My First Sexual Experience Was Bisexual


My name is Tim and I’d like to take this opportunity to share some secret experiences that I had when I was a teenager and the circumstances that led up them as well so please bear with me because it’s all relevant. First of all my first sexual experience ever was when I was a teenage boy right after my 15th birthday and it was with another guy, my best friend. (Gary). I have kept this secret locked up for many years and have only recently shared this with my own wife so now I’d like to share with you the circumstances that led up to it.

 As a child growing up I had thick blond hair that my mother always kept very long about half way down my back. As a teenager I was a short skinny kid and I continued to keep my hair long past my shoulders like the boy from that TV show "3rd Rock From The Sun". (only blonde) Yes I know, who cares about that? Well I bring that up because my long hair is actually the focal point of how my first sexual experience began. Anyways I always kept it pulled back in a ponytail when I was out in public because people would constantly mistaken me for a flat chest-ed young girl whenever I wore it down, and now I can see why because looking back at pictures of myself growing up I had very feminine features. My best friend Gary on the other hand was almost two years older and very masculine, he was built much larger than me and kept his hair in a crew cut. At that age I had already gone through puberty and yes, Gary and I both liked girls like normal teenage boys and yes, I had sexual fantasies about most of them including his little sister (Monica). She was my age but she already had a boyfriend. Anyways my dirty little secret was that I sometimes had sexual fantasies about some of the boys as well, and this caused me a lot of internal conflict.

 Gary and I were best friends through middle school and in Jr. high. He was the “alpha male” in the friendship and always decided what we were going to do but mostly we hang out at his house, sometimes drinking beer or wine that he’d swipe from his parent's rec-room bar. But then half way into his junior year he met a girl (Terry), who occupied every minute of his life and was a total ***** towards me. Every time I’d come around she’d make me feel unwelcome as if I were intruding so needless to say my friendship with Gary seemed to stall out. I didn’t have any other buddies to hang with so I spent most of my time reading books in my bedroom or hanging out at the mall and just became very depressed. After school ended for the summer Gary called and said that he broke up with Terry. I couldn’t hide my glee, even over the phone so he invited me to come over. I wasn’t mad at him. I just wanted things to go back to the way they were before Terry came around.

As soon as I got off the phone I rushed over to his house. I was so anxious to see him again that didn’t bother pulling my hair back in the usual ponytail.  When I arrived Gary answered the door and it was obvious by his the expression on his face that he was glad to see me. His parents were gone for the day and his sister was out with her boyfriend somewhere. After some conversion and a few bottles of beer Gary told me right out of the blue that he really liked my hair down and then asked if he could brush it while we watched television.  In the past I’ve allowed my sister to trim it and my female cousin would sometimes play with it but it felt awkward and somewhat emasculating hearing “another guy” ask to brush my hair. After I thought about it I was just so relieved to have my friend back that I relented and let him bush and play with it for the rest of the day until it was time for me to go home.

 Over next couple of weeks he invited me to come over every day and asked to play with my hair each time. I noticed that he was a lot more possessive of me now but when the awkwardness wore off I really began to enjoy the hair brushing and looked forward to the attention. I guess he could tell because he progressed to running his fingers through my hair and then began giving me scalp massages as well. I knew this wasn't normal for two teenage guys and it was also stirring up nervous erotic feelings in me that I never had before and didn't quite understand.

