Losing My V: A Bisexual Awakening

A disclaimer before we begin. This story features bisexual content. If that is not for you then you may want to move on.

Most people would tell you that the time they lost their virginity was some of the most awkward and unpleasant sex they had in their lives. Mine was in fact the best. I have chased such sex throughout my entire life. While some of the sex I have had in my life has been incredible, I still to this day have never had sex as mind-blowingly amazing as when I lost my virginity.

I was a late bloomer when it came to sex. While all my friends and schoolmates were popping their cherries anything from thirteen years old, I was still a virgin at eighteen. I'm not sure why I had been so unlucky. Girls described me as cute enough, sometimes even handsome, so I doubt it was my looks that was the problem. Most likely, it had been my shyness that sometimes bordered on socially awkward. The first time I had come close to any form of sexual encounter was on my eighteenth birthday when in a nightclub celebrating the day, I had somehow impressed a twenty-year-old girl enough to be drunkenly making out with her and awkwardly fingering her pussy somewhere in the darkness at the back of the club. That was until the act had caught a bouncer's attention and he had tossed me out of the club by the scruff of my neck like a naughty puppy. Somehow, the bouncer did not see it fit to toss the girl out, and she remained inside the club, along with any chance of getting anywhere further with her.

When it came to my sexuality, I had always been attracted to women. I still remember the first time a girl caught my interest when I was around seven years old watching a late eighties music video with some bikini-clad teenage girl dancing on the beach.

Never had I found men attractive, at least not in the traditional sense. But when shortly after my eighteenth birthday a very close friend of mine -- Aaron -- had caught himself embroiled in some rumour mill where another friend had claimed they had dropped by his home, peered through the window and caught him being fucked by another guy on the living room floor. Eventually, the rumours shifted and took many forms, and Aaron was soon the laughingstock of our sixth form college.

For the longest time, I had assumed the rumours were false. It wasn't long before Aaron and I found ourselves taking advantage of our now legal status to have a drink in the pub. It was there that in his inebriation he confessed to me that the other guy -- Greg -- had raped him. Greg, however, was accusing Aaron of raping him instead. Either way, something about their stories didn't add up. Neither of them was particularly distressed about it all. Though the whole college knew about it, there was no involvement from any police or tutors and neither parent showed face over the situation. After a while I had begun to realise that they had been deflecting the revelation of their homosexuality with accusations of rape, and soon enough the whole affair was all being swept under the rug as soon as the truth had been revealed.

After the confession and subsequent realisation of my friend's sexuality, the thoughts of having sex with other guys began to emerge within me. I had never had the thoughts before, so I'm not sure where they had come from. My mind was like a mountain suddenly erupting with deeply buried lava and revealing it was a volcano all along. My every waking thought was constantly flooded with the images of Aaron on all fours with Greg behind pushing his cock deep inside my friend's arse. I masturbated repeatedly picturing Aaron's cock swinging around as he bounced up and down in Greg's lap, or the two of them lying in a sixty-nine swallowing each other into the back of their throats.

One evening when Aaron was staying over, we had watched some trashy sex-ridden teen movie. I thought I would test the waters with him and announce that a sex scene in the movie was making me horny. I told him that I wanted to jerk off right there. He boldly told me to "go ahead" but for some reason I couldn't do it. I still wonder to this day what would have happened if I had gone ahead and pulled my cock out to get myself off only a few feet away from him. Would Aaron have done the same? Would have I been bold enough to ask him if I could suck him?

With my interest in sex with men piqued, I spent the next couple of months trying to arrange something online with anonymous older men. This was when the internet was still particularly young, and chat rooms with plenty of predatory occupants and very little policing were all the rage. I had sent many a message to different strangers and received many in return. A couple of times, I had organised to meet some of the men with promises of them being fellated by a handsome and supple eighteen-year-old. One of those times I arrived at the designated meeting point -- a fountain in the busy town square -- and watched from afar to see who turned up before fully committing. The only man that arrived and waited was a scruffy fifty to sixty-year-old who, in retrospect, looked like the exact stereotype of the sexual predators you would see on the news. It did not appeal to me in the slightest. Needless to say, I did not feel inclined to introduce myself. Another time, I found myself being bolder and was the one who waited by the fountain. To my disappointment it was me who was stood up that time.

