History Main / CreepyCrossdresser

30th Apr '18 4:51:43 PM 8BrickMario
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* Creator/JunjiIto story "Nanakuse Kyokumi" is about the titular author who has a bizarre mimetic influence on people when she makes weird gestures, or "quirks". She also happens to be a man in drag, which makes the protagonist, a fan, upset.

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* Creator/JunjiIto story "Nanakuse Kyokumi" is about the titular author who has a bizarre mimetic memetic influence on people when she makes weird gestures, or "quirks". She also happens to be a man in drag, which makes the protagonist, a fan, upset.
30th Apr '18 4:50:56 PM 8BrickMario
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* Creator/JunjiIto story "Nanakuse Kyokumi" is about the titular author who has a bizarre mimetic influence on people when she makes weird gestures, or "quirks". She also happens to be a man in drag, which makes the protagonist, a fan, upset.
19th Apr '18 11:41:08 AM Pichu-kun
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* In ''Literature/{{Parrotfish}}'', some football players dress up in drag at the start of a game. It's supposed to be funny and is supposedly a long-standing tradition, however Kita finds it an offensive TakeThat against Grady (who is a {{trans|gender}} boy).
6th Apr '18 5:51:39 PM zephyran
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* Elendira the Crimson Nail from ''Manga/{{Trigun}} Maximum'' (the later volumes of the manga), although he or she is most likely a {{transsexual}} woman.
** Given the body-mod capabilities of Gunsmoke science demonstrated in the series, she could be, but could also still be male. Either way, she's scary as hell, one-upped Legato by some way, but was sadly too freaky (as much for the 'fighting style based on graphic impalement with giant red hardware from [[HammerSpace nowhere]]' bit as for the transexuality) to get into the anime.

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* Elendira the Crimson Nail from ''Manga/{{Trigun}} Maximum'' (the later volumes of the manga), although he or she is most likely a {{transsexual}} {{transgender}} woman.
** Given the body-mod capabilities of Gunsmoke science demonstrated in the series, she could be, but could also still be male. Either way, she's scary as hell, one-upped Legato by some way, but was sadly too freaky (as much for the 'fighting style based on graphic impalement with giant red hardware from [[HammerSpace nowhere]]' bit as for the transexuality) being transgender) to get into the anime.



* Fumiya Ninomiya from ''Manga/WanderingSon'' crossdresses just to impress Saori Chiba. While not an outright "villain", he is portrayed as a bit of a slimeball when compared to the actual transsexuals.

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* Fumiya Ninomiya from ''Manga/WanderingSon'' crossdresses just to impress Saori Chiba. While not an outright "villain", he is portrayed as a bit of a slimeball when compared to the actual transsexuals.transgender people.



* Kaito from ''Himegoto - Juukyuusai No Seifuku'' comes off as this at first. He is a man who enjoys dressing up as the woman he has a crush on, a JerkAss who toys with women's emotions, pretended he was gonna rape Yuki, and generally acts manipulative and sly. However, the further the manga goes the more it becomes obvious that Kaito is more likely {{Transsexual}} than just a villainous crossdresser. His obsession with Mikako is creepy, however, a lot of things he does happen out of fear for not being accepted the way he is. The time he spends with Yuki as his girl persona he is a genuinely caring and nice person, albeit somewhat pushy. And the women he goes out/sleeps with to get money so he can afford his other life as a girl are middle-aged women who sleep with a 19-year-old to prove to themselves they're still desirable. He is sly and manipulative, but actually pales in comparison to his crush Mikako.

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* Kaito from ''Himegoto - Juukyuusai No Seifuku'' comes off as this at first. He is a man who enjoys dressing up as the woman he has a crush on, a JerkAss who toys with women's emotions, pretended he was gonna rape Yuki, and generally acts manipulative and sly. However, the further the manga goes the more it becomes obvious that Kaito is more likely {{Transsexual}} {{Transgender}} than just a villainous crossdresser. His obsession with Mikako is creepy, however, a lot of things he does happen out of fear for not being accepted the way he is. The time he spends with Yuki as his girl persona he is a genuinely caring and nice person, albeit somewhat pushy. And the women he goes out/sleeps with to get money so he can afford his other life as a girl are middle-aged women who sleep with a 19-year-old to prove to themselves they're still desirable. He is sly and manipulative, but actually pales in comparison to his crush Mikako.



