%% Spoiler tags are not allowed in header quotes.

[[quoteright:350:[[VideoGame/GuiltyGear http://static.tvtropes.org/pmwiki/pub/images/guiltygearbridgetending.png]]]]

->''"Not her! Not her! She pees standing up!"''
-->-- '''Gary''', ''Film/BachelorParty''

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 DisguisedInDrag or a female [[SweetPollyOliver disguised as a male]] (sometimes even using [[LatexPerfection a realistic mask]] or a FullBodyDisguise), but whether the misunderstanding was intentional or not, due to RuleOfDrama, they ''will'' find out and it ''will'' be awkward, hilarious and possibly traumatizing for all involved.

This works equally well with straight people as it does gay ones.[[note]]{{Asexual|ity}}s--who wouldn't be interested either way--and [[BiTheWay bisexuals]]--who wouldn't mind either way--are usually immune to this trope, though.[[/note]] A straight female might be shocked to realize that hot guy she's been daydreaming about was actually a woman. Her male GayBestFriend, who was also daydreaming about the same guy (who is really a girl) will probably feel similarly. Almost always there is shock upon TheReveal, probably disappointment and maybe even disgust 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 IfItsYouItsOkay.

This is both a [[TheReveal 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 SweetOnPollyOliver, 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).

It's also worth noting that in many examples of this trope, it's not the ''gender'' (i.e., gender identity) that's a shocker, but the ''genitals''. One common example is that a straight man is attracted to a woman but finds out that she's transgender and has a penis. In RealLife, "trans panic" can have [[JustForFun/TelevisionIsTryingToKillUs violent or even lethal consequences]], as numerous trans people (mainly trans women) have been physically or sexually assaulted, sometimes even murdered, when their genitals are revealed.

Compare with
ShapeshiftingSquick, DudeLooksLikeALady, LadyLooksLikeADude, {{Bifauxnen}}, GenderBlenderName, SamusIsAGirl, FemaleMonsterSurprise, and IncompatibleOrientation. Often accompanied by AttractiveBentGender. Contrast JumpingTheGenderBarrier and ShesAManInJapan. A subtrope of GenderReveal.

Formerly called "Dropped A Bridget On Him", a play on the ''VideoGame/GuiltyGear'' character and the DroppedABridgeOnHim trope; references back to this title are still scattered around the site.

'''Spoilered pronouns are by definition [[Administrivia/SelfFulfillingSpoiler self-fulfilling]], so don't bother doing that.'''


* Happens in [[https://www.youtube.com/watch?v=AOfy4XHBy_0 this]] Japanese commercial for the Toyotah Auris, where a person who appears to be female walks down the aisle showing off their legs only to remove their coat to reveal a flat chest.
* [[https://www.youtube.com/watch?v=5FPKiTIH36E This ad]] for sushi delivery shop Gin no sara has a man's date reveal to be a man in drag after removing his fake breasts and washing off his makeup to scare a dog bothering him.

