http://kotaku.com/5033618/is-this-the-first-transvestite-game-protagonist

"DS visual novel Ikamono no Jiken: IKATAN ("The Squid Events") features a main character who cross-dresses in order to collection information and new evidence as well as gain new personalities. As game site Insert Credit explains: The hero becomes a member of scenario group "Prawn Productions". As a number of mysterious event unfold, the protagonist must dress as a woman to unravel the story in a series of timed investigations. Breaking new ground — that's what the DS does, you know."

No -- One ( if not more ) of the Leisure Suit Larry games had him stranded on an Island, and he had a full body wax.... shape soap into boobs, and don a dress to sneak by Airport security ( I think -- definitely a guard ).

While minimal --- definitely "crossed" Dressed.

Daisy

Final Fantasy 7
Cloud cross-dresses to get into Don Corneo's mansion as a mistress.

Quote from: Sarrah M. on November 17, 2008, 07:20:20 PM
Final Fantasy 7
Cloud cross-dresses to get into Don Corneo's mansion as a mistress.

And if you get the rarest accessories, the Don finds "Miss Cloud' to be the most attractive out of all the other potential girls.