Then on a Friday evening when no one was around we were watching movies and drinking a bottle of Asti Spumante on the big sofa in his rec room when right out of the blue he made another bizarre request. He asked me to lay down on the sofa with my head on his lap! I felt very uneasy about this request and was confused about his motives so I just kind of froze. I guess I must have had a very apprehensive look on my face because he said that he just wanted to brush my hair some more and it was easier than having me sit on the floor in front of him. I still felt awkward but I did comply and he began brushing and stroking my hair while my head lay on his lap. After some time had passed he began gently stroking the top of my head with his fingers and then started touching my neck and face in a sensual way! I really liked how it felt but at that point I felt totally emasculated and was convinced that he wanted me sexually! As I lay there my heart began to pound so hard I thought it was going to jump out of my chest! I was just thinking to myself, OMG! How am I supposed to handle it if he tries something sexual? Sure I’ve had fantasies about guys but the thought of Gary actually trying something sexual with me scared the hell out of me! I was still a virgin and never even made out with a girl yet so I was very conflicted. All I could think was, “Do I want my first time to be with a guy?” When the movie finally ended I got up. I can still picture in my mind how he looked, it was as if he wanted to say something but couldn’t work up the nerve, so I quickly headed to the bathroom trying to bide time to decide how I was going to react if he made a move on me. Then as luck would have it my mother called and needed me to come home. (I can’t remember what she wanted) but I was so relieved for the extra time to think about all this. Before I went home, Gary invited me to come over the following day and stay the rest of the weekend.

That night I couldn’t stop thinking about Gary and his recent behavior. At first I thought that maybe it’s all totally innocent and I might be misinterpreting the way he’s been acting, but the more I thought about it the more I realized that he wanted to have sex with me. That night in bed I stroked myself while fantasizing about all the sexual things he might do to me and was very surprised at the effect that it was having on me. I was actually beginning to regret that he didn’t make a move on me when he had the chance, and the more I though about it the more anxious I was became to find out for sure. I also realized that everything we had been doing lately made me feel somewhat submissive to him and sexually desired and I liked it, so that night I decided that if he tries something sexual with me in the future I would submit to whatever he wants.

  The next morning arrived and I was never so anxious at the possibilities the weekend might have. I knew that his family would be out of the house until the following Monday so he would probably use the opportunity to try whatever he wants with me.  Anyways before heading over to Gary’s house that morning, I washed and dried my hair, making it a point to arrive with it down the way he liked it. When I got there Gary answered the door with a big smile on his face. As we headed to his room he said my hair looked great but he wants to try something different this time. When I went inside I noticed that he set up a chair and a small folding table right next to it. On the table were two curling irons, hairbrushes, some hair clips and other items. This was something new and unexpected but I was resigned to letting him do anything he wants. When he asked if it was all right I sniggered nervously but nodded approval as I sat in the chair and allowed him to proceed in styling hair in long blond curls. After he finished curling it he parted it to the side and clipped one side behind my ear with a flower hair clip, then he handed me a mirror. He definitely gave me a girl's hairstyle and for some odd reason I instantly became aroused! When I stood up I couldn't hide my excitement.  My hard **** was protruding straight out in my gym shorts like a tee-pee! How embarrassing! He just smiled and said that he wants to see how I look as a girl, and then asked if he could put some make up on me!  I just sheepishly whispered, “Sure, I'll do whatever you want". I think he understood what I really meant but anyways, he pulled out a makeup case and proceeded to make me up with eyeliner, a little blush, thick eyelashes, and some lip-gloss. When he finished with the makeup he went to the bathroom, covered the mirror with a bath sheet and handed me a package of safety razors. Then he asked me shave my underarms and legs. When I finished a little while later he handed me a silk nightgown that belonged to his sister and without saying a word I took it from him and put it on. I remember how I felt when he took me over to the full-length mirror on his closet door, what I saw was incredible! Holy Sht! As I looked in the mirror I saw a very pretty girl looking back! I remember thinking that I’d love to **** her if she wasn’t me! After a few moments of stunned silence Gary got out his video camera and said that he wanted to record the way I looked. So when he hooked up the video camcorder to the television I could see myself on the TV as a pretty young girl standing there. Gary asked me to turn slowly for the camera so I did and then after a few close-ups of my hair and face he put the camera on a tripod then had me sit down at the foot of his bed with the camera focused on my face. Then he sat on the bed right next to me and then he whispered in my ear "I’ve always though of you as a girl" then he took my hand and placed it on his crotch. All I could think was OMG! This is it! It’s finally happening! I was so aroused and nervous that I felt like I might pass out! I felt his hard **** through his gym shorts and began rubbing it. Then he put his hand on the back of my head and drew me in kissing me full on the mouth and I kissed back. As we were kissing I kept saying to myself in my mind "I'm a girl! I'm a girl"! After making out for a few minutes he whispered, “You were all I could think of when I was with Terry!” Then he pulled back and while he looked at me he said, “You look so ****-able! OMG! Just hearing him say that made me feel so much like a sexy girl. Then he stood up in front of me and I pulled his hard **** from his tennis shorts. It was very nice, about 6 or 7 inches with a beautiful circumcised head and some pre-*** that I to my lips! Then I eagerly took as much of that beautiful **** as I could into my mouth and as far down my throat as I could take without gagging. I began working it with my tongue and vividly remember how he took my head in his hands and pumped it in my mouth.  He moaned as he pumped saying that I was prettier than most of the girls in school. About 5 minutes later he let out a loud grunt and his **** begin to pulse filling my mouth with his ***!!! My mouth was completely coated and when I tried to swallow it I began gagging, so I ran to the bathroom and rinsed my mouth with mouthwash. When I returned, he looked at me and started laughing a little and said that I would get use to it! When I went back to him he ******** me naked and had me lay down on the bed. My **** was hard again and needed relief bad! As I lay there, he came up beside me and started rubbing my **** and explained to me that he was only attracted to girls and use to just think of me as his best friend. Then he confessed that for more than a year he was having sexual thoughts about me and it freaked him out. I can clearly remember him saying that I was cute like a girl and he still wanted me more than any girl and that’s why he broke up with Terry. It’s hard to put in to words how I felt at that point except that I had just discovered another identity within me. I also realized that since I’ve been back in his life, the things we did were a little bit like how a normal guy acts with a girlfriend and I didn’t want it to stop. I loved the way I looked made up as a girl and discovered that I loved being a girl for him. But anyways hearing him say all of that as he *********** me caused me to shoot *** all over my stomach.

