Unsettling Gender Reveal

""Oh, sweet Jesus, she's got a penis.""

- Mark Henry, WWE Monday Night RAW

Sexual attraction is a funny thing, and sometimes if a character physically appears to be the right gender to appeal to their sexual preference, then they'll become attracted to them, regardless of what that character's actual gender might be. Usually said character's true gender is being kept secret purposefully and they are a male Disguised in Drag or a female disguised as a male, but whether the misunderstanding was intentional or not, due to Rule of Drama, they will find out and it will be awkward, hilarious and possibly traumatizing for all involved.

This can happen to any gender and sexuality. A straight male might be shocked to find the girl he's been crushing on was a male all along. A straight female might be confused to realize that hot guy she's been daydreaming about was actually a woman. Her male Gay Best Friend, who was also daydreaming about the guy (who is really a girl) will probably feel similarly. Almost always there is shock upon The Reveal, possibly even some disgust, anger or disappointment on the part of the character who was feeling the attraction, but usually the two characters can reconcile by the end and become friends. Other times it might not bother them, or after a period of consideration, they'll decide If It's You It's Okay.

This is both a reveal trope as well as a character reaction trope, when what initially appears to be compatible gender attraction is later revealed to actually be incompatible gender attraction (Example: Straight boy likes a girl, girl turns out to be a boy). It is a sister trope to the related Sweet on Polly Oliver, which refers to when what initially appears to be inexplicable incompatible gender attraction is later revealed to actually be compatible gender attraction (Example: Straight boy likes a boy, boy turns out to be a girl), although since the unsettling part is averted, this is usually a subversion (usually).

Compare with Shapeshifting Squick, Dude Looks Like a Lady, Lady Looks Like a Dude, Bifauxnen, Gender Blender Name and Samus Is a Girl. Often accompanied by Attractive Bent Gender. Contrast Jumping the Gender Barrier and She's a Man In Japan. A subtrope of Gender Reveal.

Spoilers Off for this trope and all other gender reveal tropes, due to the fact spoilered pronouns are by definition self-fulfilling.

Anime & Manga
""What... the hell?""
 * Shugo Chara: Nadeshiko/Nagihiko, whose family has a long-standing tradition of making its boys dress, act, and, for all intents and purposes, be girls for about the first twelve years of their lives. He had to repress all boyish desires, no matter how slight, and was forbidden from revealing his true gender to anyone.
 * Juubei-Chan 2. Dropped on the audience and on Jiyu, who spent the entire series thinking this person was either chibi spirit Koinosuke or reincarnated baby Koinosuke... only for it to end up being Koinosuke's never-before-mentioned daughter who looks exactly like him.
 * School Rumble: Second Semester plays this straight at the end of the third episode. One of the characters present lampshades the moment beautifully.

"Naruto: No way?! He's prettier than Sakura!"
 * In The Secret Devil-chan: Kurosaki Sou, discovers this about Devil-chan, after just 10 pages into the manga.
 * Happens to people of both genders in Axis Powers Hetalia.
 * Everyone in the surroundings of Chibitalia mistook him for a girl until he hit puberty. In this fan comic, Holy Roman Empire gets the Chibitalia bridge dropped on him.
 * His Cool Big Sis Hungary used to be so tomboyish that she was mistaken as a boy by her rivals, and she herself thought she was a boy due to chronic lack of sex-ed in these times. It wasn't until she was a teenager that other nations realized Hungary was a girl, starting with her old rival Prussia when he sees her badly beaten after a battle and notices that her blouse and armor are torn to Absolute Cleavage levels..
 * Also, Hong Kong is often mistaken as a Bifauxnen, when in reality he's male.
 * China. Then again, Dude Looks Like a Lady and has a girlish voice.
 * At one point, Italy calls Germany for help because "There was a pretty girl, so I hit on her, but it turns out the pretty girl was France in disguise!" Since France has a noticeable beard, one has to wonder how Italy made that mistake. Then again ...
 * And even more amusingly, fans that are new to the series often assume that the author of the comics is a woman. Imagine their surprise when they're told that Himaruya is a male and experience their own unsettling reveal!
 * This is a primary plot point in Blue Drop: Tenshitachi no Bokura. The main character must have sex on penalty of death with his best friend, who has been transformed into a girl by the evil lesbian aliens and impregnate him. Happens in the reverse, too; the friend in question is uncomfortable with having sex with the main character as well. Then it's found out that the best friend's mind was simply put over the top of a random alien girl's mind. When they fully merge at the end of the manga, it's unknown if he is a she with a guy's mind, or a guy still trapped in a girl body. It's rather messed up regardless.
 * Happens to a couple of Kuwabara's schoolmates at the end of Yu Yu Hakusho when they mistake Kurama for Kuwabara's pretty girlfriend. In the anime he's nonchalant, but in the manga he gets homicidally angry.
 * In the second season of the Slayers anime, during their tenure in a Lady Land kingdom for the cross-dressing episode, a disguised Zelgadis meets and becomes smitten with the kingdom's demure and burdened princess, Miwan. After he saves her from a water demon named Evia, Miwan declares herself free from her burdens...and promptly takes all of her clothes off and reveals herself as a man. It turns out that half of the population of the kingdom also had disguised men among them, much to everyone's disbelief.
 * A side story in the novels also has Zelgadis encounter another girl, named Miranda, dressed as a male bounty hunter. During his fight with another chimera, her gender is revealed.
 * Flame of Recca
 * Happens twice in the same minute in the anime. A dim bunch of henchmen have been told to apprehend a high-school-age boy, and they identify Fuko (a very tomboyish, macho girl) as their target. Immediately afterward, the rather feminine Tokiya screams at them, "You idiots! I bet you thought I was a girl!"
 * Subverted in the manga. Recca asks Aoi three questions, the third being "Are you a guy or a girl?". Aoi answers that he's a guy, but instead of being stupefied about the gender, Recca merely brushes it off to mean that he can fight as he pleases.
 * Asuta from Kashimashi: Girl Meets Girl, whose best friend Hazumu got turned into a girl, struggles with this a great deal. Strange enough this is only played for laughs, whereas the feelings that the female friends have for Hazumu get treated a lot more seriously.
 * Sailor Moon:
 * Minako manages to nonchalantly gush over Haruka a few times well after everyone else was clued in to her being a girl.
 * And the readers themselves will experience an unsettling reveal if they compare Zoisite in the original Japanese version and the American dub.
 * Also, the Starlights (in the manga).
 * In an early episode of the R season, Mamoru and Usagi team up to take care of a baby named Manami. When they change the baby's diapers, it turns out Manami is a boy and not a girl; he has a Gender Blender Name and had been referred to with gender-neutral pronouns. (The dubs generally handle it by referring to the baby as a girl irst, and then as a boy.)
 * Happens in the anime Girls Bravo, where Fukuyama starts hitting on and eventually sticks his hand into the panties of a crossdressing Yukinari . His reaction is not pleasant considering the fact that he is extremely androphobic and is allergic to other men.
 * .hack - Given that the entire series is based on a fictional MMORPG, there are plenty of GIRLs around.
 * In .hack//SIGN, Tsukasa is the Bridget that gets dropped on herself. Among the initial worries that come with a revelation like this is that her gender will affect her relationship with Subaru. Turns out, it didn't matter.
 * It also happened in .hack//Roots when two female players attacked Haseo and their voices change.
 * The audience of Otome wa Boku ni Koishiteru gets the main character Mizuho's gender dropped on them—if they didn't read the series synopsis before watching the first episode. Most of them, mortified at having cheered at the fanservice, firmly invoked the First Law of Gender Bending in their minds.
 * The relatively obscure manga and animated movie They Were Eleven by Moto Hagio features an incredibly feminine recruit who is eventually revealed to be an alien who hasn't yet decided whether to be male or female, and actually became a recruit to avoid being forced to become a girl as well as a pawn in Arranged Marriage imposed by their family.
 * Hayate the Combat Butler:
 * Poor Hayate gets forced into female clothing often, and there have been several cases of this. However, the most amusing was when he had to crossdress in order to attend an anime convention, and ends up having to fight a giant robot while wearing a maid costume. Naturally, this makes all the fanboys happy and taking pictures, even mentioning 'I saw white!' only to have Hayate respond that he's a guy. Their response? HE'S A TRAP! and, of course, take more pictures.
 * Luca, a pop star that Hayate helps after the robot hurts her, falls for it too, even going so far as to change in front of him. Due to the large amount of stress she's under, Hayate tries to keep up the disguise, digging deeper and deeper with lies. The plan finally fails when she gets into a bath that he's in, along with more than one of his female classmates.
 * One butler falls in love with Hayate, who at the moment is under a crossdressing curse (...). Although initially devastated when Hayate's cover is blown, he quickly comes around and tries to convince Hayate to travel with him to the Netherlands, where same-sex marriages are legal. (Cue Nagi's Megaton Kick.)
 * Ban and Ginji actually try peeping on Kazuki in a hot spring in an episode of GetBackers, mistaking him for a girl at a distance. Later, Amon Natsuki hits on him and tries to pull an I Kiss Your Hand. Juubei merrily skewers them both times.
 * In Vandread, Bart Garsus gets a Bridget dropped on him with The Reveal that BC is a Gender Bender Mole. In the end, it doesn't stop him. If anything, it made it easier for him to accept his own feelings: the premise behind the whole series has men and women living on completely different planets—so same-sex "loves" were common practice.
 * Jan Suk in Monster has the Bridget to end all Bridgets dropped on him when he starts confiding in a cute blonde girl he met at a bar. Not only is she actually a man, but she's Also counts for the viewers, as it's a Shocking Swerve. Has caused anime clubs to riot.
 * Naruto:
 * During the Land of Waves Story Arc, Naruto meets Haku, whom he takes for a girl (Not that this is hard), and Haku corrected him on this assumption right before he left.

