Q&A: First Time Hookup with a Trans Woman

Maybe you’re a new I Love TS reader. Maybe you’ve been an trans admirer for a long time but haven’t yet fulfilled your fantasy or met the right woman.

Any new sexual experience can be as intimidating as it is exciting, but if you’ve never made love to a transgender woman you might have questions or be uncertain as to how to proceed.

Everyone says it’s the same as being intimate with any other woman, but that’s not really true, is it? Your TS date has a different body, differently made, and a different set of social and environmental experiences. You want to have a general idea what to expect and how to please her.

Here are answers to a few big questions men have about sex with transgender women so that you can relax and enjoy the pleasures ahead.

Will I be able to tell a transgender woman apart from a cis woman in bed?

Yes, more than likely. She may be larger, longer, with bigger hands and feet than most cis women. She may be more angular and have different patterns of body fat deposits. You will see most of the ways she differs from other women before getting undressed, however, so if you’re attracted to her, don’t worry about it.

Her pussy will be similar to a cis woman’s, but she won’t menstruate, and she’ll need more lube. There won’t be any surprises you aren’t expecting, though. Just obvious things you already know about.

Will her breasts feel natural or artificial, and does it feel good for her when I touch them?

Depends. Hormones can grow a whole set naturally without surgery, and they will look and feel like breasts. As for enjoyment, yes, although hormones can make them tender and sore, so pay attention and be gentle.

For many trans women, breasts are such a powerful emotional connection to her true identity and sexuality that some have orgasms just from breast play or nipple stimulation alone.

How will I know whether she has a pussy or a cock?

You’ll find out soon enough!

It’s considered the worst of manners to ask someone what they’re packing. In my experience of dating transgender women, they have usually told me before we got together what I needed to know and what she would be open to using on me and enjoying from me.

Don’t worry too much. Enjoy the experience for what it is. You’ll figure out your turn ons and preferences with experience, but try not to be fixated on them in advance. People with the hottest sex lives enjoy many different kinds of sensations and see beauty in a variety of bodies.

Will she want to do my ass with her dick?

It’s possible but not probable. Women taking hormone therapy usually don’t get the kind of erection necessary for that kind of penetration.

Will she expect or want anal penetration?

If your transgender date doesn’t enjoy her cock being touched, or if being penetrated makes her feel more feminine, then yes, she may really enjoy anal sex. It’s still unlikely that she’ll be “expecting” it.

Remember, not everything has to happen the first time you have sex. If you’re hoping for anal sex in particular, say so in your casual hookup profile, or look for dates who are looking for tops. Otherwise, go with the flow and let the experience unfold together.

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