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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.

This may result in awkwardness for all concerned. The sex-changed character will often examine her new form and find it to be very... attractive. Only to promptly Squick herself out when she realizes what she's thinking. Attractive Bent-Gender operates in tandem with the First Law of Gender-Bending to leave the world more attractive than it had been before. Or at least no less attractive. A handsome man may become a beautiful woman... but so will an unattractive man. In true Gender Bender or Easy Sex Change situations, one rarely encounters a handsome man who becomes an unattractive woman.

The trope may also apply to scenarios where a male is Disguised in Drag or crossdressing. Sometimes this is played straight, but (particularly when the crossdressing is Played for Laughs) it's often a case of Informed Attractiveness. 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 Hilarity Ensues as the crossdressed hero tries to fend off the advances of an unwanted suitor. In more recent works, a hero who is Camp Gay may instead be delighted with the attention "she" is getting, and exploit the opportunity to fool around a bit, with no less hilarious results. For maximum Dramatic Irony in this case, the admirer is not unlikely to be some sort of Heteronormative Crusader. Either way, sooner or later, an Unsettling Gender Reveal is likely to follow.

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Of course, there's nothing stopping this trope from showing up when a female becomes male as well, it's just less common due to this sort of change being rarer overall. However, when it so happens that a woman falls for a Bifauxnen, she will only give up when the disguise is revealed or, these days, is liable to not care.

This trope is often a major part of how the Second Law of Gender-Bending operates. Compare Transgender Fetishization, for which this is usually a Required Secondary Power, where an attractive crossdressing or gender-bending character really enjoys his feminine attractiveness and sexiness, sometimes to excess. Sweet on Polly Oliver is a subtrope where a woman crossdressing is found attractive by straight guys. Frequently accompanies Old Friend, New Gender. See also Rule 63, which basically exists because of this trope. When they actually are both genders, it becomes Everybody Wants the Hermaphrodite.

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Contrary to stereotype, this can be Truth in Television, although it will usually be harder to pull off than in fiction due to the averages of sexual dimorphism in stature, build, facial structure and other such factors between men and women in real life; if a man is pretty when made up as a woman, he is likely also a Pretty Boy to begin with. While many actual Drag Queens could probably be cited as straight (or more usually, gay) examples of the trope, such judgments would necessarily be subjective, as well as prone to attract controversy to the page. Therefore, No Real Life Examples, Please!


In-Universe Examples Only:

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    Advertising 
  • In the '70s or thereabouts, there was a commercial for an electric shaver featuring a cop who needed a really clean shave to pose as a woman for a stakeout. At the end of the ad, another cop studies him and remarks, "Face is terrific!" then grimaces and adds, "But that body!"

