Why Middle-aged Men are Infatuated with Thai Ladyboys

When a young western man puts on a dress and applies thick layers of make-up, he usually looks like a bloke in a frock. In fact, that’s exactly what he is – right? Or he could be mistaken for a circus clown! But when a young Thai guy does the same, he can, and often does, look like a beautiful young woman. In fact many of them can be very passable at a glance, even to a well trained eye. But SHE is still a HE no matter which way you look at it. Isn’t he?


Sweet Ladyboy Lips


There are ladyboys all over the world, but but when it comes to pure beauty and exaggerated femininity, Thailand wins hands down every single time.

That’s never a Guy! Is it?

First-time visitors to the country will disbelieve their guide’s information that they are looking at someone who was born a male.

It’s only upon closer inspection that they realise they’re looking an individual who really does deserve the title of third gender. In other words they’re half man, half woman +1. Generally speaking though, most ladyboys see themselves as female, even though many of them are still packing an handful of tackle inside their silk panties, albeit flattened down by parcel tape!

How do you know if she’s a he?

Seasoned sexpats and regular tourists to the country become adept at spotting most ladyboys. The biggest give-away signs are larger hands and feet, Adams apple (unless they’ve had it shaved), and or course the voice. With the best will in the world, the majority of ladyboys cannot make their voices sound convincingly female. Oh, and not to forget the way they carry themselves. Here are a few more ladyboy pointers for the rookie traveller:

  • Broad shoulders and narrow hips
  • Bigger veins visible on hands and arms
  • Exaggerated walking (often a strut)
  • Top heavy breasts
  • Generally taller than the average Thai girls
  • Overly confident (chatty) towards strangers

What kind of Men Date Thai Ladyboys?

Man holding ladyboys handAlas, many of Thailand’s ladyboys find it hard to get regular employment. Despite the so called ‘tolerance’ towards them, most are still looked down on by Thai society and miss out on so many occupational opportunities (including graduates), when compared to their heterosexual and homosexual counterparts.

What this means, is that some of them (but not all), find themselves working in the sex industry at some level. For many, this is where they find their dates. The main clients are Thai men (of all ages), and Western tourists, especially those men of middle age and older, who become smitten with ladyboys.

Your average Thai male is very discreet about paying for the sexual services of a ladyboy, whereas a lot of foreign tourists are quite open and proud about having a ‘girlfriend experience’ with cute men in skirts. That said, it’s unlikely many would take one home to meet their mum!

Are Men that have Ladyboy Girlfriends Gay or Bisexual?

Bisexual symbolIf you ask any man that has had, or is having, a ladyboy experience, he will almost always tell you he is neither gay nor bisexual. This is something that many red blooded heterosexuals are unable to understand. After all, as beautiful as Thai ladyboys are, most will still have their meat and two veg swinging in the wind after lights out. So one can’t help but wonder what a ‘straight man’ is thinking of when it comes to his moments of so called heterosexual intimacy!

Middle-aged men who date ladyboys often point out that it’s their womanly characteristics they’re so attracted to. They think that if they tick enough boxes, then it’s makes their choice of mate a good partner for their hetero needs. A straighter than straight man might say; “Why not just date a ‘real’ woman?”. This is one question we were unable to find a “straight” answer to.

Note: In defence of those men that lust over ladyboys, any “openly gay man” will tell you that homosexuals have no interest at all in any kind of intimate relationships with transgenders.

Click the images below to see if you can grasp where lovers of ladyboys are coming from ๐Ÿ˜‰

Teenage Ladyboy Sexy Ladyboy Sweet Ladyboy Cheeky Ladyboy Miss Tiffany
Cute Thai Ladyboy Sexy Thai Ladyboy beautiful Thai Ladyboy Cheeky Thai Ladyboy Miss Tiffany Ladyboy

Ladyboy lovers argue that some of the best looking women in Thailand are in fact men!

Aren’t Thai Ladyboys actually called Kathoeys?

Ladyboy, or shemale, are general terms used to describe any male-to-female transgender person, whether they’ve progressing – or have gone all the way and had the full cut-and-tuck under the surgeon’s knife (Thailand’s surgeons are notorious for their expertise in this field).

There are basically 3 stages of transition before becoming a full-blown Katoey. All have their own title distinguishing each phase of their development. First we have the Femboys.

Thai FemboyThe Femboy: This is typically a young boy or teenager who displays extensive feminine qualities. He may or may not dress as a girl but most do wear makeup (even to school if permitted). He will like pretty colours and cute girly accessories. The majority of femboys are actually ladyboys in the making. A few of them will even have gay boyfriends until such times that they become ladyboys.