"Gold: Hi there miss. Isn't it lonely to do sightseeing by yourself? Wanna go for a cup of tea together? The name's Gold. I'm from New Bark Town. Bugsy: I...I'm Bugsy from Azalea Town. And... well... I'm a guy."
 * Before the anime gave him a deep, masculine voice, Deidara was frequently mistaken as female.
 * Happened to Karin in Kamichama Karin at the end of volume 4 finding out her crush, Kirika-senpai, is female through an incident of seeing (and accidentally feeling) her revealed cleavage in an unconscious state. The audience gets the Bridget dropped on them first as it's revealed in an earlier chapter.
 * Shaman King
 * Amamiya Ryu aka Bokuto no Ryu thinks that Lyserg Diethel is a girl at first. When Lyserg reveals his gender, Ryu can't believe it until Lyserg calmly lets him check in his underwear (anime) or drops his pants in front of everyone (manga). Ryu doesn't seem to care and remains very protective and devoted to Lyserg
 * Alto Saotome from Macross Frontier, a former Kabuki actor who often played female roles, gets this a lot... but trust us, he's certainly not happy about it. In one episode a salesman mistakes him for a girl and tries to sell him women's clothing, to which Alto angrily points at his Adam's apple and says "Does THIS look like a woman to you?!" Teammate Mikael loves to jerk Alto's chain by referring to him as "Princess Alto" and similar nicknames.
 * Wandering Son
 * This happens to Riku Seya, a classmate of the Shuichi's older sister, Maho. Seya saw Shuuichi dressed as a girl and became infatuated, and convinced Maho to set them up. A future date at the aquarium turns into a rather shocking revelation which is not helped by a friend of Shuu's, "Mako-chan" (No, not that one) also revealing himself. Seya is left rather confused by it all.
 * The series has had a few instances of the rare female-to-male Transsexualism case too.
 * In Rurouni Kenshin, Villainous Crossdresser Kamatari drops a Bridget on his opponent Misao (and everyone defending the Aoiya as well) quite dramatically, complete with pixellated naughty bits. Note that particular scene was only in the manga (though the actual reveal still happened).
 * Kenshin himself often causes this with viewers, and the fact that he's voiced by a woman in the original Japanese makes it worse (and legend has it that the character designer for Guilty Gear first came up with the character Baiken after making this mistake) and he's in fact based on a historical samurai, Kawakami Gensai, who used his feminine appearance to get close to his targets and even managed to assassinate a man in broad daylight. He even hid out in a brothel at one point after an assassination.
 * Done way too often in Gravion, to the audience, sometimes. Right in the first episode, the show seems to take delight in showing off a beautiful young woman, Male Gaze and all, then a minute later revealing "her" to be the main character Eiji in disguise. A later episode begins with more Fan Service, panning up the backs of the legs of a maid washing dishes, only to then reveal that, yep, it's Eiji again.
 * Subverted in the adult manga Sundome; Sahana tells Hideo that she used to be a guy, but it's a trick to try to get him to stop masturbating so much. It Makes Sense in Context.
 * Ouran High School Host Club:
 * Happens to several characters when they discover Haruhi's real gender, most notably Tamaki, Kasanoda, and in the last chapter, the entire female customer base of the Host Club. And then Double Subverted when Haruhi tries to explain the truth of her sex to the club's customers, the girls assure her that they've known all along and don't mind a bit. Only later, after Haruhi and Tamaki have left for America, is it revealed that what they "knew all along" was that Haruhi was a gay crossdresser and that Tamaki was in love with "him."
 * Surprisingly does not happen with Haruhi's Drag Queen father Ranka. The host club knows that he's her father from the moment he enters the scene.
 * An oddly sexuality-inverted version occurs in Glass Fleet when Holy Emperor Vetti Sforza finally manages to get Michel Volban, the leader of La Résistance, into his clutches... and, upon drugging Michel in order to have his way with him, discovers that Michel is actually a woman. Vetti seems rather put out about it.
 * Ranma ½:
 * The reverse happens to Akane at the very beginning of the series. She wasn't exactly thrilled to find out that the shy and awkward girl she had just made friends with was actually a guy.
 * A subversion: Hiroshi and Daisuke's discovery that the cute redheaded girl they were hot for is actually their male best friend does absolutely nothing to stifle their crush ("Why can't there be more girls like him?")... though this is because Ranma doesn't wear bras and tends to get "her" shirt destroyed in public fairly often, as well as being willing to dress up in deliberately "sexy" clothes in order to manipulate Kunô or some other sap.
 * This happens to Ranma too, when he tries to romance Tsubasa to get "her" to give up on Ukyô and his own female side. His reaction to finding out Tsubasa is a male Master of Disguise (which includes crossdressing as a girl) is not pretty.
 * Everyone believes Konatsu to be the legendary Genius Kunôichi (female ninja), and have even braced themselves for her coming out of the closet to confess undying love for Ukyô. Then a stray bomb goes off, blows apart Konatsu's outfit, and reveals "she" is a very feminine-looking "he". Ukyô is just as stunned as everyone.
 * A rather bizarre example occurs in Fist of the North Star: Rei is introduced wearing a pink cloak and is mistaken for a woman, as only his eyes are visible. It's not until he speaks, and fully pulls the cloak off that his manly bod is revealed. It's worse in the anime, where Rei is pursued by several men trying to get a date.
 * Omamori Himari did this recently with a side character. Right after Rinko mentioned about her having two more rivals... Lampshaded by Himari.
 * In Gankutsuou, this happens to Albert as early as Episode 2. The "woman" then proceeds to tease him about it for the rest of the series. And later appears to go on to a successful modeling career... This is an expansion of a minor character from The Count of Monte Cristo, who lured Albert into Vampa's trap.
 * Pretty much the main premise of Stop!! Hibari-Kun! Main character Kohsaku moves in to his dead mother's yakuza friend and falls in love at first sight with the eldest and most beautiful of his four daughters... only to later find out that he is actually a very convincing crossdresser. Hilarity ensues.
 * Classic example: Shun from Here Is Greenwood. He's used for a prank because of this.
 * Fullmetal Alchemist:
 * Happens to Greed in one OVA in which he flirts with "Winry" who is actually the shapeshifter Envy, who is male in this version.
 * Cowboy Bebop: Ed! Nobody finds out she's a girl until Faye tickles her! Everyone else can be forgiven since she's a pre-pubescent Tomboy with little social skill, and it's also a Mythology Gag to when Ed really was a boy in the original version of the story before being changed to a girl for balance.
 * The appropriately-titled No Bra centers around a guy who finds out that his Forgotten Childhood Friend Yuki is actually a guy, despite what he looks like.
 * Happens once in +Anima, when a boy named Kevin falls in love with Husky, thinking he's a beautiful Mermaid Princess. Eventually, Husky tries to break the news him that he's really the 'Mermaid Princess' without overwhelming him, but ends up screaming it at Kevin before becoming human again. Kevin, is, to say the least, rather shocked that his Mermaid is Husky.
 * An episode of Kodocha has a subplot where one of Sana's friends develops a crush on an upperclassman tennis player. When she confesses her love, the object of her crush explains that she's a girl.
 * In the anime of Rose of Versailles, the Duke of Orleans tried to do this by having a very girlish and young-looking henchman impersonate Marie Antoinette, thus ruining the marriage to the Dauphin. It doesn't work.
 * Lesbian variant: In the first OVA of El Hazard, Makoto is forced to pose as the missing princess Fatora. Apparently, he pulls this off a little too well, because Fatora's lesbian lover Alielle climbs into bed with him. Her response basically boils down to: "Well, that's new... wait a minute... Oh, my God!" The episode ends with both of them screaming.
 * Prunus Girl: Logically, Maki "knows" that Aikawa is a guy, but he still can't help but be frequently embarrassed by Aikawa's antics (and occasionally be tempted to take up offers to personally verify gender). Meanwhile, his friend Kadoyama is hopeless over Aikawa, declaring "who cares as long as (s)he's cute!" and getting really worked up. A nameless herd of classmates seem to agree.
 * Mobile Suit Gundam 00: Tieria Erde, although his voice and personality help to only keep the viewer in the dark for parts of the first episode. Still, his girly looks and the fact that he wears a fuzzy pink sweater when not burninating the countryside in his Gundam cause enough of a double-take to fit him in here. To add to the confusion, the people making the show claimed Innovators have no sex. They actually, meant that they were androgynous. It was just badly translated and underwent Memetic Mutation before the correction came around.
 * He doesn't make it any easier in the 2nd season, when it's shown that he can really fill out a ballgown. Maybe Eiji gave him some tips...
 * In the Hideshi Hino short story Sailor Psycho, a girl is invited to the school idol's house to paint her portrait. She ends up discovering that the school idol is really a crossdressing boy with a school uniform fetish. The girl is killed when she freaks out and we find out that the idol's "mother" is really his crossdresser father and the old caretakers of their mansion are also crossdressers.
 * Subverted in The Day of Revolution Former boy Megumi actually wants to drop a Bridget on the only boy at school who doesn't know her "secret" but the other girls forbid it for reasons of their own. (And when she finally did decide to tell him he wasn't listening.)
 * Played with in all directions in the manga series Family Compo. The main character moves into his aunt and uncle's place, and finds out that his aunt is really his uncle and his uncle is really his aunt. They're a transsexual couple.
 * In Bleach, Yoruichi debuts in the form of a male cat, complete with male voice actor. Her actual form is very feminine. Kisuke Urahara's first line spoken to her cat form was "Who's my favorite pussy?" in the English dub... Hilarious in Hindsight or Getting Crap Past the Radar?
 * In episode three of Kino's Journey, a Bridget was dropped on all the audience members who thought Kino was . The ones who guessed right didn't hesitate to pat themselves on the back.
 * In Maria Holic Kanako, the lesbian protagonist, meets the girl of her dreams in the form of the Mariya after transferring to all girls school. Later she walks in on Mariya changing and discovers his secret. She spends the rest of the series being relentlessly bullied by him into keeping his secret and suffering innumerable Stupid Sexy Flanders moments.
 * Azami in Himawari!. "Wait... the hot one?"
 * In the Arina Tanemura manga Gentleman's Alliance Cross (Shinshi Doumei Cross), the character Maora was so feminine in the first volume that even the staff who read it thought that he was a girl. His real gender wasn't revealed until the second volume.
 * Pokémon Special:

