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- 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.
- To Love-Ru has this when Rito gets turned into a girl.
- 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...
- Black Butler: 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. Here, see for yourself
- 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?"
- "How cruel! To call her a dog like that?"
- Yuna and Kakizaki in Mahou Sensei Negima! did this to Negi as a prop/attraction to their haunted house (which became far less haunted).
- Katsuki from 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.
- Ergo Proxy: Pino puts makeup on Vincent.
- Twice in 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.
- 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...
- Fruits Basket: When all the girls want to make (and succeed) Yuki crossdress.
- In Sasameki Koto, Akemiya initially crossdresses by choice, but is later forced to dress as a girl to be used as, well, uh, lesbian bait.
- 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.
- 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.
- Gintoki and Katsura were forced to crossdress and work at a crossdressing bar in an episode of Gintama.
- In Family Compo, Masahiko frequently gets himself into situation where he needs to dress up as a girl.
- Kafuka Fuura and Harumi Fujoshi in Sayonara, Zetsubou-Sensei once forced their teacher and his brother into dresses.
- Pokémon: 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 use to it by that point?
- 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.
- In Scrapped Princess, Pacifica and Winia are happy to dress up Leopold and Fully in drag to sneak past soldiers.
- The premise of Princess Princess is about an all-boys school who sets up a "Princess" system where the prettiest ones 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 most people willing takes the duty because of the additional benefits given to them.
- 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.
- 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.
- 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.
- 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.
- 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.
- I'm a Royal Tutor in My Sister's Dress: Sherlock was forced to dress like his sister.
- In the Pandora Hearts 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 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.
- In Nana to Kaoru, Nana helps Kaoru dress up as a bunny for a school play.
- 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.
- In 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 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.
- 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 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.
Film — Live Action
- 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.
Live Action TV
- It was done in at least one episode of Gilligan's Island. The Gilligan Cut Trope Namer scene has Gilligan Dragged into Drag.
- Two episodes of Small Wonder had Jamie dressed as Vicki.
- 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.
- 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 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.
- 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.
- Final Fantasy VII: At the Wall Market, Aeris seems rather enthusiastic about the idea of doing this to Cloud.
- 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."
- 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 Turn A Gundam itself. In fact he mostly seems to have fun with it in series other with than the constricting corset.
- 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 Ted, who makes such a pretty girl that even a few guys remark that "I'd hit that."
- In the Fuka Bad End of Disgaea 4, 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 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 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).
- This is apparently how characters feel about being equipped with accessories meant for the opposite gender in Sands of Destruction: 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.
- 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.
- 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.
- In Prince Of Stride, Hozuki is forced to wear a dress when the team is modeling for Heath's sister brand.
- Cha Ji-Yyoung is a journalist who makes a horrible mistake in the Koran webtoon Useful Good For Nothing, and ends up Dragged Into Drag to go undercover in a female university.
- 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.
- 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.
- 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.
- Inferno from APT Comic is forced into this a lot apparently, but so far it's just a Take Our Word for It.
- 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.
- 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. 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 even worse for poor Ayla over the Christmas vacation 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. Hilarity Ensues, 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...
- 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.
- The Lion King has Timon and Pumbaa providing a diversion.
- 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.
- In The Fairly OddParents Timmy is forced into cleaning Vicky's room while dressed in a maid costume.
- Spongebob's uniform when Squidward is living in his house.
- In Teen Titans, Cyborg's initiation to Hive Academy involves wearing a dress in the halls, among other things.
- 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.
- 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.
- In an Episode of the 1994 Cartoon Series, Baby Huey, The Father of Huey 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 blonde 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. https://www.youtube.com/results?search_query=baby+huey+eggs
- Not necessarily dragged since she volunteered to do it, but Anna Popplewell, who portrays Susan Pevensie in that film and its sequels, did one shot for the film adaptation of The Lion, the Witch, and the Wardrobe in the role of Edmund Pevensie when both Skandar Keynes and his regular double were unavailable for that shot, which the producers wanted to get in before the end of the day.
- Robert Pattinson 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.