Trans-pinay in The Philippines: “Challenges” and “Blessings”

If you speak with any of the Trans-pinay from The Philippines with profiles on DateLadyboys, they will probably tell you that their lives are full of contradictions.

Along with Ladyboys from Thailand, Trans-pinay represent the most visible group of Transgender women in Asia, if not the world. The fame and reputation of beautiful, sexy Trans-pinay is far-reaching. Almost without exception, foreign men long to meet such an attractive T-girl. Of course, with the proliferation of dating sites like DateLadyboys, it’s now easier than ever for a man in, say, the US to chat with and “internet date” a Trans-pinay in Manila.

Perhaps more so than their Ladyboy counterparts in Thailand, Trans-pinay from The Philippines have their own unique set of circumstances to contend with. Some of these circumstances are to do with the colonial history of The Philippines over the last 500 years or so, and some are societal.

Trans-pinay have a lot to contend with

In fact, some of the issues Trans-pinay have to contend with can be neatly divided into two parts, namely what we can call: “Challenges” and “Blessings”. There are more items that can be listed under each heading but let’s focus on the key ones for now.


  • perhaps the biggest challenge to Tran-pinay and to all people who fall under the LGBTQI category is the Catholic Church. Its outdated dogma on issues ranging from sexuality to gender, to marriage/divorce and procreation is a problem to many. The Church’s narrow mindedness is contrary to the tolerance it is supposed to be preaching.

Yet over 80% of all Filipinos are Catholic, a throwback to living under the Spanish colonizers for over 400 years. Therefore, the Church have a dominating grip on society, its attitudes and outlook. Not to mention the vast riches it still collects from the people due to the control it exerts. Trans people, Trans-pinay and anyone one who is different or in a minority are generally ostracised and unwelcome;

  • at the end of the day, Trans-pinay are from Asian families. Pride in and expectations of a son are enormous. He has a lot to live up to. Many families have a seriously hard time coming to terms with the fact that their, possibly only son, is feminine acting and Transgender. The pressure on a fledgling Trans-pinay to conform are enormous.

Sometimes “deals” are made whereby a son will act as masculine as possible through high school to get his grades and maybe a Bachelor’s degree. Then he can live as a Trans person as he was meant to be. Often Trans-pinay will overachieve academically to compensate for their femininity or to show their parents that they are “worthy”;

  • amongst male societies in Asia, the Filipino males are high on the list of the most macho acting. The indulge in guns, fast cars and plenty of extra-marital affairs to “prove” their virility and so on. It’s really hard for a Trans-pinay to be strong enough to not participate in such behavior. And if they don’t then they have to face a barrage of taunts and prejudices;

Trans-pinay have certain key advantages

Yet, when we look at the Blessings, it’s clear that Trans-pinay have several key advantages over others, especially non-Asian, Transgender people:

  • typically, Trans-pinay have a relatively slight, feminine build. Once they start wearing women’s clothes and using make-up it is really hard to distinguish Trans-pinay women from genetic women;
  • with high cheekbones and smallish faces, certainly to most foreign men, Trans-pinay are seriously attractive. Long dark hair, full lips and svelte bodies all make up quite a “package” which many men find irresistible. Indeed, it’s often said that the most beautiful women in The Philippines (and Thailand for that matter) are Transgender women. For some reason, many Trans women generally seem to be taller, slimmer and more desirable than natural Filipino women. You only have to look at the cabaret shows or beauty pageants to see why;
  • Trans-pinay, by and large, speak very good English as the language is taught almost from day 1 in most schools. It is the second nationally recognized language. The command of English helps greatly when Trans-pinay are looking for a foreign man from UK or Australia or elsewhere;
  • Filipinos, and by extension, Trans-pinay are naturally gregarious and outgoing. More so than a lot of their Asian “cousins”. Their familiarity with many western ideas and outlook results from the fact that the US also colonized The Philippines for some 50 years in the last century. Therefore, the combination of a beautiful, Asian looking Trans-pinay with the English language is very appealing. Plus, Trans-pinay have a reasonable knowledge of western culture, so it’s no wonder they are in high demand by foreign men looking for Transgender woman to date or possibly marry.

It’s very apparent when looking through Trans-pinay profiles on DateLadyboys just how beautiful and well educated many such girls are. In terms of success stories of Asian Trans women having long-terms relationships with foreign men, Trans-pinay lead the rankings!