An Odd Encounter

The following is a fictional short story written for a special friend to make up for things I'll never do for her. Some things remain fantasy only.

*

I met her on one of those dating sites. Well, when I say dating site I mean one of the many that caters to people looking for random hookups. I don't know exactly what I was looking for at the time. I guess it was just that it had been a while and I was looking for some fun, but she was hot, so it didn't take long for her to convince me to come spend the night at her place.

I arrived a few hours later, nervous, unsure on exactly how everything was going to unfold. At the same time I was incredibly turned on, this wasn't the kind of thing that I usually did!

She answered the door and for a moment I was taken aback. She was every bit as attractive as in her photo. Blond hair down to her shoulders, pale blue eyes with and odd piercing quality, she was short, and yet still somehow slender and curvy at the same time. Just as beautiful, only now I could see her graceful movements rather than just a static picture and I could see her curves jiggle slightly with her movements.

I reflected for a moment that I was out of my league here and wondered how I was going to go through with this without a disappointingly swift ending.

We had a few drinks, and began to talk. A little general chit chat that quickly turned to bedroom topics. She noticed that I was nervous, I wasn't quite sure how to respond. She reassured me before I could think of anything, telling me it was a turn on for her.

She asked me to just relax, and go with the evening and promised if I did that it would be the best sex I'd ever had. She looked directly at me with those piercing blue eyes and asked if I would do whatever she asked. I told her I would.

She led me by the had to the bathroom and stripped me naked. By this point I had a raging erection. She frowned and told me that it was too soon for me to be that aroused, so she put me in the shower and ran the cold water. After what felt like a freezing eternity she added some hot water and stepped into the shower with me.

I realized then that at some point while the water had been cold she had undressed. I drank in the sight of her luscious curves and moved close to her, intending to kiss her. She drew her head back, smiled and said it wasn't time yet, that first she wanted me smooth.

She used some kind of hair removal foam on me, at first she was very business like, but once the hair was gone she became very warm and sensual. She stood behind me, running her hands all over my body and then whispered in my ear that tonight she wanted girlfriend to play with.

For a moment I thought she meant she wanted to call someone else over, then, realizing what she had just done it occurred to me that she meant me. Her hands still wandering, she kissed me, slow and gentle and I melted into her.

She led me out of the shower and stood me against the towel rack. Her hands ran up my legs and onto my now smooth ass, fingers trailing on my skin. She gently pushed my legs apart a little and ran a finger up my inner thigh and onto my hole. I jumped a little, so she pushed her naked body against my back, her other hand resting on my belly and reminded me that I had agreed to let her do anything. I took a breath and did my best to relax.

She leaned a little and grabbed a tube of something, and I felt her finger back on my hole, only this time it was cool and slick. She gently worked me open with one finger at first, then two. I was uncomfortable at first, but her touch was gentle and with her warm and soft body on mine I relaxed and it soon became pleasurable.

She asked me if I'd ever wondered what it was like to be a girl, to feel what they felt during sex. I wasn't sure how to answer, especially with the new-found sensation I was experiencing depriving me of my concentration. I told her I had though about it before and she gripped me a little tighter and pusher her fingers in a little deeper, making me gasp a little. She told me I was going to find out tonight, that my ass was just like a pussy and getting fucked there would feel exactly the same.

She reached out again for the counter and this time I felt her working something larger into me. It slipped in deep, and I felt my ass close around the thinner ending of it. She told me it was a butt plug, to make sure I was ready for her later.

Once more she led me by the hand, this time to her bedroom. She had me stand with my eyes closed by her dresser as she applied makeup to my face and put a wig on my head. Then she began to look through the drawers in her night stand, rummaging until she located what she was looking for. She asked me to turn around. I was nervous, unsure of what she was intending to do, suspecting more of the previous treatment or worse.

Instead I realized she was attaching fake breasts to my chest and putting a bra on me. She whispered to me that I should feel them, and placed my hands on my new breasts. I spent a moment exploring them, they were soft and heavy. She told me that with my erection I wouldn't be able to wear a thong, that instead I would just have to wear crotchless panties instead. I put them on, and then she had me lay on the bed to add stockings. As I lay back I felt a wave of unexpected pleasure. I moaned and a small flood of precum came from my cock.

She smiled and told me I was a slut, and that she knew I would enjoy the plug. I wriggled a little and discovered that the pleasure was the plug pushing against my prostate. It was an extraordinary feeling. She gathered up the precum on my stomach with her fingertips, rubbed it onto her lips then looked me in the eyes and kissed me. At first I was surprised, but there wasn't much taste to it and I was enjoying the slow gentle kiss. She smiled, called me a cum slut and then told me it was time to unveil me.

I was pulled over to her mirror, eyes closed again. She stood behind me, arm wrapped around me, and told me to open my eyes. I saw a beautiful young girl staring back at me. It took me a moment to reconcile that I was looking at myself. My cock grew even harder as the thought crossed my mind that I wanted to fuck myself. Even worse, with the taste of my precum still on my lips and as her hands stroked my ass I realized that I would let myself be taken.

