Dear Jamie,
I started dating a trans girl that I met during some team building games our corporation put together. We hit it off quite naturally, sharing many interests and a wacky sense of humor. I never dated transgender women before and don’t have a particular kink or preference—I’ve fantasized about it from time to time, but I fantasize about a lot of things now and again.
It’s a new experience for me, and I was open and didn’t hesitate to ask her out. We enjoy quirky movies and spicy food and playing volleyball.
Everything’s going great, except one thing—sex. We haven’t been intimate yet because Li is worried it will end our relationship. She is afraid I’ll be disappointed because it’s not what I’m used to, and that once I satisfy my curiosity, I’ll go back to cis women.
The truth is, if things don’t work out, I probably will “go back” to cis women because I don’t know any other transgender women and because I don’t have a specific attraction like many of the guys reading this website, which I stumbled on while looking for information online. But I want it to work out, and I’m open to learning about Li and her body and needs and giving it a go. How long should I wait? – Faisal
Hi Faisal, thanks for sharing. Trans women seeking sex and love with cis men have tough challenges. It can be tricky trying to find someone to like you for who you are when your body is different from other women’s bodies. But if you go with guys who have a fetish for you, you risk being objectified or used for sex.
That’s the stark reality, but it gets even more challenging when your own body has been the source of baggage, dysphoria, confusion, discomfort, and pain. Sex is a loaded exchange for anyone, but for someone who has spent their life in a mismatched body, or been rejected for things they can’t control, it can be frightening to let go.
How long you should wait is up to you. From what you describe, it doesn’t seem like you are being used or strung along, but that you are sharing a healthy friendship plus. Some in your situation have sex on the first date, and some wait until they’re married! That’s personal.
I think the more important thing is not about setting a date or timeline, but having an open conversation about sex. See if you can both use humor to have a candid, hear-to-heart exchange. Don’t give her false reassurances that you can’t really promise—they will ring hollow. Tell her the truth, that you want to experience this with her because you fell for her in particular.
No one knows the outcome, no matter what their body or body parts are like. Ask her to risk sharing with you her past sexual experiences if it doesn’t feel too private. They may have been painful, uncomfortable, unloving, abusive. They may have been fleeting, and now here is something that matters. She might just be scared.
Take the pressure off both of you for now and decide to fool around for a few weeks without getting to sex. Get all hot and bothered without having to worry about the next level, and just enjoy getting revved up. My guess is that before long, nature will take its course, and it will be beautiful. – Jamie
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