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Wholesome Crossdresser

 Wholesome Crossdresser
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 Wholesome Crossdresser
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Wholesome Crossdresser
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Advertisement:propertag.cmd.push(function() { proper_display('tvtropes_mobile_ad_1'); })Crossdressing characters who are presented in a positive (or at least neutral) way. Frequently presented as attractive (or at least not unattractive), relatively "normal" people as opposed to perverts or sexual deviants.
The Wholesome Crossdresser may be of any sexual orientation, but in settings where being straight is considered part of being "normal," one can expect to see the character's heterosexuality explicitly highlighted.
Some permutations of the trope are more or less unique to Japanese works. The Japanese Wholesome Crossdresser is usually well-groomed, compassionate, nice, and above all, so convincing that their sex is only mentioned on occasion, as a reminder to newer members of the audience. There's a fair chance someone will get a crush on them, although this is usually resolved after The Reveal.
Advertisement:propertag.cmd.push(function() { proper_display('tvtropes_mobile_ad_2'); })The opposite of Creepy Crossdresser. May overlap with Disguised in Drag or its Distaff Counterpart, Sweet Polly Oliver. (If the character wears cross-dressing disguises more often than seems strictly necessary, this trope may apply.) Wholesome Crossdressers tend to enjoy dressing, even if only reluctantly, secretly, or subconsciously.
Often overlaps with Drag Queen (a campy, hyper-feminine form of expression with heavy ties to gay/bi male culture), but usually doesn’t with being Transgender (an intricate subject that is more connected with inward identity than outward appearance).
Compare Otokonoko Genre, which is about male crossdressers (and occasionally Transgender women), that are almost always presented as wholesome.
 Wholesome Crossdresser
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2020-11-06T06:13:17Z
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IriaZeiramTheAnimation
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Trainspotting
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Overlord
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BattleTendency
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JoJolion
 Wholesome Crossdresser
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StoneOcean
 Wholesome Crossdresser
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Utawarerumono
 Wholesome Crossdresser
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DBTropes
 Wholesome Crossdresser / int_122bfae1
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Wholesome Crossdresser
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Midori Days:
Seiji is forced to crossdress in an attempt to catch a molester on a train. Naturally, some acquaintances from school see him, and decide that he's hot.
Kouta is often forced to wear various female outfits by a female gang in the manga.
 Wholesome Crossdresser / int_122bfae1
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 Midori Days (Manga)
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Wholesome Crossdresser / int_122bfae1
 Wholesome Crossdresser / int_1248906e
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Wholesome Crossdresser
 Wholesome Crossdresser / int_1248906e
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Ayumi, in Shion no Ou, cross-dresses throughout most of the anime, in order to enter tournaments.
 Wholesome Crossdresser / int_1248906e
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1.0
 Wholesome Crossdresser / int_1248906e
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 Shion no Ou (Manga)
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Wholesome Crossdresser / int_1248906e
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Wholesome Crossdresser
 Wholesome Crossdresser / int_1341d59a
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Yoshinori of Yubisaki Milk Tea is a high school boy who got drafted into wearing a wedding dress for a photo shoot and found that he liked cross-dressing, creating a female persona named Yuki. He ends up attracting admirers in both his male and female guises, but remains (mostly) straight, and he anguishes over the thought of giving up Yuki in order to mature.
 Wholesome Crossdresser / int_1341d59a
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 Yubisaki Milk Tea (Manga)
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Wholesome Crossdresser / int_1341d59a
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Wholesome Crossdresser
 Wholesome Crossdresser / int_1402b91c
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As of Hetalia Bloodbath 2010, we've also had Hong Kong in a maid dress, and China in a qipao.
 Wholesome Crossdresser / int_1402b91c
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1.0
 Wholesome Crossdresser / int_1402b91c
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 Hetalia Bloodbath 2010 (Manga)
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Wholesome Crossdresser / int_1402b91c
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Wholesome Crossdresser
 Wholesome Crossdresser / int_18c0192b
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In Realm of the Elderlings The Fool, while his gender is never explicitly stated, switches from a female persona, Lady Amber, to a male persona, The Fool depending on the situation he is in and people he is with.
 Wholesome Crossdresser / int_18c0192b
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Wholesome Crossdresser / int_18c0192b
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Wholesome Crossdresser
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One of the Ferris Wheel date options for the male player character in Pokémon Black 2 and White 2 is a schoolteacher who, in the Japanese version only, takes off his shirt in the heat, and admits that he had to pass as a woman to get the job.
 Wholesome Crossdresser / int_196b618d
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 Wholesome Crossdresser / int_196b618d
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 Pokémon Black 2 and White 2 (Video Game)
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Wholesome Crossdresser / int_196b618d
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Wholesome Crossdresser
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In the Bloody Jack series, the eponymous Jacky Faber's adventure begins when she disguises herself as a boy in order to open up more opportunities to escape her dangerous life as a homeless orphan on the mean streets of nineteenth-century London. Her plan works. From then on throughout the series, she dons male garb whenever necessity or whimsy calls for it.
 Wholesome Crossdresser / int_1a80880b
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Wholesome Crossdresser
 Wholesome Crossdresser / int_1ad81662
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Gasper in High School Dx D wears the school's female uniform and pulls it off so well everyone needs to be told he's a he on first meeting. It doesn't help that he acts shy and feminine, to the point of quickly developing a crush on Issei. Issei tries to get him to start wearing more masculine clothing, at first because it creeps him out, and later because Gaspar's cross-dressing turns out to be rooted in trauma from his Dark and Troubled Past and he wants his friend to move past that.note The crossdressing itself is treated as a harmless symptom by itself
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Wholesome Crossdresser
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Any playable male character from The World Ends with You can become one if their Bravery stat is high enough. Bravery is used to determine what clothes characters can wear, with female clothing having a prohibitively high Bravery score that initially only Shiki can match, but any male character can grind their Bravery stat high enough to wear them as well. Subverted, in that the clothes don't appear on the characters' in-game sprites or portraits.
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 The World Ends with You (Video Game)
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Wholesome Crossdresser / int_1adee40d
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Wholesome Crossdresser
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Angel Dumott Schunard from RENT, who may also be Transgender. It's kinda hard with Trans Equal Gay thing that's there.
 Wholesome Crossdresser / int_1afaadc2
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 RENT (Theatre)
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Wholesome Crossdresser / int_1afaadc2
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Wholesome Crossdresser
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In Tokyo Ghoul :Re, several characters crossdress as part of an investigation into a human trafficking ring targeting young women. Sasaki not only looks stunning in disguise, but is shown really enjoying getting into the role of "Sasako". When a superior later criticizes his "unconventional" methods, it further establishes him as a Jerkass and completely unreasonable. During the same investigation, Suzuya epically puts a stop to a slave auction while wearing a long wig and Lolita dress.
 Wholesome Crossdresser / int_1b021fcb
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Wholesome Crossdresser / int_1b021fcb
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Wholesome Crossdresser
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Ranma ½:
Tsubasa Kurenai, who's in love with Ukyō Kuonji, a Bifauxnen female crossdresser. A later character, Konatsu, also falls into Ukyō's orbit. It should be noted that Konatsu appears as a traditional Japanese kunoichi or female ninja. Of course, Konatsu was reared to think of himself as a girl (even covering his bare chest and squealing) with very few concessions to his masculinity. Tsubasa, on the other hand, is a Master of Disguise who can be anything from a mailbox to a tree... but he prefers to wear a schoolgirl uniform underneath, rationalizing that if Ukyō chooses to dress like a man, then he should dress like a girl to match. Note that both characters were wholly mistaken for female until the very last page of their introduction stories, although they never actually claimed to be girls. Although, in Tsubasa's case, his appearance was so convincing that, unaware that Ukyō had met him while going to a boys only school to further her own "masquerade", they initially believed him to be a girl who had mistaken Bifauxnen Ukyō for a real boy. Then they thought that "she" was a lesbian after they learned he had known Ukyō was really a girl all along (which greatly startled Ukyō herself, who had evidently figured that Tsubasa was a cross-dressing homosexual guy who had been fooled by her disguise).
Later in the manga, Ranma, Ryōga, and a couple other characters must distract the Yamata No Orochi, which has a taste for women. Therefore, they (as men, even Ranma) dress up as female stereotypes: a schoolgirl, a nurse, a meter maid, and a bride. Akane, meanwhile, crossdresses as a man to avoid being eaten.
Also a special note is to be made of Ranma him/herself. Although the Chinese uniform he tends to wear is generally thought of as genderless, he will often end up being turned back to male while wearing feminine attire (much to his chagrin and ridicule). On the other hand, standalone character illustrations, cover art, and chapter breaks tend to depict female Ranma as unusually feminine. However it depends whether or not it consider cross-dressing since through magic, Ranma can be completely biologically female or male at anytime. Either way he does seem to spend a lot more time being a woman than strictly necessary, and several gags are made out of him willingly dressing up in some very effeminate clothes and seemingly enjoying it.
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Wholesome Crossdresser
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Kazuki in Get Backers. The writers, especially in the anime, will take any excuse they can to get him into women's clothing. Sometimes it's a misunderstanding, sometimes it's part of his job, sometimes it's favor for a friend... and then there's the official art of him in women's swimsuits. The anime went so far as to lampshade it in the fourth ending: there are two points where the characters are divided by gender, and he's with the girls both times. To be fair, he's mistaken for a woman when he's not explicitly crossdressing.
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Wholesome Crossdresser
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Raffles: in "The Rest Cure", Pretty Boy Bunny makes a fairly convincing woman when in drag.
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Wholesome Crossdresser
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From Suikoden V, Rahal dresses up as his sister to distract some guards. Those guards were not the only ones distracted; he looks exactly like his sister when wearing her dress and hairstyle.
 Wholesome Crossdresser / int_1c25dba1
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Wholesome Crossdresser
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In Toot & Puddle: Charming Opal, Puddle dresses up as the tooth fairy, hoping he can sneak into Opal's room and leave a quarter for her in exchange for her tooth. He ends up being too late because he and Toot fall asleep and by the time they wake up, it's morning. Turns out it doesn't matter, though; the tooth fairy came anyway.
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Hideri Kanzaki of Blend-S is a boy who dresses like a girl. He works as a waitress at a cafe and desires to be the cutest. Unlike most examples, he's more similar to a Real Life transvestite — he does that because he likes it, yet he continues to see himself as male and appears to be heterosexual.
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Wholesome Crossdresser
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Kiri in the manga Never Give Up inherited her father's facial features and build and has a tendency to act "princely" on occasion, but has a distinctly female personality and wears the girl uniform. Doesn't stop half the school's female population from developing huge crushes on her. However, in order to stay close to her love interest, the effeminate Tohya, she has to sign a modeling contract. As a male model.
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Wholesome Crossdresser
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Lee from Out of Position, who mostly crossdressed to fool football players like Dev and just because he wanted to. He stops after Isolation Play.
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Wholesome Crossdresser
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Mizuho in Otome wa Boku ni Koishiteru. He's so frightfully good at it, he makes all the girls gay for him. Or something. Hell even in one of the later episodes where one of the other characters is looking through her old picture album, we see him (as a little kid) in a girl's swimsuit.
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 Otome wa Boku ni Koishiteru (Visual Novel)
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Wholesome Crossdresser
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Jerry from Tom and Jerry also cross-dressed a few times to trick Tom, who apparently is less likely to be violent towards a girl mouse.
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Examples from Channel Awesome:
Spoony as Spoonette and The Gate Cleaner's Wife, Linkara as 80s Chick, Benzaie as Veronique and The Nostalgia Critic as an Airline Hostess.
Critic does this fairly often and has done since he was at least thirteen, expressing much embarrassment at the home videos of a teenage him in full drag. He was also Raised as the Opposite Gender for a bit, giving him a few issues. A nice moment in The Monster Squad review has Tamara wanting her cross-dressing as a boy acknowledged, and he dismisses it because he's cross-dressed for fun so much that it's not a big deal.
JewWario has actually cross-dressed in public on several occasions (most notably at showings of The Rocky Horror Picture Show).
Benzaie has made cross-dressing a running joke on his show for sketches about his more girly interests.
Tacoma from Demo Reel played Oprah for a parody and dressed as Belle from Beauty and the Beast to make Rebecca happy. He didn't mind either costume.
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The main cast of Otoko no Ko wa Meido Fuku ga Osuki!? are four brothers who help their parents' Maid Cafe, and dress accordingly. The middle brothers usually crossdress only for work or other cafe-related business, while the oldest and youngest brothers crossdress all the time. In fact, the oldest brother, Nao, is so feminine that the girls at school pretty much treat him as one of their own and let him use female toilet and changing room without problem.
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 Otoko no Ko wa Meido Fuku ga Osuki!?
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Slayers does this once a season, one episode per season (except seasons 4-5). Fans of the series refer to this as Episode 17, as each crossdressing episode is the seventeenth episode in the given season (and this came from the first season's alphabet-based Idiosyncratic Episode Naming—the seventeenth letter is Q, creating a "queer" implication). Ironically, not just the male cast, but often support characters introduced in the episode itself as well. Perhaps the most bizarre example is the "drag-on" sea dragon in the first season, who Gourry defeats by scratching its face and forcing the dandy dragon to retreat lest it gain any defacing scars.
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 Slayers
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Huo Long from Haou Airen. His heart is in the right place, but he is a Triad member.
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 Haou Airen (Manga)
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Death Smiles II features Lei, who is a twelve-year-old boy wearing an Elegant Gothic Lolita maid outfit. Apparently, this is because this was the only outfit available to him when he arrived (and considering he was suffering from hypothermia, he didn't really have the luxury of being picky).
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The Legend of Zelda: Breath of the Wild has Link crossdress in order to enter Gerudo City to petition their chief for aid against Divine Beast Vah Naboris since voe (men) are forbidden from entering the city. Thankfully, the vai (women) who catch on to Link's true gender are either functional outcasts or Riju, all of whom have their own reasons for letting him stay despite this knowledge.
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 The Legend of Zelda: Breath of the Wild (Video Game)
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Louis from The Extra Man until he decides it's not for him.
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And then there's the Goddamn Maidman! A burly, hulking, Batman style Badass Normal hero who also dresses up as a French maid. Complete with panties and fishnet stockings. Although there is a bit of humor wrung out of it (for example, the Hypocritical Humor of Maidman considering his own costuming choice normal and being an Animal-Themed Superbeing embarrassing, or when Maidman admits that part of the reason why he's The Dreaded is due to his providing in-universe Fan Disservice), for the most part, he's presented as a competent crimefighter and a genuine Nice Guy. There's also no hints of him being gay, trans, a Drag Queen or "perverted"; he just thinks a French maid outfit makes a neat costume for crime fighting.
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One of the many subplots in one of the first-season episodes of Touch involved Norah and Shada, a pair of teenaged girls in Saudi Arabia who pose as boys just so that they can do things that women are forbidden to do, like drive.
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Sayo Yasuda, also known as Shannon, Kanon, and Beatrice from Umineko: When They Cry is implied to be this in one direction or another. Of course, because Yasu's gender is never made explicit, no one's actually sure whether they're a girl cross-dressing as a guy or a guy cross-dressing as a girl. In the manga, however, it's implied that Sayo was a biologically male child who was Raised as the Opposite Gender.
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 Umineko: When They Cry (Visual Novel)
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Several minor examples from The Simpsons:
Bart once demonstrated how to walk in high heels to help Lisa prepare for a beauty pageant. He was surprisingly good at it.
Homer and Flanders both lost a bet over a children's miniature golf tournament, forcing each to mow the other's lawn while wearing their wives' best Sunday dress. (Flanders, in what is probably a moment of Early Installment Weirdness, comments cheerfully that it reminds him of his college fraternity days.)
In "Homer Loves Flanders", Homer fantasizes about looking at himself in a mirror wearing a wig shaped like Marge's hair.
In "The Springfield Connection", Homer mentions that he occasionally wears women's underwear; something that he and Marge apparently agreed was "strictly a comfort thing''.
Once, puppies tore up all of Bart's socks, forcing him to wear a frilly pink pair of Lisa's. He also wears pink culottes because "Hey, I gotta accessorize."
In "Whacking Day," Abe reveals that, while he didn't actually ride out World War II posing as a German cabaret singer, he did wear a dress for a while in the forties. ("Oh, they had designers then!")
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Maid-Sama!:
Aoi Hyoudou.
Yukimura as well, although in his case it's a matter of periodically being forced to crossdress (very convincingly) by the other characters rather than doing it of his own initiative. You can have three guesses as to what kind of aura other characters feel from him (despite his best efforts) and the first two don't count.
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Mr. Humphries of Are You Being Served?. In one episode, he helped out by cross-dressing by pretending to be a female customer to help Mrs. Slocombe get her job back.
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Once in MythBusters, Tory wore a bra For Science!. Another time, while re-enacting a scene from Speed, he wore a wig. "Once again, making my parents proud."
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 MythBusters
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One of the "edgy" things about Baz Luhrmann's modern remake of William Shakespeare's Romeo + Juliet is having Mercutio (played by Harold Perrineau) show up to the Capulets' ball — imagined in the remake as a Halloween party — dressed in drag. He stays in drag for a lot longer than is really necessary. Then again, it's Mercutio. He also dances and lip-syncs to "Young Hearts Run Free". It's awesome.
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 William Shakespeare's Romeo + Juliet
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In Oh! Edo Rocket the reason for Genzo's cross-dressing is never explained, but it might be an attempt to get people to notice him. Though his hair and makeup are very feminine from the beginning, he doesn't actually dress in women's clothes until near the end of the series after his mother has sold all his clothes and the only thing left for him to wear is a dress. The reactions to this are overwhelmingly positive, and he then goes on to play the female lead, Princess Moonbeam, in a play that sums up the events of the series.
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In an episode of Dai Sentai Goggle Five that featured dolls coming to life, Miki/Goggle Pink disguises herself first as a male clown with a painted mask and just a slight change in voice, and later successfully pulls off a handsome prince disguise via a wig and a fitting outfit.
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Wholesome Crossdresser
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Looney Tunes: Bugs Bunny, when he's trying to trick someone. Most notably done in What's Opera, Doc?.
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 Looney Tunes
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Makoto in Nicoichi crossdresses to act the mother role for his son, who due to his young age could not understand the fact that his mother has already passed on.
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Wholesome Crossdresser
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Makoto Mizuhara from El-Hazard: The Magnificent World, Yakumo from 3×3 Eyes and Yellow Belmont aka Lancer from Genesis Climber MOSPEADA/Robotech Third Generation crossdress as a plot necessity rather than for their personal tastes. I.e.: Lancer crossdresses and poses as a female Idol Singer to act as a spy for the resistance group he's a part of, Makoto was Disguised in Drag posing as the missing Princess Fatora, and Yakumo crossdressed for his night job.
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 El-Hazard: The Magnificent World
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Tales Series:
In Tales of Vesperia, Karol can end up wearing a pink dress and a red hair ribbon for the sake of distracting a guard if you choose to. You can obtain this same costume for him to use all the time later on. Rita can also get in on this, as she has the costumes of Mao and Walter available for her to wear.