Following that, I resorted back to chasing girls instead though the fantasies of men did not abate during that time. When I obtained my first debit card, I used the wages from my part time job to order dildos and buttplugs of various sizes to train my arsehole for the cocks that I desired inside me. Each time my mother had left me at home by myself, I would fuck myself with them while jerking off to bisexual porn. Sometimes I would vigorously ride various rubber cocks in full view of the living room window secretly hoping that Aaron would visit and catch me in the same way that he had been caught.

Around that time, I finally managed to get a girlfriend for just a few months. Katie was younger than I and not yet ready for sex. Before long, my increasing sexual desires had driven her away, so my cherry was preserved a little while longer. Still, we remained close friends, and shortly after that she became the first person that I confessed my secrets to.

Eventually, I found myself still a horny eighteen-year-old virgin who in a couple of months was due to finish college and go to university. A few weeks after that I would be turning nineteen. I could not allow myself to be a virgin by that point.

That was when I discovered Adult Friend Finder. As far as I am aware, this website still exists in some form, at least at the point of writing this. Back then, it was the main, and perhaps only, hook-up website where you could add a profile, swap naughty pictures and -- provided you paid a subscription -- chat to other users and arrange to meet up purely for sex.

It was the couples that I had put the most effort in attempting to contact. With a couple I could hope to experience both desires that I had spent the past year fantasizing about. I had also sent some messages to single men and women, never once mentioning that I was a virgin for fear of scaring them away with my inexperience.

Some responded and gained my curiosity. One woman asked me to chat to her over webcam -- and once her camera was switched on it was apparent that she was not a woman at all, nor even trying to be. I would have not particularly cared about the forty-year-old guy stroking himself at the other side of the camera. I might have even entertained it and partaken in a little mutual masturbation had he had been straight with me to begin with.

Later, the male partner of a couple seeking a third to join them sent me a photograph of his girlfriend. As part of the test to see if I was right for them, he asked me to take a picture of me jerking off and ejaculating over the image. I obliged and sent him a picture of her photograph printed on A4 paper and covered in semen. Soon after the guy messaged me back admitting that he was not part of a couple after all, and just liked to send his ex-girlfriend pictures of her covered in other men's cum.

I had all but given up on the site, but then I received a message from a girl who claimed to be part of a young couple looking for a man of a similar age to join them in having some fun and exploring their bi side. I explained that I had been burned by other users before, so she sent me pictures of themselves holding personalised messages with the date and my username, along with other photographs for my pleasure.

The girl, Claire, was a cute petite thing, nineteen years old with a blonde ponytail, pale skin and a slim but buxom body. She was naked in one of the pictures and proudly displayed a neatly trimmed mound of wispy blonde pubic hair and ample tits clasped in her hands.

Anthony, the male half, was slightly older at twenty-two. He had short and spikey bleached blonde hair with a toned body and lightly freckled skin. I did not find him particularly attractive, nor unattractive, but then I never did base my interest in men on their appearance. Luckily, they included a picture of his cock for good measure, and it stood hard at six inches or so. It wasn't particularly impressive, and my own cock would have dwarfed his. Regardless, I wanted it inside me, and I desperately wanted to share it with the cute girl in the pictures.

I told Katie of the couple's interest in me, and she encouraged me to meet them. She knew how the fantasies had plagued my mind and clouded my judgement. They were the reason I had pressed her so much on having sex back when we were dating after all. She said it was better to get it over and done with. That way I could get it all out of my system, and maybe then I might be able to understand and accept what I was, and move on in whichever direction the realisation would lead me in. It might not come as a surprise that Katie grew up to be a therapist.

