History Main / AttractiveBentGender

* LetsPlay/TacoMan's parody of ''VideoGame/NightTrap'' has him disguised as a girl to investigate a case of teenage girls disappearing at a SlumberParty. While there, he catches the eye of the hostess' brother, Zach.

[[folder:Theater]]

* Shakespeare:

* ''Theatre/AVeryPotterMusical'':
** While many people already found Joe Walker attractive when he played Voldemort , many more believed that him playing '''Umbridge''' in ''A Very Potter Sequel'' only made him hotter.
** Lauren Lopez makes a very adorable Draco Malfoy, too. Sango Taijima (usually Lavender) makes a really cute boy.

* ''Literature/MetamorKeep'': A rare justified example -- the transgender curse victims are ''intentionally'' made to be attractive to the opposite sex, and originally it's because they're to be turned into sex slaves.
* ''WebVideo/TheNostalgiaCritic'': Crossdressing is Doug's AuthorAppeal, so Tamara and Malcolm dress up as other genders constantly. Lampshaded in the ''Film/JupiterAscending'' review when Tamara says they all enjoy it.

* The ''Series/HannahMontana'' fic "[[https://www.fanfiction.net/s/5042600/1/From-Tomboy-to-Boy From Toyboy to Boy]]" features a female-to-male version of this; Lilly decides to escape the latest round of bullying by pretending to leave Seaview High and then return under the guise of 'Otis Scott', who immediately attracts the attention of Amber, Ashley and Miley. The situation swiftly becomes more complicated when Miley falls for Otis and Lilly (unable to tell her the truth as Amber and Ashley keep trying to flirt with 'Otis') finds herself responding to Miley's interest, Miley's interest in 'Otis' unintentionally reinforced because Lilly continues to do little things like adjust Miley's hair or compliment her outfits without fully considering how those actions will appear when performed by a boy rather than a girl.

* ''Webcomic/KeychainOfCreation'': Reversing the usual genders of the trope, Marena, a [[AnythingThatMoves happily promiscuous]] shapeshifting Lunar Exalt, is just as attractive when she changes into a male form. Given that the comic is based on the Exalted roleplaying game, and the Lunar shapeshifting power in the game doesn't alter the character's Appearance stat, this is all according to the rules.

* In ''Franchise/{{Batman}}'' #626, when [[ComicBook/RobinSeries Tim Drake]] disguised himself as nurse [[http://i54.photobucket.com/albums/g108/ladymirth/Batman626Pyrate-DCPpg10.jpg Caroline]] [[http://i54.photobucket.com/albums/g108/ladymirth/Batman626Pyrate-DCPpg12.jpg Hill]], "she" is almost immediately asked out on a date by someone that has no idea she's Robin, the ''Boy'' Wonder.

* ''ComicBook/{{Zatanna}}'': Mikey, Zatanna's assistant who can fill out her stage costume quite nicely in a pinch, apparently was once a burly male Teamster type.

* ''Film/TheHobbitAnUnexpectedJourney'': In the extended edition, while resting in Rivendell, Killi remarks that most of the elven girls don't look particularly appealing to him except the one who was running the place when they arrive (since Elrond was off leading the party dealing with the goblins). The other dwarves wait for a minute and then tell him ''[[{{Elfeminate}} that one was male.]]

* ''ComicBook/ShadeTheChangingMan'': When Shade became a woman, she was a stunningly beautiful one. Justified in that he was already such a [[{{Bishonen}} pretty boy]] that he had masculinity issues with his image.

* ''Literature/MaryRussell'': Mary is occasionally called upon to dress as a man (given her spouse's occupation, quite frequently) and is still rather {{bishonen}} doing so. In a situation that might otherwise have been SweetOnPollyOliver, this trope holds truer -- in ''O, Jerusalem'', when she's dressed as a teenage boy, her would-be rapists are in no way dissuaded by her revealing her gender.

** WholesomeCrossdresser Konatsu makes quite a beautiful woman, especially compared to [[{{Gonk}} god-awful looking]] step-family. This is justified by being quite {{bishonen}}, and the one time he wore male clothes the girls were all over him.

* ''Literature/RoseOfTheProphet'': Mathew easily comes off as an extremely beautiful woman while he [[DisguisedInDrag dresses as one]]. Even prior to this he had been [[DudeLooksLikeALady been mistaken for one]].

* ''Literature/RoseOfTheProphet'': Matthew is supposed to be androgynous-verging-on-the-feminine anyway, but damn it's harped on. Then again, the fact that he has to spend most of the story cross-dressing is a big plot point anyway.