"Brock: Hey, you're not changing with Ash and I? Is it because of May? Anabel: No, it's because even if I don't look like the part... I'm a girl."
 * Another Bugsy example happened in Golden Boys, another GSC manga. When meeting Gold, Bugsy referred to himself as "... a bug keeper boy..." which provoked a "You're a boy?" from Gold. Nothing else was noted though.
 * Pokémon:
 * In the anime, Brock wound up subverting this on one occasion. He knew something was wrong when a ridiculously Hot Scientist didn't make him delusional. Turned out to be a man in disguise working for Team Magma. In a later episode, he identifies the same disguised man out of two otherwise indistinguishable Jennies by the same lack of a Raging Stiffie.
 * And then later he accidentally hits on Harley.
 * He also failed to realize that Anabel/Reira was a Bifauxnen.

"Tsubomi: O...Ojou-sama?!"
 * Brock also sometimes falls for Ash whenever he dressed up as a girl.
 * An example between Pokémon: Meowth and Ash's Oshawott both fall for a Purrloin. The expressions on their faces following the surprise revelation are priceless. The pairing name for this Purrloin/Meowth became, appropriately enough, Bridgetshipping.
 * Happened to Blade in NEEDLESS after rescuing a crossdressing Cruz.
 * When Kouji Nanjo from Zetsuai 1989 was a young boy, he once saw a rage-filled, beautiful Tomboy named Izumi. He fell in love with her at first sight, but she disappeared from his life as fast as she arrived. Several years later, Kouji is watching a high school soccer game and recognizes one of the players, soccer star Takuto Izumi, as the young girl that captivated him, since "Izumi" was the kid's surname. After quite some Gayngst about it, Kouji decides that he doesn't care, he doesn't like men that way, but... it's *Izumi*, dammit. Besides, it would soon get worse.
 * Himemaru in Rappi Rangai. Despite being born male, he decided to become a kunôichi because he had the "prettiest face in the village," though Kisarabi claims it was because he didn't want to put himself through the hard training to become an actual male shinobi. In either case, he seduced Raizou in his introductory chapter, and even after his secret came out he continued making passes at him every so often.
 * Detective Conan
 * The entire population of Tsukugeshima in "Moonlight Sonata" case was not only surprised that the island's only doctor Narumi Asai is the Villain of the Week, but also that "she" is a man.
 * Much later, Conan, Hakuba and Heiji get a reverse Bridget drop when they see that the "Detective of the South", Koshimizu, is a Bokukko. They only find out when she puts on her school uniform... a feminine seifuku instead of a male gakuran. (OTOH the "Detective of the North", Junya Tokitsu, already knew and didn't tell them; in fact, he was surprised to learn that they didn't know about Natsuki's gender.)
 * And the reverse-drop happens again when Action Girl Sera Masumi appears. Conan, Ran and Sonoko don't find out that the handsome and devil-may-care boy that said Ran was "his type" and helped them resolve a case, was actually a Bifauxnen... until she appears in a female highschool uniform and transfers to the girls's class.
 * A mild version pops up in How I Became a Pokémon Card. Akira's and his best friend Akari are beginning junior high, and uniforms come into play. Akari has to wear the female uniform, which provokes Akira to mention how he didn't believe Akari really was a girl.
 * Inverted in Akahori Gedou Hour Rabuge episode 9, where the son of a businessman that Kaoruko is babysitting (the kid, not the businessman) ends up being a girl, much to Kaoruko's dismay.
 * Soul Eater:
 * One of Kilik's weapons, is actually a hot guy. Squees for everybody.
 * This will happen with Crona if the author ever gets tired of their "gender will always remain ambiguous" concept. One side will go "I knew it, Crona was a guy/girl" and the other will go all "awwwww, not the gender I thought of."
 * This happens to Wataru Takatsuki in Yubisaki Milk Tea in recent chapters. However, despite Yoshinori Ikeda's initial beliefs to the contrary, Wataru actually likes him even more.
 * A Running Gag with Aoi from You're Under Arrest, who's a Transsexualism woman whose gender issues are portrayed fairly realistically,
 * In Heartcatch Pretty Cure, Tsubomi quickly becomes smitten with the handsome Student Council President Itsuki. When she learns that "he" is actually a handsome girl, she's upset and shocked enough to end up staying home with a fever.

"Hinoe: ... Where are your boobs!?"
 * Cobraja ends up choosing Itsuki to be a Desertian (mostly) because he thinks she's a beautiful man and when Cure Marine reveals that he's a she, he promptly freaks.
 * Natsume Takashi from Natsume Yuujinchou tends to get mistaken for his grandmother, Reiko, by Youkai on an almost constant basis. One of these Youkai is Hinoe, who really liked Reiko and Does Not Like Men. She gets as far as groping Natsume's non-existent breasts before she learns her mistake.

"Iono: Who would have thought even a dedicated skirt chaser like me could have been fooled."
 * In chapter 279 of Air Gear while fighting Agito, Shalott reveals to Agito that he is actually a guy (and a VERY well endowed one) before knocking him down, sitting atop him and saying after he beats him up he can "have a lick" if he wants.}
 * In Sakura Gari, we have a boy named Youya... better known as Sakurako Saiki. This is not Played for Laughs as s/he is an insane, thoroughly broken Yandere, who ends up Driven to Suicide.
 * Black Butler: While undercover in a circus, Ciel shares a tent with a skinny teen that he calls "Freckles". Turns out that he is really a girl named Doll. She offers to show him her privates so he can be sure.
 * Togainu no Chi: Rin, a dude who looks like a lady, drops a bridget on Akira and Keisuke in episode 2. "Sucks to be you! I have a you-know-what!"
 * MM! has Tatsukichi himself. The Cross-Dressing Voices helped out a lot. Taro then gets disappointed since his crush on the first episode, is his cross-dressing friend.
 * Kuragehime has Kuranosuke.
 * Played for Laughs with Karara's debut in the Keroro Gunsou anime: Tamama spends the entire episode flitting between jealousy at the thought of being replaced as the platoon's Cute Shotaro Tadpole and being charmed by the new 'recruit's' Hero Worship of him. Then, when Karara heads home, she promises to become a good future bride for him...
 * In Aphorism, this is how Hinata and Mino met for the first time. Hinata even had a crush on him for a while: his reaction at the Bridget-dropping was throughly expected.
 * In Adolescence of Utena, the Revolutionary Girl Utena movie, Utena is so Bifauxnen that one of the main characters (Saionji) thinks she's a guy until halfway into a duel when he manages to cut her shirt open. While surprised, it's only evident in his choice of words, his face and voice remain as level as ever (for him) and he continues to attack her.
 * In Otomen, when he was a little boy, Kasuga developed a crush on his sweet, gentle cousin. Flash-forward ten years, and imagine his shock when he learned that his cousin grew up to be a tall, handsome guy.
 * In Karakuridouji Ultimo, Service, who up till then was the source of much Viewer Gender Confusion, got his shirt blown off during a fight in Chapter 23, revealing... a flat chest. We next see Yamato's face with an expression of pure shock. The fandom was mind-blowned too.
 * In Digimon Xros Wars episode 28, it's revealed that Cutemon, the two-foot-tall, pink, scarf-wearing Healer of Team Xros Heart, is a boy.
 * In episode 6 of Kämpfer, Natsuru inadvertently does this to when his identity is compromised. Apparently, his clothes only change during transformations if he/she is wearing the Seitetsu Academy uniform.
 * Iono the Fanatics: Well, Dropped a Bridget on Her really. However, inverted. Iono not only isn't uncomfortable with Tomo Senoo when she finds out the cute girl she was crushing on is a he, she's actually impressed.


