I’m a Sex Worker. I Had a Client So Good in Bed That I Want to Do Something Unprofessional.

Our advice columnists have heard it all over the years—so we’re diving into the How to Do It archives to share classic letters with our readers. Have a question? Send it to Stoya and Rich here. (It’s anonymous!)

I am a 30-something transguy who does in-person sex work. I’ve been at it for 11 months, and I’ve had about a dozen clients. Some repeats. It’s been lucrative, but a little meh, as all the dudes have either never been with a transguy or they’re slam-it-out kinda guys. Neither has been very fun. Then a month ago I met a guy I’m going to call the Client. The encounter started off scary.

He requested that I wear tighty-whities and told me to strip down the second I entered his apartment. He said I only get to wear underwear in his presence. But then he walked up to me and said he constantly talks dirty during sex, and were there any words or phrases I would like him to avoid? The mood changed, and I ended up having the best sex of my life. Period. No question. I orgasmed, and I never have with a client, and only rarely with my girlfriend. I left his apartment feeling lightheaded, shaky, and somehow more relaxed than I can remember ever being. No, I was not drugged.

I have not stopped thinking about the Client since. I imagine him when I have sex with my girlfriend. I think about him when my mind wanders. I want to break up with my girlfriend, who has never once asked me if any words or phrases trigger my dysphoria. I never even had to suck his dick. He made the encounter very focused on me. With my girlfriend, I feel like our sex is all about me pleasuring her, orally and with a strap-on. I searched the Client’s phone number online and found the social media pages of his kids, who seem to be from different ex-wives. I imagine breaking up with my girlfriend and asking the Client out to dinner. I know this is crazy. He’s 25 years older than me.

Is it OK to ask him out off the books? And is this temporary insanity brought on by a single instance of mind-blowing sex? It wasn’t just that the sex was good. It was that the dirty talk was so affirming of me as a person. He hasn’t been in touch in over a month and I’m acting like I’ve had a breakup. My friends have noticed something is up! Ugh.

It’s a brutal world and love is elusive, so I wouldn’t begrudge anyone the opportunity to seek and find love in any situation, even one where the connections forged are based in commerce. But I don’t think the Client is your guy. For one thing, you haven’t heard from him in over a month. If he were interested in piercing the very distinct boundaries of your interaction—customer and vendor—you’d likely know. This guy, as your less-than-ideal snooping uncovered, has his own life. He likely hired you because you have nothing to do with it. Unless he has given you actual indication that he’s interested in something more off the books, your pursuit could serve to push him away for good. Ask yourself if it’s worth the risk. “I know this is crazy,” are your own words.

I do think there’s a lesson here, though. You have been having sex with people who are either inexperienced with transmen or inconsiderate.