Milla from Tales of Xillia can wear the costumes of Stahn and Dhaos. She also has access to Asbel's costume in Tales of Xillia 2
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Twitch streamer F1NN5TER, initially known for his Minecraft gameplay videos, gained popularity when he played some Omegle pranks where he dressed up as an e-girl named Rose. People noticed how attractive he looked as a girl, and this led to him frequently appearing as a girl during his streams, setting up subscriber milestones for himself to further explore his feminine side (such as spending nearly two weeks living as a girl). He even made an Instagram account for his Rose persona.
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 Twitch (Website)
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One of the male regulars at Callahan's Crosstime Saloon is a professional Marilyn Monroe impersonator, and a very convincing one at that, to the point that he's often hit on while at work. He's also a happily heterosexual married man with a wife and kids.
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Naruto:
Haku is on the borderline between Wholesome Crossdresser and Creepy Crossdresser being that he's an Anti-Villain.
From the fillers, there's Princess Toki of the Land of Birds, who is also impersonating her dead brother Sagi.
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 Naruto (Manga)
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While Nanami's gender in Sukisho is never explicitly discussed, his clothing is mostly ambiguous regarding gender, and the non gender specific pronouns of Japanese are of no help either, everyone treats him like he always acts. His winter coat, pink bunny slippers, and the outfit he wears in the kitchen at home, places him firmly into crossdresser land.
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Unusually for a children's show (especially a Disney one), The Weekenders twice implies that Carver is a crossdresser when his friends catch him in possession of girls' clothing.
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The Dukes of Hazzard: The Season 6 episode "Targets: Lulu and Daisy" — where a diamond thief and his henchmen learn that Daisy and Lulu have accidentally gotten hold of a suitcase containing a stolen necklace — has, at Bo and Luke's behest, Rosco and Boss Hogg dress as Daisy and Lulu, respectively, hoping to lure the thieves into a trap. Plenty of bad jokes abound until the thieves kidnap (and plan to kill) the sheriff and the county administrator.
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In Fullmetal Alchemist, there's an automail engineer named Mr. Garfiel. Though initially he doesn't wear female clothes, only makeup, he puts on some lacy, poofy shirts later on. He also acts overly feminine, even compared with the manga's normal female cast. He also frequently flirts with Ed and other male characters.
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Welcome to Marwen: Mark, who likes women's shoes (particularly high heels) and collects them. Nicol mentions her brother also likes women's shoes and clothing too. They aren't depicted badly as a result.
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Bridget from Guilty Gear.
The original story was that Bridget is part of a set of identical twins, which in his village were considered bad luck, and was sent to be a nun (either that, or he'd be abandoned to his death as a newborn), therefore his whole story path is him going Determinator and wanting to prove he wasn't a bad omen on anybody. His creator admits that making him a boy was, in the spirit of other characters in the game, to simply make him more interesting.
A common Image Macro used for Trolling shows a picture of him and says "Everyone's gay for Bridget". Very confusing if you haven't played the game. There's a reason Unsettling Gender Reveal used to be called "Dropped A Bridget On Him".
Despite his mannerisms and the promo art featuring him in feminine poses, Bridget does not actually identify as female. As far as he's concerned, he's just a boy in a habit who carries around a teddy bear and a yo-yo and really wishes people would stop thinking he's a girl.
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Rin Mitani of Hensuki: Are You Willing to Fall in Love with a Pervert, as Long as She's a Cutie? dresses as a boy during the school day, but once it's done he wears the girls' uniform before heading to the student council. The rest of the student council is fine with it since it lets him perform his duties more efficiently and they became used to it anyway.
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Seki from Doki Doki School Hours likes to dress up in women's attire - actually hoping he will impress girls that way.
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From +C: Sword and Cornett, there's multiple instances of this; both Belca and Eco have had to cross-dress to escape the public eye, and while for the most part it's a disguise, it appears that yes, they're very much this trope. In his youth, Eco apparently went out to drag contests, and when he's hiding from guards after escaping the castle, Musca finds him and asks him to fix her hair, because she thought he was a "pretty lady". Belca, dressed a girl (though he's wholely unwilling), accidentally has someone fall in love with him, and Musca's likewise called him a pretty lady. Eco says himself that Belca makes for a pretty girl — not a pretty as himself, of course.
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 Plus-Si (Manga)
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The briefly-appearing "Lillie Longtree" in Welkin Weasels: Vampire Voles is an actor who usually plays female roles, and wears a red riding hood when out walking in the forest "to confuse the beasties". It should probably be noted that Maudlin asks about this "with a touch of envy in his voice".
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Wholesome Crossdresser
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On Franklin and Friends, Franklin has no problem dressing up as his favorite superhero, Dynaroo, despite Dynaroo being a female superhero.
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 Franklin
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Wholesome Crossdresser
 Wholesome Crossdresser / int_3a7ec3be
comment
Ayumu Mikoshiba from Otasuke Miko Miko-chan is one, however reluctantly. A character introduced later, though, has no such qualms about cross-dressing.
 Wholesome Crossdresser / int_3a7ec3be
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1.0
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 Otasuke Miko Miko-chan (Manga)
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Wholesome Crossdresser / int_3a7ec3be
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Wholesome Crossdresser
 Wholesome Crossdresser / int_3ac7b3cc
comment
Theatrica with the character Vivian.
 Wholesome Crossdresser / int_3ac7b3cc
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1.0
 Wholesome Crossdresser / int_3ac7b3cc
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1.0
 Theatrica
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Wholesome Crossdresser / int_3ac7b3cc
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type
Wholesome Crossdresser
 Wholesome Crossdresser / int_3b5a21ac
comment
The Amazing Chan and the Chan Clan character Stanley Chan has crossdressed on more than one occasion, twice for disguises and one for the sake of being hilarious. He pulls it off quite well, too.
 Wholesome Crossdresser / int_3b5a21ac
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1.0
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1.0
 The Amazing Chan and the Chan Clan
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Wholesome Crossdresser / int_3b5a21ac
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Wholesome Crossdresser
 Wholesome Crossdresser / int_3c912cc2
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In Tales of Vesperia, Karol can end up wearing a pink dress and a red hair ribbon for the sake of distracting a guard if you choose to. You can obtain this same costume for him to use all the time later on. Rita can also get in on this, as she has the costumes of Mao and Walter available for her to wear.
 Wholesome Crossdresser / int_3c912cc2
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1.0
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 Tales of Vesperia (Video Game)
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Wholesome Crossdresser / int_3c912cc2
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Wholesome Crossdresser
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In a possible homage to Laura Rolla, Gundam 00's Tieria Erde dons a dress, long hair extensions, and a large set of fake breasts at one point in the second season. Why? So that he can sneak into a high class party and speak to Ribbons. And to make fangirls melt into a collective puddle over Stupid Sexy Girl!Tieria, while several fanboys went "TIERIA IS A MAN AND HE'S OURS!".
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1.0
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1.0
 Mobile Suit Gundam 00
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Wholesome Crossdresser / int_3d22c14b
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type
Wholesome Crossdresser
 Wholesome Crossdresser / int_3f2b34bc
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Minoru in AKB49 – Renai Kinshi Jourei crossdresses to join an all-girl idol group to watch over his crush who is in the same group and protect her dream, without her knowledge.
 Wholesome Crossdresser / int_3f2b34bc
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1.0
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1.0
 AKB49 – Renai Kinshi Jourei (Manga)
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Wholesome Crossdresser / int_3f2b34bc
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Wholesome Crossdresser
 Wholesome Crossdresser / int_40010ddc
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Itsuki of HeartCatch Pretty Cure! spends half of the series dressed up as a guy and is usually seen in her male school uniform, mostly because she's determined to take over her grandfather's dojo while her older brother is sick. However, once her brother is cured and she takes up the role of the third Precure, she starts sliding back into more feminine roles, becoming a member of Erika and Tsubomi's fashion club and is seen in the Distant Finale wearing the school's female school uniform.
 Wholesome Crossdresser / int_40010ddc
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1.0
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1.0
 HeartCatch Pretty Cure!
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Wholesome Crossdresser / int_40010ddc
 Wholesome Crossdresser / int_414a9d3e
type
Wholesome Crossdresser
 Wholesome Crossdresser / int_414a9d3e
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Hibiki-sensei in I My Me! Strawberry Eggs, who cross-dresses in order to get a job from a man-hating boss. His Mentor is also a transvestite whose failed marriage to the boss caused her man-hating.
 Wholesome Crossdresser / int_414a9d3e
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1.0
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1.0
 I My Me! Strawberry Eggs
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Wholesome Crossdresser / int_414a9d3e
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Wholesome Crossdresser
 Wholesome Crossdresser / int_42151f05
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Leisure Suit Larry:
In Leisure Suit Larry III, the main character is able to dress up in a silly show-girl outfit and thus turn on a female lawyer who likes to wear masculine underwear ("I had no idea you liked cross-dressing too!") like singlets and boxer shorts.
Also, in ''Leisure Suit Larry Goes Looking for Love (in Several Wrong Places)', you need to go to great lengths to dress up as a convincing girl (getting waxed, having your hair chemically altered to become long, blonde and curly, wearing a bikini swimsuit and padding out the breasts) to bypass some KGB operatives.
 Wholesome Crossdresser / int_42151f05
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1.0
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1.0
 Leisure Suit Larry (Video Game)
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Wholesome Crossdresser / int_42151f05
 Wholesome Crossdresser / int_42c05590
type
Wholesome Crossdresser
 Wholesome Crossdresser / int_42c05590
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In Rocko's Modern Life Heffer's stepbrother Peter seemed to like to wear cheerleading outfits and ballerina tutus.
Tutus are considered unisex nowadays, though men usually wear them for comedic purposes.
 Wholesome Crossdresser / int_42c05590
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1.0
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1.0
 Rocko's Modern Life
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Wholesome Crossdresser / int_42c05590
 Wholesome Crossdresser / int_42d070ed
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Wholesome Crossdresser
 Wholesome Crossdresser / int_42d070ed
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In The World God Only Knows Yui Goudou started doing this after she returned to her body. She even admits guys' clothes are better.
And she gave Keima female uniform, while saying that it is something he needs for their future. Keep in mind that she is trying to conquer him. And later, he actually wears it!
 Wholesome Crossdresser / int_42d070ed
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1.0
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1.0
 The World God Only Knows (Manga)
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Wholesome Crossdresser / int_42d070ed
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Wholesome Crossdresser
 Wholesome Crossdresser / int_4310cdca
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A running joke in Here is Greenwood is Shun being mistaken for a girl. His younger brother is likewise androgynous enough to be distracting.
 Wholesome Crossdresser / int_4310cdca
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1.0
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1.0
 Here Is Greenwood (Manga)
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Wholesome Crossdresser / int_4310cdca
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Wholesome Crossdresser
 Wholesome Crossdresser / int_43a9c333
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A number of transvestites appeared in "Jupiter Jazz", an episode of Cowboy Bebop. One of them even returned for The Movie.
 Wholesome Crossdresser / int_43a9c333
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1.0
 Wholesome Crossdresser / int_43a9c333
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1.0
 Cowboy Bebop
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Wholesome Crossdresser / int_43a9c333
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Wholesome Crossdresser
 Wholesome Crossdresser / int_43de9426
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Colette: Missy, who habitually dresses as a man, is portrayed positively (many people then feel differently about this however).
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1.0
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 Colette
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Wholesome Crossdresser / int_43de9426
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Wholesome Crossdresser
 Wholesome Crossdresser / int_4462f8
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Miyashita Masashi from Onii-chan to Issho (official English title: Me & My Brothers). His official reason for this is due to his profession as a romance novelist, whose demographic for his novels is women. Masashi constantly crossdresses and Cosplays as a means of better understanding the female mind and applying this knowledge to write successful stories. The real motivation is possibly revealed in the last chapter of the manga, where in junior high, while Sakura is about three years old and Masashi about fourteen, he had to dress as a junior high school girl for a student-run film project, much to Masashi's chagrin. Later, he admits that Sakura enjoys it when he dresses femininely, so it might not be such a bad thing after all.
 Wholesome Crossdresser / int_4462f8
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1.0
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1.0
 OniichanToIssho
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Wholesome Crossdresser / int_4462f8
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Wholesome Crossdresser
 Wholesome Crossdresser / int_44fe781e
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In one Neon Genesis Evangelion fanfic, Shinji raids Asuka's clothes to try out cross-dressing in an effort to gain acceptance from his father who raised a girl instead of him. Of course, Asuka throws a fit when she finds out as she thinks Shinji and Kaworu (who happened to be on-scene) are doing perverted things (they aren't, the fic is entirely SFW); once she calms down, she offers to correct Shinji's appearance.
 Wholesome Crossdresser / int_44fe781e
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1.0
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1.0
 Neon Genesis Evangelion
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Wholesome Crossdresser / int_44fe781e
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Wholesome Crossdresser
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Whateley Universe:
Numerous characters, being Transgender, dress as the opposite gender until they have the opportunity to change physical sex. Others have already done so, but choose to wear the same clothes that they always have done. Phase is a wealthy boy who looks entirely female except for the genitalia, forcing him to have custom made clothes with a masculine cut but a feminine fit except for a loose groin. Presumably many other students in Poe house, though they are not mentioned.
Although there is one character who is not in Poe Cottage and cross-dresses. Gotterdammerung cross-dresses because he likes it and the story that focuses on him has him unsure if he should cross-dress for Halloween.
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1.0
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1.0
 Whateley Universe
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Wholesome Crossdresser / int_4522fd1
 Wholesome Crossdresser / int_46527eea
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Wholesome Crossdresser
 Wholesome Crossdresser / int_46527eea
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An episode of Michiko & Hatchin had Hatchin meeting a man whose job involves him being a cross-dressing actor. While he wears men's clothes outside of work, his son dresses as a girl 24/7 and wants to be a female impersonator like his father when he grows up.
 Wholesome Crossdresser / int_46527eea
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1.0
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1.0
 Michiko & Hatchin
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Wholesome Crossdresser / int_46527eea
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Wholesome Crossdresser
 Wholesome Crossdresser / int_4660bd1d
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In Kinky Boots main character Lola may be a performer who can dish out some truly mean words when she needs to, but when faced with ignorant and homophobic comments actively spreads understanding. 'Ask any woman what she likes most in a man: Compassion, Tenderness, Sensitivity. Traditionally female virtues. Perhaps what women truly want is a man that is fundamentally a woman.'
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1.0
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1.0
 Kinky Boots
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Wholesome Crossdresser / int_4660bd1d
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Wholesome Crossdresser
 Wholesome Crossdresser / int_471fe06b
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In Portlandia, Fred Armisen plays the feminine brunette Nina while Carrie Brownstein plays her boyfriend, the more masculine Lance (with a masked voice). They both do it convincingly.
 Wholesome Crossdresser / int_471fe06b
featureApplicability
1.0
 Wholesome Crossdresser / int_471fe06b
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1.0
 Portlandia
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Wholesome Crossdresser / int_471fe06b
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Wholesome Crossdresser
 Wholesome Crossdresser / int_475df441
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Dana and other Elle-Boys in the Jet Dream Remix Comic always dress as females but are fairly chaste and strictly heterosexual, apparently due to the (fictional) publisher's misguided attempt to pass The Comics Code and/or Publisher Appeal.
 Wholesome Crossdresser / int_475df441
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1.0
 Wholesome Crossdresser / int_475df441
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1.0
 Jet Dream (Webcomic)
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Wholesome Crossdresser / int_475df441
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Wholesome Crossdresser
 Wholesome Crossdresser / int_47ef1aa1
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Hans of The Daughter of Twenty Faces does this, albeit unwillingly, for a circus act the nakama are producing in episode 5 of the anime.
 Wholesome Crossdresser / int_47ef1aa1
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1.0
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1.0
 The Daughter of Twenty Faces (Manga)
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Wholesome Crossdresser / int_47ef1aa1
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type
Wholesome Crossdresser
 Wholesome Crossdresser / int_480fe694
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Noto Kanazawa aka Noto-sama, created by Axis Powers Hetalia's author Hidekaz Himaruya and the star of the short manga Advance! Kitakou Broadcasting Club. He's a cross-dressing School Newspaper Newshound who's often found stripping other people with his partner-in-crime, Yamato Nara from another Himaruya comic, Barjona Bombers.
It should be noticed that the Noto in the early Kitakou stories is virtually a completely different character. He isn't a WSC, just an Ordinary High-School Student and a bit of a Butt-Monkey, as well as being much less pushy. After the series added Pure to its title and Himaruya started drawing Barjona, Noto was revealed to be Cute and Psycho and snapped, starting on the path to his current incarnation. This era of the comic was taken off the website though, presumably due to Old Shame.
Koedo Chiba, a minor character in the Pure part of the series, is both this and a Bokukko. Due to having been made fun of as a child for looking like a boy, she opted to actually live her life as one.
As for Hetalia itself, Poland has dressed up in girls' clothes (usually miniskirts) in a few strips, which tends to weird out his Heterosexual Life Partner (or maybe not that heterosexual) Lithuania.
This is also part of Italy's backstory. Austria actually thought he was a girl until he hit puberty (it's somewhat implied that Hungary found out at some point, as she doesn't seem to be fazed by the discovery), and his first love Holy Roman Empire never found out that Italy was a male, always believing him to be a girl even when he left.
The child versions of Canada, Romano, and the US wore similar outfits. It's a Historical In-Joke.
As of Hetalia Bloodbath 2010, we've also had Hong Kong in a maid dress, and China in a qipao.
On the FtM side there was Hungary as a teenager, though she even managed to confuse herself with it, and so is maybe more an example of Raised as the Opposite Gender or possibly even being Transgender...or maybe an entirely different trope known as "Hungarian Gender Confusion" in the fandom.
 Wholesome Crossdresser / int_480fe694
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1.0
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1.0
 Axis Powers Hetalia / Web Comic
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Wholesome Crossdresser / int_480fe694
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Wholesome Crossdresser
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In the Many Quirks Persona series, both Akira and Yu enjoy crossdressing for various reasons. Akira takes it up as part of his job at Crossroads and takes to it too well, using it as disguises to spy on Akechi and mess with Ryuji, and even roping several of his fellow thieves into it. Yu treats it as Serious Business from the get-go, jumping at the chance to take part in the "Miss" Yasogami pageant, and even donning a voice changer to complete the image.
 Wholesome Crossdresser / int_4886528
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1.0
 Wholesome Crossdresser / int_4886528
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1.0
 The Many Quirks Of Phantom Thievery (Fanfic)
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Wholesome Crossdresser / int_4886528
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Wholesome Crossdresser
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In several episodes of Hayate the Combat Butler, poor Hayate is forced by Nagi to crossdress in blatantly female costumes like sailor fuku or a catgirl costume. The fact that Hayate's physical and facial features are sexually ambiguous mean that some of the male characters may get the wrong idea... Hayate's tendency to act Moe in these types of situations doesn't help, either.
