Attractive Bent Gender

"Jerry: Oh, you don't understand, Osgood! Ehhhh... I'm a man.

Osgood: Well, nobody's perfect."

- Some Like It Hot, 1959

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" looking mannish and homely to the audience and most characters, someone will unaccountably be smitten with "her." Hilarity Ensues as the crossdressed hero tries to fend off the advances of an unwanted suitor.

This trope frequently leads up to the Second Law of Gender Bending. Sweet On Polly Oliver is a subtrope where a woman crossdressing is found attractive by guys. Frequently accompanies Somethings Different About You Now. See also Rule Sixty Three, which basically exists because of this trope. When they actually are both genders, it becomes Everybody Wants the Hermaphrodite.

Contrary to stereotype, this can be Truth in Television.

Advertising

 * In the '70s or thereabouts, there was a commercial for either a razor or 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!" Grimace: "But that body!"

Anime and Manga
"Aoi: So... how do I look?
 * Ranma One Half. 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.
 * Ranma is also one of the only guys turned girls that really didn't get turned on looking at herself naked. When ending up naked in a bathtub with a mirror-generated duplicate, he finds the situation vaguely odd, but not much else. The clone, on the other hand...
 * Ryoga gets distracted by Ranma fairly easily, save for when he and s/he first end up in the bathroom together -- most likely because of Ryoga's sheer rage at Ranma at the time and discovering that Ranma truly was responsible for causing Ryoga to receive his Jusenkyo curse. He's more vulnerable when he's not aware that Ranma is the girl currently almost-naked or flirting with him, but unless things are really serious, he's still not exactly happy at seeing Ranma's girl-form naked.
 * The female form being incredibly attractive is possibly part of the curse as both another person and a monkey affected were equally good-looking. Though, at one point it is mentioned that female Ranma looks almost identical to her Hot Shounen Mom and the other guy was almost undoubtedly Bishonen, so maybe that was just one very good specimen of monkey
 * Oddly enough, apparently Rumiko Takahashi herself also preferred the female Ranma, as she shows up in Fan Service scenes, and "cute" cover art (emphasizing the femininity of the character,) more often than any other character in the series.
 * His/her fanservice role may be due to the fact that he's really a guy, probably making it more morally acceptable to use him that way. Ranma also seems to be less conscious about showing his body, probably due to being male.
 * Takahashi herself said to the animators that she did not want them to use her female characters for Fan Service and panty shots (granted, although girl Ranma gets lots of the former, she never gets the latter).
 * Or possibly she's playing off the tendency of covers to be fanservice and making the audience feel weird about it for humor.
 * Wholesome Crossdresser Konatsu makes quite a beautiful woman, especially compared to god-awful looking step-family. This is justified by being quite Bishonen, and the one time he wore male clothes the girls were all over him.
 * Don't forget about 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.
 * Subverted in Bleach, where 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.
 * Makoto in El-Hazard and El-Hazard 2. He just happens to look exactly like Princess Fatora.
 * Code Geass had.
 * Don't forget.
 * GAH! Stupid sexy Lulu!
 * Jun from Happiness!, a Wholesome Crossdresser who wants to be a girl to marry his (straight male) childhood friend and dresses and acts accordingly. This causes another student to remark on one occasion that "The number one beauty in this school is a guy." At one point, he is actually turned into a girl by wild magic (with very little outward change), which has the side effect of making every male in the school become obsessively attracted to him/her.
 * Ryuunosuke from Urusei Yatsura 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.
 * Subverted in Romeo X Juliet 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.
 * Shiratori Ryuushi of Mahoraba. 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.
 * Persona 4: The Animation has  who wins a beauty pageant and has at least one boy and at least one off screen girl with a crush on her.   also counts, winning the cross dressing pageant by a landslide.
 * Subverted in Macross Frontier: main character Alto was a kabuki actor specializing in princess or feminine characters, and is nicknamed "Princess" by his classmate/wingmate Miguel. He absolutely hates this part of his life, and resents his father for dragging him into the business.
 * He also happens to share Ranma's last name, Saotome; this may be a Shout Out on the producers' part.
 * Given Alto's romantic difficulties, it's very likely to be a Shout Out to both Ranma Saotome as well as the real-life Kabuki stage actor, Taichi Saotome, who played female roles himself.
 * Somewhat Lampshaded and subverted near the end of Hana-Kimi:.
 * Hazumu from Kashimashi Girl Meets Girl gets a lot more more romantic attention after being transformed from a boy to a girl - mostly from other girls too. 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.
 * 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.
 * It doesn't hurt that his voice actor is Mamiko Noto.
 * Taken to a extreme in Vandread, where
 * 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.
 * Haku from Naruto, who is a very attractive girl in all respects save his actual gender. He was able to convince Naruto that he was a girl simply by removing his mask and changing his clothes, and it came as no small shock to Naruto when he discovered the ruse. Some fans choose to ignore the revelation of his gender as nothing more than a lie.
 * Naruto's Sexy/Harem Jutsu has this effect, although this is usually intentional.
 * Gren, from Cowboy Bebop, is a man who suffers from a severe hormone imbalance due to experimental drug treatments and subsequently gained breasts and a female body. 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.
 * Inverted in Ouran High School Host Club, with Bifauxnen Haruhi Fujioka, who is a Wholesome Crossdresser more or less by accident.
 * Also averted in a chapter where the half of the male members of the Host Club dressed up as women and just looked like men in dresses, makeup, and wigs. This is notably surprising in that, had it been any other manga, they would have been gorgeous.
 * That's just because their costumes and makeup were gaudy and ridiculous, otherwise they probably would make pretty good woman.
 * Watch Kyoya in that scene. He's not wearing any ridiculous make-up. He literally looks like a woman. It's the same deal at the end of the Haruhi in Wonderland episode, where he's cross dressing for some reason while the rest of the hosts are dressed as male characters.
 * The Zuka Club.
 * James is no stranger to cross-dressing in Pokémon (so much so that in some fanfic universes it's considered to be part of Team Rocket's basic training), but in an episode that was banned for years in the United States, he enters a women's bikini contest wearing a particularly convincing full-body, flesh-tone bodysuit with inflatable breasts.
 * Ash Ketchum himself has dressed as a girl on three different occasions in the series so far, one of them during the episode Pokemon Scent-sation as Ashley.
 * Every season of Slayers 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. And of course, 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.
 * One wonders if the trend began because of Slayers' Idiosyncratic Episode Naming . Episode 17 was the "Q" episode ("Question?" in this case), and one has to wonder if they were trying to slip "Queer" past the radar in the process.
 * in Monster.
 * And so does Jan Suk (at least until he realizes that "she" ). Though in this case, guys usually consider him attractive even out of the dress.
 * Aoi Futaba from You're Under Arrest. Lampshaded in Episode 5, where the Bokuto squad attempt to "masculinize" him by putting him through martial arts training and dressing him in a male officer's uniform, with unfortunate results.