    Anime and Manga 
  • In Advance Kitakou Broadcasting Club, Noto gets a huge (male) fanclub when he crossdresses.
  • Ai Ore! Love Me!: Mizuki and her boyfriend Akira . They're androgynous though, so they look the same whatever they're wearing; though Mizuki looks a little overly masculine even when wearing female clothing.
  • D.N.Angel: On one of his many heists, the notorious phantom thief Dark encounters a hot policewoman who succeeds in distracting and capturing him. "She" turns out to be Satoshi Hiwatori — male classmate of Dark's alter ego and the police commander in charge of capturing Dark.
  • Attack on Titan: Apparently, Armin Arlert is good enough of a decoy that he gets some unwanted attention from one of the kidnappers. This is exagerated in Spoof on Titan.
  • Ayakashi Triangle: Matsuri was turned into a girl one day before starting high school, and pretty quickly gets a lot of looks for his large breasts and curvy figure. His still-masculine personality keeps away most of the guys, but their staring and occasional advances are one of the few things he outright hates about being a girl.
  • Baka and Test: Summon the Beasts:
    • Kinoshita Hideyoshi is admired by all straight male cast of the series for his effeminate looks, even though he wears male clothes most of the time. It really doesn't help his case that he is voiced by a woman in all dubs of the anime adaption. That the local bathhouse owners built him his own personal bathing area is a bad sign, too.
      Akihisa: (Seeing the bathhouse sign marked "Hideyoshi") So it's acknowledged by society.
    • Akihisa himself gets this in the OAV. Dressing up as a girl due to a Zany Scheme, "Aki-chan" not only steals the heart of the gay man Kudo but gets voted as "the most popular waitress" of their class with the comment "did we have a girl this cute in our school?". Mutsurini also sold out the "Aki-chan Special Photobook" to ensure massive profits for class 2F in the culture festival.
    • In a Miss Beachside contest, all of the guys were made to crossdress due to the girls. Both Akihisa and Mutsurini scored very well with the male crowd.
  • Black Butler:
    • Ciel Phantomhive, who wore a fancy, pink ballgown. He does make a real cute girl. Well, cute enough that he would get kidnapped by the handsome Viscount Druitt.
    • Alois also dresses up as a female maid and Ciel is shown to look at him in awe because he thinks he's a girl and blush.
  • Bladedance of Elementalers: Kamito was once know as Ren Ashbell, the Strongest Blade Dancer. Approximately 90% of the female world population appears to have been lesbian for him, and most of them still are. He does not find this amusing.
  • Bleach: Subverted when the guys are blackmailed by Rangiku into doing her evil bidding, but don't look good at all, except for Kira, who pulls off the Shrinking Violet look well.
  • Boku to Boku is about two Wholesome Crossdresser's and a bifauxnen girl. In the beach chapter the boys get hit on several times while when the protagonist gets mistaken for a crossdressing boy.
  • Bokura no Hentai: Ryousuke, Satoshi, and Tamura all crossdress for different reasons and pass as attractive girls. Over time they start growing more pubescent and it's noted they have trouble passing as female anymore. Tamura doesn't mind despite his abusive lover dumping him for becoming too masculine, while Satoshi quits crossdressing though Tamura later convinces him to dress up again despite hitting puberty.
  • Cheeky Angel: Megumi Amatsuka is a boy cursed to be a girl by a trickster genie twisted his wish to become a 'man among men' She is generally regarded to be the most attractive girl in the school despite her tendency to inflict violence on her more adamant male admirers. Later subverted when it turns out Megumi always was a girl.
  • CLANNAD: ~After Story~: Shima Katsuki in Misae's arc is forced to crossdress to sneak into the school to see Misae by her friends. The school's males are lovestruck with Moe.
  • Code Geass had this shot from the first season's picture dramas and Bride Luluko. He's considered so pretty in girls' clothing that Milly claims to have lost her self-confidence as a girl upon seeing him in a dress.
  • Cowboy Bebop: 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 call to dress up as a woman, and is considered attractive by both genders. He also temporarily unsettles Faye when she bursts in on him in the shower, sees his breasts (and body), and thinks he's a woman. Then her eyes scroll down.
  • CUTE×GUY: Gren Sumi Takaoko is a generically cute girl who has been turned into a improbably hot, tall man, and promptly gets hit on by just about everyone interested in hot, tall males, especially The Vamp-ish school nurse. She uses it as an opportunity to hang out with the guy she has a crush on as a friend.
  • Daily Lives of High School Boys: Tadakuni is tricked into crossdressing in High School Boys and Skirts. Crossdressed Tadakuni is so hot that his friends wonder "where had the male hormones gone to?"
  • Date A Live: In the second season (quite appropriately called Miku Lily in the light novel title), Shidou was Dragged into Drag in order to get close to Miku Izayoi as she is an idol Spirit that Does Not Like Men. It worked very well, to the point that his cousin alter ego "Itsuka Shiori" becomes her favorite girl very quickly. Doesn't stop Tohka, Origami and Kurumi from seeing through him instantly, though. This is taken further in the twelfth light novel, in which Shidou physically transforms himself into Shiori. There's even a Fanservice colour illustration of Shiori, as for the Spirits in the rest of the series.
  • The Day of Revolution: Megumi, the Gender Bender protagonist. Justified in that she always was a girl (albeit an intersex one) and even the guys wanted him before he Jumped The Gender Barrier.
  • Dr. Stone: An attempt to infiltrate a village's harem results in several of the cast dressing up as women. Senku and Gen look the part perfectly (though Senku's voice is too deep to pass and Gen is too tall to get selected for the harem), while Ginro ends up looking so attractive that he ends up getting selected for the harem even though he's deliberately trying not to be chosen.
  • El-Hazard: The Magnificent World: Makoto looks so much like Princess Fatora, that he can literally pass for her fraternal twin. The resemblance was strong enough to cause Fatora's lesbian lover, Alliel, to mistake him for her at first sight and become sexually aroused. In a later episode, Alliel openly admits that Makoto is the only male who can turn her on, simply because he looks like Fatora.
  • Fushigi Yuugi:
    • The beautiful courtesan Nuriko is revealed to be a man. A very pretty man. (Hotohori, already a gorgeous Bishounen, actually is a little jealous at the start, but to his credit, he can pass off as a lady with little effort.) Later on in the manga, all the Suzaku warriors are temporarily forced to cross-dress, and Chichiri turns himself into a very sweetly gorgeous young woman - possibly the the best-looking out of all of them, to which Nuriko does not react very well.
    • One of the OVA specials features the Suzaku and Seryuu groups and their respective priestesses going on a vacation trip to what turns out to be an all-women's bath (which they find out only when they arrive there), forcing the males to dress as females. It's a no-brainer for Nuriko, while Hotohori is just so bishounen it's no problem for him, and Tomo merely wonders how much make-up needs changing. As for the others, some of them end up looking good, ranging from cute (Chiriko) to gorgeous (Nakago and Chichiri), others end up looking ridiculous (Tamahome and Tasuki), while Mitsukake, who's face was censored, ended up giving everyone a big scare.
  • Gakuen Babysitters has the three caregivers in the Morinomiya daycare dress up as girls in order to fool Kirin's paranoid father. Ryuuichi is the only one to make a convincing and cute girl.
  • Genshiken:
    • In Season 2, Kousaka (who is Stupid Sexy Flanders as is) cosplays as a character from Kujibiki Unbalance for Comi Fes, causing shocked reactions from the other guys from the group.
      Ohno: Do you think it's generally erotic, or just catering to a particular fetish?
      Madarame: I think we should stop talking about this…
    • And there is the Wholesome Crossdresser Hato. Yajima is actually jealous of his feminity.
  • Gintama:
    • Parodied. Gintoki and Katsura end up being forced to work in a crossdressing club after offending the leader of the crossdressers, Fierce God Mademoiselle Saigou. Due to the somewhat bishonen nature of the main characters, they look pretty good. The other crossdressers however are... a bit more realistic.
    • A later story arc has almost everyone in the main cast hit with an actual Gender Bender. Everyone other than Hijikata (Who turns into an overweight Gonk of a girl) and Kagura (Who inexplicably becomes a rugged old man) has good looks, especially Kondo, who doesn't look even remotely similar to how he did as a male.
  • Girl Got Game: Kyo Aizawa, a girl cross-dressing in order to join a high school basketball team makes such an attractive boy that she manages to get more chocolate on Valentine's Day than the team's captain.
  • In Girls Bravo, the main character Yukinari is forced to dress as a girl, in order to host a gaming tournament. His disguise is so convincing that even the local pervert Fukuyama mistakes him for a pretty girl. This makes for one of the most humorous scenes in anime when Fukuyama finds out his true gender.
  • Girls Saurus: Tsubasa is male, but so feminine-looking that people even subconsciously visualise him as a woman (complete with rather ample breasts), and even the main character, who fears all women, keep falling for him in weaker moments... even after the reveal. He goes to an all-male school, but practically everyone else thinks he's a girl in disguise, and has vowed to never reveal 'her' secret since they find the idea of a sweet Polly Oliver romantic. (They don't even peek in the shared showers, so the ruse continues on.) When he finds out, he's thoroughly upset about the whole deal.
  • ½ Prince has Prince, a male in the virtual world and female in real life, so ridiculously good looking that she has a very large fanbase.
  • Hana-Kimi: Lampshaded Subverted near the end when Mizuki (who spends almost all the manga as a Bifauxnen and has to "crossdress back" in certain key occasions) is discovered by the rest of her classmates, many of them only find The Reveal shocking because they think of Mizuki as just cute and hoped that, if there was really a girl crossdressing in their male school, she must be incredibly gorgeous and sexy.
  • Here is Greenwood: Shun Kusanagi and his little brother look like girls, which is disturbing/amusing/arousing to the general populace of the all-male Greenwood dorm. Various other male characters don drag at different points in the manga (mostly for cultural/sports festivals), and attract various admirers. This is not including the alternative-dimension Cherrywood where everyone male is female.
  • In Heroman, when Joey is forced to cross dress in episode 20 it comes as no surprise that he makes an attractive looking girl. What does come as a surprise is that so does his best friend Psy, after taming his wild shock of hair.
  • In Hetalia: Axis Powers, Italy is captured by the Allies after he hits on a pretty girl, who takes him prisoner. The 'girl' in question is actually a very male France in disguise.
  • Honoo no Alpen Rose: The female lead Jeudi has to cut her hair and crossdress to escape the Count, and a girl named Liesl hits on "him". Then people are unsettled with reveals, much to Liesl's disapppointment. A while later, Liesl confesses to Jeudi that she might be a little infatuated with her still, and laments that Jeudi's not a guy.
  • I My Me! Strawberry Eggs: Hibiki Amasawa really does make a convincing woman, even if it is just to get a job as a Gym Teacher.
  • Kamisama Kiss: When Tomoe is posing as Nanami, the guys at school who didn't previously like Nanami find her suddenly hot and those who already liked her even hotter. It's implied that Tomoe is doing things like increasing Nanami's bust size when disguised as her.
  • Kämpfer: Natsuru gets this. And both genders LOVE HIM/HER!!! Doesn't help that his Gender Bender side is VERY beautiful.
  • Kashimashi: Girl Meets Girl: Hazumu gets a lot more more romantic attention after being transformed from a boy to a girl — mostly notably from other girls. This causes problems with her male best friend who comically is conflicted about his undeniable attraction to her despite the fact he knew her as a boy until the gender switch.
  • Macross Frontier: Main character Alto was a kabuki actor specializing in princess or feminine characters, and is nicknamed "Princess" by his classmate/wingmate Mikhail. He absolutely hates this part of his life, and resents his father for dragging him into the business.
  • Marginal Prince: The boarding school holds a festival each year, and by tradition the newest student has to play the princess. Apparently, Henri was so good at it that he had continue this role the following two years. Unfortunately, he declines this role in the fourth year, the one seen in the series.
  • Maria†Holic: Mariya Shidou is a boy crossdressing, but you'd never guess in a million years. This is endlessly frustrating to Kanako, who's not only a lesbian but fears boys so much they make her break out in hives. She's intensely attracted to Mariya as a girl, and has to keep reminding herself he isn't one.
  • Mahoraba: Shiratori Ryuushi. Tamimi and Momono (who dressed him up in his sleep in the first place) knew he would since he was fairly girlish and were still amazed at "Ryuko". When one of his classmates sees "her" he falls in love and becomes depressed at not being able to see her until Shiratori finds out and takes up the disguise again to say "she's" not available.
  • Midori Days:
    • Kouta falls victim to a female gang who decide to put him in a cute dress. The effect is so striking the entire gang falls in love with him.
    • When Seiji dresses up like a girl to catch a molester on a train, his (male) friend unknowingly hits on him. When the friend later shows off a picture he took on his phone, eats the phone.
  • Minami-ke: Makoto, aka Mako-Chan. You wouldn't think that a hairclip and skirt could turn an average-looking boy into a cute girl.
  • Mint na Bokura: Noel needs only put on a wig to become a dead ringer for his twin sister.
  • Monster: Jan Suk (at least until he realizes that "she" is a homicidal Magnificent Bastard and has just framed him for murder). Though in this case, guys usually consider him attractive even out of the dress.
  • Naruto:
  • Natsume's Book of Friends: In one episode, Natsume briefly gets possessed by a female spirit. Because of that, he begins to exhibit feminine qualities (sometimes seemingly having longer hair), and all of his friends start finding themselves disturbingly attracted to him.
  • In NEEDLESS, the character Cruz is constantly Dragged into Drag and almost the entire cast is attracted to him. Most of the female cast get a Nosebleed looking at him and resident Badass Preacher and hardcore lolicon Adam Blade finds him attractive and doesn't even mind much when he finds out Cruz is a guy. Countless Pantyshots ensue, all with a very tell tale lump
  • In Negima! Magister Negi Magi, an Instant Cosplay Surprise turns Negi into a surprisingly cute fox girl. Ayaka has a Nosebleed when see this.
  • Neon Genesis Evangelion: The Angel Chromosome-XX figure of Tabris shows that Kaworu is an attractive sort, regardless of gender.
  • No. 6: As his local theatre was swift to notice, Nezumi makes a really good-looking woman.
  • No Bra: Yuki easily passes as a girl, to the point where the only cast member who knows the truth is his Unlucky Childhood Friend and roommate Masato. Much to his embarrassment, several of his friends quickly develop crushes on this new "girl" at their school. Made even funnier in that Yuki never actually claims to be a girl (he even tries to explain it, but is ignored), just dresses and acts like one. It doesn't help that he has a very feminine build including what seem to be breasts.
  • Nozomu Nozomi: Nozomu can pass for a girl while crossdressing even before his unexplained gender switch.
  • One Piece: Ivankov. Dear Lord. When Ivankov is a man he is ugly, and barely even human-looking. When he is a woman she is beautiful. Why? Because your painfully forced Designated Girl Fight wouldn't be complete without two attractive girls duking it out! His powers lets him control anything about a person's body, be it himself or anyone else by controlling hormones, so if he wanted to he could probably have changed into an unattractive woman, an attractive man, or a freaking goat. Hell, his power is probably how he has his usual appearance of a vaguely bowling-pin shaped giant. He defeated a man in a fight by turning him both body and mind into that of a woman's.
  • In Only Sense Online, Yun's Digital Avatar in the titular MMORPG is a very beautiful girl, a result of the game system misidentifying his sex and generating a female avatar for him.
  • Ouran High School Host Club: Gender-flipped with Bifauxnen Haruhi Fujioka, who is a Wholesome Crossdresser more or less by accident and forced to stay that way by circumstances beyond her control. "He" proves to be very popular with the ladies... and at least one guy who's not in the know.
  • PandoraHearts:
    • When Oz dresses up as a maid, Gil says he looks "gorgeous" and a male servant of the Barma household seems to approve as well.
    • Gilbert and Break (but especially Gilbert) are quite lovely when the mangaka puts them in pretty pretty dresses in an omake.
  • Penguin Revolution:
    • Ryo is so good at cross-dressing that his female persona "Ryoko" is The Ojou of his school, and widely agreed to be gorgeous. Towards the end of the series, he plays highly successful female roles in a movie and a play (and frets that he's going to have to make his living as an actress instead of as an actor).
    • In volume 5, Yuzuru Narazaki dresses up as a woman for an event held by Peacock and looks good enough to make at least one man very uncomfortable.
  • Persona 4: The Animation, as in the video game, has Naoto Shirogane who wins a beauty pageant and has at least one boy and at least one off-screen girl with a crush on her. Teddie also counts, winning the cross dressing pageant by a landslide.
  • The Pet Girl of Sakurasou: 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.
    "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?"
  • +Anima: 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 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.
  • Pokémon: The Series:
  • Princess Princess: Three bishonen in an all-boys school are chosen to crossdress in order to make up for the lack of girls.
  • Ranma ½:
    • Among the many things that rile Akane up about Ranma is that his girl form has a larger bust than she does. Note that he is already considered handsome as a male.
    • Wholesome Crossdresser Konatsu makes quite a beautiful woman, especially compared to god-awful looking step-family. This is justified by being quite Bishōnen, and the one time he wore male clothes the girls were all over him.
    • Tsubasa, whose normal attire is so convincingly feminine that no one except Ukyo knew he was male until the clothes came off. (Then again, all of his disguises are pretty convincing... at first.)
    • The crossdressing version of this was also subverted when Shinnosuke, his grandfather, Ryoga and male-Ranma try to distract a girl-eating monster by dressing as girls. They all look horrible, at least in part because their outfits are ridiculous.
  • Robotech: Yellow Dancer/Belmont, who once gets mistaken for a woman even while not cross dressing.
  • Romeo X Juliet: Subverted when Genki Girl actress Emilia convinces her friend Odin to crossdress for the Rose Ball and notes that the end result is very pretty... completely unaware that Odin actually is a girl.
  • She's My Knight: When Ichinose and Miyoshi (both guys) are dressed as Cinderella and her stepsister, all the girls think they look cute (they think Mogami looks cute all the time, whether she's dressed as a prince or not).
  • Shimoneta: Gouriki is initially antagonistic toward Tanukichi, simply because he's the son of a known "ero-terrorist". But his attitude changes in episode 3, when he sees Tanukichi disguised as a girlnote , which causes Gouriki to develop a full-blown crush on him. The feeling isn't mutual.
  • Slayers: Every season has a crossdressing episode (and it's always episode 17). Gourry looks very attractive - men (and lesbians) hit on him, and in Slayers Try a sea monster mistakes him for a beautiful princess. There's Zelgadis ("Miss Lulu") on episode 17 of Slayers Next. His friends just stare at him for a few seconds, he just looks so damn hot.
  • 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 falls in love with 'her' and doesn't take the subsequent questioning of her sexuality very well...
  • Steins;Gate: Ruka. He's even called "more girly than any girl, more feminine than any female" by Okabe. Even when he actually becomes a she using a text message, there's no way to tell the difference.
  • Sword Art Online: Kirito gets stuck with an extremely feminine avatar in Gun Gale Online. In this form, he is described as having long black hair, crimson lips, and shining black eyes fringed by long eyelashes.
  • To Love Ru: Rito is changed into a girl on multiple occasions by one of Lala inventions, with his best male friend apparently suffering a case of love at first sight. He does make a pretty cute girl.
  • In Tokyo Ghoul : Re, an investigation into a human trafficking ring prompts several cases of Disguised in Drag. Sasaki and Juuzou are both stunning while in disguise.
  • Tokyo Godfathers has a few drag queen characters, most notably Hana, but none of them are conventionally all that attractive. However, Mario, the hispanic assassin character, is introduced dressed quite convincingly in disguise as a pretty waitress.
  • Urusei Yatsura: 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.
  • Usotsuki Lily: Played with. En Shinohara is a male, man-hating Wholesome Crossdresser. He's cute enough that the male student body actually doesn't believe he's male until his uniform blouse gets wet and transparent. However, this doesn't completely remove the problem, as at least one guy afterward is quoted as saying "Even those he's a guy, cute things are cute! (His transparent shirt was erotic!)"
  • Vandread: Taken to an extreme when 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. Ho Yay indeed.
  • W Juliet: Both lead characters. Ito is often cast as the (handsome & manly) male lead in the school plays and Makoto is being forced to pass as a woman in a bet with his father. When Makoto joins the drama club, he often ends up as the female lead.
  • Wandering Son: When Riku dresses up as a maid for a school festival, he's noted to be attractive. Fumika crossdresses to attract the attention of a girl she likes, who likes feminine boys and is attracted to the transgender protagonist, and likes to flaunt his cuteness around.
  • The World God Only Knows:
    • Not only does Keima have the charm and looks to seduce and make the targeted girl fall in love with him, he can make random passerbys comment what a cute "girl" he is when he was dressed as a girl. This is what he looks like as a girl.
    • Also Yui, who prefers to wear boy's clothes after her capture by Keima.
  • WORKING!!: Souta is forced to cross-dress during a few episodes. "Kotori" is not only highly attractive but a huge hit with the girls and guys alike.
  • Yubisaki Milk Tea's main character Yoshinori Ikeda sorts through his coming of age issues by cross dressing. His best friend falls for him, and one of his love interests starts out only being comfortable around him when he's in drag.
  • Yuureitou:
    • When Bishōnen Tetsuo is forced to dress as a woman he makes a very attractive woman. It helps that he lived as a woman for most of his life and was a beautiful, if eccentric, one.
    • Zigzagged with Amano. He has to pretend to be a woman for a sum of the series. He's not ugly at all but not a pretty, feminine doll either. He comes off as homely. It's still pretty noticeable he is crossdressing but no one notices, though he gets called ugly a few times, probably because people crossdressing wasn't well-known in the fifties. Several males take a liking to him, though when boy takes a considerable liking to him Amano notes it is because he lives in a hidden village with almost no young people and has no experience with women.

