History Main / WholesomeCrossdresser

6th Feb '16 7:11:40 AM Tyk5919
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* Lee from ''Literature/OutOfPosition'', who mostly crossdressed to fool football players like Dev and just because he wanted to. He stops after ''Isolation Play''.
2nd Feb '16 8:21:41 PM sayaleviathan
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* ''Anime/CodeGeass'' Picture Dramas featured Rivalz, Suzaku and Lelouch crossdressing as girls. Suzaku doesn't seem to mind while Lelouch, who is prettier in a fancy dress, didn't like it and gets harassed by Suzaku and Rialz on Student Council President Milly Ashford's orders. The R2 picture drama has him dressed up as a ''belly dancer'' of all things so that he, Kallen and C.C. can infiltrate the Chinese Federation's territory. The PSP VisualNovel game, ''Lost Colors'', has the PlayerCharacter, Rai, having an ImagineSpot of Lelouch wearing a wedding dress and boy, he still looks pretty.
2nd Feb '16 3:14:28 AM migmit
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* In ''Film/HussarBallad'' a young girl, Shura, dresses as a man just for a masked ball at first, but later uses that disguise to enter the army and serves as a real hussar officer.
22nd Jan '16 10:59:59 PM greatpikminfan
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Updating to fit Afterbirth.
* It's hinted in ''VideoGame/TheBindingOfIsaac'' that all of the alternate characters in the game are possibly just Isaac wearing different wigs and accessories. This includes the two female characters, Eve and Magdeline.
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* It's hinted in ''VideoGame/TheBindingOfIsaac'' that all of the alternate characters in the game are possibly just Isaac wearing different wigs and accessories. This includes the two three female characters, Eve Eve, Magdalene, and Magdeline.Lilith.
8th Jan '16 1:32:26 PM Willbyr
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* ''Both'' of the leads of ''PenguinRevolution'' are {{Wholesome Crossdresser}}s. Ryo Katsuragi is obliged by his (rather quirky) talent agency to attend school as "Ryoko," and after she learns his secret and agrees to help him by acting as his personal agent, Yukari Fujimaru is obliged to dress as a man since the agency doesn't employ women as agents. HilarityEnsues.
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* ''Both'' of the leads of ''PenguinRevolution'' ''Manga/PenguinRevolution'' are {{Wholesome Crossdresser}}s. Ryo Katsuragi is obliged by his (rather quirky) talent agency to attend school as "Ryoko," and after she learns his secret and agrees to help him by acting as his personal agent, Yukari Fujimaru is obliged to dress as a man since the agency doesn't employ women as agents. HilarityEnsues.
6th Jan '16 3:12:09 AM JulianLapostat
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* It's not well known, but contrary to UsefulNotes/JesseJames' reputation as a BadAss cowboy outlaw, one of his early schemes involved crossdressing as prostitutes to waylay Union soldiers so he and his fellow proslavery confederate guerillas could shank them. As noted by Creator/SamuelFuller: --> '''Fulller''': He and his brother were two illiterate, uncouth rats. They were fifteen and seventeen years old when they joined Quantrill's Raiders, during the Civil War. Jesse James at fifteen was assigned a joy by Quantrill: he would masquerade as a girl, pick up soldiers and bring them into a house called the House of Joy, a house of prostitution. He would get drunk with the soldiers - [[PrettyBoy he had a very pretty face]] - and when they all got drunk, he and Quantrill would kill the soldiers and rob them."
4th Jan '16 8:12:12 PM DrOO7
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* The heroine of the bodice-ripper ''Whisper To Me Of Love'' is revealed to be this when her disguise comes off while she's grappling with a would-be victim (she's a pickpocket). She admits to disguising herself as a boy to escape the advances of degenerates (but given the CrapsackWorld that the slums of London area depicted as, this probably wouldn't keep her much safer).
3rd Jan '16 8:33:46 PM Willbyr
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* Used as a one-off gag in ''GameXRush'', where the middle-class Memori is portrayed as a "Cinderella" as oposed to Yuuki's imagined wealth. Also, Memori dresses as a nurse to "avoid suspicion" and stay in the hospital after hours... to make sure Yuuki doesn't escae, of course.
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* Used as a one-off gag in ''GameXRush'', ''Manga/GameXRush'', where the middle-class Memori is portrayed as a "Cinderella" as oposed to Yuuki's imagined wealth. Also, Memori dresses as a nurse to "avoid suspicion" and stay in the hospital after hours... to make sure Yuuki doesn't escae, of course.
13th Dec '15 2:53:26 PM Pichu-kun
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* Alice in ''LightNovel/MariaSamaGaMiteru''.

