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people used to be less actively weird about it/handwaved it for the sake of comedy.
plus there's been notable crossdressing since Shakespeare's time

oh.
I said 'old' but it isn't even that old
I was watching Johnny Test and someone crossdressed/turned into a girl 4 times across 7 episodes

Have you seen the old like 50s tv shows? The leg contest where it’s all guys in pantyhose and skirts? The old cross dressing world war soldiers pic? I love it, it’s so fun :)

that sounds really fun!
people try to make like we are more 'liberal' and more gay or something, but we had so many gay shit back then, even if it was for laughs, if it was done today, people would complain.
gotta watch more of these stuff now, it's really interesting