afford with the group exercises like Body Pump, and I was definitely seeing results.

Elena was training me today, and I was warming up before my session. I had finally ditched the hideous loose athletic shorts in favor of a new pair of printed leggings. I looked in the mirror for the hundredth time since putting them on at home, and I was humbly impressed. I still needed to drop at least 20 pounds of pure fat to get where I needed to be. My muscles were filling in nicely as the fat melted away. I already had my best body as an adult, but there was lots of room for improvement.

One of the things that surprised me is how little traditional cardio I did, even though I knew I could run a lot further than before I started working out. Elena had me squatting heavy my first day in the gym. I'd never have a petite girl's thigh gap, that's for sure. But my legs looked good. My ass had the good kind of mass now, getting fuller in the right places even as I lost the fat. I had a huge rack before. The diet had taken its toll, but the slimmed-down D-cups that remained were firmer and had a nicer shape. I'd started growing out my natural blonde hair also and was finally almost at "bra strap length."

"Admiring yourself, Brit?" said the friendly voice behind me.

"You're the sculptor, this is your masterpiece," I said. Elena was looking gorgeous as usual. I was so jealous of her bodybuilder's physique. She was shorter, maybe 5'6" or so. She was a beautiful Latina with black hair and flawless olive skin. She wasn't too dark with fake tan like a lot of the gym rats that went to fitness competitions. Her bust was smaller than mine, although she made sure whatever she wore put it right out there for us all to admire. I sincerely thought she was the most beautiful woman I knew.

"Well I love the outfit. You can pull that off no problem. We're doing deadlifts, then I'll take you through a hard 30 minute ab workout. You will curse my name tomorrow and probably a good part of next week."

Since I was already warm, we hit the deadlifts right away and worked up to near my one-rep max. "And there go the nipples again," Elena joked as I started a heavy set.

I was used to her banter, and we made a lot of jokes as we worked out, which really helped me enjoy the sessions. The jokes got more sexual and raunchy as we became friends and she was confident I wouldn't complain to management. No matter what bra I wore, after a few minutes of intense workout, my pale skin flushed red, a shiny sheen of sweat coated my entire body, and my nipples hardened and poked through any fabric on earth.

I finished the set and dropped the barbell a little too hard. "You like what you see?"

"You mean big, fake Viking titties?" she replied.

"They're real, I swear," I assured her. The Viking joke was due to my blonde hair and height, although I was actually of Dutch descent. My parents had chosen a very popular Nordic name for me, which didn't help.

"Yes, I like." She turned and made a big show of bending to pick up a 25 pound plate. Her ass was hard and perfect, the tight spandex not hiding any curves. She looked over her shoulder at me and stayed bent over a second longer than needed and said, "You can pillage and plunder this booty any time you want."

"There you go, that's being a good trainer," I said. Elena was bisexual. I had made a crass joke about her sexuality once only to discover she did in fact like women, too. I had grown comfortable around her and enjoyed compliments when she doled them out, even though I was completely straight. I took an optimistic view of her sexual innuendos as a sign of my figure improving. We loaded more weight on the bar.

"Butt higher at the beginning, you're not cleaning," she corrected at the start of my second heavy set when I addressed the barbell on the floor. "Better. Look in the corner over there, checking you out." I looked in the mirror to my front and saw a guy at the water fountain on the other side of the gym watching me. There were few enough people in the gym for me to know for sure what he was looking at. "You're making progress. Your ass looks better every day. Why do you think I put you in these positions?"

"And to think I used to be shy. Would you tap this?" I asked playfully. The guy finally saw me looking at him through the mirror and went back to his business.

"I'd strap one on for you," she said. I loved her joke, if it even was a joke, and with a perky butt and tits nipping through my shirt, I hit a new deadlift personal record. The brutal deadlifts over, Elena began to take me through my hardest ab workout yet. My body's reaction to the sequence of exercises was about to lead to one of my most embarrassing moments.

I had noticed my libido creeping upwards as I worked on my fitness. I had discovered masturbation with actual orgasms for the first time about a month before and had turned it into almost a daily habit. I was often slightly aroused during my workouts. More and more lately when I worked my core, the exertion seemed to stimulate me in just the right places. I googled it to make sure I wasn't crazy, and apparently this was fairly common. The effect wasn't huge, at least not until today. After a few mild exercises, Elena had me do a circuit drill that included crunches and that "Captains Chair", where you grip the machine and let your legs dangle, then lift the knees high to the chest.

The Captain's Chair was new to me, and by the second set, I noticed the escalating pleasure in my loins. Elena made the problem worse by asking me to hold my knees up for a two-count before releasing. This put a lot of pressure on my insides. On the third set, it happened, and I had absolutely no warning or control over it. With my knees lifted, an orgasm hit me suddenly and caused my muscles to shake as involuntary spasms rippled through my body. "Uggh. Whew!" I said as my legs fell and the tension released. I knelt on the floor with exhausted abs to recover, giggling for a few seconds. I looked up at Elena with a tear running down my cheek.

"Oh my God. Act natural," Elena said quietly and reached down to help me up. It was a Sunday and uncrowded, so luckily nobody else was looking my way. "Did what I think just happen actually happen?"

I nodded. "It did."

"Holy shit. I've heard of that, but I've never seen it."

"Yeah, my first time as well," I said.

Unfortunately for me, it wasn't over. Elena put me into some relaxing yoga poses like she often did at the end of the workouts. On this day, a couple of the poses involved my hips higher than my head. The open, relaxed positions and my aroused state allowed gravity to pull a little more air into my pussy. When I sat on the mat and relaxed at the end, my pussy farted. She heard. Thank God she was the only one who did. Loud queefing was previously not an issue with me. I went red again. Elena failed miserably to contain her laughter. "Now that I have seen before," she said.

I was Elena's only client that day, and she had done her own workout earlier, so when I hit the showers, she was already there. There were three stalls, and I paused to peer around the shower curtain at her. I am not sure why. The seed was planted for my sexual attraction to her, but I wasn't conscious of it yet. Perhaps it was more out of curiosity. What would I look like naked at the elite level of fitness? I stared while she faced away and rinsed her face. I hoped nobody would open the door to the shower room. I was taking a chance at an awkward moment.

Elena was beautiful on a normal day. Naked and wet, she was the prettiest thing I'd seen. I took in her angelic form: the hard, taut ass, the little bit of natural side boob as she turned, and the radiant, long black hair. She turned a bit more, and my eyes took in her lovely breasts. They weren't nearly as big as mine, but they had a natural, perfect shape and looked proportionate on her frame. I gazed lower and took in her tight belly, then further down. She was completely shaved down there, and I could barely see the crack. Then I lifted my gaze, and saw that Elena was looking in the gap beside the curtain at me. I should have panicked, but I calmly smiled at her and moved on to my own stall.

What the fuck had just happened? I already adored Elena and considered her a friend, but something had just shifted. Was it lust? For the first time in my life, I was attracted to another girl. I thought I wanted to kiss her and hold her. I wasn't really sure, and that was the most frustrating thing. When I finished with my own shower, Elena was gone. I went home, resigning myself to an evening of prep for tomorrow's work day. Then I got the text from Elena.

Her: You like what you saw?

Me: I wanted to see what I am working towards.

Me: You are so beautiful. Every curve perfect. Sorry for invading privacy.

Her: Checked you out before. You look great and better each day.

Me: Body by Elena.

Her: I like what I produce. And the carpet matches. So sexy :)

That was proof she wasn't lying. I had a blonde bush. Natural blonde up top does not guarantee yellow down below, but I had it. I had pierced nipples also, but Elena hadn't noticed, or she chose not to mention it. I had done those a month ago as a reward to memorialize one of my weight loss milestones and feel cool and sexy since I wasn't getting any action.

I worried the sexual tension I felt would make it weird with her, but it didn't at all. We had a couple more training sessions and didn't discuss it. Unfortunately, for financial reasons, I had to end our sessions. She was pricey even before the gym added its fee. I managed money well and was compensated well as a manager, but it was just too much. I was also sending money home, paying back loans, and saving for a down payment.

Elena first asked if her sex jokes and bi status were the real reason. I reassured her that I loved her personality while we worked out. So Elena was cool about it. She encouraged me to drop the gym completely and take up Crossfit. It was more expensive than Golds, but way cheaper than personal training. She confessed to me she was a member already, and there and in her kitchen were where she really built her body. I was sold, and we ended up training together at the lunch class a few times a week. The program was great, and I continued to see results on the scale and in the mirror. The camaraderie in Crossfit was fantastic also, and I made more friends and developed a social life.

Elena and I started eating lunch together after every workout, then even hanging out at night at my place to watch a movie on weekends if she didn't have a date. Over the next few months, she became my best friend as the weight continued to come off. I really got to know her, and was flattered someone so popular and beautiful would choose to be so close to me. She was very promiscuous and had no hangups whatsoever about taking on new lovers of any gender, and I kind of envied her adventures. I felt like a child around her, and never spoke much about my boring dating history. I came from a small town with a somewhat religious upbringing. I loved everything about her, and it was hard to deny that each day I became more attracted to her. I knew for sure when I began to get jealous of the men and women that enjoyed her as a lover.

Even though Elena was into women, she didn't come on to me. She respected that boundary with me as a "straight" woman, and she probably didn't want to risk our friendship. I was confident that my friend thought I was beautiful, but she had men and women lining up. I filled a void with her as a close friend, and that's just what I needed too. She left the door open, though. "If you ever want to share a kiss and see where it leads, go for it," she said.

I respected her so much. She had a day job in marketing, using an MBA she got while working full time. She was a trainer as a second job for fun and extra cash when time allowed. She competed as an amateur in various fitness and bodybuilding competitions. Somehow after all that she had time to have a delightfully promiscuous and diverse dating life as well as spend a lot of quality time with me.

Then tragedy struck. Elena's father died suddenly. Her father was her world, and I knew this would be devastating. She was gone for three weeks to New York. We used Apple's video call "face-time" service with our iPhones almost every day she was gone. She returned on a Saturday, so I just assumed her first priority would be to hang out with me, but I was wrong. My texts and calls went ignored, and I began to worry. Finally at about 7:00 she texted and asked if I wanted to come over about 9:00.

What I didn't know was that Elena needed a good fuck. Usually that meant a man, but on this night it was a woman. I was in such a rush to see her, and we were close enough friends where I could come unannounced anyway, that I was in the parking lot of her apartment complex about 20 minutes early. As I headed to the stairs to go to her third floor apartment, that other female trainer from the gym was coming down, decked out in her finest gym clothes.

I tried to recall her name. Katya I think it was. Not Katya the Instagram yoga pants girl. I wondered if our Katya made up the name. She seemed so fake: everything from her personality to her long eyelashes and the big set of fake tits that weren't bouncing very well as she descended the stairs and gave me a condescending look. Hard nipples poked through her shirt, just a little too high on the breasts to look right. I had trained with her once before switching to Elena, and she definitely recognized me. What the fuck was this bitch doing there? I was ashamed, knowing my petty jealousy was hitting an all-time high.

I knocked. Elena opened the door. "I'm sorry, I'm early..." I said. She launched herself into a hug and obviously didn't care. I told her how sorry I was, and she sobbed for a minute before letting me in.

We settled onto her couch. Elena was in a bathrobe with messed up hair. I knew she probably just had sex with Katya, but I didn't bring it up. We talked about her father for half an hour over two glasses of wine. I found out she was adopted as a teenager, which was actually huge news. It was odd that I was just finding out, but I didn't probe further.

"Nip slip," I said with a grin, interrupting her as we neared the end of the serious talk. Her robe had parted, and her left nipple was showing through nicely. It had been for ten minutes, but I was enjoying her "accidental" tease.

"Sorry," she said and covered up.

I sensed Elena wanted to talk about something else. She had grieved enough for now. I went on the offensive. She would know I was doing it out of love. "So," I began. "I saw that other trainer leaving, after I couldn't get in touch with you. I think I might be jealous," I confessed. "Why was she here? I'm still your BFF right?"

"I had physical needs that had to be met. You, unfortunately, aren't sexually attracted to me."

