This was about 1992 when I was 28. I had hooked up with an older (40ish) hispanic guy through a personal ad in the weekly alternative paper. I was quite a condom nazi at the time, but my guard was down because this hook up was just supposed to be oral. I had posted an ad for guys looking to fuck my face because I was really into that at the time.
This guy was a total top, and he could tell I was a total bottom. We started out with him on the couch with me between his knees blowing his uncut, thick 8 incher. He was a smooth and knew what he wanted. Before I knew it, we had switched places. I was on the couch with my legs in the air, and he was between my knees with his tongue up my hole. Now remember this guy had a big cock. Even though I loved getting fucked, it usually took lots of lube and a slow entry for me to take a big one. Somehow he had my hole so opened up and slick with his spit that he slipped his cock all the way in my hole bareback in one smooth motion.
It felt so good. Even though I was freaking out, I let him fuck me bare for a few minutes. Then I totally freaked. He was cool. He grudgingly put on a rubber and finished that way. He came back for seconds a week or so later and was nice enough about wearing a rubber although he asked about going bare. The third time we met though he invited me to his place.
Just like he had done the first two times, he spent a long time eating my hole. This time though, he had a bottle of poppers handy. I kept sniffing them as he ate me out. When he reached for a condom, I asked him to please go bare. He smiled really big and told me he had been waiting to here me say that. He slid that big piece into me and a few minutes later gave me the first load I had taken in many years.
He and I were fuck buddies for years. At first I was only bare with him, but soon I started asking other guys to go bare. Within a few years though, I was bareback all of the time.