* In ''Film/SomeLikeItHot'', when Jerry is DisguisedInDrag as "Daphne," he is pursued by DirtyOldMan Osgood, much to his humiliation. When Jerry is finally forced to reveal himself as a man, due to Osgood's insistence in proposing marriage, Osgood says, "Well, nobody's perfect!"
** He might be humiliated at first but eventually he begins to enjoy being treated like a pretty girl, admires his engagement ring greatly and has to be reminded that he can't really marry Osgood.

* ''Film/VictorVictoria'' is a GenderFlip with a double somersault. Victoria is a woman disguised a the male Victor. As Victor, she gets a lot of female attention. But just to add a layer of confusion, Victor's job is a ''female impersonator'' (a DragQueen, but more respectable) in a 1920s cabaret show.

* ''Anime/{{Vandread}}'': Taken to an extreme when [[spoiler: the titular ship's second-in-command, named BC, is a male, surgically changed into a woman's body and infiltrated into the crew to act as a spy for the males. Does a good enough job (with the aid of a voice-changer) that one of the captured crew, Bart, falls in love with him. The reveal in ''Vandread: Second Stage'' is well-done.]] Even after learning that she's a man, Bart still proclaims his love. It's not very disturbing for Bart to love a cross-dresser, as he lived all his life on a planet populated entirely of men. HoYay indeed.

* ''ComicBook/SamuraiJack'': In issue 6, [[ViolentGlaswegian the Scotsman]] is cursed with the form of a woman by some mischievous leprechauns after he drunkenly barges into their fairy circle. The "Scotswoman" is considerably more pretty and petite than before... much to his shame and embarrassment; the Scotsman doesn't dare go home to his wife trapped in the body of a "no-good stick-thin lassie monster". The Leprechauns cruse Jack too, but female Jack is not that different from Male Jack.

--->'''Ryunosuke:''' Mr. Sholmes... dresses in women's clothes?
--->'''Iris:''' Yes. You see the lady in the photographic print on the mantlepiece? That's Hurley!
--->'''Ryunosuke:''' [[StupidSexyFlanders (... He's quite stunning...)]]

** Mori, a woman who gets turned into a very handsome man, much to the [[StupidSexyFlanders discomfort]] of his/her recently [[GenderBender gender-swapped]], formerly-male colleagues. Mori's colleagues are also fairly good looking, but not extremely attractive like him/her.

The trope may also apply to scenarios where a male is DisguisedInDrag or [[{{Crossdresser}} crossdressing]]. Sometimes this is played straight, but (particularly when the crossdressing is PlayedForLaughs) it's often a case of InformedAttractiveness. In such scenarios, despite the "new woman" perhaps looking mannish and homely to the audience, someone will nevertheless be smitten with "her." Traditionally, this would be where HilarityEnsues as the crossdressed hero tries to fend off the advances of an unwanted suitor. In more recent works, a hero who is CampGay may instead be [[ProudBeauty delighted]] with the attention "she" is getting, and exploit the opportunity to [[TheTease fool around a bit]], with no less hilarious results. For maximum DramaticIrony in this case, the admirer is not unlikely to be some sort of HeteronormativeCrusader. Either way, sooner or later, an UnsettlingGenderReveal is likely to follow.

** In "The Chaperone", when the chaperone for the guys' party passes out drunk right before it starts, Micky does himself up as "Mrs. Arcadian" to appease the father of the girl Davy is in love with. HilarityEnsues. Mrs. Arcadian's attractiveness is questionable in absolute terms, but the father finds her to be rather fetching.

* ''Webcomic/ChaosAttack'': Doah Lee looks so good dressed up as a girl that the otherwise lazy and uncaring, but still [[CastFullOfPrettyBoys incredibly attractive]] leap on the opportunity to save him when he's attacked by an alien monster. Needless to say, they are ''not'' pleased when they find out the truth, and insist that Doah pay them back by working as their manager. HilarityEnsues.

* ''LightNovel/{{Kampfer}}'': Natsuru gets this. And [[EvenTheGirlsWantHer both]] genders LOVE HIM/HER!!! Doesn't help that his GenderBender side is VERY beautiful.

* ''LightNovel/ThePetGirlOfSakurasou'': In the original light novel when Nanami asks Ryuunosuke to wear a waitress outfit, he refuses on the grounds that he would be prettier than her.

* ''Manga/UruseiYatsura'': Ryuunosuke is a girl forced to dress up as a boy. Despite all of the school knowing of her situation, she still gets more Valentine's chocolates and love letters from the girls than all of the other boys.