"Whatever. Did you..." I was embarrassed to ask, but I definitely wanted to talk about it. "Did you have sex with her?"

"Of course. Jealous?" She was smiling now.

I felt weird. Elena got laid all the time. Why had my jealousy suddenly transformed to extreme annoyance? "Maybe," I confessed. "Never before. But today, yes."

"You don't like women like this, Brit, so maybe you just don't like me hanging out with her before calling you."

I shook my head no. "I'm jealous that you fucked her before calling me, even if we don't have sex." She and I were different people when it was just the two of us. F-bombs were frequent and encouraged forms of communication. "You should be trying to have sex with me before calling her."

"That makes no sense," she joked back. "You don't like women that way."

"True. But, you're not just any woman," I said. There was no going back now. Elena would get the hint. We just didn't take joking this far, ever.

She stood and faced me, then untied her robe and parted it. She wasn't wearing panties either, so I was treated to a full frontal. "Look at me, everywhere," she commanded. "It's nothing you haven't seen before."

I obeyed, and my body responded to her immediately. My pussy tingled as I gazed at her form, and I began to swell and lubricate down there. Despite her disheveled hair and lack of makeup, Elena was a total stunner. She had cut more weight as her next show was getting close. Her body fat was low, but she still looked deliciously feminine. She was hard as a rock where it counted, but soft and curvy too with perfect, healthy skin. She didn't have any ink other than a small set of numbers and a tiny design on her forearm, which was a little bizarre for someone that did the stuff she did, but I liked that on her. It kept the focus on her natural beauty.

My gaze lowered, and her pussy was completely bare as it was the last time I had stolen a glance at it. I looked closer. She had her legs about shoulder width apart, so I could see more detail. Unlike me, she didn't have large lips. Her outer labia fully enveloped her treasures, giving her a tiny slit down the middle and not much else to show. I liked the contrast with my own body.

"What do you think?" she asked.

I was honest. "I think you're the most beautiful creature I've seen, inside and out. You're perfect to me."

She took a step forward, within arms reach almost. "None of that matters if I don't appeal to you. Do I turn you on? Tell me the truth."

I took my time answering, looking her over again first. "Yes. Only you. No other woman, ever."

"There are a thousand shades of gray in a woman's sexuality between gay and straight. I'm happy you aren't all on one side."




The Holiday Party



"I agree," I said, my eyes lifting to meet hers now after memorizing the appearance of her pussy and burning it into my memory forever. "How about me? Do I appeal to you?"

"Of course. Can't you tell? I mean, it's not a condition of our friendship that you indulge that part of me." I just smiled softly, not really knowing what to say, so she continued. "You were always pretty, you know. But I don't think you realize how beautiful you've become through the hard work. And I'm comfortable around you. Being close friends makes it hotter for me, not weirder. I adore you. I'd cherish you. Love you. I would fuck you, Brit," she added, slowing to emphasize that last point. 

"You don't make this easy for me, do you?"I said. Fighting my arousal was futile.

"That's quite a secret you've held on to. But I've noticed changes in how you look at me over the past month," she said. "I also don't think you will ever really want to be in some kind of a long-term relationship with a woman, nor would I really. Maybe we can fool around a bit and not risk our friendship." Now she smiled big and took another step forward, definitely invading my personal space as I sat on the couch. She reached her hand out, so I gave her mine. She pulled it to her right breast. I cupped it and squeezed gently, not really sure what she wanted me to do with it. "First time touching a woman like this?"

"You know it is," I said. Elena filled my hand nicely with little to spare. She had darker complexion than me, but she still was fairer than most Latinas. Her nipples were dark brown and erect as my finger brushed one of them. Her breasts were firm and natural, a welcome break from the fake jugs I saw on so many women in the gym, but it was also good to have more than an A-cup that I might encounter on someone so petite and fit. I reached up and touched both breasts.

"And now touch me here," she said, lowering my hand towards her crotch.

"Oh wow," I said as she moved my hand. When my finger touched the top of her crack, I panicked a little and pulled back.

"Too fast?" she joked.

"It's a bit overwhelming," I confessed. "So, when you and Katya, you know, how did you..." I wasn't sure how to ask, but I was very curious. "Was there penetration, who did who?" I laughed. "Can I ask this? It's not that I want to do it, I am just curious."

Elena chuckled at my innocence. "You want to do it, or you wouldn't ask, but I'll let that slide for now. Yes, there was definitely penetration."

"Show me. What did you use?"

Now it was Elena's turn to be a little embarrassed. "Really? Okay, if you say so." She disappeared for a minute, then came back with a blue dildo and what looked like a small bottle of lube. But it wasn't a normal dildo, it was in an "L" shape with two ends, which I'd never seen before. "I cleaned it off after, just so you know, so don't get squeamish." She took the smaller end with the bulb into her mouth to wet it, then brought it to her pussy. Her crack opened to the pressure, and the dildo slid into place. The long end stuck up on its own and looked just like a very blue erect penis of average size

"I'll be damned," I said. "You don't have to use straps or anything?"

She shook her head no. "It takes some getting used to and some conditioning, but I can hold it in good. The end in me feels great, too. Don't ever tell her I said this, okay, it's private. Katya likes me to power-fuck her hard, and it's fun to dominate such a strong girl. I love it. It's what I needed after that emotional roller coaster in New York." I wasn't sure what else to ask, so she continued. "I've fucked more men with this than women to be honest."

"Huh?"

"They love it, almost all of them. It's so easy to persuade them, and so much fun to turn the tables. With women it's more about licking and kissing. Well, at least with me." Elena sat on the couch next to me, then grinned. "So, we're playing show and tell, right? It's your turn. I want to see your boobs."

"I'm afraid not," I said. "Two glasses of wine aren't enough, sorry. I'm keeping my virtue today."

"But I'm so forlorn. Give me a pick-me-up," she teased, her hand reaching over and brushing the hair off my shoulder, then lingering there. I really wanted to indulge her. Seeing her beautiful body on the couch with the dildo sticking up from between her bare legs was a gigantic turn on for me. It was impossible not to think about how that dildo would feel in my pussy.

I was wearing a casual dress that came up just above the knees and wasn't too tight. Up top I had a little cleavage showing, but the the dress was still suitable for a work day. My shoes were off, and I didn't have any stockings. It was warm for November. "Elena, I'll take you up on your offer now," I said. I think she knew what I meant, but I got the blank stare anyway. "May I kiss you?"

"Yes," she replied.

I wasn't nervous at all, which made no sense. I was always nervous kissing a guy for the first time. Instead of just leaning over for it, I stood and straddled her on the couch, leaving that dildo concealed by my dress in front of me. I was surprised at how comfortable the position was as I smiled softly and brushed some hair out of her face before leaning down to meet her lips. I'd pecked her lips before while saying goodbye or whatever, but we'd never kissed deeply. Now she seemed so welcoming, so naughty and tempting. I sniffed down by her neck first. "New scent?" I asked. She nodded. Elena always wore the same perfume until now. This new one was better, but still subtle.

I was in control on top, so I started with a normal kiss, our lips pressed together for half a second longer than a peck. I enjoyed the squishy sounds of our lips as I gave her two more. I held the next one for a few seconds, enjoying her soft lips. She opened her mouth slightly to encourage me, her fresh breath on my face as she invited me to deepen the kiss. I teased her upper lip with my tongue, then slid it inside her mouth as I pressed against her.

Elena massaged my tongue with hers before probing into mine to explore. Everything began to blur together after that. I couldn't do much with my hands in this position, but Elena was free to work. She rubbed my back gently and played in my hair as we just enjoyed the kissing. This lasted for a very long time. I certainly never kissed a guy anywhere near this long, and we weren't close to being done. My pussy continued its response, my damp panties leaving no doubt as to how I felt about my first real kiss with a girl.

Elena's hands gradually found their way down to my butt. She massaged the buttocks gently at first, then began pulling me into her more and more. I became aware of that dildo sticking out of her pussy in front of me. She scooted down on the couch and pulled me harder until my pussy was rubbing against it as she gyrated her hips and tugged at my butt, giving me a very pleasurable dry hump. It felt great, so I didn't stop her.

They say you do your best thinking when you let your mind go free, like in the shower, or perhaps when making out with a girl for the first time. I don't know why, but my busy brain suddenly connected some dots regarding Elena's background. The revelation was so upsetting I had to stop and address it immediately. I backed out of the kiss and just stared at her with an open mouth for a second.

"What?" she asked, knowing something was wrong.

I pulled Elena's right hand from my back to my mouth and kissed it, then slid my hand down until it stopped at the tattoo on her forearm. Our office worked closely with a non-profit that dealt with this stuff before. "I don't know why I never noticed before, but it just hit me. Elena, I know what this is." She seemed surprised. I waited a few more seconds, and I noticed the tear welling up in her right eye. "Tell me," I said.

She shook her head, and the first tear slid down her face. I didn't want there to be more, but I had to know the truth. "I never talk about that with anyone," she said.

"I love you. If not me, who can you tell? You're my best friend," I said. She nodded. But she just evaded my gaze, stalling. "Come on."

"It's going to kill what's going on here between us today. This is heavy stuff if you want in."

"I want in your world," I said.

After a long pause, she began. "I was 11 when my family sold me. I was already being raped and abused anyway at home. I was 13 when my real father found me on the streets in France and ended up getting me out and adopting me."

"Holy shit," I said. Elena's tattoo was forced on her and marked her as someone's property. It was sickening. She was the victim of human sexual trafficking at an age when I was still watching cartoons. "Elena, are you okay now? I don't really know how to ask the question right."

She smiled. "Yes, I'm fine. It's amazing how much difference great parents make, I just found mine later in life. I have a clean bill of health, mentally too, I think," she added with a nervous chuckle. "I'm not crazy, and I don't have any STDs. I was never addicted to drugs, which really helped."

I already noticed the apparently fake Spanish accent was fading while she told me this. The next question was easy. "Where are you really from?"

"Born in Slovakia, then Ukraine before taken west against my will," she said. "I use the name I was born with, it just used to start with an 'A', which is a more European version." Her accent was evolving now for sure into what was presumably eastern European. Then she said a few sentences in a foreign language.

"What was that?" I asked.

"That was Slovak, my dear. I said you have beautiful eyes with love in them, and I want to tell you my darkest secrets. If you prefer Russian, I can give you that, too."

"Or flawless Spanish. Now you're just showing off," I teased. "It all makes sense. I can see your genetic Slavic features now that I know to look. I can't believe you duped me with the Panamanian thing. That was smart picking a smaller country instead of, like, Mexico." She nodded. "Why do you keep the marks if you went to the trouble of inventing a new back-story?"

She looked at her arm. "I hate it and am proud of it at the same time. I'm a survivor. It keeps me humble. I can't really say for sure. Don't you have any dark secrets?"

"I did give a blow job when I was 12," I said. "I am pretty sure he was over eighteen, and it was not cool of him."

"How did that go? Did you take his load?" she asked. The mood was lightening again with the focus back on me.

"Yes, actually, with no spillage and very positive customer feedback. It wasn't that bad. It's funny because it was another five or so years before my first kiss." This was a true story, except that if I was being totally honest, I had put the guy up to it. I was curious.

I leaned in again and gave her two of the softest kisses I could manage, then I attacked her. I was aggressive with my tongue while my head moved side to side to get at her from different angles. I drove my hips forward into her, smashing that dildo between her belly and my pussy as I dry humped her. The other end of the dildo moved around inside her pussy, making it hotter for her too I hoped. There was an urgency and intensity in my kissing that wasn't there before. I felt so lucky to have her here with me. How many obstacles had she overcome in life to bring her to this point?

I pulled back after a few minutes. I was breathing hard, and my brow was wet with sweat. "I'm horrible," I confessed. "It's such a tragic story, but I am so hot for you now I can't stand it. It's like I'm in a sexy spy movie. Plus you confiding in me and trusting me makes me feel so close to you," I said.

"I don't mind. I love your reaction. The only thing I'm upset about is that you're wearing panties," she teased.

