Today We Talk About Ladyboy.

In recent years, I’ve developed a strong passion for Thailand for countless reasons: the climate, the food, the customs, Bangkok itself, the sense of peace, the low cost of living, and of course, the sex industry and its many offshoots. And when it comes to the Land of Smiles, one cannot avoid mentioning Ladyboys. You may like them or not, but they are an integral part of the entertainment scene we enjoy and of Thai culture in general, so it’s a topic that deserves to be explored in more depth.

Before moving on to personal thoughts, let’s start with more technical aspects such as terminology and definitions, in order to better understand what we’re talking about. First, let’s analyze the term Ladyboy — a word composed of “Lady,” meaning “Signora” (Madam), but more generally interpreted as Woman/Female (since “Woman-boy” would sound odd, as would “Girl-boy” or worse “Woman-man” and other awkward combinations), and “boy,” which in English means “young man” but is also commonly used to indicate male/guy in general. So, we can interpret Ladyboy as “Woman-man,” essentially a hybrid between the two main biological sexes.
Not coincidentally, Ladyboys are often referred to as the “third gender” across most Southeast Asian countries such as Thailand, as they typically present characteristics of both male and female genders. (There is also intersexuality as a genetic condition, meaning individuals with mixed sexual traits that don’t fit strictly into male or female categories, but that’s a broader topic not necessarily related to the Ladyboy definition or gender transition, so we won’t go into it now.)
The word Kathoey (also spelled Katoey or Katoy) is often used, and although it’s not entirely incorrect, it’s not quite appropriate to use it when referring to a Ladyboy. That’s because Kathoey is more accurately used to describe gay men who show clear intersex traits but do not necessarily identify as transgender — in other words, they still identify as men, even if they have somewhat feminine features.
There’s a lot of confusion around these terms, and nobody will be offended if you use one instead of another (they might gently correct you if needed), but when in doubt, when referring to Ladyboys, it’s always appropriate and appreciated to use feminine pronouns and terms.

This transition toward what is commonly referred to as the Third Gender occurs primarily through hormone therapy, which is used to modify secondary sexual characteristics. Examples include: breast development, reduction of body and facial hair, increased hair growth on the scalp, accumulation of body fat around the hips, reduction of abdominal fat, and an overall decrease in muscle mass.
In addition to hormone therapy, as is often the case, a Ladyboy may choose to undergo an androgyno-genital reassignment — that is, a vaginoplasty surgery in which the male genitalia are restructured and adapted to closely resemble female genitalia, both in appearance and in terms of sexual pleasure.

–Leaving aside the technical side of the matter we can say that if we talk about Ladyboys there are various “levels of femininity” that can be found at first glance, to put it in simple words: Some ladyboys (especially if they have not undergone any hormone therapy or are not genetically predisposed to resemble a woman, and have not undergone multiple cosmetic surgeries to alter their physical appearance“) are easily recognizable even to an untrained eye because they retain obvious male features, while others are decidedly feminine in appearance and mannerisms and are often even visually more attractive than most women. However, they can be identified by certain “clues” that we will discuss later. Between these two extremes lies the whole spectrum, and it is impossible to list all the possible variations and factors. For example, a physically petite Ladyboy who has had a very feminine face since birth, has undergone hormone therapy developing breasts and other typical female traits, and who perhaps has “unobtrusive male genitalia” can be misleading and leave even the most experienced “expert” doubtful, being mistaken for a biological woman even though officially on documents she is male and between her legs she has a penis rather than a vagina ( i understand that for some people this might seem like an exaggerated statement, but if you think that way, it’s probably because you have never met a ladyboy, or quite possibly you have met one and didn’t realize it).

