Anyone who has ever visited Thailand will know about the beauty of Thai women. In their twenties, they are striking. In their thirties, they are looking more mature, but still most are very attractive.
The women working in the ubiquitous bars and massage parlors of Bangkok, Pattaya, and Phuket are mostly former housewives, believe it or not, married but separated, with two kids they left back in their village with their mothers. Most are from Isaan, the North-East corner of Thailand, which has a large amount of poverty. Some are from other parts of the country, especially Chiang Mai and Chiang Rai, and a very few are from Bangkok or central Thailand.
But about 1 in 100 is not a female at all, but a "ladyboy", or katoey in Thai. Quite often, they appear more feminine than the real women. I have seen many a farang ogle and lust after a very sexy woman, not realizing that "she" is a "he".
Like the women, most ladyboys are from Isaan. I have talked to a few on a one to one basis, and asked them when they first knew they wanted to be a female. All said they knew at an early age, around 5 or 6 years old. They said they liked the female manner, didn't like rough sports, were partial to art and music.
Katoeys are an accepted part of Thai culture, considered to be a third sex in Thailand. Several are movie stars and TV announcers. One is a national kick-boxing champion. You will find ladyboys everywhere, working as waiters, store clerks, hairdressers, couriers, etc.
In North America and Europe, a sex-change (also called a gender re-assignment) operation is considered to be a big deal, requiring many months of psychological counseling before the operation to make sure the person is committed to the change.
In Thailand, a sex change operation is quite common. There are several clinics and hospitals which perform it, and the cost is a fraction of what the western charge would be, typically US $ 5000-7000. Nevertheless, for a poor person from Isaan, $ 5000 is a huge amount of money.
There are three main areas in Bangkok where ladyboys are present in large numbers: Nana Entertainment Plaza (on Sukhumvit Soi 4), Patpong Road (off Silom), and Soi Cowboy (close to the intersection of Sukhumvit Road and Asoke Road, which has both BTS SkyTrain and MRT Subway stations).
At Nana, the majority of ladyboys are "pre-op", meaning they still have a penis. At Patpong and Soi Cowboy, most are "post-op", meaning they have had the operation to create a vagina. The operation involves cutting out a section of intestine, which will become the vagina. The penis is cut open and inserted into the intestinal tube; typically some of the scrotal sac is used to increase the length of the new vagina. The tip of the penis becomes the new clitoris, and is normally still sensitive after the procedure is finished and everything has healed. The ladyboys I talked to said they could still have an orgasm, but did not ejaculate.
Scar tissue is visible if the post-op ladyboy retains his / her public hair, but if it is shaved off, it is difficult to tell an artificially created vagina from the real thing.
However, this is typically not the end of the story in sex reassignment. The male body is typically larger than the female, even in Thailand, where many people seem to be 80% the size of western people. The ladyboy has to take hormones for a couple of years before the operation; these hormones help him grow breasts and reduce his facial and body hair growth. Thai men don't usually have much body hair, compared to Western men, but they do have some; hormones or another treatment are needed to reduce or eliminate it. However, hormones have a side effect of reducing the ability to ejaculate.
Males typically have a protruding Adam's apple, so that is yet another operation: it can be shaved by a surgeon to reduce or eliminate the protrusion. And many have electrolysis to eliminate body hair, especially in the armpits.
If you visit Nana Entertainment Plaza after 7PM (which is when it opens), you will find several hair-dressing establishments located on the decks that run around three sides of the structure. The ones at the front cater to the bar girls; the ones at the rear cater to ladyboys. You can watch some of the ladyboys preening and preparing their makeup.
Some of the bars are exclusively ladyboys. If you enter one such bar, you will find that most ladyboys are more than passable and some are strikingly beautiful. I don't think I have ever seen an ugly ladyboy.
As far as relationships go, ladyboys are just like Thai women. They want a long-term relationship, and they will try hard to make the relationship work. Many speak some English, but you really need a product like Speak Easy Thai to help you learn some basic Thai vocabulary. If you can communicate better, you have a much better chance of a lasting relationship.
A part of Bangkok's nightlife that should not be missed by any visitor, ladyboy cabaret shows are professionally done, with spectacular productions (lots of feathers and glitter, good music, and some comedy as well). You can see them at the Calypso Cabaret (Asia Hotel, Ratchathewi SkyTrain station), Golden Dome Cabaret (15 minute walk from Sutthisan subway station), and Mambo Cabaret in the former Washington Theater between Sukhumvit Soi 22 and 24.