Ken, Natsumi, Miyuki, Yoriko: (various pained expressions)

Miyuki: He actually looks better in a skirt..."

"Ohno: Do you think it's generally erotic, or just catering to a particular fetish?
 * In CUTExGUY 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 a opportunity to hang out with the guy she has a crush on as a friend.
 * Ryo in Penguin Revolution 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).
 * Likewise, 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.
 * Masashi Rando effortlessly passes as Yuna Kurimi in Pretty Face.
 * Although it's justified since it's not simple crossdressing or gender bending, but.
 * In one episode of Natsume Yuuinchu, 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.
 * Yuki from No Bra 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.
 * Rito from To Love Ru is changed into a girl on four separate occasions, with his best male friend apparently suffering a case of love at first sight. He does make a pretty cute girl.
 * When the title character of Hayate the Combat Butler is accidentally cursed to dress like a girl, he actually looks disturbingly attractive. Attractive enough to convince Izumi's butler that he really is female (he even lies and says his name is Hermione Ayasaki, and the butler lampshades that it sounds like a wizard's name). Then, Izumi recognizes him and tells the butler the truth, which causes him to look at Hayate's chest and realize that she's right. Better yet, he goes from being dressed like a maid to being dressed up like a bunny, and then accidentally reveals himself in public to all of the people he knows.
 * Note that Hayate actually turned said butler, Kotetsu Segawa, completely gay for him. Ever since then he has rather aggressively pursued Hayate, once even challenging him to ping-pong at an onsen resort on the condition that if he won Hayate would have to go into the bath with him (He later threw the match to Maria, who made her condition that the two of them would have to do her chores...dressed as maids. We haven't yet seen this but we have seen Maria excitedly preparing maid outfits for it.)
 * He's been forced to cross-dress numerous times over the course of the manga and so far Nagi, Maria, Isumi, Sakuya, Miki, Risa, Izumi, Chiharu, Ayumu, and Hinagiku have all seen him this way. When Sakuya needed to find a maid she lamented that Hayate was a butler and not a maid, Nagi and Maria (with evil grins) commented that they preferred him as a maid too. Isumi seems to think that cross-dressing is a hobby of his (and doesn't mind at all) while Risa was more than willing to help Maria force him into girl's clothes in Greece. Ayumu and Chiharu were there when Nagi made Hayate wear Ayumu's street clothes and both found him very attractive (Ayumu even told him to keep the outfit because he looked so good in it). Hinagiku admitted that she found him disturbingly attractive as well, but so far has been the only one to prefer as a guy. Shame Hina's mom tried to get the poor guy to wear a frilly dress that Hina wouldn't wear for her within an hour of meeting him.
 * Hell it was literally a plot point that if someone meets him when he is crossdressed they would never be able to tell that Hayate is a guy. And it's been proven twice so far.
 * Wandering Son's Shuuichi Nitori inadvertently stole the attention of the boy his older sister liked after he saw Shuu dressed as a girl.
 * Nitori has quite the harem, from both boys and girls. On the other side of the spectrum, Takatsuki is quite the looker too.
 * Makoto, AKA Mako-chan from Minami Ke. You wouldn't think that a hairclip and skirt could turn an average looking boy into a cute girl.
 * In Mahou Sensei Negima, an Instant Cosplay Surprise turns Negi into a surprisingly cute fox girl.
 * Simiarly, Kouta in Midori Days 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.
 * Not to mention when Seiji dresses up like a girl to catch a molester on a train, prompting his (male) friend to unknowingly hit on him. Said friend later shows off a picture he took on his phone. Seiji responds by eating the phone.
 * Tsubasa from Girls Saurus 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.
 * In Gundam 00 one of the Trinity brothers points out that if Tieria Erde were a woman he would be extremely attractive. Later on Tieria has a somewhat infamous scene in which  The result is so stunning that that some male fans admit they would go for even knowing that he is, in fact, a guy.
 * And the female fans? Many ladies thought and/or said "HOTTEST TRAP EVER, KTHX".
 * And before Tieria there was Loran from Turn a Gundam who spent a great deal of time in drag, and is very attractive even to male fans who knew full well that he is a he.
 * Played with in Mobile Suit Gundam ZZ, where the male members of the Gundam Team have to crossdress to infiltrate a stronghold (It Makes Sense in Context). Iino makes a good-looking girl, but Judau... does not.
 * Mariya Shidou from Maria Holic 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.
 * At the beginning of Plus Anima, 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 said Lord, Nana coos and fawns over how 'pretty' and 'amazing' he looks.
 * Then again, 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.
 * Happens often in 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.
 * Shima Katsuki in Misae's arc in Clannad: ~After Story~ is forced to crossdress to sneak into the school to see Misae by her friends. Needless to say, the school's males are lovestruck with Moe Moe.
 * In Fushigi Yuugi, the beautiful courtesan Nuriko is revealed to be a man. A very pretty man. (Hotohori, already a gorgeous male, actually is a little jealous at the start.) 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. Of course 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.
 * Possibly one of the most amazing instances occurs in St. Luminous Mission High School where the lead male's best friend, Ryuzo Tanami, spends all but maybe 15 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...
 * In Season 2 of Genshiken Kousaka (who is pretty much 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.

