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How is it to date an Asian Ladyboy?

Many male members of MyLadyboyCupid ask us to give them some help with the question: “What is it like to date a Ladyboy?”

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They ask us as they know about our considerable experience and long track record in matching foreign men with Transgender women.

Over the years we have collected numerous stories, vignettes and anecdotes about men using our site to meet and dating Ladyboys. Many of our members have successfully ended up in long-term relationships with Trans women and have shared their experiences with us. So, following is a distillation of some of the information we have been given to help you meet your objectives and make a success of your wish to date a Ladyboy.

Ladyboys are fundamentally women

Remember firstly, though, the fundamental premise about dating Ladyboys: Ladyboys are essentially female. Emotionally female and, in many cases (although some Trans women do perhaps have an additional body part), physically women.

Ladyboys grow up knowing that they are different from other males but often don’t really know why. They may like feminine things, like playing with girls or girl’s toys or, conversely, avoid playing those rougher games boys play. Then, somewhere along the way many T-girls start dressing in female clothes and presenting as young women. Many start taking puberty blockers to avoid enduring the effects of puberty. These effects may include their voices breaking, their Adam’s apple growing and becoming more prominent and facial hair appearing. However, for many Asian T-girls such as Thai Ladyboys or Filipino Trans-pinays, even without puberty blockers, they develop little facial hair.

All puberty blockers really do is delay the onset of puberty to allow the Trans girl a little bit more time to decide if they are going to pursue gender transition. Such a transition can include breast implants and, subsequently, having full gender confirmation surgery to become what many see as a “complete” woman.

Understanding some of the challenges Ladyboys face

Knowing what many Ladyboys go through to get to a situation where they are comfortable with themselves is important for any man looking to develop a long-term relationship with a Trans beauty. It also helps for the man to have some empathy with the challenges Ladyboys have faced to achieve their current status.

If we now come back to the main question in the title: the answer is: “fundamentally the same as dating a genetic woman.”

Many Ladyboys:

  • are looking for a man to love and cherish them; to take care of them when things are not going so well; to share the good times when things are going well;
  • can be jealous, gregarious, shy and yet loving and loyal; it all depends on the character of the T-girls you are dating. This is just like how it would be with a “normal” woman where you have to find out about and know their characters; you will have to gauge what to do/not do or say/not say;
  • can be good or great girlfriends or fiancé’s and wives; they can be fun and adventurous and easily adapt to a new relationship. Most T-girls can run home and take care of the needs of the man they are in love with, as well as working in a career;

Some more sensitive things to know about Ladyboys


  • can be sensitive about certain aspects to do with their past, especially when talking about their early lives when they had to present as male. It is, therefore, important to make sure that pronouns such as “he” or ‘him” are not used when in conversation or correspondence with a Ladyboy. Also avoid using their old male names, which are often called “dead names”;
  • may be very uptight about their penises, if they still have one. Some Ladyboys choose to keep their penises as they are not offended by it. Or they prefer not to have it removed for cost or religious reasons. They may also be able to use their organ in sexual activities to the mutual satisfaction of both parties to the relationship;
  • on the other hand, some absolutely detest their penis, seeing it a redundant part of their body and a sign of their maleness. With such type of Ladyboys it is best to have a frank discussion when the time comes for sexual activities to be considered. Most will tell you if they do not want their penis to be touched or talked about. In fact, with some Ladyboys the prolonged use of hormones beginning from their teenage years makes it not possible for them to get an erection and their penis is, to all intents, flaccid and useless;
  • may not have full transitioned when you start dating them. This may be due to the cost of the surgeries or their age. In many countries, including Thailand and The Philippines, the cost to have compete for gender confirmation is high and many T-girls need to save up for a period of years. It’s best to learn as much as you can about what’s involved in such transition and the stage your new T-girl girlfriend is at. This and your complete understanding will help strengthen your ongoing relationship.

MyLadyboyCupid can offer many more great tips and points of advice about dating a Ladyboy beauty. But you can also learn a lot from your own experiences with one of our Trans women members!

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