Skip to content

How to Deal with Shy Ladyboys

Amanda Valentine Dela Cruz
This post was last updated on .

Shyness is natural but some people get to overcome it. It’s rather cute most especially in the beginning stages of dating. However, it can be crippling if you’re planning to take things to the next level. If you’re dating a shy ladyboy, you must know how to penetrate her (figuratively).

Why are some Ladyboys shy?

Shyness is an occurrence to everyone no matter the gender identity. However, you must understand some of the possible determining factors why ladyboys are shy. The reason being is because their shyness not only comes naturally but is harbored through certain circumstances.

ladyboy on a bed


Some ladyboys are naturally shy because, in Asia, it is common for women to be more reserved. It’s not that Asian women have less of a voice. They’re just not as vocal by choice. A lot of Asian women enjoy their feminine energy and this is true for ladyboys as well.


Sadly, in Asia, ladyboys still experience discrimination. This in turn tarnishes their confidence and what drives them to be shy. Discrimination can be traumatizing most especially when done in public. A lot of discriminatory acts are performed for the sole goal of humiliation.

If a ladyboy was shunned away publicly from a place, excluded to join a group, blatantly told she isn’t a woman, etc., her confidence may be badly affected. Don’t pin her shyness against her and learn to be more empathetic when dealing with her.

Lack of Opportunities

When a person’s life is filled with “lacks” and inadequacy, their confidence may seriously be affected. In Asia, a lot of ladyboys are still not allowed to express themselves in order to live a complete life.

This starts with something as basic as education. Many countries in Asia don’t allow ladyboys to dress up as their true gender to go to school. The lack of opportunity continues to go on in the workforce. Not many Asian companies are open to the idea of hiring ladyboys.

How to Communicate with Them

If you are serious with the ladyboy you’re talking to, you must break her shell. Doing so can be risky because you don’t want to end up breaking her core. You must tread carefully and with sensitivity if you want her to open up.

happy couple

Excite her with your world

Even if ladyboys are shy, it does not equate to them being boring. Excite and entice her with the possibility of having a happy life with you. Tell her stories about how her life could be if she were to choose to live with you. Make her feel like she’s secured if you were her man.

Don’t pry too much

When dealing with a shy ladyboy, it’s best not to be too privy about her sex life from the get-go. Not that ladyboys are rigid sexually. It’s just that in Asia, sex is not a common topic to discuss in the first conversation. Knowing her personality and character will be beneficial for you.

Since a lot of ladyboys are conservative, your gentlemanly ways will pay off. Don’t make her feel like you’re only talking to her because you want to get to know what’s inside her panties.

Take things nice and slow

In relation to the sections mentioned above, you must do everything with perfect timing. Timing is the key when it comes to dealing with shy ladyboys. If everything is done in a rush, chances are she will slip away. Don’t intimidate her like that. Just take it easy.

Good ideas to talk about

To clarify what “nice and slow” truly means, below are some topic ideas to talk about. If you’re truly serious with this ladyboy, you must start jotting these down. Don’t miss anything when doing this as this may determine the outcome of your future with her.

Maki and Cyril

What she likes

The list of what she likes can go on forever. This is why this guide was created. For starters, you must know what food she likes, her hobbies, interests, and goals. You may also talk about music and movies but never touch the topic of religion and politics.

Doing so will spark more conversations most especially if you have a lot in common.

What she dislikes

Sometimes, asking this question can go awry. If you truly want to know what she genuinely dislikes, you have to zip it and just listen. Sometimes, in conversation, people tend to influence people of what they dislike. This is the time to listen to truly know her character.

Knowing what she likes is one thing but what she dislikes is more important. The reason being is because you don’t want to end up in this spectrum. Just keep everything chill and let her reveal herself to you.

Bad ideas to talk about

Conversations can sometimes get heated. This is why you must have a list of not to talk about. Apart from religion and politics, there are topics that can turn into arguments and you wouldn’t want that.

proud ladyboy

Overtly sexual stuff

Sex is okay but talking about certain kinks and lifestyles is not. Stuff like the latter can only be discussed if you’re already in a serious relationship with her. A lot of kinks are harmless but can turn off people on a whim. Remember to not talk about this most especially because you’re dealing with a shy ladyboy.

Her social status

For some reason, a lot of men on ladyboy dating sites want to know how much a ladyboy makes. Some of them are also eager in knowing one’s background. This can be normal in certain cultures but this can be offensive to shy ladyboys. They may feel like you’re sizing them up.

Force her to do things

When you talk to her, don’t make her do things that she’s not aware of yet. If she said no once, don’t make her say no twice. Respect her limits and boundaries and she will stay with you.

To summarize everything, dealing with a shy ladyboy requires a good amount of sensitivity. You have to be a true gentleman in order to unlock a shy ladyboy’s heart. Don’t worry, everything will pay off. Just like what they say, patience is key.

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 ->

Related posts


Leave a Reply

Your email address will not be published. Required fields are marked *