My first time bottoming bareback was also my first time bottoming.  I'd met a guy and we'd played around a few times with me topping him.  He never asked for, nor provided a condom, so I got to top raw for the first time with him.  It was fantastic, and he offered to top me.  Since i had never done it before, I declined each time.  After a few months, I decided to to finally give in and bottom for the first time as well.  When I said yes, it was a simple transition to him fucking me, and condoms were never discussed or offered.  It was simply raw fucking, straight up.  I bottomed for him, and when he got close, he pulled out and came in my mouth.  We fucked a few more times before I moved away, bare, but never being bred.  I finally took the plunge and was bred for the first time this past winter.  And regret that I wasted so much time having my top pull out and shoot in my mouth or on my back.  Those loads should have gone deep inside my ass.