[[quoteright:300:[[Manga/HayateTheCombatButler http://static.tvtropes.org/pmwiki/pub/images/hayate_dressup.jpg]]]]
[[caption-width-right:300:Nagi and Maria discover the joys of playing dressup.]]

Whenever a guy happens to [[{{Crossdresser}} need girls' clothes]] for some reason, the girls around him suddenly get a PsychoticSmirk... 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 PlayedForLaughs, sometimes accompanied by a GilliganCut.

Sometimes, the guy being dressed up may have [[DudeLooksLikeALady feminine attributes]] and other characters [[UnsettlingGenderReveal mistake them]] for being a [[AttractiveBentGender pretty girl]], possibly falling in LoveAtFirstSight. If this happens, the guy will [[HoYay play along]] because he's too embarrassed to reveal his true identity.

Subtrope of DisguisedInDrag. Often combined with InstantCosplaySurprise. Contrast WholesomeCrossdresser, a guy who's totally into doing this thing and probably doesn't need a girl's input. May overlap with BecomingTheCostume.

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!!Examples:

[[foldercontrol]]

[[folder:Anime & Manga]]
* ''Webcomic/ChaosAttack'' 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.
* ''Manga/ToLoveRu'' has this when Rito gets turned into a girl.
* In ''Manga/HayateTheCombatButler'' (pictured) this is a RunningGag for poor [[DudeLooksLikeALady 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 IThinkYouBrokeHim when Nagi suggests he change out of Ayumu's clothes, and he refuses. In actuality, he just doesn't want to [[UnsettlingGenderReveal 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 [[spoiler: 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...
* BlackButler: Done in especially disturbing fashion, as Ciel is 13 years old at most, and the scene opens such that it looks like he's being raped. [[http://www.youtube.com/watch?v=tZZtlmAGDZE Here, see for yourself]]
* ''Anime/CodeGeass'': Milly decides to have fun with a crossdressing day at school. [[http://www.youtube.com/watch?v=BO4Vn9M97Pk Much to Lelouch's consternation.]]
** "''How cruel! To call her a dog like that?''"
*** "''...why are you all so good at this?''"
* Yuna and Kakizaki in ''MahouSenseiNegima'' did this to Negi as a prop/attraction to their haunted house (which became far less haunted).
* Katsuki from ''VisualNovel/{{Clannad}}''. And the guys end up confusing him with a girl.
* ''{{Mahoraba}}'': Shiratori gets this done to him while he's asleep, in the manga just for such a light-weight drinker, in the anime for having an apparently dirty dream about Kozue.
* ''Anime/ErgoProxy'': Pino puts makeup on Vincent.
* Twice in ''MidoriNoHibi'':
** First, when there's a pervert on subway trains cutting girls' skirts, Ayase has Seiji dress in drag in order to catch the suspect.
** 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. [[spoiler: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.]]
* ''Manga/MinamiKe'': Makoto originally, but he eventually turns into a WholesomeCrossdresser when he realizes there are upsides to it, too...
* ''Manga/FruitsBasket'': When all the girls want to make (and succeed) Yuki crossdress.
* In ''SasamekiKoto'', Akemiya initially crossdresses by choice, but is later forced to dress as a girl to be used as, well, uh, lesbian bait.
* In ''Anime/{{Slayers}}'', OnceASeason, 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.
* When Sanji in ''Manga/OnePiece'' found himself on the "Isle of Maidens" Peachy Island he was thrilled... up until he discovered that all the "Maidens" were {{Transvestite}}s who insisted he go native.
** Also happened a bit to Luffy on Amazon Lily. The amazons made copies of his original clothing for him, but also added a bunch of pink frills to make him look cute. Luffy was not pleased.
*** Arguable, considering it was completely unintentional. The amazon that made the clothes seemed genuinely surprised when Luffy told her he didn't want frills on his clothes, and she removed them without any real argument when asked.
* Gintoki and Katsura were forced to crossdress and work at a crossdressing bar in an episode of ''Manga/{{Gintama}}''.
* This is more or less the point of ''FamilyCompo''.
* Kafuka Fuura and Harumi Fujoshi in ''SayonaraZetsubouSensei'' once forced their teacher and his brother into dresses.
* ''Anime/{{Pokemon}}'': 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 too dress as a {{Meido}} much aside from some slight embarrassment.
* GenderFlipped in ''OuranHighSchoolHostClub'' 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 [[ItMakesSenseInContext 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.
* In ''ScrappedPrincess'', Pacifica and Winia are happy to dress up Leopold and Fully in drag to sneak past soldiers.
* Pretty much the entire premise of ''PrincessPrincess''. Though instead of being dressed up by girls it's the AbsurdlyPowerfulStudentCouncil and ''school faculty'' who are behind it. ItMakesSenseInContext. Sort of.
* Done in the second season of DarkerThanBlack, where in one episode PluckyComicRelief 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.
* ''ShugoChara'': At one point, Kukai asks [[spoiler: Nagahiko]] what it feels like to wear a skirt. His response? Question it as [[BerserkButton an insult to his]] [[spoiler: [[WholesomeCrossdresser unorthodox]] [[BerserkButton family upbringing]]]], before taking out a copy of the girls school uniform and giving him and Tadase a practical demonstration.
* Early on in Season 2 of ''LightNovel/BakaToTestToShoukanjuu'', 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. [[SpringtimeforHitler This backfires.]] [[UnsettlingGenderReveal Horribly.]]
* All the guys, but especially, poor Tatsuya in ''Manga/HekikaiNoAION''. Since he was "sick" [[spoiler: (actually spending almost 2 month in a JourneyToTheCenterOfTheMind)]] 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.
* A villainous example in ''[[VideoGame/ApeEscape 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.
* ''Manga/ImARoyalTutorInMySistersDress'': Sherlock was forced to dress like his sister.
* 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.
* In ''LightNovel/ChuunibyouDemoKoiGaShitai'' (the light novels, not the [[AlternateContinuity anime]]), Rikka makes him dress like a MagicalGirl as a "punishment contract" and to give Yuuta the outfit as a present for their one month anniversary together... turns out that [[WholesomeCrossdresser fits him quite well too]].
* In ''NanaToKaoru'', Nana helps Kaoru dress up as a [[PlayboyBunny bunny]] for a school play.
* Nagisa from ''Anime/{{Free}}'' mentioned [[http://images3.wikia.nocookie.net/__cb20130915001050/free-anime/images/9/9c/Nagisa_and_his_bully_sisters.jpg 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.
* In ''WanderingSon'' 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 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.
* ''[[Anime/ElHazardTheMagnificentWorld 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.
* Sora ended up wearing a ballgown (with tiara) while [[{{Disney/SleepingBeauty}} Flora, Fauna and Merryweather]] tried to design him a new outfit in the manga adaptation for ''Manga/KingdomHeartsII''.
** His Nobody, Roxas, also found himself in drag in ''Manga/KingdomHearts358DaysOver2'', when he was forced to wear a FrenchMaidOutfit while trespassing the [[Disney/AliceInWonderland 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.
[[/folder]]

