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reverse transvestite 

A woman that dresses garishly and applies so much make up that she resembles a Transvestite.
Orange seems to be the colour of choice in the reverse transvestite community this season.

Transvestite

Someone who cross-dresses, i.e dressing outside of gender. Sometimes done to look like a convincing member of the opposite sex ("passing"), sometimes not. Sometimes a secret, sometimes not. Nothing to do with sexuality. Not necessarily to do with desiring a sex change either.
I can't believe there is no definition for transvestite on urban dictionary! Now's my chance...

John: Why is Adam wearing a dress and a wig? Does he want to be a woman?

Carla: No, he's just a transvestite. He likes to cross dress.
Transvestite by Fen_94 December 21, 2012

sweet transvestite 

"Don't get strung out by the way I look/Don't judge a book by its cover/I'm not much of a man by the light of day/But by night I'm one hell of a lover."

Transvestoon 

A male or female video game toon, that is played by the opposite sex. Eg. Male choosing to play a female toon, or a female choosing to play a male toon.
First used and created by artist Jon Luvelli.
"Mike just roled a transvestoon on WOW, he must either like the way it looks from behind or he just likes playing with barbie dolls."

"That freaked me out when I flirted with that girl online and found out it was a damn transvestoon!"
Transvestoon by David Meyers March 1, 2008

transvestitute 

"Dude, look at that transvestitute on the corner!"
transvestitute by Diana W. May 2, 2006

transvestigation

Looking for signs that a person may be transgender.
A Wendy Williams transvestigation is nothing new.
transvestigation by Kerrsenn October 22, 2019