Once old enough, a femboy will take female hormone tablets. These make his skin smooth and hairless. He’ll also sprout small hormonal breasts with puffy nipples, much to his delight.

Thai LadyboyThe Ladyboy: Once the transition from femboy to ladyboy begins, so do the feminising medical procedures start to kick in as our man begins his real transition into the third gender. He will most likely invest in breast implants, silicone injections, Adam’s apple reduction, along with nose, chin, and hip enhancements. All this and more is his attempt to release the woman he feels is trapped within.

Note: Thai Plastic Surgery Clinics are all over Thailand, some great, others a bit hit and miss. Those that can afford it will go to one of the top hospitals in Bangkok, but there are much cheaper clinics dotted all over the country. More important than the hospital though is the surgeon, and the best cosmetic surgeons catering for katoeys might not necessarily work in the 5 star hospitals.

Thai KatoeyThe Katoey: The third and final stage of completion into womanhood is the Katoey. They have already created an appearance that makes them every bit the women they want the world to see them as. But before they can become katoey’s they need genital reassignment surgery in order for them to feel whole. Physically, this is as far as they can go to fulfil their dream of transforming from male to female.

Tolerated but not Recognised – A Sad Fact!

Even after Thailand’s Kathoeys have got rid of the plumbing, they are still not allowed to change their legal sex under current Thai law. There is a continual movement to try and amend this somewhat harsh take on gender change. At the time of writing this piece the campaigners seem to be no nearer towards getting the acceptance they so desire.

Where do Ladyboys get the money for Costly Surgery?

Money for Cosmetic SurgeryThailand’s cosmetic surgery is renowned for being extremely good, and incredibly cheap when compared to the west. Even so, it’s still out of financial reach for many femboys looking to transform into Ladyboys, and ladyboys into Katoeys. A lot of their funding comes from what they call sponsors. A sponsor is usually a well off middle-aged man, or older, who is happy to pay for all such surgery for as long as the relationship lasts.

Financial Benefits from Mutual Relationships

Unfortunately, most of these older boyfriends get bored and move on to younger partners once their ladyboy friend reaches a certain age and their youthful looks go from pretty to attractive, to masculine. Some might even say, once a sex tourist, always a sex tourist, meaning a long term and meaningful relationship is but wishful thinking with most of these guys. But even though these men might not make the best ‘boyfriend material’, these arrangements (for want of a better term), usually serve some mutual purpose for both parties for as long as they last.


Although a fair number of Thailand’s poorer ladyboys work in the sex industry – whether that’s in the bars, massage parlours or on the streets – it’s wrong to assume this is the norm. And even those who do, to think they’re bad people is just plain wrong. By nature, most ladyboys (irrespective of occupation), are naturally very funny, kind, artistic, gentle, and possess the same unique qualities as all other members of Thai society.

And finally, even though we’ve used the word kathoey here so we can define the various stages of transition from male to female, it’s important to point out that the term “kathoey” could – depending on context and tone – be construed as pejorative, especially in the form “kathoey-saloey” which has a meaning similar to the English language to mean ‘fairy” or “queen.

If you’ve got anything to add to the topic of why so many Farang (Thai word meaning Westerner) men like Thai ladyboys, then please leave your comments below ๐Ÿ˜‰

By Toby Strowger | 50ish Site Contributor
Toby Strowger is a men’s lifestyle writer for 50ish.org

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Readers Comments

    aaron says:

    lady boys are beautiful and I think it makes a much better pair for a man

    Percy Blakeney says:

    Lets ask? Do the katoeys LIKE IT,as much as you ,the General consensus is that They do.,wheras the ladys are Faking it

    Steve says:

    Ladyboys are everywhere in Thailand, and other countries, but I will only comment on Thailand as I know the place, having lived here, retired, for over four years. In that time, I have had relationships with both women and ladyboys, and for myself, I am more committed than ever to a steady relationship with my ladyboy girlfriend. Why, you ask… several reasons, I found women here extremely materialistic, shallow and petty. As a older (64) year old man, you are seen as a cash cow.. the number or early 20’s chicks falling all over you, professing love and long as they got clothes, car, flat and big salary from you, was pathetic, I know the game.. Being bisexual has it’s advantages, and although my first encounters were money based, you have to try before you buy, so to speak… Gradually, as I learnt more about ladyboys and met more, I began to see that not that many worked in massage or bars, like my present ladyboy, she works in a law office and is a accountant, her friends work in offices or chemist’s shops, anywhere you’d find women working. Sure we all go out to a bar, and maybe one might find someone to take home but by and large, they are very discreet and quiet personalities… those over the top ones with their tits sticking out and super short shorts are sex pros… my girl dresses discreetly and smart when we head out for dinner or wherever.. It never hurts to dress well, even when you aren’t out together, keep fit, and be confident…Mine appreciates me in a good pair of jeans, pressed shirt and nice shoes, instead of the usual farang outfit of baggy shorts and T shirts and flip flops..that is very lo so and pure slob in a bar attire..
    We get looks, sure, it happens, my girl is as tall as I, around 178cm and slender, late 30’s and radiates a super confident and open demeanour.. As a couple, we don’t look out of place, I reckon, other then the height, but when you’re sitting down, who notices..
    I think if one is considering a relationship with a ladyboy they have to ask themselves a lot more questions than I want to mention, you really have to think about where you’re going in this world, and who you want to take along, it took me a year to decide, now I have made up my mind and committed, we both are looking to the future together..

      aaron says:

      I love it I too love asain lady boys ,I understand you

        aaron says:

        plus the ess ee ex is way better

    Garlynne says:

    As a White Heterosexual male I reluctantly admit that ladyboys or katoeys are gorgeous and feminine looking. Let’s face it, they have the features and characteristics that fulfill any male fantasy. at least for me they do. But I ponder. I’m not a self-loathing White person. On the contrary. But these ladyboys are more attractive and beautiful looking than 95% of the European females I see and I am making no mistake with my well-honed honesty and eyesight. I have seen many gorgeous Asian and Hispanic women. On average I find them more beautiful than Caucasian women.
    A regular white guy in drag looks like either an ugly woman or a man in drag.

    michael s. says:

    i have seen a lot of photos of lady boys, but have never met one. i do have to admit that i find that the pictures to me, show very beautiful women. being a novice, i wouldn’t be able to tell before getting naked that they weren’t 100% a woman. I look at them as a woman with a tool, not a man in drag. i would certainly not be embarrassed to be out with one and my guess would be that if she got me aroused enough,i wouldn’t be able to say no.

    David Bonnie says:

    A fairly sympathetic article but with some inaccuracies.

    The term Kathoey is the Thai word for ALL Male to female transgender people.
    Ladyboy is a term that Thai Kathoeys accept as a translation of Kathoey to English.

    They use this term in reference to all male to female transgenders no matter what their age of whatever stage they are at in terms of transition.

    Fem boy is a term used most often by western sex tourists for ladyboys with no breasts as yet. It is not a term recognised by Ladyboys themselves.

    Ladyboys may use the term ladyboy or kathoey noi(small) when referring to a young or teenage trans person.

    fedup says:

    My misses is almost 19 stone, 44 years old, nags constantly, dresses like a scarecrow, and does nothing to change her appearance. She breaks wind all the time and thinks it’s funny, smokes, burps, and swears in normal conversation. This is not the woman I married. You could call me anything you wanted to, but I’d swap ladyboy number 3 with my partner of 19 years in a heartbeat. There, I’ve said it, and I mean it.

      Acneface says:

      I wonder what your wife would say about you sir given the chance?

      Thanks – Graham

        David Bonnie says:

        Why do you care what his wife thinks about him? This is not a forum for western wives is it?

        I find it interesting to note that female feminists who insist one must never judge a woman on her looks are often aided and abetted by male feminists who constantly ‘throw their brothers under the bus’ to make favour with women?

        The guy just makes an honest point . . . . .if you had an ugly fat wife perhaps you would feel the same way?

        Chill out man . . . ha ha

          idiot says:

          Lol you’re such an idiot :DDD

          idiot says:

          “Why do you comment then”-comments are idiotic.

      KAT says:

      Then you sir, are GAY.

      nope says:

      You &/or people who are attracted to pretty, feminine, ladyboys, are not necessarily “gay” or “bi”. I believe that we fall under a separate category, ie, we’re attracted to women & ladyboys. Personally I have no attraction to hairy, muscled, hard, chiseled men w/strong chin/jawline. But slim, smooth, soft featured ladyboys,…I find very attractive.

      Gabe says:

      You then married a sloppy woman that doesn’t give a hoot of how she acts and looks. Not all women are like that. I don’t know where your from but I live in Italy and most Italian women take care of themselves, even after years of marriage. Ladyboys may have a beautiful wrapping paper with a pretty bow, but when you unwrap the pretty package, many of them choose to keep their penis to have a little extra something to offer. You may be attracted to the wrapping paper ect but if your also willing to deal with the penis, then that’s fine.

      Niterode Mick says:

      Mate walk away

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