* [[spoiler:Marube]] from ''Manga/{{Yuureitou}}'' is obsessed with [[IJustWantToBeBeautiful becoming beautiful]] to the point where he would do anything to become a female [[spoiler:including attempting a brain transplant with his [[{{transsexual}} biologically female son]] Tetsuo.]] In his final appearance he's dressed as a woman, and a very attractive one despite [[OlderThanTheyLook being in his forties]], but is very unhinged.

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* [[spoiler:Marube]] from ''Manga/{{Yuureitou}}'' is obsessed with [[IJustWantToBeBeautiful becoming beautiful]] to the point where he would do anything to become a female [[spoiler:including attempting a brain transplant with his [[{{transsexual}} biologically female [[{{transgender}} son]] Tetsuo.]] In his final appearance he's dressed as a woman, and a very attractive one despite [[OlderThanTheyLook being in his forties]], but is very unhinged.



* ''Series/{{JAG}}'': In "Retrial", a sailor had unbeknownst to him hired a transsexual prostitute. When finding out, the sailor changed his mind and the prostitute threatens him with a knife.

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* ''Series/{{JAG}}'': In "Retrial", a sailor had unbeknownst to him hired a transsexual transgender prostitute. When finding out, the sailor changed his mind and the prostitute threatens him with a knife.



* In ''VideoGame/SaintsRow2'', ''VideoGame/SaintsRowTheThird'', and ''VideoGame/SaintsRowIV'' the player can dress their character in any clothes in the game, regardless of gender. So the player can make their character a transvestite, or even a {{Transsexual}} through EasySexChange, if they so desire. This can go into "Creepy" territory instead of "[[WholesomeCrossdresser Wholesome]]" by having a hugely muscled man running around in a tiny dress or worse/more hilarious a string bikini and beating random passerby's to death with [[WrestlerInAllOfUs wrestling moves]] and [[GroinAttack nut punches]] when he isn't blowing their brains out or running them over in a tank. In the third game, there's also a [[GiantMook Brute]], an 8-by-4 foot mountain of muscle, dressed like a naughty schoolgirl in the dungeons of a S&M sex club. There is no context for it being there outside of the club is run by [[BigBad the Syndicate]] and it's funny.

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* In ''VideoGame/SaintsRow2'', ''VideoGame/SaintsRowTheThird'', and ''VideoGame/SaintsRowIV'' the player can dress their character in any clothes in the game, regardless of gender. So the player can make their character a transvestite, or even a {{Transsexual}} {{Transgender}} through EasySexChange, if they so desire. This can go into "Creepy" territory instead of "[[WholesomeCrossdresser Wholesome]]" by having a hugely muscled man running around in a tiny dress or worse/more hilarious a string bikini and beating random passerby's to death with [[WrestlerInAllOfUs wrestling moves]] and [[GroinAttack nut punches]] when he isn't blowing their brains out or running them over in a tank. In the third game, there's also a [[GiantMook Brute]], an 8-by-4 foot mountain of muscle, dressed like a naughty schoolgirl in the dungeons of a S&M sex club. There is no context for it being there outside of the club is run by [[BigBad the Syndicate]] and it's funny.



* In ''WesternAnimation/TheSimpsons'', episode "There is Something About Marrying", pro golfer Veronica was going to marry Patty under the false pretense of being a lesbian woman. (It's somewhat unclear, but Veronica doesn't seem to be a genuine {{Transsexual}} so much as a creepy male golfer who only crossdresses so that he can compete on the womens' tour.)

