I remember the first time I bred a guy. I had had condom sex before and had all the intentions in the world to have that with this guy. I had met this guy in the AOL chat room of all things. He was like 3 years younger than me. Went to his dorm room and we watched some porn. He was cute, shaved head, nice smooth body. We jacked off together to the porn and he asked me if I wanted to use a toy on his ass. Of course I said yes. So, I'm working his ass over with this dildo and he's definitely into it a lot. I'm hard as a rock of course. In addition to the dildo I'm using my fingers and I am getting more and more excited. So, I tell him I am going to fuck him and he sounds VERY eager at this point. Normally, I would've grabbed the condom at that point but I say to him "I'm just going to stick it in for just a second to see what it feels like, then I'll put on a condom" and he says "that's not necessary". At this point, I'm still totally decided that I'll use a condom but I also really want to feel his hole on my dick after I just played with it for like 10 minutes with my fingers and that dildo. So, I stick it in, intending that to be just for a sec. Well, as soon as I put it in, he starts saying stuff like "oh god, fuck me harder" etc. I just think to myself, fuck it, and that's what I did. Since I'd never barebacked before I get close pretty quick and I tell him I'm going to cum soon expecting him to ask me to pull out. No, he goes on "yeah, shoot your load in my filthy asshole, breed me good, shoot it". Well, that put me over the top of course and I blast a gigantic load into his ass. Clearly, this wasn't the first time this boy got bred but I didn't really know much about BB sex back then. I still remember how satisfying it felt to claim ownership of his smooth ass.
It wasn't the last time we fucked and we got together for a few other things like WS after that. He was younger than me but I learned a few things from him. Last I heard he was still a bottom slut (for all I know he's somewhere on this site LOL) but I think he eventually converted whereas I (total top still) am still neg. I'd still do him today though for old times' sake.