I took the hint, standing to pull off my panties under the dress. "I'm leaving the dress on. I'm shy," I said. I straddled her again, and it was a whole new game. I felt my bush against her legs. I was quite wet, and I knew Elena could feel the dampness. The fabric of the dress was loose and would allow easy copulation if desired, but it concealed my genitals from her view. It was a little unfair, since Elena was completely naked with a dildo sticking out of her. We kissed some more, and now that dildo was bumping against my clit directly as I moved my hips around. After a few minutes of that, an orgasm wasn't far away.

"Put it in," she said, breaking off the kiss. "I know you want me; I can feel how wet you are."

I paused for a moment, long enough for her to suspect something was holding me back. "I do for sure, but that's a pretty big step." I lifted my hips a little bit higher and forward, then reached under my dress from behind to find the head of the dildo. I thought it would be an awkward position for actual sex, but the dildo lined up with my pussy remarkably well. The tip struck just below the pursed end then settled into the opening. "I don't know..."

"Can I watch it go in? I'm very visually turned on like a dude."

"I suppose that's fair," I laughed, her enthusiasm contagious. I slid the tip up my lips to the clit for safer storage while I pondered this. Elena lifted the hem of the dress and looked at my bare pussy. "Wow, you're so beautiful down there, Brit."

"I don't know about all that. I feel so unfashionable with this bush next to you," I confessed.

"No way. I love the blonde hair and those big lips." She moved beneath me, causing the dildo to slide back down my crack in preparation for entry.

But I paused, and after a second she finally looked back up into my eyes. "Elena," I started. "You have your secret, and I have one, too. Except mine is small, incredibly silly, and I feel a bit foolish." I could tell she had no idea. "I'm still a virgin."

A couple seconds went by with her just staring, then a small laugh, then a bigger one and a smile. "Oh my God, are you serious?" I moved back a bit and squatted behind the dildo like I was before. "That guy you dated for a few months?" I shook my head no. "Gave a BJ when you were 12, but still a virgin at 23?" I nodded yes. "Have you played around before by yourself with one of these toys, or are you actually going to have to pop something here?"

"I'm pretty sure there will be some popping, yes."

"Well it's time it came off. You're the only virgin I've heard of with pierced nipples. Hence my surprise. You've been pretty crafty with your word choice to avoid my suspicion before, by the way."

"I've been as deceitful as possible without outright lying," I confessed. "The nipple rings are recent. My reward for the first 35 pounds you helped me shed."

"You'll need some lube," she said. The bottle was on the table next to the couch. She lifted my dress again and smeared the gel all over the shaft. "This is the perfect toy for you. It's smallish and goes in smooth. Take your time. Slide down and take it at your own pace." I doubt it even occurred to Elena that I might not be ready to lose my virginity.

I looked at her lovely face. I really didn't think I should go through with this, but I had never wanted to have sex more. I was working it out in my mind how to explain. She waited patiently. "I'm very horny for you," I began, "but do you think we can save this last part for later? I mean, I'm sharing the night with that girl from the gym." I wanted to say "skank," but that wasn't fair since the skank and I wanted the same thing. "I'm even sharing the penis with her on the same day, and we haven't had time to really explore each others bodies yet. I feel like the consolation prize."

"You're not. Nobody means to me what you do. You're right about exploring though," she said, reaching up to cup my breasts outside my dress. "But I still think we should fuck."

I looked into her eyes and saw so much love there. But there was lust too, for me, and sadness for her loss. She deserved to have me if that was what she wanted. And if I could do this for her and make her day bright after what she'd been through, I owed her that. I knew I would enjoy it anyway. "Put your hands here, on my waist," I said.

Elena gripped my hips. "Nice hip to waist ratio. You have such a wonderful hourglass figure now."

"My trainer is awesome," I said. I lifted my hips again and reached under to guide the dildo, now slippery with lube. "I love you, and I trust you completely. I just think this night is wrong, and I think we should wait. But if you want this now, I'm yours." I made a slight adjustment. "There. It's at the hole. Pull me down, lift your hips, take me if you want. It should slip right in there even though it's my first time. Trust me, my body is ready."

My complete submission put her in charge, and I had no idea what she would do. She looked into my eyes for a while and pondered it, then she lifted the dress again to look while she reached in to grab the dildo. She pulled it forward just enough to rest it on my pubic bone. "Stay like that," she said. Her hand reached between my legs, and she gently eased a finger into my pussy. One finger was easy for me; I did this while masturbating sometimes. Her finger was smaller, and lubed. I moaned and smiled. "Very tight," she said. I nodded, then Elena pulled out and moved her finger slightly to the rear and rubbed my anus.

My dreamy eyes opened completely. "Oh hell no, I don't think so," I said.

"Oh hell yes we are. Half of your virginity is safe, but your virtue is still mine."

"No. No way. Seriously?" I'd never even considered anal before. I'd never put anything in my butt. No guy had put anything in my butt. I'd never felt a desire to have someone fuck my butt. But Elena's finger was gone, and now the dildo pressed against my butthole. I knew I couldn't deny her. I had to do something after playing the reluctant virgin card, and I had zero emotional attachment to my anal virginity, if such a thing existed.

"Push out while it goes in. Take it easy. You can do it. This dildo is on the small side. It's more about relaxation than you having to stretch to take it," she coached.

I reached around to help hold the dildo and guide it. Her aim was off slightly to the front, making it at risk to go into my pussy. I settled my weight on the pole, and it just pushed my anus around and didn't go in. I tried a couple more times, and the tip finally began to open me. But the alignment with my body wasn't as good in this position as a vaginal entry would have been. "Do you think I can squat on it?" I asked. Instead of being on my knees straddling her, I went to my feet and tried to squat. I had to grip the back of the couch for support, but it was actually fairly comfortable.

"Sit on it, gorgeous." She took control of the dildo and held it steady.

She found my pussylips again as I lowered. "Wrong hole," I teased as she fixed her aim.

Now it was easier for sure. The penis was aligned perfectly, and all I had to do was let go of some body weight I was holding back. Once I relaxed enough, the dildo surprised me when it suddenly entered. A sharp pain, and then I slid down rapidly until my ass had engulfed my entire half of her strapless dildo. "It's in. Ugggh. Fuck, that hurts," I whined.

"Good job, all the way down on the first try," she said. "Don't pull it out, get used to it now."

"Once the head was in, the rest was easy," I said. I rested my butt on her thighs to try to get used to the fullness before moving. The pain was localized near the front where the tight muscles guarded the entrance. They were protesting the unnatural act with involuntary, painful spasms. "God I hate you right now. You are such a bitch." I joked.

"I know, I am. Totally worth it," she replied. I breathed and focused on relaxing, and gradually the pain went away, for the most part. "Ride my cock, baby. Let's see what you got. Don't let it out all the way yet or it kind of stings going back in." 




The Holiday Party



I lifted up, and I admit it was cool to feel that toy sliding out of my ass. I stopped at about the right time. I had a tight squeeze going on with my nether regions, and I could feel the contours of the head. I lowered myself slowly, then repeated over and over. I can't say I liked my first anal. We didn't really connect emotionally, because I was too distracted by the pain during an act that didn't feel natural to me yet. I was not used to remaining dilated at the entrance like this, and it just felt like I had to go to the bathroom the entire time. I was still happy to do it for my friend that I loved. I started moving my hips around, not just up and down. I wanted to cause the smaller bulb end of the dildo to move around more in Elena's pussy and hopefully make her feel good. It worked, and she let me know.

"Are you going to come?" she asked "Is it working at all?"

"No, I don't think so. I can get myself off, but this is just too intense with the anal. You?"

"Not sitting. If I am on top or standing I can even when I am doing the fucking."

"Have you fucked me enough yet? Did you officially take my anal virginity now?" My ass still hurt, and my squat muscles were tiring.

"Yes," she laughed.

I lifted up, and the dildo plopped out of my butt with a tiny burst of pain. I pushed the dildo back with my butt and sat in front of it and leaned in to kiss her.

"Ooh, nice," she said as the dildo probably rubbed her G-spot while I pushed my end of the shaft down.

"To be continued..." I said.

"I hope so," she replied.

I felt we needed a break or even that this was a natural ending to our night. I stood and was horrified by what I saw. There was no mistaking the little bit of brown lube on the shaft. "Eww," I said and tried to wipe it up with the only thing I had, my dress, before she saw it.

"A little of that is normal, it's anal after all," she said.

"I'm so embarrassed," I muttered, my red-cheeked face looking down. I suddenly felt stupid. I was a naive virgin and had no business doing anal. I was annoyed with her for talking me into it. And what kind of stupid girl does anal anyway and refuses normal sex? I would mock someone for this. I put on my shoes and got ready to go.

"You can stay. Come on, silly."

"Sorry, this whole night is just weird. I have to go. I love you, and again sorry about your dad," I said and hugged her, leaving her standing in her apartment den naked with the dildo hanging out of her as I stormed out. I could not stop squirming in my car seat the whole way home thanks to my anal deflowering. I had that ache you get from pushing things just a bit too far, and every way I adjusted my posture still put pressure on sore flesh and muscles inside my ass.

I was so embarrassed, I went about five days without calling Elena. After some reflection, I realized that I had flaked out and overreacted. But after five days, it became harder to call, so another week went by. Then I was annoyed she wasn't reaching out. It was all so silly, and throughout our friendship, this was the only time we weren't close. I went on a couple dates with guys I had met on an online dating site to distract me, but it didn't help. I had been on a lot of first dates since I had put up a profile a few months ago as the weight came off. I began to feel depressed that I might have lost a best friend. I poured myself into my work, and two more weeks went by. I didn't see her at Crossfit either. I switched times on most days, and when I did go at our usual lunch time, she wasn't there. I assumed the worse case scenario of her avoiding me.

On a Thursday I got some fantastic news. I'd been working very hard in my first job since college. The company wanted to promote me, but it would mean a move to the other office a three hour drive away immediately after the new year. I accepted, but I was sad knowing I would be leaving my best friend, especially on bad terms. This was the big break I was waiting for, so I broke my lease and planned on moving that weekend. I would start in the other office as soon as possible the following week.

The news of my promotion triggered a chain reaction of events that ended my virginity that weekend. The news finally brought me out of my funk and elevated my mood. I was riding a wave of confidence and happy emotions going into the wildest weekend of my life sexually and didn't know it.

It started early Friday morning when I stood on the scale before my shower. I had done it. After months of dieting and hard work, I was at my ideal weight, or rather, a pound under. I arrived at work by 7:00 in the morning and settled into my cubicle like always. I was usually one of the first people at the office and could get a lot done in that first hour before others began to bug me. On Friday it was even more obvious, since people generally dragged in later than normal. We had an open landscape design, so I had a cubicle even as a manager. The only difference was mine was in the back of the row near the window, and it was a little bigger with taller walls for more privacy.

I couldn't stop thinking about sex. A lot was going on to make this a peak hormonal time for me. It was the right time in my cycle. I had an abundance of endorphins from the promotion and move. I was slimmer and felt sexier than ever before. I pushed my chair in closer to my desk to hide everything below my waist. I had a knee-high dress with full nylons on. I began just lightly rubbing my thighs together as I tried to work on email, but really I kept thinking about Elena. Then I'd think about dick, then Elena again. I hiked up the dress and rubbed my pussy on top of the nylons. It felt so good. It was so exciting to do this at work, knowing at any time a coworker could drop in. If I was lucky, I'd hear anyone with a few seconds of warning. I stared at the monitor and put one hand on the mouse to improve the charade.

I stayed on top of the pantyhose until I was ready to climax. I was still on a daily masturbation routine and was getting better at it. With each session, I could make my body respond faster to my touch. I reached orgasm quickly, and I think the public aspect of the lewd act helped. When I was close, and at the last possible second, I reached under the nylons and my panties and ran my fingers through my thick bush. I found the little nub and hit it at just the tight time, sending me into an early morning bliss and wetting the fabric for the next few hours. I exhaled deeply but managed to suppress any noticeable moans. It was a great early start to the weekend.

I was able to concentrate and get some work done after a good orgasm and two cups of coffee. By 5:15 in the afternoon, I needed a different kind of release since I had to work through my usual lunch workout. I hit the 5:30 Crossfit class. The cool shower afterward felt great, but I had to put the same work clothes back on and return to clean out my work space to move to the other office. I decided to go commando under my dress. I hated pantyhose, and the panties had been on all day and just seemed gross. This was a rarity for me, and I was definitely uncomfortable with the idea.

