I remember the first time. Late at night, prep school pal in NJ. Late-night skinny-dipping in the pool. We sat around naked afterwards and we both got big hard-ons. He had seen me naked at school, so he knew I was big, but he'd never seen me hard before. I'd swapped blow jobs before, so I started in to blow him. His dick was rock-hard. He had a hairy crotch and ass for a high-school senior.
I looked at his asshole, and I was fascinated. First time rimming, which he loved. I pushed the head of my cock at his hole, but I was too big. He blew me for a while. Then he spit on his thin cock and pretty much jammed it in my ass. Hurt. He was a good fucker, surprisingly, and I began to love it. A lot. I jacked off while he fucked me and came. He came in my mouth. Bliss.
I never fucked him, but I did fuck his older brother in college, which was odd.
I've fucked a couple of guys for their first time, but they really have to be into it. Lots of rimming, lots of lube, lots finger-fucking. Slow and easy, I say, and I do take no for an answer.