Tom Tops Me Ch. 01

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Teen's first gay experiences.
2.4k words
4.49
51.1k
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Part 1 of the 2 part series

Updated 06/14/2023
Created 05/14/2012
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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.

He answered that he had been sucked off by guys and sucked them off himself. It was lucky the lights were off and I was under a duvet or else he would have seen the tent in my pyjamas where the all too familiar persistent erection had formed. Hearing him talk about his various escapades turned me on to no end. I found myself trying to touch my dick in the most subtle way possible. My whole being seemed to ache for sexual release and I clutched my cock in an attempt to give that. I knew that I couldn't just jack off right there, but I also knew that I couldn't cope with being this aroused.

So I asked him more, and the more he told me, the more my body needed me to cum. It was no longer listening to reason, but was running wild and leaving what might have been my normal thoughts far behind. Eventually I could take it no longer and, cock still in hand under the covers, I asked him nervously:

"Could we... you know... experiment a bit? It's not like I'm..."

Before I could falteringly justify my proposition he got off his bed and sat next to me.

"Are you sure you want to do this?" he said, turning a bedside light on.

I nodded my agreement.

Without saying anything more he peeled the duvet cover away from me. A slight smile formed on his face as he saw I was already incredibly hard. A wet patch from all the precum was visible on my shorts. I blushed from how obvious it was that I needed this. With one hand he pulled them down, exposing my cock. From the second his hand gently touched my dick, I was in paradise. His fingers clasped around it and his hand stayed still for a moment. Then he slowly stroked down, pulling my foreskin back. I let out a moan. He smiled.

He ramped up the speed, occasionally twisting his hand expertly, knowing what effect this was having on me. I had never seen as much precum on my dick as I did then, only enhancing the sensations I was feeling. Girls had jerked me off before, but here was someone who clearly knew how a dick worked. Each stroke was a ripple of pleasure through my body. My eyes closed and my head rolled back.

He let go for a short moment and I looked to him, just in time to see him lick the tip of my penis. He then worked his tongue around the head and then dragged it down my shaft to the balls. He was a master. A few licks later he took the head into his mouth and I felt his tongue swirl around it once more. As he pushed his head down further, I watched my dick as it disappeared into Tom's mouth. Feeling his lips clasped round my penis brought me even closer to my immanent orgasm.

It took about a minute of his head bobbing up and down before I could hold on no longer. I moaned loudly as a fierce orgasm shook me. He kept on sucking as my cock contracted, and not one drop left his mouth. I lay there feeling lightheaded.

"Your cock is tasty," was all he said.

I smiled and sat up, before realizing what I now wanted.

"Can I..."

"Yes," he said, interrupting the silence I had left.

He sat on the edge of his bed and pulled his pants down. His erect dick can only be described as magnificent. It was around eight and a half inches with a very decent girth, compared to my thoroughly average cock. I knew immediately I wasn't going to be getting it all in my mouth, but couldn't help but admire it. It was olive-coloured like the rest of him and the head looked particularly impressive with a few drops of precum glistening upon it. From the position on my knees it looked daunting, yet also inviting.

I reached out my hand and tentatively touched it, wrapping my fingers around the middle of the large cock in front of me. It felt right in my hand. Hard, but with very soft skin. I was entranced. I stroked it only very few times before I myself was hard again.

I decided to waste no time and licked some of the precum from his bell-end while stroking his cock. He gasped in appreciation. Mirroring his technique, I then licked down the considerable length of his cock. All the while the smell and the nature of the situation were driving me mad. Taking the next step I put his large dickhead in my mouth, savouring the taste of my first ever blowjob. I managed to take about half of his penis on my first attempt, and so built a rhythm with my mouth of going this far down while my hand worked on the lower half. My free hand was now frantically jacking off my own cock.

This continued for about five minutes until I took both hands from their respective dicks and focused on my mouth. Twisting my tongue round his cock while sucking him as he had done to me I was incredibly aroused. I put my right hand back to him again, but was amazed to find myself spewing cum on the floor from my dick without any stimulation. My knees buckled slightly from the pleasure and all but a quarter of his shaft entered my mouth.

Sensing the state I was in, Tom took his cock from my mouth and stroked it ferociously himself before plunging it back in to the three quarter's depth. Hot sperm flooded my already full mouth. I did manage to swallow the first few waves, but then the cum started to seep from around his dick and out of my mouth. I pulled off and lay back on my bad, practically passing out with Tom's sperm dribbling down my chin.

All I knew as I drifted off to sleep was that my friendship with Tom had just been taken to an entirely different level.

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nategraynategrayabout 1 year agoAuthor

Part 2 pending publishing, only a decade late!

drabidrabiabout 2 years ago

Yes, we really need more!

AnonymousAnonymousabout 6 years ago
Hot

Hot Best Mate/Buddy first time story. Looking forward to reading more!

AnonymousAnonymousalmost 8 years ago
☆☆☆☆☆- (4.55/5.0 = 91% = A)

:-)

AnonymousAnonymousabout 8 years ago
More?

Where are the subsequent chapters?

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