At this point, it is reasonable to ask how it is possible in such cases to recognize a ladyboy from a biological woman, and in this regard there are some details to notice—clues that are fairly easy to spot:

  • Exaggerated femininity, both in gestures and in the way they carry themselves. Generally, ladyboys tend to accentuate feminine reactions and mannerisms; in some cases, they are even unintentionally caricatural. Watch how they move and pose—that’s a good starting point.
  • Height, Shoulders, Hips. Thais, Filipinos, and Asians in general are not very tall, but women are still generally shorter than men. So, if you see a girl who is around 170 cm (5’7″) or taller, there’s a good chance she might be a ladyboy. Also, broad and sturdy shoulders combined with narrow hips are a strong clue. Although some women have these features, as the saying goes, “three signs make a proof.”
  • Large Hands and Feet are uncommon among women. When you see a girl with large hands, rather long fingers, and shoe size 40 (EU) or above, it’s very likely that she is a ladyboy rather than a biological woman.
  • Jawline and Elbows. A rather large and square jawline is a good indicator of a ladyboy, as are large elbows even on relatively slim arms.
  • Long and muscular legs are not typical of Thai women. It’s not necessarily exclusive to ladyboys, but 9 times out of 10, if the legs look like a man’s, it’s probably not a biological woman.
  • Hair. Thais and Asians in general have much less dense and less widespread facial hair compared to Europeans and other ethnicities, but on closer inspection you might notice some suspicious fuzz on the face, especially under the chin or on the cheeks, which women generally do not have.
  • Clothing and underwear. Generally, Thai women wear a bra, whereas Ladyboys tend not to wear one, at least in informal settings or if they work in the trade. Their clothing is usually very flashy and aimed at highlighting their femininity in every possible way. These are not definitive clues since they can also be seen in biological women, but when combined with others, they can be helpful (though in 99% of cases, if she’s wearing “grandma’s underwear” instead of a thong, she’s not a Ladyboy).
  • The voice is one of the most obvious clues, as in most cases it tends to sound “odd” and somewhat artificial. Often, a laugh can completely remove any doubt because it’s harder to control the tone of voice when laughing spontaneously (although there are also women with a less feminine voice timbre).
  • The “Package.” Obviously, it’s not always possible, but it’s advisable to take a quick look at the genital area because often you can immediately tell if “there’s something extra” for it to be a woman. It’s obvious and straightforward, but simple and effective in some cases.
  • The Vulva. In the case of a post-vaginoplasty Ladyboy, even though the vulva looks just like that of a biological woman, you will generally notice that it is positioned a bit “higher” than normal — in other words, the “hole” will usually be farther from the anus compared to a natural vagina. (Of course, this is something you’ll notice only in intimate situations, so it’s mostly useless to point out beforehand, but it’s worth mentioning because many “novices” haven’t noticed this detail and still believe they’ve had sex with a woman when it was actually a Ladyboy. Not that it makes much difference in practice, but it’s good to be aware of.)
  • Last but not least: If despite everything you still have doubts about the gender of the person in front of you, just ask them politely. It’s natural to have doubts if you suspect something, and if it really is a Ladyboy, everything will go smoothly. If you ask someone who was born a woman, she will probably feel offended. (The choice is yours, but if you have this doubt, it means you like them, and at that point, whether they are a biological woman or not is just a minor detail, considering you’re not planning to start a family but just to have fun; otherwise, you’ve come to the wrong place.)

But now let’s move on to more practical matters. Given that many Ladyboys work in the sex industry, where supply is high because demand is equally high, if you feel attracted to the third gender, it’s important to say that if you like Ladyboys who resemble women more than men (regardless of their biological male birth), it doesn’t mean you’re gay. This is mainly because you are attracted to their femininity, not their male side (even if they have or had a penis like you). If you also like “taking it in the ass” from a Ladyboy, then you’re not straight, but you’re not exactly gay either.
For accuracy, we should also consider those who enjoy the infamous “prostate massage” or simply love receiving a “fellatio with a finger in the ass from the lady who’s sucking them off.” Physically, the line between these preferences is very thin. But nowadays, dozens of labels and acronyms have been invented by the infamous “LGBTYZX+etc” community to classify and “ghettoize” everyone’s personal tastes—ironically contradicting their much-praised slogan “I don’t see differences,” when they are often the first to highlight these differences in well-defined and separate categories.
So pick whichever label you want, if you like—but the important thing is to keep doing what you enjoy. The rest is just pointless detail invented by those who feel uncomfortable with their sexual tastes and feel the need to fit into something. (Maybe they should also learn the way of “live and let live” instead of trying to get attention by imposing their ideas on those who think differently—but that’s another story…)