    Comic Books 
  • Marvel Universe:
    • Marvel 1602: Scotius Summerisle (Cyclops) is in a relationship with Sweet Polly Oliver "John" Grey (Jean) and grows increasingly jealous of the time Werner (Angel) spends with her. Following her death, he realises that Werner never saw through the disguise and apologises. Werner refuses the apology, explaining, "I believed she was a boy, but I was in love with that boy."
    • Thor:
      • Thor has, in some alternate universes, becomes a very beautiful woman.
      • Seeing the sexy female Loki can cause a Stupid Sexy Flanders moment. In this case, as it turned out, it was partly because he was inhabiting the goddess Sif's body, but the trickster god has used shapeshifting and illusion for similar effect on other occasions.
    • The Ultimate Spider-Man version of the "Clone Saga" resulted in a number of clones of Spidey being created. One of Peter's clones, known as Jessica, was female and was meant to have her former memories erased and rewritten with memories suitable for a female secret agent. Jessica escaped before this reprogramming could occur, however. From her perspective, it's as if she had been Peter Parker for her entire life, then suddenly woke up one day as a girl. Hilariously, Jessica had to deal with the fact that Johnny Storm found her attractive, which really freaked out the "original" Peter Parker.
  • In Górsky & Butch, the only female among the main cast in Maciek, a swat policeman re-drawn into a girl while trying to arrest the authors of the comic. He is very attractive, in an Action Girl way.
  • In Batman #626, when Tim Drake disguised himself as nurse Caroline Hill, "she" is almost immediately asked out on a date by someone that has no idea she's Robin, the Boy Wonder.
  • Valhalla: Averted for Laughs when Thor is forced to dress like a woman to infiltrate a Jotun wedding (as the bride). He looks like himself in a dress, with a veil covering the beard. The less said about Loki's initial disguise (which is toned down to the one on the picture), the better.
  • Shade, the Changing Man: When became a woman, she was a stunningly beautiful one. Justified in that he was already such a pretty boy that he had masculinity issues with his image.
  • 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.
  • Youngblood: When Photon switches genders from male to female in the 2012 relaunch, she has quite a few admirers, both male and female.
  • Samurai Jack: In issue 6, 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.
  • Locke & Key: Dodge makes frequent use of the Gender Key to switch between male and female, usually with the intent of seducing someone (or just murdering them). (S)he is equally attractive in either form.
  • In Barracuda, Emilo was a moderately attractive, if slightly fey, boy. After become the Wholesome Crossdresser Emilia, he is a strikingly beautiful young woman.
  • A Titeuf comic start with Titeuf having a dream where he's a girl and Nadia, the girl he love, is a boy, he's still attracted despite this and once a wake up, Nadia makes fun of him and he says to himself that she was cooler as a boy.

    Comic Strips 
  • Beetle Bailey: In one strip, General Halftrack found the company sitting in a clearing watching a beautiful girl in a skimpy bikini parade about. Sergeant Snorkel explained it was a lesson in camouflage: the "girl" was Lieutenant Fuzz. The strip was itself a rehash of an older strip, which had Sarge himself camouflaged as the gorgeous woman.
  • FoxTrot: One arc follows Jason dreaming about waking up as a girl. While Jason is at the age of thinking Girls Have Cooties, Peter points out it could be worse. Cue Jason's best friend Marcus arriving with a bouquet of flowers.

    Fan Works 
  • Gankona, Unnachgiebig, Unità, Hetalia: Axis Powers fanfic, has Germany and Italy definitely think this of Italy when he cosplays as Sailor Moon. Fabric flies within seconds.
  • Neon Genesis Evangelion fan fiction examples:
    • When They're Gone (seen here) features Shinji cross-dressing as a major plot point. He proves to be so attractive when doing this that many of his straight schoolmates begin questioning their sexualities.
    • Another fic consists of a list of things Misato is no longer allowed to do. Most are Noodle Incidents, including a pair of items stating Misato may no longer dress Shinji in girls' clothes, even if he makes it look good.
  • Skin, a Yu-Gi-Oh! fanfic, invokes this trope twice. Besides the fact that one of the otherwise male characters (Namely Seto Freaking Kaiba) has been re-written as a woman. An incredibly attractive young woman who also happens to be crossdressing so well that those who don't know otherwise find her to be an incredibly attractive young man... All as planned.
  • Jade Green Eyes and Beyond Expectations, a Harry Potter fanfic, features Harry crossdressing to hide from the wizarding world after the war ends and he becomes a star. Cue Male Gaze.
  • The Hannah Montana fic "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.
  • Blessing In Disguise: Peter finds that she makes a rather attractive girl after the shock and denial winds down somewhat after being turned into one.
  • In Wammy's House Post-Room, a Death Note crack chatfic, the males think Near looks really good in a dress.
  • Mellorine! Mellorine!: Sanji finds all three of his newly feminine comrades highly attractive, despite not particularly wanting to fawn over them.
  • Monsters In Paradise: A Ditto that had been going around disguised as Utsuho demonstrates its shape-changing ability by transforming into a male version of her. Orin silently admitted that he was easy on the eyes, while Utsuho herself... agreed.
  • Empath: The Luckiest Smurf: In "Another Egg-Citing Day", an adaptation of The Smurfs episode "The Magic Egg", Tapper and Duncan McSmurf are both turned into Smurfettes by Jokey striking the magic egg and teasing them about being Smurfettes for not wishing to use the magic egg. The two gender-bent Smurfs find each other's new forms rather attractive.
  • Evershade: Having gone through a Gender Bender from a guy to a girl, the titular character examines themselves in a mirror, and this trope is noted:
    I looked at my reflection, and found myself taking a moment to examine how it looked.
    [...]
    I was a little nervous to admit it. I look... Pretty. Yeah. I look... Pretty. That was the word I was looking for.
  • Scoob and Shag: When passing himself off as a woman on Earth, Bugs Bunny doesn't skimp on either makeup or nice clothing and is good enough to fool men into hitting on him.
  • An interesting variant in the Code Geass AU fanfic Roomates at Pendragon, where Suzaku is questioning his sexuality in the presence of his roommate Lelouch Lamperouge. The thing is that Lelouch is actually a girl named Leonelle Britannia, having dressed up as a boy to attend the military academy Pendragon.

    Film — Animation 
  • Mulan:
    • During "A Girl Worth Fighting For", Yao teases "Ping" about being a Chick Magnet, and a few farmgirls giggle coquettishly at "him".
      Yao: Bet the local girls thought you were quite the charmer.
    • When Mulan's friends sneak into the palace in disguise. "It's only Concubines." "Ugly concubines," says the second guard. But the first guard seems to have a more favorable opinion.
  • Aladdin: When Iago's impersonating both Jasmine and a female flamingo, another actual male flamingo gets the goo-goo eyes for him, tongue hanging out and everything.
    Iago: YOU GOT A PROBLEM, PINKY?!
  • In The Jungle Book (1967), Baloo's disguise as a female ape is a Paper-Thin Disguise, and he makes no effort to hide his masculine voice, but King Louie is immediately smitten. (The size difference between Baloo and Louie may be a sneaky reference to Louis Prima's song, "The Bigger The Figure")
  • When Robin Hood and Little John are Disguised in Drag as female fortune-tellers, one of Prince John's rhino guards catches sight of the disguised Little John, gets aroused and lets out a wolf-whistle, to which Little John flirts back.

