Originally intended to be safe, but he ended up convincing me otherwise. Much older guy, ate my ass and had me on the edge of the bed fingering my hole with my legs in the air. Next thing I know he pulls his fingers out and slowly slides his cock in to replace them before I could object. I remind him I wanted to use a condom and he said "don't worry I was just messing around" and smirked at me as he slid a little in further making me moan involuntarily before taking his cock back out.
He put the condom on and reinserted and fucked me for a short bit before asking "just doesn't feel the same though, does it?" and I'd just been thinking the same thing. He ended up convincing me to take it off myself - as he pulled out I slid the condom off his cock before he slid it back in. Fuck... the rush as he popped the head in and looked me in the eyes as he slid in all the way until his hips were pressing against my ass as we moaned together. It wasn't long after until he asked if I was ready for his load and it didn't even feel like myself when I said "fuck yeah, give it to me" before he slammed into me and I felt his cock spasming.
Let's just say I've been hooked since, lol.