Ask Beastly: Can I Hire an Escort to Teach Me How to Top?

Yes, but ask the right questions first.

I’m a 46-year-old gay man who has only had “side” experience with sex. I am going on vacation to NYC in a couple of weeks and was thinking of hiring an escort to teach me how to top. Is this a good idea? Will they laugh if I ask them to teach me? How do I ask for it? Where can I find a professional escort who will be willing to teach me?

Hey babe,

I think this is a great idea—so long as you find the right guy. Finding the right person will require extra communication and careful selection, but that’s advised when looking for any escort. Good communication always means a better time.

I’d recommend using Rentmen (rent.men), a European-based site most gay escorts I know are on. I can’t recommend anyone specific, but I would look for a man who is a bit older, not just a young guy in his early twenties, who provides “boyfriend experience” work—who is comfortable with talking, intimacy, and conversation—and, of course, is top or (even better) versatile.

Truly versatile men are great to learn from because they know the topping experience from both sides: they know how it feels to fuck and get fucked. This is an open secret in gayland: the best tops are bottoms, too.

An escort can be an educational and enjoyable experience, and I think you can learn a lot from one (or several) escorts. Still, I want to stress that you won’t learn everything about topping from one encounter with one person, and you should not restrict your “top lessons” to escorts. You need "top lessons" with friends, too.

Hire someone; it’ll be fun. But also look for playmates in your area that can exist in your life between “friend” and “lover”—casual connections you can talk to about sex and practice with. You will learn how to top well by practising with many guys, and good sex buddies will give you kind, honest feedback (a good escort will, too).

The best tops I know focus their arousal on pleasing their bottoms. That seems to be a common feature of “fuck, wow, amazing” tops. So, as you begin this journey, make his pleasure (whoever “he” is in the moment) your goal.

This, I admit, can be tough with an escort, since an escort’s job is to make you, the client, feel good. Generally, when you pay for a service, you are the one who must feel good, so you will need to communicate clearly with the escorts you hire that you want honest feedback on topping and need honest, clear, actionable tips on doing it well—that you are paying for advice and education, not pleasure.

They will not laugh. If anything, they will probably appreciate the request. Escorts are asked to do many extreme, annoying, and even dangerous things. I have been asked by more men that I can count to infect them, rape them (or rape someone else), tie them up (usually when they have no experience with bondage), beat them, break their bones, kidnap them, drug them or provide drugs for them, and much more. None of these are things I will agree to. After ten years of escorting, it became tiresome to repeatedly state my limits. Even near the end of my work as an escort, clients still did not respect these limits and often lied about using drugs, and they nearly always tried to trick me into staying longer than the agreed-upon time without paying for it.

Suppose someone had asked me to do a nice, sober topping lesson; that would have been great. I’d ask some questions up front, as a good escort should. Questions like: Do you want to be the one who is topped, or would it be more helpful to see me top someone else? (If you want to see another guy get fucked, you may have to pay for his time, too.) And: How much experience do you have with topping and bottoming? Do you know about douching? Do you have any struggles with maintaining an erection? Do you have any doubts or insecurities that I might be able to address directly?

If someone asks you questions like these before you meet, that’s good. He’s a quality guy.

Aside from this, enjoy other parts of New York City while you’re there. Walk the High Line, get dinner in Chinatown, wander around, grab a drink at the Eagle, and have fun. New York is a sexually-charged city, but that's only one facet of its wonder. See the rest, too.

Love, Beastly