The first time I took it raw was with a guy I had hooked up with a bunch of times before, mostly for oral, but we did anal with a condom before.
Anyway he came over my place and we exchanged oral a couple of times making each other really hard, and he ate my ass which drives me crazy. After he ate my ass he got up between my legs and said he wanted to tease my ass with his cock a little bit.
Now having hooked up with this guy quite a few times before I had no reason to think he'd try anything, but after "teasing" my tight ass for a few seconds he pushed forward and rammed his cock balls deep in my ass. I remember my eyes popping open when I realized what he had done and that his raw cock was in me, then I just moaned and told him to fuck me. The rest of the night we fucked bareback, and I even took him ass to mouth a couple of times and rode him too.
The only thing that disappointed me was that he didn't buy breed me when he came, he gave me a facial instead. But I did suck his cock clean and I ate all the cum from my face as well.
That was was my first time taking it raw, it wasn't planned, but it was hot. How about yours, planned or unplanned?