 * Subverted in Wild Rock. Yuuen dresses up as a girl for a Honey Trap plot, but eventually feels guilty and upset that Emba is in love with his female persona and decides to run away rather than "drop a bridget" on himself. He then finds out Emba actually knew all along but didn't mention it because he didn't want him to stop coming.
 * Ice Revolution is one long series of dropped Bridgets after martial artist and extreme Tomboy (so extreme her hairdresser likens her to a fellow Transsexualism) Masaki decides to take up the very girly sport of figure skating, culminating in her dropping a Bridget on an entire ice arena when she appears on the ice at her first public performance wearing a skating dress. Everyone at the rink had just assumed she was a boy up until that point.
 * Poor Masamunya has one dropped by the title character of Nyanpire seconds after developing a crush on him.
 * PG version in Cardcaptor Sakura. When Sakura, Kero and Tomoyo have to catch a Clow Card that has taken residence in a painting, they meet with a boy named Yuuki whose Disappeared Dad is the artist who painted it. At the end of the episode Yuuki's nice hat falls off and reveals very long Rapunzel Hair, thus showing the trio (and us) that Yuuki is a tomboyish girl.
 * The "tomboyish girl wears a Nice Hat and then The Reveal happens when the hat's dropped and you see her long hair" also happens to Kunimitsu Tezuka from The Prince of Tennis, when he meets Miyuki Chitose. Except it's Girlish Pigtails instead of Rapunzel Hair.
 * Much to the shock of the heroes of Samurai Champloo, this is not the case with the tourist they meet in one episode. Granted he IS surprised to find out the kabuki actor he had a crush on is a man, but it's a pleasant surprise.
 * Author Mineyo Maya of Patalliro! Fans are shocked to find out that the shounen-ai author is a happily married man with three kids.
 * Inverted in Mayo Chiki. The butler for a local rich girl, Konoe Subaru, is actually a girl. She was allowed to be a butler, which is a men's only profession, on the condition that she can hide her gender from the students at school. Her cover is nearly blown when Ordinary High School Student Jiro accidentally finds it out. But luckily for her, he agrees to keep it a secret (largely due to blackmail from said local rich girl, who also promises to help cure his gynophobia, or fear of women, as he suffers from nosebleeds anytime a woman touches him).
 * Jun Watarase of Happiness!, who dresses like a girl, looks like a girl, speaks like a girl and even has a crush on the main hero is actually a gay, androgynous boy which is revealed pretty soon. His motive for behaving like that is "because the female school uniform suits him better and does make him popular among male students." In the sequel for the game, Happiness! Re:Lucks a route of sorts was added for Jun, making him a valid target to pursue.
 * The backstory of Prism has Megu spending a romantic day with a boy back in grade school... only to discover on her first day of high school that Hikaru is actually a girl.
 * Code Geass: In the Turn 9.34 picture drama C.C., Kallen, and Lelouch dress up as belly dancers to sneak into the Chinese Federation. C.C. and Kallen introduce Lelouch as their "beautiful older sister" and the men ogle him. Of course, Lelouch has a masculine voice, so when he speaks, they realize that he's a guy.
 * In the D.N.Angel manga Satoshi once went Disguised in Drag and Dark almost kissed him before he realized he's a guy.
 * In Moyashimon, a certain  is not all she seems. Oikawa goes on a rampage when this is revealed to her after she witnessed a kiss.
 * Prostitute Haru from Fire Candy, pretty much all of the gang members who see him for the first time assume that he is a cute, young flat chested girl and only later (often already past the point when it would be just diosturbing) are informed of the error in that assumption.
 * A variation appears in Kuroneko Guardian. An actor is assigned a bodyguard who he believes is a boy until he walks in on her topless (when she was taking a shower).

Comics -- Books
"Dean: Damn hippies..."
 * Even DC Comics' woman-lovin', homicidal, Anti-Hero Badass Lobo has had this happen to him. In "Lobo's Big Babe Special", he is hired as a bodyguard for an intergalactic beauty pageant. But each of the ladies in the pageant has one nasty surprise or another (even the ones he knew!) and were subsequently eliminated. Each of them, that is, except the extremely busty T.V., the one Lobo has been drooling over the entire time. Once T.V. was crowned the winner, the horny Main Man made his move, despite her subtle hints that it wasn't a good idea. Finally, T.V. tells him to "put your hand here." I think Lobo and everyone reading now knows what the name "T.V." stands for...
 * Used, of course, in Liberty Meadows. Dean goes to a bar and sees someone who, from behind, appears to be a lovely long-haired lady. He proceeds to crudely offer to play some "tonsil hockey" with her before discovering that "she" is in fact a long-haired man.

"Zenith: TNT Tom left with a smile on his face, mind..."
 * In one arc, the guys were trying to catch some other pesky animal, possibly a beaver or badger. A tactic they tried was having Ralph put on a wig so the critter would be attracted to him. Not only did it work, but Dean also came on to him. The final panel of that strip showed Dean frantically scrubbing himself in a shower and screaming "NOOOOO!" while a radio or recording played, "I know what it's like to play The Crying Game..." The animal they caught had the same reaction to the reveal.
 * In Camelot 3000, Tom Prentice awakens memories of Camelot in Sir Tristan's reincarnation, who happens to be a gorgeous young woman. Tom's instant crush on the reborn Tristan plays out this trope.
 * In Promethea, this happens to Dennis Drucker, who finds out that his goddess lover (one incarnation of the eponymous Promethea) is actually comic book artist William Woolcott. This ends about as humorously as most Real Life examples of this trope.
 * Between X-Men characters Scott, Jean and Warren in Marvel1602. Jean is a Bifauxnen who has been disguised as "John Grey" as part of her education, and when Warren shows up, he starts hitting on her. Scott confronts him angrily, revealing the secret that Warren must have obviously glimpsed... only for Warren to reveal he had no idea "John" was a woman.
 * Grant Morrison's Zenith had the title character propositioned by Metamaid, an attractive pre-op transsexual superheroine. After Zenith finds out, he passes the buck to the naive young superhero TNT Tom by suggesting that he and Metamaid might like to get acquainted. At least it apparently ends happily for both parties.

Fan Works

 * Frieza did this to Krillin in Dragon Ball Abridged. Later,  inverted this to everyone.
 * A slightly different version used in the sequel to A Very Potter Musical: the gay Dumbledore falls for the rather mannish Professor Umbridge (who, incidentally, is played by a man), and is shocked and horrified when he discovers that she doesn't have a penis.
 * In the Spider-Man fanfic "Blessing In Disguise," Harry discovers that Peter Parker has turned into a girl when he startles her and she falls out of the shower in the locker room on top of him.

Films -- Animation

 * Francis the ladybug in A Bugs Life has to constantly reveal his true sex. And given he's voiced by Denis Leary, he does it in the most caustic way possible.

Films -- Live-Action
"Lug: Not a woman? Madmartigan: (To soldiers) Fellas... Lug: Not a woman!? Madmartigan: Meet Lug."
 * Handled much more realistically in possibly the most famous example, Fergus and Dil from The Crying Game. Subverted in that, even after finding out about Dil, Fergus realises that he still loves her. For most, this is All There Is to Know About "The Crying Game".
 * Madmartigan's performance in Willow.

"Guitar Wolf: ACE! Love has no borders, nationalities, or genders! DO IT!!!"
 * In Ace Ventura: Pet Detective, Ace Ventura figures out that detective Lois Einhorn is actually Ax Crazy former professional football player Ray Finkle and is responsible for the kidnapping of the Miami Dolphins's mascot Snowflake and quarterback Dan Marino. He then remembers that Lois had tried to make out with him earlier. He gets Squicked. Badly. Later, when Ace Ventura exposes her former identity to the rest of the police force, all the twenty-odd policemen present, Dan Marino and the dolphin also get Squicked. Apparently she got around... (and as a shout out to make it funnier, the song playing in both sequences is Boy George's "The Crying Game")
 * The Associate: A gender-swapped version of this trope occurs when Camille Scott, a business associate of main character Laurel Ayres (a black woman), goes public with a story about being pregnant with the child of Ayres' business partner, Robert Cutty (an elderly white man) after Cutty refuses to sleep with her when they meet privately one evening. At the climax of the movie, Cutty reveals that "he" actually is a well-disguised Ayres.
 * The ending to Some Like It Hot has "Daphne" revealing his true identity to the millionaire who is about to marry "her". His response is priceless.
 * In Without a Clue, Reginald Kincaid (playing Sherlock Holmes) is quite attracted to Lesley Giles.  Lesley Giles  is a man who habitually dresses as a woman.  "Holmes" and Watson manage to palm Giles off to Lestrade, claiming (truthfully) that Giles "appears on the stage in Paris", in an act called "Les Femmes Faux".
 * In Trainspotting, Francis Begbie picks up a woman in a club. Outside, in the car, he's making out with her, then goes to rub her down there, and finds she has a woodie...
 * Played for laughs briefly in Blades of Glory. When several people are interviewed to see how they feel about the male/male pair skating of Chaz and Jimmy, one guy comments in surprise "Wait, the blond chick's a dude?"
 * silhouette reveal as (possibly?) a joke in The Naked Gun 33 1/3. The DVD commentary revealed it was a stand-by and they were going to use . Luckily, the cable TV airing show this variant, while movie channel keep the silhouette intact.
 * Played straight in the Japanese rock 'n' roll zombie epic Wild Zero, when the male lead finds out that the girl he's been chasing all movie is actually a guy in drag... then wondrously averted when the god of rock and roll himself tells the guy not to be such a wuss, as love knows no gender. One of the best film lines ever:


 * As you can guess by its title, Victor Victoria provides a few perfect examples of the reverse of this. The one that stands out most is when Victoria, dressed as Victor, pulls Norma into a bedroom and acts as if she wants to have sex with her. Norma later bursts out of the room and proceeds to yell angrily at her ex(?)-boyfriend (who is now dating Victoria) that Victor is a woman.
 * Is the plot of a Mexican comedy Los Dos Rivales.
 * At the end of Tomboy. Laure is She also goes to visit.
 * In The Hangover Part II,
 * The Cult Classic horror movie form the 80's, Sleepaway Camp sets this up as a big reveal. It's probably one of the few times this trope is played for horror and not laughs/drama.
 * Technically it is Played for Laughs (sorta). Rather than being shocked that these people were killed by him (which is frankly not shocking), they are very surprised that "she's a man."
 * What's even better, somebody remembered it and wrote a comedy sketch about it!

