What follows is a true account of my first homosexual experience. There is a fair amount of build-up in this part, but this will probably not be the case in later sections. If this topic offends you, kindly read another story and do not post derisive comments. Regardless, I hope you enjoy it. Names have been changed.
For the vast duration of my teenage years I had never even considered sexual contact with another man. I had enjoyed the moderate successes with girls that a teenage boy might hope for, making out and more with people at parties and even a few more serious attachments and relationships with the opposite sex. Whilst I was technically a virgin at eighteen, I had done 'everything but' and was fairly set in my ways in viewing girls as the only option for sexual activity. It wasn't that I didn't like the idea of being with a man – I have always had a rather liberal approach to sex - but rather that I just simply hadn't considered it. As the category this story is posted in may suggest however, all this was soon to change.
But first a few words about myself for the purposes of visualisation. I was (and, alas, still am) slightly shorter than average and of a skinny build. My skin is naturally pale and my brown hair is worn fairly long. It wouldn't be unfair to suggest that my general 'look' had been influenced by the bands and artists I so loved; figures such as Alex Turner, Jack White, Bob Dylan, Saul Williams, and so on. I grew up and went to school in the south of England, where many of these stories will be set.
My best friend since I had been about nine years old was a boy named Tom. His mum, at a chance meeting with mine, had suggested that I consider applying for a different school from the one I spent Years One to Four at, where she herself was sending Tom. And so, a few months later, Tom and I met each other at my house as an attempt on the behalves of our mothers to ensure we knew at least one person before we both changed schools. We hit it off immediately and spent the afternoon fighting one another with plastic swords around the house before he was begrudgingly dragged away in the early evening. In our last years as children and through the ravages of puberty we grew to be the closest of friends. While I was quick to discover the joys of chasing girls and drinking at around the age of fourteen (not that shocking in the UK; if anything I was a latecomer), Tom always shied away from the mischievous house parties and attempted pub trips. Notably, he did not seem anywhere near as sex-obsessed as me or any of my other friends. This was something I put down to his somewhat overbearing mother, as well as the fact that he was often seen as a bit of a do-gooder.
By the time we were fifteen, our group of friends had discovered pot as well while Tom was still staying in, nose glued to his books or eyes fastened on whatever video game he was playing. At this point I decided that Tom ought to live a little. Practically forcing him to come to a big party a friend was throwing, I informed him on the journey there that he had to try at least two of the following: weed, alcohol, or making out with a girl. Taking vodka and a quarter of weed, I was resolute that this would happen. Sure enough, Tom got some drink down him and ended up basically being jumped by a girl who saw how handsome he was. Indeed, with his olive skin and dark eyes, Tom had attracted many girls in his time; a fact which frustrated me as he never seemed to take advantage of the fact. Nevertheless, my job was done and I enjoyed the rest of the night confident that I had done a good deed for my friend.
It was around this time that Tom told me in one conversation that he had a secret which he was desperate to tell me, but which he couldn't as it would be unfair on someone else that it involved. Something, though I was unsure what, ticked in my brain and I told him that whatever it was I wouldn't hold it against him. He was my best mate after all. Still, as it would not have been fair on the mysterious other person, Tom kept his lips sealed and I was kept in the dark. He did however thank me for being understanding and promised he would tell me as soon as he could.
The revelation came a few years later. By this point we were both eighteen and now the drinking was entirely legal. Tom had hugely loosened up in his attitudes and we were still as close as ever. One night when we were chatting on MSN or some such thing he wrote:
"Remember I told you I had a big secret?"
"Yeah," I replied.
"I'm gay."
"Oh, that's cool. It's not really a big deal, I don't see you any differently. You're my mate, so don't worry about it."
And so the conversation went on. Though it might well have done, it didn't really come as anything of a surprise. It just kind of made sense. His lack of interest in girls that I had ascribed to his often timid nature hardly made his announcement a surprising one.
Then the penny dropped.
"So, you know how you said your secret involved somebody else..."
It transpired that he had mucked around with one of our mutual friends. Though he only used the ambiguous 'fooled around' and there were no specifics, it was then that something that was completely unexpected happened. I felt my dick straining inside my pants, having rapidly swollen just from the implications of those two ambiguous words. I quickly said my goodbyes and got into bed, but could not get those two words out of my head. 'Fooled around.' 'Fooled around.' It was all I could think, and the more those words and the uncertain images they entailed swum around in my head, the harder my cock grew. The kind of erection that comes to adolescents when they know someone's going to tend to them and will not abate until someone does. I slowly crept my hand down my torso and grasped my dick, for the first time enjoying the sensation of simply holding a penis. At a snail's pace I moved my hand up and then down, savouring each intense moment. Increasing the speed, it was not long before I came a powerful orgasm and shot a large load on my stomach. Immediately I was filled with a sense of shame and confusion at what I had done and went to sleep with conflicting thoughts.
Throughout our friendship I would stay at his house fairly regularly; we would take respite from our otherwise hectic work and social lives by playing copious amounts of video games until his mum would come and shout at us to go to bed, at which point we would merely turn the volume down low. Due to the pressures of sixth form and applications for university, this tradition had sadly died down. That is, until we decided one weekend after he came out to recreate one of our much-loved sleepovers.
His parents were away for the weekend so the setting was perfect. We pretty much spent that Saturday afternoon and evening acting like a couple of kids again. We watched tv, ordered pizzas, took the piss out of each other, and generally had a really good time. When we finally got into bed and turned the lights off it was around one in the morning. At Tom's, I would sleep on the floor on a blow-up bed next to his, and we would talk often for hours about whatever might strike us as interesting.
That night the conversation turned quickly to sex. He was asking me about a girl I had recently been involved with, and how far I went with her. Answering truthfully that though I had gone down on her, she had only ever jacked me off, I felt the conversation naturally head in the direction of a question I wasn't sure if I wanted to ask:
"So, um, how far have you been with a guy?"
I felt a twinge in my pyjamas in anticipation of his response.
