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Dragged into Drag

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"What do you want me to do, dress up in drag and do the hula?"
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Whenever a guy happens to need girls' clothes for some reason, the girls around him suddenly get a Psychotic Smirk... oh boy. This activity is always portrayed as more fun for the girls than for the boy; girls in fiction just relish the opportunity to play with the victim like a doll and often revel in his discomfort. In most cases, this is all Played for Laughs, sometimes accompanied by a Gilligan Cut.

Sometimes, the guy being dressed up may have feminine attributes and other characters mistake them for being a pretty girl, possibly falling in Love at First Sight. If this happens, the guy will play along because he's too embarrassed to reveal his true identity.

Sister trope to Disguised in Drag. Often combined with Instant Cosplay Surprise. Contrast Wholesome Crossdresser, a guy who's totally into doing this thing and probably doesn't need a girl's input. May overlap with Becoming the Costume.

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Examples:

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    Anime & Manga 
  • In Assassination Classroom, during the Assassination Island Vacation arc, an incident causes Class E to have to undertake an infiltration mission through a hotel. At one point, the only way forward is through a crowded lounge to unlock a backdoor to continue the ascent, and Koro-sensei is in his immobile Absolute Defense form. As such, it is agreed that the girls would be sent through, as they would look most natural, but when concerns are raised about their potential vulnerability, Nagisa is made a bodyguard, and is soon convincingly dragged into a skirt, low-cut shirt and A-cup bra. Nagisa is forced into further incidents in the spin-off series Koro-Sensei Quest!.
  • Early on in season 2 of Baka and Test: Summon the Beasts, Akihisa, Yuuji, and Kouta are forced to crossdress and enter a yukata contest by their respective love interests as punishment for their attempts to hit on other girls. They then try to weasel their way out of it with their manly pride intact by losing the contest. This backfires. Horribly.
  • Zig-zagged in Blend-S. Hideri is already a Wholesome Crossdresser to begin with, but Mafuyu and Miu take great pleasure from forcing him into ridiculous outfits like a Stripperific magical girl costume or frilly doll clothing.
  • Katsuki from CLANNAD. And the guys end up confusing him with a girl.
  • Code Geass: Milly decides to have fun with a crossdressing day at school. Much to Lelouch's consternation.
    • "How cruel! To call her a dog like that?"
      • "...why are you all so good at this?"
  • Done in the second season of Darker Than Black, where in one episode Plucky Comic Relief Kiko and Gai from the first season bump into Suo, July, and Mao (whose currently residing in the body of a squirrel) and help Suo in her search for her mother in Toyko. During this time, Kiko and her friends dress up July (a reputedly emotionless male "doll" with no will of his own mind you) in frilly dresses and makeup until he apparently grows annoyed and leaves. It's one of the few lighthearted episodes of the series.
  • In Date A Live, Shido is forced to crossdress as "Shiori" in order to make Miku (who Does Not Like Men) fall in love with him. "Shiori" shows up on several more occasions, still as reluctant as the first time.
  • In one Detective School Q chapter, Megu and Ryu are sent to infiltrate into an all-girl school. Ryu is not keen on having to disguise himself as a female, but the teachers gave him no choice in the matter, so off he goes in a wig and a dress.
  • El-Hazard: The Magnificent World: Londs and Princess Rune invoke this, by deciding to use Makoto's likeness to Princess Fatora to their advantage by having him impersonate her, during the time of her abduction. When he refuses, they imprison him and Fujisawa in the castle tower until he finally agrees to do it.
  • Ergo Proxy: Pino puts makeup on Vincent.
  • In Family Compo, Masahiko frequently gets himself into situation where he needs to dress up as a girl.