Literature
""We were having so much fun I thought, 'why stop?'""
 * There is a pornographic story that was written in first person, in which the narrator makes love to a man. In the last sentence of the story, it is revealed that the narrator is also male, which is a revelation to the reader.
 * Done with a twist in the Darkover novel Hawkmistress: The main character is a young woman disguised as a young man, and is traveling with a group of mercenaries. The leader of the group starts hitting on her. She figures he's seen through her disguise; turns out he's gay.
 * At the end of the third Sir Apropos of Nothing novel, Tong Lashing, the revelation that evil crime syndicate leader (and Apropos' brief lover) Verah Wang Ho is a man leads to his (anti)Heroic BSOD which ends with
 * A variation of this happens to Ivan Vorpatril in Lois McMaster Bujold's A Civil Campaign when he, realizing how slim pickings were for long-term female companionship, decides to intercept his old (and older) lover Lady Donna Vorryuter on her way back from Beta Colony (something related to an inheritance dispute surrounding her brother the late Count Vorryuter) and perhaps renew matters with said divorcee. Now who is that fellow with the black beard accompanying the Vorryuter Armsmen and why do his eyes look so familiar?
 * In the novel Trainspotting, it happens to Renton, not Begbie. Furthermore, he doesn't panic, but admits to always being curious about what it would be like to sleep with a man. Taking advantage of the opportunity, he ends up getting to third base; however, his friends then walk in on him, scaring Renton off any same-sex encounters until he finds himself in London without a place to spend the night.
 * In Moon Over Soho Ash Thames (one of the river spirits from the Upper Thames river) picks up a girl in a bar, when he gets her into bed he discovers she is a very convincing crossdresser. It turns out not to bother him, because in his own words...


 * In Let the Right One In, Oskar finds out that  He doesn't mind, though. The Swedish film includes this plot point but is a bit more ambiguous about it, while the American remake mostly removes it, and a deleted scene suggests that.

Live-Action TV
"Maeby: "It's pronounced 'Shemalé'.""
 * Korean drama Coffee Prince is actually an odd example. The manager initially thought he was in a gay relationship, and was hesitant for this reason. But since he was trying to avoid arranged marriages and was so shocked to suddenly find this out, even though it was a workable relationship.
 * Oh, David Tennant! Or should I say, "Davina"... Seriously, watch this!
 * In Kamen Rider W, the heroes use Wakana as bait to attract the Liar Dopant.
 * Also Akiko is one of the male-seeming bodyguards.
 * The Korean Series You Are Beautiful has a convent novitiate dressing like her twin brother to join a pop band. And the drummer was the last to figure it out...
 * In the episode of Quantum Leap What Price Gloria, Sam uses this trope to enact revenge on his (female) host's boss for his treatment of her best friend. Sam convinces him that his host, the woman he'd been lusting after all episode, is secretly a man, playing with this trope even though the host has always been a woman.
 * In Cory in The House, it happens to Newt Livingstone when Cory poses as his sister Raven (for reasons too convoluted to get into here) and Newt falls for him despite "her" clearly being his best friend in a dress and a wig. Then again, Wig, Dress, Accent was a staple of CITH's parent show That's So Raven, and Newt is very stupid.
 * Another sexuality-inverted instance occurs in an episode of 3rd Rock from the Sun, in which a Guy Of The Week dumps Sally when he finds out, to his dismay, that she isn't a guy in drag.
 * NCIS has a first-season episode "Dead Man Talking". While investigating a missing embezzler, Tony ends up on a date with a woman connected to the missing man. Afterward, Kate rarely missed an opportunity to remind Tony of the incident.
 * Happened once to Sanchez from The Closer. He made the mistake of  Poor, poor Sanchez.
 * Farscape episode "The Flax", . This becomes Squick material for D'Argo when.
 * Parodied(?) in an episode of Celebrity Juice. Host Keith Lemon, in the episode following "Let's Dance for Comic Relief", in which he was a competitor with dancing partner Paddy Mc Guinness, opened the show saying that said partner got off with 'Roberta' Webb- only to discover 'she' had a 'tallywhacker'. 'Roberta' being Robert "Mitchell and" Webb, another competitor who performed "Flashdance" in a leotard and frizzy wig.
 * Inverted in an episode of The Drew Carey Show where Mr. Wick is challenged to find a crossdresser on the floor, after looking for a while Dionne Warwick walks in and Wick declares her a drag queen and grabs the music legend in her crotch. It turns out that it was the real Dionne Warwick much to Wick's embarrassment but she seemed to like being groped by him and remarked about how friendly the stores staff was.
 * Doctor Who: The Doctor
 * At the end of the 1999 Comic Relief Affectionate Parody Doctor Who and The Curse of Fatal Death, the Doctor regenerates into Joanna Lumley. His companion and fiancée Emma is disappointed as with him being "Not the man I fell in love with".... the Master, on the other hand....
 * In the "Who Can Bone More Women?" Contest on Kenny vs. Spenny, Kenny hires a pre-op transsexual to get all buddy-buddy with Spenny. Spenny racks up points like crazy until The Big Reveal at the end. He is not happy.
 * One episode of 1000 Ways to Die featured a rapist targeting a lady as she left a gym. As it so happens, the "lady" was a cross-dressing semi-pro boxer, who killed the rapist with one punch.
 * Inverted on Reno 911!: Dangle once had sex with a woman he mistook for a man in drag.
 * Done for revenge in Rab C. Nesbitt when Mary Nesbitt's sexually abusive boss is tricked into groping David Tennant.
 * CSI has had at least two murders traced to violent reactions to this trope.
 * CSI: NY had one as well.
 * Chicago Hope did it in the middle of its run when one of the doctors, a very manly hockey player, starts dating Mia Sara. When she informs that she has something to tell him, he says that he already knows... that she has fake boobs and he's fine with it, she informs him that she actually used to be his best friend and hockey teammate in high school.
 * There's Something About Miriam features a sexy lady called Miriam and a group of stud males trying to woo her attention. Except that Miriam is actually a pre-op Transsexualism - something the participants had no idea of but which the audience knew right from the start of episode one. The whole thing led to some of the competing men suing the TV network. And as one can imagine, transgender advocates were not thrilled at the show setting the movement back to the stone age.
 * Similarly(ish): post-op Transsexual Nadia Almeida, who won the fifth series of Big Brother UK didn't tell her housemates of her... "situation". Said Bridget was Dropped upon evicted housemates in her post-eviction interview, until LGBT right campaigners complained about five weeks into the game.
 * Arrested Development: Shows up in more than one context:
 * Invoked and subverted by Maeby, who wants Steve Holt to think Lindsay is her father, not her mother. She goes so far as to buy her mother a shirt with a label "in French":

"Barry: Hey, you’re not one of those silly men that’s dressed like a woman, are you? Prostitute: No, baby, I’m the real thing. (Barry floors it and drives away.)"
 * Barry Zuckerkorn apparently seeks out this trope, exclusively:

"Charlie:... and this will be the name of my biography"
 * One episode of Law and Order SVU involves a pre-op transsexual who appears female in every conceivable way except actual plumbing, who apparently killed a friend of her boyfriend's to prevent a public revelation. When the SVU team confront the boyfriend (ignorant of the fact that the boyfriend had no idea his girlfriend was biologically male), he runs in, grabs her by the groin to determine sex, and then runs out to commit suicide with an overdose of heart condition pills. It Got Worse. A judge then decides to send the extremely convincing transsexual to a men's prison because of her plumbing. She is promptly gang-raped and beaten. We are shown the aftermath, with her headed to a hospital, strapped to a gurney, basically a solid swollen bruise.
 * In an episode of Dark Angel, politically and socially conservative Normal discovers that his love interest is a trans woman. Unusually, he remains interested, but is dumped after she realizes she's a lesbian.
 * Bones: The subplot of an episode revolved around the team trying to figure out whether a Japanese assistant is a man or a woman. It is debated at some length before Angela figures it out in her own way.
 * Another episode has the team realize that the victim was a post-op male-to-female transsexual.
 * An episode of Diagnosis: Murder plays this straight (as it were). The victim was an MTF post-op TS, and Steve had been flirting with her before she was killed. To the show's credit, the victim was portrayed as a sympathetic character and none of the main characters freaked out about it. In fact,
 * Will and Grace: Jack freaks out when he gets turned on by the stripper at Leo's bachelor party, until he finds out the stripper is a pre-op who dances to raise money for her operation.
 * In Two and A Half Men, Charlie Sheen meets an old flame who has had a sex change and become Chris O'Donnell. He is freaked out by it but eventually comes to terms with the idea.