Madarame: I think we should stop talking about this..."


 * Ivankov from One Piece. 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!
 * He defeated a man in a fight by turning him both body and mind into that of a woman's.
 * Ivankov's power lets him control anything about a persons 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.
 * 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.
 * Ciel Phantomhive from Black Butler, 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.
 * Yellow Dancer/Belmont from Robotech/GenesisClimberMospeada who once gets mistaken for a woman even while not cross dressing.
 * Ranmaru, Takenaga, and Yuki.
 * Kämpfer: Natsuru gets this. And both genders LOVE HIM/HER!!! Doesn't help that his Gender Bender side is VERY beautiful.
 * Hibiki Amasawa really does make a convincing woman, even if it is just to get a job as a Gym Teacher.
 * Megumi, the Gender Bender protagonist of the The Day of Revolution. Justified in that she always was a girl (albeit an intersexed one) and even the guys wanted him before he Jumped The Gender Barrier.
 * Parodied somewhat in Gintama. 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.
 * Gilbert and Break (but especially Gilbert) are quite lovely when the mangaka puts them in pretty pretty dresses in the Pandora Hearts omake.
 * The Angel Chromosome-XX figure of Tabris from Neon Genesis Evangelion shows that Kaworu is an attractive sort, regardless of gender.
 * Megumi Amatsuka from Tenshi Na Konamaiki (AKA Cheeky Angel) 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.
 * Kinoshita Hideyoshi enjoys a similar status in the fandom as Jun Watarese of Happiness (see above), due to the Ambiguous Gender factor.
 * Yuuji Fukunaga of Liar Game is a male-to-female transsexual. And you'd never believe it if everybody else didn't keep using male pronouns when referring to him.
 * Sora Aoi of Aki Sora. Every girl in his life takes any possible opportunity to make him crossdress, and he looks waaay too cute every single time.
 * Hanaukyo Maid Tai
 * Episode 15. Taro looks very nice in his maid costume.
 * La Verite episode 5. Taro looks quite beautiful in his Mahoromatic cosplay costume.
 * Kyo Aizawa, a girl cross-dressing in order to join a high school basketball team makes such an attractive boy in Girl Got Game that she manages to get more chocolate on Valentine's Day than the Team's captain.
 * In Heroman, when Joey is forced to cross dress in episode 19 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.
 * Hiro gets hit on by a couple of gangsters in the BLAM Episode of Ookami Kakushi.
 * This is the main premise of Princess Princess, where three bishonen in an all boys school are chosen to crossdress in order to make up for the lack of girls.
 * Played with in the manga Usotsuki Lily. 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!)"
 * Pandora Hearts: 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.
 * The five protagonists in Ame Nochi Hare.
 * In Axis Powers Hetalia, 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.
 * Ahem.
 * Examples from 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
 * Mizuki and her boyfriend Akira in Ai Ore Love Me. 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.
 * in the Honoo no Alpen Rose manga.
 * Peppo of Gankutsuou.
 * Tadakuni in Daily Lives of High School Boys was tricked into crossdressing in High School Boys and Skirts. Crossdressed Tadakuni was so hot that his friends wonder "where had the male hormones gone to?"
 * Mizutama in Pump Up, when they dress him as Cinderella for a play.
 * When he was younger the protagonist of Kuroneko Guardian used to model in girl's clothes. He now finds it incredibly embarrassing.

