See, I vote 'YES' because if you break down the definition I think it fits.
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a person and especially a male
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Not required to be, but he is...check!
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who adopts the dress and often the behavior typical of the opposite sex
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Here's where it gets fuzzy. Does makeup fall under 'dress'. Personally I think it does. The person in question is not a goth, hipster, or anything like that, and its not black nail polish. Hes a somewhat normal average male, tshirt and jeans kinda guy.
So in my opinion this is also a big...check!
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especially for purposes of emotional or sexual gratification
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Its not sexual gratification, at least I dont think thats why he does it. But I would say it falls under emotional gratification. People do things that make them happy, if this didnt make him happy, then I would agree he ist.
And once again...check!
So there ya go, he meets all 3 requirements of the definition.
Houdini, what do your psych books define transvestite as?