"Charlie: How was I supposed to know?" Alan: She had an Adam's apple the size of my fist and could palm a basketball."
 * Also a Running Gag is a certain Noodle Incident where he hit on a woman who later turned out to be a man. And from such statements it was pretty obvious but Charlie was too drunk to notice at the time.

"Chang: Winger, no date? Huh. Gaaaaayyyy."
 * A one-episode B-plot in Century City followed a lawsuit a man filed against a female-looking Hermaphrodite for causing him to question his sexuality. an in-universe ad for penis attachment surgery led to the observation that "someone should sue somebody for something."
 * Nip Tuck: In an early season, Matt starts a relationship with an older woman named Ava, much to the displeasure of his three parents. (Sidenote: It's f* ck'n' Famke Janssen! WHO WOULDN'T!?) Christian seduces her in an effort to get her to stay away from Matt and immediately deduces she used to be a man (and later describes her as "the goddamned Hope Diamond of transsexuals").
 * After Matt finds out about Ava and she has disappeared, he trolls bars until he finds an obvious transsexual, but as they start making out, Matt discovers she is pre-op and beats her violently.
 * Happens to Herb Tarlek on WKRP in Cincinnati twice (sort of):
 * In one episode, Herb starts flirting with a woman who claims she knew him in high school. While making out with her, he learns he did know her in high school... before she had the operation. She was a teammate of his on the high school football team, in fact the center to Herb's quarterback. To say Herb had a case of the Squick is putting it midly.
 * In an earlier episode, the trope is invoked and subverted by Johnny. To get Herb to stop hitting on Jennifer, he tells Herb "Our receptionist, the beautiful Jennifer Marlowe, is a result of the most cunningly successful sex change operation in the United States!" The ploy works... sort of.
 * Double Subverted in The IT Crowd when, in a B-plot, Douglas embarks on a successful relationship with a post-op transsexual woman—but it comes crashing down when he realises that she was saying "I used to be a man," not "I'm from Iran."
 * Community: Pierce has to be corrected as to the gender of the singer that made Hawthorne Wipes a gay icon. The same singer is seen later on, arm in arm with Chang, leading to this beautifully ironic line:

Music
"I grabbed her hair Came off in my hand And that beautiful girl Was just a beautiful man."
 * The music video for the song "Smack My Bitch Up" by The Prodigy does this to the viewer. It's a first person-camera accounting of a night of drunken carousing, drug use, and barhopping in which the protagonist gets into at least one fight with some guy, and molests a girl in a club, ultimately ending the night with a hooker. It's then revealed by a look in the mirror that the protagonist
 * "Well I'm not the world's most masculine man / But I know what I am / And I'm glad I'm a man / And so is Lola"
 * The second version of "Uneasy Rider", when the singer and his friend go into a gay bar and the friend goes off dancing with a lovely lady.


 * Used in this case to show how depraved the homosexuals are in the singer's eyes, and both preceded and followed by gay bashing, since one of the other patrons in the bar did flirt with him.
 * The Filipino song "Chicksilog" by Kamikazee is about a Ragnarok Online player's reaction to finding out the hard way that the "girl" his character hangs out with a lot turns out to be a Cross Player.
 * "When we got undressed it was big ol' mess/Sheena was a man!" - Tone Loc's "Funky Cold Medina".
 * The Doug Anthony All Stars song Sailor's Arms also has this theme.
 * Pet Shop Boys' "One thing leads to another". The protagonist gets drunk, picks up a woman in a bar, attempts to make love to her, and discovers she's has a penis. He drives off, confused, and crashes his car and dies.
 * The lead singer/guitarist of The Silversun Pickups has a very high register, causing a mild version of this for someone who hasn't seen them perform before.
 * One of Aerosmith's '80s comeback singles was "Dude Looks Like A Lady," with a line that goes, "say, love would be nice/ she's a love in disguise/ she had the body of a Venus/ Lord, imagine my surprise!"
 * Happened near the end of "Nobody Move" by Eazy-E
 * Ritsu Namine is a boy
 * This review of Placebo's Once More With Feeling
 * Biz Markie's "A Thing Named Kim": "She didn't look none like she looked across the room/She had big broad shoulders and her titties was big/They were filled with silicone, and her hair was a wig... So I hurried out and left, she said, "Please stay"/I said, "Sorry money grip, I don't go that way"/So I stepped out in a hurry, to gather my wits/And thought that's a damn shame, he had nice tits/And that's the last I ever saw of Kim/You wanna know why? Cause she's a he and her's a him." Needless to say, Markie didn't win many GLAAD awards for that one.
 * In a rare example that has nothing to do with appearance, most people are surprised to learn that Angela Gossow, the vocalist of Swedish band Arch Enemy, is a woman. Why? Well... just listen.
 * Most J-Pop stars utilize this trope as a way to gain fans. Notable examples include Miyavi and Gackt (though Gackt is quite competent at expressing his masculinity when need be). The latter was also a major inspiration for many of Tetsuya Nomura's character designs. The Crisis Core character, Genesis Rhapsodos was directly modeled after him.
 * And Hizaki.
 * It's also getting harder and harder by the month to tell what gender Miyavi really is (male).
 * Bou from An Cafe as well.
 * Just. Mana.
 * This is taken to its logical extreme by Piko, who has a known reputation as a "Ryouseirui" - aka, a trap singer. It's not hard to see why.
 * Leet Street Boys song: "Lady And The Trap".
 * "Luisa" by the Peruvian band Chabelos. It's about a guy who falls in love with a hooker called Luisa, and then discovers that "Luisa" is a transvestite, and he thinks that's hot.
 * In Wilfrido Vargas's "Macho Man", a guy falls for a pretty girl that he later finds out, while they are almost intimate, is a pretty boy; he freaks out and runs away, losing his shoes in the process.
 * In Rodney Carrington's appropriately named "I Think I'm Dancing with a Man" the singer begins to get suspicious of the woman he's been dancing with because of many masculine traits. His friend then takes "her" for a dance and "her" skirt falls off confirming it.

New Media

 * A common prank that people pull on the internet is to post a picture of a hot girl for everyone to oggle, only to reveal that the hot girl is really a very feminine man.
 * Some goons at Something Awful did this by making a female Myspace profile with the lone picture of some cleavage, later revealed to be a guy pressing his manboobs together.
 * Let's not forget all the hot women in the internet that are actually guys posing as women online.
 * Many online webcam pranks invoke this trope.

Print Media

 * Occured on a huge scale in an issue of Maximum PC with an advertisement. Sufficient numbers of people were surprised that the actor was male, that it was mentioned in the letter from the editor in the next issue. The ad in question featured Toplessness From the Back, but a very effeminate male.

Pro Wrestling
""Oh sweet Jesus she has a penis!""
 * WWE wrestler Mark Henry ran into this trope years ago when he found out that a lady named Sammy which he fancied really had a dick.

Tabletop Games

 * The Eberron setting of Dungeons & Dragons actually notes that this possibility of this occuring is one of the main reasons for the Fantastic Racism leveled against the shapeshifting Changeling race, whose members are fully capable of changing not just appearance but gender at will, regardless of the gender of their actual native form. It's a well known joke in Eberron fan circles to point to any depiction of an attractive male or female character and declare that it's really a changeling of the opposite gender.
 * While technically androgynous in the new fluff, Daemonettes from Warhammer 40,000 will play this trope on one of their victims just to watch them squirm. Because, yanno, that's what they do. (And then they gut their victims like pigs with their claws, which can go through Power Armor like a knife through butter.)

Theater

 * The play (and subsequent film) M. Butterfly is about a French diplomat who has an affair with a Chinese opera singer, unaware that she is a) a spy for the Chinese government and b) a man in disguise. This is, believe it or not, a case of Truth in Television: the play is partially based on the life of Bernard Boursicot.
 * This one's Older Than Steam because Shakespeare did it first. Someone falls for the Sweet Polly Oliver in both Twelfth Night and As You Like It.
 * In A Very Potter Musical, Dumbledore was dating Umbridge for a bit when he thought she was a man in drag. He was disappointed to discover the truth.

