My Urge to Date a Trans Woman

My Urge to Date a Trans Woman

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I’ve been crossdressing for what soon will be a milestone anniversary. It’s been a fun ride.

Along the way, due to my career as a freelance journalist attending corporate meetings, trade shows, and other events, I must also maintain a cisgender male appearance. I can handle it. Being a journalist helps me put food on the table, purchase alternative clothing and simply put, enjoy life.

One thing that is missing is the opportunity to date and have a relationship with a trans woman. I have interfaced with trans women on two occasions, and experienced intimacy. But that was more of a one-night stand.

I realize there may be challenges dating a trans woman as well as offering greater complications than your average cis relationship. Meeting someone locally if you live in a small, populated community or are considering a long-distance relationship can also add to the dating challenge. 

In doing my due diligence regarding such a relationship, I have read many positive and negative elements of dating trans. Many men are embarrassed to be seen in public with a trans woman. Some men won’t introduce their trans girl friend to their family or friends. Some have said they could lose their jobs if their employer found out they were dating a trans woman.

Recently, through an alternative lifestyle site, I started chatting and getting to know a trans woman. She has beauty. A positive outlook on life, though dealing with health issues (aren’t we all) and could write intelligently. We’re communicating but haven’t met – yet.

So, what are the advantages (or disadvantages), or reasons to date a trans woman? Here are my thoughts and feelings.


Sadly, I have learned, many trans women have a difficult time socially or have experienced hardships in one form or another. It’s unfortunate. However, I feel this can make trans women some of the nicest, most open minded and accepting people you’ll ever want to meet. One item I read said, “if you have a trans girlfriend, she’s going to like you for who you are.”


I feel a large percentage of trans women put greater effort into being feminine than cis women. As a result, they’re more stylish and attractive. In fact, trans women can be stunning. And maybe I’ll learn more about applying makeup, doing my hair and more.

Oh yes, sex.

I think it’s a fact, many cis women tend to be prudes when it comes to sex. I have experience here. From my research, trans women are more open minded and willing to experiment in the bedroom – and out, and are often eager to satisfy. Still, not all relationships involve sex.

I realize there are different ways to pleasure a trans woman. First and foremost, it’s important to know before being intimate whether she is a top, bottom, or versatile. Don’t make assumptions. The next thing to discuss is if she is pre- or post-op (if she even wants to have vaginoplasty). If a partner is pre-op, her prostate will serve as her G-spot and anal stimulation may be key to providing an orgasm. If she is post-op, there will be a need to know if she can be stimulated through vaginal penetration or oral. This is really the same as sex with a cis woman. Simply put, do what most pleases your partner and remember, communication is key. I would be happy to fulfill my trans girlfriend’s needs.

At the end of the day, it’s possible to have a great sex life that can remain consistent throughout the life of the relationship.

Kids. What kids?

Dating trans means no worries about getting your girlfriend pregnant. That’s a big relief. If she has family (kids) from her former life and is willing to introduce you to them, be congenial and accepting. If dating leads to marriage, and you want kids, you can always adopt.

We only live once

I suppose that’s one way I can look at it. I felt why not give into my urges and see what life can bring me. Put aside any concerns and social burdens and live life on my own terms and have a genuine interest. Time will tell where the road might lead with the trans person I recently contacted or if I have the opportunity to meet others. If my adventure goes anywhere, I’ll share that experience with you.

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