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This is kinda complicated? I agree there's pressure to signal genderfluid style acceptance virtues, but I personally experienced an actual shift here - I went from viewing it as an expression of weakness to an expression of confidence, at least in some circumstances.
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There's nothing wrong with being attracted to masculine men. theguardian.com/lifeandstyle/2 (HT @AdamCatalyst)
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As in, it's a heavy countersignal. A man who dresses up as a woman but maintains general masculinity (confidence, wanting sex with women), and does not display insecurity about potentially embarrassing clothes, is giving a very valuable signal of social comfort, which is hot.
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Probably this also varies a lot by subculture? In a few cultures I've spent time in, there was a lot of normalized crossdressing that was definitely in no way a paraphilia. I'm sure there exist other cultures in which most crossdressing is driven primarily by paraphilia.
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