Video Games
"Raiden: YOU ARE THE WORST PRESIDENT EVER"
 * Bridget, the Wholesome Crossdresser teenage boy in a nun habit from the Guilty Gear series, and former Trope Namer. In Bridget's birth town there was a superstition that if twins of the same gender are born, disaster will come. Rather than let the town sentence him to death, baby Bridget's parents put him into the custody of the local convent's nun who raised him as a girl. Bridget's gender is never a secret in the game, at least not to the audience, and is spelled out right at the beginning of his storyline. He also never intentionally hides that fact (anymore; it's a long story), thus only a few characters actually get the unsettling reveal. The problem is that most other characters simply assume he's a girl, either because he's lived most of his childhood as one or because of his Moe Moe nun outfit.
 * Even Zappa from Guilty Gear XX has a Bridget dropped on him in Story Mode. As written in a letter to his mom (which he writes during his brief periods of lucidity), he says he found an injured young girl by the side of the road who he wished to make his wife. (He is unaware that he is the one who pounded her into the pavement). But when he attempted to pick her up and carry her, he finds...
 * At least he isn't in Johnny's shoes. That poor goon has a story mode ending about finding out too late that Bridget is a guy. ("I can't believe I hit on another man!")
 * Not to mention a little Yonkoma about Axl trying to hit on Bridget. Bridget gets fed up, grabs his arm and pulls it below the panel, with the word "TOUCH♡". The final panel has Axl gripping said hand with a horrified expression, going "What the hell did I just touch?". And "DESTROYED" in large letters above him, referencing the One-Hit Kill attacks from the games.
 * And now Hakumen got a Bridget dropped on him.
 * Over here in Real Life, people have found it quite amusing to show Bridget to those who aren't familiar with the Guilty Gear series, and get their reactions when they drop the bombshell, as it were (she and other characters of this trope are called "traps" for this reason). As the meme says, "Everyone is gay for Bridget".
 * And for the most famous female example, you have Sheik of The Legend of Zelda Ocarina of Time. Earlier in the game, Ruto called "him" a man. She was wrong. You know that you have an epic gender reveal when the fandom spends ten years starting Flame Wars over it.
 * Disgaea
 * This happens to Tink in Disgaea 2: Cursed Memories when he tries to hit on a Cute Monster Girl after joining your group. Of course, nobody bothered to tell him that the aforementioned "girl" is, in fact, Bridget's Lawyer-Friendly Cameo...
 * Also happens in Prinny: Can I Really Be the Hero?. The cute little Incubus is revealed in the hidden Monsterpedia section that "she's" a he.
 * The Alraune trap is brought back again in Disgaea 4: A Promise Unforgotten when the Cute Monster Girl in question is revealed as a guy in front of "her" adoring fans. Said fans decide that they "don't mind a little trap action."
 * In Dragon Age, it turns out that Shale was actually once a female dwarf. Thanks to The Fog of Ages, even the character in question is stunned by this, making it a rare case of the character in question experiencing the unsettling reveal.
 * In Metal Gear Solid 2, Raiden, a shameless Bishonen, is revealed to the President of the United States. The president literally grabs Raiden's package to check his sex, reacting in suppressed shock when he learns the terrible truth—the script says he'd misidentified him as the similar-looking female terrorist leader, Olga Gurlukovich, but Raiden's decidedly male voice and obvious bulge should have put that suspicion out the window. Besides, why didn't he just ask Raiden?... What was he planning to do to Olga?! Who voted for that?!
 * This comic offers another perspective.


 * According to an in-character Quinton Flynn, "Why would I even care? I'm not even anatomically correct! I run around naked and I got no junk!" ...That might say something...
 * In Fire Emblem 7, Serra is rather cold to Lucius when she thinks he's a girl in their C support, but when she finds out he's a guy, their B support has her going all starry-eyed.
 * It might be a trap for players to trap players who are expecting a Trap, but in ''Fire Emblem Awakening there is a masked man who claims to be Marth, and backs it up by wielding Marth's Legendary Sword. People already are very aware of Marth's gender at this point, right...? Turns out, this "Marth" is an imposter... and a girl. Yeah. Marth is a Girl. (You may now squee)
 * Flea from Chrono Trigger has confused generations of gamers with his/her claim that he/she is actually a guy, despite having obvious cleavage in the artwork. Not to mention the actual heroes, of course. Luckily Flea plays no role whatsoever in the story other than to be a Mini Boss.
 * Final Fantasy IV has a certain dancer in the town of.
 * Final Fantasy V. It's clearer in the original Japanese, where gender is reinforced by speech much more than in English. (For example, Japanese has gender-specific first-person pronouns, not that this stops some people.)
 * Final Fantasy VII: It's possible to get the Don to choose Cloud, in which case he reveals that he was in drag. While the idea of the Don picking Cloud over Tifa and Aerith may seem silly and unlikely based on the graphics in the original game (and their low polygon count), the Don's decision becomes much more understandable if one looks at Cloud's character design in Advent Children, especially if Cloud-in-drag appeared anything like THIS. Stupid Sexy Cloud.
 * In Fate Stay Night, there's a reason why Guinevere had that affair with Lancelot, since her husband, King Arthur, aka Saber, turns out to be a woman (and stopped aging at the age of 15), but Guinevere agreed to the marriage for political reasons. Which just strengthens the already present implication that Saber is is actually Bi the Way.
 * This also occurs in the Prequel series Fate/Zero, where Kiritsugu is quite shocked when he summons King Arthur and finds himself face to face with a young woman. While Saber initially thinks that it's because he's displeased by her sex, Irisviel explains that it's more than he's saddened because he realizes what Saber was forced to go through, including hiding her identity.
 * The Digimon series has played with Renamon's gender (or lack thereof) for some time, but Digimon World Data Squad amped it up by giving us a male Renamon with a painfully obvious female voice (in fact, it was the same voice actress who played Renamon in Tamers). Let's ignore the Unfortunate Implications of a male Sakuyamon.
 * The German fans must've been laughing hard at that one.
 * Shika in Kira Kira, when a guy fell in love with him when he was forced to cross dress. Two years later, he was shocked to realize that Shika was in fact male, but quickly got over it even offering to be his wife since the idea seemed to make him uncomfortable.
 * Iita in Blaze Union. Oh, ye gods, Iita. She's a perfectly adorable little Fille Fatale, cute and squeaky and very girly. Then night falls, and the other half of her Split Personality takes over—the side that is male, brash, Hot-Blooded, and downright thuggish. Her male half cheerfully announces to the stunned women of the game's cast that "oh right, sorry, I forgot to say: I'm a man at night". Equally shocking to people who first see Male!Iita and then realize that what they thought was a boy dressed in girl's clothes is actually still physically female.
 * Sting is all too happy to play with the latter situation, by the way; as is the norm, a number of Fan Service-y phone cards are being produced. One features Male!Iita smirking and slowly peeling the clothes off of his very female body.
 * While the title heroine of Atelier Annie has her moments due to her (unfortunate) Bifauxnen status, the game also gives a somewhat bizarre example when some men tried to hit on, of all people, Hans. The bizarre part is that they genuinely mistook him as a girl, while his co-workers in the Committee see him as a guy just fine.
 * Unsurprisingly, the Camwhore class in Forum Warz has this as a standard attack, if one not often seen. (It's down the line of a skill chain which many players respec out of before obtaining it.) Note that the gender, age and race of every player character is defined as "whatever happens to be squickiest at this instant". The same applies to any NPCs who use multiple or artificial personas, eliminating any potential shock value out of gender. (Especially as very few players would be attracted to most of the NPCs.)
 * Erica from Catherine is actually a post op Transsexualism. However, Vincent, Orlando and Jonny are aware of it, and there are several hints dropped over the course of the game before the actual reveal. It's only this trope to Toby, who lost his virginity to her.
 * Dark Souls has the Dark Sun Gwyndolin, the last born son of the Lord of Sunlight, Gwyn. Because of his lunar magic and association with the moon, he was raised as a girl.

Web Animation

 * Inverted in the "Blood Gulch Chronicles" seasons of Red vs. Blue with the character Tex, who is mistaken to be a guy, but is actually a woman to say the least. Played Straight with the character Donut, whose pink armor has gotten him mistaken for a girl, at least in the earlier episodes.
 * This joke was done as a gag during a scene where Hal is trying hit on women in episode 6 of Bowser's Kingdom.

Web Comics
"Artie: But honestly, I'm not sure what disturbs me more... the fact that this happened, or the fact that Chelsie is actually a boy."
 * Amber from Khaos Komix thought Nay was a Boy when she first met her.
 * In El Goonish Shive, this happens quite a lot when someone's stepped out of their normal gender. Somewhat unusually, it often gets milked for some drama in the process.
 * Justin and Susan almost do something they'd regret later while both gender-bent for Grace's birthday party. Good thing they didn't, since Justin likes guys; things would have gotten awkward once Susan became a woman again.
 * The "Sister" arc was full of this. Minor characters were falling at Elliot's feet, and that's before Ellen took on a life of her own.
 * The Wotch manages to do this to both participants, here when Jason is transformed into Satyr Sonja he has random flirty outbursts he can't control. When he "puts the moves" on Robin they both freak out. Jason continues to flirt-and-freak throughout the arc. And one flirt-and-freak recipient winds up wanting to date "Sonja" later.
 * Chapter 66 in Welcome to the Convenience Store.
 * Ghastly's Ghastly Comic:
 * A rather ridiculous case when the two similar-looking characters in the rather ambiguous fighting game (within a web comic) "Loli vs. Shota", both finally decide to actually check their genders... and are shocked to find out that they're both wrong on which one they thought they were. And yet even though we learn they're both wrong, the reader still is left in the dark about which character is which gender.
 * A Running Gag is that masculine characters tend to have sex with Freddy... who, despite having breasts, is male and revels in it. They tend to be very drunk at the time.
 * The Order of the Stick :
 * Averted very carefully by Vaarsuvius, an elf whose gender remains unspecified (and just to keep the readers guessing, the gender of is also unspecified and )
 * Subverted when Belkar hits on a magically gender-swapped Roy. Turns out, he knew it was Roy the whole time, and he was just doing it to squick him out.
 * Concession: Artie wakes up to discover he has trance, and confides in his boss:

"Torg: Aw, you think what you want. Riff: Can you jump up and down for us, mister?"
 * This strip of Something*Positive.
 * In this strip of Sluggy Freelance, Riff and Torg run into First Officer Brenas, a shapely woman who is actually the male of the species. Riff and Torg subvert the trope by not being bothered at all.

