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The first time my cock was ever in a guys ass bareback was only for a few seconds when I was 20. I had gone home with an 18-year-old twink and after we were naked I was lying on this couch and he straddled my cock and lowered himself on to my bare cock. (No lube, it was pretty impressive.) I was, of course, paranoid about STDs so I asked him for a condom. Still ended up being a great fuck but I do regret asking for that condom. The next time was about a year later with the guy who would become my boyfriend. The first time we had anal sex we had been jerking off with lube and then he just sat down on my cock and started to ride me. I ended up shooting my first bareback load in him that night. A couple years later, we had never used condoms when I was fucking him. We had great sex with simultaneous orgasms and I always shot my load in him. He mostly bottomed. We occasionally had 3-ways but they were always with condoms. My boyfriend had a great slender, yet muscular body, and guys were always after him. One night we got chatting with this muscle stud and ended up going back to his hotel with him. We all got hot and heavy and started making out and stripping and we found out this stud had a massive 9 inch cock. The stud asked us which of us usually fucked the other and when we told him he wanted to see me fuck my bf. My bf wasn't really feeling it from me because I could tell he wanted this stud to fuck his brains out and let the guy know. My bf asked if the stud had condoms but he didn't, so my bf asked for his hotel keycard so he could go pick up some condoms so this hot muscle stud could fuck him. The stud looked around but for whatever reason couldn't find the keycard in the pile of all our clothes on the floor of the hotel room. Having failed at that, we all started jerking and sucking and making out. At one point, i was laying on my back and my bf was laying face down with hot muscle stud laying on top of him. I was making out with him as he was jerking me off and grinding his cock against my boyfriend's ass crack. At one point both the muscle stud and my bf became kinda still. I had a hunch and reached between the muscle studs legs to feel his cock. All 9 inches were buried bareback balls deep in my boyfriend's ass. I almost had a spontaneous orgasm. Normally my bf insisted on condoms with other guys, but this muscle stud was fucking hot. I knew what was happening but I whispered to my bf "is he in you?" My bf said "fuck it" and flipped the muscle stud over on his back and sat down on his cock again. He rode him for a couple minutes while jerking off and eventually shot his load on muscle stud's stomach. He got off the stud and I scooped up my boyfriend's load, smeared it on the stud's cock and sat my own ass down on his huge cock. I whispered in his ear to breed me and he said okay. It only took me a couple a minutes to blow one of the biggest loads of my life over this guys stomach, and a few moments later I felt him sigh as he unloaded deep in my ass. We got dressed a few minutes later and went home. When I took my underwear off to go to bed I could see where a bit of his cum had leaked out of my ass. Every guy we fucked was bareback after that.

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.