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You might be an open minded lesbian who has been around the conversations happening in the queer community, and you might be open to dating a trans woman who self identifies as a lesbian. You might be a trans woman in a community of poly, neurodivergent, gender non-conforming, gender non-binary, pansexual folks who think being trans is old-fashioned because it is part of the gender binary. And you might still be interested in dating and might need to have your mind expanded as a trans person by the next thing in gender and sexuality.

These are all experiences that you might have if you want to date a trans woman, and these are some of the many different kinds of trans women there are. Some of us have been across the entire spectrum of these experiences, from living lives where we were read as men and in an old-fashioned narrative felt like we were in the wrong body to living a life where we are trans and think we have done everything we are supposed to do to transition.

We have had our surgeries, taken hormones, changed all of our identity documents. Transgender women love to have orgasms, and contrary to popular opinion, trans women have amazing orgasms that would blow your mind if you had one. And they have all kinds of orgasms. A trans woman can have an orgasm with a penis that is just fantastic, or she might have an orgasm getting anal through her prostate.

A trans woman post op might have an orgasm with her clit, or she might have one deep in her g-spot just like a cis woman. Just like any woman, it might take her a little longer to get off then it will take you, especially if you are a cisgender man. But give her some time to get to where she is going. The reason I say this first off in dating advice is because I know we all want to get there. That magic that comes from getting off is the juice that makes the magic, it is the electricity in the machine, and it is the high we all crave, that fantastic orgasm.

And trans women want the same thing. It might be a little embarrassing for some trans women to have a penis, but it is just as unembarrassing for a lot of trans women to have a penis.

1) Before You Start, Educate Yourself With the Basics

Lots and lots of trans women have penises or penes if you want the proper English usage to indicate multiple penises. I know so many trans women who are either pre-op or non op that look better than you ever will and will get any man they want. But for a lot of trans women, we have felt or do feel embarrassed about that because we feel or have felt that it is the one and only signifier of gender identity that really matters.

Save us all some trouble. Having a penis is a big deal for some people. For a trans woman, it can be great to have a penis because there are so many men who are into beautiful women who have a penis but are also women in every sense of the word. If that is the kind of woman you are into, then more power to you. I have a list of trans women who would love to date you. Getting over the fact that a woman has a penis can be a huge barrier for a lot of people.

This Is What It’s Like Dating A Transgender Woman

For trans women, it can be a real source of danger and harm, and that is why I would always recommend disclosure. This is not only disclosure of your body parts, but also just disclosure of gender identity generally.

Trans Women Discuss Online Dating

I always think that safety is the most important thing for any trans woman. Far too many of us die or are hurt every year because we are transgender. I think that just like the way we step out of the road to avoid getting hit by a car, we know that there are always going to bashers and haters out there and the best way to avoid them is just to let them know from the start who and what we are. It is great to live in stealth if you can, and I know that is an old fashioned word.

Sex is in the brain. That is the most important thing to know about a trans woman. Everything that she does, everything that we do, is about life and joy and pleasure. What a transgender person has to offer you in terms of sex and dating is the same thing that any woman can offer you.

But she is also going to challenge your ideas.

This Is What It's Like Dating A Transgender Woman - Role Reboot

However, if she does, that is good for you. Because part of being trans is about deconstructing heternormativity and gender. Our bodies are all about pleasure, from the way we love and bond to how we cum. It is all about pleasure and joy, and when we date and have sex and make love, we want the same thing, any body and any person. There are different kinds of outcomes of love and pleasure. The most important outcome is that we can have experiences that change our lives, filling us with magic and joy and appreciation for life and all its wonders.

And we can ultimately find our innermost fulfillment in the deep meaning that can happen in strong interpersonal relationships. Trans women are capable of all these things. Trans bodies are amazing.


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We have been one gender in terms of how we were treated and what was expected of us, and then we became another gender, the one that matched our gender expectations. To me, that is incredible. It makes us amazing lovers and incredibly giving people, deeply perceptive and appreciative of love and physical intimacy. This is what I mean by the concept that sex is in the brain, and this is what I meant at the beginning of this blog post when I said that dating a trans woman will take you on a magical mystery tour.

Understand, though, that you should only date a trans woman if you are ready to date one. Just like any queer identity, trans women are ambassadors of queer culture. Like it or not, we are going to challenge your expectations. With some trans people you are always going to sometimes see a male body and sometimes a female body. But then, once you get accustomed to trans and gender queer bodies. You will begin to see how gender is a construct, and it is a game that we all play. Two weeks ago a drunk guy made out with me in a club then asked if it made him gay.

Dating a Transgender Person: How is it Different?

There are literally millions of straight men who find trans women arousing — maybe even your dad, for example. Sadly, this is something trans women share with women in general. Part of the problem is that sometimes porn is the only lens that men have seen trans women through, and they forget that any woman in porn is presenting a fantasy. Most of the time when I am talking to men on dating apps, I am sweeping pizza crumbs off my chest on the sofa.

Dating and Safety Culture for Trans Women

Sometimes, men find this disappointing. Meet this guy below, who asked me out on a date a few weeks ago then told me just as we were arranging it that he already had a girlfriend. Dating as a trans woman involves placing a high degree of self-worth upon yourself and your time, ladies. This is a matter of personal taste. Some trans girls get a standard dating app like Tinder and choose to disclose the fact they are trans on a need-to-know basis.

I personally would rather not talk to someone for ages before the potential for them to go nuclear and call me a deceptive freak or some other charming form of abuse when I mention the teeny, tiny fact that I used to be a boy. This has the benefit of ensuring men you speak to are looking for a trans woman specifically but it does also have downsides. Trans girls are at the same risk, if not more, of exposure to HIV as gay men. If you are meeting someone for the first time, try and meet somewhere public, or at the very least tell a friend where you are going.