Fortunately, everyone is free to choose what they prefer, and even among straight people (or those who claim to be), anyone who feels the need to judge others for one reason or another is essentially a frustrated individual who feels the need to emphasize their masculinity because, in reality, they are not man enough to accept other people’s preferences. I can’t speak for others, but personally, I’m not attracted to men or to trans women who look like men or are obviously masculine (and between us, I absolutely don’t feel the need to get my anus deflowered by a penis^^). However, if it’s a Ladyboy who is decidedly feminine or almost indistinguishable from a woman, I’m often as attracted to her as I am to a biological woman I like.
So, if I’m not mistaken, the meaning of homosexual is “sexually attracted to individuals of one’s own sex.” Therefore, since Ladyboys are considered “the Third Sex,” we could say without further doubt that even literally, the definition of gay is far from accurate when a man is attracted to such chimeras, even if they have a penis between their legs instead of a vagina. On the other hand, there are women with masculine traits above average—often even more evident than in many hormone-treated Ladyboys—and many of these masculine-featured biological women are appreciated by straight men or men who openly identify as such. So, if you look closely, we probably walk on a very thin and hard-to-define line in this case as well.
But the absolute funniest thing is that in 2024, we’re still hearing the same bar-talk from 1984, and equally pathetic but amusing is the difficulty many have in admitting that when they see a Ladyboy more beautiful than a woman, they do give it some thought indeed ( but without telling anyone eh, that then someone thinks you are queer fag etc. etc.) And then one evening you find them in the dim light of some venue, when they feel far from prying eyes, with a smiling face while the Ladyboy next to them is playing with their penis. What happens afterward is the usual conclusion (maybe after a couple of drinks when they don’t think too much about appearances or external judgments), no more and no less than what happens with a woman you like and who sexually excites you. Then, of course, there are those who simply don’t like it — tastes differ. After all, it’s also true that not everyone likes the same type of woman: some prefer slim ones, some those without breasts, some with larger breasts, some redheads, some short, some curvy. Maybe someone I find irresistible for some reason might be completely unattractive or uninspiring to you. That’s perfectly normal.
It makes sense that just as I don’t like women who are too full-figured, others might not like Ladyboys regardless — even if they actually can’t tell a Ladyboy from a biological woman. But it’s equally clear that for many it’s a matter of principle, appearances, or fear of judgment from others, because maybe they’re attracted but avoid trying it out due to unfounded fears of questioning their heterosexuality or who knows what else.

To these people I would just like to say, “If it seems like a good thing and it doesn’t hurt anyone, do it.”

–Regarding the “intimate” experience with a Ladyboy, the first time might probably feel strange (slightly less if they are post-op LBs i.e. they opted for vaginoplasty), but it’s less strange than one might think, and deep down, if you find yourself in bed with a Ladyboy, it’s your choice, usually driven by curiosity. Then it becomes a normal kind of fun because, in practical terms (in case you are only the active party as is often the case) it’s like having anal sex with a woman, no more and no less. In fact, you’ve probably done it with women less attractive than the Ladyboy in front of you at 90 degrees. And honestly, for those who have had a penis all their life, it’s not that strange to see another one during sex (or are you telling me you’ve never done a “threesome” or “foursome” with one or more ladies and a friend, or other variations?). One could talk about this forever — everyone has their own ideas and preferences on the matter — but from my personal experience, I can say it’s fun and in some ways even more intriguing with a Ladyboy than with a “biological woman.” This is probably due to the “novelty factor” of the first times, but here we’re getting very personal, and it wouldn’t make sense to go deeper into such a subjective matter.

Let’s conclude with some useful tips regarding professional Ladyboys and similar entertainers in the city with the largest scene in this respect, namely Bangkok:

  • In Bangkok, one of the best spots is the
    Check In Bar
     (C.I.B.), a bar with rooms upstairs for short-time visits (though of course you can also retreat to your own hotel if you prefer). The C.I.B. is located on Soi 10, a side street on the left just a few dozen meters from Sukhumvit. It’s a pleasant bar with two pool tables, one in the main room and one in a smaller adjacent room. Generally, it isn’t too crowded, and there are about fifteen ladyboys of varying appearances. During parties and special events, however, it can get quite busy and lively — a fun chaos. In any case, it’s a good place to spend time without anyone pressuring you for “another drink,” as often happens in most other bars. One of the venue’s main strengths is its relaxed atmosphere: you can simply order your beer and observe the scene, or interact with the ladyboys, of course offering at least one beer to anyone who keeps you company.