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* In ''WesternAnimation/TheSimpsons'', episode "There is Something About Marrying", pro golfer Veronica was going to marry Patty under the false pretense of being a lesbian woman. (It's somewhat unclear, but Veronica doesn't seem to be a genuine {{Transsexual}} {{Transgender}} so much as a creepy male golfer who only crossdresses so that he can compete on the womens' tour.)
23rd Mar '18 1:31:03 PM Morgenthaler
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[[caption-width-right:350:[[JustForFun/{{Hello}} Hi...]]]]
10th Mar '18 12:35:12 PM RedScharlach
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*** Notable for the fact that, unlike Kamatari above, although she's competing for the affection of a man who will never look at her she's easily the most sane ''and'' the most physically powerful force he can mobilize, until he [[spoiler: goes [[OneWingedAngel Million Winged Angel]].]] (Meanwhile [[TheWoobie Legato's]] 'eat steak with no hands' and 'float around in sarcophagus of doom' lines have inspired mutinies out of sheer embarrassment from his subordinatees.

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*** Notable for the fact that, unlike Kamatari above, although she's competing for the affection of a man who will never look at her she's easily the most sane ''and'' the most physically powerful force he can mobilize, until he [[spoiler: goes [[OneWingedAngel Million Winged Angel]].]] (Meanwhile [[TheWoobie Legato's]] 'eat steak with no hands' and 'float around in sarcophagus of doom' lines have inspired mutinies out of sheer embarrassment from his subordinatees.subordinates.



** Charlotte Chuhlourne is a flamboyant MagicalGirl parody. His normal attire may involve trousers, but he wears a tight tank top with plunging, frilly neckline and bared midriff, and his trousers expose the tops of his thighs on each side as well as revealing a little too much of his [[FanDisservice pelvic area]]. His hair is very long and painstakingly curled and styled and he wears long, false eyelashes. In his resureccion, called ''Reina des Roses'', he transforms into a frilly, bikini-style tutu costume that is designed with the petals of a [[FlowerMotif rose]] in mind. He's extremely proud of his [[MachoCamp muscular strength]] and his costumes are designed to show off his body as much as possible.
** Giselle is accused of being a man by Yumichika but neither confirms nor denies the accusation. While she actually dresses in a quite wholesome-looking fashion, the more that's revealed about her, the less wholesome she appears. [[spoiler:Yumichika claims she reeks of semen, and a [[TheUndead resurrected]] Charlotte also identifies her as "[[DragQueen resembling]]" him after sniffing her. Giselle creates zombies by infecting shinigami with her blood and even kills her quincy friend Bambietta to turn her into a zombie. She drools when excited and the thought of using her blood on others seems to turn her on.]]

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** Charlotte Chuhlourne Chuhlhourne is a flamboyant MagicalGirl parody. His normal attire may involve trousers, but he wears a tight tank top with plunging, frilly neckline and bared midriff, and his trousers expose the tops of his thighs on each side as well as revealing a little too much of his [[FanDisservice pelvic area]]. His hair is very long and painstakingly curled and styled and he wears long, false eyelashes. In his resureccion, Resureccion form, called ''Reina des Roses'', de Rosas'', he transforms into a frilly, bikini-style tutu costume that is designed with the petals of a [[FlowerMotif rose]] in mind. He's extremely proud of his [[MachoCamp muscular strength]] and his costumes are designed to show off his body as much as possible.
** Giselle is accused of being a man by Yumichika but neither confirms nor denies the accusation. While she actually dresses in a quite wholesome-looking fashion, the more that's revealed about her, the less wholesome she appears. [[spoiler:Yumichika claims she reeks of semen, and a [[TheUndead resurrected]] Charlotte also identifies her as "[[DragQueen resembling]]" him after sniffing her. Giselle creates zombies by infecting shinigami with her blood and even kills her quincy Quincy friend Bambietta to turn her into a zombie. She drools when excited and the thought of using her blood on others seems to turn her on.]]



* Happens, accidently, to Sora in ''Manga/KingdomHeartsII'', when the fairies put him in a ball gown (complete with tiara) while designing a new outfit for him. It's clear from that scene that he hates cross-dressing.
* Kaito from ''Himegoto - Juukyuusai No Seifuku'' comes off as this at first. He is a man who enjoys dressing up as the woman he has a crush on, a JerkAss who toys with women's emotions, pretended he was gonna rape Yuki, and generally acts manipilative and sly. However, the further the manga goes the more it becomes obvious that Kaito is more likely {{Transsexual}} than just a villainous crossdresser. His obsession with Mikako is creepy, however, a lot of things he does happen out of fear for not being accepted the way he is. The time he spends with Yuki as his girl persona he is a genuinely caring and nice person, albeit somewhat pushy. And the women he goes out/sleeps with to get money so he can afford his other life as a girl are middle-aged women who sleep with a 19-year-old to prove to themselves they're still desirable. He is sly and manipulative, but actually pales in comparison to his crush Mikako.

