I caught up with my buddy Chet, to talk about sex and his experiences of anal sex. Chet has to remain anonymous for this interview due to the nature of his work.

Who was the first guy that fucked you?

He was my college boyfriend.

We were house-sitting for some of my friends. and that’s when we took the plunge, so to speak, into anal sex. It was a mutual thing.

Was the reality of getting fucked for the first time anything like what you’d imagined it would be?

It was very exciting for me to finally bottom. I’m not sure my boyfriend was really interested in topping much, but I enjoyed it.

What sort of signals does your body give you when you know that you want to get fucked?

Recently it’s all been visual triggers — if there’s something distinctively masculine about a guy, it catches my attention and focuses my mind on giving up my ass. There’s an almost automatic reaction, I start stroking my nipples and that starts a cascade of horniness.

What makes a great fuck as opposed to just an okay fuck?

Bigger. More aggressive. More physical. A long time from start to finish. Muscle failure. Pig behaviour. Verbal. Restraints. Public. Multiple guys.

Getting a good start is also important — my hole getting some teasing with a tongue.

Spicing things up with uniforms or toys is good. I like wearing a jock — I like being fucked in a jock.

Two of my most memorable fucks were spontaneous fucks. Spontaneous is good.

I met Enrique when we were stationed together. I was 26 and he was 38. I was seeing a man and he was seeing a woman, but I fell for his tall muscular Latino everything and he appreciated my slim runner’s build. Our weight difference was probably 50 pounds — I was about 150 pounds and he was about 200 pounds. We met in the parking lot of an adult bookstore. I wore a civilian top, but still had on my trousers and boots. I followed him home. When we got there we each chugged a beer and he put on his trousers and boots too. Then he had me pull my trousers down just low enough to make my hole available. He pulled his massive cock out through his fly, lubed it up, and then nailed me standing up and pressed against the wall. He was an aggressive brutal fucker that I couldn’t get enough of.

Cliff and his boyfriend were seeking a third guy on Pride Weekend. I think I was the third or fourth third guy they’d shared that day. I showed up after duty and both of them fucked me and bred me. Both guys were well built — the boyfriend was nicely hung and Cliff was like a fleshy beer can. The next couple of times we got together, it was always a group and it was one or two bottoms and four or five tops. I could run to their place — I’d show up in a pair of nylon running shorts and a tank top. The tank top would be used to restrain my wrists. What I really liked about these parties was how they spread my legs open to keep my hole exposed and vulnerable. That drove me wild.

What hints or tips would you give to a younger guy who was thinking about exploring anal sex?

Do your homework. There’s a lot more information available than when I began. Use lots of lube the first few times. Trust your instincts. Know your limits before you play.