Back in my early teens I had a close friend that I experimented with. I don't know if he knew then he was gay but he eventually came out of the closet and all and since I was straight, I always felt a little strange about the stuff we did but it was so erotic and felt good I went with it, which would then lead to trying other things in time. He lived by a lake and they had a dock that you pretty much had to walk this wooded trail to get to and it was pretty secluded, so sometimes late at night we'd sneak down to do a little skinny dipping. Sometimes we jerked off, other times he would jerk me off then himself (all under the water), whatever. Now here I should mention that we had really opposite cocks. Mine was very long and relatively thin. His was short and thick. You could say we were both pretty hung but mine was just long, he had the girth.

I don't know exactly how it happened, or just don't remember to be more accurate, but at some point while we were both hard he backed into me and not only did my long cock slide up between his cheeks, the tip rested right against his asshole. As often when we do things (because we were younger and nervous someone would hear us or something) we didn't say a word, just sat there a second. I was raging hard from jerking and I could feel the heat of his ass radiating heat against the tip of my dick. And then he pushed back and started taking my cock up his ass. I had to be the first thing up there because it was soooo tight that by the time he reached my balls, I started to cum. I grabbed his hips and I pulled him as hard on my cock as I could as the orgasm built to bursting and then I released a massive load into his tight little ass while loudly moaning "Fuck I'm coming" into his back. He said "Me, too." and I could feel him beating off and then his own orgasm rack through his body.

We cleaned up in the lake but my erection didn't fade. My friend was on the beach on his hands and knees gathering stuff up and I noticed he hadn't put his shorts on yet so I came up behind him, pushed him onto his stomach as I climbed onto his back, put it in and started fucking his ass again. Several minutes into it and a string of grunts and "oh Gods" from my friend he tells me he's coming again. He came from me fucking his ass. I finally finish and have another intense orgasm. "You must really like that ass" he mutters. I fucked that ass for two more hours that night. I'm certain I'm the reason my friend is a bottom in his relationship.

We fucked all through high school regardless of if we had relationships or whatever. After he started giving me blowjobs I didn't fuck his ass so much because all the clean up was done with his mouth and it was much easier. After school we didn't hang out much and eventually we drifted apart, only talking once or twice a year, if that.