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Why Having a Ladyboy Girlfriend is Fun

There are plenty of joys in the world. One of the most untapped ones is the joy of having a ladyboy girlfriend. If you’re new to this type of dating, stick around. You will discover why a lot of men are choosing to build their lives with ladyboys.

Please know that this guide was not created to compare trans and cisgender women. This was only created to highlight the positive experiences of men who are dating ladyboys.


Transgender women and cisgender men don’t share a lot mentally, emotionally, and physically. However, they have a lot of similarities. This is because, at some point in their lives, they’ve experienced the same situations.


Most ladyboys did not live their childhoods according to the gender they presently identify with. A lot of them have been raised as “boys” because genders are usually assigned at birth. This is why their childhood is pretty similar to cisgender men’s.

gameboy advance

You’ll probably have fun going down memory lane because of the similarities. After all, empathy is the best way to touch another person’s heart.


This may be up for debate but generally, a lot of ladyboys, most especially the ones born in the late ‘80s and early ‘90s are into video games. The reason being is because they were reprimanded for trying to play with the following things:

  • Dolls
  • Makeup
  • Dresses
  • Gowns and other “feminine” toys and hobbies

Added to that, a lot of them were subject to “boy” games and activities growing up. This is why many ladyboys still like sports and other “boyish” stuff. This is not to say that the majority of them will shoot hoops with you. After all, each ladyboy is uniquely interesting.


Many ladyboys present themselves in a very feminine way. However, beyond the façade, a lot of them share the same interests with cisgender men. Not a lot of ladyboys think of having a family and many of them have the luxury to design their lives.

working in a car

This is why most of them are successful in their career endeavors. Because they don’t have familial obstacles blocking them from their goals, they are more focused on what they want.

You see, a man is usually the one who provides. Not a lot of men are tasked to take care of the home and the children. This is why they have a lot of time and opportunities in reaching the heights of their career. This is not to say that cisgender women don’t make effective entrepreneurs or career people.

It all boils down to similarity and parity. Together, a cisgender man and a ladyboy can be an unstoppable tandem.


If ladyboys are not taking risks, they won’t be able to express their gender identity. Because society still imposes many negative connotations and fewer opportunities for ladyboys, it’s very brave to be one amidst the impending challenges.

Just by being herself, it already says a lot about how adventurous she is. If you want to be with someone with who you can explore uncharted waters, a ladyboy girlfriend is for you.


There are a lot of traditional ladyboys. However, most of them are quite open-minded. If you are into a certain lifestyle or a specific way of romantic expressions, a ladyboy will be the last one to judge you.

cartoon bubble

They are still being judged harshly up to this day. They know how it feels and can empathize first-hand to be counted out. This open-mindedness doesn’t only touch the said bases. It can be fundamental in having a harmonious relationship for a lifetime.

If you are with an open-minded person, you will not feel like you’re walking on eggshells. You will be able to say or do whatever you want without fear. You will also have more freedom in following your preferred path.

No Judgment

If you are constantly being contradicted and judged for your thoughts, dating a ladyboy can be refreshing. Not to say that cisgender women judge a lot. To further expound on what this means, you have to understand a ladyboy’s life.

nice couple

In the east, whereby tradition and old-beliefs are revered, it’s very hard for ladyboys to soar.

  • They immediately get judged even before they get to the doorstep
  • A lot of them are not allowed to express their gender identity in school
  • Many of them don’t get hired by companies simply because they are ladyboys
  • Most people reduce them to be prostitutes or online beggars
  • A lot of people find trans-attraction and trans-relationship weird or just a phase

Because of this harsh reality, they’ve learned not to judge someone easily. This must stop because just like you, they’re normal human beings. They have dreams, aspirations, and standards.

Why would they judge you when in the majority of their existence after coming out, they’ve been constantly judged?


Now, if you’re someone who enjoys sex out of the box, dating a ladyboy might be for you. Many ladyboys are quite adventurous when it comes to sex. Not because they belong in the tabooed category but because of their open-mindedness.

couple on a bed

Added to that, they share the same genitals and know first-hand how to give such the pleasure it needs. However, when you’re talking to a ladyboy, don’t open this topic up in the beginning stages. She might get offended.

Not all ladyboys are into kinky sex. Also, don’t forget to be mindful of how you talk about sex with her. She is not Jezebel. She’s not your fantasy fulfiller nor your sex toy. Many ladyboys are uncomfortable with having “male” genitals. Don’t assume her sexual role from the get-go.

My Ladyboy Date

Always remember that everything written in her is based on general information. At the end of the day, each ladyboy is unique. Keep in mind that just like any other woman, a ladyboy is the same. Certain nuances can be exciting but don’t reduce her to something else.

couple on a bed

If you want to find ladyboys who are looking for true love and a real relationship, you must have a My Ladyboy Date account. My Ladyboy Date is the first decent dating website for ladyboys and trans-attracted men. Signup today and see what Cupid has in store for you!

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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