History Main / RecursiveCrossDressing

* ''Theatre/ThePhantomOfTheOpera'': This variant occurs in ''Il Muto'', with Christine playing the pageboy, who is dressed as a maid because he's having an affair with the lady of the house and wants to be discreet. In the (thankfully brief) scene we see of this opera, the husband is completely fooled and hitting on the 'maid'.

* ''Manga/SpillItCocktailKnights'' has a chapter where the [[DisguisedInDrag crossdressing girl]] dresses back as a girl to give her male friends Valentine's chocolate so they don't feel bad for not getting any from girls. They accept it in the spirit in which it's given, but tell her that her [[DisguiseNeedsWork she wouldn't be mistaken for a boy]].

--> '''Natalie''': People think I'm a man dressed as a women. But I'm ''actually'' a women who used to be a man, dressed as a man dressed as a women. "Illusions~.''

* "WebVideo/{{Contrapoints}}'': Lampshaded in "The Aesthetic".

* ""WebVideo/{{Contrapoints}}'': Lampshaded in "The Aesthetic".
--> '''Natalie''': People think I'm a man dressed as a women. But I'm ''actually'' a women who used to be a man, dressed as a man dressed as a women. ""Illusions~.''

* ''Manga/SpillItCocktailKnights'' has a chapter where the [[DisguisedInDrag crossdressing girl]] dresses back as a girl to give her male friends Valentine's chocolate so they don't feel bad for not getting any from girls. They accept it in the spirit in which it's given, but tell her that her DisguiseNeedsWork.

* This variant occurs in ''Theatre/ThePhantomOfTheOpera'', with Christine playing the pageboy, who is dressed as a maid because he's having an affair with the lady of the house and wants to be discreet. In the (thankfully brief) scene we see of this opera, the husband is completely fooled and hitting on the 'maid'.

* ''Webcomic/xkcd'' has one non-gender example with convention of furries pretending to be humans.

* ''Series/{{Degrassi}}'''s [[https://www.youtube.com/watch?v=88BlhSp5wig Stuff Clare Says]] video features actress Jordan Todosey playing a UsefulNotes/{{transgender}} boy (Adam), playing a girl ("Clare").

* The YA novel ''Flipside'' begins with the members of a high school drama department discussing ''As You Like It'', a play listed below. The casting director decides to make it one level more recursive by casting a guy as Rosalind and a girl as Orlando. Then the guy turns out to [[WholesomeCrossdresser like wearing a dress]], the girl turns out to [[ConvenientlyCommonKink like guys who wear dresses]], and things get really weird. (And no, this ''isn't'' porn.)

* ''Film/EscapeFromLA'': By the time Snake runs into him again after many years, an old associate of his once known as "Carjack" Malone has since become a transsexual woman called Hershe. The character is played by Creator/PamGrier.

->'''Ronnie Barker''': You'll have to bear with me, because remember, I'm a woman playing a man who is playing a woman. \\
'''Ronnie Corbett''': Oh, at least.

* In ''LightNovel/MayoChiki'' when Subaru is disguised as "his" female cousin Puniru, Usami is not convinced by the ''obvious'' disguise...even though Subaru is actually a girl who regularly pretends that she is a boy.

** There are plenty of women who perform as drag queens. In music, [[Music/ScissorSisters Ana Matronic]] wore exaggerated makeup, as did Music/LadyGaga in her first few years in the spotlight.

* In ''LightNovel/{{Haganai}}'' there's [[spoiler: Yukimura Kusunoki - a girl who pretends to be a boy, but dresses like a girl in order to be more manly. She does not even know that she is female and is convinced that she is a boy, albeit a feminine one.]]
* In ''LightNovel/MayoChiki'' when Subaru is disguised as "his" female cousin Puniru, Usami is not convinced by the ''obvious'' disguise...even though Subaru is actually a girl who regularly pretends that she is a boy.

* Coral in ''LightNovel/UndefeatedBahamutChronicle'' needs to dress as a girl when tailing someone in a different country and later when she's made to act as Lux's bodyguard (in the latter case, to appear less threatening to potential attackers).

* As one might expect, {{Drag Queen}}s are well familiar with this trope:
** "Biologically-challenged" queens, aka [[http://en.wikipedia.org/wiki/Faux_queen faux queens]] or bioqueens, are cisgender women who purposely adopt a drag persona and perform beside "traditional" queens in the club circuit. In music, [[Music/ScissorSisters Ana Matronic]] presents herself this way, as did Music/LadyGaga in her first few years in the spotlight.
** It's not uncommon for a drag queen to impersonate a male artist for a single performance, particularly if he's known for having a larger-than-life stage persona that blurs gender lines in his own way. [[Music/CultureClub Boy George]], Music/{{Prince}}, and Music/MarilynManson are perennial favorites.
** Many closeted trans people (who have to pretend to be their assigned gender at birth) express themselves via drag, {{crossplay|er}} and other such activities which involve "impersonating" a member of their actual gender, if for whatever reason a full-time transition isn't a viable option for them.

* In ''LightNovel/EienNoFilena'' or ''Eternal Filena'', the princess of the fallen kingdom of Filosera is raised and dressed as a man to protect her identity. During the game, she has to sneak away with an all female dance troupe which involves her assuming a female disguise over her male one.

[[folder:Light Novels]]

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[[folder:Literature]]

* Perhaps the most extreme example on this page: In one episode, the main character of ''WesternAnimation/XavierRenegadeAngel'' disguises himself as a businessman disguised as a woman disguised as a man disguised as a SassyBlackWoman disguised as a business man disguised as [[ForHalloweenIAmGoingasMyself himself]]. And this is all in an attempt for him to become normal.