Best Go Go Bars with Ladyboys in Nana Plaza:


  • Obsession –
     Probably the largest Go-Go Bar with ladyboys ever, and certainly the most famous in Nana Plaza. The atmosphere is more relaxed than other venues, with plenty of choice and a very chill environment.

  • Wonderland –
     A small venue, mainly catering to an Asian clientele, a bit pushy with the drinks, but with the right company, the fun is guaranteed. It’s brightly lit and the space is limited, so it’s better to go when it’s not too crowded.

  • Strap’s –
     A lively Go-Go Bar with a decent overall line-up.

  • B-52 –
     Small and less frequented, the tail end of the four Ladyboy Go-Go bars in Nana Plaza.

In Soi Cowboy there are two other Ladyboy Bars:


  • Cockatoo –
     The most famous — or rather, infamous — one, but it’s more of a tourist trap compared to those in Nana Plaza. The line-up is average, but the staff is very pushy with drinks and the atmosphere is generally not very relaxed. However, it’s practically the only ladyboy bar in Soi Cowboy.

  • Shadow Ladyboy Bar –
     Until 2019, it was a Beer Bar with girls, then it became the second Ladyboy Bar in Soi Cowboy. The quality of the ladyboys isn’t even close to the most popular venues in Nana Plaza, but although the bar is rather small, the atmosphere is less “pushy” compared to its direct competitor on the same street.

In addition tothese single-issue Bars, it is also easy to meet Ladyboy “tradesmen” in other locations not expressly dedicated:

  • The large cluster of bars located at the beginning of Soi 7, where both girls and ladyboys work together in various pool bars. The aesthetic quality of some ladyboys is such that at first glance it is often difficult to distinguish between the two categories, as many of the “real women” don’t quite measure up. Others, however, can be noticed from afar. In reality, among the many bars side by side without interruption, there are even some women who could be mistaken for ladyboys (it’s hard to explain the situation clearly in words—if you pass by, take a walk through the bars and you’ll understand what we’re talking about).
  • The stretch of Sukhumvit Road from Soi 11 to Soi 15 (especially at night) is lined with attractive ladyboys looking for clients. They usually spot you from a distance, and if your eyes meet, they smile and greet you, offering their company directly. They are also easy to distinguish here because they stand on the sidewalk in flashy outfits, and generally there aren’t many female sex workers along this part of the street.
  • In Soi 4 (Soi Nana) c’è un po’ di tutto, con ladyboy che si mescolano tra ragazze thailandesi e ragazze africane (piuttosto comuni in quella zona dopo il tramonto). Tuttavia, una buona parte dei ladyboy in cerca di clienti si raduna di solito davanti al Dynasty Inn e più avanti, sul lato destro della strada, poco prima di arrivare al Seven Eleven di fronte al vicolo di Soi 6.
  • In general, throughout the Nana area along Sukhumvit Road — from Soi 3 to Soi 11 on the “Arab side” and from Soi 4 to Soi 8 on the opposite side — it’s easy at night to encounter ladyboys looking for clients or sitting at street stalls eating and drinking after 2:00 AM, when the Go-Go bars in Nana Plaza and most other bars start closing. Ladyboys can also be found near Soi Cowboy at night, as well as in the Silom–Patpong area, although that area now offers much less compared to Nana and its surroundings.

Naturally, this is not meant to be an exhaustive guide to the entire ladyboy world of Bangkok, nor of all Thailand or neighboring countries, but the capital is undoubtedly the place with the highest concentration of ladyboys and the best spot to start gaining experience and getting to know this side of the Land of Smiles. Here, interaction with those who belong to the “third sex” is part of the game and everyday life.

So, for now, I’d say that’s all. Maybe we’ll come back to the topic later and talk about other cities as well, like Pattaya, which has a lot to offer in this regard.

Greetings from your Redattore, and see you next time!