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* Happens, accidently, accidentally, to Sora in ''Manga/KingdomHeartsII'', when the fairies put him in a ball gown (complete with tiara) while designing a new outfit for him. It's clear from that scene that he hates cross-dressing.
* Kaito from ''Himegoto - Juukyuusai No Seifuku'' comes off as this at first. He is a man who enjoys dressing up as the woman he has a crush on, a JerkAss who toys with women's emotions, pretended he was gonna rape Yuki, and generally acts manipilative manipulative and sly. However, the further the manga goes the more it becomes obvious that Kaito is more likely {{Transsexual}} than just a villainous crossdresser. His obsession with Mikako is creepy, however, a lot of things he does happen out of fear for not being accepted the way he is. The time he spends with Yuki as his girl persona he is a genuinely caring and nice person, albeit somewhat pushy. And the women he goes out/sleeps with to get money so he can afford his other life as a girl are middle-aged women who sleep with a 19-year-old to prove to themselves they're still desirable. He is sly and manipulative, but actually pales in comparison to his crush Mikako.



* Even Film/JamesBond's nemesis Blofeld undertook a spot of cross-dressing (although it was technically a desperate disguise) in the film adaption of ''Film/DiamondsAreForever''. Also, ''Film/{{Thunderball}}'' has an old enemy of Bond disguised as his own "widow".

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* Even Film/JamesBond's nemesis Blofeld undertook a spot of cross-dressing (although it was technically a desperate disguise) in the film adaption adaptation of ''Film/DiamondsAreForever''. Also, ''Film/{{Thunderball}}'' has an old enemy of Bond disguised as his own "widow".



* In the ''Film/{{Redwall}}'' series, Emperor Ublaz Mad Eyes is a possibly-not-intentional-on-the-author's-part borderline example. The silk robes, painted nails and perfume he is mentioned as having in his first appearance are par for the course for an evil exotic emperor, but the entire book revolves around him attempting to steal a famous set of six large pink pearls to put in his crown. He goes so far as to slaughter entire tribes to get the things. He also stops in the middle of his angry MirrorMonologue to debate what he's going to wear for the victory parade; ''"If I had the Tears of all Oceans now, they would be set in my crown, all six of them, wondrous rose-colored pearls! I would don my green silk mantle, or maybe the black one with gold trim ..."''

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* In the ''Film/{{Redwall}}'' series, Emperor Ublaz Mad Eyes is a possibly-not-intentional-on-the-author's-part borderline example. The silk robes, painted nails and perfume he is mentioned as having in his first appearance are par for the course for an evil exotic emperor, but the entire book revolves around him attempting to steal a famous set of six large pink pearls to put in his crown. He goes so far as to slaughter entire tribes to get the things. He also stops in the middle of his angry MirrorMonologue to debate what he's going to wear for the victory parade; ''"If I had the Tears of all Oceans now, they would be set in my crown, all six of them, wondrous rose-colored pearls! I would don my green silk mantle, or maybe the black one with gold trim ...trim..."''



* While TheMaster spends the majority of the ''Series/DoctorWho'' story ''The End of Time'' wearing a black hoodie, the climatic sequence where [[spoiler: The Master uses the immortality gate to transform nearly the entire global population into copies of himself, sees him don a variety of outfits. The sight of John Simm in a dress applauding himself while giggling insanely can also be counted as a CrowningMomentOfFunny.]]

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* While TheMaster spends the majority of the ''Series/DoctorWho'' story ''The End of Time'' wearing a black hoodie, the climatic sequence where [[spoiler: The [[spoiler:the Master uses the immortality gate to transform nearly the entire global population into copies of himself, sees him don a variety of outfits. The sight of John Simm in a dress applauding himself while giggling insanely can also be counted as a CrowningMomentOfFunny.]]



