Where it happened: His room
When I was in high school, it was becoming clear that my best friend was starting to like boys as well as girls. It didn’t bother me, we’d still talk about our crushes and fantasies, just his involved guys sometimes. We had always masturbated together (separately) when we’d sleep over, but he never tried anything with me, because I liked girls only. Then one night we were jerking off with the lights on and decided to let each other have a good look. It was weird but sort of interesting to see another guy’s erect penis, and let him look at mine. (It was also kind of reassuring to see that we were similar sizes.) Another time on a camping trip, he convinced me to let him try jerking me off, but it felt weird, especially when I tried touching his penis for just a second, and we didn’t go anywhere with it.
Then one night when we were 16, I was sleeping over at his place. He was about to leave for an extended trip, so it was our last chance to hang out for awhile. We lay there in the dark, he on his bed and me on the floor in a sleeping bag, both of us masturbating and talking about sex, which I’d never had, and he claimed to have (not reliably, it turned out). I was curious and asking questions about blow jobs, till finally he said, “If I asked you, would you let me?” which I guess had been the point all along.
I said I didn’t know, I was really nervous and horny and I really wanted to but also really didn’t. But he kind of made up my mind for both of us. He asked where I wanted to do it, I said right here on the floor. So I took off my underwear and lay naked on the sleeping bag, and he got down on the floor with me. I felt his hand touch my penis, and then it was surrounded by warmth and wetness and I knew without a doubt that my penis was in his mouth. I felt his tongue sliding up and down the shaft and around the head, it wasn’t exactly what I’d expected but it felt really good. At first I was so nervous I was trembling, but soon I was able to relax and enjoy my first blowjob.
We kept at it for a long time, him alternating using his mouth and his hand on my penis. After awhile, I told him that his blowjob felt really good, but I didn’t think it was gonna make me come. So I lay down on the bed, he put some suntan oil on his hand and stood next to the bed, his hand sliding up and down my hard penis. At this point, being totally into it, I wanted to touch him too. So he took off his underwear and stood there, totally erect, wearing just a t-shirt. He continued masturbating me while I fondled and stroked and caressed his penis. It felt really good in my hand, and soon I came all over his hand. I cleaned up, put my underwear back on, and watched as he finished himself off.
We never had a repeat of this incident until we were both in college. We’d both been at a party when everyone was home for Thanksgiving break, and he was giving me a ride home. The topic of our one incident came up, and we agreed that we wanted to do it again, so he found a quiet spot in the woods to pull over. We got in the back seat and I pulled my jeans down, I was so excited to be doing something that seemed so taboo to me. And once again I felt his mouth on me. I was much more eager to feel his erect penis this time, and after a few minutes of him sucking me, I knew I had to try it too. And of course he was fine with that. I knelt on the floor of the car and, without giving myself a chance to hesitate, put his penis in my mouth. It felt good sliding my tongue up and down, licking the tip and tasting his pre-cum. He said I was really good at it, and it took only a couple of minutes till he let me go and got himself off by hand.
A year or so later, we had one final session where we 69ed for a long time, and he finally got me off with his hand like before. Since then, I’ve only had sexual contact with women, though I often think of these times and I’d like to do it again. My fiancee knows all about this bit of my past, and she finds it pretty hot. Maybe one day we’ll find someone, or better yet, a couple, who’d like to join us.