A few weeks followed where we communicated numerous times a day, telling stories of what we wanted to do to each other, and sending naughty pictures back and forth. Back then I only had limited access to my mother's digital camera, so in order to send some of the photographs I had to take them on my classic film camera, have the film developed, scan them into the computer and send them by email. I looked somewhat young for my age, and some of the photographs of what could have been confused for a teenage boy holding an engorged cock did not make it back from the developers. In return they sent me pictures of them fucking doggy style and of Claire on her knees with the head of Anthony's cock resting playfully against her tongue. In each picture she had a wanton look of desire in her eyes that I still can't forget to this day.

Eventually it was August, a few weeks before I was due to start university and I found myself on a train on the way to meet them. I can still remember the anticipation I was feeling, and the unbridled nervousness about being disappointed one more time. When I arrived at their local train station, they were not there waiting for me. An hour passed, and after numerous texts and calls them to no avail, I had nearly given up and booked a return ticket home. But then I received a message that melted all the disappointment away. It was an apology from Claire saying they had gotten my arrival time wrong and were now on their way to pick me up.

It is now nearly twenty years since this all took place, and much of what happened was fuelled by alcohol and other substances, so I only have a vague recollection of what led up to the antics of the next morning. I remember the initial meeting at the train station being somewhat awkward but eventually we warmed to each other over a meal. Then we went out to drink and, due to my babyish facial features, I remember my ID being requested by the bouncers at all three different bars and pubs that we visited. They sensed my embarrassment every time and began to reassure me with compliments about being cute and proclamations that my cock certainly didn't look underage. At the third bar, Claire received a phone call from a friend where she was invited to a rave in and old converted warehouse on the outskirts of town. Nineties dance and electronica being my preferred genre of music, I was ecstatic at the opportunity to attend such an event, and the evening became less about that the anticipation that we were meeting to eventually have sex, and more about just having a great night together.

At the rave, we met Claire's friends, two young and pretty girls that I cannot remember the names of who immediately offered us ecstasy. I had only ever smoked a little weed at that point, so that alone would be a new experience for me. Eager to fit in, I accepted and hesitantly threw the pill back into my throat. Then one of them offered me amyl nitrate; "poppers" she had called it. She claimed it would not only get me "super high", but also relax my arsehole, as if she had expected something to happen between Anthony and I later. I obliged further, and before long we were dancing and grinding up against each other, blissfully unaware of anything other than the music and the five of us. Anthony and Claire both grabbed me to kiss me on the dance floor, and I welcomed it and kissed back, moving from Claire's lips to Anthony's and then back to Claire's. I even made out with Claire's friends before being dragged back to make out some more with the couple that I was actually there for. There I was, inexperienced, horny and high, making out with and having my cock caressed by three beautiful women and a man. I was in heaven.

The rave ended at around 2am, and the five of us left for a house party being held by friends of Anthony. We stopped there only for a short while, and eventually left, leaving Claire's friends there, to take one of Anthony's much older male friends -- Bunny they had called him -- back to his house. We stopped there for a brief time to refuel on coffee, during which time Bunny decided to drop his hand into my lap and rub at my cock through my jeans. I cannot deny that I was intrigued where it was going, and my cock stiffened against his palm, but Anthony and Claire had other plans for me. They told him to stop teasing me and we shortly left after to head for a Holiday Inn.

I never did understand why they had opted to stay at a hotel; maybe neither of them had a place of their own and they lived with family members or housemates, or maybe they simply did not trust a stranger in their own home. I remember it was light out, so I expect it was around 5-6am by the time we had fully checked in. I also remember the disapproving look on the receptionist's face as she attempted to ascertain that we, two men and a girl, were sure that we wanted to book a single double-bed room at such early hours of the morning. It was clear what the room was intended for, and Anthony made sure to reinforce her suspicion by opting for a late checkout because "we were going to take longer than that".

