Advice for Your First Hookup with a Transgender Woman

Dear Jamie,

I’ve been chatting with a sexy girl I met online, and it turns out she is transgender. I’m curious and totally open to dating her or hopefully meeting for hot hookups. Most of the advice I find online says it’s no different from dating any other woman, but that can’t be totally honest, can it? I’m horny but nervous about the sex because it is new to me. I don’t want to look like I don’t know what I’m doing. Help! – Kyle, 25

Hi Kyle,

Thanks for writing, and kudos to you for being open minded and seeking the information you need.

There is no need to pretend to be suave and experienced. Be honest and vulnerable. If you show up claiming you’ve been with dozens of T-girls, it’s going to be awkward for both of you. Let her know you’re totally into her, but that it’s your first time dating a trans woman.

It’s true some transgender women aren’t interested in teaching someone the ropes, and being honest in advance means she can move on, even if that sucks for you. That’s unlikely, though.

Besides being open about communicating questions and ideas, my advice is to take it slow. You might feel strange about hooking up on your first encounter and not know how to navigate the followup, which can leave both of you in an uncomfortable place. Even if you’re looking to keep things casual, meet up for drinks or a movie or leisurely walk, and enjoy flirting and making out without feeling the need to rush into the full monty. If that does happen, it will be because you both want it bad, not because it was expected in advance.

I suspect you are asking between the lines about the nitty gritty—you didn’t mention whether she is transitioning or post-op or any other clues, and you probably feel it’s rude to ask her whether she has a surgically created vagina, a functioning cock, an out-of-commission penis, or whatever else might be going on down there. You also didn’t say that any of those options are “out” as far as you are concerned, but you might have some anxiety about “what to do” with whatever appears, if you’re not experienced with that particular equipment.

Your best approach again is to be candid about it. “I’ve never been with a transgender woman, so I hope you will be able to show me what you want and what feels good.” If you’re worried about handling a penis, don’t—you’ve handled yours successfully, and so you’ll have more of a clue what to do than you think. But many trans women who have penises are also taking hormones that change its function, or they don’t like to use it because it causes gender dysphoria. She might want to leave that part out. Don’t assume anything—just be up front about wanting to give her pleasure in the ways that work best for her.

If she has a vagina, it might be too new to be ready for sex, or it might be no different than pussies you’ve already enjoyed.

To keep from getting too tense “on your way,” take things slow and give lots of attention to her breasts. This will heat things up, and give you both a chance to show each other what else you want.

Let us know how it goes! – Jamie

Looking for more transgender dating tips? See 5 Tips for Dating Transgender Women at I Love TS.

Hookup Help is a Q&A series. If you want advice or a female’s perspective on hooking up, online dating, relationships, or sex, we want to hear from you. SUBMIT YOUR QUESTION, and who knows, you may appear in the next Hookup Land newsletter.

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