After resting awhile we decided to get up and watch some television with another bottle of Asti. But before going downstairs he fixed up my hair with some fresh curls and pulled it back in a pink hair band. Then he raided Monica’s bedroom for some casual clothes. He returned with a bra and some pads to fill the bra, also a pink pair of shorts a matching halter and a pair of pink socks, so then I knew that I was going to be his girl all weekend.  For the rest of that afternoon we lounged on the big sofa watching movies and drank two bottles of Asti like it was water. While he was holding me close I had hand in his shorts stroking his **** back to life. I was just about to take it out of his shorts and suck it when the basement door flew open! It was his ex-girlfriend Terry and she walked right in on us! Gary pulled my hand out of his shorts and jumped up while I stayed on the sofa frozen in panic! I thought we were totally busted and everybody was going to know! Well as it turned out, she just wanted to return his class ring but didn't recognize me at all! She thought I was his new girlfriend and called me a **** before she stormed out! So as soon as she was gone Gary locked all the doors so we wouldn’t have any more unexpected visitors and then he said “You aren’t Tim this weekend you’re Tina!" and we both busted out laughing in total relief! That night as we headed for his bedroom I remember stopping to use the bathroom, and as I looked at the girl in the bathroom mirror I got very horny again.  So when I got to the bedroom I was glad to see that Gary was lying on the bed waiting for me with a hard on. As I got into bed I went straight for his tool and began sucking it but he stopped me abruptly and pulled me up on the bed and faced me. I was a little confused at but then he grinned and whispered in my ear, “You are so ****-able!” and I noticed his free hand taking a jar of petroleum jelly from his nightstand. I knew then what he had in store for me but since I was totally buzzed from the alcohol I was more than willing to submit to anything he wanted.