    Film — Live-Action 
  • In Willow, where Madmartigan briefly dresses as a woman after a tryst, pretending to be a cousin of the married woman he just bedded, to avoid being pounded by the lunker of a husband. The husband, after looking him over, offers the immortal line, "Wanna breed?"
  • In Thunderbolt and Lightfoot Jeff Bridges has to dress up like a woman as part of a robbery plot. He looks at himself in the mirror and muses that he looked so good he would do him himself!
  • In The Boondock Saints, FBI agent Paul Smecker dons a dress, and greatly attracts two mafia goons.
  • The Little Rascals: Alfalfa and Spanky in ballerina drags. Bullies Butch and Woim find them quite attractive.
  • 100 Girls: A guy dresses up as a girl to gain access to the girls' dorm at a college and eventually must fend off a rape attempt from a guy.
  • Jupiters Thigh (On a volé la cuisse de Jupiter — "Jupiter's thigh was stolen") is about finding all the lost pieces of Aphrodite of Heracleion statue (an expy of Venus of Milos): torso, pelvis, arms, legs... The torso was a sex symbol for decades, but when restorers finally assemble the statue, it turns out to be male.
  • In White Chicks, 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.
  • In Some Like It Hot, when Jerry is Disguised in Drag as "Daphne," he is pursued by Dirty Old Man 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.
  • In Paddington, the security guard thinks Mr. Brown is very attractive when disguised as a female cleaner.
  • The Hobbit: An Unexpected Journey: 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 ''that one was male.
  • Tootsie: Dustin Hoffman's character is propositioned by one man and nearly assaulted by another while dressed as a woman. Hoffman himself didn't find the makeup work convincing, however. He wanted to be a pretty woman and was told: "this is the best you're gonna get".
  • Tomboy: This is a major plot device. Lisa falls for Mickael who is actually a girl but looks quite boyish. It isn't until the last ten minutes of the film that she learns of the true sex of the object of her affection.
  • The Assignment (2016): Post unwilling sex reassignment, Frank appears in a very attractive female form (played by Michelle Rodriguez in both cases, though the first in makeup obviously).
  • Don Juan De Marco: The main character claims he was forced to hide in a harem for a year, until the sultan saw him dressed as a girl and put the moves on him.Well, it was the young Johnny Depp.
  • Just One of the Guys: Terry Griffith (Joyce Hyser) makes a cute boy who attracts the attention of Sandy (Sherilyn Fenn).
  • Ace Ventura: Pet Detective has a planned case of this. Ray Finkle became Lois Einhorn (Sean Young) because a Fair Cop would go beyond suspicion - even acting seductive and flirty when required - as Finkle exacted his revenge plot.

    Literature 
  • A Series of Unfortunate Events: Plausibly a parody, as the person who finds the Cross Dresser Olaf attractive is himself an unpleasant semi-villain.
  • Mary Russell: Mary is occasionally called upon to dress as a man (given her spouse's occupation, quite frequently) and is still rather Bishōnen doing so. In a situation that might otherwise have been Sweet on Polly Oliver, 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.
  • Jingo: Subverted, as after explaining the "universal law" of this trope, the narration goes on to say that "in this case, the laws were fighting against the fact of Corporal Nobby Nobbs, and gave up."
  • In The Wreck of the Amphidragora, a short story by Naomi Novik, Lady Araminta looks much the same as a man as she did as a woman, which is still fairly attractive. Her captor finds her attractive enough that he would have tried to seduce "Lord Aramin" if Araminta hadn't solicited him first.
  • Arabian Nights: "Prince Camaralzaman and Princess Badoura" tells of a Prince and Princess whose beauty so captivates a pair of djinn that they argue over which is the most beautiful mortal alive. Their attempt to settle the question leads to the Prince and Princess falling in love. It becomes a plot point that the two are almost identical, to the point where the Princess can dress up as the Prince, fool a cohort of her father's guards who are escorting them, and then fool a King and his daughter. Enough that the King proposes marriage and the daughter accepts.
  • The Wheel of Time: The Dark One intentionally gives the formerly male Balthamel a beautiful female body as Aran'gar because Balthamel was a pervert, and the Dark One has a sense of humor.
  • In Lamb: The Gospel According to Biff, Christ's Childhood Pal, there's a scene when Biff has to disguise himself as a woman (he lost a coin toss) to help save the daughter of an Indian outcast, who doesn't let the fact that it's a man stop him from hitting on "her."
  • Rose of the Prophet: 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.
  • Wigfield: This photo, depicting Stephen Colbert as Raven. His brother Jay was completely fooled by the picture, asked Stephen how he knew 'her' and was "a little disturbed" when told he was drooling over his little brother.
  • Steel Beach: Protagonist Hildy Johnson starts out as a fairly standard looking male but, 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.
  • X-Wing Series: In Starfighters of Adumar, the four members of Red Flight have to disguise themselves as women to get past the people hunting them.
    Wes: "So. Who's best-looking in women's dress? I vote for myself."
  • Marîd Audran takes place in the Budayeen, a Red Light District of a 23rd century Cyberpunk Muslim/Arab city. The Easy Sex Change is commonplace, and Attractive Bent Gender is the rule more than the exception. To the point that it's considered noteworthy that one character, a German girl, is exceptionally attractive... despite the fact that she's just a "real girl!"
  • In Orlando: A Biography by Virginia Woolf, Orlando, upon turning into a woman, is amazingly good-looking; she's just as physically fit as she was when she was a man, but has all sorts of feminine beauty on top of that.
  • Leviathan has Deryn/Dylan Sharp, who a number of teenage females in the books (plus Alek) consider extremely handsome, even moreso because she's a heroic airman.
  • Star Trek :"The Procrustean Petard" features a device which changes the sex of every member of the Enterprise crew (except for Spock, whose Half-Human Hybrid nature causes him to suffer from Extra Y, Extra Violent). Kirk is somewhat taken aback by how hot he is as a woman.note 
  • Somewhere Beneath Those Waves: The short story "Amante Doree" features a Transgender protagonist, Annabel St. Clair, who impersonates a woman convincingly enough to establish herself as a notorious courtesan in 19th-century New Orleans. Only her clients and maid are in on the secret, until she falls in love with a man who believes she's a woman.
  • The Stainless Steel Rat: Happens to the protagonist in The Stainless Steel Rat Wants You, when he dresses up to infiltrate an army of invading Starfish Aliens. The joke being Jim is disguised as a hideous bug-eyed monster who is regarded as incredibly sexy by all the other aliens he meets. He puts one admirer off by saying he's a hermaphrodite who is still halfway from he to she.
  • In his Mémoires, General Thiébault relates how he dressed as a girl for a theatrical play he performed on his mother's birthday when he was about twelve. He looked so much like a pretty girl in her late teens that his mother could not recognise him... and when he went out for a walk with this attire, he was followed around by enamoured gendarmes.
  • Loyal Enemies: Invoked. When Shelena and Veres ready themselves to confront the virgin-eating basilisk terrorizing the dwarves, Veres magicks himself a whole-body disguise as a woman. Shelena can't decide whether to be appalled or disgusted about the size of certain assets Veres gives himself, but Veres is confident to be hot as hell. And he proves to be right when they are confronted by a thug who's so distracted by the aforementioned assets he completely disregards how Veres never bothers to change his voice.
  • Princess Holy Aura: Justified in that, since Steve's body was made over completely into Holly, there was no "normal" female form for her to revert to when not fighting supernatural evil—so Holly's default female appearance was Holy Aura's idealized purple-haired perfection, until Holly insisted Silvertail tweak it down to more normal-human looks.
  • In L'Astrée, by Honore D'Urfe, the shepherd Céladon ends up spending quite a bit of time disguised as "Alexis" after his failed suicide attempt and the disguise is so convincing he gets hit on by men who knew him before his "death". His old girlfriend also falls for "her".
  • The Arts of Dark and Light has a villainous example that is not at all played for laughs. Scaum-Durna uses creepy magic to appear as an attractive woman and lure men.
  • The Saga of Tuck does this straight (if you pardon the expression) and deadly serious — it causes Tuck to panic when Travis starts showing serious interest in him, out of fear of what Travis would do if he found out, and later, when s/he reluctantly begins dating him, the realization that s/he is attracted to him. Travis later reveals that a mutual friend had spilled the beans before they started seeing each other regularly (mostly; Travis believes at first that Tuck has had sex-reassignment surgery, which is believable because, as they determine later, Tuck is biologically intersexed).
  • Whateley Universe: Most main characters, as the majority of "changelings" possess the Exemplar trait, which alters the mutant in ways which reflects something in their psyche. This usually, but not always, results in a Heroic Build to match their idealized self-image — meaning that a transgender exemplar gets the sex that matches their gender.

