Is This The First Transvestite Game Protagonist?

Really, we just don’t know. 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.

『いかもの探偵-IKATAN-』凶悪犯罪が一切起こらない推理アドベンチャーゲーム [Famitsu via Insert Credit]