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Before we dive in it’s good to know what the term transpinay actually means. Trans-pinay is a local term in the Philippines to address a trans woman from the Philippines. Trans logically is short for transgender or transsexual, while the term Pinay is used locally to address a female. The term transpinay is used all over the world. Not just locally in the Philippines.

The term transpinay explained

So what do we consider a transsexual? Someone whose gender identity does not match with their assigned gender at birth is called transgender or transsexual. These terms are globally accepted terms. On the other hand, Pinay comes from the term Filipina, which is a term used for a woman or girl from the Philippines. So when we talk about Philippines ladyboys we use the term transpinay.

Trans-pinay have been around in society for years and years. In contrast to what many people think, being a transpinay is definitely not a new phenomenon in the Philippines. Brought on by the liberalization of societies in many western countries. And the exposure of young people to the hidden mysteries of the internet and social media.

The Trans-pinay's situation is quite unique

Yet, whilst Trans-pinay share similarities with the plight of Thai ladyboys (katoey) or Indonesia. Owing to a quite special set of factors, in some ways, their situation is rather different.

The Catholic church has a stranglehold hold on society in The Philippines. With over 90% of the population (of over 100 million) following the strict & conservative dogma of the staid institution which is a legacy of 400 years of Spanish colonization. Such dogma discriminates against gay people and, as an extension, ladyboys from the Philippines (transpinay).

TransPinay is a combination of the words Transsexual and Pinay. Pinay is the local term for a female (Filipina).

Once the Spanish left, the country was colonized by the US which led to 50 years of liberalization and exposure to the excesses of American society and the film, arts and culture worlds (not all of those are good!).

So, the end result after colonization? Trans-pinays are tolerated but not necessarily accepted in Filipino culture. Although the acceptance of TS pinay has been on the rise the last couple of years. That is why society is in many ways similar to the situation of Ladyboys in other parts of Asia, like Thailand for instance.


The tolerance for Philippine ladyboys is not just because of the western colonization. In fact, pre-colonisation (as in much of Asia, including India), the so-called "third sex" ie Trans people or Trans-pinay were considered special. They were thought of having greater spiritual awareness. And sometimes even revered for having the attributes of both male and female characters. Therefore it is not strange that there always has been some form of acceptance towards pinay trans people.

Furthermore, The Philippines has no history of criminalisation of homosexuals. And gay men and women have, forever, been part of the fabric of society. Albeit for many years having to adopt a low-key profile. Finally, despite the machismo culture inherent to Filipino culture, the matriarchal pre-colonial roots still stand the test of time. By and large, women are not seen as inferior to men. Indeed, in many instances, women held privileged roles. Like being able to inherit land and the wealth of their forebears. And well as being the driving force behind families and major businesses. So are transpinay considered special? Maybe not as special as before colonization. But nevertheless they are an important part of Filipino culture.


If we then turn to a major question of why so many foreign men like transpinay which they can connect with on ladyboy dating sites such as My Ladyboy Cupid. It is not just that they feel attracted to trans women, but especially Philippine ladyboys. Either when they are in The Philippines or overseas in the US, Canada or Australia. It is clear that a combination of the physical attributes, but also mental outlook of Philippine ladyboys play a big part in this..

Let's look at the physical side of transpinay first. Which appeals to many men looking to date Trans-Filipinas. (There are some generalizations here so please forgive them):

  1. Many Filipino males are relatively slight in stature and overall body build. And Trans-pinay are often blessed with being able to blend in with other females, especially from western cultures;

  2. Facial bone structures among Filipinos are quite similar between males and females. With high cheekbones and similar face shapes. Trans-pinay women are among the most beautiful in the world. Even without any cosmetic surgery enhancements!;

  3. Few Trans-pinay seem to develop male characteristics such as prominent Adam’s apples, broad shoulders or other key markers which suggest they may have been born male;

  4. When many Trans-pinay start taking medication such as birth control pills (for their hormonal content and which many do in their teens). Or begin sanctioned courses of hormones. Their redistribution of fat starts to the hips and thighs. And often natural breast growth follows. This means that their body shape becomes very feminine very easily.

Then there is the mental side. And key attractions of Trans-pinay for potential suitors looking to date Philippine ladyboys. Such ladyboys include:

  • Many Trans-pinay are gregarious and outgoing. Due to having to try harder and get ahead in society. Which - as mentioned earlier - tolerates but not completely accepts them;
  • Many Philippine ladyboy women are educated. And have a degree in marketing or business. Which often leads to good careers;
  • The English language abilities of most Filipino people are first class. Making it so much easier to communicate when you are dating a ladyboy from the Philippines. Or to build a relationship with someone. Whether it be a Trans-person or not;
  • Having been exposed to western (ie US) culture and societal thoughts for over 50 years. Not to mention the huge populations of Filipinos living overseas in most major countries. Trans-pinay are comfortable to meet, date and - where allowed - marry foreign men using Trans sites such as MyLadyboyCupid;


Yes, there may appear to be a contradiction between the conservative society which Trans-pinay grew up in in The Philippines. But the reality is that the people in the Philippines are very tolerance of others who are different in some way. It is very much ingrained in societies in most Asian countries. It's only when religious bodies or dictatorial governments need to exert control that Transgender people and other minorities tend to be more marginalized.

Hopefully, The Philippines can continue to change. And work towards better understanding and support when it comes to Trans-pinays.

Date with Philippine ladyboys online

MyLadyboyCupid is the best site to meet ladyboys from the Philippines online. Do you feel attracted to transpinay women but find it hard to connect with them? No worries. You can sign up for free and start searching for transpinay women on our platform. Over the years we have connected many pinay ladyboys with foreign (mostly Western) men. Some are even married now! Watch the video below to see some of our success stories. Maybe your story will be our newest success story!

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