    Live-Action TV 
  • Blackadder:
    • An extreme example, to the point of parody, is the scene in Blackadder II where Lord Percy falls for Baldrick in a dress— despite him retaining his usual beard and level of cleanliness.
    • Baldrick in a dress also works for Lord Flasheart (the beard gives him "something to hang on to!")
    • Bob's "Bob" was a very attractive woman who dressed as such an attractive man that Blackadder falls in love before even finding out that Bob is a woman, shortly after admitting that he had feelings for him.
    • Blackadder Goes Forth: Parodied when General Melchett falls for the square-jawed, Perma Stubbled "Georgina". Taken to insane extremes when he sees "Bob" in a pretty dress and assumes it's a tawdry drag act (Which "Georgina" was intended to be all along).
  • Due South Season 2 Episode 12 "Some Like It Red", Benton Fraser volunteers to go undercover to an all-girls school, requiring him to crossdress. Even the girls at the all-girl school are amazed that "Ms. Fraser" is a man, deciding that "he" must be a woman on the inside, at least.
  • The Dukes of Hazzard: The Season 6 episode "Targets: Daisy and Lulu" have — as part of an attempt to throw the episode's Villains of the Week off Daisy and Lulu's trail, since they are in possession of a stolen necklace the crooks have lost and are attempting to recover — the series defacto bad guys, Boss Hogg and Rosco, try to disguise themselves as Lulu and Daisy, respectively. The trick actually is subverted; they are uglier than their counterparts, but it's played up for full comic value by their portrayers, Sorrell Booke and James Best.
  • NewsRadio: In the Halloween Episode, Dave Foley is said to look better in Lisa's dress than Lisa does. This scenario is an Actor Allusion to when Foley was the most convincing member of The Kids in the Hall to play female characters.
  • Saved by the Bell:
    • In the original series' S:1-E:2, "Screech's Girl", Zack tries to cheer up Screech, who feels depressed because he doesn't think any girl could love him, by claiming he could find Screech a girl. Since he can't he then claims to have found a girl, but that she's very shy. He calls Screech every day and talks to him as "Bambi". Eventually, Screech gets frustrated at not being able to meet Bambi face to face, so Zack is forced to dress up as Bambi and go on a date with Screech to the Max. He does it so well that not only is Screech convinced, but Slater hits on him, realises that it's Zack then compliments his legs. Even Kelly is convinced. Finally, Screech decides that he's better off now, knowing that he's able to date women, but claims not to be ready for commitment yet.
    • In Saved By the Bell: The New Class S:1-E:2, "The Slumber Party", new main character Scott dresses up as a girl so that he can attend a slumber party with his female friends. However, a jock from school catches sight of him and is immediately smitten.
  • Australian comic actor Chris Lilley of Summer Heights High and Angry Boys fame certainly has moments of this when dressed as Lovable Alpha Bitch Ja'mie King.
  • Happy Days: One episode has the Fonz unknowingly take a liking to a cross-dressing Richie. They slow dance.
  • Ned's Declassified School Survival Guide: Cookie ends up crossdressing in several episodes and is hit on by boys in two of those instances. When he disguises himself as "Simone" for the first time, Loomer falls for "her" and is heartbroken when she "leaves" to supposedly go back to Washington. Another time, Cookie crossdresses to get into Seth's Basement Bash, and at one point falls into Coconut Head's arms, who has also fallen for "Simone."
  • The Mighty Boosh: Vince Noir ("the great confuser") from is a prime example, though not everyone is smitten. One character refers to him as "Howard Moon['s]...ugly girlfriend." This becomes part of a running gag in which Vince is often referred to as Howard's wife or girlfriend. Believe it or not, Vince isn't the Butt-Monkey of the show.
  • Rab C. Nesbitt: Davina has a quite large fanbase.
  • Doctor Who: 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.
  • Jeeves and Wooster: In the TV series, Jeeves has to dress up as a female American novelist for one of their Zany Schemes. D'Arcy Cheesewright falls in love with him and moves to New York in order to find her again.
  • Barney Miller: Cops sometimes have to go undercover, resulting in this:
    • Detective Harris is a snappy dresser. When he is assigned to do undercover work wearing women's drag, he spends the whole show getting ready, even shaving off his 'stash. In the end, everyone is stunned at how great he looks as a woman.
    • In another episode, the much less attractive Fish does the same undercover detail and gains a male admirer who continues to be drawn to Fish even after he finds out he's not a lady.
    • Massively averted with Dietrich, who was gung-ho about undercover work, but just ended up looking like a man in a dress.
  • Cory in the House: In one episode, Cory disguises himself as Raven to present new uniforms for the White House. Upon meeting "Raven", Newt thinks he has found Love at First Sight.
  • Lalola: The main character turns into a beautiful woman as the result of a curse, but he was an attractive playboy to begin with. Still, he has to learn to deal with the extra unwanted attention his new body brings.
  • In Silver Spoons, Rick dresses as a girl so that his best friend wouldn't be embarrassed by not having a date to a party. Ricky Schroeder actually made a pretty good looking girl.
  • Boy Meets World:
    • "Chick Like Me" (the title refers to the book "Black Like Me" which inspired the episode) featured a crossdressing Rider Strong, who looked quite fetching as "Veronica Wasboysky". This was commented on in the show and was genuinely true. Cory, who was originally going to be the crossdresser is definitely not an example. It may be more understandable than most examples since Shawn admits to having thought about crossdressing before this ever became a plot. He even has a preferred female name, has practised female mannerisms and has a wig already.
    • "What A Drag!": Jack is supposed to be considered, in-universe, an attractive girl and Eric, in-universe, is definitely not but Jack is clearly a boy in a dress, while Eric looks like just a larger than average girl. This may be because Jack is squeamish about pretending to be a woman and over-compensates, as Shawn tries to explain at the end. Eric, on the other hand, asks for and listens to Shawn's expert advice, implying that Shawn never stopped being Veronica from time to time.
  • Are You Being Served?: One episode has Mr. Humphries dressing in drag for a store beauty contest. Not only did "she" win, but Mr. Grace asked "her" to accompany him on a cruise on his yacht! Mr. Humphries looked horrified as he was dragged away, and the viewer was left to imagine the hilarity that no doubt ensued.
  • The Suite Life of Zack and Cody: A few episodes has either Zack and/or Cody in a dress, and they do look pretty convincing.
  • Sonny with a Chance: When Sonny disguises herself as a male fan named Eric, Tawni is passionately smitten and starts hitting on "him", even organizing a disco ball and dressing fancy and everything. After The Reveal, Tawni didn't care that she was unknowingly hitting on Sonny rather annoyed that Sonny now knows that Tawni finds her better than she thought she was.
  • In 30 Rock, Tracy disguises himself, badly, as a woman, then asks Frank if he finds him attractive. Frank replies, "Tracy, I know it's you...yes, yes I do."
  • While in Monty Python's Flying Circus, one of the Pythons crossdressing for a skit is fairly obvious and played for laughs, Eric Idle actually looks pretty attractive. For example...
  • Scrubs has played with this occasionally with Turk and J.D.: "You'd make a pretty girl."
  • Legend of the Seeker: In "Princess", Zedd dresses up as a prim and proper elderly countess and gets hit on by an elderly herald. The exchange between him and Cara makes the situation even more hilarious:
    Cara: It seems you have an admirer.
    Zedd: [Indignantly] Is there any reason why I shouldn't?
  • Crossdress Paradise features cute high school boys in drag, and has a segment where they must "pass" in public and flirt with passersby. On the other hand, the intended audience for the show is clearly young women.
  • In Wizards of Waverly Place Uncle Kelbo is Shakira.
  • Three's Company: Every time Jack Tripper dressed up as a woman, men fell in love with him.
  • The Devil to Pay in the Backlands: The Mini Series adaptation has a really good example of the female-to-male kind, with the protagonist's love interest Diadorim.
  • The Monkees has two examples:
    • 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. Hilarity Ensues. Mrs. Arcadian's attractiveness is questionable in absolute terms, but the father finds her to be rather fetching.
    • In "Some Like It Lukewarm" (the title being a direct reference to Some Like It Hot), Davy dresses as a girl so the boys can enter a contest for mixed gender groups. He looks like, well, Davy Jones in a dress. However, the radio personality emceeing the contest thinks he's the most gorgeous woman he's ever laid eyes on.
  • Criminal Minds: The killer in an episode. As a split personality killer where one personality is a woman, this was going to happen at some point. And boy, does it happen.
  • The A-Team: In a fourth season episode, Murdock, with help from special guest Boy George, dresses as a pregnant woman to gain access to the rest of the team who have had to barricade themselves in the sheriff's office. Not only does he managed to convince a lynch mob to let him through without anyone questioning that he wasn't a she, but Face mentions that Murdock looked better to him as a woman than he did as a man.
  • F Troop: Done when Corporal Agarn, dressed as an "Indian maid", coaxes the Loco Brothers out of their cave. Made funnier by the fact that Wrangler Jane, an actual woman, had failed in an earlier bid to do the same. Made famous to younger viewers as the clip shown on Freakazoid!.
  • Star Trek: Deep Space Nine:
    • 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 cosmetic procedure.
    Brunt (pointing at naked gender-swapped Quark): I tell you, that is not a female!
    Nilva: Close enough for me...
    • At the start of the series, Sisko discovers that "Old Man" Curzon Dax who was his mentor for many years, is now the attractive Jadzia Dax, due to the Trill having a symbiote who carries their memories to a new host body. Odo speculates that he's interested in her romantically, and Sisko does end up sleeping with an Alternate Self of Jadzia in the Mirror Universe.
  • Wingin' It: The main character Carl is turned into quite an attractive girl in order to understand women, after taking his new Angel in Training girlfriend Denise out on a terrible date. part 1 part 2
  • My Babysitter's a Vampire: In "Three Cheers for Evil", Benny and Ethan must dress up as cheerleaders "Betty" and "Veronica" in order to keep an eye on members of the squad they suspect are up to no good. They use the opportunity to try and get into the girls' locker room, are part of an all-girl sleepover and pillow fight, and are hit on by one of the supporting male characters while in disguise. They definitely make quite cute girls.
  • The Red Green Show: In one episode, the gang has to make it seem like there are women at the lodge, so Harold and Dalton disguise themselves as women. Despite not looking feminine, Harold is asked out on a date.
  • My Name Is Earl:
    • Averted in an episode where, in an attempt to lift a fellow inmate's spirits, Earl signs him up for a dating service provided by the prison. Earl signs himself up, too. Sometime later, Earl and Frank receive their matches. Frank is matched up with a Troubled, but Cute blonde girl, and Earl is matched up with a painfully-obvious pre-op transgender woman named Annie. Earl is very disappointed.
    • Played straight for Black Comedy in another episode, also involving Frank. In an attempt to escape, he disguised himself as a prison nurse. The other inmates either found him so attractive (or were so desperate) that...things didn't go as Frank planned.
  • Charmed (1998): In one episode, a succubus is attacking the men of San Francisco through a video dating service. The Charmed Ones cast a spell to lure her to them to vanquish her, but the spell ends up turning Prue into a man (since the succubus is attacking men.) Deciding to go with it, Prue, now calling herself "Manny," submits a tape to the service, and gets 20 dates lined up pretty quick. Apparently, Shannen Doherty as a man works.
  • 'Allo 'Allo!: Very common. Almost every character — both male and female — wings up in drag at some point, and when the men do it they almost always get hit on both by straight men who don't know and by gay men who do. Particularly common with General Von Klinkerhoffen, who seems to fancy both butch women and cross-dressing men. This reaches a peak at the end of season three. With most of the cast trapped in a POW camp, they all dress up as a chorus line for the prisoner talent show as part of an escape attempt. The Germans clearly fancy not only the men dressed as women but also Edith, Michelle, Yvette and Maria pretending to be men pretending to be women, complete with fake mustaches.
  • Get Smart featured several male spies that passed themselves off as attractive women (usually actually played by attractive women [dubbed a deep masculine voice). In a "would you believe" discussion of an enemy spy who did this, Max eventually confesses that he didn't realize until their third date.
  • In Kamen Rider W, to lure out a MOTW, the Riders have Wakana announce that she's going to a building and catch him there. However, since they can't get Wakana in danger, they have Philip dress as her instead. He actually manages to fool nearly everyone, confusing Akiko because Philip looks really good as a woman and they didn't choose her.
  • In The Drew Carey Show the gang hangs out at a bar with Drew's Wholesome Cross Dresser brother Steve. Kate thinks a man is sending her a drink, but he turns out to be a Chubby Chaser buying a drink for Steve:
    Drunk: Sorry, honey, I like a girl with a little meat on her.
    Kate: Careful what you wish for.
  • Orphan Black: Tatiana Maslany plays so many different clones that it's only a matter of time before they busted out a transgender clone — and he's acknowledged as being pretty hot in-story.
  • In Broad City, Ilana finds Glenn Close as Albert Nobbs extremely hot.
  • In one episode of The Munsters Herman of all people gets hit with this. 'Hermina' gets a job as a cocktail waitress and complains about having to deal with lecherous drunks. Note that 'Hermina' looks like Herman save for longer hair and big breasts and Herman looks like Frankenstein's Monster.

    Music 
  • Vocaloid: Len makes a really pretty girl as seen here.
  • UTAU: Namine Ritsu, one of the better known voicebanks, is male... not that you could tell from most of his songs, fan art, or MMD models, where he makes quite the cute girl.
  • The glam rock band Angel consisted of five guys that looked like ladies. Punky Meadows, in particular, was subject to this from the perspective of Terry Bozzio in Frank Zappa's song "Punky's Whips".
  • The narrator of "Lesbian" by Nuclear Bubble Wrap thinks he'd look good as a woman.
  • Andrew W.K.: The cover art for the album Mother of Mankind features the famous partier in a subtle addition to his normal look, namely lipstick and mascara.
  • Rammstein's drummer, Christoph Schneider, donned a skirt and blouse, complete with make-up, for their video for "Mein Teil". The result was... surprisingly attractive. The band also did a photoshoot in drag, proving that the rhythm guitarist and bassist also both make pretty good-looking women.

