You always remember your first time
Everyone involved is over 18 at the time of the events.
They say you always remember your first time, and that's definitely true for me. Although it was 20 years ago, I can still relive it in my head as clearly as if it happened yesterday.
I didn't really have friends at school until I was around 16, but then found a nice group to hang out with. The two I was closest to were Andy and Michael, and although they had been friends for years they began to include me in most of their hang outs. They were both extremely cool, and they introduced me to drinking, smoking weed and all the usual teenage nonsense. We all lost our virginity within weeks of each other (to girls) and we shared all our secrets. Or nearly all of them, as I never told them that I was bi or that I had a major crush on both of them.
Andy was tall, dark and slim, with bright blue eyes and an infectious grin. He was very popular with the girls, and always had at least one girlfriend on the go. Michael was shorter, with long hair and a mysterious sexy vibe. He had a great body, and loved to show off his six pack whenever he could. Me, I was cute but awkward, I was the smart kid who sucked at sports, but was just about popular enough to get some attention.
One night, not long after I turned 18 (they were both a few months older) we had planned to hang out at Michael's house as his parents were out, but Andy got a last minute date so dropped out. We went ahead without him, which was unusual as we were usually a three. It was also unusual as we had no beer or weed, and I was due to sleep over. We hung out in his tiny room, him sitting on the bed and me on his stool, listening to music and talking about school, who we fancied, and what plans we had for next year. Time passed, it got late and we decided to get ready for bed, with me on a mattress on the floor.
I went out to brush my teeth and when I got back Michael was in t-shirt and boxers, sitting on the stool. I loved his legs, they were nicely muscular and covered in dark hair. I sat on the end of the bed and discreetly enjoyed the view, until he shifted his leg and his dick slipped out the side and into my view. I jumped, he saw me react and realised what had happened, then apologised and went to brush his teeth. I sat there, feeling my dick harden as I replayed the image in my mind, seeing his purple head peeking out from the foreskin, and the thick hair around it. I'd seen people in the changing rooms or urinals in the past, but never so close or so intimately before. My heart was beating so hard, and I could feel it right through me.
I stayed still when he got back, and he sat in the same place. "So, did you want a proper look?" What the hell was happening? He couldn't be serious? I decided to pay safe and do the pretend gay thing. "Hell, yeah!" I responded, sarcastically. "I'm serious," he said, and I could see he was. "I'm kind of hard just thinking about it!" I looked at him, I could see his nerves, and when I glanced down I thought I could see his excitement too. "OK, if you want to?" He stood, and opened the fly of his boxers, pulling his now hard dick out for me to see. The head of his cock was huge and purple, half covered with his foreskin even though he was hard. The shaft was thinner than mine though, and the length around the same, probably 6 inches or so. His dark pubes poked through the gap as well, untrimmed and pretty wild. I stared, I got even harder, and I had no idea what to do next.
He covered up again, and then said "OK, your turn." I hadn't expected this, but I was so hard I just went with it, standing and pulling by shorts down to show my dick. He took a long look, then stood in front of me and brought his out again. They were similar size, but very different shapes, with mine being thicker apart from his mushroom head, and his having more veins. "This is weird," I said as we stood there, "it's so close I could touch it!" "Go on then," he said without hesitation.
I looked in his eyes and he nodded, so I reached out and touched another dick for the first time. I was shocked, it was so smooth, so hot, and felt so heavy. I ran my fingers up and down, and gently rolled his foreskin back and forth for a minute or so. He took hold of my throbbing dick and felt it for a second, but then let go and said, "I'll need to have a wank now" and hopped onto his bed. He pulled his t-shirt up, showing his abs which were covered in fine hair, then slid his boxers down showing me his full bush and heavy balls for the first time. He then nodded again, and I reached out, first stroking the soft fur of his stomach, then running my fingers through his rough pubes and then holding his hard dick again. I started stroking him firmly, up and down for about a minute, feeling him twitch and bounce under me with his pubes tickling my hand with each stroke. Then he said "I'm gonna cum," but pushed my hand away and finished himself off, cumming into his thick pubes, just a small load but he looked very pleased with himself.
I stood there like an idiot with my hard dick still bobbing around as he cleaned himself up, then looked over and said "sorry, I'm not gonna do you," and handed me a tissue to sort myself out. He turned the light off and I lay down on the floor, where it only took me about two strokes before I came in floods. One tissue was not enough, but I figured I could deal with that the next day and passed out.
We never discussed it (until the next time it happened.) It wasn't the best gay experience I've had, but it does hold a special place in my heart.
Happy to follow up with more if anyone is interested?
Posted Mar 14, 2026, 12:33 AM UTC