Comic Books

 * An unusual variant in the Marvel Universe Elseworld 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."
 * In Gorsky and 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.
 * When Tim Drake from Batman dressed up like a girl, "she" was almost immediately asked out on a date by someone that had no idea she was Robin, the Boy Wonder.
 * 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 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, and they even started dating, which really freaked out the "original" Peter Parker.
 * Jimmy Olsen, on more than one occasion!
 * Thor has, in some alternate universes, becomes a very beautiful woman.
 * Likewise, 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.
 * In one Beetle Bailey 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.
 * When Shade the Changing Man 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's beautiful assistant Mikey (who can fill out Zatanna's stage costume quite nicely in a pinch) apparently was once a burly male Teamster type.
 * Averted for Laughs in Valhalla, when Thor is forced to dress like a woman to infiltrate a Jotun wedding (as the bride). He looks pretty much like himself in a dress, with a veil covering the beard. And the less said about Loki's initial disguise (which is toned down to the one on the picture), the better.

Fan Fiction
""Right. Do you want to try explaining why they're all built like super-models, on top of being girls?...""
 * This Neon Genesis Evangelion fic 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 consisted of a list of things Misato was 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.
 * In a particularly interesting example, this Yu-Gi-Oh fanfic manages to invoke 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 of course.
 * the Harry Potter fanfic Jade Green Eyes and Beyond Expectations'' feature Harry crossdressing to hide from the wizarding world after the war ends and he becomes a star. Cue Male Gaze.
 * In a Spider Man fanfic 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.
 * As Sarah called out Jareth about it in fancomic Roommates:


 * 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.

Film
"Yao: Bet the local girls thought you were quite the charmer."
 * Leslie Cheung: in various films like this
 * The classic Hollywood version of this trope is Some Like It Hot, whose final lines provide the page quote.
 * Goodbye Charlie has a dead mobster come back to life as the beautiful Debbie Reynolds. In a 1984 failed pilot for a TV series, he's Suzanne Somers.
 * Switch (a loose and unofficial remake of Goodbye Charlie) has Perry King "trading up" to Ellen Barkin.
 * Though it's more a case of a handsome man becoming an attractive woman.
 * in The Crying Game - and, in fact, the actor who plays her - makes a stunningly beautiful woman.
 * Angel from RENT
 * Barry Watson (and some would say Michael Rosenbaum) in Sorority Boys.
 * In Back to The Future Part II, Michael J. Fox plays several of Marty's family members, including his future daughter. He makes a pretty good looking girl.
 * Rare example of a female to male, but in Boys Don't Cry about the real life murder of Brandon Teena, who was a trans man, Hillary Swank not only looked convincingly male, but was not bad-looking.
 * Breakfast On Pluto goes to show that Cillian Murphy makes an awfully pretty girl.
 * Cillian also cross-dresses in the movie Peacock. He is...alluring.
 * Dustin Hoffman as Tootsie. Charles Durning's character said something near the end of the movie to the effect of "The only reason you're still alive is that I never kissed you."
 * Subverted in Victor/Victoria, with the man dressed as a woman actually being a woman dressed as a man dressed as a woman. (and when a man dons one of her outfits, he is certainly not convincingly female.)
 * 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?"
 * This is pretty much the central theme of the film Zerophilia, which centers around a character whose sex changes back and forth several times throughout.
 * Billy Crudup made quite the popular and attractive lady when he played one of the last of the Restoration era boy players Ned Kynaston in Stage Beauty.
 * Stephen Dorff in I Shot Andy Warhol.
 * With all due respect to Calpernia Addams, Lee Pace in Soldier's Girl is much prettier as Calpernia Addams than she is.
 * Tilda Swinton has done this twice:
 * As the title character in Orlando. Orlando starts off as a rather attractive man in Renaissance England when, enamoured by his beauty, Queen Elizabeth I grants him immortality. Roughly 150 years later, Orlando goes into a days-long sleep, only to wake and find himself transformed into a woman.
 * She played the archangel Gabriel in Constantine as a divine, genderless being.
 * 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!
 * The titular character of Mulan has this at times, most notably in "A Girl Worth Fighting For".