  • Nagisa from Free! mentioned in the past that his sisters would dress him up as a girl and put makeup on him.
    • If Nitori is to be believed, Rin looks very nice in a maid outfit.
  • Fruits Basket: When all the girls want to make (and succeed) Yuki crossdress.
  • Gintoki and Katsura were forced to crossdress and work at a crossdressing bar in an episode of Gintama.
  • In Hayate the Combat Butler this is a Running Gag for poor Hayate. Nagi and Maria do this to him just for fun, and he has even been cursed into wearing only girls clothes. Some characters even think he is an actual crossdresser because of this.
    • This ends up crossing with I Think You Broke Him when Nagi suggests he change out of Ayumu's clothes, and he refuses. In actuality, he just doesn't want to reveal to Luca that he's actually a guy.
    • Hayate has become somewhat desensitized to it by the later manga, such as when Kotetsu forced him into a maid outfit to get into Comiket (long story) and he didn't even mind declaring he was a guy once some otaku tried taking photos of him, though being "a trap" only got them more excited. It pretty much came to a head in chapter 319 where he actually felt obligated to ask Hinagiku to borrow her school uniform...to wear... in an attempt to keep Ruka/Luca from finding out he was a guy. He might have felt forced into it, but one has to wonder if Maria has been getting to him...
  • All the guys, but especially, poor Tatsuya in Hekikai no AiON. Since he was "sick" (actually spending almost 2 month in a Journey to the Center of the Mind) he didn't know that his class was preparing a "Males-in-female-clothes cafe" for their Cultural Festival, and the girls rejoiced themselves in his cuteness when they saw him in a meido costume.
  • I'm a Royal Tutor in My Sister's Dress: Sherlock was forced to dress like his sister.
  • Sora ended up wearing a ballgown (with tiara) while Flora, Fauna and Merryweather tried to design him a new outfit in the manga adaptation for Kingdom Hearts II.
    • His Nobody, Roxas, also found himself in drag in Kingdom Hearts: 358/2 Days, when he was forced to wear a French Maid Outfit while trespassing the White Rabbit's house when the Rabbit came home, trying to trick him into thinking he was his servant, Mary Ann. However, the Rabbit saw through the disguise, and Roxas was put onto trial.
  • During the Cultural Festavel in Kitsune No Yomeiri, Kanon force Ousuke, Tarou and Yoichi to dress as Maids for the class' Maidonnote -café. The actually proved quite popular, especially Ousuke.
  • In Love, Chunibyo & Other Delusions (the light novels, not the anime), Rikka makes him dress like a Magical Girl as a "punishment contract" and to give Yuuta the outfit as a present for their one month anniversary together... turns out that fits him quite well too.
  • Mahoraba: Shiratori gets this done to him while he's asleep, in the manga just for being such a light-weight drinker, in the anime for having an apparently dirty dream about Kozue.
  • Midori Days:
    • First, when there's a pervert on subway trains cutting girls' skirts, Ayase has Seiji dress in drag in order to catch the suspect.
    • Seiji ends up participating in a women's wrestling match. Unfortunately, his shorts get pulled off at the least convenient time...
    • A running gag in the relationship between Kota and Miku is that Miku and her gang love to constantly dress Kota in drag, since (according to them) he "looks cute" in it. Toward the end of the manga, Kota later asks Miku and her gang to drag him up again, this time in a gambit to persuade Midori to return to her original body.
  • Minami-ke: Makoto originally, but he eventually turns into a Wholesome Crossdresser when he realizes there are upsides to it, too...
  • In episode 10 of the anime adaptation of Miss Kobayashi's Dragon Maid the characters decided to put on a production of The Little Match Girl for the old folks home. While deciding who to cast as the lead Lucoa suggests Shouta and dresses him up as the the titular match girl. He lasts a few minutes under their scrutiny before becoming too embarrassed.
  • In Nana to Kaoru, Nana helps Kaoru dress up as a bunny for a school play.