It was 7:00 by the time I returned, and the entire floor's cubicle farm was vacant with the main lights dimmed to save energy. We had dedicated employees, but on a Friday nobody stayed late. If they had to work, they would log on from home. I packed in five minutes with one small box. I had almost no possessions at work. As I was about to leave, I heard keyboard strokes one aisle over. "Aren't you going to say goodbye?" he said over the cubicle wall.

Jeremiah was in accounting. He wasn't the manager, but we all knew he held down the department. He was working late closing the month end, which he had to be in the office to do, given our archaic ledger software. I rarely had to work on projects with him, but when I did, I was thoroughly impressed with his professionalism and skill. I was a bit of an overachiever also, and often we were the last people to leave at night. The problem was he hit on me and asked me out a while back. I declined, office politics making me refuse to date at work. But the whole truth went to a darker place, which I had pushed aside amid more convenient excuses. Once I became a manager, I distanced myself more. I felt kind of bad. He respected me and never asked again, but part of me wished he had tried a little harder.

I went to the other aisle as requested. He was well-dressed as always and greeted me with a warm smile. He was a very fit and handsome black man about two years older than me. He was also tall; one of the only men on the floor more than an inch or so taller than my 6'1" frame. "Being a martyr again?" I said.

"Congrats, I heard. You deserve the promotion, but we'll miss you here." His eyes drifted down to check out every inch of my body as he talked.

Maybe because I was leaving for good, I felt like flirting. When his eyes drifted back up but stopped halfway up, I countered with, "You mean you'll miss me. Look up here, not at my tits. There, that's better." I was opening the can of worms for whatever stupid reason. My cocky grin was out of character for sure.

Jeremiah took the bait and got right to the point. "How come we never went out? I can ask now with you leaving and all. You know I think highly of you, always have."

"And I you. But we work together."

"No, that's not it. You went out with John from wherever."

"Marketing," I said. "Two floors down, totally different department, come on. Not the same thing." This inquiry would normally be annoying, but it felt more like flirting. I was having fun. "And that was a one-time mistake, by the way. Huge Napoleon complex."

"It's about race, isn't it?"

Dead silence for a few long seconds. I looked around to check that we were still alone. I was annoyed. Being from the rural Midwest, this whole race card thing was a foreign concept to us. I'm not sure what came over me next. At work I was an alpha girl for sure, aggressively pursuing career advancement. But not with men. I was inexperienced. Normally I would just confidently walk away. I wasn't feeling particularly sexy either. My dress wasn't one of my best outfits, and I was in flats. I didn't wash my hair in the shower after the gym, so my hair had drying sweat in a ponytail. I had little makeup on and wasn't wearing panties. But I had hit my target weight that morning, and I felt like my body was sexy, and that mattered the most. I moved into his cube and got between him and his keyboard. I pushed it out of the way and leaned back slightly, my butt against the side of the desk. I put my hand on his chest and pushed him in his wheeled office chair back to give me room. I folded my arms on my chest and just glared at him.

"You're not going to turn into a whiny bitch now are you?" I said. "I didn't think you had that chip on your shoulder." He looked surprised. I smiled to ease the tension a bit, and he looked away, a little embarrassed. I found the lever on the side of his chair with my foot, and he went crashing down to the lowest setting, putting me in a better position to look down on him. He didn't say anything, and I realized he was waiting for an answer. "You liked me, even when I was fat." He nodded. "You could have any woman you want, hell you probably have many women you're stringing along right now. Why me?"

"I do okay," he said. "You're different than most women. I don't know exactly why. You've always stood out in my mind."

"What do you think of me now? Too skinny for you?"

He finally laughed again. He picked up his phone and acted like he was looking at it. "Girl, your ass is like avocado. It's the good kind of fat."

"Yeah, my Instagram feed has the same memes as yours." I paused, then looked serious. "You're right. A little. Mostly it's the dating at work holding me back though."

"Huh?"

"The race. It matters. I admit I'm not perfect. I have my reasons, and it wouldn't be exactly as you expect."

"Ah, honesty," he said.

I think this would end our conversation if it wasn't for the obvious fact that I was into him at that moment. I went back to the aggressive persona, but it was clear now I was at least partially faking it. "That doesn't excuse you from being a bitch about it though. A girl doesn't owe a guy an explanation for rejection."

"Fair enough," he said. "Seriously, you're super cool. I've always had a thing for you. I just couldn't ask more than the one time. I had to respect your answer."

My heart melted a little. I didn't get this kind of attention often, and Jeremiah wasn't desperate for female attention. I looked him in the eye confidently as I slowly lifted the hem of my dress up to expose more thigh. He took the hint and looked at my leg. It was a knee-high dress with loose fabric, so what I hand in mind was feasible. "Go down on me right now, or never speak to me again. Don't stop until you're finished," I said. "Debunk the stereotype. Service me and send me off right after that remark."

"Here in the office?"

"I'll let you know if I see anyone coming down the hall. I just showered at the gym, so it's nice and fresh for you." I grabbed his chair and pulled him close. The tall stud wouldn't have to bend far to reach me. He gripped my thighs, then lifted my dress to expose my pussy. I took the fabric from him so he could work.

"Celebrating your promotion with a little racist innuendo and sexual harassment, I like it," he said as he brought his head to my bush.

I was out of character for sure being a little dominant, so I was relieved when Jeremiah went for it. I'd been on the receiving end of oral sex lots of times even though I was technically still a virgin. Half a virgin, I corrected myself with some amusement. I dated a guy for a few months that had some skills, and it happened also with a few other guys I wasn't as serious with.

He kissed me first on the inner thigh, spreading shivers throughout my body as he peppered the surrounding area with his wet lips. Occasionally his shaved head rubbed against my belly or vulva and added to my pleasure, so by the time his lips and tongue touched my privates, I was truly aching for him. Finally, he gratified me with a tongue flick against my protruding clit, followed by many other light strokes before opening my petals with a downward exploration of my crack.

This wasn't the easiest position for oral, but it worked great for me at least. He had to focus on my clit, because the standing position with my legs close together with him in front of me made the hole harder to reach. It was a huge turn on to stand over this powerful man and have him do exactly what I had demanded, putting my needs first with no hint of reciprocation. We were alone in a sea of cubicles, but knowing someone could interrupt us also made the experience hotter.

He looked up and smiled as his tongue was buried between my crack. His strong hands caressed my thighs, then reached around and grabbed my ass cheeks, pulling me slightly away from the desk I was leaning against. "Come for me, Brit."

"Won't be long. You're pretty good at this," I said. I was building toward a climax quickly. It was hard to pinpoint why he was better than other men that had eaten me out, but every touch seemed to have a purpose, and he hit just the right spots with the right amount of pressure. He never stayed in one spot, covering all the parts of my vulva even while the focus was on my clit. He teased the entrance to my hole as best he could in that position, and he even slid in a little. I wondered if he could tell I was still a virgin, but he didn't say anything.

As orgasm approached, I pinched and rubbed my right nipple as best I could through the fabric of my bra and dress. The closer I was to orgasm, the stronger I liked the pressure on my nipples. When I masturbated, one hand usually attended a breast while the other rubbed my clit. Near the end, I didn't mind a slight bit of pain. It actually made the experience better for me as long as I waited long enough.

He knew when the timing was right, and he zeroed in on my clit, hitting it at all angles, even sucking the whole clitoral hood into his mouth. The assault on my button was harder than the light strokes in the beginning, and only now near the end could I have handled this. He was good at reading me. I pulled his head into me hard when the moment arrived. I struggled to contain my voice in public as I grunted softly when the waves of energy rocked me.

He looked up at me affectionately and patted my butt. I could see the evidence of my high arousal all over his face. "How was that for you, love?" he said.

"That was a good one." I pushed his head back and started to walk off. "Maybe I'll see you at the party tomorrow, if not, then that's okay." Fake-dominant Brit was back.

"Wait, was it really all about you?" He stood. "I won't be there tomorrow, so a hug goodbye at least?"

"You were my going away present," I said. I leaned in for the hug, but I also reached down and grabbed his crotch through the pants. Something rather large was waiting for me. "Damn, okay. Well, show me what you got." I leaned against the desk again, hinting that I might stay.

"Sure." Jeremiah seemed very eager as his fly came down. A giant slab of black cock spilled out for my viewing pleasure.

I stared. I couldn't help it. "Good lord."

"I can't debunk that stereotype, sorry."

"That's the biggest dick I've seen," I said. I'd only seen five before in real life (yes I kept track), but I was sure I could scour the earth and be hard-pressed to find his equal. Jeremiah's offering tapped into something primal in my mind. I realized I was still a virgin only partially because of my convictions. The other half was never being tempted like this. I had an overwhelming need to feel him inside me. I lifted my butt and perched myself on the very edge of the desk. "Come a little closer," I said, reaching out to grip his member as he approached. His swelling unit was flaccid still, but he was already wider and longer than any man I'd seen. His cock felt heavy and powerful in my hands. He was uncircumcised, which seemed odd at first, but I got over that in about two seconds and liked the natural look. I retracted the foreskin to reveal the shiny, giant head that was a few shades of brown lighter than his shaft. I wanted him. I didn't plan on losing my virginity to a man I'd never gone out with and likely wouldn't ever go out with, but my mind was made up. He didn't need to know that yet, though. "Yeah, you're not coming near me with this monster," I said. "It's going to get even bigger."

"You can handle it, girl, we just have to work it in. Spread that big pussy for me."

I laughed, thinking yeah, on the outside. I'm a tiny, timid girl inside. He didn't seem surprised I had said it, and I had a feeling I wasn't the first woman to balk when she saw his big dick. But I was also salivating. I always enjoyed a good challenge.

Jeremiah moved between my legs. He was six inches from glory now. All I had to do was lift my dress again and give him the green light. "I'm not on the pill, and let me guess, no condom either?" I asked. He shook his head no. I pushed my hand under his cock through his fly. I cupped his balls gently. The skin was smooth and hairless, and they were huge. This man seemed so potent.

"I'll pull out in time, no worries. Let's fuck, baby."

I laughed, happy to hear his enthusiasm. "I don't want to get pregnant," I said. I miked his cock, this time from closer to the base until my hand was out of his pants. "See," I said. A drop of fluid oozed out onto my finger. Despite not being hard yet, he was already leaking. "Your pre-cum is white already. You have a loaded gun." Enjoying pretending to be much more experienced than I was, I brought my thumb to my mouth and made a big show of licking the semen. There was enough to get that taste for sure: the strong taste and scent of sperm, not regular pre-ejaculate. I lifted my legs and used them to pull his hips closer to me.




The Holiday Party



"You are a leggy girl; I love it," he teased as my tall frame enveloped him.

This angled my pussy up more, in perfect position now to receive him. A flood of adrenaline hit me. I was really doing this! I still controlled his cock, and I brought the head to my pussy as he moved close and gripped my waist. He had left my large lips stuck together in the "taco effect," so I could see them easily sticking out of my full bush. I rubbed the head against my clit, then ran it down my long crack and jiggled the head to spread the lips apart and settle him against my hole. He was so large, my big inner labia barely showed to the side of the head as he pressed against me, where they would remain until I somehow got this giant cock inside my virgin pussy. "I have to admit, the blonde on black looks cool, doesn't it?" I asked.

He didn't answer, his focus entirely on insertion. He pressed forward, but the spongy head couldn't budge my opening as the floppy penis bent. "Rub it in the bush a little to get it started, then I'll get fully hard inside you," he said.

"Nervous doing it in public?" I teased "Step up and get it done, stud."

"I agree. We should be showering by now." He moved his hands up to my breasts and massaged them through my dress. He smiled, and I really hoped that he'd been wanting to touch them for a long time.

I rubbed the head up and down my vulva, enjoying feeling the powerful unit respond to his desire to take me. He swelled some more but still had a ways to go. This felt so right, I thought, lust taking over my rational thought. He was supposed to be inside me. I pulled the unit, trying to open my vagina, but there was no way. He was too big to fit in without a stronger erection.

