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.