It's so wholesome that he actually has a male over the top in love with him. He ends up crushed when Hayate is exposed as a man...for all of half of chapter before turning "It's okay if it's you".
Its even worse in the manga: Ruka first meets Hayate when he is crossdressed (long story). When she later sees him in his butler uniform, she asks if he's a girl who likes to wear boys clothes. How well Hayate fits here is even a bit of a Running Gag in the manga.
 Wholesome Crossdresser / int_495f277f
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1.0
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1.0
 Hayate the Combat Butler (Manga)
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Wholesome Crossdresser / int_495f277f
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Wholesome Crossdresser
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Tip Wilkins from Skin Horse is a cheerful The Casanova in a dress. He's fashion conscious and uses a variety of complex female outfits, but he makes no attempt to appear female (although given the art style, it can be a bit hard to tell). This is some kind of strange self-flagellation on part of the artist, whose previous Narbonic starred four obsessives who didn't always keep track of whether they were wearing pants.
Of course, it's also part of the Land of Oz motif, specifically to Princess Ozma.
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1.0
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 Skin Horse (Webcomic)
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Wholesome Crossdresser / int_498b77e9
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Wholesome Crossdresser
 Wholesome Crossdresser / int_49a87cb3
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In Final Fantasy VII, hero Cloud Strife has to rely on the help of some friendly transvestites so that he can disguise himself as a woman and infiltrate a gangster's mansion.
 Wholesome Crossdresser / int_49a87cb3
featureApplicability
1.0
 Wholesome Crossdresser / int_49a87cb3
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1.0
 Final Fantasy VII (Video Game)
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Wholesome Crossdresser / int_49a87cb3
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Wholesome Crossdresser
 Wholesome Crossdresser / int_49b0f863
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It appears in DOUBLE K that nearly 90% of Kamina's plans involve putting Simon in drag.
 Wholesome Crossdresser / int_49b0f863
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1.0
 Wholesome Crossdresser / int_49b0f863
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1.0
 DOUBLE K (Webcomic)
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Wholesome Crossdresser / int_49b0f863
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Wholesome Crossdresser
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Nezumi from No. 6 frequently has to dress as a woman in order to perform his act in plays, and makes a rather convincing woman at that.
 Wholesome Crossdresser / int_49f7545d
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1.0
 Wholesome Crossdresser / int_49f7545d
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 No. 6
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Wholesome Crossdresser / int_49f7545d
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Wholesome Crossdresser
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It's hinted in The Binding of Isaac that all of the alternate characters in the game are possibly just Isaac wearing different wigs and accessories. This includes the three female characters, Eve, Magdalene, and Lilith.
 Wholesome Crossdresser / int_4c56381b
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1.0
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1.0
 The Binding of Isaac (Video Game)
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Wholesome Crossdresser / int_4c56381b
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Wholesome Crossdresser
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The whole shtick of Chotto Edo Made is about a girl who dresses like a boy and her love interest, a boy who dresses and acts cutesy like a girl (with eyelashes to boot).
 Wholesome Crossdresser / int_4fab02d4
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1.0
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1.0
 ChottoEdoMade
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Wholesome Crossdresser / int_4fab02d4
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Wholesome Crossdresser
 Wholesome Crossdresser / int_4fd9904a
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In Harry Potter and the Order of the Phoenix, Sirius mentions Fletcher has been dressing up as a witch as a disguise after Sturgis lost Moody's best invisibility cloak when he was arrested.
 Wholesome Crossdresser / int_4fd9904a
featureApplicability
1.0
 Wholesome Crossdresser / int_4fd9904a
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1.0
 Harry Potter and the Order of the Phoenix
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Wholesome Crossdresser / int_4fd9904a
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Wholesome Crossdresser
 Wholesome Crossdresser / int_4ff52d04
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In The Legend of Zelda: Tri Force Heroes there are various costumes that grant Link special abilities if he wears them. These include Zelda's dress◊, a cheerleader outfit, and a Queen of Hearts dress.
 Wholesome Crossdresser / int_4ff52d04
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1.0
 Wholesome Crossdresser / int_4ff52d04
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1.0
 The Legend of Zelda: Tri Force Heroes (Video Game)
hasFeature
Wholesome Crossdresser / int_4ff52d04
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Wholesome Crossdresser
 Wholesome Crossdresser / int_5063d8b4
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In Pinocchio and the Emperor of the Night, Scalawag and Igor use cross-dressing in an attempt to save Pinocchio from his illusion.
 Wholesome Crossdresser / int_5063d8b4
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1.0
 Wholesome Crossdresser / int_5063d8b4
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1.0
 Pinocchio and the Emperor of the Night
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Wholesome Crossdresser / int_5063d8b4
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Wholesome Crossdresser
 Wholesome Crossdresser / int_5080fa73
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G in From Eroica with Love.
 Wholesome Crossdresser / int_5080fa73
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1.0
 Wholesome Crossdresser / int_5080fa73
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1.0
 From Eroica with Love (Manga)
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Wholesome Crossdresser / int_5080fa73
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Wholesome Crossdresser
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Jane from Homestuck is a sweet, caring, practical girl who also happens to really love wearing fake moustaches in the style of famous detectives from novels.
 Wholesome Crossdresser / int_50bcf7a6
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1.0
 Wholesome Crossdresser / int_50bcf7a6
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1.0
 Homestuck (Webcomic)
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Wholesome Crossdresser / int_50bcf7a6
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Wholesome Crossdresser
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Terence, the squire in Gerald Morris's The Squire's Tales, crossdresses to help rescue Sir Gawain from a dungeon.
 Wholesome Crossdresser / int_51b928a3
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1.0
 Wholesome Crossdresser / int_51b928a3
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1.0
 The Squire's Tales
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Wholesome Crossdresser / int_51b928a3
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Wholesome Crossdresser
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Alfred Violon from SWAP Ensemble always wears a skirt or a dress. At one point, he dresses up as another male crossdresser, states that he's wearing boys' clothes for once, and tells people to stop making assumptions about his gender.
 Wholesome Crossdresser / int_51e91793
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1.0
 Wholesome Crossdresser / int_51e91793
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 SWAP Ensemble / Web Comic
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Wholesome Crossdresser
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Ayumu from Is This a Zombie?, as he's drafted into a Magical Girl army after his zombie nature absorbs most of Haruna's powers, including the ability to transform into a Masou Shoujo.
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 Is This a Zombie?
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Wholesome Crossdresser
 Wholesome Crossdresser / int_52e8fba
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Of course, it's also part of the Land of Oz motif, specifically to Princess Ozma.
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1.0
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 Land of Oz
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Wholesome Crossdresser
 Wholesome Crossdresser / int_5639c58b
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In Black Adventures, Black and N usually fight evil in skimpy Magical Girl costumes. Burgh and Elesa crossdress for fun (and to titillate the fans, apparently). The writer seems to have a thing for cross-dressing.
 Wholesome Crossdresser / int_5639c58b
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1.0
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 Black Adventures (Webcomic)
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Wholesome Crossdresser
 Wholesome Crossdresser / int_579b991b
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Subverted in Leave It to Beaver, where Wally is cast to play a saloon-girl in a "Summer Stock" Western; he hates the idea so much, that he ends up conning the perfect person for the role into taking it— Eddie Haskell.
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 Leave It to Beaver
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Wholesome Crossdresser
 Wholesome Crossdresser / int_58808436
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Keiichi in Higurashi: When They Cry is forced to crossdress on at least two occasions as part of the club's punishment games. It happens even more frequently in the manga. The artist really seems to like throwing in fanservice of the various males of the series crossdressing, usually as mini-comics or splash pages between chapters.
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1.0
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 Higurashi: When They Cry (Visual Novel)
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Wholesome Crossdresser / int_58808436
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Wholesome Crossdresser
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Persona 2 has Jun Kurosu, who not only has crossdressing listed as one of his official profile talents, but also has contact with Lisa demonstrating just how damn well he can cross-dress.
 Wholesome Crossdresser / int_59215319
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1.0
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 Persona 2 (Video Game)
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Wholesome Crossdresser / int_59215319
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Wholesome Crossdresser
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Persona 4:
Naoto Shirogane is a woman masquerading as a man.
Another example would be Teddie in his human form, who can pull off cosplaying Alice. The other boys in the cross-dressing pageant could count too, but the student body has rather negative opinions about it.
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 Persona 4 (Video Game)
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Wholesome Crossdresser
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Persona 5 has Lala Escargot, a Drag Queen and the proprietor of a gay bar in Shinjuku. She is also one of the few people trusted by Intrepid Reporter (and Devil Confidant) Ichiko Ohya, and always has the Player Character's best interest at heart, cautioning him to be careful on his way home. The protagonist can work for her as a part-time bartender, and she's actually quite the benevolent employer.
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1.0
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1.0
 Persona 5 (Video Game)
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Wholesome Crossdresser / int_5921531c
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Wholesome Crossdresser
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Several in Racing Daylight, which takes place half during The American Civil War and half in the modern world. Back in time, Rev. Potts (played by John Seidman) is married to Henrietta (actress Denny Dillon) who "we all knew was a man". In modern times, Seidman plays Busy-Body, who is either a cross-dressing gay man or a pre-op transgender woman. Dillon plays the Gossip, who wears overalls and fixes trucks and objects to being called a woman. Another male character paints his toenails in a whimsical moment, while a friend chortles "Nobody's telling RuPaul to take off HIS dress."
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1.0
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Wholesome Crossdresser
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Cruz, from NEEDLESS, unwillingly dresses as a girl in the later part of the manga (and ended up popular with his teammates as well as the readers) in order to survive at an all-girls Academy. The academy uniform becomes his default outfit for the rest of the series, initially because his original clothes were thrown away, and then gets a bounty on his head and has to remain cross-dressing to avoid attention from his enemies, and later just because his companions shoot down the idea of wearing boys' clothes again when he brings it up. A popular nickname for this version of him is "Yamada-ko". As of manga chapter 113, Cruz is officially changed into a female by Blade's godly powers, to the amusement of the majority of his companions.
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 NEEDLESS (Manga)
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Wholesome Crossdresser / int_5b5183fb
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Wholesome Crossdresser
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Sister from Arakawa Under the Bridge. The man wears a nun's habit for day-to-day life and on one occasion donned a schoolgirl uniform.
 Wholesome Crossdresser / int_5bbcf726
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1.0
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 Arakawa Under the Bridge (Manga)
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Wholesome Crossdresser / int_5bbcf726
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Wholesome Crossdresser
 Wholesome Crossdresser / int_5bd6bb99
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Nanashi, the protagonist of Shin Megami Tensei IV: Apocalypse, can put on some lolita dresses that can be bought in the Ginza members-only shop, and yes, they appear on his 3D model. It doesn't make him any less heroic.
 Wholesome Crossdresser / int_5bd6bb99
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1.0
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1.0
 Shin Megami Tensei IV: Apocalypse (Video Game)
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Wholesome Crossdresser / int_5bd6bb99
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Wholesome Crossdresser
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In Hussar Ballad 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.
 Wholesome Crossdresser / int_5cd7e19a
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1.0
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Wholesome Crossdresser
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Black Butler:
Ciel in episode 4 of the anime, he sneaks into a ball in a very...special outfit◊. Keep in mind that he's a twelve-year-old boy who runs his own company. This outfit is famous in the series, to the point of where it even has its own fanbase and cosplay design. Heck, it's much more famous and recognized than even his regular clothes. It's really saying something when, by searching the term "Ciel Phantomhive" in Google Images, 99% of the pictures that pop up are of him in that outfit. Anyone who didn't know the series would probably be under the impression that he is a she.
Sieglinde Sullivan does it, too. Even before she has to swap clothes with Ciel as a disguise, when she wishes to wear clothes from the "outside world" and Sebastian tells her Ciel's are the only clothes her size available, she's more than okay with it (it's her staff who won't let her). Though in Sieglinde's case, she probably simply doesn't care as long as it's something different.
 Wholesome Crossdresser / int_5ce2f08b
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1.0
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Wholesome Crossdresser / int_5ce2f08b
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Wholesome Crossdresser
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Sally Sweet in the Stephanie Plum series. He's described as not exactly attractive and nearly every other sentence out of his mouth is a Cluster F-Bomb, but he is depicted as a basically nice guy (even if he's the only school bus driver around who carries an Uzi under his seat).
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1.0
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1.0
 Stephanie Plum
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Wholesome Crossdresser / int_5d00b56c
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Wholesome Crossdresser
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Exalted has a few cultural examples as part of the background:
In the West are the Tya, a "third gender" of women who adopt male social roles in order to work as sailors. This is mainly because the waters of the West are overseen by hag-like spirits known as storm mothers, who will try to sink any boat that's crewed by any woman prettier than themselves. Which is pretty much every mortal woman in Creation, and most of the dead ones.
The city of Chiaroscuro is overseen by the Delzahn, who are pretty firm on gender roles - men defend and supply the household, women run it but don't do much on the outside. However, it allows men and women the option of becoming Dereth - they basically can dress and act like the other gender, as long as they wear a gray sash at all times in order to avoid confusion.
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1.0
 Exalted (Tabletop Game)
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Wholesome Crossdresser / int_5e150650
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Wholesome Crossdresser
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Loran Cehack's female alter-ego Laura Rolla in ∀ Gundam.
 Wholesome Crossdresser / int_5ec0f48
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1.0
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1.0
 ∀ Gundam
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Wholesome Crossdresser / int_5ec0f48
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Wholesome Crossdresser
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Fence has Bobbi who likes dressing up in girl's clothing including hair decorations.
 Wholesome Crossdresser / int_5f05f395
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1.0
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1.0
 Fence / Comicbook
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Wholesome Crossdresser / int_5f05f395
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Wholesome Crossdresser
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Dave in Degrassi wore a long frilly skirt to prove a point when Adam made him uncomfortable.
 Wholesome Crossdresser / int_5f1fe75b
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1.0
 Wholesome Crossdresser / int_5f1fe75b
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1.0
 Degrassi
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Wholesome Crossdresser / int_5f1fe75b
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Wholesome Crossdresser
 Wholesome Crossdresser / int_6040c28d
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Mayotama from I Can't Understand What My Husband Is Saying has a very feminine build, enough for Kaoru and Miki to confuse him for Hajime's younger sister rather than his brother. He also holds his arms as if he was a woman covering her breasts when he's in a hot spring.
 Wholesome Crossdresser / int_6040c28d
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1.0
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1.0
 I Can't Understand What My Husband Is Saying (Manga)
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Wholesome Crossdresser / int_6040c28d
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Wholesome Crossdresser
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Barney also disguises himself as Fred's girlfriend in The Jetsons Meet the Flintstones so they can gain access to a poker game with Mr. Slate without being recognized.
 Wholesome Crossdresser / int_60427ba2
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1.0
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1.0
 The Jetsons Meet the Flintstones
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Wholesome Crossdresser / int_60427ba2
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Wholesome Crossdresser
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RAIN:
Rudy is a gay male who sometimes crossdresses and calls himself Ruby. In contrast, Rain does not crossdress normally since as a transgender girl she identifies as female and dresses as such. However, when Rain is forced to wear typical boy clothes in order to not out herself to her brother, that is crossdressing (and the author knows that therefore this trope applies to her). Therefore, when Rudy poses as "Ryan's girlfriend" they are both crossdressing at that point.
And then there is Kylie, who chooses clothing to reflect the gender they currently identify as and never actually crossdresses if they can help it because it causes them to feel dysphoria.
 Wholesome Crossdresser / int_6056ce6b
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1.0
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1.0
 RAIN (Webcomic)
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Wholesome Crossdresser / int_6056ce6b
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Wholesome Crossdresser
 Wholesome Crossdresser / int_60f02ddb
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Roger from American Dad!. He himself is anything but wholesome, but his frequent cross-dressing is never portrayed negatively.
 Wholesome Crossdresser / int_60f02ddb
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1.0
 Wholesome Crossdresser / int_60f02ddb
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1.0
 American Dad!
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Wholesome Crossdresser / int_60f02ddb
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Wholesome Crossdresser
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Also, in the main storyline, he consistently wears a furisode note usually reserved for unmarried women and, traditionally, gay lovers whenever he wears kimono. This includes the gang's stay in Japan, as well as the cover art of a couple of chapters. Unlike in Horitsuba Gakuen, the kimonos he wears in Tsubasa -RESERVoir CHRoNiCLE- are worn in a masculine fashion; however, they are identifiable as furisodes due to the sleeve length.
 Wholesome Crossdresser / int_61b1bd67
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1.0
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1.0
 Tsubasa Reservoir Chronicle (Manga)
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Wholesome Crossdresser / int_61b1bd67
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Wholesome Crossdresser
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In Kira-Kira, Shika is forced to crossdress against his will. Interestingly enough, despite getting more male fans than the real girls in the band, people do catch on that he's a guy through things such as the shape of his hands. He's quite relieved when he's allowed to stop not just because he was tired of getting hit on/thought of as a pervert because he was starting to get used to it. He's still a wholesome crossdresser five years later, in Curtain Call.
 Wholesome Crossdresser / int_6244139e
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1.0
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1.0
 Kira-Kira (Visual Novel)
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Wholesome Crossdresser / int_6244139e
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Wholesome Crossdresser
 Wholesome Crossdresser / int_6250d2c3
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Paul "the transvestite stalker" from College Roomies from Hell!!! - granted, a bisexual prostitute and a bit of a harasser, but still a generally positive influence on the cast once he becomes a genuine character rather than a Running Gag, serving as the voice of reason essentially whenever he plays a significant role.
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1.0
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1.0
 CollegeRoomiesFromHell
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Wholesome Crossdresser / int_6250d2c3
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Wholesome Crossdresser
 Wholesome Crossdresser / int_6276800c
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In the Hooker Verse, The Nostalgia Critic wears a corset and skirt. Of course, the 'wholesome' part is a little debatable given that he's, well, a hooker, but...
 Wholesome Crossdresser / int_6276800c
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1.0
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1.0
 The Nostalgia Critic (Web Video)
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Wholesome Crossdresser / int_6276800c
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Wholesome Crossdresser
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TwoKinds has Natani, who literally has a male soul after her own was magically demolished. The conflict of male mind versus female instinct is an ongoing plotline, especially in regards to Natani's relationship with Keith.
 Wholesome Crossdresser / int_63053ca
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1.0
 Wholesome Crossdresser / int_63053ca
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 TwoKinds (Webcomic)
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Wholesome Crossdresser / int_63053ca
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Wholesome Crossdresser
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Olivie from the Angélique series of dating sims for girls. Yes, he is a possible love interest in every game he appears in.
 Wholesome Crossdresser / int_63fc7686
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1.0
 Wholesome Crossdresser / int_63fc7686
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 Angélique (Video Game)
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Wholesome Crossdresser / int_63fc7686
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Wholesome Crossdresser
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James Fitzjames on The Terror wistfully considers wearing a Renaissance-style costume gown to the expedition's morale-boosting carnival and admires the effect the dress has on him while holding it against his body, but ends up settling for the more plausibly deniable choice of dressing as Britannia, the patron goddess of the British Empire- still technically crossdressing, but less overtly because Britannia herself is depicted in masculine armor over her dress.