We had barely stepped foot into the room when Claire launched herself on me. Her lips pressed against mine as Anthony moved close into our sides, wrapping his arm around our waists and intently watched us make out. She broke from my lips to kiss her boyfriend's instead. I watched their tongue's dance slowly around each other while my cock pressed firmly against her stomach, aching and desperate to be freed. When their kiss ended, she took his face in her fingers and guided him to my lips instead. While I had already kissed him earlier, it had then been fuelled by the ecstasy. Now my mind was becoming somewhat clearer, and it was only then I paid attention to how it felt to kiss another man. It was much firmer than her delicate and soft kisses, and I remember his stubble tickling against my chin.

The three of us stumbled back into the room towards the bed, passing our kisses back and forth and occasionally trying to press all three sets of lips and tongues together to awkwardly make out with each other at the same time. Claire fumbled wildly at our jeans while Anthony and I kissed again, and before long she was yanking my jeans down to my feet and freeing my swollen prick. I still remember the guttural groan of delight that escaped her lips as she saw it bounce to life. I felt a hand wrap around my cock, and it was only when I saw that Claire was now pulling her boyfriend's jeans down with both hands that I realised it was Anthony's hand around me. He was slowly tugging at my length while his tongue circled mine.

Claire was now on her knees before us, still tugging Anthony's boxers to the ground and groaning again when his firm cock leapt into view. Anthony's lips parted from mine, and he wrapped his hand into his girlfriend's hair. One hand urged her forward while the other guided my cock towards her face. Finally, it was happening, I was minutes away from having sex, and with both a man and a woman at the same time. I was torn between the sight of this gorgeous young girl approaching my cock with hungry lips, and the view of his beautiful cock just to her side. I couldn't believe it.

I was very skinny back then, and my cock had not yet lost a couple of inches due to age and being swallowed by weight gain. Of course, I had measured it as a teenager, and was very pleased that it stood at 8.8 inches when fully erect. Regardless, I had always desired for more girth, and always felt some anxiety that my long but thin cock would still not satisfy anyone. It was the first of a few proud moments of my life where a sexual partner had loudly commented on the size of it during the act.

"Shit, this is big," she had said as she wrapped her fingers around the base of it.

Part of me felt relief, maybe my cock was impressive after all, but another part had felt bad for Anthony. The excitement she displayed clearly stemmed from him having such an average dick. But they had known my size the whole time we had communicated throughout the past few weeks. They had seen pictures of it (at least those that made it back from the photo developers), and he had even said himself that he "looked forward to her playing with my big prick". In hindsight, I think maybe that had been the fantasy all along; the bigger the cock they could get for her the better. If my cock hadn't have appealed so much to them, maybe I would never have met them in the first place.

The first lap of her tongue against the swollen head of my cock sent a wave of pleasure through me that washed away any hesitation. I was oozing pre-cum, and she showed no sign of it tasting too unpleasant as her boyfriend massaged the head against her swirling tongue. She was soon stretching her lips around me and welcoming me into her warm mouth. I gazed down at her, moaning heavily as she pushed herself down my length as best as she could, struggling to take me too far into her tiny throat. Each time my cock proved a little too much for her to take and caused her to gag, she would jerk her head back to catch her breath and then push on, pressing down even further and further until she finally found her true limit. With the guidance of Anthony's grasp on her hair, she was soon bobbing her head up and down along my cock without too much difficulty, eager to pleasure the both of us.

In hindsight, I have had better blow jobs since, but this was my first, and I will never forget it. It was the kind of blow job I expected only ever happened in the porn that I had spent my teenage years watching. It was sloppy and lustful, even aggressively so. With one hand gripping firmly at the base of my cock, and the other digging its fingernails into my thigh, she continued to fuck me with her mouth unabashedly. She moaned loudly around my prick, and saliva poured from her lips to the floor. Her tongue danced around the underside of my shaft and teased my frenulum as it slid back out.