Gary positioned me on my hands and knees and applied a lot of petroleum jelly in my anus. I remember the experience very well. He positioned himself behind me and pressed his penis against the opening. At first, it felt kind of good but as he slowly applied more pressure the head of his **** popped inside and OMG! The sharp, intense pain was almost unbearable so I screamed out loud! Gary immediately stopped pushing and held position for several minutes as the initial pain subsided. After a few minutes he began to push in again very slowly. It still hurt like hell but this time the pain wasn’t as severe so through my whimpering, I kept telling him to him to keep going until his **** was buried in me completely. That first time was pure hell but I took the pain until he ******-ed inside me, and this may sound unbelievable but despite the pain from having my virgin a-hole stretched past it’s limit, I began *********** as well! For the rest of the weekend I was Gary’s girlfriend and he ****** me many times, both missionary and doggy and each time it got easier and I began to enjoy it.

 That weekend opened my eyes to an erotic new side of me that I never knew existed.  It’s hard to describe in words how I felt except that I loved being a “Part time” girlfriend for Gary. I loved how I turned him on and I loved pleasing him sexually.  Gary got me into cross dressing back then because he liked girls, so when he started having feelings for me he freaked out and that's how he dealt with it. As for me, I’ve had bisexual feelings since puberty so I adapted very well and so he ****** me regularly for the next few years.

 I really loved the way I looked as a girl. My feminine features stayed with me for a few more years, and Gary loved working with my hair and makeup, and at his request I allowed my hair to grow very long down my back. He was very good at transforming me into a girl. Sometimes he used hot rollers to set my hair in various elaborate hairstyles with any number of assorted hair accessories, but he also loved doing it in more natural looking plain hairstyles with just a hair clip or pretty hair-band or pulled up in a (high) ponytail. Eventually I learned how to do my own hair and makeup (decently) but most of the time he wanted to do it for me. When we were alone I always dressed in feminine clothes (mostly pink or lavender) with accessories that a young girl would have. Gary use to raid his sister's bedroom for everything in the beginning but we both knew that I needed my own wardrobe, makeup and everything else that we were “borrowing” from his sister. So one weekend he decided take me out shopping for girl’s clothes and accessories and with me made up as a girl! I remember that my pressed on fingernails and my toenails were painted with pink nail polish. I dressed in a denim skirt, and a pink girl's tank top with a matching pink belt and sandals. I was also wearing a padded B cup size bra so that I wouldn’t appear to be so flat chest-ed. My makeup was very reserved consisting of eyeliner and just a little blush with some clear lip-gloss and my hair was pulled up high on my head, curled and fastened with a pink hair scrunchie. 

I was so scared venturing out in public for the first time as a girl but as we went into the different clothing stores like fashion bug, The Gap, and Kaufman’s I became more relaxed and confident because nobody was aware that I was really a boy! As we shopped I used the woman's dressing room when trying on different outfits and even used a woman's restroom in one of the department stores! So after a few more shopping expeditions I ended up with a pretty nice wardrobe that I kept hidden at Gary's house. We would still go out shopping like that occasionally but then he started taking me out on dates to restaurants, movies and other places made up like a girl and nobody had a clue what I was!



timjanjon timjanjon
6 Responses Mar 22, 2009

Your story brings back many good memories.

Good for you. You are a lucky girl to have found Gary!

i had a similar experance but my frend in school and i would look at playboys , and jack off , later we m would rub our **** together he would lay on me or i on him and **** each other humping our ***** together , we would suck each others ***** and lick our balls taking turns decribing how we wanted to **** some girl in school or a woman in town. he had a large **** 9' AND MY **** WAS ALMOST 8 t stil think of his great *** load shooting in my mouth and later in my *** .it took a while before we tried it . but it was messy and rarly but ****** each oyher later we started having sex with his younger brother and his little girl frend she loved to get ****** a lot and watch us suck **** and eat *** from her we would spend all saturday in the barn i loved all of us ******* her mmmmmmmmm

Sounds more like a gay thing then a bisexual

Your story really made me horny. Still looking for that first experience. Being horny reading your story must mean I need to follow through and take the leap. Thanks for sharing

Loved the story. thanks for sharing it.