read the first few pages (man is this thread long...)
Personally, the only reason I'd chide anyone for crossplaying is if they did a bad job of it (and that goes for cosplaying in general) If anything I have more respect for people who crossplay (provided they put appropriate effort into it) because there's so much more that has to be done when dealing with a costume that's been designed for the opposite gender. (not to mention it's a trot-ton more awkward and uncomfortable if you really go the extra mile with falsies, corset, heels, etc --- THAT is dedication!)
I have met a very few homosexuals who crossplay, but ya know what? they do it for THE SAME REASON EVERYONE COSPLAYS --- that they love the character! Nothing at all to do with their orientation (and more than a few have made some version of the joke "I could _never_ pick up a (gay) guy dressed like this!")
Also, just a fun fact. Go on any major art site like Deviant Art and search for cosplays of any of the main characters from "My Little Pony: Friendship is Magic" and you'll find a large number of guys (especially if you search "Rainbow Dash Cosplay") I'd say it's statistically improbably that all of them are gay (and personally I say "...and if they are, so what?")
Lastly, for what it's worth, I'm Proudly planning ($$$ and time permitting) to Crossplay Rainbow Dash at Dragon*Con this year!
'Bring peace to the lost lamb, grant rest to the fangs of the wolf, and deliver the Hammer of God unto the Devil', - Sister Rosette Christopher, Chrno Crusade
"The bad news is he ended up building the whole rock tower... the good news *gulp* I have a rock tower to knock down..." - Rainbow Dash, My Little Pony: Fiendship is Magic (S03E09)