I had already taken a cock bareback, but the guy pulled out before he came. I had been fucked a couple times before that by guys wearing condoms, and it was fine, but it didn't really do much for me. I got off, but it wasn't anything to write home about.

The first time a guy actually came in me was the first time I really got the appeal of bottoming. I was 21 at the time and we met on an AOL chat room (late 90s, lol) and I agreed to meet him at his place. He was a fit twink just a little taller than me. We had coffee and chatted for a while in his bedroom and eventually moved on to kissing. He stripped of my clothes and went down on me for a bit and then I turned around and started stripping him off. As I slid his underwear off I realized his cock had to be close to 8 inches long. It wasn't what I would call too thick but it had a nice girth to it. I sucked him for a little bit and then he pulled me up to make out some more, rubbing our cocks together.

I sat up on his legs and started stroking his cock and he did the same with mine. After a minute or so he asked me if I wanted some lube and I said yes. He added some lube to our hands and we went back to slowly stroking each other. After another couple minutes he pulled me down to kiss him, and I had to scoot up his body so my ass was just over his crotch. I had to reach behind me to keep stroking his cock. It was basically at my ass crack so I started rubbing the head of his cock on my crack while stroking the base and his balls. I kept kissing him as he started slowly thrusting his cock up and down my ass crack. His cock got progressively lower and lower down my crack until he was thrusting against my hole. I couldn't help relax my hole just enough for the tip to start pushing through with each thrust. I knew I should've asked him for a condom but I was just so fucking horny I let the tip of his cock keep poking a little deeper into my hole.

Finally, as he was thrusting up I sat back just enough for the head of his cock to slip past my sphincter. It didn't hurt, I just had a full feeling in my ass. He stopped thrusting, I guess he wasn't sure if he should keep going with out a condom, but I just slowly lowered my ass onto the rest of his cock. I bottomed out on his cock and then just started to ride him. His cock was rubbing my prostate in just the right way, and I felt an orgasm building. I had stopped jerking myself off and was just riding him. After a couple of minutes he said he was about to come and I told him to do it, and he started moaning as he thrust his load deep in my ass. I kept riding him, and about 30 seconds later, without even touching my cock, I had my first hands-free orgasm and I shot my load all over his stomach. After I finished his cock felt massive in me and started to get a bit uncomfortable so I slowly lifted myself off of him, and a bit of his load leaked out of my ass onto him.

I didn't bottom for a while after that as I had started dating a guy that was mostly a bottom.