* ''Film/AceVenturaPetDetective'' has a planned case of this. [[spoiler:Ray Finkle became Lois Einhorn (Creator/SeanYoung) because a FairCop would go beyond suspicion - even acting seductive and flirty when required - as Finkle exacted his revenge plot.]]

* In ''Film/WhiteChicks'', two FBI agents Kevin and Marcus Copeland impersonate female supermodel twins Brittany and Tiffany Wilson whom they were supposed to deliver to a hotel. A billionaire named Litrel Spencer falls madly in love with Marcus and keeps flirting with him throughout the film, much to Marcus' disgust. When he finds out the truth at the end of the film, he is more distraught over Marcus being black than him being male.

* ''St Luminous Mission High School'': The lead male's best friend, Ryuzo Tanami, spends all but maybe fifteen minutes of the series in drag. (Hey, he ''said'' he wanted to attend an all-girl's school...) Not only is "she" very good-looking, with instantly & ''natural'' long hair and no telltales, one of 'her' classmates who thought she was straight [[EvenTheGirlsWantHer falls in love with 'her']] and doesn't take the subsequent questioning of her sexuality very well...

* ''Anime/CowboyBebop'': Gren is a man who suffers from a severe hormone imbalance due to experimental drug treatments and subsequently gained feminine secondary sexual characteristics, including breasts. He occasionally finds a call to dress up as a woman, and is considered attractive by both genders. He also temporarily [[UnsettlingGenderReveal unsettles Faye]] when she [[ShowerOfAwkward bursts in on him in the shower]], sees his breasts (and body), and thinks he's a woman. Then her eyes scroll down.

* ''Literature/HalfPrince'' has Prince, a male in the virtual world and female in real life, so ridiculously good looking that she has a ''very'' large fanbase.

* ''Anime/{{Monster}}'': Jan Suk (at least until he realizes that "she" [[spoiler: is a homicidal MagnificentBastard and has just framed him for murder]]). Though in this case, [[EvenTheGuysWantHim guys usually consider him attractive even out of the dress.]]

* ''Manga/PlusAnima'': At the beginning , Husky is dressed as a Mermaid Princess. Looking back later in the series, Cooro mentions that 'Husky was pretty as the Mermaid Princess.' When Nana knocks Husky out and puts him in a dress, someone (probably Cooro again, since Senri [[SilentBob never talks]]), says that it's pretty. When Husky is bought by Lord Hashas and shows up at his mansion dressed like a black-haired pre-teen girl, he finds 'her' "exquisite", and when Nana and Cooro rescue him from Hashas, Nana coos and fawns over how 'pretty' and 'amazing' he looks. Husky often gets mistaken for a girl even when he ''isn't'' dressed up like one. Nana even believes he's a girl secretly crossdressing as a boy in the beginning.

''Whenever a male is turned into a female (or sometimes just when he dresses as one), he/she will almost always be extremely attractive, especially to members of his inner circle and close associates.''

* In ''Film/{{Paddington}}'', the security guard thinks Mr. Brown is very attractive when disguised as a female cleaner.

* ''Webcomic/{{Misfile}}'': Ash has managed to attract both boys and girls (not surprising, considering her mother's a [[FashionModel lingerie model]]) but can't quite deal with the {{squick}} factor.

* ''Series/DoctorWho'': The Master turns the entire human population into clones of himself, resulting in various disturbingly gorgeous Drag!Masters. The original script even had a cut scene where the original Master flirted with Abigail!Master.
** He eventually regenerated into a female form, and apparently found her VERY attractive. [[IHatePastMe Strangely, the feeling was ''not'' mutual.]]

** In "Profit and Lace", Quark is forced to do a gender-swap and pose as a female. Every male Ferengi he encounters (even his own family) comments on what a lovely female he makes, to the point where the Nagus (who knows he's really Quark) can't keep his hands off him and a prominent businessman is completely smitten with him (even after being told Quark is really male). As it turns out, with Federation medical technology, gender reassignment is an outpatient procedure and is easily reversible.
-->'''Brunt''' (pointing at naked gender-swapped Quark): I tell you, ''that'' is not a female!\\

* In ''Series/WizardsOfWaverlyPlace'' Uncle Kelbo [[spoiler: is Shakira]].

-->"It creeps me out to even think about it, but Kanda's focus will be all on me. Now tell me, would you be fine with that?"

* ''Literature/SteelBeach'': Protagonist Hildy Johnson starts out as a fairly standard looking male but, [[EasySexChange after a high tech sex-change]] (a common motif in Varley's work), becomes a stunning woman. Unlike most examples of this, with Hildy it's intentional -- he/she doesn't care what he looks like as a man but wants to be the most attractive woman she can be.