In a nutshell, a ladyboy is a transgender woman of Asian descent, although there are a few nuances between the two. The word itself is pretty controversial, and depending on who you are talking to, you will either be chastised for your insensitive rudeness or just recognized as someone who knows their own tastes.
How do you even define a ladyboy?
The word ladyboy came about as an (somewhat imprecise) English translation of the Thai word Kathoey. The original is used to refer to transgender women as well as a noticeably effeminate gay man. Since Kathoeys have been known in Thailand for ages, the origin of the word is more or less lost in time. Some speculate that it traces back to the Vietnam War, when the American army roamed Thailand beaches and first noticed the “native ladyboys”. Proponents of the theory think this is when the need for an English equivalent word first appeared.
Whatever the history of it, the word ladyboy is not universally appreciated as a legit expression. In Asia and Thailand it is generally okay, while in the western countries it is widely considered derogatory. Through the influence of the internet, it is heavily associated with prostitution and pornography, and there is the eternal question of “Is that person more of a boy or more of a lady?” which facilitates many arguments over political correctness. As stated, though, most Asian people are fine with the word in everyday speech, since it was originally conceived to ease communication with the western world, as long as it is used in polite context. Read an insightful opinion piece about that here.
Ladyboys in Asian countries
If you look at Asian countries as a whole, the word ladyboy has become the most widespread throughout the South East. It is used parallel with the local-specific terms, or as the go-to replacement in conversation with foreigners.
Different Asian countries will have their own different words for this layer of populace, such as “new half” in Japanese, “warias” in the Indonesian society, or “hijras” throughout India. Although all of these can be seen as roughly equivalent with the western idea of transgender, they are not exactly the same.
Simply, the mindset of the people has been much too different throughout history, and this is reflected in small nuances in the language.
Ladyboys in Thailand
The so-called “Land of Smiles” allegedly has the biggest ladyboy population in the entire world, and definitely is home to more of them than some of its fellow trans-supporting countries like Malaysia.
This is not surprising, considering the long-since known and embraced Kathoey aspects of Thai culture. Unlike in the majority of the west, the society in general is much more tolerant of the entire scene and its participants. The prevalent religion in Thailand is Buddhism, which is unbelievably tolerant of people who are different in any way. Here is an interesting read on that very phenomenon: https://www.connectsavannah.com/savannah/why-are-there-so-many-transgender-women-in-thailand/Content?oid=2855178
Another factor that contributes to the wide acceptance is the fact of their Asian heritage. The universally petite build, clear skin, and thin-lined faces make Thai ladyboys and trans women even more feminine, so transitioning is a lot easier, and passing as their “new” gender in general society is a simple feat.
In addition, although there is still some inevitable discrimination, having a ladyboy as a family member or an employee is not considered anything disgraceful.
Ladyboys in the Philippines
The Philippines are a curious mix. The country is prevalently Roman Catholic, but despite that it is notably tolerant towards the LGBTQI+ community, including transgender people and the Kathoey – or, to use the local lingo, the “bayot” and the “bakla”.
The bakla and bayot command a noticeable presence in the public eye and the media scene. Concurrently, they speak rather good English and have liberal access to smartphones, laptops, and other devices, so you can find them in swarms on dating sites aimed at transgender women and those who are interested in them.
Ladyboys in the rest of the world
As we already mentioned, in other places around the globe, the word ladyboy is not used that much as a label for people, as much as it is used as a label for a category on porn sites.
Most notably, in the United States and the European countries, there is a clear distinction between gay men (effeminate or not) and transsexual people, and the terms “transsexual woman” or “transgender woman” are much more prevalent.
Moreover, calling a gay man or trans woman a ladyboy is taken as an insult along the lines of “prostitute” (not to say the more blatant version, ahem), or aims to express the opinion that a trans woman does not pass as a woman in society.
Meeting up and the ladyboy dating scene
So, as you can already infer form all this, if you are interested in dating trannys and want to have a ladyboy encounter, you will probably need to head to Asia for an erotic vacation.
There is a sort of diaspora located throughout Canada, the UK, the US, Australia, and Europe. However, these are a subgroup of Asian immigrants in each territory, so casual meetings are a lot harder than in Asia. On the flipside, it will probably be easier to differentiate them from biological women in a non-native environment, and you can always arrange a new acquaintanceship through a dating app or website.
That said, if you do decide to turn your attentions to the east and look for “natural” meetings, be careful. As a stranger, you make a likely target for ill-intentioned sex workers, opportunists of all kinds, even organized crime operators. Keep a close eye on your surroundings. Keep yourself safe if you go to clubs, bars, or specific “let’s meet up” events. Remember that, regardless of their gender identity, these “special guys” are regular citizens with regular jobs, unlikely to hang around just waiting to meet foreign men.