I once hooked up with a French guy who mainly played safe. He didn't have insurance yet since he was on probation at his job and was cautious since treatment for anything would be out-of-pocket. He also wasn't on PrEP but I was. I hooked up with him once before and we wrapped up. I liked him since his dick was pretty nice and he looked a bit like a sexier version of my previous boss. The second time, he agreed that he was willing to fuck me bare and I was excited. When I showed up, we teased a bit and he put it into me to try. After around maybe a minute of really soft fucking, he changed his mind and asked if I was okay if he wrapped up. I was disappointed, but I respect his choices. We fucked for a while, maybe like 15 minutes in his room before he asked if he can fuck me in his kitchen over the counter. I was okay with it and assumed it was a bit of a kink of his.
When he got close in the kitchen, I told him to "cum in me." I assumed he was going to cum into the condom, but to my surprise, he took the condom off, put his bareback cock back into me and pumped maybe 2 or 3 more times before breeding me deep. I was so hot and excited, my ass clenched, and milked out his load. I was afraid it might have been painfully tight from how much I was holding onto him. When he pulled out, the moment I felt that skin-on-skin, cum-lubed hole, I was moaning and in heaven.
We then had a nice dinner that he made and talked a bit about his reluctance. We never did end up hooking up again, but I'm satisfied with what happened. I'm hoping that his insurance kicked in and he felt more comfortable fucking raw because he seemed to enjoy filling me with his babies.