  • Yuna and Kakizaki in Negima! Magister Negi Magi did this to Negi as a prop/attraction to their haunted house (which became far less haunted).
  • When Sanji in One Piece found himself on the "Isle of Maidens" Peachy Island he was thrilled... up until he discovered that all the "Maidens" were Transvestites who insisted he go native.
  • Gender Flipped in Ouran High School Host Club when the boys are quite happy to dress up Haruhi (in men's clothing, making it this trope, as well as women's).
    • Tamaki manages to get all of the hosts (except for Mori) to dress up as girls in over-the-top costumes to get Haruhi to stay in the club (in the manga, though, only Hikaru, Kaoru, and Hunny played along, and Tamaki was also in gender-appropriate, if excessively frilly, attire).
    • Zigzagged in the anime finale, when the entire club is cross-dressing as women. So Haruhi is dressed as a man dressed as a woman.
  • Overlord (2012): When taking ideas from all Nazarick to improve the place, Mare and Aura (a crossdressing brother and sister) suggest that everyone start crossdressing. Ainz is able to convince them not to by pointing out that their crossdressing is the result of their creator's tastes, and that giving it to all Nazarick would make them less special in her eyes.
  • In the PandoraHearts sidestory "Knave of Hearts", Xerxes Break is forced into drag by the others. His mistress, Sharon, mentions that her mother used to subject him to modeling for her all the time.
  • Pokémon: The Series: In every saga (except for the Orange Islands one), Ash is forced into dressing up as a girl. Needless to say, it's never consensual on his part. In the Sinnoh one, he didn't seem to mind to dress as a Meido much, aside from some slight embarrassment. Maybe he's gotten used to it by that point?
  • The premise of Princess Princess revolves around the "Princess" system established by the all-boys school the main characters go to, where the prettiest boys are forced to dress up as girls to entertain the rest of the student body. And no, the students aren't really given a choice for the matter, although many are quite happy to oblige because of the additional benefits given to them.
  • In Rock Lee's Springtime of Youth, Neji is casted into female roles (And thus placed into dresses) during Lee's 'Genjutsu's'/skits, much to his displeasure.
  • A villainous example in Saru Getchu 2nd Ukki Pink magically dresses Kakeru in pink tank top and mini skirt, which forces him to make girly poses while she takes pictures of him.
  • Kafuka Fuura and Harumi Fujoshi in Sayonara, Zetsubou-Sensei once forced their teacher and his brother into dresses.
  • Shugo Chara!: At one point, Kukai asks Nagahiko what it feels like to wear a skirt. His response? Question it as an insult to his unorthodox family upbringing, before taking out a copy of the girls school uniform and giving him and Tadase a practical demonstration.
  • In Scrapped Princess, Pacifica and Winia are happy to dress up Leopold and Fully in drag to sneak past soldiers.
  • In Slayers, Once a Season, Lina and Amelia happily dress up the male part of the cast because the party needs a disguise. Ironically, in episode 17 of NEXT (when the party infiltrates a girls-only kingdom), Lina's the only one in her party wearing trousers in lieu of the dresses worn by her comrades.
  • To Love-Ru has this when Rito gets turned into a girl.
  • In Undefeated Bahamut Chronicle, the Triad make Lux dress up as a girl to join him in their patrols of the school, to investigate rumours of intruders.
  • Wandering Son:
    • Shiina was shown to have been crossdressed by his three older sisters when he was quite young. They eventually lost interest and stopped once he grew older and stopped looking so feminine.
    • Played more darkly with Yuki (a transgender woman) when she was in middle school. She was forced by bullies to wear the female uniform and ended up becoming a hikikomori for several years.
  • In Whispered Words, Akemiya initially crossdresses by choice, but is later forced to dress as a girl to be used as, well, uh, lesbian bait.
  • In Yo-Kai Watch: Wakuwaku Nyanderful Days, Dazzabel forces others to wear elaborate dresses, nevermind their gender. She forces Nate into a dress at one point.