 * Dr. Frank N. Furter from The Rocky Horror Picture Show.
 * A female version of this is seen in the Bob Dylan biopic I'm Not There. Cate Blanchett portrays the "electric" Dylan, and looks very good while doing so, gaining quite a female following.
 * Jeffrey Donovan played a crossdressing character in the obscure 1997 thriller Catherine's Grove. He looks pretty fetching as a woman.
 * John Cameron Mitchell as the titular character in Hedwig and The Angry Inch. Even with a good gendar, you have to keep reminding yourself he's a guy.
 * Will Keenan as Casey in Terror Firmer, when it's revealed.
 * The Adventures of Priscilla Queen of the Desert: Guy Pearce.
 * 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
 * In 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.

Literature
"Wes: "So. Who's best-looking in women's dress? I vote for myself.""
 * Mary Russell is occasionally called upon to dress as a man (given her spouse's occupation, quite frequently) and is still rather Bishonen doing so. As can be understood. And in a situation that might otherwise have been Sweet On Polly Oliver, this trope holds truer-- during O, Jerusalem, when she's dressed as a teenage boy, her would-be rapists are in no way dissuaded by her revealing her gender.
 * Subverted in Terry Pratchett's Jingo, where after explaining the 'universal law' of this trope, it goes on to say "In this case, the laws were fighting against the fact of Corporal Nobby Nobbs, and gave up."
 * In Naomi Novik's short story The Wreck of the Amphidragora,  looks much the same as a man as she did as a woman, which is still fairly attractive.
 * Older Than Print: The Arabian Nights story "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.
 * In 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, there's a scene when Biff has to disguise himself as a woman (he lost the coin toss) to help save the daughter of an Indian outcast (widowed) he had just met. Said Indian outcast doesn't let the fact that it's a man stop him from hitting on "her".
 * Matthew (or should I say 'Blossom'?) in The Rose Of The Prophet trilogy. He 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.
 * , depicting Stephen Colbert as Raven from Wigfield. 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.
 * In John Varley's 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.
 * Mentioned in Starfighters of Adumar. The four members of Red Flight have to disguise themselves as women to get past the people hunting them.


 * Averted in Last Call, when the protagonist goes Disguised in Drag to infiltrate a poker game. Justified, as in this case he's only concealing his identity rather than his sex, so it's sufficient that he passes for a drag queen, not a woman.
 * George Alec Effinger's Marid Audran series 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!"
 * 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.
 * The Star Trek short story "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.
 * 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.

Live Action TV
"Cara: It seems you have an admirer.
 * Occurs several times in Black Adder:
 * 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!")
 * Plus, of course, 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.
 * Parodied in Black Adder Goes Forth, 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. He looks quite fetching, with a strong resemblance to Lucy Lawless. 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.
 * In the Halloween episode of News Radio, Dave Foley is said to look better in Lisa's dress than Lisa does. Then again, Foley knew about it as a member of The Kids in The Hall where this was a comedic plot point from time to time...
 * Examples from 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.
 * Something similar happens in a classic episode of Happy Days where the Fonz unknowingly takes a liking to a cross-dressing Richie. They slow dance.
 * Vince Noir ("the great confuser") from The Mighty Boosh 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.
 * Davina has a quite large fanbase.
 * Doctor Who,
 * In Jeeves and Wooster - the TV series, not in the books - 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.
 * Cops on Barney Miller sometimes have to go undercover:
 * Detective Harris (played by Ron Glass) 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.
 * Justified in the Argentinian/Spanish soap opera Lalola. Part of the curse that turns Lalo into Lola is that he has to be an attractive woman - so that he'll know what sexist jerks like himself put attractive women through.
 * 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 Season 4 Episode 15 "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.
 * Boy Meets World Season 7 Episode 11 "What A Drag!" is more debatable. Jack is supposed to be considered, in universe, an attractive girl and Eric, in universe, is definitely not. In actual terms, however, Jack is clearly a boy in a dress, while Eric actually looks like just a larger than average girl. Of course, that may be because Jack is so 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 did stop being Veronica from time to time.
 * One episode of Are You Being Served had 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.
 * A few episodes of The Suite Life of Zack and Cody had either Zack and/or Cody in a dress. And they did look pretty convincing. This example might be considered a surprising allusion for a Disney show to a previous role played by the Sprouse twins in The Heart Is Deceitful Above All Things.
 * In 30Rock, 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."
 * In the Legend of the Seeker episode "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:

Zedd: [Indignantly] Is there any reason why I shouldn't?"