[[folder:Anime & Manga]]
* ''Manga/ShugoChara'': [[spoiler: Nadeshiko/Nagihiko]], whose family has a long-standing tradition of making [[spoiler:its boys dress, act, and, for all intents and purposes, ''be'' girls]] for about the first twelve years of their lives. [[spoiler:He had to repress all boyish desires, no matter how slight, and was forbidden from revealing his true gender to anyone.]]
* ''Anime/JubeiChan 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.
* ''Manga/SchoolRumble: Second Semester'' plays this straight at the end of the third episode. One of the characters present [[LampshadeHanging lampshades]] the moment beautifully.
-->"What... the hell?"
* In ''Manga/TheSecretDevilChan'': Kurosaki Sou discovers this about Devil-chan, after just 10 pages into the manga.
* Ship Leesoo from ''Webcomic/TowerOfGod'' finds out that the [[SuperPersistentPredator Bull]] is a female by kicking it in the groin to no avail.
* In ''Manga/LovelyComplex'', Otani has one when he learns that Seiko, the girl he was dating, is a transwoman. He's initially shocked upon the discovery and can barely face her for a few days, but he recovers and becomes friends with her.
* Happens to people of both genders in ''Webcomic/AxisPowersHetalia''.
** Everyone in the surroundings of [[WholesomeCrossdresser Chibitalia]] mistook him for a girl until he hit puberty. In [[http://moonyl00ny.deviantart.com/gallery/#/d2fzdmy this]] fan comic, Holy Roman Empire gets the Chibitalia bridge dropped on him.
** Hungary herself 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 [[ValuesDissonance 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 [[ClothingDamage notices that her blouse and armor are torn]] to AbsoluteCleavage levels, [[PleasePutSomeClothesOn much to his surprise.]]
** Also, Hong Kong used to be mistaken as a {{Bifauxnen}}, when in reality he's male.
** China. Then again, DudeLooksLikeALady and has [[Creator/YukiKaida 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. [[TheDitz Then again ...]]
** Germany referred to Kugelmugel as a boy, much to Liechtenstein's surprise, though she reacts with confusion over why he calls "her" a male rather than shock.
** 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 [[http://community.livejournal.com/hetalia/411243.html?thread=11932523#t11932523 when they're told that Himaruya is a male]] and experience their ''own'' unsettling reveal!
* This is a primary plot point in ''Manga/BlueDrop: Tenshitachi no Bokura''. The main character must [[AliensMadeThemDoIt 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 ''Manga/YuYuHakusho'' when they mistake Kurama for Kuwabara's pretty girlfriend. In the anime he's nonchalant and even jokes a little about it, but in the manga [[BerserkButton he gets homicidally angry.]]
* ''LightNovel/{{Slayers}}'':
** In the second season of the anime, during their tenure in a LadyLand kingdom for the [[OnceASeason cross-dressing episode]], a [[DraggedIntoDrag 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...[[CrowningMomentOfFunny and promptly takes all of her clothes off and reveals herself as a man]]. It turns out that all of the Royal guard was formed by guys in exactly the same situation: like Miwan, they were raised as girls by their moms to not being killed or taken away.
** 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.
* ''Manga/FruitsBasket'':
** Most of the Zodiac, plus Tohru, get a huge shock in the manga upon learning that [[spoiler:Akito, the head of the Sohma family]] is actually a girl but was RaisedAsTheOppositeGender.
** Tohru is also shocked to find out that Ritsu is actually a boy. She never would have known except for the fact that [[ItMakesSenseInContext he transformed into a monkey when they embraced]].
* ''Manga/FlameOfRecca'':
** 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 [[RuleOfThree three questions]], the third being "Are you a guy or a girl?". Aoi answers that he's a [[VillainousCrossdresser guy]], but instead of being stupefied about the gender, Recca merely brushes it off to mean that [[WouldntHitAGirl he can fight as he pleases.]]
* Asuta from ''Manga/KashimashiGirlMeetsGirl'', 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 [[SchoolgirlLesbians treated a lot more seriously]].
* ''Franchise/SailorMoon'':
** In the first [[Anime/SailorMoon anime]] 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 [[ShesAManInJapan Zoisite in the original Japanese version]] and the [[{{Macekre}} American dub]].
** Also, the Starlights (in the [[Manga/SailorMoon manga]]).
** In an early episode of the anime's R season, Mamoru and Usagi team up to take care of a baby named Manami whose mother is hospitalised after an attack from the MonsterOfTheWeek. When they change the baby's diapers, it turns out Manami is a boy and not a girl; he has a GenderBlenderName and had been referred to with gender-neutral pronouns. (The dubs generally handle it by referring to the baby as a girl first, and then as a boy.)
* Happens in the anime ''Manga/GirlsBravo'', 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.