    Comic Books 
In a Titeuf comic where Titeuf think that Nadia is gonna get married, one of his plan to separate Nadia and his Unknown Rival is to have Manu dressed as a girl and to pretend he's married to him all along so Nadia would gets jealous and breaks up. It doesn't work.

    Comic Strip 
  • Crabgrass: in this comic, Krystal forces Kody to dress up like a princess. Kyle considers it worse than his own responsibility to look after Kevin.
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    Film — Live-Action 
  • In Beauty and the Beast (2017), Madame de Gaderobe dresses Tom, Dick, and Stanley up in ballgowns and makeup during the fight at the castle. Tom and Dick shriek and run away. Stanley, however, doesn't seem to mind, and even gives a large grin.
    Madame de Gaderobe: Go! Be free!
  • Played for Drama in The Heart Is Deceitful Above All Things, in which the drug-addled prostitute Sarah forces her son Jeremiah (played by Dylan and Cole Sprouse) to crossdress so he can be her "little sister".
  • In Unconscious, Salvador and Alma find themselves at a ball where crossdressing is de rigeur. Salvador is a lot less enthusiastic about the idea than Alma is.

    Literature 
  • Harry Potter and the Prisoner of Azkaban has a weird case involving a magical creature affected by your thoughts—the Boggart, appearing as your greatest fear, appears as Professor Snape for Neville. To defeat a Boggart, you must force the Boggart into a form that is "funny". When Neville faces the Snape-Boggart, his spell forces it into his grandmother’s clothing.

    Live-Action TV 
  • Aquí no hay quien viva: On an episode, Fernando's Drag Queen father can't do a performance due to illness, and asks him and Mauri to fill in for him. Neither of them is exactly brimming with enthusiasm over it.
  • Claimed in an episode of Barney Miller, where a Wholesome Crossdresser gets arrested and is forced by circumstances to call a pal from work to bail him out. He claims he was mugged and they stole his clothes; but that doesn't explain why he has $50 in his purse.
    • In several other episodes, one of the male detectives would be ordered to dress as a woman and walk through the park as bait for muggers. How successfully they disguised themselves as women varied greatly, with Dietrich being the least successful and Harris being the most successful (once he shaved off his mustache).
  • Big Time Rush also showcased this when one of the guys dressed as a girl to get into an all female school to meet a favorite author of his.
  • It was done in at least one episode of Gilligan's Island. The Gilligan Cut Trope Namer scene has Gilligan Dragged into Drag.
  • In the third-season Modern Family episode "Me? Jealous?", Alex and Haley decide to make up after one of their frequent fights by dressing up Luke as a girl, something they haven't done in a long time.
  • Two episodes of Small Wonder had Jamie dressed as Vicki.
  • In an episode of The Suite Life of Zack and Cody, Cody disguises himself as a girl when he enters a Beauty Contest to win the prize money so he and Zack can buy bikes.
  • In an episode of 3rd Rock from the Sun, Sally decided she needed to experience a childhood, so she started acting like a little girl. This included styling Tommy's hair into pigtails and so forth. He did not enjoy it.
  • In an episode of Wingin' It Carl has to wear a dress and has to model it.

    Music 
  • The 1982 album Chipmunk Rock had Simon and Theodore coax Alvin into dressing up like a girl to be the lead singer for "Leader of the Pack," with Theodore joking they could be "the Chipettes" (predating the actual Chipettes' debut by a year) in performing what Alvin refers to as "a girls' song". (Later releases of the song would cut out this intro.)
  • "I'm a Boy" by The Who is about a boy being raised as a girl by his mother and his sisters against his wishes.

