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Do Ladyboys Date Transmen

Many people think that the perfect union for trans people is two trans individuals with opposite genders. This means that they think the ideal match for a transgender woman is a transgender man. However, this happens very rarely. Most ladyboys still date cisgender men, as most trans men still choose to date cisgender women.

What Is a Transgender Man?

He is a man who was assigned a female at birth. Most of them were raised believing that they have to express their gender in a more feminine manner as their genitalia supposedly dictates what their expression must be.

trans man

Some of them look completely “male” with the help of hormone replacement therapy (HRT) and gender reassignment surgery (GRS). The ones who underwent medical intervention are very hard to “clock”.

Some transgender men have

  • Gotten their breast tissues removed
  • A hairy body because of HRT
  • Pronounced facial hair because of HRT
  • Bigger muscles because of HRT and fitness efforts
  • Gotten their ovaries removed to stop producing estrogen that feminizes their look
  • Went through phalloplasty (penile implants)
  • Kept their reproductive system but have gotten rid of their secondary sexual characteristics
  • Not gone through medical intervention but express their gender as a man


These men mainly date cisgender women. This is not caused by internal discrimination but is a matter of preferences. The same way goes for ladyboys, exclusively dating cisgender men.

Much like most men, these men initiate the conversations. They also do the chase. Not because they are trying to emulate cisgender men but because such emotion is natural within them. A lot of transgender men share the same outlook and interests as cisgender men.

This is why when it comes to ladyboys dating these men, the latter has the ball. If they decide to pursue ladyboys, all they have to do is do the same whenever they’re expressing their attraction with cisgender women.


Some transgender men are comfortable with their genitalia. A lot of them are not. Their sexual role highly depends on the individual. If they prefer being a top, they will either use a toy or other ways to penetrate.

If they have no problems being on the receiving end and if they’re dating a ladyboy who’s comfortable with her penis, they will have sex just like how heterosexual cis couples usually do it.

Added to that, some transgender men are not straight. They’re into cisgender males or transgender men. Not all of them exclusively have sex with women.


If the trans couple should decide to spend the rest of their lives with each other, there will be fewer challenges. The reason being is because they will be able to build a create biological children (as long as they still have their reproductive systems intact).

Furthermore, many countries still don’t allow same-sex marriage. With a union like this, such a problem will also be immediately eradicated. The only challenge that may come their way is… society.

Just like any other person in the LGBTQIA+ spectrum, they’re still subject to discrimination. Furthermore, matters are worsened if they are both ostracized from the workforce. This will hit hard should they already be sharing a child.

Do Ladyboys Like Transmen?

Yes, some ladyboys are attracted to transmen. After all, sex does not define one’s gender. Added to that, most ladyboys are attracted to masculinity.

a transman

Why Some Do?

Some ladyboys have no problems dating transmen because they’re more open-minded. This is usually more apparent in the west. Gone are the days when transgender men are poorly portrayed. Thanks to social media, some of them are breaking barriers.

One good example of this positive change is Laith Ashely. He’s a gorgeous trans male model who has a lot of following. However, in mainstream media, their representation is still lacking.

Why Some Don’t?

Sadly in Asia, most especially in the Philippines, transgender men are still portrayed comically. This is why a lot of ladyboys are reluctant in dating them. Added to that, people from Asia religiously follow tradition. Part of this is the reason why ladyboys only date “traditional” AKA cisgender men.

Others simply are more sexually compatible with cisgender men because of how the natural penis works. They like everything about it so much that it can get in the way of ladyboys having a chance to date trans men. This goes the same way for some transgender men preferring the “natural” vagina.

Why Dating Trans Men is Promising?

For ladyboys, the opportunity of dating a trans man shouldn’t be missed. The reason being is because, like them, trans men know what it’s like before and after transitioning. They know how it feels like to be made fun of, looked down upon, and underestimated.

Most transgender men are more sensitive to the feelings of ladyboys. They understand them more most especially if they’re undergoing HRT. When it comes to relationships, compatibility is very important.

Famous Trans Couple

A well-known trans couple is Katie Hill and Arin Andrews. Their love story was even published in UK’s Metro newspaper. They started dating as trans teens and are still together after gender reassignment surgery. In an excerpt from the newspaper interview:


“I don’t think anyone unless they know our story would come to the conclusion that we’re a trans man and a trans woman dating–They would just see us as a boy and a girl dating.”


“I’ve always loved women and liked women as a female because I’ve always deep down known that I was straight male.”

How to Find a Transgender Man to Date

My Ladyboy Date is the first decent dating website for ladyboys and the men who love them. This means that some of the male members are also transgender men. However, there are also other avenues to find them such as Facebook groups and other dating sites.

trans man in the shadow

Now, if you’re a single ladyboy who’s considering dating a trans man, you must create a My Ladyboy Date account. Who knows, you might stumble upon a pleasant surprise!

Posted in Ladyboys, Love & dating

About the author

Amanda Valentine Dela Cruz
Just a random trans woman playing with makeup and skincare. Loves bacon and the operating table. I'm also the author of the dating guide book Dating Transgender Women for Gentlemen. Know more ->

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