[[folder:Film -- Live Action]]
* In ''Film/{{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.
[[/folder]]

[[folder:Live Action TV]]
* It was done in at least one episode of ''Series/GilligansIsland''. The GilliganCut TropeNamer scene has Gilligan DraggedIntoDrag.
* Two episodes of ''SmallWonder'' had Jamie dressed as Vicki.
* ''Series/BigTimeRush'' 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.
* In an episode of ''[[ThirdRockFromTheSun 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 the third-season ''ModernFamily'' episode "Me? Jealous?", Alex and Haley decide to make up after [[TheGloriousWarOfSisterlyRivalry one of their frequent fights]] by dressing up Luke as a girl, something they haven't done in a long time.
* Claimed in an episode of ''BarneyMiller'', where a WholesomeCrossdresser 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.
[[/folder]]

[[folder:Video Games]]
* ''VideoGame/FinalFantasyVII'': At the Wall Market, Aeris seems rather enthusiastic about the idea of doing this to Cloud.
* Happens to Yuri and Ian in ''InfiniteSpace'', 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 NearRapeExperience where the pirates only responded to Ian's saying that he's a guy with "... even better."
* In ''DynastyWarriorsGundam 2'' Loran has this reaction when you unlock his Laura Rola party dress, despite not actually being all that bothered in ''Anime/TurnAGundam'' itself. In fact he mostly seems to have fun with it in series other with than the constricting corset.
* In ''VideoGame/{{Persona 4}},'' during the "Culture Club" event, [[AllMenArePerverts 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--[[spoiler: except for [[{{Bishonen}} Ted]], who makes [[DudeLooksLikeALady such a pretty girl]] that even a few guys remark that "[[StupidSexyFlanders I'd hit that]]."]]
* In the Fuka Bad End of ''VideoGame/{{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 ''VideoGame/FireEmblemAwakening'', Gregor can do this to Ricken in one of the DownloadableContent maps, ''Harvest Scramble''. Humorously, this manages to successfully dissuade a drunk woman who apparently tried to propose to Gregor.
* In ''VideoGame/WatchDogs'', 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).
[[/folder]]

[[folder:VisualNovels]]
* Shikanosuke in ''VisualNovel/KiraKira''. 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 ''LittleBusters'', 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 [[AttractiveBentGender and coo over]] [[{{Moe}} 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.
* During a ''VisualNovel/HatofulBoyfriend'' 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 [[ItMakesSenseInContext maids are the modern-day ninja]].
[[/folder]]

