History Main / CreepyCrossdresser

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.
18th May '16 11:39:02 AM TheOneWhoTropes
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* In ''Film/DeathWishVTheFaceOfDeath'' one of the villains is Fredrick "Freddie Flakes" Garrity ([[SuspiciouslySpecificDenial not at all played by Sid the coroner from]] ''{{CSI NY}}''), a high-priced mob assassin (nicknamed because of his frequent dandruff) who not only crossdresses during one of his schemes, but later, when hanging out with his girlfriend, comments her shoes, saying he can't wait to see how they fit. (He also has what is quite possibly the stupidest death of the series, immolated by an exploding soccer ball).

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* In ''Film/DeathWishVTheFaceOfDeath'' one of the villains is Fredrick "Freddie Flakes" Garrity ([[SuspiciouslySpecificDenial not at all played by Sid the coroner from]] ''{{CSI NY}}''), ''Series/{{CSINY}}''), a high-priced mob assassin (nicknamed because of his frequent dandruff) who not only crossdresses during one of his schemes, but later, when hanging out with his girlfriend, comments her shoes, saying he can't wait to see how they fit. (He also has what is quite possibly the stupidest death of the series, immolated by an exploding soccer ball).
10th May '16 5:02:34 AM erforce
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* In ''Manga/MyBrideIsAMermaid'', Both Sun and Lunar's fathers try to get to know their daughters a little better by exploring some research into teenage life (I.E: they explored a goofy DatingSim). The end result completely horrifies ''EVERYONE'' else, especially the two girls. Seeing the anime equivalent of the Film/{{Terminator}} wearing a sailor fuku is not a pretty sight. Funny, but not pretty.

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* In ''Manga/MyBrideIsAMermaid'', Both Sun and Lunar's fathers try to get to know their daughters a little better by exploring some research into teenage life (I.E: they explored a goofy DatingSim). The end result completely horrifies ''EVERYONE'' else, especially the two girls. Seeing the anime equivalent of the Film/{{Terminator}} Franchise/{{Terminator}} wearing a sailor fuku is not a pretty sight. Funny, but not pretty.
5th May '16 2:50:17 PM TheOneWhoTropes
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* Either Zepar or Furfur from ''VisualNovel/UminekoNoNakuKoroNi''. One is female and one is male, but as for [[http://media.giantbomb.com/uploads/3/39130/1230766-29ynxoo_large.png which]] is [[http://media.giantbomb.com/uploads/3/39130/1230765-ezn7h4_large.png which]]...

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* Either Zepar or Furfur from ''VisualNovel/UminekoNoNakuKoroNi''.''VisualNovel/UminekoWhenTheyCry''. One is female and one is male, but as for [[http://media.giantbomb.com/uploads/3/39130/1230766-29ynxoo_large.png which]] is [[http://media.giantbomb.com/uploads/3/39130/1230765-ezn7h4_large.png which]]...
18th Apr '16 6:27:27 PM SomberCaelifera
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*** In an effort to help Buster overcome his low self-esteem and be more assertive with his mother, Tobias dresses up in Lucille's clothes; including her underwear. It [[RuleOfFunny doesn't even]] [[MakesJustAsMuchSenseInContext make sense in context]].

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*** ** In an effort to help Buster overcome his low self-esteem and be more assertive with his mother, Tobias dresses up in Lucille's clothes; including her underwear. It [[RuleOfFunny doesn't even]] [[MakesJustAsMuchSenseInContext make sense in context]].
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