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Dear Alex,
I'm a gay trans man, and I struggle with the fact that I "pass" as a man when I'm dressed, but when I'm naked, I look very androgynous.
I've had top surgery, but I don't want to change my genitals. Testosterone gave me a really deep voice, but no face or body hair at all. I'm very lean, so I don't have curves, and I've been working out for a few years now, so I've got quite muscular arms and legs. But when I'm naked, the effect is sort of a masculine/feminine blend.
Men check me out. I'd love to return eye contact and hook up if it came to that, but once we're naked together, I feel like they might change their minds. I need a plan for if that happens because I feel like the fear is making me miss out on some amazing experiences.
Thanks! Change the language if you need to. I don't know if some of these words are OK.
Eliot
Hey Eliot,
Your language is fine. If Meta or any other censoring, queerphobic entity takes issue with it, I might as well give up writing entirely, because everything I've written about myself is more explicit than your question.
You want a plan for a very specific moment: Being naked with a guy who's having second thoughts because your body looks a little feminine. You're already playing that moment out in your mind, bracing for the shame and discomfort of it.
Not to undermine the unique struggles of being trans, but every cis gay man, including me, fears the same thing. We all have body insecurity. We all dread the nightmare hookup scenario of being naked with someone impossibly hot who, in the moment of our undressing, decides he doesn't want to have sex with us. It's universal. It's human.
Rejection does happen, though in my experience, as someone who worked as a sex worker for many years and has been a slutty man for half my life, it more commonly happens at the pre-sex moment from app-based hookups: The moment when you meet someone in person and either they don't look like their pictures, or you both just mutually realize it's not a match. When you meet someone in a bar, and he knows you're trans by the time you go home together, it's unlikely he'll lose desire once you undress. He might lose a little confidence, because sex with someone new, whose body you don't fully know how to please, can make anyone nervous. And in that moment, someone needs encouragement and instruction.
Since I'm a cis guy, I looked to some experts who are trans and have written on this subject. Devon Price is a gay trans man, social psychologist, and author of Laziness Does Not Exist and Unmasking Autism, who writes about transmasc dating and sex on his Substack. On the impulse to wait until your body passes more convincingly, he is blunt: "Nobody arrives at such a dramatic change in their identity and orientation hastily; you have waited long enough, questioned yourself plenty, and made enough of those damning, practical little sacrifices that keep the life you want at bay. The days of waiting to become the type of person who leads the life you want can be behind you forever. The way we change who we are is by changing our surroundings and actions."
For some, he notes, passing never fully arrives: "Some people take T injections for years and simply never start passing, due to some quirk of their genetics. You can't ever really know how your transition will settle on you."
On rejection specifically: "Dysphoria will tell you that if your body betrays even one hint of stereotypical femininity, queer men won't want to have anything to do with you — but your dysphoria is a liar." He recounts setting up his first Grindr profile in 2021 when he still "looked physically quite feminine, with a round face, curvy hips, and D-cup-ish boobs." He expected rejection. Instead, his phone overheated from notifications.
Price also punctures the idea that cis gay men are drawn only to masculine or cis-presenting bodies: "What some men find most attractive about other men are hard, pulsating cocks. You'll be hard-pressed to get much attention from a dude like that. If some guy on Grindr tells you that you're not his thing because you're not 6'2'' and covered in muscles, well, that just makes you like any other guy who sometimes gets rejected and has insecurities about his ability to live up to cartoonish standards of masculinity. Talk to your fellow queer men for a second, and you'll realize you're all in the same spot."
I've had sex with many trans men (I even wrote about these hot times in The Advocate, Out’s sister publication, though I’m not sure how well that piece aged). What I know from those experiences is what cis men are thinking in the very moment you fear. We're eager to please, a little nervous, scared of saying or doing the wrong thing, but hopeful. We need more guidance than you might need to give another trans guy, but giving that guidance can be hot.
JD Davids, a transmasculine writer and HIV activist writing for The Body (a great HIV resource and publication I've also contributed to), asked trans men what they'd like cis men to know. "You think we are hot, so tell us we are hot," says a trans man named Hal. "I like when men express verbal desire for me, preferably in a way that lets me know you see trans men and me specifically as individuals." Another guy, Curtis, says: "Don't assume you have to be more gentle and careful with my body than other men."
What would you tell cis guys? What's your message for the cis men who want to sleep with you? Think about that and keep it in your pocket. When he's naked with you, a cis guy probably wants to be led. Tell him what to do.
So let's create an action plan. You get naked. The man in front of you sees your full body for the first time, original genitals and all. Break the ice. Say something like: "Might as well start with a vocabulary lesson. Here's what I call my parts."
Some trans guys say front hole, others are comfortable with pussy or vagina, and still others have their own words. A trans guy I regularly sleep with calls his clitoris his "little dick," so that's what I use with him. Have your words ready and state them at the outset. Then say something like: "I like when guys do X, Y, and Z." Give just enough instruction for him to latch onto, because if he feels like your body is a test with no rules and no foothold, he'll feel like he's failed before he starts, and that can make anyone lose the heat. Give him a foothold.
If he's good at sex, he'll ask questions. Before I touch anything, I ask, with people of all genders, things like: "Can I touch X? Is this OK? Does that feel good?" But the average cis gay guy may not prioritize such clear negotiation or consent, so you might have to take the reins. Tell him what you like and what you don't. Give him the map. Most men, when handed a map, are relieved and grateful and follow it enthusiastically.
What if the moment goes badly anyway? What if he recoils, or goes cold?
That's information about him, not you. In my early years of being HIV-positive, I waited until there was real interest and chemistry before telling a guy my status, which made their refusal all the more painful. Now I get it out of the way as quickly as possible. I don't want to be interested in anyone who'll reject me for my status, so it's my first filter. Their rejection is information about them, not me. I don't want poz-phobic guys in my bed. You don't want transphobic guys in yours. Share everything that someone might reject you for as early as possible, even the specifics, so that the things you can't change help weed out the people you don't want anyway.
This requires being bold and perhaps a little sexually forward, but it pays off, because the right guys, the ones who say yes at each step, will be eager and excited once you're finally naked, and will only give you a "hell yes" in that moment too.
And you're always allowed to leave. Get dressed and go. You don't owe anyone an explanation of your body or a moment longer than you want to give. The door works in both directions.
The men who react badly aren't representative of all men. Price writes that some "are attracted to masculine energy in particular, and can find it in any type of person, regardless of their physical embodiment. And then there's lots of men whose sexuality is more complicated than simple gender labels or stereotypes, who would have liked you under any identity and will be happy to see you grow and change on testosterone, too. These ones are real keepers."
For what it's worth, I try to be one of those real keepers, and there are more guys like me out there than many people might (reasonably) think. We're here. You just might have to slog through a lot of assholes to find us.
You said fear is making you miss out on amazing experiences. It might be, and the only way through it is to dive in. You can't conquer this fear any other way except by going home with guys, or going to cruisy spaces like sex clubs and bathhouses, and seeing what happens. You will encounter a range of people and responses, and collectively those experiences will be a tough and hopefully affirming education in how to navigate the strange, infuriating, and delightful world of men.
Welcome to the playground, Eliot.
Hey there! I’m Alexander Cheves. I’m a sex writer and former sex worker—I worked in the business for over 12 years. You can read my sex-and-culture column Last Call in Out and my book My Love Is a Beast: Confessions, from Unbound Edition Press. But be warned: Kirkus Reviews says the book is "not for squeamish readers.”
Here, I’m offering sex and relationship advice to Out’s readers. Send your question to askbeastly@gmail.com