"Brunt (pointing at naked gender swapped Quark): "I tell you, that is not a female!"
 * The Japanese Reality Show Crossdress Paradise (turn on "closed captioning" for subtitles), which features cute high school boys in drag, and has a segment where they must "pass" in public and flirt with passerby. On the other hand, the intended audience for the show is clearly young women.
 * In Wizards of Waverly Place Uncle Kelbo.
 * Every time Jack Tripper dressed up as a woman, men fell in love with him.
 * The Miniseries adaptation of the acclaimed Brazilian book The Devil to Pay In The Backlands has a really good example of the female-to-male kind, with.
 * The Monkees had 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.
 * "Alberta" from He's A Lady.
 * Ru Pauls Drag Race runs on this trope.
 * The killer in an episode of Criminal Minds. As a split personality killer where one personality is a woman, this was going to happen at some point. And boy, does it happen.
 * In a fourth season episode of The A-Team, 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.
 * Done in F Troop 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.
 * In the Star Trek Deep Space Nine episode "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).

Nilva: "Close enough for me…""


 * Ivan a drag king played by Kelly Lynch on The L Word.
 * In Wingin' It, a Canadian Disney show, 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
 * In one episode of The Red Green Show, 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.

Music
"Now I'm not dumb but I can't understand
 * From The Kinks' 1970 comeback hit "Lola":

Why she walked like a woman and talked like a man."


 * Roger Taylor in Queen's I Want To Break Free video.
 * Freddy Mercury has amazing legs. I mean, the mustache is a bit of a turnoff, but damn...
 * In conflict with its public image, Aerosmith's "Dude Looks Like A Lady".
 * In Vocaloid, Len makes a really pretty girl as seen here.
 * The female versions of the male band members in Nightwish's video for "Bye Bye Beautiful".
 * The guys of The Lonely Island have stated that while filming the Jack Sparrow video, they became rather uncomfortable around Michael Bolton while he was dressed as Erin Brockovich.
 * Jo Calderone, Lady Gaga's male alter ego.
 * 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".
 * Topic of the Magnetic Fields' "Andrew in Drag".

Mythology

 * 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, of course, is none too pleased by the Aesir's willingness to sell her down the river for Thor's hammer. The hammer is, of course, 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 Loki has shapeshifted 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.

Radio
"Dennis Day: You know, I saw Charleys Aunt this summer, and somebody just told me that pretty lady in it was you!
 * From the October 12, 1941 episode of The Jack Benny Program:

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."

Theater

 * Shakespeare's entire life's work, pretty much.
 * Sometimes it works both ways, too. 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.
 * The cross-dresser in RENT, Angel.
 * 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.
 * Peter Pan productions in the United Kingdom, including the original concept. Normally, British theatre is known its panto Dames; respectable male actors who perform the role of an older woman in the play, whether the original story had one or not, and perform it as a Drag Queen. But in the Peter Pan productions, they are replaced with an attractive young woman playing the role of the prepubescent boy Peter Pan. This is traditional in honour of the original Peter Pan, who was played by the author's children's Nanny when they first devised the story to entertain the kids while they were bedridden with illness over Christmas.
 * M Butterfly. --especially when played by the right actor.

Video Games

 * Cloud from Final Fantasy VII, 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.
 * Given his character design in the Compilation, it's no longer hard to imagine what Cloud would look like as a woman. Now I just want to know what he'd look like as a man.
 * The answer is something like [[http://genzoman.deviantart.com/art/Manly-Cloud-144852759?q=boost
 * Forget imagination. If Cloud-in-drag looked anything like THIS in the crossdressing sequence of the original FFVII game, it's no wonder Don Corneo decided to pick Cloud instead of Aeris and Tifa.
 * Even when they forgot to include any sort of stuffing for Clouds blouse, which Tifa, and even Aeris, has a-plenty...
 * Maybe he likes Pettankos? He later kidnaps Yuffie...
 * The main character of Final Fantasy XIII, Lightning, is deliberately something of his Distaff Counterpart. She's not just, presumably, similar to him personality wise, she ''[[http://eydx.deviantart.com/art/Lightning-and-cloud-196624020?q=boost
 * To put it bluntly, Lightning is Cloud if / when he cross dresses. Toriyama's guidelines to Nomura was to make her "strong and beautiful" - a "female version of Cloud." And considering, who wouldn't want to bang Cloud when he's dressed like a girl?
 * Bridget from the Guilty Gear series of games, who is the basis of an internet meme for this very reason.
 * Mori Ranmaru is a male figure from Japanese history who is frequently portrayed in fiction as having a very feminine appearance. Particularly in the Samurai Warriors video games, Mori 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.
 * Dimitri Maximov from Darkstalkers 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.
 * Jun Kurosu from Persona 2: Innocent Sin, who is rather androgynous-looking. His official profile states that crossdressing is one of his talents and that he looks prettier in a dress then 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.
 * There's a lot of this going on in Persona 4.  is pretty attractive as a guy, and later on Teddie handily wins a crossdressing competition.
 * Poor, poor Shika in Kira Kira. He was 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.
 * Lucifer Louisa Ferre in Strange Journey.
 * In Majin Tensei II, 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 Marid Audran novels (see Literature, above), likewise featured this trope.
 * Poison from Final Fight is either a post-op or pre-op transsexual, depending on who you ask. Word of God is that she's pre-op in Japan and post-op elsewhere. It's like She's a Man In Japan, but... more complicated depending on personal definitions. In any case, she makes a lovely woman.