 Wholesome Crossdresser / int_6401889e
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1.0
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1.0
 The Terror
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Wholesome Crossdresser / int_6401889e
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Wholesome Crossdresser
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Woody Woodpecker has done this time to time, the most memorable instances being Chew-Chew Baby, Drooler's Delight and The Woody Woodpecker Polka.
 Wholesome Crossdresser / int_6633a097
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1.0
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 Woody Woodpecker
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Wholesome Crossdresser / int_6633a097
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Wholesome Crossdresser
 Wholesome Crossdresser / int_678356d7
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In Welcome to Room #305 there's Yoon Sung, who likes to dress up as a woman at night. Subverted when it's revealed that it's actually his twin sister.
 Wholesome Crossdresser / int_678356d7
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-0.3
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1.0
 Welcome To Room 305 (Webcomic)
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Wholesome Crossdresser / int_678356d7
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Wholesome Crossdresser
 Wholesome Crossdresser / int_67ce5a04
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Forrest in Fire Emblem Fates crossdresses because of his love for female clothing, and because his father Leo once said he looked adorable in a dress when he was very young. He's so feminine that he's mistaken for a woman when his aunt Elise first meets him.
 Wholesome Crossdresser / int_67ce5a04
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1.0
 Wholesome Crossdresser / int_67ce5a04
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1.0
 Fire Emblem Fates (Video Game)
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Wholesome Crossdresser / int_67ce5a04
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Wholesome Crossdresser
 Wholesome Crossdresser / int_68c7e5cd
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Alto Saotome from Macross Frontier used to be a Kabuki actor before he became a pilot. As a result, he retains a very feminine look even when wearing male clothing. This is Lampshaded by his friends, who often tease him and call him "Princess Alto" due to his appearance. People who don't know Alto will sometimes mistake him for a girl. It doesn't really help when some fans admit that they find Alto hotter and more attractive than his own mother. Taken to a higher level in the second movie where Also dresses up as a maid.
 Wholesome Crossdresser / int_68c7e5cd
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1.0
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1.0
 Macross Frontier
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Wholesome Crossdresser / int_68c7e5cd
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Wholesome Crossdresser
 Wholesome Crossdresser / int_6a8aff51
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The Stormlight Archive: Ardents, the priestly caste of the Vorin religion, are allowed to ignore most of the usual Vorin rules for gender roles: Ardents can eat men's or women's food regardless of their gender, male ardents are allowed to be literate, etc.
 Wholesome Crossdresser / int_6a8aff51
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1.0
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1.0
 The Stormlight Archive
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Wholesome Crossdresser / int_6a8aff51
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Wholesome Crossdresser
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In Fallout 4, all clothing items have unisex designs, allowing cross-dressing of the player character.
 Wholesome Crossdresser / int_6c1d09b4
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1.0
 Wholesome Crossdresser / int_6c1d09b4
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1.0
 Fallout 4 (Video Game)
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Wholesome Crossdresser / int_6c1d09b4
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Wholesome Crossdresser
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Fushigi Yuugi:
Chou Ryuuen aka Nuriko. His actual gender is revealed pretty early on in the series.
Bishounen Hotohori, while usually just mistaken to be a woman (especially by Miaka during their first meeting), with minimal effort he has on occasion been a Wholesome Crossdresser . He had to enamor a band of thugs by pouring drinks for them (he only had to powder his face) and in the manga when he, Miaka and the Suzaku Seishi visited a females-only public bath where all of the males were temporarily Wholesome Crossdressers (he and Nuriko were the only men convincingly looking like women, to the chagrin of the others).
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1.0
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1.0
 Fushigi Yuugi (Manga)
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Wholesome Crossdresser / int_6c5e0560
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Wholesome Crossdresser
 Wholesome Crossdresser / int_6d8311c4
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In Pokémon Crystal, if you choose the female trainer, the overworld sprite changes from female to male if you do any game link cabling with any of the other six games. Yes, even with another Crystal version.
 Wholesome Crossdresser / int_6d8311c4
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1.0
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1.0
 Pokémon Gold and Silver (Video Game)
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Wholesome Crossdresser / int_6d8311c4
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Wholesome Crossdresser
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Mike in StarTropics crossdresses (or maybe magically changes gender) to enter an all-female village.
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Shugo Chara! has Nadeshiko; her relatives explaining this is a technicality of her family's dance career. The only two hints at this is her transformation is into a polearm-wielding maniac, similar to Tadase's ironic change, and not swimming. Interestingly, she is Put on a Bus before anyone but the audience finds out (Amu is just smitten with her 'twin brother' for the day) though seems amused when she thinks how she'll officially explain it to Amu when she returns.
Interestingly, at this point there's more than a few gags that the show was becoming a Cast Full of Pretty Boys in regards to the 'normal characters', with her Chara teasing Amu's habit of crushing on every - one.
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Wholesome Crossdresser
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In Basquash!, Princess Flora Skybloom takes off to the city, to watch the protagonist's development close-up. To hide the fact that she's royalty, she disguises herself as a boy, hiding her hair beneath a baseball cap and taking on the name Alan Naismith. She does a pretty good job of disguising it, too, except that she was unable to restrain her love for the extremely girly Idol Band, Eclipse.
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Wholesome Crossdresser
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The cheer team crossdresses as part of their performance at the sports festival in Kaguya-sama: Love Is War. Ishigami (who had joined in the hopes that it would make him happier and more social), ends up borrowing Kaguya's uniform for the event, and the scene where she has him try it on to see if it fits is the first real moment of what would become an incredibly wholesome sibling-like bond between the two.
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Wholesome Crossdresser
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Chihiro Fujisaki from Danganronpa: Trigger Happy Havoc. It becomes an important plot point in Chapter 2 due to where the murder occurred. During that chapter, it is also revealed that he resorted to pretending to be a girl in order avoid the constant pressure put on him for being a weak male, but this facade only resulted in him hating himself for not being able to face his own weakness.
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 Danganronpa: Trigger Happy Havoc (Visual Novel)
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Wholesome Crossdresser
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Husky from +Anima is introduced in the series as a pretty Mermaid Princess. Later you find out the pretty pretty princess is actually a boy cross-dressing for cash. Later, after being kidnapped and sold as a slave in Sailand, he dresses up like a girl so he'll sell for a higher price. Cooro and Nana come to take him from his Master's home, and neither of them can tell that the fish + anima is actually Husky in a wig and girly clothes until they get right up in his face.
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Wholesome Crossdresser
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Tomodachi Life will let you dress Miis in clothes that don't match their gender. Miis don't seem to appreciate being put in opposite-gender clothing most of the time, so if you like making one or more of your Miis crossdress expect to hear the "doesn't like it" jingle again and again.
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Wholesome Crossdresser
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Then, in Choujin Sentai Jetman, the one cross-dressing was... Raita/Yellow Owl, in order to trick a Monster of the Week who absorbs women's voices. He successfully pulls it off, too - apparently, even fatties can make convincing women with just some makeup, a wig, and a kimono.
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 Choujin Sentai Jetman
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Wholesome Crossdresser
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Happens in Chapter 17 of A Day Indoors. Negi wonders if the frilly pink panties were necessary, really. Yuuna certainly seems to think they are.
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 ADayIndoors
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Wholesome Crossdresser
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In Don Juan DeMarco, the title character (played by Johnny Depp) is at one point enslaved, and sold to a lusty Sultana. To prevent the Sultan from discovering her new personal attendant is an entirely 'unaltered' male, she disguises her new toy (most fetchingly!◊) in a loose-fitting jeweled sari. (One could suspect that the script-writers invented this to showcase Depp's talent for female impersonation, but it's actually lifted from Lord Byron's epic poem Don Juan.)
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Wholesome Crossdresser
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Material Girl features a teenager forced into this.
 Wholesome Crossdresser / int_76d9143a
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1.0
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 Material Girl (Webcomic)
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Wholesome Crossdresser
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Touken Ranbu, a game which features Anthropomorphic Personifications of Japanese swords as young men, has Midare Toushirou, who fights while wearing a dress. It's this way because the weapon he's based on has a wavy line pattern and not a straight one. His powered-up Kiwame form ratchets up the girliness even further, with more frills and ribbons, giving the appearance of a Magical Girl.
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Wholesome Crossdresser
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Superman's Pal Jimmy Olsen has disguised himself as a woman... more than a few times, actually. He's rather good at it.
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1.0
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 Superman
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Wholesome Crossdresser
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Steven Universe:
In "Sadie's Song", Steven happily dressed up in a crop top, skirt, and makeup when serving as a last-minute substitute for Sadie Miller's musical performance, and nobody judged him for it. It's not played for laughs or creep factor at all.
In "Diamond Days", Steven has the Pebbles make a version of Pink Diamond's outfit in his size for him to wear at the ball because he feels he should "dress for the occasion". He doesn't seem to mind wearing it. The only factor that ever makes this uncomfortable for anybody is the fact that he's being shoehorned into his mother's old role on Homeworld during this arc.
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 Steven Universe
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Wholesome Crossdresser
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Reality TV example: Derrick Barry of America's Got Talent
 Wholesome Crossdresser / int_78621bac
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1.0
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 America's Got Talent
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Wholesome Crossdresser / int_78621bac
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Wholesome Crossdresser
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DEA Agent "Denise" Bryson on Twin Peaks, played by David Duchovny. (Who, as it turns out, has really nice legs.) Also a rare case of a heterosexual crossdresser on network TV.
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 Twin Peaks
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Wholesome Crossdresser / int_78fc0025
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Wholesome Crossdresser
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Azami in Himawari! is a male spy at an all-girls' ninja school, and wears the appropriate clothing. Everyone knows he's a guy and doesn't mind, because the whole spy thing means inside info for both sides.
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Wholesome Crossdresser / int_7b706e62
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Wholesome Crossdresser
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Nononono is a ski-jumping manga by the author of Elfen Lied. The heroine Nonomiya is cross-dressing and passing for her dead twin brother because only men are allowed in professional ski-jumping... and she wants to win Olympic gold. Played very seriously.
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Wholesome Crossdresser / int_7c478250
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Wholesome Crossdresser
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Both Fred and Barney of The Flintstones do this oddly often. Barney does it VERY often in the Fruity Pebbles ads, presumably just to get Fred's Pebbles.
Barney also disguises himself as Fred's girlfriend in The Jetsons Meet the Flintstones so they can gain access to a poker game with Mr. Slate without being recognized.
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1.0
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 The Flintstones
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Wholesome Crossdresser / int_7d122312
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Wholesome Crossdresser
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In Hands Held In The Snow, Tia Knoll, the very rich and very sly nobleman, crossdresses in almost every appearance so far. Nobody comments on it much beyond curiosity, but he likes to flaunt his sparkly wigs and dresses.
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Wholesome Crossdresser / int_7db16a43
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Wholesome Crossdresser
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In the pilot of Drake & Josh, it's revealed that Josh dresses up as a woman in order to write an advice column for the school newspaper. Of the two brothers, Josh is easily the nicer and kinder one.
 Wholesome Crossdresser / int_7dbde88b
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1.0
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 Drake & Josh
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Wholesome Crossdresser / int_7dbde88b
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Wholesome Crossdresser
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Natsume, from Tokyo Ravens dresses as a boy in public.
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 Tokyo Ravens
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Wholesome Crossdresser
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Gintama has the Okama bar that created the lovely Paako and Zurako. Gintoki, Shinpachi and even Kagura have no problems crossdressing when they need to...or just for the hell of it, actually. And there's also Yagyuu Kyuubei.
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Wholesome Crossdresser
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Éowyn, so she can fight in the final battle, from The Lord of the Rings
 Wholesome Crossdresser / int_7fc78282
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 The Lord of the Rings
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Wholesome Crossdresser / int_7fc78282
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Wholesome Crossdresser
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Played more than usually straight in Ed Wood: Ed is shown to be a heterosexual who happens to find women's clothing more attractive and comfortable. This is probably because he was based on an actual person.
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 Ed Wood
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Wholesome Crossdresser
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The tenants, particularly Yuki, frequently dress up as women for various convoluted reasons in The Wallflower.
 Wholesome Crossdresser / int_82c81aaa
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1.0
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Wholesome Crossdresser
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The entire premise of Princess Princess is about pretty boys dressing up as "princesses" to provide refreshment for the other students of the all-boys school.
 Wholesome Crossdresser / int_8323f6be
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Wholesome Crossdresser
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Both of the leads of Penguin Revolution are Wholesome Crossdressers. 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. Hilarity Ensues.
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Wholesome Crossdresser
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To Wong Foo, Thanks for Everything, Julie Newmar has John Leguizamo, Patrick Swayze, and Wesley Snipes all as cross-dressing drag queens. Vida and Noxeema even convince Chi-Chi to give up the boy she has a crush on to the girl in town who likes him, as it wouldn't be fair to him.
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 To Wong Foo, Thanks for Everything, Julie Newmar
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Wholesome Crossdresser
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In season two of Legend of the Seeker, Zedd has to dress up as an old woman to infiltrate a castle. He seems to have a lot of fun with it, even when one of the (male) castle residents becomes infatuated with him.
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Wholesome Crossdresser
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Kaeloo: Stumpy is frequently Dragged into Drag, but once admitted, under the effects of Truth Serum, that he does enjoy dressing up as a girl. In Season 2, he frequently argues with Pretty about who gets to be the "girl", to her annoyance. This has led to some... awkward instances◊.
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 Kaeloo
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Wholesome Crossdresser
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In Girl Genius's "Cinderella" side-story, the three Jaegermonster men get cast as the ugly stepsisters. Maxim (in purple) really seems to enjoy the role.
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Wholesome Crossdresser
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All three protagonists of The Adventures of Priscilla, Queen of the Desert, to varying degrees.Terence Stamp plays a hard-drinking but patient trans, Guy Pearce a bitchy, high-strung Performance Artist, and Hugo Weaving is the timid, sweet-natured drag queen who persuades them to do a cabaret act in the middle of the desert. That breaking sound you heard was your brain.
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 The Adventures of Priscilla, Queen of the Desert
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Wholesome Crossdresser
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Alec in Castlevania RPG
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 The Paladin
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Wholesome Crossdresser / int_890da597
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Wholesome Crossdresser
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Leslie Audette of Flaky Pastry, who is first introduced when Marelle and Nitrine are interviewing potential roommates. The author had originally planned for the two of them to be surprised by him (i.e. "Wait, you're a guy?), but then realized that Marelle wouldn't care, and Nitrine...would care either way.
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 Flaky Pastry (Webcomic)
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Wholesome Crossdresser
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Jack Donaghy of 30 Rock reveals that he exclusively wore hand me downs until he was 12. His older siblings were all girls.note "Apollo, Apollo": Season 3, Episode 16
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 30 Rock
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Wholesome Crossdresser / int_89bf8ce
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Wholesome Crossdresser
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Coronation Street, of all things, introduced Marc (aka, sometimes, "Marcia") in 2011, the show's first cross-dressing character (though Hayley, introduced in 1998, is a recurring Transgender character.) The show portrays Marc's dressing as both healthy and acceptable, with only unlikeable characters being against it.
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 Coronation Street
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Wholesome Crossdresser
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Marco Diaz from Star vs. the Forces of Evil crossdressed to infiltrate St. Olga's Reform School For Wayward Princesses. He not only leads a rebellion but his Princess Turdina persona becomes an Icon of Rebellion and he receives monthly royalty checks for merchandise. When Miss Heinous exposed him to the other princesses (right when he was about to confess the truth himself, ironically enough), the princesses are accepting of the revelation, saying he can be a princess if wants to.
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 Star vs. the Forces of Evil
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Wholesome Crossdresser
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In Waiting for Guffman, director Corky St. Clair might be a closeted example. He often buys clothes for his wife Bonnie, a reclusive lady who nobody ever seems to have met.
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 Waiting for Guffman
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Wholesome Crossdresser
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Gundam examples:
Loran Cehack's female alter-ego Laura Rolla in ∀ Gundam.
In a possible homage to Laura Rolla, Gundam 00's Tieria Erde dons a dress, long hair extensions, and a large set of fake breasts at one point in the second season. Why? So that he can sneak into a high class party and speak to Ribbons. And to make fangirls melt into a collective puddle over Stupid Sexy Girl!Tieria, while several fanboys went "TIERIA IS A MAN AND HE'S OURS!".
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 Gundam (Franchise)
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Wholesome Crossdresser / int_8ac4e993
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Wholesome Crossdresser
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In Takashi Kitano's Zatoichi, Geisha Seitaro 'Osei' Naruto is actually a man.
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1.0
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 Zatoichi (Franchise)
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Wholesome Crossdresser / int_8bc62500
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Wholesome Crossdresser
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Yellow Belmont from Genesis Climber MOSPEADA (Lancer/Yellow Dancer in Robotech).
 Wholesome Crossdresser / int_8c96b29e
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1.0
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 Genesis Climber MOSPEADA
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Wholesome Crossdresser / int_8c96b29e
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Wholesome Crossdresser
 Wholesome Crossdresser / int_8d7f29ec
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Wade "Unique" Adams from Glee; Shrinking Violet as a boy, Sassy Black Woman as a girl.
 Wholesome Crossdresser / int_8d7f29ec
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1.0
 Wholesome Crossdresser / int_8d7f29ec
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 Glee
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Wholesome Crossdresser / int_8d7f29ec
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Wholesome Crossdresser
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Max Klinger on M*A*S*H was a wholesome, if definitely not attractive or believably female, crossdresser. In fact, the lack of believability was deliberate; he crossdressed in order to get a Section-8 "insanity" discharge from the Army. When Radar left, Klinger became clerk and dropped his cross-dressing gig, though this was written in due to the actor's discomfort with the idea that his now-mature children might be able to watch their dad cross-dressing on TV each week.
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 M*A*S*H
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Wholesome Crossdresser / int_8d814070
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Wholesome Crossdresser
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In Monk, it turns out that Lieutenant Disher is good at being a female impersonator. In "Mr. Monk and the Missing Granny," he is seen disguised as a homeless woman, although Monk and Sharona see through it. Also, in "Mr. Monk and the Three Julies," he is disguised as their suspect's deceased mother's body as a trap to lure him out of hiding and get a confession. Their suspect falls for the disguise.
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 Monk
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Wholesome Crossdresser / int_8d81f086
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Wholesome Crossdresser
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Jodie from Soap dresses as a woman a few times during his "I want to be a woman" phase in season one.
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1.0
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 Soap
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Wholesome Crossdresser / int_8d84a932
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Wholesome Crossdresser
 Wholesome Crossdresser / int_8dba7131
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Alanna from Song of the Lioness. During her time, girls were not allowed to be knights so she had to disguise herself as a male to receive training.