[[folder:Webcomics]]
* Cha Ji-Yyoung is a journalist who makes a horrible mistake in the Koran webtoon ''Webcomic/UsefulGoodForNothing'', and ends up [[CaptainObvious Dragged Into Drag]] to go undercover in a [[OneGenderSchool female university]].
* Jacob from ''{{Monsterful}}'' was forced to dress in both a ''[[http://www.monsterful.com/chapter07page13.html gothic lolita dress]]'' and in a ''[[http://www.monsterful.com/chapter07page18.html sailor uniform]]'' by the little evil Ruby.
* ''WebComic/OzyAndMillie'': Millie seems to have too much fun doing this to Ozy on occasion.
* ''WebComic/ElGoonishShive'' has a whole arc on The Birthday Party that involved splitting invited people into pairs to choose clothes for each other and [[spoiler:switching everyone's sex (except one character) using an [[ImportedAlienPhlebotinum alien]] "[[TransformationRay 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.
* ''Webcomic/DoubleK'' has [[TengenToppaGurrenLagann Kamina]] forcing Simon into the role of the DirtyHarriet to bust solicitors. He's done this more times than he really should, according to [[DaChief Lord Genome]].
* Inferno from APTComic is forced into this a lot apparently, but so far it's just a TakeOurWordForIt.
* In ''{{Drowtales}}'', Nau'kheol and Khal'harror [[http://www.drowtales.com/mainarchive.php?sid=7067 get forced to do this]] in order to sneak into the female section of the local WizardingSchool.
[[/folder]]

[[folder:Web Original]]
* An extremely common trope in transgender fiction, as seen on sites like [[http://www.fictionmania.tv/ FictionMania]]. In TG fiction, the trope is less likely to be PlayedForLaughs, instead often leading to a revelation of AttractiveBentGender and representing a first step on a journey of self-discovery (which may be figurative and/or [[ManIFeelLikeAWoman literal]].) Alternatively, the trope is sometimes given a more sinister spin, as a prelude to sexual domination and/or the protagonist becoming a SexSlave.
* The main theme of the [[FanFic/NewLookSeries New Look Series]].
* While raping him, Spoony forced WebVideo/TheNostalgiaCritic to dress up like a dirty ballerina and took pictures for blackmail purposes.
* In ''WebVideo/DemoReel'', as punishment for upsetting her (and because she thinks he looks good in it), Rebecca makes Tacoma dress up like Belle from ''Disney/BeautyAndTheBeast''.
* ''[[http://dovsherman.deviantart.com/art/The-Sissy-Alphabet-159042786 The Sissy Alphabet]]'' by [=DovSherman=] on Website/DeviantArt.
* The Literature/WhateleyUniverse, naturally. 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 [[PersonOfMassDestruction 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 even worse for poor Ayla over the Christmas vacation [[note]]in fact, it was a pretty bad vacation for ''everybody'' on Team Kimba, except maybe Hank[[/note]]. While out shopping with with his 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. HilarityEnsues, at least until the monster the MCO was ''actually'' after shows up. Then came the screaming and the bleeding as the EldritchAbomination 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...
[[/folder]]

[[folder:Western Animation]]
* In the "Just Desserts" episode of ''WesternAnimation/TheLittleRascals'', Darla fell ill just before the big baking contest, so Alfalfa had to dress like a girl and take Darla's place.
* ''Disney/TheLionKing'' has Timon and Pumbaa [[WeNeedADistraction providing a diversion]].
--> '''Simba:''' Come on, Timon. You guys need to create a diversion.\\
'''Timon:''' What do you want me to do, [[TemptingFate dress up in drag and do the hula?]]\\
'''*cue GilliganCut*'''
* In ''WesternAnimation/{{Kaeloo}}'', Stumpy is often shunted into female roles when playing pretend, whereas the others [[TheSmurfettePrinciple all play as males]]. He even [[LampshadeHanging lampshades]] the fact that Kaeloo is an actual female (or at least the [[{{Hermaphrodite}} closest thing present]]) and that it would make more sense for her to play such roles.
* In ''WesternAnimation/TheFairlyOddParents'' Timmy is forced into cleaning Vicky's room while dressed in a maid costume.
* [[SpongebobSquarepants Spongebob's]] uniform when Squidward is living in his house.
* In ''WesternAnimation/TeenTitans'', Cyborg's [[InitiationCeremony initiation]] to [[AcademyofEvil Hive Academy]] involves wearing a dress in the halls, among other things.
* In [[WesternAnimation/LooneyTunes "Banty Raids"]], WesternAnimation/FoghornLeghorn is [[BoundAndGagged bound and beak-tied]] and forcibly dressed in drag by a machine, then married to a horny beatnik bantam.
[[/folder]]

[[folder:Real Life]]
* RobertPattinson used to be put in drag a lot by his older sisters. He grew out of it eventually.
* There is such a thing as a "forced feminization" fetish.
[[/folder]]
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