* There's quite a few of these in ''Manga/FamilyCompo'' -- the main character's adoptive family (his aunt and uncle) turn out to be gender-swapped -- that is, the extremely masculine uncle is biologically a woman, the extremely feminine aunt is biologically male. Their daughter switched genders every few months as she was growing up, until deciding to stay female when she entered college -- but the main character's not sure what she is biologically, which leads to most of the [[WillTheyOrWontThey tension between them]]. The main character's also effeminate to the point that he ends up as the female lead in a student film, with a lesbian chasing him around, with a yakuza boss trying to convince him to get the "big snip"!

* Ash from ''Anime/{{Pokemon}}'' has to dress as "Ashley" to get his Gym battle with Erika. [[LoveableSexManiac Brock]] is fooled, but Pikachu isn't (scent, maybe?). Ash would go on to invoke this trope a couple more times, once as a {{Meido}}. ** Many of James's disguises involve wearing dresses, even when there's absolutely no reason to (once he and Jessie posed as a bride and groom- him as the bride and her as the groom).
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* ''Anime/{{Pokemon}}'': ** Ash from ''Anime/{{Pokemon}}'' has to dress as "Ashley" to get his Gym battle with Erika. [[LoveableSexManiac Brock]] is fooled, but Pikachu isn't (scent, maybe?). Ash would go on to invoke this trope once a couple more times, saga (minus Johto), once as a {{Meido}}. ** Many of James's disguises involve wearing dresses, even when there's absolutely no reason to (once he and Jessie posed as a bride and groom- him as the bride and her as the groom). Jessie also used to crossdressva lot as well.

* Kotobuki Seishiro ([[InsistentTerminology Seiko]]!) from LovelyComplex is very nice and friendly (a little [[UnsettlingGenderReveal TOO friendly]] with Ootani) who insists "god made a mistake" and put her into a boy's body. After TheReveal and fending off a few hateful comments, Ootani, Risa, and friends take him/her in as part of their group. Aside from some friendly teasing (often [[HoYay by way]] [[{{Tsundere}} of]] [[LongHairedPrettyboy Haruka]]), Seiko seems to fit in and find a happy school life with little difficulty.

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* Kotobuki Seishiro ([[InsistentTerminology Seiko]]!) from LovelyComplex is very nice An episode of ''Anime/MichikoToHatchin'' had Hatchin meeting a man whose job involves him being a crossdressing actor. While he wears men's clothes outside of work, his son dresses as a girl 24/7 and friendly (a little [[UnsettlingGenderReveal TOO friendly]] with Ootani) who insists "god made a mistake" and put her into a boy's body. After TheReveal and fending off a few hateful comments, Ootani, Risa, and friends take him/her in as part of their group. Aside from some friendly teasing (often [[HoYay by way]] [[{{Tsundere}} of]] [[LongHairedPrettyboy Haruka]]), Seiko seems wants to fit in and find be a happy school life with little difficulty.female impersonator like his father when he grows up.
11th Dec '15 6:36:22 PM nombretomado
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** [[YouCanPlayThis JewWario]] has actually crossdressed in public on several occasions (most notably at showings of RockyHorrorPictureShow).
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** [[YouCanPlayThis JewWario]] Creator/JewWario has actually crossdressed in public on several occasions (most notably at showings of RockyHorrorPictureShow).
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