 Wholesome Crossdresser / int_8dba7131
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1.0
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 Song of the Lioness
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Wholesome Crossdresser / int_8dba7131
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Wholesome Crossdresser
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In the original Sailor Moon manga, Naoko Takeuchi admits to drawing Haruka AKA Sailor Uranus manly when posing as a man. At the same time, the original Starlights are just crossdressers and don't ever change gender. None of this stops either Haruka OR Seiya from forming crushes on Usagi, though. Usagi herself does this in the anime episode "Cruise Blues" when she sneaks onto a cruise ship disguised as a handsome young freelance journalist. Also, the difference between Manga Uranus and Anime Uranus should be noted. In the anime, Haruka is drawn exclusively in men's clothes, and is mistaken as such a few times. Manga Haruka is shown wearing women's clothes just as often, even wearing the female School Uniform once she transfers to Juuban Highschool.
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1.0
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 Sailor Moon (Manga)
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Wholesome Crossdresser / int_8dd8ec81
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Wholesome Crossdresser
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Dragonslayer: Valerian turns out to be one. This was begun by her parents to spare her from the lottery of virgin girls being sacrificed.
 Wholesome Crossdresser / int_8def3d0b
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1.0
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 Dragonslayer
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Wholesome Crossdresser / int_8def3d0b
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Wholesome Crossdresser
 Wholesome Crossdresser / int_8df4eb7a
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Dramatic Dream Team: Rookies Shun Miyatake and Hiroshi Fukuda were made to dress like women and to entrances of Kazuki Hirata and Magnum HIRATA.
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1.0
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 Dramatic Dream Team (Wrestling)
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Wholesome Crossdresser
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Boy Meets World examples:
In S4E15 ("Chick Like Me"), Cory plans on dressing as a girl to school in order to find out how life is different for female students and male students. He turns out to have too masculine of a walk, so Shawn tries teaching him how to act female, getting it "surprisingly on the nose" according to Topanga. When he shows Cory how to walk like a woman and gets it perfectly, Cory and Topanga decide that Shawn should be the one to dress like a woman for the day. He turns out to be a babe. He also has a preferred "female" name (Veronica) and admits to having thought about doing this a lot before Cory ever decided to write the article.
In the much later episode "What a Drag", Eric Matthews decides that the only way for him and his best friend to avoid a local psycho and his gang, after almost getting them arrested, is to crossdress. They immediately turn to Shawn for help, and Shawn gives them a whole series of tips on how to crossdress correctly, so he clearly hasn't stopped since. Eric also decides to continue cross-dressing after the episode ends, just for his own sake. Notably, both characters are not only heterosexuals, but they are also actually three of the show's most prolific flirters.
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1.0
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 Boy Meets World
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Wholesome Crossdresser / int_8e193f0b
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Wholesome Crossdresser
 Wholesome Crossdresser / int_8ee238c9
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Persona:
Persona 2 has Jun Kurosu, who not only has crossdressing listed as one of his official profile talents, but also has contact with Lisa demonstrating just how damn well he can cross-dress.
Persona 4:
Naoto Shirogane is a woman masquerading as a man.
Another example would be Teddie in his human form, who can pull off cosplaying Alice. The other boys in the cross-dressing pageant could count too, but the student body has rather negative opinions about it.
Persona 5 has Lala Escargot, a Drag Queen and the proprietor of a gay bar in Shinjuku. She is also one of the few people trusted by Intrepid Reporter (and Devil Confidant) Ichiko Ohya, and always has the Player Character's best interest at heart, cautioning him to be careful on his way home. The protagonist can work for her as a part-time bartender, and she's actually quite the benevolent employer.
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 Persona (Franchise)
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Wholesome Crossdresser / int_8ee238c9
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Wholesome Crossdresser
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Timon of The Lion King ends up in a skirt in one scene ("What do you want me to do, dress in drag and do the hula?"), though since the animal characters don't normally wear anything it's debatable as to whether this counts.
In the P.O.V. Sequel, Timon was still wearing the outfit when he reunites with his Ma and Uncle Max, and they don't comment on it until after Timon has left the scene.
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 The Lion King (1994)
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Wholesome Crossdresser / int_8f8df73b
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Wholesome Crossdresser
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In The Many Horrors Of Being A Tokyo Waitress most of the characters work as crossdressing waitresses at a gay bar. It is just a job, and they get used to it. Jonas, the main character goes home wearing the costume to save time.
 Wholesome Crossdresser / int_91bb268f
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 The Many Horrors Of Being A Tokyo Waitress
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Wholesome Crossdresser / int_91bb268f
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Wholesome Crossdresser
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In The Goblin Emperor, there is Kiru, who presumably continues to wear more practical men's clothes after the attempt to deceive her potential employer about her sex failed and she got the job regardless.
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1.0
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 The Goblin Emperor
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Wholesome Crossdresser / int_9264f35d
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Wholesome Crossdresser
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SheZow is a Legacy Hero superheroine whose powers and costume are granted to whoever wears her ring. Originally meant for women in the family line, the latest person to wear the ring is Guy Hamdon, a pre-teenage boy who inadvertently got stuck with it. As a result, he wears SheZow's female-intended costume as he fights crime. Guy doesn't take it well at first but quickly becomes indifferent to it.
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1.0
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 SheZow
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Wholesome Crossdresser / int_928b5dfe
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Wholesome Crossdresser
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Another example would be Teddie in his human form, who can pull off cosplaying Alice. The other boys in the cross-dressing pageant could count too, but the student body has rather negative opinions about it.
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1.0
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 AliceInWonderland
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Wholesome Crossdresser / int_93e8b35e
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Wholesome Crossdresser
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Used as a one-off gag in Game×Rush, where the middle-class Memori is portrayed as a "Cinderella" as opposed 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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1.0
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 Game×Rush (Manga)
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Wholesome Crossdresser / int_93f8052
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Wholesome Crossdresser
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All Grown Up! has Phil dressed as his twin sister Lil. He seems to develop a crush on another boy.
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1.0
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 All Grown Up!
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Wholesome Crossdresser / int_946f58c1
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Wholesome Crossdresser
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Mahou Sensei Negima!:
The series combines this with Instant Cosplay Surprise, with the girls dressing Negi up as a surprisingly cute fox girl. It sure gave Ayaka a massive nosebleed.
Negima?! Neo has Cheerleader Negi in chapter 19. As seen here, he's not the only one in drag (hint: the other one's wearing bandages around her chest).◊
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 Mahou Sensei Negima! (Manga)
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Wholesome Crossdresser / int_95e58696
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Wholesome Crossdresser
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In Akiba's Trip: Undead & Undressed, after a sidequest where the male main character goes Disguised in Drag, you can choose to have him wear girls' clothing from that point onward.
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1.0
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 Akiba's Trip: Undead & Undressed (Video Game)
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Wholesome Crossdresser / int_96308290
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Wholesome Crossdresser
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Revolutionary Girl Utena's Utena Tenjou is a girl-dressed-as-a-boy example. Her choice of attire doesn't really do anything to hide her femininity, though, being more a matter of preference due to her desire of one day becoming a Prince Charming.
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 Revolutionary Girl Utena
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Wholesome Crossdresser / int_967347ea
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Wholesome Crossdresser
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Ouran High School Host Club:
Ouran subverts this fairly well. Haruhi is mistaken for a male by the host club at first due to her grubby and vaguely masculine clothing. However, Haruhi never bothers to correct them until they find out and doesn't have any problems with people mistaking her for a male. She simply has a wide concept of gender and doesn't mind dressing in a variety of costumes of both genders.
Her father Ryouji (aka Ranka) is a slightly more traditional Wholesome Crossdresser, who works at an okama bar. At one point he violently shoots down Tamaki's idea that the club crossdress to get into Lobelia School, since 'amateur cross-dressing' is an insult to the profession.
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 Ouran High School Host Club (Manga)
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Wholesome Crossdresser / int_9688ee61
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Wholesome Crossdresser
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Drew Carey's brother on The Drew Carey Show, before marrying Mimi.
 Wholesome Crossdresser / int_974f7efb
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1.0
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 The Drew Carey Show
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Wholesome Crossdresser / int_974f7efb
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Wholesome Crossdresser
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Sappho: Sappho dresses as a man in Greece multiple times, and is presented positively overall. Characters who know about this disapprove or react with mixed feelings however.
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1.0
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 Sappho
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Wholesome Crossdresser / int_9899aa4f
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Wholesome Crossdresser
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In Ike Ike! Nekketsu Hockey Bu, the Nekketsu Hockey Team can wear the uniforms of defeated rivals. Among them are an all-girl school team who wear white blouses and red plaid skirts.
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 Kunio-kun (Video Game)
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Wholesome Crossdresser / int_98be588d
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Wholesome Crossdresser
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The title character in Mulan is disguised as a male in order to replace her sickly father during a war.
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1.0
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 Mulan
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Wholesome Crossdresser / int_9910cc85
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Wholesome Crossdresser
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W Juliet has Makoto Narita, the male lead, who dresses as a woman because he made a deal with his father that if he spent the last two years of high school as a girl, he could pursue his dream of becoming an actor instead of inheriting his family's dojo. Also, his friend and later lover Ito Miura might count, but she's more of a Bifauxnen (she never tries to keep her gender a secret, and she occasionally complains about almost always being cast as a guy in the drama club's plays).
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Wholesome Crossdresser / int_991637c2
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Wholesome Crossdresser
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The title character of Rango wears a dress in order to pass as a travelling actor to get some arrest-ees to let their guard down. It turns into an elaborate wagon chase scene, with him still in the dress.
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 Rango
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Wholesome Crossdresser / int_994e32db
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Wholesome Crossdresser
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Tacoma from Demo Reel played Oprah for a parody and dressed as Belle from Beauty and the Beast to make Rebecca happy. He didn't mind either costume.
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1.0
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 Demo Reel (Web Video)
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Wholesome Crossdresser / int_99beaff4
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Wholesome Crossdresser
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Gene from Bob's Burgers. Only so far has actually done this once, when the Belcher kids ran a casino out of the titular restaurant's basement, but he makes references to this every so often.
The transvestite hookers from "Sheesh! Cab, Bob?", despite their occupation, are another example of this trope. They're some of the most consistently kind and cheerful characters around. How wholesome are they? One of them is even voiced by Jack McBrayer (best known for playing Kenneth Parcell), playing very much to type.
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 Bob's Burgers
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Wholesome Crossdresser / int_9a0cb5f4
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Wholesome Crossdresser
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Randoh/Yuna from Pretty Face. Justified/handwaved in that he was surgically rebuilt from a disfigured near-corpse to look like a teenaged girl.
 Wholesome Crossdresser / int_9a1c99bf
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 Pretty Face (Manga)
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Wholesome Crossdresser / int_9a1c99bf
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Wholesome Crossdresser
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Subaru Shiratori of Nanashi no Asterism is a boy who periodically cross-dresses. He typically borrows his twin sister's clothes to do so.
 Wholesome Crossdresser / int_9ba373f7
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1.0
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 Nanashi no Asterism (Manga)
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Wholesome Crossdresser / int_9ba373f7
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Wholesome Crossdresser
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Sir Ystin, the Shining Knight from Seven Soldiers (and yet another Morrison creation) is a girl disguised as a boy. The New 52 version seen in Demon Knights is a different matter...
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1.0
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 Seven Soldiers (Comic Book)
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Wholesome Crossdresser / int_9d255c2
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Wholesome Crossdresser
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A Song of Ice and Fire: Men who want to become Moonsingers must dress and live as women. In many cases, it's said outsiders cannot tell if the moonsinger is a man or woman at all due to this.
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 A Song of Ice and Fire
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Wholesome Crossdresser / int_9d47a2a2
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Wholesome Crossdresser
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Ayase from Okane ga Nai is already mistaken for a girl when he dresses normally, in the manga he dresses up as a girl at one point thus becoming virtually impossible to be identified as male. In his case it might not be all that surprising that this earns him a severe stalker who is not bothered to learn his real gender and proceeds to stalk him anyway.
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 Okane ga Nai (Manga)
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Wholesome Crossdresser
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The lovely Ms. Fate lives in the Nightside, and is a genuine old-school superheroine who happens to be played by a man.
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1.0
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 Nightside
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Wholesome Crossdresser / int_9ecd1e02
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Wholesome Crossdresser
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Pokémon:
In Pokémon Crystal, if you choose the female trainer, the overworld sprite changes from female to male if you do any game link cabling with any of the other six games. Yes, even with another Crystal version.
Everyone in Gym Leader Janine's gym in (Heart)Gold and (Soul)Silver is disguised as the Gym Leader to throw you off. Even the one guy, who gets defensive about it when the player fights him.
One of the Ferris Wheel date options for the male player character in Pokémon Black 2 and White 2 is a schoolteacher who, in the Japanese version only, takes off his shirt in the heat, and admits that he had to pass as a woman to get the job.
The Pokémon Kirlia and Gardevoir can both be male despite appearing to wear a tutu and a ballroom gown, respectively. Gen IV introduced Gardevoir's Distaff Counterpart, Gallade. Even in Gen IV and beyond, it's still perfectly possible to have a male Gardevior, since Gallade uses a different evolution method. Wally's Gardevoir in Pokémon Ruby and Sapphire is male, though the remakes replace him with a Gallade.
Gothitelle looks as though it's wearing a dress with bows, but has a 25% chance of being male. Really, a lot of the more humanoid ones qualify.
Copycat from Kanto is a girl who loves mimicking others. According to official art, this includes dressing up as them (whether they're male or female).
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The Magypsies in Mother 3, and, to a lesser extent, the girl they raised, Kumatora. Noticeably, the only Magypsy who doesn't crossdress is a traitor.
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In But I'm a Cat Person, Bianca is a bisexual woman who cross-dresses.
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 But I'm a Cat Person (Webcomic)
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Levin from Tekkaman Blade.
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Maji de Watashi ni Koi Shinasai! has Moro who occasionally has had to suffer the indignity of crossdressing for some greater cause. Some members of the family would rather him do it more often.
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Code Geass 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 Visual Novel game, Lost Colors, has the Player Character, Rai, having an Imagine Spot of Lelouch wearing a wedding dress and boy, he still looks pretty.
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Fate/Grand Order:
Astolfo is a male who wears a dress. It amuses the others and he finds the outfit cute, so he doesn't mind wearing it.
Most of the Gender Flip characters are indicated to have passed for male during their lifetimes, due to politics precluding women in positions of power or in the military.
Saber Nero mentions that she sometimes dresses as a man for fun as well as for her job, but she never does so on-screen.
Le Chevalier d'Eon is portrayed as gender-neutral and androgynous in this game but is forced to disguise themself with a maid's dress on one of the story missions.
Another story mission requires you to infiltrate a party to locate a target, so your character goes disguised as someone of the opposite gender.
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Kotarou from Denpa Kyoshi is so feminine that he was banned from wearing the male uniform.
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Deuteronomy 22:5 exact meaning is debatable, though it is sometimes taken to defy this trope.
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 The Bible
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Disney's Swiss Family Robinson had Roberta, who was disguised as a cabin boy by her father to protect her from the pirates.
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Final Fantasy:
Faris from Final Fantasy V. One character even mocks her by saying, "We will fight like men! And women! And women who dress like men!" It doesn't help that she's probably the most masculine-acting of all of the player characters. The main character even mistakes her for a man.
In Final Fantasy VII, hero Cloud Strife has to rely on the help of some friendly transvestites so that he can disguise himself as a woman and infiltrate a gangster's mansion.
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Examples from The Fairly OddParents:
One episode has Chester dressing up as a girl so he can get a skating partner.
On the opposite side Trixie was a very convincing boy in The Boy Who Would Be Queen.
In part 3 of Wishology, Timmy's dad has been known to wear a dress with a blonde wig. However, this was All Just a Dream in the Darkness' Lotus-Eater Machine.
In the episode "Scary Godparents", Timmy's parents go out as each other for Halloween.
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In Aria the Scarlet Ammo, this is Kinji's brother's method to activate Hysteria Mode (which is triggered by sexual arousal). The result is so convincing that Aria thinks Kana is Kinji's ex-girlfriend. And it actually seems to create a Split Personality. You can't get more "wholesome" than that.
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Roger DeBris from The Producers.
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Oscar from The Rose of Versailles is another example of the girl-raised-as-a-boy plot device.
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In CLANNAD ~After Story~, Misae's friends had a bit of fun sneaking Shima-kun into their school wearing a girl uniform, ending up with someone that made them jealous for being so pretty while watching him turn the heads of every male they passed.
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Magical Transvestite Cherry from Footloose, described on the cast page as "the only Magical Girl with a shred of humanity."
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 Footloose
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Charlie Watkins, a CONTROL agent on Get Smart, is such an exceptional undercover agent that he looks exactly like the Real Life (and 100% female) actress Angelique Pettyjohn, and is known as Agent 38 on account of his impressive bust measurements. Charlie's all man, though, and evidently quite heterosexual, as demonstrated by his flirting with Agent 99.
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Izumo Kunisaki from, well, Kunisaki Izumo no Jijou, who is already attractive enough to be mistaken as a girl all the time, frequently cross-dresses as a result of him invariably receiving female roles from his family's kabuki troupe, much to his chagrin. His senior in the troupe, Kagato, is another one, although unlike Izumo he actually enjoys it.
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Stardust: Captain Shakespeare is revealed to like dressing in women's clothing right at the same time he's shown as not really being a bloodthirsty murderer, but a good, kind man.
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Ryouta Kawara tends to show up in girls' outfits at various points in Hatoful Boyfriend. It's played mostly for laughs since he's a pigeon. He's also the heroine's childhood friend and considering the good ending of the "Bad Boys Love" route, he's probably her canon love interest.
If you follow Ryouta's path in the full version, he has a job at a transvestite cafe so he can support his ailing mother.
Of course, for the school festival, the heroine's class decides to be a maid cafe, so everybirdie in class dresses up as maids— you only see the others in the full version, though.
In Holiday Star he proves to crossdress for many of his jobs, and Hiyoko notices he seems cooler and more confident dressed as a Magical Girl, but he sees no significance in it. Birds don't wear clothing much - to him, skirts are basically like an apron or any other uniform.
During a drama CD Ryouta and Sakuya encounter the upperclassman Yuuya in a maid outfit, waiting in disguise - and partly it might be to shock the easily shockable Sakuya, but Yuuya greatly enjoys wearing a dress. Official art of Yuuya in drag always has him much more gleeful about it than Ryouta.
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In The Amazing World of Gumball episode "The Lady," it's revealed that Richard, unable to make any guy friends, regularly disguises himself as a woman named Samantha so he can hang out with a group of sassy older ladies. At first, Gumball and Darwin are not amused, as they believe Richard is cheating on their mother with Samantha, but once they realize the truth, they immediately try to stop Richard from breaking off his friendship with the ladies. Turns out two of the other ladies are actually men too.
"The Dress" features none of Gumball's clothes being clean, so he has to wear his mother's wedding gown to school. This ends up working well with him, as everyone treats him nicer. Unfortunately, Darwin falls in love with him.
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Hamaji in H₂O: Footprints in the Sand, who ends up marrying his best (female) friend, fathers a child, and still dresses like a girl.