"Hatsuki:: I just had to go someplace new, didn't I?!"
 * Dan and Mab's Furry Adventures:
 * Dan infiltrates Twink Territories dressed as a woman. Later on, Biggs finds out. Quoth Biggs: "I'd probably feel more awkward if this was the first time this had happened..."
 * In another story arc, the shapeshifting incubus Abel takes a job working at the Lost Lake Inn. Dan gripes that it'll be an unfortunate adventurer who comes into an inn hoping for the traditional greeting and service by a perky cute beer wench. Abel: "Oh, well if THAT's your only issue..." Dan * turns around to see Abel has put on a very convincing female form* "YIGG!" Page caption: "Don't worry, adventurers are used to dealing with traps."
 * Later on Dan meets Mink, who is androgynously pretty, flat-chested, and runs around in a skirt and no shirt. Dan outright asks Mink whether they are a boy or a girl, only to find that Mink has forgotten hirself (being another shapeshifting 'cubi). Mink is on the point of taking a peak down hir skirt to refresh hir memory when Dan decides that he doesn't really need to know that badly.
 * Venus Envy has this happen to Lisa when she assumes that Chris is a male-to-female Transsexualism only to discover that he's actually just a Wholesome Crossdresser. Chris gets experiences this trope when he first meets Lisa and Zoe, assumes they're crossdressing boys as well, and grabs Lisa's breast while telling her it "looks totally fake". They beat him up.
 * Material Girl, in which the character the title refers to isn't really a girl.
 * This page, from Double K.
 * Used in Megatokyo early on, when Piro is reading through a section of girl's manga in a shop in Japan. A Japanese schoolgirl seems to think that Piro is a girl and is "cute". Her friend informs her that Piro is, in fact, a guy.
 * A double inversion of this trope occurs in Teh Gladiators, first when the Murlocs that join the heroes turn out to actually be female, and then when one of them, Yolanda, develops a crush on Vallant rather than vice versa.
 * Done in this strip of Head Trip.
 * Averted in Jet Dream, where the Elle-Boys of J.E.T. T.E.E.N., despite looking exactly like girls, make no secret of the fact that they're really boys (and, as a rule, heterosexuals who exhibit many "traditionally masculine" traits).
 * Reversed in Kevin and Kell. Rachel, upon first meeting Bruno, tries to romance him because she thought he was a sheep. To be more specific, not a male sheep. (Rachel's a rhino with bad eyesight, and had gone by the smell of the sheepskin Bruno was wearing, which was made from his girlfriend Corrie). The end result was Bruno added ram horns to the sheepskin so he's never mistaken for a girl again.
 * Done in this strip of Dueling Analogs, where one man mistakes a Bridget cosplayer for Rosette Christopher.
 * Alucard pulls this off as Girlycard in And Shine Heaven Now. Granted, the person he fooled is Bertie Wooster... And then many years later did it to Maggie Mui...
 * From Reversed, after a long overdue reveal: "What is this, Effin Trapsville?"
 * Happens to Pintsize in Questionable Content when he learns that the Anthro PC with whom he's been chatting is actually a male Anthro PC whose online icon happens to be pink.
 * Inverted and double-teamed in Roomies with Corey and Dave(ina).
 * Sexy Losers loves playing with this trope. Most notable is one comic in which a man picks up a woman with short hair at a bar, only to take her home and discover
 * Another Sexy Losers strip has one guy get a pregnancy scare from his girlfriend ("I'm not on the pill"), only for her to reveal she used to be a man.
 * Another has a man approach a suicidal woman whom he asks for a BJ before she jumps. After the act, he asks why she was going to jump. Turns out her parents disowned him for dressing up like a woman..
 * And a final one has a subway groper realize this.
 * Used in the NSFW comic Moon Over June, where the very lesbian Hatsuki accidentally hooks up with a man, who points out that he thought she knew since she picked him up in a transvestite bar.
 * Used in the NSFW comic Moon Over June, where the very lesbian Hatsuki accidentally hooks up with a man, who points out that he thought she knew since she picked him up in a transvestite bar.

Web Original
"Prof. Otaku: Well... wow, she really likes it in the butt. Hmm... Why does she... Oh."
 * The title Wholesome Crossdresser in The Saga of Tuck does this both when crossdressed and in his normal, baggy boy clothes. The latter tends to annoy him.
 * Awkward 4 has a flashback sequence of a series of Alex's ill-fated blind dates, one of whom is a man who stammers "Alex" in shock and quickly checks to confirm that, yep, that's an adam's apple before running for dear life.
 * On the defunct adoptable petsite Valenth, one of the NPCs was the person of intelligible gender of the week, Elliot Christoph. Considering many of the humanoid NPCs were like this, and all of them as such were men (plus the masculine name), many of the users expected Elliot to end up being male, referring to her as Sir Christoph and such. Elliot later was referred to as being female about twenty pages into the thread. The real kicker was the fact that she never bothered correcting them once. Lady looks like a dude indeed.
 * Desu Des Brigade: Professor Otaku admits in his Quick Hits review of Gravitation that he didn't realize Shuichi was male until he was halfway through an internet porn search of "her".


 * The Nostalgia Chick uses the Austin Powers "She's a man!" joke to express her doubts about Mel C being a real woman.

Western Animation
"Bug: Well, what didja expect in an opera? A happy ending?"
 * SpongeBob SquarePants: Patrick does this in the episode "That's No Lady" to everybody in the Krusty Krab, including Mr. Krabs and Squidward who had fallen for "her" after he tears off the girl disguise he was wearing.
 * In the surprisingly serious short What's Opera, Doc?, Elmer Fudd finds out that the girl he fell for was Bugs Bunny in a dress—and actually kills Bugs with his magic helmet. Although it's unclear whether he does it because Bugs is male, or if it's because Bugs rejects him the moment the disguise is off! Or because, well, he's Bugs.

"Joe: Taylor Hanson's a guy. Quagmire: Oh! Oh! Y-you guys are yanking me. Hey, hey, let's put one over on old Quagmire. Peter: No, he's actually a guy, Quagmire. Quagmire: W-well, this is insane! That's impossible! Oh, my God. Oh, my God! Oh, my God, I can't... Oh, God! I-oh, I got all these magazines. Oh G-oh God! Oh, God!"
 * Family Guy:
 * Pervert Glen Quagmire gets quite an unsettling revelation when he tells Peter and the gang that he loves Taylor Hanson from the 1990s band Hanson.

"Brian: And you had sex with two Filipino women. (sniffs again) And a man. Quagmire: You mean three Filipino women! Brian: (stares at him) Quagmire: ...Aaugh!"
 * Quagmire tends to get this trope fairly often. An episode where Brian is recruited by the force as a drug dog has Quagmire coming off a plane from Manila, where Brian comments:

"Zapp Brannigan: Honey! Wait! You didn't show me your surprise!"
 * In a similar vein, Brian was the subject of a B-plot where he was completely frustrated over the family really not seeming to give any sort of care at all to him. Rather than coming home, he goes to a hotel bar, meets up with a woman, and they intellectually hit it off. After quite a few drinks he goes back to her room, and the next day is telling Stewie about his conquest... Only for Stewie to realize that the woman he was with had all the correct parts now, but just a couple days ago was Quagmire's father; the main plot of the episode was the man going through a sex change operation and how everyone around was dealing with it. When Brian found out, he had an impossibly long vomit session.
 * The Cleveland Show has a moment in the Thanksgiving special wherein Cleveland gets revenge on his wayward and emotionally abusive father by not telling him that the "woman" he's about to get in bed with is actually a man (and totally not Tyler Perry / Madea). As it happens, the "woman" in question is actually Uncle Kevin, who disguised himself as a woman so Donna would have a positive female role model after her mother passed away. And then when Cleveland DOES tell him, it's not heard, but you see the two men gesturing... then the dad vomits for thirty seconds.
 * Futurama: There is the Valentine's Day episode in which Zapp Brannigan is on a blind date with a very burly man in drag, who leaves unexpectedly early...

""I did not mean for you to find out this way. But I suppose what's done is done...DETECTIVE!""
 * Also played with in Lrr (ruler of Omicron Persei 8)'s date with what he believes to be an Omicronian woman, who turns out to be a (human) cross-species dresser. He feels shocked and violated.
 * Batman Beyond sees Ra's Al-Ghul transferring his mind into his daughter Talia's body... and Bruce Wayne has quite the history with her (Well, as much as he does with anyone). What transpires thoroughly creeps both Bruce and Terry out.


 * In a later episode of King of the Hill, Peggy befriends a drag queen, after discovering "she" has size 16 feet like her.