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Changed line(s) 221 (click to see context) from:
** Timmy is forced into cleaning Vicky's room while dressed in a maid costume.
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** In "The Switch Glitch", Vicky forces Timmy to shine her shoes, wash her clothes, and [[HomeworkSlave do her homework]], or she will blackmail his parents with a recording of him confessing that he cheated on his math test. To add insult to injury, she puts him in a dress and curlers, which he also detests.
--->'''Timmy:''' I'm not doing chores in a dress!\\
''(Vicky pulls out two tape recorders)''\\
'''Tape Recorder #1''': Hi, I'm timmy Turner, and I'm...\\
'''Tape Recorder #2:''' ...in a dress!
** In "Home Wrecker", Timmy is forced into cleaning Vicky's room while dressed in a maid costume.
--->'''Timmy:''' I'm not doing chores in a dress!\\
''(Vicky pulls out two tape recorders)''\\
'''Tape Recorder #1''': Hi, I'm timmy Turner, and I'm...\\
'''Tape Recorder #2:''' ...in a dress!
** In "Home Wrecker", Timmy is forced into cleaning Vicky's room while dressed in a maid costume.
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* ''Film/LostInAHarem'': After hypnotizing Nimativ with his own rings, Harvey gets him to don women's clothing. Nimativ's not too happy when the hypnosis breaks and he finds himself in the outfit.
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* Creator/RobbieWilliams appears in a [[https://www.youtube.com/watch?v=NwC7ph9FD54 short sketch]] with ''Series/LittleBritain'' characters Emily and Florence, in which they proceed to do this to him when he enters their shop by mistake.
* ''Series/RuPaulsDragRace'': In the OnceASeason makeover challenge in Season 6, the queens had to make over straight grooms into drag brides (while the brides were whisked away to be fitted for masculine tuxedoes). Contestant Joslyn Fox revealed that her partner for the challenge was actually forced into it by his fiancee because she caught him cheating, and this was her idea of making him prove his love for her.
* ''Series/TheToyCastle'': In "Little Red Riding Hood", the Ballerina casts the Goblin as the grandmother in her Little Red Riding Hood play, and makes him wear a frilly nightgown and bonnet, which he is not happy about.
Deleted line(s) 141,142 (click to see context) :
* ''Series/RuPaulsDragRace'': In the OnceASeason makeover challenge in Season 6, the queens had to make over straight grooms into drag brides (while the brides were whisked away to be fitted for masculine tuxedoes). Contestant Joslyn Fox revealed that her partner for the challenge was actually forced into it by his fiancee because she caught him cheating, and this was her idea of making him prove his love for her.
* Creator/RobbieWilliams appears in a [[https://www.youtube.com/watch?v=NwC7ph9FD54 short sketch]] with ''Series/LittleBritain'' characters Emily and Florence, in which they proceed to do this to him when he enters their shop by mistake.
* Creator/RobbieWilliams appears in a [[https://www.youtube.com/watch?v=NwC7ph9FD54 short sketch]] with ''Series/LittleBritain'' characters Emily and Florence, in which they proceed to do this to him when he enters their shop by mistake.
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* ''Fanfic/OniGaShikuSeries'':
** One of Akiyama's clients at Sky Finance wants to open a [[CosplayCafe maid cafe]] in Musutafu, so Akiyama's test for her is to have her manage another maid cafe for a day to see how she handles the position (and [[spoiler:how she deals with creeps or gang members who want to harm her staff]]). Someone has to oversee her obviously, so who do they call? Hana, who is only female employee in Sky Finance? Or Izuku, who is most definitelly a guy but still a growing teenager with a babyface and most definitely not thrilled with the idea?
--->'''Izuku:''' I hope this doesn't awaken anything in me.
** A less comedic and more wholesome instance occurs [[spoiler:after the Villain attack at USJ. Midnight, who saw Izuku acting as a maid for a day during the above incident, drags Izuku after school and teaches him how to do make-up to take off his mind from the sheer anxiety he's been feeling for the past few days. Izuku admits that he feels a bit better after the whole thing.]]
** One of Akiyama's clients at Sky Finance wants to open a [[CosplayCafe maid cafe]] in Musutafu, so Akiyama's test for her is to have her manage another maid cafe for a day to see how she handles the position (and [[spoiler:how she deals with creeps or gang members who want to harm her staff]]). Someone has to oversee her obviously, so who do they call? Hana, who is only female employee in Sky Finance? Or Izuku, who is most definitelly a guy but still a growing teenager with a babyface and most definitely not thrilled with the idea?
--->'''Izuku:''' I hope this doesn't awaken anything in me.
** A less comedic and more wholesome instance occurs [[spoiler:after the Villain attack at USJ. Midnight, who saw Izuku acting as a maid for a day during the above incident, drags Izuku after school and teaches him how to do make-up to take off his mind from the sheer anxiety he's been feeling for the past few days. Izuku admits that he feels a bit better after the whole thing.]]
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* ''WesternAnimation/SuperSecretSecretSquirrel'':
** In "Goldflipper", Morocco Mole is reluctant to go along with Secret's plan for them to crossdress as [[ScoutOut Squirrel Scouts]] to gain access to the titular villain's lair.
** In "One Ton", Morocco Mole suggests that what the titular villain needs is "a mate." One GilliganCut later and Secret Squirrel is dressed as a sexy female panda, with an annoyed expression on his face. However, this trick fails miserably, given that said villain beats him up offscreen pretty much immediately.
** In "Goldflipper", Morocco Mole is reluctant to go along with Secret's plan for them to crossdress as [[ScoutOut Squirrel Scouts]] to gain access to the titular villain's lair.
** In "One Ton", Morocco Mole suggests that what the titular villain needs is "a mate." One GilliganCut later and Secret Squirrel is dressed as a sexy female panda, with an annoyed expression on his face. However, this trick fails miserably, given that said villain beats him up offscreen pretty much immediately.
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[[caption-width-right:350:Now, let's get you ''dress''ed!]]
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[[caption-width-right:350:Now, let's get you ''dress''ed!]]'''dress'''ed!]]
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* GenderFlipped in ''Manga/OuranHighSchoolHostClub'' when the boys are quite happy to dress up Haruhi (in men's clothing, making it this trope, as well as women's).
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* GenderFlipped [[GenderInvertedTrope Gender Inverted]] in ''Manga/OuranHighSchoolHostClub'' when the boys are quite happy to dress up Haruhi (in men's clothing, making it this trope, as well as women's).
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* ''Literature/NorseMythology'': To retrieve his signature hammer from Thrym, Thor is forced to disguise himself as Freya, as Thrym agreed to return the hammer in exchange for Freya's hand in marriage. Thrym, and indeed the entire wedding party, end up dead as a result.
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** Possibly an inversion: [[Franchise/{{Shrek}} Wolfie]] is a cis man who loves wearing dresses, but as a child he was misdiagnosed as trans female because of it.
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* Wilbur is the victim of this during the ''WebVideo/SMPLive'' [[Recap/SMPLiveReunion Reunion]] when Connor has the idea to make him work as the "waitress" at Schlatt & Co.'s new "Connor Esports Bar and Grill (With Women)". It ends badly.
--> '''Wilbur:''' I WAS A WOMAN FOR YOU, CONNOR!!
--> '''Wilbur:''' I WAS A WOMAN FOR YOU, CONNOR!!
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--->'''Foghorn:''' ''(muffled because his beak is tied)'' But I'm a rooster!\\
'''Bantam:''' Don't let it bug ya, man. Like, uh, we can't all be perfect.
'''Bantam:''' Don't let it bug ya, man. Like, uh, we can't all be perfect.