    Video Games 
  • In the Fuka Bad End of Disgaea 4: A Promise Unforgotten, Fuka decides that the recently defeated Valvatorez and Fenrich would look good in maid outfits.
    Fuka: You guys aren't that bad looking... I wouldn't mind making you hunks my servants. But... You gotta wear maid costumes from now on.
    Fenrich: My lord in a maid costume...!? A-are you into that sort of thing, lass? That's unacceptable!
  • In Dynasty Warriors: Gundam 2 Loran has this reaction when you unlock his Laura Rola party dress, despite not actually being all that bothered in ∀ Gundam itself. In fact he mostly seems to have fun with it in series other with than the constricting corset.
  • Final Fantasy VII: At the Wall Market, Aeris seems rather enthusiastic about the idea of doing this to Cloud.
    • Expanded on in the Final Fantasy VII Remake; Cloud rejects and resents the idea of dressing up at all, insisting Aerith go alone up until the last moment after Leslie repeatedly warns him. Aerith agrees and excitedly drags him to Andrea Rhodea. During the entire process of getting Andrea's approval, its obvious Cloud is uncomfortable while Aerith is cheering him on. Afterwards he very much does not want to talk about what he looks like, although Aerith is in awe of how pretty he looks.
      Aerith: This is our plan, and you'll learn to love it.
  • In Fire Emblem Awakening, Gregor can do this to Ricken in one of the Downloadable Content maps, Harvest Scramble. Humorously, this manages to successfully dissuade a drunk woman who apparently tried to propose to Gregor.
  • In the first installment of the Galaxy Angel II trilogy this happens to Kazuya for players who plan to go the Natsume route. It isn't his first time, as he's been made to crossdress several times at a cafe he worked at before joining the Rune Angels.
  • Happens to Yuri and Ian in Infinite Space, with the dialogue suggesting they lost some sort of bet to Nia, and this leads to Ian being kidnapped alongside the barmaid of the place where they slept at. There's a Near-Rape Experience where the pirates only responded to Ian's saying that he's a guy with "... even better."
  • Happens twice in The Legend of Heroes: Trails in the Sky, both times to Joshua. The first time is so he can play the princess in a gender swapped production of a play about two knights dueling for 'her' hand. The second time is to get him into a restricted part of the palace by disguising him as a maid. He looks disturbingly good in a dress.
  • In Persona 4, during the "Culture Club" event, Yosuke signs up the female characters for the Beauty Pagent, which they can't back out of. To get their revenge, the girls sign the boys up for the "Crossdressing Pagent" held directly before. And they take great delight in dolling the boys up in humorously hideous outfits— except for Teddie, who makes such a pretty girl that even a few guys remark that "I'd hit that."
  • In Sands of Destruction, this is apparently how characters feel about being equipped with accessories meant for the opposite gender. They'll wear them, but their morale will take a hit and you'll start your turn in battle with fewer moves. Of course, the gender of some accessories seems pretty arbitrary: earrings are all for girls, but Naja and Agan are both shown to wear them in their portraits (and they seem to be very similar in style to the girls' earrings). Likewise, bangles are for boys, but Morte seems to be wearing some sort of bracelet on her right wrist. Confusingly, Taupy's preferences for equipment tend to follow the girls, yet he's never shown to be a Wholesome Crossdresser and is definitely not effeminate.
  • In Watch_Dogs, one of the Privacy Invasion collectables is a man being dressed up as a princess (off camera) by his daughter (and his attempts to talk her out of it without upsetting her).

    Visual Novels 
  • During a Hatoful Boyfriend Drama CD Ryouta really wanted Sakuya to spend an afternoon in maid garb working with him at a transvestite cafe. Sakuya was extremely reluctant, but Ryouta managed to cajole and trick him into agreeing, partly by convincing him that maids are the modern-day ninja.
  • Shikanosuke in Kira-Kira. Initially it was a way to get him into his friend Sarina's strict household since they wouldn't approve of a boy being left alone with girls. It eventually became part of his band costume to cross-dress.
  • Riki, the protagonist of Little Busters!, has a quite young, girly-looking face, so naturally there's a scene where the girls drag him along on a sleepover to force him to wear a girls' uniform and coo over how moe he looks. Hell, when another girl berates them for being too loud, she mistakes Riki for being a girl she doesn't recognise.
  • In Prince of Stride, Hozuki is forced to wear a dress when the team is modeling for Heath's sister brand.
  • The beginning of Highschool Romance has Shoji, the playable character, enrolled by mistake in an all-girl school, and since he really doesn't want to miss the year, Principal Lea decides that he can join, provided that he pass as a girl, and even decided to personally take him to get lingerie and clothes to wear. In Lea's path, she's shown to like having Shoji dressed up as a girl for her leisure, even kissing him when in drag. In Selena's ending, Shoji is persuaded to keep crossdressing in various fancy outfits for her personal benefit.

    Webcomics 
  • Inferno from APT Comic is forced into this a lot apparently, but so far it's just a Take Our Word for It.
  • Chaos Attack begins with Doah Lee being forced to get his older sisters soda while dressed up as a girl as part of a punishment game. Of course, he winds up getting attacked by an alien and subsequently rescued by a group of uber Bishounen superheroes, who quickly take a liking to him, but are not pleased when he reveals his gender. So they choose to have him pay them back for saving his life by having him be their manager.
  • DOUBLE K has Kamina forcing Simon into the role of the Dirty Harriet to bust solicitors. He's done this more times than he really should, according to Lord Genome.
  • In Drowtales, Nau'kheol and Khal'harror get forced to do this in order to sneak into the female section of the local Wizarding School.
  • El Goonish Shive has a whole arc on The Birthday Party that involved splitting invited people into pairs to choose clothes for each other and switching everyone's sex (except one character) using an alien "morphing device", so that all the characters were cross-dressed into whatever their partners wanted. It's not as bad as it sounds, but surely as crazy.
  • Jacob from Monsterful was forced to dress in both a gothic lolita dress and in a sailor uniform by the little evil Ruby.
  • Ozy and Millie: Millie seems to have too much fun doing this to Ozy on occasion.
  • Cha Ji-Yyoung is a journalist who makes a horrible mistake in the Korean webtoon Useful Good For Nothing, and ends up Dragged Into Drag to go undercover in a female university.