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The original premise of 80s sitcom Bosom Buddies was Disguised in Drag, but the boys carry on with the charade over the course of the series longer than seems strictly necessary.
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In the Paradox Trilogy, Basil is the alien equivalent of a crossdresser, dyeing his feathers to have the brown coloration of an aeon female rather than the gaudy colors of an aeon male. Not being familiar with aeon biology, Devi doesn't realize there's anything unusual about his coloration until he explains.
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Par for the course in any story on Literotica that's in the Transsexuals/Crossdressers section and doesn't contain either magic or bondage.
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South Park: The Stick of Truth:
The game has Princess Kenny, who all the other kids present as "the fairest maiden in all the land", and who summons unicorns and wields heart-shaped arrows. She's also just a 10-year old boy in a LARPing dress and a bad wig. She holds up the "wholesome" by fighting at the New Kid's side until her Face–Heel Turn, when she becomes the Final Boss.
The New Kid can also end up crossdressing after a makeover from the Girls. There's a secret achievement for wearing the get-up while fighting Princess Kenny. Possibly subverted if the New Kid establishes themselves as female in the sequel.
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JoJo's Bizarre Adventure:
Subverted in one chapter of Battle Tendency, where Joseph cross-dresses as a tequila girl for a disguise to fool the Nazis. He fails to realize that most women aren't quite as well-built as he is. Hilarity Ensues.
In a slightly more feminine example, Narciso Anasui from Stone Ocean is a very effeminate-looking crossdresser, although the "Wholesome" part is highly up for debate here. While he is one of the good guys and seems to be genuinely in love (although his courtship methods are...strange, to say the least) with the main character, Jolyne, he is also an insane killer who has an obsession with taking objects and people (including his old girlfriend and the man she was caught cheating with) apart. He may even fall under Creepy Crossdresser, depending on who you ask.
Over time, his appearance becomes much less feminine as well, with him pretty much being fully masculinized by the end of Stone Ocean (other than the women's clothes, of course).
In JoJolion, it is tradition for the firstborn sons of the Higashikata family to cross-dress until they are 12. This is done as a way to ward off a curse that turns all firstborn sons of the family to stone. The current child doing this, Tsurugi, doesn't seem to mind.
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In a BBC modern-dress production of The Taming of the Shrew, Petruchio was a rare Western media example of a heterosexual crossdresser.
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According to L: change the WorLd, L did this for an entire year at one point, as part of an investigation.
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In season 2 of Infinity Train, Jesse and Alan Dracula (or at least the guy in his mouth) put on dresses for a fashion show themed car. It's probably the one of the few Western shows along with Steven Universe that doesn't present this as embarrassing or odd (in fact a lot of the edits on here seem to do so). The only part that can be considered funny is that Jesse has to wear the dress over his regular clothes.
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In the Canadian Disney Show My Babysitter's a Vampire Season 1 Episode 2, entitled "Three Cheers for Evil" the shows main characters Benny and Ethan must dress up as Cheerleaders 'Betty' and 'Veronica' in order to keep an eye on members of the squad they suspect are up to no good. They use the opportunity to try and get into the girls' locker room, are part of an all-girl sleepover and pillow fight, and are hit on by one of the supporting male characters while in disguise.
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Xianming Lin of Hakata Tonkotsu Ramens is a cross-dressing assassin who is initially sent out to kill the main character, but ends up working for him instead. He initially cross-dresses as part of a disguise during operations, but eventually does so even outside work as he feels it helps him maintain a connection with his long-lost sister.
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Ilulu from Miss Kobayashi's Dragon Maid wears a men's outfit when at work due to the fact that there aren't any women's clothes that would fit her proportions. This comes up again in a chapter of Kanna's Daily Life when she tries on some school uniforms and finds the Sailor Fuku too constricting, while the boy's uniforms fit just fine.
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Kitten from Breakfast on Pluto basically personifies "cute".
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Crowley from Good Omens (2019) is a bit of a Zig-Zagged example. True he's a demon posing as The Antichrist's nanny in order to have an bad influence over him, but this is all in an agreement with the angel Aziraphale in an attempt to stop Armageddon. While Aziraphale states he can't interfere with God's Ineffable Plan, Crowley argues it's still his duty to prevent any evil caused by demons. It's all for naught though; a baby mix-up at the hospital means they've been watching over the wrong child the past 11 years.
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This is a common occurrence in Super Sentai series:
In an episode of Dai Sentai Goggle Five that featured dolls coming to life, Miki/Goggle Pink disguises herself first as a male clown with a painted mask and just a slight change in voice, and later successfully pulls off a handsome prince disguise via a wig and a fitting outfit.
Then, in Choujin Sentai Jetman, the one cross-dressing was... Raita/Yellow Owl, in order to trick a Monster of the Week who absorbs women's voices. He successfully pulls it off, too - apparently, even fatties can make convincing women with just some makeup, a wig, and a kimono.
Soutarou Ushirogame/GaoBlack in Hyakujuu Sentai Gaoranger also pulled off cross-dressing as a bride. Even if he ended up striking the sumo pose and "Dosukoi!" yell.
Tetsu/DekaBreak in Tokusou Sentai Dekaranger seems inordinately fond of dressing up as a woman during undercover missions. Both times he's done it, he's caught the eye of a creepy buglike minor criminal stalker...who didn't care that it was a trap when Tetsu revealed his true gender.
In Magiranger vs. Dekaranger, he and Hikaru have to cross-dress again, much to the shock of Urara. Jasmine, however, is not surprised.
A more realistic approach is later revisited in Samurai Sentai Shinkenger, with Ryuunosuke/Shinken Blue. After all, he's a kabuki actor, thus cross-dressing is par on the course. It's even used in a plan, and it helps that the actor (Hiroki Aiba) is a Bishōnen by default. Ryuunosuke even said "he still has much to learn" after THAT much of a convincing act.
Then, the V-Cinema DVD Special took this to ridiculously funny levels, when in a bizarre (long story) moment, Kotoha and Mako dress and act like schoolboys... and then Ryuunosuke, Chiaki and Genta reveal that they're cross-dressers as well. The biggest WTF moment was when Takeru, who's calmly sitting... suddenly flips his clothes and reveal himself to be a rather CONVINCING cross dresser too. What. The. Hell.
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In Fairy Tail, after the Council orders the arrest of Erza (after the incident involving Lullaby and the sheer amount of collateral damage it caused), Natsu decides to break into the trial dressed as her and admitting guilt, so as to get her off the hook. Needless to say, the real Erza is mortified. In the end, it was just a mock trial so that the Council could assert their authority. They were going to let Erza off anyway, but thanks to Natsu, both wound up getting really arrested.
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Barracuda: Emilio, now Emilia, is a servant on the Spanish ship carrying Dona del Scuebo and Maria. He cultivates a troubled identity. Dressed as a young girl, he is sold as a slave to Mr. Flynn, who teaches him how to handle weapons and then becomes her lover. Emilia learns that he is being chased by a villain named Morkam. Morkam having killed Flynn, Emilio inherits from his mentor and decides to avenge him.
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Saber aka King Arthur from Fate/stay night. And in the Prequel Fate/Zero she dresses in a business suit that looks very good on her.
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 Fate/stay night (Visual Novel)
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Green Gable from Spinnerette is the first male to inherit the costume. He hasn't bothered to change it in any way...such as by replacing the skirt with something a little manlier or getting rid of the pigtails. Maybe he believes Real Men Wear Pink, maybe he wants to stick to tradition, or maybe he's just not all that bright.
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 Anne of Green Gables
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Buster Bunny, usually for the same reason as Bugs, to trick people.
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 Tiny Toon Adventures
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Animal Crossing examples:
You can wear any clothing or accessory items, even those that are obviously intended for the opposite sex. This extends in subsequent games to even unlocking the ability to have girl's hairstyles or shoes on a boy or vice versa. The only thing you can't do is change the face style or actually use the opposite sex clothes model (that is, putting a dress on a boy character will make it still look like a shirt, and putting a shirt on a girl will still look like a dress)- though, this last restriction is removed in the 3DS version, which has skirts, pants, and dresses as separate kinds of items. While it does specifically classify clothes as masculine, feminine, or unisex, it doesn't stop you from buying them or trying them on in the store- the Able sisters comment on it but are okay with it. Male characters will even do a Girly Run if they're wearing a skirt or dress.
Blanca, the cat with the blank face, is evidently a male, even though "Blanca" is the feminine form, the gibber-clip is the highest-pitched one used for females, and the outfit is the female skirt. She has no name in Japan, and internationally she's been changed into a girl.
Gracie the giraffe fashion designer, who wears fishnet-patterned, high-heeled boots, is a guy in the Japanese versions. Saharah, the camel who sells wallpaper and carpets, is as well, though she only wears a vest and her only feminine feature is long eyelashes, so she doesn't count as this.
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The Howling Banshees, an Eldar warrior Path in Warhammer 40,000 are traditionally an all female squad. Males, however, are permitted to join their ranks. Since the Banshee is a female spirit in Eldar mythology, he adopts a female persona and female armor when wearing his 'Warmask'.
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Parodied in El Goonish Shive when avowed pervert (and frequent Gender Bender) Tedd is teased about trading school uniforms with Susan he vehemently protests that "I don't crossdress in women's clothing!" Susan muses that technically this is true. He crosses dresses in men's clothing quite frequently but never wears women's clothing while male (with two non-canon exceptions) and always changes out of any women's clothing he has on before reverting to male.
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The New Kid can also end up crossdressing after a makeover from the Girls. There's a secret achievement for wearing the get-up while fighting Princess Kenny. Possibly subverted if the New Kid establishes themselves as female in the sequel.
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 South Park: The Fractured but Whole (Video Game)
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Pokémon:
Ash has to dress as "Ashley" to get his Gym battle with Erika. Brock is fooled, but Pikachu isn't (scent, maybe?). Ash would go on to invoke once a saga (minus Johto), once as a Meido.
Later in Unova he need to set straight some snobby b’s that bad-mouthed his Snivy from a female-only circus. Cue Ashley.
The tradition was (briefly) broken in XY when it was Serena who disguised herself as Ash while he was sick. Many fans felt robbed by this. Fortunately, the next season made up for it...
In Alola when he and his classmates are taking over from a sick Joy, the guys failed to find the male uniform at first. Ash was pondering at getting away with the female uniform, but that sparked interest in the girls. With a dash of makeup and Rotom’s blond wig, we get our cutest Ashley ever.
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). One of James' disguises involves him wearing fake breasts for a beauty contest, which got an episode of the series banned. Jessie also used to crossdress a lot as well.
A few canonically male Pokemon have been shown in female clothing. Some of them are embarrassed but some, like Dawn's Piplup (who frequently cheered in a pink cheerleader outfit, though he also had a male kimono), aren't phased. An Unova episode even has Pikachu Disguised in Drag by taping a heart-shape onto his tail.
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Princess Jellyfish features Kuranosuke, the main male lead of the series. He likes to dress up in women's clothing for the sake of it. Since the residents aren't fond of men, dressing up as a woman is his only way to keep visiting Tsukimi, whom he seems to be developing feelings for.
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Celadon's New Blossom:
The plot of the fic revolves around Ash becoming Erika's student. To go along with this, he must pretend to be a girl until he defeats the Pokémon League. Ash is initially embarrassed and annoyed by this, but he admits that he's rather cute as a girl and the clothes aren't too bad.
It's implied that James' interest in cross-dressing extends beyond just doing it for disguise purposes.
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Clarence from Boston Legal crossdressed as both an alter ego, Clarice, and Oprah.
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 Boston Legal
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Several episodes of 6teen have Jude cross-dressing for various reasons, such as trying to get in touch with his feminine side, a disguise so he can get more doughnuts by donating more blood than is healthy, and trying to get into a dance where only single girls can get in. This is even highlighted in one episode:
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Astro Boy examples:
Astro disguised himself as his sister Uran in "The Greatest Robot in the World" (Tetsuwan Atom, 1963), which likely makes him anime's first crossdresser.
In the original manga story and the 1980s anime, Uran disguised herself as Atom/Astro so she could fight Pluto in his place.
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Shizu in Maria†Holic. Of course, she only crossdresses when attending classes (she and her brother are in a competition with each other, and part of the competition involves attending both a boys' school and a girls' school during their high school years).
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Faris from Final Fantasy V. One character even mocks her by saying, "We will fight like men! And women! And women who dress like men!" It doesn't help that she's probably the most masculine-acting of all of the player characters. The main character even mistakes her for a man.
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At one point in the third chapter of The Melancholy of Haruki Suzumiya, Haruki has Mitsuru wear a maid outfit for a photo shoot.
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Kate/Bob in Blackadder II and Goes Forth is a Sweet Polly Oliver, but admits she "actually prefer[s] wearing boys' clothes" (to the confusion of Lord Flashheart, who's always more comfy in a dress). She's also the most wholesome character in the entire series, bordering on Incorruptible Pure Pureness. Flashheart himself could count as an example, too. He’s not exactly wholesome, per se, but he is still Rated M for Manly despite his cross-dressing.
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One of the outfit options for Mario in Super Mario Odyssey is a replica of Peach's wedding dress and veil, tailored to his measurements and complete with earrings and heels. Bowser thinks he looks amazing in it. Not that it matters since he wasn't invited to the wedding. As for Luigi, he doesn't think it's weird that his brother's wearing a dress, just that he's wearing a wedding dress for fun.
Later, a dress based on Hariet the Broodal's was released, complete with stockings and heels. Again, Bowser thinks he looks amazing, while Luigi just thinks it looks familiar.
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Song at Dawn 'Lady' Sanchez is a man pretending to be a lady. Dragonetz notes that the signs are there but no one would notice unless they were looking for them.
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In There, Beyond the Beyond, Futaba admits that wearing girly clothes doesn't bother him, because his older sister makes him do it all the time.
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Yozak from Kyo Kara Maoh! is a 'spy' who, though taller and more muscular than his fellow bishounen, loves to disguise himself as a woman. A cheerfully flirtatious woman, even. He even carries a dress around, just in case he needs it.
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Tootsie. While Dustin Hoffman starts out playing a woman simply in order to get work, he ends up playing the part in real-life as well.
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 Tootsie
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On Jimmy Two-Shoes, both Jimmy and Lucius do this while being flight attendants.
Jimmy ends up cross-dressing frequently during the series, whether it's for disguise purposes, losing a bet or because he felt like it.
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Monty Python's Flying Circus:
All the Pythons have done this at one point, especially Terry Jones, who was very good at it. After all, dragging up is a rite of passage and an essential skill expected of any British male comedian. It's a rare big-name comic or comic actor who hasn't done this once in their career.
Also part of The Lumberjack Song lyrics, where the Lumberjack puts on women's clothing, hangs around in bars, wears high heels, suspendies, and a bra, wishing he was a girlie just like his dear papa. When the mounties recite the lines as chorus, they eventually get disgusted and leave.
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Daphnis in Tears to Tiara 2 crossdresses so he can follow Elissa everywhere as her bodyguard. He fools everyone at first sight and makes the goddess of war and barbarian princess complain about how to be ladylike.
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Spoony as Spoonette and The Gate Cleaner's Wife, Linkara as 80s Chick, Benzaie as Veronique and The Nostalgia Critic as an Airline Hostess.
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Hime, from Himegoto, is forced to dress as a girl during school. In the spinoff Himegoto+, everyone in the main cast cross-dresses.
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Milla from Tales of Xillia can wear the costumes of Stahn and Dhaos. She also has access to Asbel's costume in Tales of Xillia 2
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 Tales of Xillia (Video Game)
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Carl from Johnny Bravo has dressed as a woman many times throughout the series course.
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En Shinohara from Usotsuki Lily has such a strong dislike for men that he can't even look at his own reflection. It's for this same reason that he takes up crossdressing. Hilarity Ensues as the series is about he and his new girlfriend trying to work around the issues this causes.
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EastEnders also introduced one in the form of Les Coker, who enjoys dragging up as "Christine". Deconstructed as it's treated as a Dark Secret by his wife Pam, and when it gets out, several residents (most notably Billy Mitchell) turn against him. A major part of their story arc was Pam learning to accept Christine, which she eventually did.
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In the Mai-Otome manga, Princess Mashiro is replaced by her twin brother. The gags of the manga constantly poke fun at "Manshiro's" plight.
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Accused: Simon, in his guise as Tracie. This even gets him acquitted, as he goes into court dressed as Tracie and successfully shows how ridiculous the idea of committing a crime in that outfit would be.
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Makoto/"Mako-chan" in Minami-ke. All it seems to take is a hair clip and a skirt and bam! Uncannily cute & convincing girl. Like, "make you doubt your own preference" convincing. Interestingly, his first comment in the second season is being glad he can dress normally again... only for Kana to take one look at Normal!Makoto and shut the door in his face. Cut to him in a girl's outfit, with the comment the girls can't accept him otherwise.
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Souta from WORKING!! was this when he was little (he's the only son in the family and was raised like a girl), and then needed to do it again in ep 9 and 13.
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Yuki Nomura from the manga No Bra is a sweet, kind, beautiful and roommate Masato Kataoka's perfect girl. Except she's a he.
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Maurice and his fellow Drag Queens in Last Vegas initially come off as a joke about accidentally hitting on creepy crossdressers, but Sam quickly befriends them and Maurice later shows up at the party in normal business attire with his wife.
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Fruits Basket features several wholesome crossdressers:
Among the men of the Sohma family: Ritsu always wears women's clothing out of insecurity and Ayame is an equal-opportunity sort who runs a fetish costume shop. Momiji is more of a downplayed example, since his casual outfits tend to skew feminine but he always wears shorts instead of skirts or dresses.
Subverted in the case of Akito: shortly after we learn they are a Creepy Crossdresser, they turn into the wholesome variety (eventually they stop and accept themselves as their original gender).
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In the Insecticomics, the Insecticons are fond of donning Barbie dresses and actually look quite good in them. It's hilarious. "Does this dress make me look fat, fat?"
Though they are Decepticons so maybe not quite so wholesome, then again they're usually too lazy to be evil and usually come off as Chaotic Neutral.
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Soutarou Ushirogame/GaoBlack in Hyakujuu Sentai Gaoranger also pulled off cross-dressing as a bride. Even if he ended up striking the sumo pose and "Dosukoi!" yell.
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Aikawa of Prunus Girl is very convincing, but helpfully reminds everyone at least once a chapter that he's a guy in between teasing Maki and hinting at Recursive Crossdressing.
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A more realistic approach is later revisited in Samurai Sentai Shinkenger, with Ryuunosuke/Shinken Blue. After all, he's a kabuki actor, thus cross-dressing is par on the course. It's even used in a plan, and it helps that the actor (Hiroki Aiba) is a Bishōnen by default. Ryuunosuke even said "he still has much to learn" after THAT much of a convincing act.
Then, the V-Cinema DVD Special took this to ridiculously funny levels, when in a bizarre (long story) moment, Kotoha and Mako dress and act like schoolboys... and then Ryuunosuke, Chiaki and Genta reveal that they're cross-dressers as well. The biggest WTF moment was when Takeru, who's calmly sitting... suddenly flips his clothes and reveal himself to be a rather CONVINCING cross dresser too. What. The. Hell.