Webcomics
""I wish I could say this was my worst date ever. I totally do.""
 * El Goonish Shive plays with this a lot. Tedd's transformation ray actually has a setting designed to turn males into attractive females. It also turns the girls into attractive males. In fact, one of the variations also gives the transformed person enhanced pheromones, or in Tedd's own words, making them "smell sexy". It then subverts the inversion by giving Sarah a male form that is decidedly less hunky -- (though VERY bishounen, making for a possible Double Subversion.) Tedd, meanwhile, looks very feminine even as a boy, to the point that guys (and guys who are turned into girls) feel quite awkward around him.
 * Sarah also falls into the trap of being briefly attracted to herself when she looks in a mirror.
 * And Susan herself gets 'weirded out'' when surrounded by girls in her male form (because one of the side effects of the TFG's gender-swapping settings is heterosexuality in the altered sex).
 * The comic now has a favourite justification: Tedd designs the forms, and he sees no reasons to make more ugly people.
 * Subverted in Narbonic: 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.


 * Charlie from Khaos Komix (though she's a transgirl, not a crossdresser) looks damn hot in a corset and skirt. Even Natalie Geln is jealous.
 * She looked great when she had long hair too. On the other side of the spectrum, Tom (a [[Transsexual female-to-male) is Mr. Fanservice at its finest. And he's not even on hormones.
 * RPG World polled readers to find out which character in the comic would win a swimsuit competition. After the results were tallied, it was revealed that character with the second highest number of votes ("Red Haired NPC Girl") was really just Hero, the lead male character, dressed like a girl.
 * 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...
 * Subverted in Order of the Stick, when Roy puts on the Belt of Gender Changing, she's still bald. Played straight when donning a (mop) wig is enough to get a dwarf assassin to invite him her 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 that a dwarven female!
 * Ash from Misfile 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.
 * Subverted in a story arc of Bruno the Bandit, wherein 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 Eight 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).
 * Subverted/Inverted in The Dragon Doctors with Mori, a woman who gets turned into 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.
 * Basically the entire plot of MaterialGirl; just add unwilling crossdressing. (This example needs some Wiki Magic.)
 * Dillon of Ménage à 3 dresses up as Black Canary for a part in a play. He's so convincing that apparently his male co-actor playing Green Lantern doesn't realise even after kissing him.
 * The "Anomalie" storyline in Its Walky! had 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."
 * Reversing the usual genders of the trope, in Keychain of Creation, Marena, a happily promiscuous shapeshifting Lunar Exalt, is just as attractive when she changes into a male form.
 * Appears frequently in Jet Dream 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.
 * In a side plot of Two Kinds the slave Mike has an illusion cast upon him that makes him appear as an attractive female to himself and others. Chaos ensues.
 * Given the reactions of various characters, Sonja and Robyn seem to fall under this category in The Wotch.
 * Every significant male character of Black Adventures has gotten a crossdressing fanservice scene now.
 * Simon of Double K has spent all but two panels dressed in drag. And apparently, several people in universe 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.

Web Original

 * The online serial novel 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.
 * One of Gaia Online's minigames 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.
 * Most main characters in the Whateley Universe, it's not just the gender benders though: half the mutants who have a physical change when they manifest are extremely attractive while the other half, including two of the protagonist genderbenders, don't look human anymore.
 * In the Paradise setting, in which an unknown cause is changing humans into Funny Animals (and sometimes changing their gender at the same time), it is 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.
 * A rare justified example in Metamor Keep - the Transgender curse victims are intentionally made to be attractive to the opposite sex, and originally, it's because they were to be turned into sex slaves.
 * While many people already found Joe Walker attractive when he played Voldemort in A Very Potter Musical, 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.
 * This is inevitable in any story in the Transsexuals and Crossdressers section of Literotica, for obvious reasons.
 * "Spoonette" seems to be rather popular with the boys....
 * The entire (insulting) point of the "It's a trap!" meme.

Western Animation
"Rooster: I like you, baby! You're different! (drags Sylvester off) You'll be my favorite!"
 * The Fairly Odd Parents, "The Boy Who Would Be Queen": Wanda changes Timmy into a girl, who his best friend A.J. falls for, 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 fell in love with him and knowing the truth did nothing to change the feeling.
 * Played with in the Futurama episode "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 another episode, 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.
 * Clone High has an episode which follows almost exactly the same lines as the first Futurama episode mentioned above, with Joan of Arc and JFK in Leela and Zap's respective roles.
 * Additionally, Cleopatra comes onto Joan and is shocked when she is rejected. And intrigued when she finds out the truth.
 * 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 disguise is provided by Clark Kenting. When The Glasses Come Off, evil gets an ass-whuppin'.
 * Mary becomes "Mitch" after she gets fed up with discrimination in the Code Monkeys episode "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.
 * In one episode of Spongebob SquarePants, Patrick disguises himself as a woman and becomes part of a Love Triangle between Squidward and Mr. Krabs.
 * Bugs Bunny frequently cross-dresses as part of his Karmic Trickster hijinks:
 * In the classic cartoons, Bugs's "victim" invariably regards the result as attractive, although it looks rather silly to the audience. 'Cause everyone agrees it's funny.
 * Referenced in Waynes 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 responds "Me neither, I was just wondering". Considering Garth's overall character, he may have been serious.
 * 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 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.
 * In the 1952 Looney Tunes "Fowl Weather" Sylvester gives himself a very basic disguise as a hen-- and attracts the attention of a rooster.