"I don't think it's going to happen," I said. "It's because you're so friggin' enormous. It has to be harder to penetrate."

"It's no problem. Here, let me help you get it started." I still gripped just behind his head, and now he moved a hand from my breast and gripped the base of his cock. I felt the blood being forced into the head, hardening it along with a few inches of shaft behind it. He drove forward. Since he was uncircumcised, his skin didn't even have to budge in my grip; I couldn't have stopped him if I'd wanted to. I felt the shaft slide under his extra foreskin between my fingers, and the head disappeared completely from my view under my clitoral hood, probing between my big lips as he struggled to gain entrance. If he had been smaller, I wouldn't have been a virgin anymore. He would have been in, and it would have hurt more. But he just pressed the whole entrance back, my clenched muscles keeping the intruder out.

I grunted in surprise and slight discomfort. He relaxed the pressure, then drove forward again. The second thrust bounced harmlessly off my clit. I pulled his prick back down to my entrance and corrected his aim for the next thrust. I could feel him making progress, but I sensed my opening stretching against the blunt tip more inward than around the head to really take him. "Hold on," I said, keeping a grip on his cock while I scooted my butt off the edge of the desk a little while compensating for it by leaning back more. I was surprised I could fit my tall torso on his desk with my head leaned up only slightly, mashed against the soft cubicle wall. I readjusted my dress to expose my pussy again, then lifted my legs higher than before and spread them wide. I released his penis and reached under my legs, spreading my butt cheeks to pull apart the flesh near the bottom of the vulva and part the lips wide. The tissues opened up more, and I felt looser down there and ready to receive him. "Try it now. All the way in this time, Jeremiah," I pleaded.

He took control of his penis now, aligning the tip against my hole with one hand while squeezing the base again with the other to harden the upper end of the shaft. I saw his head and surrounding area shiny now with my natural lubricant. I looked up and met his eyes. I felt intense pressure again for a couple seconds, but nothing happened. But Jeremiah was constant and unyielding this time, and I soon felt the burn. It was finally happening. I thought I felt something tear, and the pain was intense. But his cock wasn't going in. I finally gained a full appreciation for how large this man was. The crown of that enormous head was still perched outside my pussy. I groaned and put my hand on his hip. This time he noticed the grimace on my face and relaxed his grip. The head went soft again and slid out of the indentation of my hole. That was three unsuccessful attempts at my stubborn maidenhead. "Holy... grande. You're a big boy," I said.

On the last thrust, I had looked into his eyes the whole time. I thought I saw something there, maybe a bit more emotion than the lustful hookup we had going. Was it some form of tenderness or affection? It was hard to tell. "You are really tight," he said. "Do you want to go down on me for a while and get me fully up before we try again?"

"Sure, definitely, " I said sincerely.

Jeremiah and I traded places, and I happily took his large cock into my mouth. I had given plenty of blow jobs before, mostly to that one guy I had dated for three months. I loved to do it and liked to think I was pretty good at it. I realized right away I would have to adjust my technique. I certainly couldn't take all his length, and his large girth took so much space in my mouth, it was harder to freely move my tongue along all the sides of him like I wanted. But his moans told me my adjustments were working. His hands went to my head. I let his cock plop out noisily. "You have to tell me if anyone is coming," I said. "I tend to clamp my teeth down with a strong bite when I am surprised." He laughed.

I continued, and within a minute he was fully hard. It was impressive for sure, and I told him so. "Shall we try again?" he asked.

By now I had gotten control of my urges, and I knew sex was a very bad idea. I wasn't ready to sink morally into a one-night stand at work right out of the gate with my budding sex life, and I'd probably end up pregnant. "Let's finish like this. I think it is safest." To his credit, he didn't seem upset or try to make me change my mind.

I knew he was close anyway. By the time he was fully hard, I could tell from his breathing and the amount of fluid already oozing out of the tip that the end was near. This was my favorite part. I loved having this control over men, feeling them respond in the ultimate way to my talents. I didn't think taking a load was gross or degrading in any way. I didn't necessarily love the taste or the slimy texture, but I didn't mind it either. And I loved the sticky aftertaste that lingered, reminding me what I good time the man had thanks to me.

Jeremiah gave me a courtesy warning a few seconds early in a hushed voice, then he climaxed quietly also. We both enjoyed risking getting caught, but we certainly didn't want to actually get caught. He pumped his ejaculate into my mouth powerfully and deep, but the amount of spunk wasn't that much. I imagined he had lots of willing outlets to drain it often. I swallowed the evidence easily enough.

"Damn, girl, you're good," he said as I stood. "See, we should have been doing this all along."

"I'm only doing it because I'm leaving tomorrow," I said and patted his butt.

"Well, I'll take it. Thanks."

"My pleasure. Now I need to go to the restroom, then I'm getting out of here," I said.

I peed, then when I wiped, I noticed a spot of blood on the paper. Maybe I had taken more of his monster cock than I thought.

I wasn't sure how to say bye to Jeremiah, but fortunately he was a man about it and took charge. He was done working, and I happily accepted his offer to carry my box and walk me to my car.

When he went for the hug goodbye in the dark, deserted parking lot, I completely lost my aggressive persona from earlier. Then the first kiss came, and I didn't turn away. When I realized it was more than a quick peck, I opened my mouth for the french kiss. He was good, and I wondered if his semen was still on my breath. While I wasn't sure about mine, his breath was great. I liked his attention to detail. "Maybe I was wrong to put you off a while back," I confessed. "I admit I'm very attracted to you now. I like how you can be both a gentleman and a sexual pervert when you need to be."

"I'd really like to finish what we started," he said. "I like you for the right reasons, you know that. But I've wanted to just fuck you like crazy for a long time, too. Especially after you got promoted the first time. I like strong women. I've wanted to bend you over your desk and take you for so long now."

"There's the pervert again, and so far I kind of like him. But I'm a bit old-fashioned. This was out of character for me. I'm going to admit to you there will need to be a real first date, then a normal dating process before this happens again. It would be worth it for you though," I added confidently.

He laughed. "I'm sure it would be. But you're moving."

"You used to work in logistics right?" I asked. He nodded. "We'll, if you think I'm worth it, you'll find a way." The car door was open, and I turned to leave him. Then I stopped, feeling both overconfident and like I needed to give him a stronger nudge to try again. I leaned in for another hug. His cock might have been soft now, but the large presence still asserted itself as it pressed against my crotch. "Mmm, I can feel you down there. So big. Maybe we can take our time and make it fit next time," I said, hoping he would want it bad enough to make the drive and ignore the harem of women he probably had nearby.

"Are you still a virgin?" he asked, seemingly out of the blue.

"What?" I wasn't planning on sharing that with him. It didn't fit with the way I had taken charge earlier, and I worried he would respect me less. Taken by surprise, I stammered, "How did you... I mean, why do you think..." I knew Jeremiah would see through any bullshit now. I had no choice but to own it and hope it turned him on. I whispered in his ear, even though nobody could have heard if I had screamed. "I'm not sure. How far in did you get?"

Jeremiah laughed and held me, and I actually felt a boner grow from nothing to close to full mast in a few seconds. I countered his look of doubt with a nod, and he was convinced. "You've never been fucked? Come on, really?"

"Not unless you think we successfully consummated it already."

"Almost, but no. We'll have to try harder again later," he replied.

"Good," I said, patting his butt affectionately. "Something to look forward to next time. Just don't tell anyone, or I'll have to kill you. I shouldn't be ashamed, but it's just something that's best kept between us." Then I turned and left him alone in the parking lot with a hard cock. Jeremiah definitely had my interest. It took him six months to call me, but when he did, I answered and got that first date and then some.

This time with Jeremiah is not the theme of this story, but it was essential for me to be relaxed and primed for Elena later.

The next day was our company's holiday party. I'd been looking forward to it for a while. It was an unofficial coming out party for me at my ideal weight. The weight loss would be obvious to anyone that hadn't seen me in a while. It would also be the first time I'd see a lot of my coworkers from the new office that would make the drive down and spend the night at the hotel hosting the party. The party was a big deal for our company each year, and the owner would spare no expense after our great year. We'd have an open bar, plenty of entertainment, and party well into the night.

Unfortunately, there weren't many dating prospects in the new office, just a couple single guys I knew of that I'd even be interested in if they hit on me, which was unlikely. And I'd be wise to stay away from getting too friendly with the people from the new office. But a lady could hope. My sex drive had never been higher. I now had a primed, fit body, and I was dying to finally put it to use.

I was incredibly horny the evening of the party. I'd been masturbating once or twice most days since I'd last seen Elena, but it was not curbing my appetite at all. The previous day's orgasms courtesy of public masturbation and Jeremiah fanned the flames and made the issue worse. I had been thinking about Jeremiah all day, wondering how that big cock would have felt had he managed to cram it into me. I decided I needed more than just the new body and the new clothes to commemorate the night. I could think of one other area in which I needed to modernize, and I was surprised at how easy the decision was once the idea came to me.

I knew I was behind the times with a full bush. I loved the look on Elena, and I'd heard it felt great too. So I was going to do it, for me. I tried to make the experience memorable as I sat on a towel over a pillow in my den in front of a full-length mirror. I streamed a good porn video to the TV to get in the mood. I owned a cheap pair of clippers, and I began by mowing down the entire bush. I almost left a patch above my crack, because I really liked the authentic light blonde look, and even a partial shave would test my conservative personality. But I decided to go all-in and mow it to the ground. I wet the area with a hot washcloth, then took my razor and cleaned off the stubble. I raised my legs high and, feeling more than a little silly, shaved the yellow fuzz around my butthole too. My non-virgin butthole, I reminded myself. Now that some time had passed, I was oddly proud to have taken it in the ass already.

I cleaned off the shaving cream and came back fresh and clean with a new towel and looked at myself in the mirror with spread legs. I had been self-conscious of my pussy lips before, but now I could really see them well for the first time in my life. They seemed huge. I decided they were perfect and gorgeous. Since I was on the tall side at just over six feet, I didn't have a small pussy. The crack was tall, enveloped by lips that were larger in proportion to the pussy anyway and jutted out about an inch. I could pull them and stretch them out to over two inches easily. I ran my finger through them and peeled them back, and they reached across much of my outer labia when fully extended. The light pink flesh was damp and glistening in the light. I was already aroused from all the solo attention. I had time to play before the party, and I was going to make the most of it.

In addition to the bush being gone, with my new, slender figure, I could see much better over my flat tummy. I had improved my flexibility and was surprised at how wide I could spread my legs, exposing my pussy even more for inspection. My hand pressed lightly against the lips, and I could easily feel the difference. Already the cool air against newly exposed, hairless flesh was turning me on. My hand rested against a bare vulva, the dangling fingers anxious to play. I gently inserted my middle finger while enjoying the feel of my palm resting against shaved skin. I gave a very content sigh of pleasure. Despite the large size of my crack, the hole itself was tiny. My single digit felt cramped as always inside my unused vagina, which gripped it tightly as I smiled in pleasure.

I had inspected myself many times like this, just for fun or to watch myself masturbate. I doubt that was normal behavior, but I didn't care. My tilting full-length mirror was exactly for this purpose. I gently tugged at the lips and pulled them apart and slightly downward in a practiced movement. There it was, the evidence of my virginity. I noticed right away why I bled after Jeremiah's failed insertion. I had a partial tear in the upper right side of my hymen that wasn't there before. The rest of the perimeter was intact as it had been before. The stud had given a valiant effort, but I knew I would have to stretch more to fully accommodate my first penis.

I reached into the shoe box next to me and pulled out my bottle of lube. I dribbled it on my pussy lips and reinserted my finger to work it in. I alternated between flowing the finger in and out of the hole and rubbing my clit, and soon I was approaching orgasm. I could climax in a variety of positions, but my favorite was on my belly with my legs closed tight. I knew I was less than thirty seconds away if I rolled over. But I wanted to drag this one out.