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In Moon Crest 24, this trope is played with when Derek dresses in Lucy's clothes after his first shower in months. Since Lucy threw out his old clothes in order to keep people from associating him to the Ice Titan's attack, she decided that it was a good idea to lend him her t-shirt and pants. Just until they go to Cool Topic to get him actual (emo) boy clothes.
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In both the film and the play of Victor/Victoria, the lead is a woman who crossdresses as a male, then gets a job as a female impersonator in a burlesque show. Also an example of Recursive Crossdressing.
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Michael Jeter in The Fisher King could be the Trope Codifier.
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Wandering Son has Chizuru, a middle school girl who likes blurring rules and gender roles due to commonly wearing the boys uniform to school. She goes to an all-girls high school and it's unknown if she drops the habit. Chizuru strictly crossdresses at school as she's never shown wearing anything too androgynous outside of it.
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Monthly Girls' Nozaki-kun: Tsubaki has an overall positive/light-hearted approach to characters wearing clothes typically worn by the opposite sex, as part of her gender-role-defying ways.
There's often official manga art of the male characters wearing dresses/skirts which are all done for fun rather than mockery: for example, the Nozaki brothers and Mikoshiba are in frilly dresses as a tarot card (with only Mikoshiba looking confused), and Nozaki happily wears a similarly frilly dress on the Chapter 87 cover.
Nozaki willingly tries on the sailor uniform for manga purposes when Sakura refuses to model it for him, and even gets upset because his muscles stop it from fitting him properly. He also considers wearing a custom-made sailor uniform for a fansign to portray his image as a female shoujo manga author.
Kashima encourages Hori to pursue his (nonexistent) "princess" dreams by giving him girls clothes to wear. He doesn't quite appreciate her "kindness" (but is still impressed by the outfit coordination). Tsubaki implies in the fanbook Hori would eagerly play the princess opposite Kashima in order to keep her and would go as far as to wear a corset to look the part. And when Rei asks him if he looks good in ladies' clothing (to see if he complements her Bifauxnen sister), he seriously considers the idea before stopping himself.
Bifauxnen Kashima herself, of course, happily wears her "bookish male student" fashion when she's not in her prince costume or waiter uniform (or the two times she got away with wearing the school pants).
Sakura's brother Towa seems to think Kashima in her normal girls' school uniform itself is her crossdressing. He mistakes her for the "model" Nozaki and concludes "he" wears the skirt because it's the trend, which Towa finds cool. He finds out she isn't Nozaki but not that she's a girl.
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Butterflies, Flowers: Domoto's coworker and very close friend Suou, of whom Choko is quite jealous until she realizes he's a he.
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In The Walker Papers series by C.E. Murphy, Joanne's friend Billy Holiday is a crossdresser who is also a respected police detective and happily married with children.
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British soap Hollyoaks features Kris, a bisexual cross-dressing man.
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Eiji Shigure in Gravion, while not a crossdresser by custom, ends up disguised (or at least dressed) like a woman quite a few times over the course of the series with little to no complaint. Then towards the end of the series, we find out that Sandman's Battle Butler was Eiji's missing sister the whole time, so it seems to run in the family.
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707 in Mystic Messenger has a habit of cross-dressing and pretending to go by a different name. It's never plot-relevant, but he manages to confuse some of the other RFA members by being attractive in a dress.
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Tetsu/DekaBreak in Tokusou Sentai Dekaranger seems inordinately fond of dressing up as a woman during undercover missions. Both times he's done it, he's caught the eye of a creepy buglike minor criminal stalker...who didn't care that it was a trap when Tetsu revealed his true gender.
In Magiranger vs. Dekaranger, he and Hikaru have to cross-dress again, much to the shock of Urara. Jasmine, however, is not surprised.
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Baka and Test: Summon the Beasts's Hideyoshi is one, naturally. But since he has an identical twin sister, the cast and us can let it slide. The fact that Hideyoshi's a boy, that is.
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In the Black Cat anime, both Train and Sven are shown crossdressing. For Sven, he wears a very frilly, fancy dress to try to lure a killer for a bounty. It doesn't work. For Train, after transforming into a child, while Eve and Kyoko go out to buy clothes the right size for him, he's forced to wear Eve's dress.
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Nagisa and Ryunosuke from Urusei Yatsura, a boy and girl who are forced to crossdress by their fathers and in an arranged marriage with each other, all so that Ryunosuke's family tea shop will stay in the family.
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Toadsuke from Supah Nario Bros.
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Stewie in Family Guy has taken to this lately. While the most prominent example is Season 5's "Boys Do Cry", in which he dresses as a girl to escape a witch-hunting mob and ends up entering a beauty pageant during the Griffins' stay in Texas, he also dressed up in another episode and pretended to be Brian's girlfriend to spark jealousy on another girl. Men at the restaurant recognized his female persona, so he's obviously used it at least once before.
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Lance in Nameless does this in his route in order to prevent Eri from acting in a play where she'd be kissed by Red. Sadly, it is never shown on screen.
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It would be better to list Astolfo here, given he first appeared in Fate/Apocrypha. His looking like a lady (and even playing up gender ambiguity) has been joked about even in universe! This kinda leads into an Unsettling Gender Reveal played for laughs when Jeanne ends up seeing Astolfo walk out of the shower stark naked. Bare in mind, at this point, she somehow (in spite of her True Name Discernment skill, which should have clued her in) didn't know Astolfo was a guy. Hilarity Ensues, with the end result being Jeanne letting out a very high-pitched scream and Astolfo laughing about it even on the following day, while Sieg expresses disbelief that Jeanne DIDN'T know.
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" The Crush Girls 25th Anniversary Memorial Match" at NOSAWA Bom-Ba-Ye #5 Rongai One Night Stand saw Yoshihiro Takayama and Minoru Suzuki dressed as Lioness Asuka and Chigusa Nagayo against Kikutaro and Yoshihiro Sakai dressed as Dump Matsumoto and Bull Nakano.
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Pulaski, the cross-dressing killing machine in Undead on Arrival, is one of the more heroic characters in the novel. He's the most fabulous by a large margin.
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Out of all the characters in Anpanman, tough guy Kamameshidon is the character on the heroes side that is the most likely to crossdress. When he gets a starring episode with a female character, it's very likely that he'll end up crossdressing as her. Thanks to his rice bowl head and deep voice...he is not that good at pulling it off. His friends, Tendonman and Katsudonman, have also crossdressed, just not as often as Kamameshidon does. This possibly could all be based on a single Incredibly Lame Pun, as "okama" is Japanese for a male crossdresser.
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In Queen of Wands, Felix occasionally crossdresses, and nobody makes a big deal about it.
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In Umlaut House 1 and 2 there are a few occasions where Volair and Pierce dress in drag (like father like son). Plus that one time Rick switched his prosthetic body with a female one so he could pretend to be a woman for Jake's parents. Male cheerleading captain Jack Fusselton, on the other hand, wears a woman's outfit as a form of psychological warfare (and unlike the other examples is straight).
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In the Evil Genius Trilogy Cadel crossdresses several times as a disguise, starting in his disguise class at the Axis Institute and continuing whenever he needs to escape some kind of surveillance. He has a whole alternate identity for his female persona - Ariel Schaarp.
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Highschool Romance: Shoji, the main character, is accidentally enrolled in an all-girl school, but the principal Lea decides to give him a chance at staying provided that he tries to pass as a girl, even buying him lingerie and clothes. Shoji himself, despite some initial embarassment, gets used to it, and during the course of the story he can befriend and romance two other girls. If Selene is chosen, it's revealed that Shoji took up crossdressing for his girlfriend's pleasure.
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Eyeshield 21 had Ootawara and Sakuraba dressed as maids (during a public practice) as a punishment for losing a trivia game during a school festival. This, however, only increased Sakuraba's popularity. Hiruma also dressed like a maid to spy on the players from the American team. Panther got a good laugh out of it.
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Part of Override's bio from her toy on Transformers Cybertron (only available after entering her Cyber Key code on the TFC website) states that in order to win leadership of Speed Planet she entered the race disguised as a male. Exactly how this works (or for that matter why she'd do it) isn't mentioned.
It was meant as a Mythology Gag referencing the fact that in the original Japanese, she's already male.
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George, from the otherwise hilariously backward children's series The Famous Five by Enid Blyton.
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Genshiken:
Kousaka crossdresses to help the club sell doujinshi at a comic festival. His club mates find it surprisingly convincing.
Genshiken Nidaime introduces Hato Kenjirou, who crossdresses as a way of life, and never visits the club as a boy.
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comment
Sgt. Frog: All five Keronians have crossdressed at least once, with Keroro himself as the biggest repeat offender. On the flipside, Kululu's debut episode has him turning Aki back into a 14-year-old — whereupon she dresses up in her son Fuyuki's school uniform and sneaks off to his school. Their resemblance is uncanny.
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Wholesome Crossdresser
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comment
An enemy example occurs in one episode of Yu Yu Hakusho. Yusuke and company are storming the compound of a demon-exploiting tycoon and have to have off with his guards. One of them appears to be a girl named Miyuki (and honestly looks like such), so Kuwabara backs down while Yusuke holds no such qualms. During the fight, though, a quick grope up top and down below told Yusuke he didn't need to take it easy on him, so he didn't. The only dirty looks later were directed towards Yusuke for acting like a pervert.
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On Hill Street Blues, Jeffry Tambor played a cross-dressing lawyer who was doing so on advice from his psychiatrist to "resolve his feminine-identity issues." (The "cure" worked, and the same lawyer later became a highly-respected judge on the series).
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In Catherine: Full Body, the character Rin is a kind male crossdresser who uses his powers to help the main character Vincent.
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Racine Blanche Volban in Glass Fleet assumes her brother Michel's identity after his death in battle, and passes herself off as a man thereafter. In the process she also acquires her brother's Stalker with a Crush, who is a bit put out when he discovers that "Michel" is a woman.
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Wholesome Crossdresser
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comment
Pleakley in Lilo & Stitch and Lilo & Stitch: The Series. Justified in that having three legs pretty much rules out pants as an option.
And Jumba, to an extent. In the series, he once dressed up as Pleakley's 'bride' and nearly married him.
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Kou From Samurai High School.
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Wholesome Crossdresser
 Wholesome Crossdresser / int_fe85bfc8
comment
Super Smash Bros. allows Miis to crossdress with some Mii Fighter outfits (such as dressing a male Mii as Viridi or Ashley, or a female Mii as Knuckles or Takamaru), but other outfits (such as the Inkling) automatically appear differently for each gender Mii.
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Wholesome Crossdresser
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Not one to let her middle class scholarship namesake have all the fun, Haruhi Suzumiya has her moment when she's allegedly Disguised in Drag in chapter 3 of Disappearance.
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Wholesome Crossdresser
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While Ashly Burch, from Hey Ash, Whatcha Playin'?, is pretty far from "wholesome", she does rock some mean costumes of male characters in many early episodes.
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The following is a list of statements referring to the current page from other pages.

 Wholesome Crossdresser
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Characters as Device
 Wholesome Crossdresser
processingCategory2
Small Reference Pools
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Wholesome Crossdresser
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Wholesome Crossdresser
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seeAlso
Wholesome Crossdresser
 Vivere Disce (Blog)
seeAlso
Wholesome Crossdresser
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type
Wholesome Crossdresser
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Wholesome Crossdresser
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Wholesome Crossdresser
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Wholesome Crossdresser
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Wholesome Crossdresser
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Wholesome Crossdresser
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Wholesome Crossdresser
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Wholesome Crossdresser
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Wholesome Crossdresser
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Wholesome Crossdresser
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seeAlso
Wholesome Crossdresser
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type
Wholesome Crossdresser
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type
Wholesome Crossdresser
 AdultStuck
seeAlso
Wholesome Crossdresser
 Akatsuki Kitten: Phoenix Corporation Overhaul / Fan Fic / int_28f852ea
type
Wholesome Crossdresser
 BloodBullets
seeAlso
Wholesome Crossdresser
 CureBetamax
seeAlso
Wholesome Crossdresser
 DelicatessenPrettyCure
seeAlso
Wholesome Crossdresser
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type
Wholesome Crossdresser
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seeAlso
Wholesome Crossdresser
 Futari Wa Pretty Cure Dimensions / Fan Fic
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Wholesome Crossdresser
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seeAlso
Wholesome Crossdresser
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type
Wholesome Crossdresser
 LittleMissMary
seeAlso
Wholesome Crossdresser
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type
Wholesome Crossdresser
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Wholesome Crossdresser
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Wholesome Crossdresser
 Pretty Cure Agents Of Romero / Fan Fic
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Wholesome Crossdresser
 Pretty Cure Animated / Fan Fic
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Wholesome Crossdresser
 Pretty Cure Classics / Fan Fic
seeAlso
Wholesome Crossdresser
 PrettyCureCostumeParty
seeAlso
Wholesome Crossdresser
 Pretty Cure Dimensional Evolution / Fan Fic
seeAlso
Wholesome Crossdresser
 Pretty Cure Fan Fic Features / Fan Fic
seeAlso
Wholesome Crossdresser
 Pretty Cure Four Seasons / Fan Fic
seeAlso
Wholesome Crossdresser
 Pretty Cure Magical Cards / Fan Fic
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Wholesome Crossdresser
 PrettyCureMotherNature
seeAlso
Wholesome Crossdresser
 Pretty Cure Strange Happenings / Fan Fic
seeAlso
Wholesome Crossdresser
 PrettyCureToy
seeAlso
Wholesome Crossdresser
 PrettyCureTransientCrossNEWTON
seeAlso
Wholesome Crossdresser
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type
Wholesome Crossdresser
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Wholesome Crossdresser
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Wholesome Crossdresser
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seeAlso
Wholesome Crossdresser
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type
Wholesome Crossdresser
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type
Wholesome Crossdresser
 Frozen Wight (Fanfic) / int_28f852ea
type
Wholesome Crossdresser
 Guardian Blue (Fanfic) / int_28f852ea
type
Wholesome Crossdresser
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type
Wholesome Crossdresser
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type
Wholesome Crossdresser
 Pokemon Bold Bronze And Strong Steel (Fanfic)
seeAlso
Wholesome Crossdresser
 Pretty Cure Seasons Delight (Fanfic)
seeAlso
Wholesome Crossdresser
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type
Wholesome Crossdresser
 So, What Colour Is Your Toothbrush? (Fanfic) / int_28f852ea
type
Wholesome Crossdresser
 The Adventures Of Kiko Fluffy Pants (Fanfic) / int_28f852ea
type
Wholesome Crossdresser
 The Many Quirks Of Phantom Thievery (Fanfic) / int_28f852ea
type
Wholesome Crossdresser
 Warbound Widow / Fan Fic / int_28f852ea
type
Wholesome Crossdresser
 White Sheep (Fanfic) / int_28f852ea
type
Wholesome Crossdresser
 White Sheep (RWBY) (Fanfic) / int_28f852ea
type
Wholesome Crossdresser
 Dead Men Don't Wear Plaid / int_28f852ea
type
Wholesome Crossdresser
 Deep Red / int_28f852ea
type
Wholesome Crossdresser
 Diamonds Are Forever / int_28f852ea