 * Parodied on South Park: 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.
 * This happened in another episode in which Cartman suffered a case of amnesia and believed himself to be a Vietnamese woman named "Ming Lee". Wanting money, his friends had "Ming Lee" earn it for him. At least one of the clients liked it so much he didn't even become upset upon recognizing Cartman as Ming Lee.
 * In another episode, Cartman's hand was Hennifer Lopez. She likes tacos and burritos. Ben Affleck left Jennifer for Hennifer, and Cartman, who apparently couldn't control his hand, got Affleck spooge all over him.
 * The guy-dresses-as-woman variant has happened to Lumpus a couple times on Camp Lazlo. 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.
 * The Venture Brothers: Dean Venture finds himself in ?derland while wearing a Princess Leia slave girl costume (it was for a costume contest, the group theme being Star Wars). The dictator of the nation, Dr. Venture's "official" arch-nemesis, hauls off the rest of the Ventures but falls instantly for Dean. (Cue all the jokes about how Dean is a pretty wimpy guy.)
 * On the Stoked episode "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.
 * 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 disguises himself as a Cockney barwench and was able to fool Watson enough that he came on to him.
 * Because there isn't enough subtext in that relationship already, chipmunks or otherwise.
 * 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"!
 * On Family Guy Brian has hit on both a Disguised in Drag Stewie and Quagmire's father.
 * That other Seth Macfarlane show has Roger Smith, who 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.
 * Kid Flash of Young Justice can't help but find Miss Martian attractive when she assumes the shape of a female version of himself.
 * There are at least two episodes of The Flintstones where Fred dresses as a woman, and in both someone inexplicably finds him irresistably attractive. (Well, inexplicably if you discount "because it complicates the plot" as a viable reason.)
 * Parodied in The Amazing World of Gumball, where Gumball wears his mother's wedding dress to school 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 the world they live in world where animals and objects spontaneously becoming intelligent, clothes may really be the only thing they can use as a standard of beauty.)
 * An episode of The Garfield Show 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.
 * Tom and Jerry examples:
 * An episode of the Tom and Jerry comedy show featured Jerry getting a robot dog to protect him from Tom. Tom hid the robot and disguised himself to look like it. By the time the robot escaped and confronted him, a moped fell into Tom's disguise, making it look like a female dog robot. The robot fell in love.
 * When Tom was tasked with guarding the garden against a gopher, he disguised himself as a female gopher. It would have worked except that Jerry warned the gopher, who then played 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!
 * In the Chuck Jones era, Tom disguised himself as a female mouse. It worked too well.
 * The Simpsons examples:
 * In "Marge in Chains," Bart plans to use this trope against the prison warden.
 * In "Camp Feare", Abe developed feminine attributes due to not taking his medication. Another old man flirted with "her". Abe would have told the truth but changed his mind when his suitor told "her" his dating plans.
 * In another episode, there was a Stargate SG 1 convention. When the lights were out, MacGyver-obsessed fans Selma and Patty abducted Richard Dean Anderson. The people attending the convention concluded that there must be a real Stargate in the convention hall, and started looking for it until someone pointed out something more incredible: there was a girl in there. The "girl" was Groundskeeper Willy, who tried to explain he wasn't a girl and was wearing a kilt but was told he's the best they hoped to get.

Real Life

 * Isis King of Americas Next Top Model fame.
 * Some people are primarily attracted to transgendered individuals, an orientation known as transromanticism. Example: one couple thought, at first, that they were both lesbians. After a while, one of them realized he was a trans man, and his partner realized she was specifically attracted to trans men.
 * Erica Moen, noted queer cartoonist, assures us that this is because "Transmen are ridiculously hot".
 * YouTube vloggers CandiFLA, sweetnsexyts, and a good number of others. (Candi does voicetraining videos and has been known to bend back using her male voice, resulting in some amusingly jarring videos.)
 * People are often surprised to find out that Pikmin Link, the internet's most famous Link cosplayer, is actually female -- almost always just after asking where they can find more pictures of "that really hot guy dressed as Link."
 * Also applies to cosplay where the demographic watchers/players/readers are mostly female and the same goes for males who have very delicate features.