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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!"
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.
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.
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.
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.
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 Mikhail. 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.
Somewhat Lampshaded and subverted near the end of Hana-Kimi: 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.
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.
Taken to a extreme in Vandread, where 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.
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.
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.note The dubbed version, when it finally aired, had the breast scenes cut.
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-sationas 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. 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. The perspective love interest not being dissuaded when he finds out Gourry is a man could support this.
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.
Kirito, from Sword Art Online, 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.
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 major reconstructive surgery.
In one episode of Natsume Yuujinchou, 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 doesmake 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.
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 he gets longer hair, artifical breasts (though considering he is an entirely artificial person this is perhaps somewhat redundant), and a flattering dress. The result is so stunning that that some male fans admit they would go for even knowing that he is, in fact, a guy.
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 +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. The school's males are lovestruck with Moe.
In 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.
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...
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 himselfor 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.
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.
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.
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. Later subverted when it turns out Megumi always was a girl.
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 nosurprise 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.
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-hatingWholesome 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!)"
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.
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.
The female lead Jeudi in the Honoo No Alpen Rose manga. She 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 miiiight be a little infatuated with her still, and lampeents that Jeudi's not a guy.
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.
No. 6: As his local theatre was swift to notice, Nezumi makes a really good-looking woman.
The boarding school in Marginal Prince holds a festival each year, and by tradition the newest student has to play the princess. Apparantly, 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.
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.
When Tomoe is posing as Nanami in Kamisama Kiss 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.
Souta is forced to cross-dress during a few episodes of WORKING!!. "Kotori" is not only highly attractive but a huge hit with the girls and guys alike.
In what is possibly the most extreme example, Kamito from Seirei Tsukai no Blade Dance 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.
Apparently Armin Arlert from Attack on Titan is good enough of a decoy that he gets some unwanted attention from one of the kidnappers.
Nozomu in Nozomu Nozomi could pass for a girl while crossdressing even before his unexplained gender switch.
Both lead characters in W Juliet! 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.
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 Batmandressed 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, which really freaked out the "original" Peter Parker.
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.
When Photon switches genders from male to female in the 2012 relaunch of Youngblood, she has quite a few admirers, both male and female.
In issue 6 of the Samurai Jack comic by IDW, 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.
Dodge of Locke & Key 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.
"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 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, thisYu-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.
The title character has this at times, most notably in "A Girl Worth Fighting For".
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.
In 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.
Films — 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.
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.
The plot of French comedy Jupiter's 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 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!"
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, 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.
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, Christ's Childhood Pal, 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 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.
This photo◊, 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.
Wes: "So. Who's best-looking in women's dress? I vote for myself."
Averted in Tim Powers' 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!"
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.
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.note Star Trek: The New Voyages 2 (Bantam Books, 1978)
The short story "Amante Doree", from Somewhere Beneath Those Waves, features a Transsexual 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.
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.
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.
In the Halloween episode of NewsRadio, 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...
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.
In 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."
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.
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.
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.
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.
In the Argentinian/Spanish soap opera 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.
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!". 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.
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.
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:
Cara: It seems you have an admirer.
Zedd: [Indignantly] Is there any reason why I shouldn't?
The Japanese Reality ShowCrossdress 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 "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.
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).
Brunt (pointing at naked gender swapped Quark): "I tell you, that is not a female!"
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 1part 2
In another Canadian Disney Show My Babysitter's a Vampire Season 1 Episode 2, entitled "Three Cheers for Evil" the shows main characters 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◊.
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.
Averted in an episode of My Name Is Earl. 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. Some time 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 transsexual named Annie. Earl is very disappointed.
The cover art for Andrew W.K.'s 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.
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 ishis 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.
Dennis Day: You know, I saw Charleys 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.
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.
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.
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.
What makes this more intriguing is that Octavian is traditionally played by a woman.
Peter Pan productions in the United Kingdom, including the original concept. Normally, British theatre is known its Pantomime Dames: respectable male actors who play the part of an older woman in the play, performing it as a Drag Queen role. Peter Pan productions reverse this, with an attractive young woman playing the role of the prepubescent boy Peter Pan. This is a nod to the original Peter Pan story, before it was even published or performed in public. The author's children's nanny played the role of Peter when they first devised the story to entertain the kids while they were bedridden with illness over Christmas.
It's a common tradition for Pantomime productions in general to cast an attractive young woman in the "Principal Boy" role. Generally speaking, there's little or no attempt made to make the Principal Boy actually look like a boy — "he" usually wears high heels a leotard, fishnet tights, and high heels, and looks significantly more feminine and sexy than the Principal Girl.
M. Butterfly. Song Li-ling —especially when played by the right actor. The original Song was played by BD Wong who really pulled it off.
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.
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: Chaosspawned a fanart industry consisting of female versions of male video game characters, who are referred to as being "Midnight Blissed".
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. Naoto is pretty attractive as a guy, and later on Teddie handily wins a crossdressing competition.
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.
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.
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.
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.
She looked great when she had long hair too. On the other side of the spectrum, Tom (a 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.
Subverted in The 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 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 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 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).
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.
When Aki gets turned into a man, she is a total hunk.
Basically the entire plot of Material Girl; just add unwilling crossdressing. (This example needs some Wiki Magic.)
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 fans (and other characters, including straight males) that, yes, Dillon makes an attractive woman.
The transgender Senna presents as a very attractive woman, but with a penis. (She's evidently entirely happy not to finish transitioning.) The straight male Gary ends up having sex with her while he's drunk; he freaks out a bit when he sobers up and realizes what he's done, but not violently, and he doesn't worry for very long.
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 TwoKinds 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.
In Buck Godot, 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 throughout 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.
As Sarah called out Jarethnote (It wasn't even his fault. Poor guy had a cold.) about it in 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.
Vicious Whispers is a FTM example from Serenity Rose. It helps when you're a shapeshifter.
Erica Moen, noted queer cartoonist, has a DAR! strip 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.
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 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).
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.
The entire (insulting) point of the "It's a trap!" meme.
Inverted in Vaguely Recalling JoJo; 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.
The Fairly OddParents, "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 "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.
In a third season episode 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 sufficently good looking to effortlessly slip into the Brainless Beauty trope.
Female Fry: "Now when I say stupid things guys laugh and buy me stuff!"
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 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 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".
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.
Rooster: I like you, baby! You're different!(drags Sylvester off) You'll be my favorite!
Also a subversion as the rooster isn't particularly fooled and simply forces Sylvester to hatch an explosive booby-trapped egg.
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 Bros.: Dean Venture finds himself in Ünderland 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"!
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 they live in a 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.
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.
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.
Fionna is visibly more physically mature than Finn (perhaps justified since girls do mature faster than boys) and, unlike Finn, has visible blonde hair. At the very least, she is at least more human-looking than Finn.
The Ice Queen is noticeably more attractive than the Ice King, though this is actually meant to make her more sinister. Justified because the whole episode is Ice King's fantasy, though he himself exists within it.
Marshall Lee and Prince Gumball are also examples, at least in the eyes of many fans.
A G-rated version occurs in Rugrats when Tommy is crossdressed as a girl by Stu and Lou to enter him in a beauty pageant. The audiance 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.
In the Pinky and the Brain episode "My Feldmans My Friends", Pinky and Brain disguise themselves as a married couple to fool the neighbour, who falls for Pinky as Mrs. Feldman.