Whether you’ve been dating for a while, or just started talking on a hookup app, there are a few things that you should be aware of before hopping in the sheets with a trans man.
For starters, if you’ve never had sex with this person before, don’t assume you will (or won’t) be compatible. Trans men are men. Our bodies are male bodies. You might be super sexually compatible with him, or you might not be. In this way, he’s really no different from any cis man (non-trans man) that you’re considering sleeping with.
Not all trans bodies are alike. We may have had top surgery, lower surgery, neither, or both. So don’t assume that just because he is trans, that he has an “extra hole.” If he does have an extra hole, don’t assume that he likes to use it for sex. Receiving/being penetrated might trigger his gender dysphoria: feelings of discomfort or distress around the perceived mismatch between his sex and gender. Or maybe not! He might be a loud and proud bottom, who thoroughly enjoys using all of his holes for sex. Or he might prefer to top/dom, using mental and/or physical means of sexual dominance. He may use a prosthetic dick, his own junk (which often changes as a result of testosterone) or other means to penetrate his partner. The key thing to remember is, regardless of what surgeries we have had or not had, every trans body is different from the next, and so are every trans man’s feelings about their respective body parts.
By now you might be wondering, how do I figure out what he’s got going on, and whether or not I’m into it? The same way he figures out what you’re into, and whether he’s into you: through communication and consent. This doesn’t have to be a formal, sit-down, serious conversation. It can be fun, flirty, and organic. It can happen in person, on the phone, or over text. It can happen both before and during sex. If you’re cis and he is trans, allow him to take the lead. He will bring it up in his own time, and in his own way. If it’s a hookup situation, chances are he has already made it known what he’s into. If you’re dating, he might be taking it a bit more slowly, testing the waters and making sure that he can trust that you are open-minded, respectful, and not transphobic.
When he is ready to talk about it, be ready to listen and ask questions. This will show him that you aren’t making assumptions about him or his preferences, and that you respect him as a person—as opposed to seeing him as a fetish. (Note: if you’re both into kink, and he is into being fetishized, then have at it—assuming you’re both consenting adults. Just make sure you aren’t fetishizing sex with trans men in general, or thinking about sex with trans men as a category of kink. This is disrespectful and dehumanizing to trans people.)
Ask him if there is anything you should avoid doing or saying during sex that might trigger dysphoria. He might not want to be touched in certain ways or in certain places. He might want you to talk about certain body parts or sex acts in certain ways, and not others. Don’t assume that you need to make certain accommodations—again, every trans man is different. But do make sure you’ve created space for him to voice any triggers he does have, and assure him that if you do or say something that makes him uncomfortable/dysphoric during sex, to tell you.
And finally, be open-minded, responsive, and willing to learn and get creative. This is the key to all good sex: at least in this trans man’s opinion.