** In the season five episode "Demons and Angels", Lister is running for his life from the evil versions of the Red Dwarf crew, until he runs into Evil Rimmer ... wearing what is best described as a Dominatrix-type get up.
** In another Series 5 episode, "Quarantine". When Rimmer contracts a holo-virus that sends him mad, he appears out of uniform, and holding [[HandPuppet Mr]] [[EnsembleDarkhorse Flibbles]]. Also lampshaded:

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** In the season five episode "Demons and Angels", Lister is running for his life from the evil versions of the Red Dwarf crew, until he runs into Evil Rimmer ... Rimmer, wearing what is best described as a Dominatrix-type get up.
** In another Series 5 episode, "Quarantine". When "Quarantine", when Rimmer contracts a holo-virus that sends him mad, he appears out of uniform, and holding [[HandPuppet Mr]] [[EnsembleDarkhorse Flibbles]]. Also lampshaded:



* ''Series/WhiteRabbitProject'': The ''Wardrobe Malfunction'' legend has this as one of the attempted escape shenanigans in the "Jailbreak" episode. A convict disguises himself as his visiting wife, trading places with her, to escape. The title comes into play in that the convict was poorly disguised, couldn't act like a woman convincingly, and got recaptured within 15 minutes.

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* ''Series/WhiteRabbitProject'': The ''Wardrobe Malfunction'' legend has this as one of the attempted escape shenanigans in the "Jailbreak" episode. A convict disguises himself as his visiting wife, trading places with her, her to escape. The title comes into play in that the convict was poorly disguised, couldn't act like a woman convincingly, and got recaptured within 15 minutes.



* Gao from ''VideoGame/RhapsodyAMusicalAdventure''. In fact, due no doubt in large part to the graphical limitations of the game, it's actually near-impossible to tell it's a girl. She ends up giving a forced, out of place speech about how people can't tell she's a girl just before you fight her simply so the audience can know.

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* Gao from ''VideoGame/RhapsodyAMusicalAdventure''. In fact, due no doubt in large part to the graphical limitations of the game, it's actually near-impossible to tell it's a girl. She ends up giving a forced, out of place out-of-place speech about how people can't tell she's a girl just before you fight her simply so the audience can know.



* Justice from ''VideoGame/GuiltyGear'' counts, if only because of the huge crotch spike in her armor ...

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* Justice from ''VideoGame/GuiltyGear'' counts, if only because of the huge crotch spike in her armor ...armor...
6th Dec '17 9:54:30 AM DracoKanji
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* The Sailor Bubba meme features an obese hairy guy cosplaying as ''Franchise/SailorMoon'', and is a common stereotype of male to female cross-players (although there is [[AttractiveBentGender the other extreme]])

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* The Sailor Bubba meme features an obese hairy guy cosplaying as ''Franchise/SailorMoon'', and is a common stereotype of male to female cross-players (although there is [[AttractiveBentGender the other extreme]]) extreme]]). Once this one became too common and no longer "edgy", the [[Anime/CowboyBebop Man Faye]] meme took its place.
6th Dec '17 9:51:23 AM DracoKanji
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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.''

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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 ''dozens of snakes for legs.'''' His personality is otherwise fairly normal.
7th Nov '17 8:34:03 AM HarpieSiren
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* Mettaton from ''VideoGame/{{Undertale}}'' is a complicated mess. Originally he is a [[spoiler:ghost, which are supposed to be genderless]], yet his house is "girlishy" pink. When in his casual robot form, he's always referred to as "he", but he performs his VillainSong in a dress. When in his [[spoiler:EX form]], he's still referred to as "he", but has some feminine characteristics to his design: most notably, slim legs that he adores. His body design also contains pink colour in great amounts (though that doesn't really matter, as most of the time we see that form, it's in battle mode, which is mostly black-and-white anyway).
30th Sep '17 8:17:47 AM Fuyumoto
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* [[GenderFlip Tamamo no Mae]] from ''[[VideoGame/{{Onmyoji}} Onmyōji]]'' who often assumes the form of a woman (which is also his [[PowerMakeover Awakened]] appearance) to go around wrecking havoc. This and his [[Creator/RomiPark voice actress]] makes him the victim of a lot of ViewerGenderConfusion.
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