* ''Franchise/DotHack'': Given that the entire series is based on a fictional MMORPG, there are plenty of {{GIRL}}s around.
** In ''Anime/DotHackSign'', Tsukasa is the Bridget that gets dropped on ''herself''. Among the initial worries that come with [[TomatoInTheMirror a revelation like this]] is that her gender will affect her relationship with Subaru. Turns out, [[IfItsYouItsOkay it didn't matter]].
** It also happened in ''.hack//Roots'' when two female players attacked Haseo and their voices change.
* The audience of ''VisualNovel/OtomeWaBokuNiKoishiteru'' gets the main character Mizuho's gender dropped on ''them'' -- if they [[LateArrivalSpoiler didn't read the series synopsis]] before watching the first episode. Most of them, [[StupidSexyFlanders mortified at having cheered at the fanservice]], firmly invoked the FirstLawOfGenderBending in their minds.
* The relatively obscure manga and animated movie ''Manga/TheyWereEleven'' 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 ArrangedMarriage imposed by their family.
* ''Manga/HayateTheCombatButler'':
** 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 [[http://manga.redhawkscans.com/reader/read/hayate_no_gotoku/en/0/325/page/14 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 ([[VisibleSilence ...]]). 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 [[MegatonPunch Megaton Kick]].)
* Ban and Ginji actually try peeping on the very girlish-looking Kazuki in a hot spring in an episode of ''Manga/GetBackers'', mistaking him for a girl at a distance. Later, Amon Natsuki hits on him and tries to pull an IKissYourHand. Juubei merrily skewers them both times.
* In ''Anime/{{Vandread}}'', Bart Garsus gets a Bridget dropped on him with TheReveal that BC is a GenderBender [[TheMole Mole]]. In the end, [[JumpingTheGenderBarrier 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 [[MarsAndVenusGenderContrast living on completely different planets]] -- so same-sex "loves" were common practice.
* Jan Suk in ''Manga/{{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 [[spoiler:''[[VillainousCrossdresser Johan]]''.]] Also counts for the viewers, as it's a ShockingSwerve. [[spoiler: Johan had been impersonating his [[HalfIdenticalTwins twin sister]] as part of a plot to make her question her sanity, and his disguise and behavior were convincing enough that even the audience doesn't suspect the truth.]] The eventual reveal has caused anime clubs to riot.
* ''Manga/{{Naruto}}'': During the Land of Waves StoryArc, Naruto meets Haku, whom he takes for a girl ([[DudeLooksLikeALady Not that]] [[WholesomeCrossdresser this is]] [[CrossdressingVoices hard]]), and Haku corrected him on this assumption right before he left.
-->'''Haku''': Oh, and by the way? I'm a boy. [goes away]
--> '''Naruto:''' No way?! He's prettier than Sakura!
* Happened to Karin in ''Manga/KamichamaKarin'' 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.
* ''Manga/ShamanKing'' has Amamiya Ryu aka Bokuto no Ryu, who thinks that Lyserg Diethel is a girl at first. When Lyserg reveals his gender, Ryu can't believe it until Lyserg either lets him check in his underwear (anime) or drops his pants in front of everyone (manga). [[IfItsYouItsOkay Ryu doesn't seem to care]] and remains very protective and devoted to Lyserg [[spoiler: even after Lyserg's FaceHeelTurn and defection to the X-Laws]].
* Alto Saotome from ''Anime/MacrossFrontier'', a former Kabuki actor who often played female roles, gets this a lot... but trust us, [[BerserkButton 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 [[HandsomeLech Mikael]] loves to jerk Alto's chain by referring to him as "Princess Alto" and similar nicknames.
* ''Manga/WanderingSon'':
** This happens to Riku Seya, a classmate of the Nitori's older sister Maho and her eventual boyfriend. Seya saw Nitori 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 Nitori's, "Mako-chan" (no, not [[Manga/MinamiKe that one]]) also revealing herself as biologically male. Seya is left rather confused by it all but they eventually become friends.
** The series has had a few instances of the rare {{Trans|gender}}masculine case too. For example, Shiina originally mistakes his ([[MistakenForPedophile adult]]) girlfriend to be cheating with Takatsuki. He grabs his groin but notices he's biologically female. After it all clears up, Takatsuki and Shiina become good friends.
** On the first day of middle school Chizuru goes to school in a gakuran and is mistaken for a boy until her best friend berates a girl for doing so. Chi often screws with the schools uniform code, be it wearing a tie instead of a ribbon or just outright crossdressing.
** It's implied that Yuki knew Takatsuki was a trans boy, but she didn't realize Nitori was a trans girl. Neither of the two knew Yuki was a trans woman. The characters get a bit surprised at the reveals.
* ''Manga/RurouniKenshin'':
