Ask Beastly: I’ve Fantasized About Gay Sex for 18 Years—What Now?

A straight man wonders how to begin.

Hi Alex: Tim here…liked your Advocate article. I’m curious about sex with another man. Never tried anything like it but had a recent situation that got me thinking. I was meeting a new colleague for cocktails. I sensed he was gay (no big deal), and I can’t say I was necessarily attracted to him either. That said, we were sitting at the bar, and he put his hand on my groin. I wasn’t sure what to make of it but noticed a flush of blood in that area. He then (very subtly) pulled my fly down, reached his hand into my pants, and started touching me. My heart started to race, and I was incredibly wet…like crazy wet. He asked if we could go back to my hotel, and I just couldn’t wrap my head around it and passed. Here’s the strange part, that was 18 years ago (I’m in my 50s now) and ever since then, I’ve thought about all types of MSM sex, including anal (bottom). My question is, what’s the best way to get someone to help me with personalized dilation? Apologies for the lengthy note too.

— Tim

Hi Tim,

Your note is the perfect length. And hot.

I’m not sure which Advocate article you’re referring to, but thanks for reading it. Eighteen years is a long time to keep desire at bay. You keep it tucked into a memory, and the clarity of that memory—how well you tell it—proves this desire is here to stay. People are ready when they’re ready, but if you need a little push, this is it.

It may help to remind yourself that you’ve already had a sexual encounter with a man. That discreet cock-touching at the bar was, unequivocally, a gay sexual experience. It was not anal sex, but it was erotic, and it was with a man. It counts.

Anal sex is not the final destination for MSM intimacy or even necessarily the best one. An erotic MSM encounter can take many forms, but you certainly had one. I have enjoyed cuddles and kisses that rival my best ass-fuckings. You simply want another experience—you already had a first.

Browse my archives. I get many questions from men who want anal sex for the first time—go explore. As I have written elsewhere, a sex worker can be helpful in giving you a good, custom-tailored anal sex experience. If he is good at his job, he will foster a safe space where you can ask questions and get feedback. A great sex worker will even sit down with you and discuss ass-cleaning tips, anal relaxation methods, and more, so long as you pay him for his valuable time. He might use toys to help you become comfortable with the feeling of your ass opening.

A good playmate or casual sex friend can do this, too—they can be just as good as a sex worker, if not better—but sex friends are reciprocal encounters. They expect pleasure in return. A sex worker is a service you pay for, so the focus is fully on you. You do not have to worry if he is having fun or enjoying it. He’s just doing his job.

Fantasies are great. But doing something with them is even better. Acting on desire is one of the most important journeys a person can go on. But you must find the strength and bravery to start. You do not know where you will end up, and truthfully, there is no “end”—there is no final stop on pleasure, not in your fifties, not ever.

There will be challenges you cannot prepare for, hurdles you must cross, and struggles you have to figure out, but that’s sex, and you must face them as they come. But if you stay with it and do not give up, you will have a better, happier, and more fulfilling sex life. That is worth the work to get there—forever, always.

Love, Beastly