I pulled my Rabbit vibrator out of the box. I had purchased this a few months before, grateful for the covert online shopping experience that modern society afforded. As I lost weight and my libido increased, I was determined to expand my sexual boundaries since I wasn't getting laid. The shaft was thick, at least as big as the average penis. It could vibrate or twirl to get someone off as it slid in and out. The base had a small tickler sticking out of it, designed to vibrate intensely against my clit as I inserted the dildo. The tickler worked really well, and I had used it many times to get off just pressing it against myself, but I had never inserted the actual shaft. I wasn't too emotionally attached to any physical signs of my virginity, yet I still hesitated.

I set that aside for the moment and took the other vibe out of the packaging. It was a cheap one that came free with the more expensive rabbit. About three quarters of an inch in diameter, it was barely wider than my finger and maybe an inch longer. I applied the lube and brought the tip to my pussy. I went very slowly, and the small toy slid inside no problem. It felt tight, but I knew I didn't have to tear more to take it. I slid it in and out for a few minutes before moving on.

I turned to the large rabbit and pondered if it I should give it a try. I was very curious to feel something of more size inside me. I also didn't relish the idea of going through a potentially painful, bloody experience as a 23-year-old woman on my first time, whenever that finally happened. I knew I shouldn't be embarrassed to be a virgin, but I felt like a naive teenager.

I brought the tip to my pussy and relished the feeling of the large device about to enter me. Even though I didn't put it in before, having it against my lips about to fuck me caused my mind to open and fantasies to run wild, making the subsequent masturbation so much better. My ample lips were already peeled back, and I felt the vibrations flood my entire vulva. It was heavenly, both the pleasures of the moment and the anticipation of insertion. I had waited a long time to try this. I could see everything in the mirror, and it was a huge turn on. My pussy released more and more of its own lubrication as I rested the dildo on the outside. The cute lips curled and bent to the side around the tip of the large shaft. I could see my body sweating slightly and my face flushed with excitement.

Thoughts of Elena filled my mind. I had been so stupid, and now I wasn't going to get another chance. She had been so close, ready to be intimate with me, and I had blown it. Sure, the circumstances of the evening weren't perfect, but she had my half-nude body straddling her, the dildo at my door and about to slide in. What more did I need? Why did a piece of plastic suddenly freak me out? If I had waited another few seconds, there would have been no turning back. What would it have been like? I imagined her joining with me, her tool finally entering me.

My thoughts drifted to my recent office encounter with Jeremiah, whose giant cock had hardened so well in my mouth. He wouldn't hesitate next time. He would look me lovingly in the eyes while he thrust into me, stretching me and filling me up, then he would cool me off with a gushing flood of his thick cum. The thought almost made me climax, and I fought a huge desire to plunge the dildo inside my hungry pussy. I joined a second hand at the base and prepared to thrust forcefully inside and get it over with. The opening felt wider and wetter after using the lubed vibe earlier, and I anticipated an easy, if not painful, deflowering.




The Holiday Party



But I stopped and didn't go through with it. I groaned in frustration, recognizing that I was an emotional, indecisive mess. I wasn't scared of penetration. I think it was more my mind telling me being a virgin was special, not an embarrassment. Both thoughts were there, and the second one arrived just in time. But there was something I could still do to take things to the next level.

I positioned myself on my side with my knees to my chest. I started with a lubed finger in the tush. Only Elena's dildo had entered my butt the other way before now. I took my time teasing the entrance and pushed in when I was relaxed. The untrained muscles gripped the digit hard, and there was just a tiny bit of pain. I could feel the ring of muscles relax, and I tested it again with a few probings from my finger.

I brought the rabbit to my anus and gently pressed. It felt huge, and it didn't budge at first. I didn't force it, and when I reached back to turn on the vibrations again, it began to slip inside. A couple minutes later and my muscles relaxed. I gasped as it entered, but this time it was completely pain free. A smooth insertion followed, and I had taken it all. Wow, this felt great! I wasn't expecting to like it, but I definitely did. I moved it in and out slowly, breaking myself in over the next five minutes. That little tickler designed to hit the clit felt great on my perineum when the unit was fully inside my ass.

I kept going for another ten minutes or so and could slide the dildo in and out very easily. I pulled it all the way out and re-inserted, awed by the fact I could gape myself slightly just like the porn stars. I thought it was sexy as hell, although I'm sure I'd be mortified if anyone else saw me like this. I sensed the anal pleasure was indeed bringing me near orgasm, but I might need a little extra help to get over the top. I turned over to my stomach on the floor with my butt raised slightly on top of that pillow. The logistics were challenging: I had to reach behind to hold the dildo in my ass. I reached under to my crotch with my other hand and found my clit, and I got off in no time.

I laughed and stood, feeling both silly and proud for my experimentation. But as fun as it was, it only left me wanting another person's touch even more. My poor coworkers were about to run into a hormonal mess trolling for cock. The anal action triggered a trip to the toilet and a long shower to get out the sticky lube, then I was ready to prep for the party.

Unlike most of the times I put on nice clothes, I really enjoyed getting ready. I'd purchased my first thong panty to celebrate my new body. I slipped into the tiny black garment and looked into the mirror for a few minutes, admiring the figure I had worked so hard to improve. I smiled big, able now to ignore quite nicely my remaining imperfections. I took my time working in some body to my blonde hair. I had never been more confident in my appearance and sexuality.

I really wanted to wear the new jeans I spent two hours picking out the previous week to show off my new body. I thought my ass looked its lifetime-best in them. But I erred on the dressier side. We were a tech company and very casual, but jeans would be pushing it. I settled on coupling high, dark stockings with a new skater skirt that was dressy and flirty. I needed stockings to darken my fair skin. I connected the stockings to a new garter that was also a first for me. I just never felt sexy enough to try one before. I always had issues with nylons. I had some elastic ones that made the top of my legs look fat. Full pantyhose turned my pussy into a sweaty, gross mess. The garter was much sexier and allowed my pussy to breathe. It was a few inches thick, a six-strap version for real daily use versus just lingerie. But the lacy material still looked great for the extremely unlikely scenario that someone besides me saw it this century. The skirt's fabric was dark and thick, suitable for winter wear. It was abnormally hot for December that night, so I wouldn't be cold.

I added a top that showcased my bust with a little cleavage, but not nearly as much a I could bring out. It had buttons, so I could adjust cleavage on the fly later. I owned lots of shape wear or form-altering undergarments, whatever we were calling them now. I was skilled at hiding my fat in work outfits. But now I didn't need them, and I happily left the constricting items off my frame.

I was proud of the curves in my tush now, and therefore was annoyed I couldn't show them off as well as I'd like. But I enjoyed turning to the side and not seeing any more of that belly pooch sticking out over my skirt. I tried some black shoes with three inch heels, but made a last minute bold change to some tall black boots on the way out the door, and I was confident and ready to impress. After a lifetime of hating shopping and all things related to fashion, getting dressed was fun.

I arrived fashionably late. Most of my coworkers were there. I saw a few ladies there with jeans, and while I was annoyed I wasn't wearing mine, I knew they were under-dressed. I blended into the crowd and made my first couple trips to the open bar. The music was loud and the mood great. They had just announced our holiday bonus payouts, and everyone had a reason to celebrate.

After a couple drinks, I visited the ladies' room. I took off that tiny thong I was wearing and put it in my small handbag. I was feeling sexy and confident, and it seemed like a nice way to spice up the evening since I wasn't going to get laid. It was certainly my first time commando in a skirt, with the added bonus of a freshly shaved pussy. The effect was immediate. The skater skirt seemed to waft in fresh air with every step to tickle my privates. My exposed labia were hypersensitive and detected every movement. From that moment on, all I could think about was getting fucked. It was a huge distraction from what was actually an important social function for my career, but it was worth it. It was so hot also to worry about accidentally flashing everyone.

I was definitely wrong about the guy prospects. With the jubilant mood and open bar, I had tons of guys hitting on me, including the married men. I even had one guy from the new office try to get me to "bounce" with him as he called it. He had a hotel room there, so the logistics were simple. He was cute, and I'm sure it would have been fun, but I reluctantly declined. I sized up every guy to assess if I wanted to have sex. The answer was almost always yes. I wouldn't do it, because I knew I had to have some standards and at least know the guy in advance, but I still knew I wanted to. I was certain the hard work on my body was paying off. This was by far the most attention I'd gotten from men before, and the free alcohol was simply not enough by itself to explain what was happening.

After a couple hours and three stiff drinks, the fun began to fade, even with the free-flowing air around my genitals. My introversion was kicking in. I settled in the corner of the large room at the bar to cool down. I would have to stop drinking shortly or commit to taking a cab. I wanted to drive, since the movers were coming early the next day, and I had to take care of business. A manager that sat a couple aisles away from me at work pulled up to the bar and sat two seats down. He tried to act nonchalant as he got a drink and made conversation. This was Mitch, a hopelessly single man. He was all work and no fun, out of shape, and a bit crass. My body language did nothing to dissuade him from hitting on me. But he worked hard at the office and was a valuable asset, so I showed him respect and endured his moves.

This is when I got the message that changed my life. It came across Facebook's messaging app. From Elena: "Enjoying the party?"

Seriously? All the days had passed since the awkward split, and she comes at me with a causal comment like nothing had happened? No doubt she had seen that I was going to this event. We were "encouraged" to check in on Facebook for the event and promote the company on social media. My heart started racing. I had to see her if she was offering it. "I could use a rescue," I replied.

Then that was it. I didn't hear anything back. Mitch returned from the restroom, and people continued to come to the bar for refills and make conversation with me. I stared into my drink for a few moments when I smelled something familiar. It was Elena's new brand of perfume.

"How about the Rudolf Tipsy Spritzer," she said to the bartender. It was the special drink they were pimping to us for the party, and it wasn't half bad. Elena had inserted herself between me and the boorish coworker, but she had yet to acknowledge me. She was in a nice pair of slacks, a sexy top, trendy dress shoes, and long, styled black hair to die for. She was gorgeous, although the outfit seemed off. The pants looked like good executive wear, but she paired it with a great hair style and top I'd expect to see at night. Poor Mitch was floored by her aura and couldn't talk for a few seconds.

"I don't believe we've met, love," he said, annoying me by competing for her attention. But I was amused to see what she would do, and it gave me a moment to recover from the shock of seeing her while I checked her out.

"Esmerelda," she said, thickening her already fake Spanish accent. Then she leaned in close to him, and I know he could feel her breath on his face along with the light touch of her right breast on his shoulder. "I'm crashing the party, hope you don't mind. I'm staying in the hotel for the most dull conference you can imagine, and I saw all these people having fun."

Mitch sure wasn't going to whine about this beauty getting a drink on the company's dime. "Our bar is at your disposal. Nice accent. Where are you from?"

"Argentina," my Slavic friend told her drunk suitor. I laughed and waited patiently. She was still close to him, and I heard her compliment his ring. It was his Naval Academy ring, and he sure was proud of that thing. I'm not dissing his service at all. I am just pointing out that Elena was as smooth an operator as they come at building rapport with men. He was eating out of the palm of her hand. Just then one of the Vice Presidents of the company shouted his name and called him over. He was gone, and suddenly Elena and I were alone. By coincidence or God's gift, the bartender was occupied, and all the party guests had full drinks for few minutes. 

Elena sat and faced me. "Nice name tag... Brit," she said with a touch of sarcasm. "At least it draws attention to the nicest places," she said and gazed at my breasts.

Like every girl there, I was annoyed that we had to wear name tags, but it was required since we were mixing offices and lots of people hadn't met. But most women had already removed the ugly things after making introductions. I ripped off the sticker for good. "Do you like looking at my tits, Esmerelda?" I said, playing along with the fake name she had used on my coworker. I adored her for it. I had yet to know her agenda, but she was saving her true identity for me, and that was a good sign. She was here to be with me, not to mingle.

"Yes. When I came in, I just went for the tallest, most beautiful woman with the best rack I could find," she said. "You seem like a nice person, Ms. Brit. I will tell you why I am here, and you tell me if I am crazy."

"Okay."

"I have a huge crush on a girl. She is the only girl I have liked in this way, so I don't know how to act."

My heart was beating faster now. "Go on," I said with a smile. We both knew Elena had banged many girls, but I loved how she was acting like I was the only one.

