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Anyway, as for me, I never got the chance to cross-dress yet. However, I would probably love to do this regardless of what my gender would be (I am currently a biological male, but I have been thinking about eventually getting a sex change, et cetera). Personally, I would probably find it fun to dress up and play the role of both genders at certain points in time.
If that is what makes you happy then go ahead with it.
Just be sure you actually look like a woman and don't look like a man wearing women's clothing okay?
I have known both and if we, the non cross dressing group cannot tell the difference it is really hard to
stay focused on you as a person and not your bra strap falling down your hairy arm.
I think I already do if pants are consired as male clothing and dresses for women Everyone are free to choose their clothes, wear what you want to. If someone don't like idea of a man in dress, that is someones problem, not yours. I as a woman would not wear high heels but if some man finds them cool, why not? Just run into heel store and make your dreams true That is what I tell my hubby to do if he suggest heels for me
From what I have seen, women cross dressing with men's clothes seems to be OK. However men cross dressing in women's clothes looks ridiculous.
It annoys me though when my cousin sister wears one of my brother's hoodies scribbled "DESI SWAG" on it. Women don't know swag .
We do too, bloody knuckles. Lol
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Everyone are free to choose their clothes, wear what you want to. If someone don't like idea of a man in dress, that is someones problem, not yours. I as a woman would not wear high heels but if some man finds them cool, why not? Just run into heel store and make your dreams true 
That is what I tell my hubby to do if he suggest heels for me 
