History Main / CreepyCrossDresser

24th Sep '16 10:31:43 PM ryanasaurus0077
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* Even ''Franchise/PrettyCure'' got in on this, as [[Anime/HappinessChargePrettyCure Phantom, the Pretty Cure Hunter,]] went into battle as Cure Un-Lovely, a Cure Lovely lookalike dressed in [[RedAndBlackAndEvilAllOver red and black]], in one episode.
20th Sep '16 4:40:53 PM Mephistopheles
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* In ''Film/ThirtyOne'', Death-Head wears a tutu.
15th Sep '16 5:32:08 AM MadSpy
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:: Pretty much ''everybody else'' (yes, ''even the '''dolphin''''') is just as grossed out when Ace reveals it, in fact.

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:: ** Pretty much ''everybody else'' (yes, ''even the '''dolphin''''') is just as grossed out when Ace reveals it, in fact.
13th Sep '16 7:29:37 PM whereismytea
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* In ''Manga/Brave10'', one of the [[VillainOfTheWeek villains of the week]] Ishikawa Goemon turns out to be one. Since his whole family was targeted to be exterminated, he had to disguise himself as a girl. TokenEvilTeammate Kamanosuke has also used this to [[WoundedGazelleGambit trick people]] back when he was a bandit.
23rd Aug '16 5:29:30 AM Sinister_Sandwich
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*Dark Sun Gwyndolin from ''Videogame/DarkSouls'' was a male moon god born to a family of sun gods. As the moon is associated with femininity he was raised as a daughter and wears feminine clothing which makes it looks like he has breasts. The 'creepy' part comes from the fact he lurks in a hidden tomb and has ''tentacles for legs.''
20th Aug '16 1:46:40 AM Everdream
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** Team Rocket, most of the time: In Kanto and Johto, Jessie would crossdress as a male (complete with mustache), while James crossdressed as a female at the same time. Perhaps the most disturbing example is the infamous "bikini contest" episode. Amusingly, no reason was ever given why they couldn't just disguise themselves as their own gender.

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** Team Rocket, most of the time: In Kanto and Johto, Jessie would crossdress as a male (complete with mustache), while James crossdressed as a female at the same time. Perhaps the most disturbing example is the infamous "bikini contest" episode. episode, where James has a pair of inflatable breasts that led to the episode being banned. Amusingly, no reason was ever given why they couldn't just disguise themselves as their own gender.
13th Aug '16 8:34:19 PM nombretomado
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* Kefka is the only male character other than Cloud who is allowed to wear the crossdressing items in ''DissidiaFinalFantasy''. Then again, given that in the same game his official preferred weapons are ''flutes'' this might be an invocation of the RuleofFunny.

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* Kefka is the only male character other than Cloud who is allowed to wear the crossdressing items in ''DissidiaFinalFantasy''.''VideoGame/DissidiaFinalFantasy''. Then again, given that in the same game his official preferred weapons are ''flutes'' this might be an invocation of the RuleofFunny.
29th Jul '16 7:22:10 PM Someoneman
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* [[http://megamitensei.wikia.com/wiki/Drag_Queen Undead Drag Queens]] appear as early-game enemies in ''Franchise/ShinMegamiTensei: Devil Summoner: VideoGame/SoulHackers''. You could potentially recruit them, but given that they're of the Dark affinity and you only get the ability to recruit Dark demons quite a bit later in the game, it's not worth it except for OneHundredPercentCompletion. Recruiting one (or getting one through fusion) reveals in the Compendium that they are men who somehow became zombies as a result of their devotion to cross-dressing.
26th Jul '16 8:40:07 PM AtticusOmundson
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->''"How many times have I told that boy not to accept food from mortal enemies out for revenge, disguised as girls?"''
-->-- '''Shoubu's mother''', ''Anime/DuelMasters''

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->''"How many times have I told that boy not ->'''Bugs Bunny:''' Usually, ''([[HyperspaceWardrobe spins to accept food from mortal enemies out for revenge, disguised as girls?"''
change into female garb]], speaking in a feminine voice)'' I play the female love interest.
->'''Kate Houghton:''' About the crossdressing thing: In the past, funny. Today, disturbing.
-->-- '''Shoubu's mother''', ''Anime/DuelMasters''
''Film/LooneyTunesBackInAction''
27th May '16 1:04:25 PM Morgenthaler
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* ''Film/TheBorrower'': Scully escapes from the hospital by assaulting and knocking out the female cop who was guarding him. He ties her up and rapes her before he steals her clothes to walk out of the hospital. He even puts on her underwear and lipstick.
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http://tvtropes.org/pmwiki/article_history.php?article=Main.CreepyCrossDresser