    Mythology and Religion 
  • Beti-Pahuin Mythology: The fearsome immortal warrior king Akoma Mba was transformed into a beautiful woman with the aid of his aunt Eyaga’s ghost. Every man was infatuated with rule 63 Akoma Mba, having no clue who this mystery woman was. They hounded for “her” hand in marriage but “she” would only claim to have eyes for the warlord Abo Mama who had singlehandedly vanquished Akoma Mba’s nigh invulnerable army of giant immortal warrior sorcerers. Akoma Mba was able to make Abo Mama fall in love at first sight and learn the secret of the scepter which made Abo Mama so powerful, using his low guard to defeat him. Mind you Akoma Mba in his normal state is a tall, bald, muscular, large eared, tattooed, sharp toothed, and scarred gentlemen who has killed thousands in his time.
  • Norse Mythology has some interesting examples:
    • The gods Odin and Thor have been able to pass themselves off as women. While the fact that Thor and Odin make attractive women may make one wonder what the hell women looked like in the Northlands, Thor's disguise as a woman makes a lot of sense, when you look at the symbolism behind the story. The Jotun steal his hammer and hide it. As the price for returning it, they want Freyja in exchange. She is none too pleased by the Aesir's willingness to sell her down the river for Thor's hammer. The hammer is more than just a hammer, and so, with his *ahem* giant-bashing stick taken away, Thor is metaphorically a woman. Interesting guys, the old Norse. (Yes, this does mean the hammer is his penis.)
    • Thor pulled it off only by hiding his face with a veil, and Loki had to talk fast to explain away his completely unwomanly appetite and fierce eyes.
    • The Norse Trickster God Loki has shape-shifted and not just passed as female, but given birth. To a horse. With eight legs. No, really. He and the other Norse gods had to lure away a horse to keep a wall from being built on time, and Loki was "it." (Certainly, there are few legends in mythology more aggressively Squick-y than Sleipnir's origin story. We feel bad for Sleipnir's dad.)
  • In Hindu Mythology, Vishnu's female incarnation as the enchantress Mohini is so gorgeous Shiva falls for her. They even had a child, the culture-hero Ayyappan, and in some versions, this was their way around a No Man of Woman Born clause.
  • In Classical Mythology, before he was the trope maker for Blind Seer, Tiresias was cursed to become a woman for a year and a day after he whacked some mating snakes with a stick. During this time, he became a very famous and successful prostitute, and was called on to settle Zeus and Hera's dispute about whether men or women enjoy sex more, since he'd experienced both.

    Radio 
  • The Jack Benny Program: In the October 12, 1941 episode, Jack's appearance as a girl was enough to fool Dennis and get him a touch infatuated.
    Dennis Day: You know, I saw Charley's Aunt this summer, and somebody just told me that pretty lady in it was you!
    Jack Benny: Oh, well, i-it was me! It was me, it was my character in the picture. And now ladies and gentlemen—
    Dennis: Holy smoke! You know, I thought it was a real girl!
    Jack: No. No, Dennis, it was me. And um... and now, ladies and gentlemen—
    Dennis: I sent you a love letter. Forget about it.
  • In The Men from the Ministry Mr. Lamb becomes one when he is forced to pose as a receptionist in the episode "Thoroughly Modern Ministry". Several civil servants bring him gifts like chocolate and roses, and Sir Gregory even tries to seduce "Raquel" at the end of the day and is only stopped in his advances because he'll have to leave to meet his wife.

    Theater 
  • Shakespeare:
    • Sometimes it works both ways. When Viola dresses up as a man in Twelfth Night, the woman she's supposed to woo for her lord instead falls for her male persona. (Good thing she has a Half Identical Twin.)
    • As You Like It: And let us not forget fair Rosalind, who once did dress to become Ganymede. A shepherdess, Phebe, then fell for "him", and Rosalind did try to rebuff her.
    • There is a musical adaptation of Twelfth Night called All Shook Up. The music is all Elvis Presley all the time. And lots of attractive gender-bending.
    • In The Taming of the Shrew, the man who finally manages to woo the eponymous shrew(ish woman) is a crossdresser. His relative attractiveness as a man or a woman is not mentioned, but usually, the part is played as either comically manly even when crossdressing or fitting this trope to the point of fake Les Yay between the romantic leads.
  • La Cage aux folles features Les Cagelles, roughly 7 to 16 showgirls most, if not, all of which who are actually men often described by many viewers in-universe as "gorgeous".
  • In Der Rosenkavalier, the Baron von Ochs starts hitting on the chambermaid "Mariandel" the moment he first sees her. When they have arranged a tête à tête, he suddenly notices the resemblance between her and Octavian, whom he has every reason to hate at that point, but dismisses it. And after the tête à tête turns into a trap and the situation culminates in the Baron scandalously abrogating his impending Arranged Marriage to Sophie, he turns to "Mariandel" proposing marriage, whereupon the maid excuses herself with a very amusing secret to tell the Inspector.

    Video Games 
  • Final Fantasy VII: Cloud, if you get the right items for the preceding quest. Although the polycount is too low to allow the player to judge for themselves, he is treated as if he were a very attractive woman in-game. Final Fantasy VII Remake, being in full modern HD, makes it more obvious just how pretty Cloud is for a man, so of course he also makes a very pretty lady. Even though he does not disguise his voice, Cloud's appearance is still feminine enough that many characters do not see through the disguise. Even Tifa does not realize who he is when she first encounters him in a dress.
  • Onmyōji: Tamamo-no-Mae plays this both ways – he's a Historical Gender Flip to begin with, and his in-universe female disguise is as attractive as his real appearance.
  • Samurai Warriors: Mori Ranmaru, a male historical figure, looks like a girl and is even voiced by a woman, which makes the quote he makes upon seeing you in Warriors Orochi, "I am as dangerous as I am manly!" rather amusing in itself. In addition to that, in Samurai Warriors 2, during Oichi's Dream stage, he will eventually join the battle to decide who the most beautiful woman in Japan is.
  • Darkstalkers: Dimitri Maximov has a super move called "Midnight Bliss", which changes attractive (or even unattractive) male or female characters into attractive females. His appearance in SNK vs Capcom: Chaos spawned a fanart industry consisting of female versions of male video game characters, who are referred to as being "Midnight Blissed". Spoofed in a Capcom Fighting Evolution hentai doujin where Dimitri uses the move on Hauzer from Red Earth, which turns the Tyrannosaurus rex into... a Tyrannosaurus rex in a Sailor Fuku with Gag Boobs. Cue a Squicked-out Dimitri backing away at full speed.
  • Persona:
    • Persona 2: Innocent Sin: Jun Kurosu, who is rather androgynous-looking. His official profile states that crossdressing is one of his talents and that he looks prettier in a dress than most girls. In addition, one of his demon negotiation contacts is a group contact with Lisa Silverman, one of the other party members, who ambushes him and puts makeup on him...and then proceeds to get very depressed over him being prettier then she is.
    • Persona 4: There's a lot of this going on. Naoto is pretty attractive as a guy, and later on, Teddie handily wins a crossdressing competition.
  • Majin Tensei II: Spiral Nemesis: BEELZEBUB, of all things, shows up looking like an attractive woman in bondage gear with a fly motif.
  • Circuits Edge, the 1989 CRPG based on George Alec Effinger's Marîd Audran novels (see Literature, above), likewise featured this trope.
  • Sly Cooper: Thieves in Time:
    • In one mission, you're required to steal one of Madame Geisha's dresses for Murray. However, the cables holding the hippo snap, causing him to fall into the dress, and alert the guards. However, the guards mistake Murray for Geisha, and he then proceeds to dance for them to maintain his cover. It works, as all the guards drool over "her".
    • It gets even weirder in a later mission. Sly and Bentley are trying to convince Carmelita to dress in a belly dancer outfit to distract a different group of guards. Throughout the cutscene, you can hear Murray earnestly trying to convince them that he can do the job instead, insisting that he can fit in the outfit. He is ignored.
  • Rakenzarn Tales: During an optional cutscene, Piccolo is trying to convince Daffy Duck, Ed and Eddy to behave more professionally, using Kanon as an example. Daffy begs to differ, citing Kanon's crossdressing incident, complete with a picture of it in which he looks a lot like Reimu Hakurei. Kyuu (jokingly?) comments that Kanon looks kinda hot.
  • The Legend of Zelda: Breath of the Wild: Gerudo Town only allows women (and Gorons) in. Link has to wear traditional Gerudo clothes to get into the town and, being already something of a Bishōnen Long-Haired Pretty Boy, cuts a rather feminine figure in them. Several NPCs comment on his attractiveness when he's disguised as a girl — quite a few guys try to hit on him, in fact — and talking to one lovestruck NPC while wearing the Gerudo outfit unlocks side-quests to obtain the Sand Boots and the Snow Boots.
  • StarTropics has a scenario similar to the one from Breath of the Wild, where our hero Mike has to disguise himself as a girl to enter Shecola. After changing back into his normal clothes, a man outside says that he was "very cute".
  • Chrono Trigger: Flea is stated to be an attractive woman, before Frog states that Flea's not a woman and Flea replies that "Power is beautiful and I have the power!"
  • Red Dead Redemption II: Played for Laughs when the Gadfly French artist Charles Châtenay flees town Disguised in Dragvery obvious drag. He gets a fair few admiring comments from people before they get close enough to notice. Being who he is, he eggs them on, to his armed escort's mingled exasperation and amusement.
  • In Ensemble Stars!, all members of the Theatre Club get a high-rarity card of them in a gorgeous period princess dress, and each pull it off very well. Contrast Souma and Keito playing Ugly Stepsisters in their performance of Cinderella, where neither really bothers to change their appearance at all beyond putting on a dress and so just kind of look normal. When Hajime (reluctantly) dresses as a girl in Love Comedy, he is also said to be very beautiful and passes completely, though the audience never gets to see it. In fact, it's often commented that Hajime would make an extremely cute girl, but he's not interested in cross-dressing so he doesn't really like that.

