What’s it like to be a ladyboy/kathoey and why does it matter. These are the two topics I wish to discuss here. Firstly, except for crossdressers, who still look like males wearing a wig and ladies clothing, lady boys are usually very attractive and cannot be distinguished as males unless naked. They’re often some of the most beautiful ‘women’ seen. What is it like to sleep with a lady boy? I do not know personally, but I should imagine that as long as you do not mind anal sex, it should be very similar to having sex with a female. Asian women are notoriously beautiful in my opinion. Would I have sex with a lady boy? Yes, if she were beautiful in my view. Most are amazing.
Does it matter? Only to those who see it as something unnatural. There are many men who marry lady boys. Lady boys, shemales and transgenders are mostly all the same. Cross-dressers usually are not. Thailand seems to have the most, or at least is the most well-known for lady boys. But they are found worldwide.
What’s it like to be a lady boy? Or be with one? I don’t know personally so I became intrigued. Below are a few examples that I found of men’s perspective.
“It’s not too different from dating someone who was born female, or a man for that matter. If she is very convincing in looks you might get some inquiring gazes as people figure out if she’s transgender or not, but that’ll be the extent of it.
Or if she’s less convincing in looks (or sound) and you’re in a tourist area then you may get foreign smart-asses discreetly (or less discreetly) asking if you’re aware that you’re with a dude. They’ll think they’re really smart for having figured that out and that you’ll be either surprised, embarrassed and/or thankful for them telling you that. So, any response that’s not those things will work just fine. Other than that, proceed like you would with any other date.”
“It’s fun! Sexually, provided you love sex with ladyboys, they are a source of great joy. My ladyboy GF takes up the female role in sex and there is really no difference in my experience as a male, except that it’s 20 times more fun. They are quite insecure and tend to be jealous. That is no different from conventional Thai women, just more apparent.
They know they cannot press you to marry her. That is a plus, for those who are not sure about committing. If you GF does not pass 100%, there might be funny looks sometimes, depends on who you hang out with. In my experience, in western countries, my GF always pass well (but not in Thailand). That’s due to the larger builds of many westerners I suppose “
“Some great answers already. Just to add that although I’ve never dated a kathoey/ladyboy, I have known and chatted to numerous Thai transgenders. In my experience and I think most of my friends who live in Thailand would say the same, there are 2 distinct types. The ones who are over the top trying to be feminine and are obvious, also often have had breast implants + sometimes hip and bottom. They also tend to be far more aggressive in the tourist areas, often having a bad reputation. The others are quiet and if in a bar, will be in a bar with mostly females who were born as females. A year ago, I used to go to a bar and regularly played pool, bought drinks and chatted with a charming pretty female. One day, the bar owner’s 7-year-old daughter came in and pointed at her, calling out “ladyboy, ladyboy”. I hadn’t realised and obviously, the bar had realised that I hadn’t too! The non “in yer face” transgenders will be the same as any Thai girlfriends and in passing, lots of folk wouldn’t spot her. By the way, I’ve been in going to Thailand for a long time and normally “spot” a transgender easily. That is not meant to sound derogatory towards transgenders and I apologise if it does (I couldn’t think of another way of saying it!). The quiet kathoey is, near as dammit, (usually) pleasant women. Go for it, but, you will need to be fairly thick-skinned though to ignore comments especially from some nasty tourists! Or go to non-tourist areas.”
“I wanted to be the same as all the other girls. I always felt like a girl.” Rattanarak is now 23, and is one of 24 Thai “ladyboy” stars who have performed in Adelaide and Newcastle. Lorraine Berry asked if she considers herself to be a woman, Rattanarak says: “When I was young I always thought I was a girl in the wrong body. Now I would say I belong to [a] third sex.” This other gender – neither male or female – is increasingly finding acceptance in Thailand and beyond.
Rattanarak says the term ladyboy does not equate to “drag queen”. There is a performative aspect to the way drag artists use dressing up as the opposite sex (often in exaggerated tones), whereas being a ladyboy is a state of being, akin to transgenderism: “We are this way all the time.” Nor is the term, necessarily, derogatory – although it may feel that way to a casual observer. While Thanyakarn Rattanarak, has not undergone gender reassignment, “many change [sex] for relationships or to find a boyfriend easier – much easier than [when you are] a ladyboy”. She has a boyfriend and says they are open about their relationship, although tend not to kiss in public. “Thai culture believes this is rude, no matter who you are.”
Thailand has long been a leader in progressive attitudes towards transgenderism and non-binary gender identities, however, Rattanarak says this applies less in Thai workplaces where her community still struggles for acceptance. They are largely forced to find work in the entertainment and hair and beauty industries, and stories like the Thai airline company PC Air who publicly hired transgender flight attendants are exceptions to the rule.
By Rick Klink