"It's complicated. She's the best friend I've had, and that means more to me than anything. But I'm so sexually attracted to her. I don't know why her. Well, that's not true. I could give you a thousand reasons why I am attracted to her. I will always love men, I will marry a man one day. But if I ever love a man half as much as I love her, I will be truly blessed. Do you know how I feel?" she said. I saw a bit of uncertainty in her eyes now.

"I know exactly how you feel," I said softly. I didn't smile yet. Was this for real?

"You've felt that with another woman before?" she asked.

"Only once. What happened with your crush?"

"I may have taken advantage of her at a weak moment. I sodomized her and hurt her feelings." She caught me in the act of drinking and made me spew a little, as I couldn't avoid the laugh. "Then I went out of town and was scared to reach out. Maybe my dark past freaked her out. But I miss her so much it hurts."

"Maybe your crush felt like a naive and immature tease around someone so experienced. She probably thinks what you've been through is part of what makes you a caring, strong woman, and makes you even more attractive. What do you want from her now?"

"I want it like it was, best friends that tell each other anything. I don't want to ever worry about that part of us again. But if she's interested, and one day when she's ready, I still want to fuck her." That was a perfectly timed use of the F-bomb, and she covertly rubbed the tip of her shoe against my calf to emphasize the point.

"Perhaps she's missed you too, and would be open to more experimentation," I said. My eyes were tearing up now. I fought it, and lost. I broke character. "I'm so glad you're here." One tear escaped and slid down my cheek. That was it. I managed to stay in control after that with just watery, red eyes and a glowing smile.

"Don't cry," she said. Her own eyes were starting to tear up. We both laughed. There was a brief pause, then Elena casually reached out and ran her fingernail on my upper leg just below the skirt, her eyebrows arched slightly, and her lips puckered just a little. A barely-noticeable gesture to anyone that happened to see it, but it was a total come-on to me that lit me on fire. "Can we step outside and catch up some more? It's your last night here, and I know this party is important for you though."

"I've been here a while and talked to about everyone. I'll see them again since I'm staying with the same company. I think I can step out for a bit."

Lucky for me the scene was chaotic now with louder music, dimmer lights, and widespread inebriation. We walked together casually and didn't need to make a big deal about leaving the party. The CEO and my old boss happened to be standing next to each other near the doorway. I said I was going to get some air with an old friend, and I hoped to catch up with them later. They barely noticed me slip out with Elena.

The large multipurpose room hosting the party was near the top floor with a large balcony and a great view. The company had truly spared no expense. We walked by the more expensive hotel suites on the way to the elevators, but we never made it. Elena stopped at a door that was cracked to one of the suites. The cleaning cart had blocked the door. At this hour, if it was vacant, it would be for the rest of the night. She led me inside, moving the cart and letting the door close behind her.

"I know you won't mess up a hotel room you didn't pay for. You're such an angel," Elena said. "Let's just go out on the balcony and hang out together since it's so warm."

We left all the lights off in the room so as to not draw any attention from hotel employees. I could see decently enough since the curtains were peeled back from the balcony door. We slid open the door and went out. I was impressed. We were near the top of the hotel and had a great view of the city.

We slid the door shut behind us but left the blinds open so we'd know if an employee came in the suite. The ambient light from the city was enough to see each other well but offer decent privacy from prying eyes, although at the moment I had no idea we would need it. The rail came up to my belly button with a solid wall under it, so everything from the waist down was completely obscured from view. The sides were a solid wall, so we had privacy from other suites. There were other buildings across from us, but a peeping tom would require some powerful binoculars to see anything worthwhile.

We went to the rail and silently stared at the city. It was a quiet night with small amounts of people milling around many stories below. The gentle breeze and temperature were perfect. It was just cool enough where I wanted to draw close to her. I put my arm around her and grinned. She leaned in and held me close. We made small talk for a while about my upcoming move. I asked about her job and training business.

I held her tighter and made the first move. That seemed fair. First I killed the small talk by telling her how much she meant to me, and that she should never let so much time go by without talking again. She agreed, and then I said, "I want us to kiss again before I leave. Like we mean it." I leaned in, taking the direct approach.

Elena met me halfway, and we took our time with the first few kisses. I had been so scared I'd never see her again. When my lips touched hers, a huge wave of relief swept over me, and I just felt whole again. I opened my mouth slightly to invite her in, but she pulled back. "Finally. I've been thinking about those juicy, big lips of yours for a while now. Let's move back and not be so obvious." I leaned against the side wall a few feet back. This gave us almost complete privacy versus hanging over the rail. I spread my legs to lower myself to her height better. She came between them and pressed me against the wall to kiss again.

This time she slid her tongue inside, and we began a kiss that lasted for about half an hour. Nobody ever kissed me like Elena. Over the past few months I had dated a lot of guys I met online, and I had no problems giving up a first date kiss. None of them came close. Her familiar smell filled my senses as her soft breasts pressed against mine. I normally closed my eyes during a kiss, but I had them open with Elena. The dim city light lights reflected and lit up her beautiful eyes. We'd stop periodically and just hold each other tight, kissing a neck or nibbling an ear, then our lips would meet again. It seemed to go on forever, and while I wanted to rip off my clothes, I didn't feel rushed at all. We could have stayed there all night and I would have been happy.

The change was subtle at first when Elena began to escalate things. Gradually she moved closer between my legs, aligning her pubic bone with mine. Her hips moved in small thrusts and circles, really beginning to activate my clit under my skirt. The kissing became more aggressive, and then she even reached back and pulled on my butt, grinding it into her. My hands were over her shoulders, so I just played with her hair or cupped her face or whatever, allowing her to lead the seduction. She pulled her chest back a little, and suddenly I felt my heavy breasts hanging free She had unhooked my bra without me noticing. She rubbed my stomach for a second under my top to signal her intent. "Yes," I said.

Her hand cupped my bare breast gently as we kissed. I moaned with excitement; her touch was lovely. She squeezed the flesh gently at first over the entire breast before brushing the nipple with a finger. Elena took her time exploring my chest, and soon her other hand joined in. "May I?" she asked as she started to lift my shirt. "I admit I've wanted a closer look for a while now." I nodded, and she pulled the shirt up along with the unhooked bra enough to see my entire chest. "Wow, Brit. You are so beautiful. They are so big, but still have a perfect shape. I love this larger areaola and the big nipples. They're a little bit hard too," she said and playfully rubbed one with her thumb. "I think you're having a good time!"

"You think?" I joked. Then I gasped as Elena took the nipple into her mouth and gently sucked. This turned into a series of moans as she worked my tits. I was blessed with very erogenous nipples that contributed to my sexual response. I had heard some women didn't like too much action there, but I loved it as long as it wasn't too hard in the beginning, and Elena's touch was soft. Plus my nipple piercings had finally healed. The small barbell jewelry made them even more sensitive and harden more readily.




The Holiday Party Gift



[Author's notes: Warning! This is a cuckold story, albeit a different kind of cuckold story. It includes very minor male to male sexual contact. It also includes public humiliation of the husband and sets the stage for further character growth in later chapters, should they ever be written. I have attempted to write an erotic story, rather than a pornographic one. This hopefully will be hot enough to be a Whack off story for the people who like these themes, as it does have a lot of sex in it. For those who don't like these themes please move along. Constructive comments are appreciated, hate speech will be deleted.]



"What does your wife do when she sucks my cock?" I ask as I show him the picture of her on my phone. You can see the urinals of the posh men's room in the background, the foreground consumed with her worshiping my cock. Her red hair is cut into an Anna Wintour approved twenties flapper helmet, as her bright red lips brush the helmet of my prick. Her right hand is wrapped around the base of my shaft, right up against my balls, with her blood red nails clearly displayed. I remember it clearly since she is stroking me so hard it is practically a punch in the balls at the time.

He gulps hard, searching for the right response, as his mind tries to grasp what he is seeing. Thoughts of "OMG, there's as much cock outside her hand as in it", and "Was he the only one?" flash through his mind.

"She swallows?" he answers timidly.

Sliding my finger on the screen on to the next picture, I taunt him "Of COURSE she swallows. She said my cock was easily twice the size of yours, but that you would need proof. But that still doesn't answer the question. Try again." This one has her deep throat skills on full display, her right hand flat behind my balls as her ruby red lips kiss them from the other side, her nose in my salt and pepper pubes. This time her beautiful blue-gray eyes are closed, a mask of bliss and adoration, with her smoky eye makeup shadowing her eyelids.

"She's fallen in love with your cock?" he says with a hint of fear in his voice, trembling with excitement at the same time. He snatches his scotch and water from the bar and downs it in a single glug-glug-glug. Then he blushes.

I taunt him further. "Just like you just did? Tell me that wasn't my cock you were just slurping on in your mind as you downed that drink and I'll give her back to you." 

He gasps like a fish as he tries to stammer out a reply "But...But..."

"But nothing." I taunt him some more. "Of COURSE she fell in love with my cock. But her terms were that you get the answer right within three guesses or she is mine forever. I'll give you the last hint." I slide my finger to the next picture, both her hands wrapped around my cock as her open mouth lifts off the tip, her tongue flicking beneath, outstretched, waiting, quivering.

"For the last time, and for all the rights to bed your wife at anytime and place of my choosing for the rest of her life: what does your wife do when she sucks my cock?"

He has a wild look in his eyes as he realizes he is trapped, and that he has been trapped by his own wife. Betrayed and given the gift of his fantasies, all at the same time. So he goes further down the road of his own fantasies.

"She promised to suck off everyone there?" he says as he twitches slightly.

"Beep! Wrong again! You have just lost all fucking rights to the angel known as Joanna." I say as I marvel at her mind. She knows him so well she predicted his answers. She probably was one of those chess players who can see five moves ahead of however many moves you can see ahead. I slide my finger to reveal the last picture. It is a wider angle shot than the others, bouncing off the mirror wall of the bathroom to reveal she and I are the only people there. She is on her knees, right hand on my cock, tongue taking the spurts of my come, as her left hand reaches into her slit skirt. She is clearly in the throes of orgasm, even as she gulps down my seed.

"The correct answer to the question, what do I do when I suck his cock – is that I come, just like you just have." she says softly as she joins us, grabbing my hand and guiding it between his legs. I can feel his cock spurting through his pants, as he moans. She bends over to kiss him, the taste of my come fresh in her mouth, and I swear another set of pulses try to empty his already drained balls.

"Escort me home, James." she says to me as she looks back at him. "Edwin, don't try to cover up. Let everyone see you came all over yourself as another man takes your wife home."

______________________________________________________________________________

Earlier that night

______________________________________________________________________________

It is an away mission, and I am the designated red shirt.

Harmony is TDY in NY, and I am stuck at home base in Chicago. Thirty years I've been out of the military, and I still think in those terms. It isn't 7 pm, it is 19:00 local, or 01:00 Zulu. Did my four and out, but it left a legacy of work in the military/intelligence complex I'd successfully exploited for the past three decades. So here I am, forced TDY to her company party, full of people I'd barely met. Edwin, her boss, was here somewhere.

The company party it at a nice enough place. The carpet is a lush red and gold brocade with a fleur-de-lis pattern. The woodwork is ornate, the stone is marble, and you know it is for the six figure and up salary crowd. I am admiring the broad mezzanine staircase, at least fifty feet wide with a central rail, clearly something designed in the twenties or thirties, even though nothing here could possibly be that old.

She appears. If I am writing a myth about a Goddess, I must say she steps off a cloud, but all I can offer is a moment of inattention on my part. Yet she is clearly more goddess than human. She strikes the pose, and holds it. It takes a moment for my foggy brain to process it, then it clicks. I snatch up my cell phone and advance on her position. She glances the other way, over to the bar to my left, then returns to the pose. I have set my phone to bursts, so I rapidly peel off three frame sets as I advance. Then she moves towards me, as I close the distance to the base of the stairs. She is halfway down the stairs as she stops, looks right at me, then smiles a blindingly brilliant smile directly at me, then repeats her pose, check the bar, pose routine, returning to smile directly at me. My camera is snapping frames like PacMan gobbles dots.