    Visual Novels 
  • In Little Busters!, all the girls agreed that when Riki was Dragged into Drag, he looked very, very cute. He even successfully passed as a girl to a girl who came to the door to complain they were being too loud.
  • Kira-Kira: Poor, poor Shika. He's forced into drag once in tenth grade and was so cute that a guy fell in love with him. His childhood friend brings this up to their fellow (female) bandmates, who decide to get out his wig and force him to dress up as a girl. Much hilarity is had. Shika swears never to crossdress again—but then he has to dress up as a girl to get into a friend's house because of her overprotective grandfather. And Kirari continues to force him into drag for concerts and her general amusement. One thing leads to another, and Shika spends about a third of the game forced into women's clothing and a wig. Even in the sequel, for the return of the original d2b, his fellow ex-band members conspire against him to crossdress once more for their last performance.
  • In Hatoful Boyfriend and spinoff material, Ryouta Kawara has a job at a maid cafe to support his ailing mother. In the manga, he specifically takes pride in being the most popular waitress there. In a drama CD, he coaxes Sakuya into trying it too, saying it's easy because pigeons like themselves don't have discernible differences between males and females.
  • In Harvest December the girls dress up Madoi, the god of a neighboring area, in a girl's gym uniform. This causes one of the main characters in instantly propose and nearly assault him!
  • In Gakuen Saimin Reido, Akira Aihara was a very handsome and somewhat androgynous-looking high school student. His bullying target, Satou Futoshi, saw Akira as an enemy and managed to take revenge on him by hypnotizing him into crossdressing, adopting a feminine personality, and having an interest in men. The transformation turned out to be marvelous: students at the school were stunned by his beauty as they were unaware of his true identity, and some praised him to be better-looking than the most beautiful girl at the school (who, ironically, had been being courted by Akira when he was still straight). Eventually, even Satou gave in his action of vengeance and fell for Akira (by then Akira has become a transgender woman and changed her name to Shouko).
  • In The Great Ace Attorney, Herlock Sholmes's suite has a picture on the fireplace mantle of a beautiful woman which Susato assumes to be Irene Adler. Should you examine the fireplace on the second day of the fifth case, and Iris will tell Ryunosuke who it really is.
    Ryunosuke: Mr. Sholmes... dresses in women's clothes?
    Iris: Yes. You see the lady in the photographic print on the mantlepiece? That's Hurley!

    Webcomics 
  • Chaos Attack: Doah Lee looks so good dressed up as a girl that the otherwise lazy and uncaring, but still 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. Hilarity Ensues.
  • El Goonish Shive plays with this a lot.
  • Narbonic: :
    • Subverted: Dave's female form is just plain dumpy. ("Aren't women normally shaped more like Jennifer Lopez?" "Despite what you've been taught, no.")
    • But his gaming friend Seth asks him out anyway. Despite knowing that it's really Dave.
      Dave: I wish I could say this was my worst date ever. I totally do.
    • Gender-bent Helen, on the other hand, looks pretty damn good. And the gender-swap formula apparently features in a Mad Science-assisted sex marathon after Dave and Helen become the Official Couple, so girl-Dave can't have been that hard on the eyes.
  • Skin Horse: One of the main characters is Tip, cross-dressing psychiatrist and army veteran. He's also an infamous Casanova, and early in the comic is said to be capable of seducing "any human female under the age of eighty." Later that is amended to "anyone at all."
    Dr. Lee: We were talking, you were very charming, somehow we decided to go to dinner—
    Tip: The rest is just a matter of self-confidence.
    Dr. Lee: No! This is not what I do! I do not sleep with random transvestites!
    Tip: Really? Those clothes on the floor kind of seem to suggest otherwise.
    Dr. Lee: Arrgh... and you were wearing sexier underwear than me...
    Tip: Where do you think I got the self-confidence?
  • Sparkling Generation Valkyrie Yuuki has this as its premise, basically. When Yuuki gets his first good look at his new female body (which has the same face as his old one) he chides himself for his perverted thoughts. And then...
  • The Order of the Stick: Subverted when Roy puts on the Belt of Gender-Changing, as she's still a bald, muscular warrior and very similar to his default appearance. Played straight when donning a (mop) wig is enough to get a dwarf assassin to invite himher back to his room. Subverted again when Belkar can smell that the woman is Roy but hits on him just because it makes him uncomfortable. Given that it's a dwarf that he seduces, it's not really played straight even that once... dwarven women are pretty manly to begin with. A human male may well be more feminine than a dwarven female!
  • Misfile: Ash has managed to attract both boys and girls (not surprising, considering her mother's a lingerie model) but can't quite deal with the squick factor.
  • Bruno the Bandit: Subverted in a story arc where a sorceress' curse turns Bruno, the Bruce Campbell-esque title character, into an equally Bruce Campbell-esque woman. Subverted again when a minor character shows up looking to propose marriage to his ladylove Octavia, who looks exactly as Bruno looks now.
  • In 8-Bit Theater, the airship of the Light Warriors crashes on a female barracks, and to get out of them without being slaughtered by the elves, the LW dress themselves as women. And one of the elf guards finds one of them cute — the one with the obscured face (which would actually drive him insane if he ever actually saw), which his comrades usually mention is smelly and fat, Black Mage (and we didn't even mention his personality).
  • The Dragon Doctors:
    • Mori, a woman who gets turned into a very handsome man, much to the discomfort of his/her recently gender-swapped, formerly-male colleagues. Mori's colleagues are also fairly good looking, but not extremely attractive like him/her.
    • When Aki gets turned into a man, she's likewise a total hunk.
  • Material Girl: Noah's supernaturally-forced crossdressing is played for fanservice in the side material, but earns him several unwanted admirers in the comic itself.
  • Ménage à 3 and its spin-off, Sticky Dilly Buns: Camp Gay actor Dillon frequently dresses in drag, at one point playing Black Canary on stage. He's so convincing that the male actor playing Green Lantern may not realize the truth even after kissing him. It's generally acknowledged by other characters (including straight males) that, yes, Dillon makes an attractive woman.
  • It's Walky!: The "Anomalie" storyline has Joyce and Walky swap genders. Joe, thinking that "Walkie" is one of the "frozen natives," grabs her ass. Tony mistakes her for Sal (which considering that they're Half-Identical Twins, is understandable). When everything returns to normal, Robin reveals that she wanted to kiss "Jayce".
  • Keychain of Creation: Reversing the usual genders of the trope, Marena, a 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.
  • Jet Dream: Appears frequently in Remix Comic stories:
    • The men of the Thunderbird Squadron were all transformed into attractive women, but they were mostly attractive men beforehand. The exception is the former T-Bird "teen mascot," Rolf Jarl Cook. As a boy, he was a short, skinny kid with glasses, but as a T-Girl renamed "Cookie Jarr," she's extremely attractive, to the point that Even the Girls Want Her.
    • Also enforced in the Cookie Jarr stories that feature Teen Superspy organization J.E.T. T.E.E.N. The crossdressing young Elle-Boys are all quite beautiful and have very feminine figures, regardless of what they might look like in their male guises.
  • TwoKinds: In a side plot, the slave Mike has an illusion cast upon him that makes him appear as an attractive female to himself and others. Chaos ensues.
  • DOUBLE K: Simon has spent all but two panels dressed in drag, and several people in-universe apparently find his disguise attractive. And some out of universe as well.
  • In Murry And Lewy, both of the main characters get a Gender Bender. Murry, who was a slightly attractive guy, turned into one heck of a good looking lady, while his partner was average looking at best in both states.
  • In Sinfest, Androgynique.
  • Buck Godot: Zap Gun for Hire: When the titular character — a Heavy Worlder with Stout Strength, nearly as wide as he is tall —- drinks a Klegdixal bio-engineering-something-or-other and briefly turns into a woman (after first turning into a checkerboard, green-and-spotty, and subsequently black) — the woman he turns into is quite hot, and certainly seems to be thoroughly violating the Rule of Conservation — her mass is obviously less than half of Buck's normal. It is unclear whether female Hoffmanites normally look like that since we never SEE any, or if his shapeliness is simply a result of whatever biotech was in that drink. Evidence in the comic suggests it was part of the drink. Buck makes it quite clear that he feels absolutely no attraction to Madame Louisa Dem Five, a super-gorgeous human Hooker with a Heart of Gold, because she looks nothing like a female Hoffmanite, at one point commenting she'd need to gain at least another 250 kilos before he'd be attracted. Even when she starts blasting out her sexual pheromones, while they are able to induce instant arousal in Buck, he's able to hold himself back and even claim she's only just turning him down.
  • Roommates: After Jareth turns himself and some other guys female through Power Incontinence, they ell end up built like supermodels. It was already established before this incident that at least James looks good in female clothing. Thanks to a time manipulating "friend" and later to a French girlfriend and way too much absinthe.
  • DAR!: One strip is based around the idea that "transmen are ridiculously hot". It's worth clicking on the link to see how she has since learned to be more respectful to trans* people.
  • In RAIN, both Rain herself (a transgirl) and Rudy (who sometimes cross-dresses) get a lot of attention.
  • In Scandinavia and the World, Denmark asks Thailand if he could buy 'the sexy lady' a cocktail, but Thailand admits he's Brother Thailand, not Sister Thailand. After a *Beat*, Denmark just asks if that means he'd rather have a beer.
  • this short comic by plays straight at the start when the one of two friends turns into a beautiful girl after eating a magic hotel mint. Then it's defied when the second friend tries to become a hot girl the same way. Only to find out that it might have changed her gender, but it didn't make her any less overweight.
  • Dear Children: Cailin Carver, a tall blonde teenage transgirl, is attractive to the audience (she's a cute and lovable Cloud Cuckoolander Genki Girl), playing the trope straight, but this is averted in-universe — while she presents adequately enough as female, and people like her well enough, she doesn't seem to impress anybody as sexually-attractive.
  • When I Woke Up I Became A Bagel Girl: Bong Gi used to be an obese otaku. One day later, and…well… (In Korean slang, "bagel girl" means "a young lady who has a baby face but a slammin’ curvy body").

    Web Original 
  • Gaia Online: One minigame features a Bizarro Universe in which the Handsome Lech Liam is a Lia instead. She has a bombshell body, but her face is still very plainly Liam's (albeit with a ton of makeup plastered on), both playing this trope straight and averting it.
  • Paradise: An unknown cause is changing humans into Funny Animals (and sometimes changing their gender at the same time), and it's explicitly stated in some of the stories that the gender-Changed get a special "bonus" in the attractiveness department (especially as regards Breast Expansion), even beyond the ordinary such enhancements that Changed get in general.
  • Metamor Keep: 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.
  • A Very Potter Musical:
    • 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.
  • The Spoony Experiment: "Spoonette" seems to be rather popular with the boys. Doubly so when Noah cosplayed as Yuna for his Final Fantasy X-2 review.
  • Vaguely Recalling JoJo: Inverted. Rubber Soul disguises himself as an ugly, fat female who happens to share the same face as his normal form. Jotaro thinks that the Rubber Soul is just an old lady until Yoshikage Kira's dog was devoured by Yellow Temperance.
  • Taco-Man's parody of Night Trap has him disguised as a girl to investigate a case of teenage girls disappearing at a Slumber Party. While there, he catches the eye of the hostess' brother, Zach.
  • Yandere High School has Sam and Taurtis dressing up as "Samantha" and "Taurissa", both of whom catch Dom's attention. Their reason for doing so is Sam's crush on Sookie. Sookie is a lesbian, and the disguise works on her.
  • The Nostalgia Critic: Crossdressing is Doug's Author Appeal, so Tamara and Malcolm dress up as other genders constantly. Lampshaded in the Jupiter Ascending review when Tamara says they all enjoy it.

