Sex with Transgender Women: What to Know

If you’ve been flirting with a transgender woman online, you might be jerking off and planning the night of your dreams.

Maybe you’ve always fantasized about transgender women and checked out trans admirer sites and porn. Or maybe you are simply open minded, and now you’re attracted to a woman who happens to be trans. Maybe you’ve dated t-girls before but never made it to the bedroom.

You want to be respectful, caring, and generous, but when it comes down to the nitty gritty, you really have no idea what to do. Never fear. Here’s what you need to know before you make love to a transgender woman.

What You Should Know about Transgender Sex

All women are different, and this one is no different.

A great lover knows one thing above all else: every woman is different. No matter how many times you’ve made love, no matter how many women you’ve satisfied, the next woman is not like the last one.

Your last girlfriend may have loved your special finger-swirl, and your date last night got off on your filthy bedroom talk. But playing those cards won’t work on a new hookup.

Your transgender date will respond in her own way, and if you date ten trans women, each one will respond uniquely in bed.

Making love to a trans woman is not all that different from making love to any woman.

At the same time, even though every woman is different, you might worry that making love with a transgender woman won’t feel like making love to a woman. And this is not the case. She is a woman, and the experience and sexual energy will feel familiar. You will be in familiar territory.

Ask her how her body works and what she wants in bed.

The only way to navigate her needs is to follow her lead. Ask her what to do and how to do it.

You don’t have to bring it up out of context. When things are getting hot or you’re making out and know the clothes will be coming off soon, say something then.

“I hope you’ll show me how you like being touched” and “I want to be sure this is good for you” works wonders.

Don’t ask what she’s packing.

If you’re flirting online, or talking over dinner, it is disrespectful to ask questions about her genitals or private life, so don’t be rude or go all medical doctor. Not sexy.

Forget questions about what kinds of surgeries she has had or what her genitals look like.

Once you are there, it’s okay to communicate that you want to be safe, give her pleasure, and avoid hurting her. “Show me” is probably all you need.

The nitty gritty.

I get it, there’s more you want to know.

If she has a cock, it won’t work the way yours does. The she-male porn is fantasy. There may be an exception, but for most trans women, hormones make her dick soft and spongy so you won’t be jerking it or getting pegged. Some trans women enjoy being stroked and licked, and some don’t want to use it at all.

She might want anal sex because penetration can be powerfully erotic and essential to her femininity.

Don’t assume anything. Explore it together.

Treat her like a lady.

Focus on relaxing while you make out, undressing her slowly, paying attention to the details of her lingerie or outfit or makeup, and making room for the sensual. Be unrushed and prioritize her pleasure. Be a gentleman, and make her feel comfortable. Take your time. Enjoy her.

That’s really all you need to know. Relax. It will be amazing!

Looking for more transgender hookup tips? Read my Advice for Your First Hookup with a Transgender Woman.

Have you hooked up with a trans woman? What tips can you share?

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