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Can somebody explain the whole ladyboy thing to me? I mean, why do they do it?
Many of them are just gay, and this is the more accepted way to be gay in Thailand. A smaller proportion are genuine transexuals - that is they have had gender reassignment surgery. And the ones who do that do it for similar reasons that western transexuals do - they feel like a woman in a man's body, and therefore change their body.
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Is there a substantial group of people who actually prefer ladyboys for what they are?
Yes, very much so.
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I've also heard that "ladyboys can get very pushy"... meaning they are very pushy in wanting you to take them home?
Despite their appearance, Ladyboys are men, and therefore are a lot more aggressive than women. More aggressive sexually and more aggressive physically. They are very commonly implicated in robberies and assaults on tourists.