    Web Original 
  • An extremely common trope in transgender fiction, as seen on sites like FictionMania. In TG fiction, the trope is less likely to be Played for Laughs, instead often leading to a revelation of Attractive Bent-Gender and representing a first step on a journey of self-discovery (which may be figurative and/or literal.) Alternatively, the trope is sometimes given a more sinister spin, as a prelude to sexual domination and/or the protagonist becoming a Sex Slave.
  • The main theme of the New Look Series.
  • While raping him, Spoony forced The Nostalgia Critic to dress up like a dirty ballerina and took pictures for blackmail purposes.
  • In Demo Reel, as punishment for upsetting her (and because she thinks he looks good in it), Rebecca makes Tacoma dress up like Belle from Beauty and the Beast.
  • The Sissy Alphabet by DovSherman on DeviantArt.
  • The Whateley Universe, naturally, mostly involving reluctant Gender Benders such as Ayla or (at the time) Nikki. The First Law of Gender-Bending generally applies in this series, but the Second less so, meaning that a few (like Ayla and Pat) stay reluctant; as a result, expectations of conforming to assumed gender roles can end up hitting them particularly hard, often leading to this.
    • In the Halloween stories, Phase (Ayla Goodkind, who is male but looks like a female supermodel) knows his team is doing a Tenchi Muyo theme because Tennyo can't help looking like Ryoko. Generator tells him he doesn't have to worry about the costume. He has to go, because he's certain there will be an attempt on Carmilla's life (he's right). His costume? Not Tenchi. He's not happy being dressed as Tsunami.
    • It gets worse for poor Ayla over the Christmas vacation.note  While out shopping with his older sister Gracie, he finds himself surrounded by a combat team from the Mutant Commission Office, and fearing they were after him, they duck into a nearby theatre... which just happens to be hosting a Beauty Pageant. Hilarity Ensues (along with Makeover Torment), at least until the monster the MCO was actually after shows up. Then came the screaming and the bleeding as the Eldritch Abomination nearly kills everyone. Oh, and the MCO? They try to pin the rap for summoning it on Ayla. And after all that, to add insult to injury, his body hair never grows back after the wax treatment Gracie gave him...
    • Recently transformed Cosmic Plaything Josie Gillman's older sister and her friends rather aggressively made Josie dress in the most obnoxiously girly clothes they could find (which turned out to be a very short skirt and a pink baby tee with the word 'Skank' on it in glitter ink) while inflicting Makeover Torment (and dropping 'helpful' tips about picking up boys), before sending her out on a date with a girl who, as it happens, was still unaware that Josh was no longer male.[1] Supposedly, Melissa did this in order to distract Josie from being depressed, but since this depression was caused by, you know, her turning into a girl and all, this backfired quite spectacularly.[2]
  • In Dolly Wolly by HinaYui on DeviantArt, this happens just before Laruen begins the Humiliation Conga on Mark.
  • In Chuggaaconroy's Animal Crossing: New Leaf playthrough, when he lets ProtonJon decide which fanmade design he'll wear for a week. Jon being Jon, he chooses the Princess Peach dress. The design beat at least five designs featuring a certain Pikmin from Chugga's solo LP of Pikmin.
    Emile: YOU SON OF A CANADIAN!
  • Otoko no Ko wa Meido Fuku ga Osuki!?: Yuki is unwillingly dragged into working as a maid at Cherry Girls (a maid cafe composed of boys dressed as maids for staff), much to his disdain.
  • Played for Drama in Danganronpa Re:Birth: Ayumu was forced into cross-dressing by his Big Sister Bully Emi, and is not okay with doing so.
  • The New Hansel and Gretel: On their second day, Mathair dresses Jack and Jamie up in more than just diapers. Mathair briefly considers dressing Jack up as a girl to have "two baby girls" just to torment him.