    Western Animation 
  • Alvin and the Chipmunks did a Sherlock Holmes spoof where Simon played Sherlock, Theodore played Dr. Watson and Alvin played Moriarty. In one scene, Holmes (Simon) disguises himself as a Cockney bar wench and was able to fool Watson (Theodore) enough that he came on to him. Because there isn't enough subtext in that relationship already, chipmunks or otherwise.
  • The Amazing Chan and the Chan Clan: Stanley Chan makes quite a convincing lady when he needs to play the part, and in episode 3 one man found his hula girl self so attractive he proposed to "her"!
  • The Amazing World of Gumball: Parodied when Gumball wears his mother's wedding dress to school after his Bumbling Dad shrunk all his clothes in the wash, and not only does everyone including his brother and father find him impossibly beautiful despite him not changing his voice or mannerisms at all, they think the same of anything wearing the dress, including a balloon with a face scribbled on it and a fire hydrant. Apparently, it was just a really nice dress. (Given they live in a world where animals and objects spontaneously become intelligent, clothes may really be the only thing they can use as a standard of beauty.)
  • American Dad!: Roger Smith apparently looks so good disguised as a teenage girl even his old friend Steve is fooled. They even dated for a while and he never even tumbled to the truth.
  • Beavis and Butt-Head: In one video sequence, Beavis mistakes well-known drag artist RuPaul for a "hot chick", much to Butt-head's amusement.
  • Bugs Bunny: Bugs frequently cross-dresses as part of his Karmic Trickster hijinks:
    • In the classic cartoons, Bugs' "victim" invariably regards the result as attractive, although it looks rather silly to the audience. 'Cause everyone agrees it's funny.
    • Referenced in Wayne's World where Garth asks Wayne if he ever found Bugs Bunny attractive when he dressed up as a girl bunny. Wayne laughs his "no" incredulously for a moment, then says seriously "No", to which Garth hastily responds "Me neither, I was just wondering".
    • Discussed in a Basic Instructions strip, with one character squicking out another by pointing out that none of the female characters in the Classic Disney Shorts (Minnie, Daisy, Clarabelle) is as attractive as Bugs Bunny in drag. The other character requests Brain Bleach but nonetheless admits that this is true.
    • Set up similarly, but subverted in Duck Dodgers, where Dodgers dresses a woman to fool some guards but they both think "she" is ugly and quite easily figure him out to be a guy. Dodgers then has to simply bribe them. (But played straight in an episode where the Cadet is disguised as a female alien to seduce X-2 and retrieve information.)
    • Bugs's drag act is subverted on The Looney Tunes Show. Most characters say he makes an ugly woman, though Daffy and Speedy have found him attractive.
  • Camp Lazlo: The guy-dresses-as-woman variant has happened to Lumpus a couple of times. The first time, after leaving a restaurant without paying, he and Slinkman must sneak back in dressed as women. Sure enough, an employee falls for Lumpus even after he bangs on the men's room door, shouting in his normal voice for Lazlo to let him in. It was done hilariously later on in the series, when Jane, the love of his life, was engaged to the most disgusting character on the series. Lumpus happens to be in a dress when he finally confesses his love for her...and everyone thinks he's a lady confessing her love for Jane's fiance, who simply says, "Sorry, Jane, she's hot," and chases Lumpus.
  • Clarence: The title character is considered to be this when he tries on a bikini in "Clarence Gets a Girlfriend."
  • Clone High: In one episode Joan disguises herself as a man (and by that we mean she wears a fake mustache and uses a clearly fake name) in order to infiltrate the boys' basketball team. Cleopatra comes onto Joan and is shocked when she is rejected (and intrigued when she finds out why) while JFK is so attracted to her that he starts to wonder if she's his Closet Key.
  • Code Monkeys: Mary becomes "Mitch" after she gets fed up with discrimination in "Just One of the Gamers". Just like the Futurama example, a man who lusted after her as a woman (in this case, Jerry), is just as attracted when she's a man, with predictable confusion and self-doubt on Jerry's part.
  • Count Duckula: When Duckula attends a dinner party disguised as a Southern Belle, his enemy Dr. Von Goosewing is immediately smitten with him.
  • In Cybersix, the title character is a woman who dresses as a man in her secret identity, an English teacher, and has a female student lusting after him/her.
  • The Fairly OddParents:
    • In "The Boy Who Would Be Queen", Wanda changes Timmy into a girl. Timmy's best friend A.J. falls for "Timantha" and tries to win her over with a dead frog.
    • Timmy's dad once dressed as a woman to enter Miss Dimmsdale pageant. Adam West falls in love with him and knowing the truth does nothing to change the feeling.
  • Family Guy: Brian has hit on both a Disguised in Drag Stewie and Quagmire's father.
  • The Flintstones: There are at least two episodes where Fred dresses as a woman, and in both someone inexplicably finds him irresistibly attractive. (Well, inexplicably if you discount "because it complicates the plot" as a viable reason.)
  • Futurama:
    • Played with in "War Is the H-Word", when Leela disguises herself as a decidedly un-handsome man named "Lee Lemon." Even though she doesn't look like much, Zapp Brannigan is strangely attracted to "him" and, in the end, after fighting Lee, losing, and finding out who "he" really is, proclaims that he's never been so happy to have been beaten up by a woman.
    • In "Bend Her", Bender passes himself off as a female robot to enter the Robot Olympics and attracts the attention of Show Within a Show actor Calculon. Fridge Logic ensues.
    • In "Neutopia", most of the cast have their genders swapped by an alien. Most of the crew don't look great, but as a female, Fry not only quickly attracts the attention of Zapp but is sufficiently good-looking to effortlessly slip into the Brainless Beauty trope.
      Female Fry: Now when I say stupid things guys laugh and buy me stuff!
  • The Garfield Show: One episode has this happening to Garfield and Odie, resulting in them looking like elderly ladies (to be fair, though, this is imposed on them). Nermal gets smitten the moment he sees Garfield in this fashion, but lucky for him he never finds out the truth.
  • Johnny Bravo:
    • In "The Sensitive Male!", Johnny's idea of getting in touch with his feminine side involves dressing as a woman. Not only does this get him laughed at by the woman he's trying to flirt with, but then two lonely sailors on shore leave start flirting with Johnny.
    • Justified in "Witch-ay Woman", when a gypsy enchantress turns Johnny into a woman. She specifically turns him into an attractive woman so he can learn how annoying it is to be constantly hit on.
  • Kaeloo: In one episode, Stumpy tries to enter a nightclub, but the bouncer tells him that only girls are allowed. He comes back in a wig pretending to be a girl, and the bouncer seems to find the "girl" attractive.
  • My Little Pony: Friendship Is Magic: In "Brotherhooves Social", Big Macintosh disguises himself as a mare in an attempt to participate in the Sisterhooves Social. Nopony is fooled and they decide to humor him, except for one middle-aged stallion who hilariously tried to court him and gave him flowers.
  • Pinky and the Brain: In "My Feldmans, My Friends", Pinky and Brain disguise themselves as a married couple to fool the neighbor, who falls for Pinky as Mrs. Feldman.
  • The Powerpuff Girls: Professor Utonium's Coincidental Accidental Disguise as a female lumpkin makes Fuzzy fall madly in love.
  • Rugrats: A G-rated version occurs when Tommy is crossdressed as a girl by Stu and Lou to enter him in a beauty pageant. The audience and the judges all think he's adorable, including Angelica, who calls him "The cutest little girl (other than herself) in the pageant". He even ends up winning the pageant until they're ratted out by Didi.
  • The Simpsons:
    • In "Marge in Chains," Bart plans to use this trope against the prison warden.
    • In "Cape Feare", Abe developed feminine attributes due to not taking his medication. Jasper Beardley then flirted with "her". Abe would have told the truth but changed his mind when his suitor told "her" his dating plans.
    • In "Kiss Kiss, Bang Bangalore", there's a Stargate SG-1 convention. When the lights are out, MacGyver-obsessed fans Selma and Patty abduct Richard Dean Anderson. The people attending the convention conclude that there must be a real Stargate in the convention hall, and start looking for it until someone points out something more incredible: there's a girl in there. The "girl" is Groundskeeper Willy, who tries to explain he isn't a girl and is wearing a kilt but is told he's the best they hope to get.
  • South Park:
    • Parodied. After deciding he's a woman trapped in a man's body, Mr. Garrison undergoes sex reassignment surgery and (briefly) becomes "Janet" Garrison. The female Garrison looks nearly identical to the male version, save for lopsided breasts and a slightly smaller build.
    • "Cow Days": Cartman suffers a case of amnesia and believes himself to be a Vietnamese prostitute named "Ming Lee". Wanting money, his friends have "Ming Lee" earn it for him. At least one of the clients likes it so much he doesn't even become upset upon recognizing Cartman is a guy.
    • In "Fat Butt and Pancake Head", Cartman's hand was Jennifer Lopez. She likes tacos and burritos. Ben Affleck left the real Jennifer for the fake, and Cartman, who apparently couldn't control his hand, got Affleck spooge all over him.
    • In the Black Friday trilogy, Kenny becomes the legitimately Animesque Princess Kenny, who makes men fall in love with "her" cuteness just by being there.
  • SpongeBob SquarePants:
    • In one episode, Patrick disguises himself as a woman and becomes part of a Love Triangle between Squidward and Mr. Krabs.
    • Subverted in the episode where Mr. Krabs' daughter Pearl has a birthday party with all her female friends. Mr. Krabs wants to spy on his daughter's party, and SpongeBob offers to help. Cut to what is very obviously SpongeBob in high heels, lipstick, and a dress (without any effort to change Tom Kenny's voice) walking up to the house and ringing the doorbell. The girls open the door for "her", but immediately see through her disguise, say they've never seen "her" before, and demand that SpongeBob leave the party, until "she" runs off in tears, just as Mr. Krabs drives up with the real SpongeBob, not in female clothing. They watch her run away, and wonder where she came from in confusion.
      Mr. Krabs: Who was that girl?
      Spongebob: I have no idea, but she was ugh-ly!
  • Stōked: In "Mr. Wahine", Reef is first forced to dress up like a girl by the senior staff members, but then when he finds out that there's an all-girl surf contest going on, he decides to keep his disguise on for a chance to beat his rival-slash-love interest Fin. Disguised as "Sandy Beaches", he discovers to his horror that the manager of the hotel is immediately crushing on him.
  • Tom and Jerry:
    • One episode features Jerry getting a robot dog to protect him from Tom. Tom hides the robot and disguises himself to look like it. By the time the robot escapes and confronted him, a moped falls into Tom's disguise, making it look like a female dog robot. The robot falls in love.
    • When Tom is tasked with guarding the garden against a gopher, he disguises himself as a female gopher. It would have worked except that Jerry warns the gopher, who then plays along.
    • "Flirty Birdy" (1945): Tom uses a Paper-Thin Disguise to entice an eagle who is also after Jerry for eating. Things Go Horribly Right and it ends with Tom sitting on a nest of eggs!

 
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Alternative Title(s): Bent Genders Are Attractive, Crossdressers Are Attractive, Hotter As The Other Gender

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Cloud dressed up as a girl is so convincing Tifa can't even recognize him at first.

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