My defenses crushed under her onslaught, I surrender. She is, for all intents and purposes, better looking than Anne Hathaway in Harper's Bazaar. The same black formal Versace dress, off one shoulder, scooped out down to her far superior cleavage, the slit from her pubes down to her ankles – with a zipper, so that it is clear she meant to show you the perfectly sculpted leg. She wears the same knee high strappy sandal/boots, also with zippers. She has red hair, a personal weakness of mine, cut into a helmet right at the jaw line. She is tall, she would look down on my Harmony without the four inch fuck me heels built into her sandal boots.

There is no panty line. There is no support in the dress for her 38DD cleavage, not that she seems to need it. She is obviously twenty years younger and she is also clearly out of the league of any of the people here. She belong in temples, or on Mount Olympus.

I am studying her "smoky eye" makeup, the ruby red lips, the almost harpy lines of her face, but she is smiling at me, and her mouth is moving and I am lost in wondering what that mouth could do to me as she snaps her fingers in front of my face.

"Hello! Are you the photographer? I didn't know they had hired one." she says sharply, bringing me back to the present, as the last of my defenses crumbles. Her bell clear English accent has demolished any resistance. I am hers to do with as she pleases.

I notice the huge diamond on her ring finger and my hopes crash. Not that Harmony and I have not shared ourselves with others over the past twenty years, nor that Harmony isn't even probably at this moment between Celeste's legs (her girlfriend in NY), or even sharing the odd dick they picked up together. So I compose the best, most entertaining response I can come up with on short notice.

"No, just here perving for my wife Harmony. She wanted me to get photos of the hottest women here to see whom we could seduce together later. You are clearly the hottest woman here."

"Harmony – doesn't she work for Edwin?" she asks politely, as she returns to scanning for someone.

"Yes, she does. Looking for someone?" I hope to help her find whatever she is looking for – hoping beyond hope it will be me.

"I'm always looking to go home with somebody." she says playfully, flashing that mind numbing smile at me again.

"I'd really hoped we'd already settled that. I'd hoped it would be me." I play my hand way too early.

"Play your cards right and it might be." she says playfully.

"So how does that work for you? Is your husband here?" I ask with the best playful banter I can muster.

"Yes, he's probably at the bar – trying to find someone for me to go home with too." she says playfully.

"Looking like you do – like an emanation of the goddess herself – you must get your pick then." I said slightly more gushing with interest than I'd intended.

"I do. I really do." she chuckles.

I pull the Ace from my pocket. A downed pilot I rescued gave it to me. It is the one thing I value more than my house – my car – or even my business.

"I play this card then." I say solemnly as I hand it to her.

"Oooh... bright, handsome, and playful. Come to tell me about this card while we look for my husband." she says as she takes my arm, stuffing the ace in her cleavage so it is stuck there like a bookmark.

I should have paid more attention. She undoubtedly knew Edwin was at the bar – she even said so. But she exploited my weakness in not knowing she was his wife. All I knew was that she knew Harmony worked for him. So she took me slowly through the crowd, having me explain the card to everyone, having me take it out from between her breasts, explain it, and put it back. She was literally making me play with her breasts in front of everyone that Edwin worked with, in a way that she could get away with right in public. She knew the owners of the company, she exploited that relationship to flirt with the wife, while she had the three of us play with her breasts as she toyed with us verbally. We had to remove and replace the card because it was back to front, or upside down, or any of a dozen other excuses while she chatted up the wife – a slender B-cup trophy wife acquired more for her tennis skills than anything else – until you literally could smell her excitement running down her legs. Something about touching the breasts of another woman really turned Anna on. The card vanishes as Joanna hugs Anna, which leads to a series of hugs exchanged, where Anna's bee sting nipples tried to drill into my chest, as her husband John grabbed Joanna's ass – so I did the same to Anna, and her scent of arousal became almost overpowering. Joanna then had us switch, so that John was back with Anna, and she literally plastered herself around me, smashing her pillowy boobs into my chest as she ground her groin into my leg. Her "hug" turns right into dry humping me on the Mezzanine. The card reappears, smelling very much like Anna, as I slide my hand fully between her soft breasts.

"C'mon, lets dance", she says as she pulls me away from my dazed stance. The club room is just off to the left of the stairs, above the bar.

Slow romantic ballads are playing as we take the floor, mostly co-workers released from their leashes by alcohol, and getting quite busy, so it is like joining into a big group grope. Joanna pulls me to her, her red lips frantic to kiss me, her hips grinding pounds of hair off her beaver, and then she is moaning into my mouth. Her hand has unzipped me, snaked into my boxers, and is slowly jerking me off, as her body thrashes against me.

"Good God you're well hung." she says softly.

"Good God gave me nine inches so I could give them to you." I reply deliriously.

She pulls back, pops out her compact, and fixes her lipstick.

"Think about baseball for five minutes. Then I'm going to take you someplace private and suck your cock for however long it takes for you to come in my mouth. Time to meet the husband." she says firmly as she takes my hand and leads me to the elevator. Luckily, the wait for the elevator is long enough my boner is almost completely gone by the time we pop out next to the bar.

Finally, I see someone I know. "Edwin! Over here!" I cry out.

Edwin is talking with Rodney, one of those mutton chop guys who thinks the 1800's had a great style. He's at least ten years older than I am and fifty pounds heavier. Edwin is going on at him about something, and Rodney is listening intently. Edwin is management, and Rodney is senior management, so I assume I'm interrupting a business proposal.

"Pwew-wheet!!!" Joanna puts her fingers to her mouth and makes a whistle so loud I'm sure they heard it up in the Mezzanine. Edwin's head snaps around and then he is like a puppet whose strings have been cut, as she grabs my arm to escort me to their table. I'd assumed that the purpose of meeting her husband is to get his approval. The exchange that followed made quick work of that fanciful notion.

"Joanna, you know Rodney, I was hoping..."

"Good evening Rodney! This is my date James." she said very warmly and politely.

"I was kind of hoping after Edwin's encouragement it might be me." Rodney replied as he grabbed her hand possessively in both of his.

"Perhaps another time. Because I most assuredly would enjoy that." Joanna says as she moves behind me, freeing her hand from Rodney's grip, plunging it into the pocket of my pants, literally choosing my cock over his hands in a body language display no one mistook.

"Are we leaving then?" Edwin got up and picked up his coat.

"No Edwin, we are not. Sit down and think real hard about what I'm about to tell you." Joanna said sharply, as everyone was practically blasted back into their seats by her tone.

"I have marched this man throughout this company with his card between my tits. He has already made me come twice, and I'm going to make that up to him. As for you, Rodney, I'm hoping James will let us have a little playtime together, some other time. Because unless Edwin can pass our test tonight, James will determine who does what with me, from here on out. Edwin, do you submit your authority over me as your wife to James, assuming you cannot answer our question correctly?" Joanna says sternly, as her eyes drill into Edwin.

"Yes." Edwin says softly, clearly fearful that the game is rigged.

"Come on, Edwin. This is the one thing you have begged for, to have another man have complete control over whom you wife takes to bed. I have chosen the man, but he thinks it is only fair that you have a chance to win me back before you lose me forever. I will even give you the question ahead of time. Rodney, I think it is best if you say goodnight." Joanna continues her stern tone, as Rodney hustles off.

Joanna leans over and whispers in my ear "Make up a question, something very intimate, like how I suck cock, or how my tongue feels on your dick. If you can, make it about me instead of about you and I promise he will get it wrong. Then I will take you home and be your fuck toy for the rest of my life."

"Ok, Edwin. Here's the question. Joanna and I already know the answer. What does your wife do when she sucks my cock?"

Joanna took my hand, and we walked out of the bar.

She took me up to the Mezzanine, over to the right side, far in the back, where there was an empty hallway, and another set of restrooms. It is so far from the festivities we cannot hear the dance music anymore.

"James, I have to be straightforward with you. My Mother taught me that you can love someone, and you can want someone. The first lasts longer than the second, in most cases. She loved my Father. She wanted our gardener. She had both and all three of them were happy." she smiled that mind bending smile at me again.

"What I didn't know was that I picked a man just like my Father. I learned skills I needed to keep Edwin happy, even though at the time, I despised my Mother for acting like a slut. Now I find out that to keep my Edwin happy, I have to become another man's slut. Worse, I find out I'm very keen on it." she unzips my pants and starts stroking my soft shaft.

"You have a Bi wife. I would very much like to become a Bi wife too. You have been to all the erotic destinations I crave. Yet I love my Edwin. And if I don't have you take me to each and every one of those erotic places, I will lose him, or worse deaden his soul. Because he loves me but he wants you, and most other men, to have me. I love him, but I want most other men, and maybe lots of women to have me too. Yet to stay safe, I need a gatekeeper. I can't do it myself, I would have sucked poor old Rodney off at the drop of a hat to please Edwin. Edwin will never be able to compete with you physically. We need to use that. He has dark needs to be with another man his upbringing cannot allow. We can play with that. We need to give him his fantasy, make it his reality, slowly, and do it all without hurting him. Can you help me do that?" She says as she hauls out my cock, right there in the hallway, blowing me and stroking me like she wants to taste my come that very second.

"That's not very fair. How am I supposed to say no to a goddess on her knees with my cock in her mouth, blowing me to kingdom cums?" I laugh.

She pulls off my cock, smiles that mind bending smile at me and laughs. "You aren't ever going to be able to say no to me." Grabbing me by the cock, she says "Time to make the donuts.", as she leads me out of the hallway, into a men's restroom.

"We will set up here. Drop your trousers, I'm going to need everything you've got on display. I'll take the first few. I'm used to taking cock sucking selfies, I've been sending them back to Edwin, asking him if he can tell who I'm sucking off. He always keeps his eyes closed while I suck his cock so he can fantasize. Oh, hot twist, since these are your pictures, he will have to do things like lick my clit while you fuck me, or clean my pussy out after you've cum in me to get one." Joanna says as she fists my dick to keep me hard.

"Shouldn't you be at least half naked?" I ask hopefully.

"No, I want this to look like I couldn't wait, I had to suck your cock..." Joanna muses as she gets right to it, stopping and posing, clicking shot after shot. I later found out that the camera was still set into burst mode, so I got several shots for each time she thought she had taken only one.

Joanna is a truly talented cock sucker. Her soft lips embrace the head of my prick, her tongue flicking around the tip, as she fists my shaft, trying to pump the come out of my balls. She then drives her throat onto my entire length, without any trace of a gag reflex, and I am balls deep in her throat. She pulls off to say "You are going to have to take some of these."

She grabs my ass cheeks with her red nails, clawing me back into her throat, making me fuck her throat. I am going to have to get her to teach Harmony how to do this!

Joanna pulls back, resting her lips on the tip of my dick, as she fists my cock, only to pull off and pull my balls loose. She can tell I'm getting close to coming. "Uhh, uhh, uhh!" she scolds. "No popping off before we have collected all of our evidence!"

I take pictures from above looking down at her gorgeous face on my cock. I take pictures from each side. I even take some pictures from below (which didn't turn out too well).




The Holiday Party Gift



"Now some pictures for you." Joanna says softly, as she bends over to grab the sink counter hiking up her dress to show me her glistening twat. Her legs, in those heels....

"Don't you think this pussy would look better with your prick inside it?" she says while flashing that mind bending smile.

Don't have to ask me twice! In a flash, I bury my shaft all the way into her, holding my length fully inside her while she shakes and thrashes. I can feel myself reacting to her heat and snugness, so I try to pump as quickly as I can, as her knees buckle. She spins around, grabbing my phone to place her tongue under my cock, then handing the phone back, as her other hand slides up her dress to finish her climax on her clit. Then my balls start pumping, gob after gob, six solid blobs onto her lips and into her waiting mouth as she writhes on the floor. I stop long enough to get the camera back. I take the closing shots of her climax, latched onto the tip of my shaft as the last few dribbles of cum reach her tongue. Joanna climaxes again, and I capture it all for posterity.

"It seems that while I was two climaxes ahead of you when we came up here, I seem to have added five more than you. I may never get you to catch up, but at least we must try. It's only fair to you. Take me home James, and fuck me slow, so Edwin has plenty of time to watch."