Oooo fella's getting emotional now! This really winds you up doesn't it?
I have answered the "how does it hurt you question" - you even replied. Go back and read properly instead of letting your emotions jerk you around.
And no, sadly prejudices do not go away just because we want them to. But with long, hard, often thankless work by rights movements like Feminism, society can change. Yes we still face structural and everyday sexism and racism in the UK, but women are no longer literal property here, and the signs that once told Black people they were not welcome are no longer accepted.
So I'm aghast that you think it because racism and sexist are hard to eradicate we should just leave them unchallenged. These things changed because people did not accept them unchallenged.
And in the same way that just because racism and racial sterotypes still exist, that does not mean it's ok for a white person to express their "Blackness" by wearing stereotypically Black clothes, just because sexism and sexist stereotypes still exist that does not mean it's ok for a male person to express their "Femininity" by wearing sterotypically female clothes.
So sure, wear the clothes if you like them. I'll support any man to do that. But not because they express Femininity. Wear them because you are a man who knows that both Femininity and Masculinity are two sides of the same sexist shite coin and real freedom and acceptance is to realise we are all far more than that.
But if you start to think "hey this dress is good but it really doesn't hang right without tits" and your next thought is not "I'll need to get it altered" but "I wonder how I can get some tits?" - that's the time to take a good honest look at yourself and accept you aren't just a man wearing a dress you like any more, you are a man dressing up as a woman.
Because Women are not a costume. Not for gay men, not for AGP men, not for men who deeply and truly believe something in their minds makes them more like women then men.
These men don't see us. The "women" they want to be, the" women" they dress as, maybe even believe they are, are in reality nothing to do with us and how we actually live our lives. They are just these men's own sexist projections onto us. And as such, we have no moral obligation to indulge their view of us over our own.
But honestly, LOL at academic.
Mate, "academic" is men like you trying to "logically" (and bad logic, I might add) explain to actual women why our own experiences of our own lives don't count. Can't get more "academic" than a man trying to explain the experience of womanhood!
So far I have given you more courtesy than you deserved, frankly because everyone deserves a chance to learn, but the fact is that I've demolished your points even if you are too het up to accept it.
You are not bringing anything new, and I'm bored of you.
Read the board, understand what has already been said, go away and learn something and bring something new. Then maybe you'll be worth my time.