"Are you ready to be fucked?" She asked as she stared into my eyes in the mirror. I had no other answer, I was her slut, ready to do anything. I told her yes.

"She's ready" She called out.

I had a moment of confusion at who she was talking to but only a moment once she pushed me back onto the bed and climbed on top of me, sexily grazing my body with hers, then continued on and flopped down up by my head. I rolled over onto my stomach and looked up at her. She told me to get on all fours and go down on her.

I did as I was told, the vulnerability of being in that pose turning me on even more so. I lowered my face between her legs, as I did so her hands slid up into my hair and her legs wrapped up around my shoulders trapping me where I was. I felt the bed shake, and a hand remove the plug from my ass. Trapped between her legs I looked up at her in a moment of panic, she smiled and told me to relax and go with it. I was so turned on that I didn't fight it. I went back to working her extremely wet pussy.

Strong hands gripped my hips and a hot, slick object bumped against my hole. Because of the plug there wasn't much resistance, the cock entered my ass in one long slow stroke. I moaned into her pussy, which made her gasp and buck against my face.

The Stranger started to fuck me. Every stroke smashed into my prostate, sending waves of intense pleasure through my entire body. I felt my ass flaring open involuntarily on every stroke and I felt I was a half second away from an orgasm which just refused to arrive. My cock was hanging below me, wobbling, leaking small spurts of precum all over my legs and my chest. The fake breasts swinging heavily, reminding me of my new curves and putting the image of my new slutty appearance into my mind.

The fucking increased tempo, the girl, almost forgotten by me at this stage now reached her climax, one so intense that she squirted her juices down my throat and all over my face. I felt finger nails dig into my hips and then a moment later a hot flood of sticky juices coated the inside of my ass. The cock pulled of me, leaving me feeling empty. I rolled down onto my side and felt a dibble of cum leak out of my ass, it turned me on, made me feel like a hot slutty whore. I stretched out, with a feminine curve in my back, and began to lower my hand to my crotch to finish myself off.

Instead the girl straddled my stomach and pushed my wrists above my head. I didn't resist, thinking that she was going to let me enter her and finally cum. No such luck, I found myself tied to the headboard, ball gag in my mouth and still bursting with cum. She pushed a different plug back into my ass, kissed me on the knee and they left me there. As she walked out the door she winked at me and pressed a button on a remote control. Deep in my ass the plug began to vibrate, my cock jumped and my arms and legs strained against the ties holding me to the bed.

I squirmed and wriggled every way I could, but quickly realized that there was no way I was going to be able to make myself cum. I don't know how long I was left there, but it was unbearable. After what seemed an eternity she re-entered the room. She commented on how wet I was. She was right, I was wet, covered in my own precum. She told me if I was a good girl and did one more thing for her that she would let me cum in her.

I was so desperate to release my load I nodded submissively at her before she even told me what she wanted me to do. She took off the gag and let me up off the bed, holding my wrists behind my back, pushing me to a kneeling position on the floor. She made me curve my back a little more and spread my legs apart before tying my wrists. In that position the toy in my ass vibrated against my prostate, making me whimper and moan lightly in pleasure.

She told me that the stranger from before was hard again and needed a release, but that since I was such a slut and was still loose from my previous fucking he didn't want my ass again. She told me it was time for me to be a good little slut, and let him try my mouth now. Even as turned on as I was, I wasn't sure I was prepared to do it, but I said nothing and she called him in.

He walked in and stood naked in front of me. I looked at the cock in front of me and hesitated. The girl's hands ran up my body to my face. She put her hands flat on my cheeks and pulled my jaw down and it thrust into my mouth. I knelt, frozen, lips locked around a strangers cock, unsure what to do. There was a sharp slap on my ass and her hand suddenly gripped my cock tightly, causing me to moan loudly onto his.

I started working it to get my reward, although now I wasn't exactly sure which reward I wanted more, hers... Or his. I bobbed up and down, swirling my tongue around the tip. The girl started whispering in my ear what a whore I was and how much I was enjoying it. It didn't last long, the cock in my mouth grew harder all of a sudden and a moment later a slightly bitter, salty taste flooded my mouth.

At that point she pulled me away and threw me onto the ground on my back, my hands, still tied behind me, dug painfully into me. My ass still full of the vibrating plug, still driving me wild. She sank down onto my cock in one slow graceful move. The heat from her cunt was incredible, and she was more slick than any other girl I'd ever been with. We'd barely begun to fuck when both of us exploded into orgasm. My cock pumped my cum into her with such fury that the contractions hurt me, I moaned loudly, and she collapsed onto me, kissing me deeply, sharing the taste of the cum.

After a minute or two to recover from the most intense orgasm I'd ever had I threw off all that I had on and gathered up my clothes. With the heat and the lust now gone I just wanted to get out of there and process what had happened. I practically ran out the front door.