type
Wholesome Crossdresser
 Dragonslayer / int_28f852ea
type
Wholesome Crossdresser
 Ed Wood / int_28f852ea
type
Wholesome Crossdresser
 Flowers of War / int_28f852ea
type
Wholesome Crossdresser
 Forbidden Zone / int_28f852ea
type
Wholesome Crossdresser
 Gangs of New York / int_28f852ea
type
Wholesome Crossdresser
 Gintama / int_28f852ea
type
Wholesome Crossdresser
 I Don't Want to Be a Man / int_28f852ea
type
Wholesome Crossdresser
 Ladybugs
seeAlso
Wholesome Crossdresser
 Last Vegas / int_28f852ea
type
Wholesome Crossdresser
 Mrs. Doubtfire
seeAlso
Wholesome Crossdresser
 Mrs. Doubtfire / int_28f852ea
type
Wholesome Crossdresser
 Onmyōji / int_28f852ea
type
Wholesome Crossdresser
 Peking Opera Blues / int_28f852ea
type
Wholesome Crossdresser
 Racing Daylight / int_28f852ea
type
Wholesome Crossdresser
 Shakespeare in Love
seeAlso
Wholesome Crossdresser
 Sorority Boys / int_28f852ea
type
Wholesome Crossdresser
 The Act of Killing / int_28f852ea
type
Wholesome Crossdresser
 The Adventures of Priscilla, Queen of the Desert / int_28f852ea
type
Wholesome Crossdresser
 The Grand Illusion / int_28f852ea
type
Wholesome Crossdresser
 The Producers / int_28f852ea
type
Wholesome Crossdresser
 Tootsie / int_28f852ea
type
Wholesome Crossdresser
 Tunnelvision
seeAlso
Wholesome Crossdresser
 Super Mario Bros. (Franchise) / int_28f852ea
type
Wholesome Crossdresser
 Super Sentai (Franchise) / int_28f852ea
type
Wholesome Crossdresser
 Zatoichi (Franchise) / int_28f852ea
type
Wholesome Crossdresser
 Lucahjin (Lets Play) / int_28f852ea
type
Wholesome Crossdresser
 PewDiePie (Lets Play) / int_28f852ea
type
Wholesome Crossdresser
 Baka and Test: Summon the Beasts / int_28f852ea
type
Wholesome Crossdresser
 Haganai / int_28f852ea
type
Wholesome Crossdresser
 Is This a Zombie? / int_28f852ea
type
Wholesome Crossdresser
 MM! / int_28f852ea
type
Wholesome Crossdresser
 Mayo Chiki! / int_28f852ea
type
Wholesome Crossdresser
 Shimoneta / int_28f852ea
type
Wholesome Crossdresser
 Slayers / int_28f852ea
type
Wholesome Crossdresser
 Sukisho
seeAlso
Wholesome Crossdresser
 Zaregoto / int_28f852ea
type
Wholesome Crossdresser
 Blood Ninja
seeAlso
Wholesome Crossdresser
 Diary of a Wimpy Kid / int_28f852ea
type
Wholesome Crossdresser
 Franklin / int_28f852ea
type
Wholesome Crossdresser
 Graveyard School / int_28f852ea
type
Wholesome Crossdresser
 Les Misérables / int_28f852ea
type
Wholesome Crossdresser
 Leviathan / int_28f852ea
type
Wholesome Crossdresser
 Mahabharata / int_28f852ea
type
Wholesome Crossdresser
 Oracle of Tao / int_28f852ea
type
Wholesome Crossdresser
 Paradox Trilogy
seeAlso
Wholesome Crossdresser
 Song at Dawn
seeAlso
Wholesome Crossdresser
 The Far Pavilions / int_28f852ea
type
Wholesome Crossdresser
 The Heroic Legend of Arslan / int_28f852ea
type
Wholesome Crossdresser
 The Saga of Tuck / int_28f852ea
type
Wholesome Crossdresser
 Trainspotting / int_28f852ea
type
Wholesome Crossdresser
 Welkin Weasels / int_28f852ea
type
Wholesome Crossdresser
 Who Censored Roger Rabbit? / int_28f852ea
type
Wholesome Crossdresser
 AvantiUnAltro
seeAlso
Wholesome Crossdresser
 BloodNinja
seeAlso
Wholesome Crossdresser
 Crossdresser
seeAlso
Wholesome Crossdresser
 DivineRose125
seeAlso
Wholesome Crossdresser
 Duncan
seeAlso
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 Elianto
seeAlso
Wholesome Crossdresser
 JerkAssWoobie
seeAlso
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 KeyAndPeele
seeAlso
Wholesome Crossdresser
 LittleMissMary
seeAlso
Wholesome Crossdresser
 LoveStage
seeAlso
Wholesome Crossdresser
 Ptitle3y8dc3wk
seeAlso
Wholesome Crossdresser
 Ptitlefer89dxpeovn
seeAlso
Wholesome Crossdresser
 ROFLopadous
seeAlso
Wholesome Crossdresser
 TheBookOfStoriesOCT
seeAlso
Wholesome Crossdresser
 TheEvilDrBolty
seeAlso
Wholesome Crossdresser
 TheGleeProject
seeAlso
Wholesome Crossdresser
 TheInterferenceLegends
seeAlso
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 TortTaura
seeAlso
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 VanessaMichaelMunroe
seeAlso
Wholesome Crossdresser
 VdexProject
seeAlso
Wholesome Crossdresser
 AKB49 – Renai Kinshi Jourei (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Ai Ore! Love Me! (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Ai Shite Night (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Aitsu no Daihonmei (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Aphorism (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Arata Kangatari (Manga)
seeAlso
Wholesome Crossdresser
 Basara (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Black Jack (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Blend-S (Manga) / int_28f852ea
type
Wholesome Crossdresser
 BreakfastClub
seeAlso
Wholesome Crossdresser
 Charisma Doll (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Dead Dead Demon's Dededede Destruction (Manga) / int_28f852ea
type
Wholesome Crossdresser
 From Eroica with Love (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Fruits Basket (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Genshiken (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Genzo (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Get Backers (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Giant Robo (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Gintama (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Haikara-san ga Tooru (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Hana-Kimi (Manga)
seeAlso
Wholesome Crossdresser
 Hikaru to Hikari (Manga) / int_28f852ea
type
Wholesome Crossdresser
 His Favorite (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Hunter × Hunter (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Iketeru Futari (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Karneval (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Kase-san (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Kuragehime (Manga)
seeAlso
Wholesome Crossdresser
 Kyou Kara Ore wa!! (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Letter Bee (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Maid-Sama! (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Me & My Brothers (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Monthly Girls' Nozaki-kun (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Nisekoi (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Nozomu Nozomi (Manga) / int_28f852ea
type
Wholesome Crossdresser
 OniichanToIssho
seeAlso
Wholesome Crossdresser
 Our Dreams at Dusk (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Ouran High School Host Club (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Patalliro! (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Princess Jellyfish (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Princess Knight (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Princess Princess (Manga) / int_28f852ea
type
Wholesome Crossdresser
 RIN-NE (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Sazanami Cherry (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Sgt. Frog (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Shugo Chara! (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Strike Witches (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Sumomo Mo Momo Mo (Manga) / int_28f852ea
type
Wholesome Crossdresser
 The Electric Tale of Pikachu (Manga) / int_28f852ea
type
Wholesome Crossdresser
 The Wallflower (Manga) / int_28f852ea
type
Wholesome Crossdresser
 The World God Only Knows (Manga) / int_28f852ea
type
Wholesome Crossdresser
 The Yagyu Ninja Scrolls (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Tokyo Ghoul (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Tripeace
seeAlso
Wholesome Crossdresser
 Violinist of Hameln (Manga) / int_28f852ea
type
Wholesome Crossdresser
 WORKING!! (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Yona of the Dawn (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Dark Air (Manhwa) / int_28f852ea
type
Wholesome Crossdresser
 Deathgaze
seeAlso
Wholesome Crossdresser
 Dummy (Music)
seeAlso
Wholesome Crossdresser
 FT Island (Music) / int_28f852ea
type
Wholesome Crossdresser
 Foo Fighters (Music) / int_28f852ea
type
Wholesome Crossdresser
 Havana (2017) (Music) / int_28f852ea
type
Wholesome Crossdresser
 IZ*ONE (Music) / int_28f852ea
type
Wholesome Crossdresser
 Joel Plaskett (Music) / int_28f852ea
type
Wholesome Crossdresser
 Kiesza (Music)
seeAlso
Wholesome Crossdresser
 Kisaki (Music) / int_28f852ea
type
Wholesome Crossdresser
 Monsta X (Music) / int_28f852ea
type
Wholesome Crossdresser
 Sandy & Junior (Music) / int_28f852ea
type
Wholesome Crossdresser
 Transformer (Music) / int_28f852ea
type
Wholesome Crossdresser
 We're Only in It for the Money (Music) / int_28f852ea
type
Wholesome Crossdresser
 Young Thug (Music) / int_28f852ea
type
Wholesome Crossdresser
 The Chronicles Of Oz (Podcast) / int_28f852ea
type
Wholesome Crossdresser
 Word Funk (Podcast) / int_28f852ea
type
Wholesome Crossdresser
 Henshin Heroes (Roleplay) / int_28f852ea
type
Wholesome Crossdresser
 AKBingo! / int_28f852ea
type
Wholesome Crossdresser
 All in the Family / int_28f852ea
type
Wholesome Crossdresser
 America's Next Top Model / int_28f852ea
type
Wholesome Crossdresser
 Black Hole High / int_28f852ea
type
Wholesome Crossdresser
 Blackadder / int_28f852ea
type
Wholesome Crossdresser
 Boy Meets World / int_28f852ea
type
Wholesome Crossdresser
 Casanova
seeAlso
Wholesome Crossdresser
 Charles II: The Power and the Passion / int_28f852ea
type
Wholesome Crossdresser
 Cold Case / int_28f852ea
type
Wholesome Crossdresser
 Crime Scene / int_28f852ea
type
Wholesome Crossdresser
 Drake & Josh / int_28f852ea
type
Wholesome Crossdresser
 Engine Sentai Go-onger / int_28f852ea
type
Wholesome Crossdresser
 Escape of the Artful Dodger / int_28f852ea
type
Wholesome Crossdresser
 Family Feud / int_28f852ea
type
Wholesome Crossdresser
 Good Eats / int_28f852ea
type
Wholesome Crossdresser
 Hikonin Sentai Akibaranger / int_28f852ea
type
Wholesome Crossdresser
 Hollyoaks / int_28f852ea
type
Wholesome Crossdresser
 Horrible Histories / int_28f852ea
type
Wholesome Crossdresser
 Hou$e of Lie$ / int_28f852ea
type
Wholesome Crossdresser
 Key & Peele / int_28f852ea
type
Wholesome Crossdresser
 Knowing Brothers / int_28f852ea
type
Wholesome Crossdresser
 Kroll Show / int_28f852ea
type
Wholesome Crossdresser
 Mystery Science Theater 3000 / int_28f852ea
type
Wholesome Crossdresser
 On Our Own / int_28f852ea
type
Wholesome Crossdresser
 1000 Ways to Die / int_28f852ea
type
Wholesome Crossdresser
 Queer as Folk / int_28f852ea
type
Wholesome Crossdresser
 Rowan and Martin's Laugh-In / int_28f852ea
type
Wholesome Crossdresser
 Some Mothers Do 'Ave 'Em / int_28f852ea
type
Wholesome Crossdresser
 Taskmaster / int_28f852ea
type
Wholesome Crossdresser
 The Golden Girls / int_28f852ea
type
Wholesome Crossdresser
 The Guest Book / int_28f852ea
type
Wholesome Crossdresser
 The Neighbors / int_28f852ea
type
Wholesome Crossdresser
 Tokusou Sentai Dekaranger / int_28f852ea
type
Wholesome Crossdresser
 Trailer Park Boys / int_28f852ea
type
Wholesome Crossdresser
 Transparent / int_28f852ea
type
Wholesome Crossdresser
 Twin Peaks / int_28f852ea
type
Wholesome Crossdresser
 Weinerville / int_28f852ea
type
Wholesome Crossdresser
 Win Ben Stein's Money / int_28f852ea
type
Wholesome Crossdresser
 You Rang, M'Lord? / int_28f852ea
type
Wholesome Crossdresser
 Luck & Logic (Tabletop Game) / int_28f852ea
type
Wholesome Crossdresser
 Maid RPG (Tabletop Game) / int_28f852ea
type
Wholesome Crossdresser
 A Chorus Line (Theatre) / int_28f852ea
type
Wholesome Crossdresser
 As You Like It (Theatre) / int_28f852ea
type
Wholesome Crossdresser
 La Cage aux folles (Theatre) / int_28f852ea
type
Wholesome Crossdresser
 La Fille du Régiment (Theatre) / int_28f852ea
type
Wholesome Crossdresser
 The Complete Works of William Shakespeare (abridged) (Theatre) / int_28f852ea
type
Wholesome Crossdresser
 Twelfth Night (Theatre) / int_28f852ea
type
Wholesome Crossdresser
 AdventureQuest Worlds (Video Game) / int_28f852ea
type
Wholesome Crossdresser
 Angélique (Video Game) / int_28f852ea
type
Wholesome Crossdresser
 Animal Crossing (Video Game) / int_28f852ea
type
Wholesome Crossdresser
 Animal Crossing: New Leaf (Video Game) / int_28f852ea
type
Wholesome Crossdresser
 Another Eden (Video Game) / int_28f852ea
type
Wholesome Crossdresser
 Battle Racing Stars (Video Game) / int_28f852ea
type
Wholesome Crossdresser
 Catherine (Video Game) / int_28f852ea
type
Wholesome Crossdresser
 Dandelion (Video Game) / int_28f852ea
type
Wholesome Crossdresser
 Dragon's Dogma (Video Game) / int_28f852ea
type
Wholesome Crossdresser
 Fighters Destiny (Video Game) / int_28f852ea
type
Wholesome Crossdresser
 Grand Theft Auto (Classic) (Video Game) / int_28f852ea
type
Wholesome Crossdresser
 Harvest Moon: A New Beginning (Video Game) / int_28f852ea
type
Wholesome Crossdresser
 Hatsune Miku: Project DIVA (Video Game) / int_28f852ea
type
Wholesome Crossdresser
 Jetpack Joyride (Video Game) / int_28f852ea
type
Wholesome Crossdresser
 Katamari Damacy (Video Game) / int_28f852ea
type
Wholesome Crossdresser
 Love Nikki - Dress Up Queen (Video Game) / int_28f852ea
type
Wholesome Crossdresser
 Median XL (Video Game) / int_28f852ea
type
Wholesome Crossdresser
 Mica: Apoptosis (Video Game) / int_28f852ea
type
Wholesome Crossdresser
 Mount & Blade (Video Game) / int_28f852ea
type
Wholesome Crossdresser
 Oracle of Tao (Video Game) / int_28f852ea
type
Wholesome Crossdresser
 Pangya (Video Game) / int_28f852ea
type
Wholesome Crossdresser
 Pokémon Gold and Silver (Video Game) / int_28f852ea
type
Wholesome Crossdresser
 Raving Rabbids (Video Game) / int_28f852ea
type
Wholesome Crossdresser
 Samurai Shodown (Video Game) / int_28f852ea
type
Wholesome Crossdresser
 Scribblenauts (Video Game) / int_28f852ea
type
Wholesome Crossdresser
 StreetPass Mii Plaza (Video Game) / int_28f852ea
type
Wholesome Crossdresser
 Suikoden V (Video Game) / int_28f852ea
type
Wholesome Crossdresser
 Super Mario Maker (Video Game) / int_28f852ea
type
Wholesome Crossdresser
 Super Mario Odyssey (Video Game) / int_28f852ea
type
Wholesome Crossdresser
 Tales Of Hetalia (Video Game)
seeAlso
Wholesome Crossdresser
 Tales of Xillia (Video Game) / int_28f852ea
type
Wholesome Crossdresser
 Tears to Tiara 2 (Video Game) / int_28f852ea
type
Wholesome Crossdresser
 The Witcher 3: Wild Hunt (Video Game) / int_28f852ea
type
Wholesome Crossdresser
 Tomodachi Life (Video Game) / int_28f852ea
type
Wholesome Crossdresser
 Disney Magical World / Videogame / int_28f852ea
type
Wholesome Crossdresser
 Akatsuki no Goei (Visual Novel) / int_28f852ea
type
Wholesome Crossdresser
 Code Geass: Lost Colors (Visual Novel) / int_28f852ea
type
Wholesome Crossdresser
 Hakuouki (Visual Novel) / int_28f852ea
type
Wholesome Crossdresser
 Katawa Shoujo (Visual Novel) / int_28f852ea
type
Wholesome Crossdresser
 Mahou Tsukai no Yoru (Visual Novel) / int_28f852ea
type
Wholesome Crossdresser
 Maji de Watashi ni Koi Shinasai! (Visual Novel) / int_28f852ea
type
Wholesome Crossdresser
 Rewrite (Visual Novel) / int_28f852ea
type
Wholesome Crossdresser
 You and Me and Her (Visual Novel) / int_28f852ea
type
Wholesome Crossdresser
 Happy Tree Friends (Web Animation) / int_28f852ea
type
Wholesome Crossdresser
 Ask That Guy with the Glasses (Web Video) / int_28f852ea
type
Wholesome Crossdresser
 Benzaie (Web Video) / int_28f852ea
type
Wholesome Crossdresser
 Drawfee (Web Video) / int_28f852ea
type
Wholesome Crossdresser
 Epic Rap Battles of History (Web Video) / int_28f852ea
type
Wholesome Crossdresser
 JonTron (Web Video) / int_28f852ea
type
Wholesome Crossdresser
 Joueur du Grenier (Web Video) / int_28f852ea
type
Wholesome Crossdresser
 Strawberry Dragon Project (Web Video) / int_28f852ea
type
Wholesome Crossdresser
 The Try Guys (Web Video) / int_28f852ea
type
Wholesome Crossdresser
 Brawl in the Family (Webcomic) / int_28f852ea
type
Wholesome Crossdresser
 Cobweb and Stripes (Webcomic) / int_28f852ea
type
Wholesome Crossdresser
 Demon Candy: Parallel (Webcomic) / int_28f852ea
type
Wholesome Crossdresser
 DOUBLE K (Webcomic) / int_28f852ea
type
Wholesome Crossdresser
 Evil FTW (Webcomic) / int_28f852ea
type
Wholesome Crossdresser
 Footloose
seeAlso
Wholesome Crossdresser
 Girls with Slingshots (Webcomic) / int_28f852ea
type
Wholesome Crossdresser
 HighSchoolAUShenanigans
seeAlso
Wholesome Crossdresser
 Kagerou (Webcomic) / int_28f852ea
type
Wholesome Crossdresser
 Material Girl (Webcomic)
seeAlso
Wholesome Crossdresser
 PinkBlack
seeAlso
Wholesome Crossdresser
 Skin Horse (Webcomic) / int_28f852ea
type
Wholesome Crossdresser
 Spinnerette (Webcomic) / int_28f852ea
type
Wholesome Crossdresser
 Sticky Dilly Buns (Webcomic) / int_28f852ea
type
Wholesome Crossdresser
 The Oceans Of Tumblr (Webcomic) / int_28f852ea
type
Wholesome Crossdresser
 Tsunami Channel (Webcomic) / int_28f852ea
type
Wholesome Crossdresser
 XY Adventures (Webcomic) / int_28f852ea
type
Wholesome Crossdresser
 Yaoi Tales (Webcomic) / int_28f852ea
type
Wholesome Crossdresser
 Neopets (Website) / int_28f852ea
type
Wholesome Crossdresser
 Bugs Bunny / int_28f852ea
type
Wholesome Crossdresser
 Fanboy and Chum Chum / int_28f852ea
type
Wholesome Crossdresser
 House of Mouse / int_28f852ea
type
Wholesome Crossdresser
 Jimmy Two-Shoes / int_28f852ea
type
Wholesome Crossdresser
 Johnny Bravo / int_28f852ea
type
Wholesome Crossdresser
 Lilo & Stitch / int_28f852ea
type
Wholesome Crossdresser
 Mighty Mouse / int_28f852ea
type
Wholesome Crossdresser
 Mulan / int_28f852ea
type
Wholesome Crossdresser
 Ōban Star-Racers / int_28f852ea
type
Wholesome Crossdresser
 Pinocchio and the Emperor of the Night / int_28f852ea
type
Wholesome Crossdresser
 Rango / int_28f852ea
type
Wholesome Crossdresser
 SheZow / int_28f852ea
type
Wholesome Crossdresser
 Sonic Underground / int_28f852ea
type
Wholesome Crossdresser
 Space Ghost Coast to Coast / int_28f852ea
type
Wholesome Crossdresser
 TaleSpin / int_28f852ea
type
Wholesome Crossdresser
 The Looney Tunes Show / int_28f852ea
type
Wholesome Crossdresser
 Toopy and Binoo / int_28f852ea
type
Wholesome Crossdresser
 Ultimate Spider-Man / int_28f852ea
type
Wholesome Crossdresser
 What's Opera, Doc? / int_28f852ea
type
Wholesome Crossdresser
 Woody Woodpecker / int_28f852ea
type
Wholesome Crossdresser
 Gankutsuou / int_28f852ea
type
Wholesome Crossdresser
 Himawari! / int_28f852ea
type
Wholesome Crossdresser
 Phi Brain: Puzzle of God / int_28f852ea
type
Wholesome Crossdresser
 Potemayo / int_28f852ea
type
Wholesome Crossdresser
 R.O.D the TV / int_28f852ea
type
Wholesome Crossdresser
 Facing the Future Series (Fanfic) / int_28f852ea
type
Wholesome Crossdresser
 Noir Ange / Fan Fic / int_28f852ea
type
Wholesome Crossdresser
 Ladybugs / int_28f852ea
type
Wholesome Crossdresser
 Scrapped Princess / int_28f852ea
type
Wholesome Crossdresser
 Sukisho / int_28f852ea
type
Wholesome Crossdresser
 wholesomecrossdresser
sameAs
Wholesome Crossdresser
 Mahoraba (Manga) / int_28f852ea
type
Wholesome Crossdresser
 Granado Espada (Video Game) / int_28f852ea
type
Wholesome Crossdresser
 Amplitude (Visual Novel) / int_28f852ea
type
Wholesome Crossdresser
 CLANNAD (Visual Novel) / int_28f852ea
type
Wholesome Crossdresser
 Sunstone (Webcomic) / int_28f852ea
type
Wholesome Crossdresser
 The Brothers Grunt / int_28f852ea
type
Wholesome Crossdresser
 Underdog / int_28f852ea
type
Wholesome Crossdresser