    Western Animation 
  • In an episode of the 1994 cartoon series Baby Huey, Huey's father is taken hostage by anthropomorphic, malevolent eggs and is forced to be a damsel in distress and is tied to a play train track as the eggs ride the train to run him over. He is dressed with a blond wig, dress and lipstick, although he does not seem to be embarrassed or content with the drag, and is more frightened by the fact he may be run over by a train.
  • In "Banty Raids", Foghorn Leghorn is bound and beak-tied and forcibly dressed in drag by a machine, then married to a horny beatnik bantam.
  • Beauty and the Beast: During the battle of the castle the Wardrobe catches one villager in her drawers and spits him back out in rather hideous drag, with makeup. Prompting a rather girlish scream from him.
  • Dexter's Laboratory had, in the episode "Dos Boot", Dexter and Mandark forced into wearing dresses (as Paper People) due to Dexter's sister Dee Dee manipulating a Bland-Name Product of Photoshop, and this episode is notorious for this rather creepy ending. Fortunately, Status Quo Is God, so this horror for them was undone by the next episode, thanks to a Snap Back and Negative Continuity.
  • The Fairly OddParents:
    • Timmy is forced into cleaning Vicky's room while dressed in a maid costume.
    • In one of the Oh Yeah! Cartoons shorts, Cosmo and Wanda bring Timmy to a dance in a pumpkin coach, which turned out to include a dress because they couldn't "break the ensemble".
  • In Kaeloo, Stumpy is often shunted into female roles when playing pretend, whereas the others all play as males. He even lampshades the fact that Kaeloo is an actual female (or at least the closest thing present) and that it would make more sense for her to play such roles.
    Stumpy: Why me?
    Kaeloo and Mr. Cat: Because.
    • In one of the episodes, the gang are Playing House. Kaeloo is the mother, Mr. Cat is the father, Stumpy is their son, and Quack Quack is forced by Kaeloo to dress as a girl to play the daughter.
  • The Lion King (1994) has Timon and Pumbaa providing a diversion.
    Simba: Come on, Timon. You guys need to create a diversion.
    Timon: What do you want me to do, dress up in drag and do the hula?
    [cue Gilligan Cut]
  • In the "Just Desserts" episode of The Little Rascals, Darla fell ill just before the big baking contest, so Alfalfa had to dress like a girl and take Darla's place.
  • Peter No-Tail (1981): When the title character Pelle (the Swedish form of "Peter") decides to compete in a sports competition with the other cats, he is forced by resident bully Måns to wear a pink blouse with a heart on it. Måns claims its a "uniform" and that he's disqualified if he doesn't wear it; of course, Måns invented the competition to begin with.
  • The Simpsons: In the episode “Two Dozen and One Greyhounds”, Bart has his socks eaten by a group of Santa’s Little Helper’s puppies, necessitating him wearing Lisa’s frilly pink socks (which is entirely due to Rule of Funny, since her usual socks are white). He also has to wear a frilly pink skirt, even though his shorts are fine, apparently because he ‘has to co-ordinate’. He ends up being forced to go to school dressed like that.
    • Again for Bart in the later episode “Lisa Gets the Blues”, where Bart is forced to dress in a ‘little orphan Annie’ dress and perform one of the songs from the musical in front of a crowd by the bullies.
  • Spongebob's uniform when Squidward is living in his house.
  • In the Star vs. the Forces of Evil episode "St. Olga's Reform School For Wayward Princesses", Star and Marco have to infiltrate the eponymous Boarding School of Horrors, and Marco isn't happy about his disguise being a poofy pink-and-lavender dress.
    Marco: You couldn't have turned me into one of those guards with the cool masks?!
    Star: I dunno, pink is definitely your color.
    • Later episodes do show him a lot more open, seeing as how he receives royalty checks for Princess Marco merchandise and later in this episode, he asks if he can keep the dress.
  • In Teen Titans, Cyborg's initiation to Hive Academy involves wearing a dress in the halls, among other things.

    Real Life 
  • Robert Pattinson used to be put in drag a lot by his older sisters. He grew out of it eventually.

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