Gay indentity in pre-modern cultures is a related thread we had recently.
Well, not here. The word “kathoey” is applied to any man who dresses up like a woman. And although I can’t say I’ve conducted any research into the matter, I’ve yet to run into a Thai kathoey who was not gay, although I do know that in the West there are transvestites who are heterosexual. Perhaps that is a cultural thing? I have run into plenty of Thai kathoeys over the years, they’re really very visible. In fact, the long-timers here can usually spot some of the more beautiful ones more readily than can a newcomer, even the ones who have had their Adam’s apples surgically removed but not yet undergone the operation. All of us here have stories about the buddy who comes visiting, only to fall in love with a Thai girl, then is horrified to learn she is a man. Sometimes we’ll tell him, and he won’t believe it. Sometimes we know he won’t believe it, so we just let him find out for himself. A Thai kathoey is usually very beautiful, while most of the Western transvestites I’ve seen just look like men in dresses.
Speaking of transsexuals, that’s a big industry here. It can be done cheaply, and I understand the quality is high. A friend once interviewed for a magazine one of the main doctors who performs the operation. He said that it was not uncommon for him to arrive at his office in the morning to find a Westerner snoozing in front of his door. That’s because the Westerner has just enough money for the flight to Thailand, operation and hospital stay, all of which put together is still cheaper than it would be back in the West.
Both straight-acting and flaming homosexuals are called “bakla” - the former is simply closeted. But you’re friend is right about the propensity of the more effeminate seeking out the straight-acting although you tend to see that in the more mature generation. If you see that at all among the younger generation, there’s an element of economic dependency involved. This is steadily changing, however. You tend to see more and more effeminate couples especially in the urban areas but they still tend to be discrete in public.
In the Thai language, I’ve heard transsexual women are called phuying praphet song, literally ‘woman type 2’. I only recently learned the difference between kathoey and phuying praphet song myself. As we learn to disentangle which phenomena can be read more like “gay” and which ones correspond more to “transgender,” it forces us to ask: How arbitrary are the boundaries of the categories that we draw?
I question what the identification of winkte as gay is based on. Here they’re living as women, behaving in the manner of women, and fulfilling a woman’s role in society, and this includes getting married to men. How is this read as gay? 
If they dated women, now that would be gay. There would be social pressure against winkte dating women in favor of pairing them with men, same as the social pressure against lesbianism.
Hell, trans people in our own times have been pressured by the medical establishment into being hetero, i.e. when MTF transitioned to living fulltime as a woman, she was expected to date only men. If we dated women it could have jeopardized our access to transition. That restriction has been dropped in North America now, but they’re enforcing it in Iran.
There have been turf wars between gay historians and transgender historians over how to interpret historical cross-gender behavior, especially in non-Western societies. From a trans point of view, our trans ancestors have been retroactively classified as gay, which obliterates our historical existence as a people. If all the winkte and similar cross-gender peoples weren’t trans but gay, then where the hell did we come from? We just suddenly appeared out of nowhere in the mid-20th century? No, we have plenty of historical antecedents going back thousands of years.
Yeah, the category of “gay” as we define it may be a recent conceptual invention. But the concept of switching genders has been recognized as such for may centuries. Maybe we in Western culture have a hard time with it because we were taught for so long that it was unthinkable or unmentionable. We didn’t even develop a modern Western vocabulary to talk about it until very recently. But transgender has arrived out in the open now and yall better learn to deal with it cause we are never going back into the shadows again.
By “masculine” are you referring to gender identity? The amount of testosterone a fetus gets before birth has been theorized as a cause of gender identity. But once the baby is born, no amount of hormones–or anything else, for that matter–can alter the gender identity. I got my share of testosterone growing up, it affected me physically, but in my sense of who I am, I turned out feminine just the same.
I don’t think I’ve heard “phuying praphet song” myself, but that’s not surprising, as the topic itself does not come up that often among the people I know. You hear “kathoey” a lot, but obviously no one is checking under the skirt to see which set of equipment one has.
I find this increasingly vexing as I grow older. We’ve got comparatively good historical accounts of transgenderdness and same sex ephebophilia yet virtually zero accounts of gay. Yet everything gets lumped under the gay historical category.
We’re gay. We have no recorded history. We’re not transgender and we’re not ephebophiles. Sucks to be us (or maybe it doesn’t), but there you go.
No it isn’t a recent invention at all, I take that back. I forgot: Plato’s Symposium included a myth about the origin of gay and lesbian sexual orientation that looks quite similar to our modern understanding: Some men want to couple with men, just because they’re made that way. Some women want to couple with women, just because they’re made that way. Other people are heterosexual by nature too. According to this myth, no one chooses their sexual identity, it’s innate. We didn’t just invent this in the middle of the 20th century.
All of this is a whole bunch of supposition based on research that I’ve done regarding historical perceptions of homosexuality, so take the idea for what it’s worth. I would say that there are no historical representations of “gay” as we know it today, because for thousands of years humanity had to reach an uneasy accomodation between natural tendencies and breeding. You can’t afford to let your family/tribe/city/state get out-populated by your rivals, because it almost inevitably puts you in the weaker position (i.e. conquered). Thus, I think you see the attitude of “popping out kids for the nation” while simultaneously being allowed whatever floats your boat in your free time. In Greece, for example, we have record of men who were well known for loving other men over women (see Plato’s Symposium), but they would’ve been horrified if that same man didn’t have a wife. Basically, if it didn’t have a societal purpose (apprenticeship, esprit de corps, etc.), homosexuality was probably considered either pointless to mention (like why we have little mention of women in ancient historical records) or utterly taboo.
It only turns out that in modern times, with population size taking something of a back seat to technological and industrial sophistication, that you see an easing of this traditional situation. Men and women can be non-reproductive, single, or gay as a life-long status while still contributing vital services to their society, a major shift from what was, and I think we’re still feeling our way out into a new role for tendencies that were already around…