History Main / DraggedIntoDrag

* In the Myth/NorseMythology tale [[https://en.wikipedia.org/wiki/%C3%9Erymskvi%C3%B0a Thrymskvitha]], Thor is convinced by Heimdall to dress up as the goddess Freya and pretend to marry the jotun Thrym, in order to retreive the hammer that Thrym had stolen. It takes surprisingly little convincing, and most of the story is focused on the [[HilarityEnsues hilarity that ensues]] when Loki, dressed as the bridesmaid, has to convince the party of jotnar of why "Freya" looks like a bulky, bearded homicidal maniac.

-->'''Stumpy:''' Why me?
-->'''Kaeloo and Mr. Cat:''' Because.

* [[ZigZaggingTrope Zig-zagged]] in ''Anime/BlendS''. Hideri is ''already'' a WholesomeCrossdresser 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.

* ''Manga/FruitsBasket'': When all the girls want to make (and succeed) Yuki crossdress.

** 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.

** It gets worse for poor Ayla over the Christmas vacation.[[note]]In fact, it was a [[AnAsskickingChristmas pretty bad vacation]] for ''everybody'' on Team Kimba, except maybe Hank.[[/note]] While out shopping with his older sister [[{{Transgender}} 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 (along with MakeoverTorment), 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...

* ''Series/RuPaulsDragRace'': In the OnceASeason makeover challenge in Season 6, the queens had to make over straight grooms into drag brides (while the brides were whisked away to be fitted for masculine tuxedoes). Contestant Joslyn Fox revealed that her partner for the challenge was actually forced into it by his fiancee because she caught him cheating.

Sister trope to 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.

* 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.

* Cha Ji-Yyoung is a journalist who makes a horrible mistake in the Koran webtoon ''Webcomic/UsefulGoodForNothing'', and ends up Dragged Into Drag to go undercover in a [[OneGenderSchool female university]].

* 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.]]

* Yuna and Kakizaki in ''Manga/MahouSenseiNegima'' did this to Negi as a prop/attraction to their haunted house (which became far less haunted).

* ''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 to dress as a {{Meido}} much, aside from some slight embarrassment. Maybe he's gotten used to it by that point?

[[folder:Comic books]]

-->'''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!

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

* In ''VideoGame/Persona4,'' 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]]."]]

* ''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/OzyAndMillie'': Millie seems to have too much fun doing this to Ozy on occasion.

'''*cue GilliganCut*'''

* '' 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.

* 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.

** 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 ''Manga/SasamekiKoto'', Akemiya initially crossdresses by choice, but is later forced to dress as a girl to be used as, well, uh, lesbian bait.

* ''Manga/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. [[https://www.youtube.com/watch?v=tZZtlmAGDZE Here, see for yourself.]]

* In LetsPlay/{{Chuggaaconroy}}'s ''VideoGame/AnimalCrossing: New Leaf'' playthrough, when he lets LetsPlay/ProtonJon decide which fanmade design he'll wear for a week. Jon being [[{{Troll}} Jon]], he chooses the [[Franchise/SuperMarioBros Princess Peach]] dress.