History Main / DraggedIntoDrag

-->'''Fudd:''' Gwacious! ''[[BreakingTheFourthWall (while running, he briefly pauses to address the audience)]]'' Have any of you girls ever had an expewience wike this?

* ''WesternAnimation/BeautyAndTheBeast'': 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.

** The nightmare scenes of ''WesternAnimation/TheBigSnooze'' has WesternAnimation/BugsBunny dolling up WesternAnimation/ElmerFudd in drag, giving him HartmanHips and breasts to boot.

* In a decidingly less wholesome manner, in order to recruit [[MissKitty Queen Roger]] in ''VideoGame/{{LISA}}: The Painful RPG'', Brad ends up dressing as a prostitute and working some shifts at his brothel. There’s a couple guys who flat out reject Brad, though a couple partake in his "services". Similarly, [[WebVideo/Jimquisition Slave Lord Jim]] forces Brad into a rather revealing dress[[note]] It’s the same sprite as Brad’s prostitute outfit[[/note]] during his sidequest on Dismal Island.

* In an episode of ''Series/ThirdRockFromTheSun'', 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.

-->'''Cricket:''' Look, I’m sorry I abandoned you, [[SuddenlyShouting but you you at least let me pick the dress]]?!

* ''Manga/Overlord2012'': 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 [[OtokonokoGenre their creator's tastes]], and that giving it to all Nazarick would make them less special in her eyes.

* In ''LightNovel/LoveChunibyoAndOtherDelusions'' (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 [[AttractiveBentGender fits him quite well too]].

* 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.

* ''WesternAnimation/LooneyTunes'': the nightmare scenes of "The Big Snooze" had Bugs dolling up Elmer in drag, giving him HartmanHips and breasts to boot.

* * In "WesternAnimation/{{The Powerpuff Girls|1998}}' Best Rainy Day Adventure Ever," the girls coerce the Professor into dressing up as Bubbles for their play-acting.

* ''WesternAnimation/TheSimpsons'': 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 RuleOfFunny, 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.
* [[WesternAnimation/SpongeBobSquarePants Spongebob's]] [[FrenchMaidOutfit 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 ''Manga/RockLeesSpringtimeOfYouth'', Neji is casted into female roles (And thus placed into dresses) during Lee's 'Genjutsu's'/skits, much to his displeasure.

---> '''Aerith:''' This is our plan, and you'll learn to love it.

Sister trope to DisguisedInDrag. Often combined with InstantCosplaySurprise. Compare MakeoverTorment, when the boy does not necessarily ''need'' to dress up like a girl, but is being forced to anyway as punishment by girls for something he did that teed them off. Contrast WholesomeCrossdresser, a guy who's totally into doing this thing and probably doesn't need a girl's input. May overlap with BecomingTheCostume.

* Early on in season 2 of ''LightNovel/BakaAndTestSummonTheBeasts'', 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.]]

* In ''WesternAnimation/VeggieTales'', they do a parody of Theatre/{{Hamlet}}, with Ophelia being played by the gravel-voiced, mustachioed Mr. Lunt in a dress. When he protests, Archibald reminds him that men playing female roles is Shakespearean tradition. Mr. Lunt reluctantly steps onto the stage, grumbling, "We're going to get letters about this one".

* In [[VideoGame/GalaxyAngel 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.

* In ''Manga/NanaToKaoru'', Nana helps Kaoru dress up as a [[PlayboyBunny bunny]] for a school play.

* * In "WesternAnimation/ThePowerpuffGirls' Best Rainy Day Adventure Ever," the girls coerce the Professor into dressing up as Bubbles for their play-acting.

* * In "WesterAnimation/ThePowerpuffGirls' Best Rainy Day Adventure Ever," the girls coerce the Professor into dressing up as Bubbles for their play-acting.

'''Timon:''' What do you want me to do, [[TemptingFate dress up in drag and do the hula?]]\\d
''[cue GilliganCut]''

'''Timon:''' What do you want me to do, [[TemptingFate dress up in drag and do the hula?]]\\

* Sora ended up wearing a ballgown (with tiara) while [[WesternAnimation/SleepingBeauty Flora, Fauna and Merryweather]] tried to design him a new outfit in the manga adaptation for ''Manga/KingdomHeartsII''.

* ''Literature/ImARoyalTutorInMySistersDress'': Sherlock was forced to dress like his sister.

* In ''LightNovel/DateALive'', Shido is forced to crossdress as "Shiori" in order to make Miku (who DoesNotLikeMen) fall in love with him. "Shiori" shows up on several more occasions, still as reluctant as the first time.

* ''Manga/ImARoyalTutorInMySistersDress'': Sherlock was forced to dress like his sister.

* In ''LightNovel/LoveChunibyoAndOtherDelusions'' (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 [[AttractiveBentGender fits him quite well too]].

* In ''LightNovel/ScrappedPrincess'', Pacifica and Winia are happy to dress up Leopold and Fully in drag to sneak past soldiers.

* In ''LightNovel/UndefeatedBahamutChronicle'', the Triad make Lux dress up as a girl to join him in their patrols of the school, to investigate rumours of intruders.