** VillainousCrossdresser Kamatari drops this 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; in the anime he ''does'' reveal his gender too, but without flashing anything.
** Kenshin himself often causes this with viewers, and the fact that he's [[CrossDressingVoices voiced by a woman in the original Japanese]] makes it worse (and legend has it that the character designer for ''VideoGame/GuiltyGear'' first came up with the character Baiken after making this mistake) and he's in fact based on a historical samurai, [[http://en.wikipedia.org/wiki/Kawakami_Gensai 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.
* Subverted in the adult manga ''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. ItMakesSenseInContext.
* ''Manga/OuranHighSchoolHostClub'':
** 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 Subver|sion}}ted 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 DragQueen 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 ''Anime/GlassFleet'' when Holy Emperor Vetti Sforza finally manages to get Michel Volban, the leader of LaResistance, into his clutches... and, upon drugging Michel in order to have his way with him, discovers that Michel is actually a [[WholesomeCrossdresser woman]]. Vetti seems rather put out about it.
* ''Manga/RanmaOneHalf'':
** The reverse happens to Akane at the very beginning of the series. She wasn't exactly thrilled to [[NakedFirstImpression find out]] that the shy and awkward girl she had just made friends with was actually [[GenderBender a guy]].
** A subversion: Hiroshi and Daisuke's discovery that the cute [[HeroesWantRedheads 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'' MasterOfDisguise (which includes crossdressing as a girl) is not pretty.
*** One little thing to note here: in his usual mood, Tsubasa even sounds like a girl. The first hint to viewers that something's off about "her" is that, whenever he gets angry, his girly impression slips and he talks in his usual deep voice. Not that anyone in the show has taken notice of that...
** 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 [[WholesomeCrossdresser Ukyô]]. Then a stray bomb goes off, blows apart Konatsu's outfit, and reveals "she" is a very [[DudeLooksLikeALady feminine-looking]] "he". Ukyô is just as stunned as everyone.
* A rather bizarre example occurs in ''Manga/FistOfTheNorthStar'': 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.
* ''Manga/OmamoriHimari'' did this recently with a side character. Right after [[ClingyJealousGirl Rinko]] mentioned about her having two more rivals... {{lampshade|Hanging}}d by Himari.
* In ''Anime/{{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 ''Literature/TheCountOfMonteCristo,'' who lured Albert into Vampa's trap.
* The main premise of 80s series ''Manga/StopHibariKun''. 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 she is actually biologically male. Hilarity ensues.
* Classic example: [[DudeLooksLikeALady Shun]] from ''Manga/HereIsGreenwood''. He's used for a prank because of this, and the reveal (more rage-inducing than unsettling) comes when he's caught in front of a urinal.
* ''Anime/FullmetalAlchemist'': Happens to Greed in one OVA in which he flirts with "Winry" who is actually the shapeshifter Envy, who is male in this version.
* ''Anime/CowboyBebop'':
** 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 MythologyGag to when Ed really was a boy in the original version of the story before being changed to a girl for cast balance.
** A downplayed version-[[spoiler:Gren]] is a male with female breasts due to being used for drug testing.
* The appropriately-titled ''Manga/NoBra'' centers around a guy who finds out that his ForgottenChildhoodFriend Yuki is actually a guy, despite [[http://static.tvtropes.org/pmwiki/pub/images/NoBra0302C.jpg what he looks like]].
* Happens once in ''Manga/PlusAnima'', 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 ''Manga/KodomoNoOmocha'' has a subplot where one of Sana's friends develops a crush on an [[SempaiKohai upperclassman]] tennis player. When she confesses her love, the object of her crush explains that she's a girl.
* ''Manga/RoseOfVersailles'':
** In the anime the Duke of Orleans tried to invoke this by having a very girlish and young-looking henchman impersonate UsefulNotes/MarieAntoinette, thus ruining the marriage to the Dauphin. It doesn't work, since Oscar manages to stop him and Marie shows up in time.
** Also tends to happen fairly often that [[{{Bifauxnen}} Oscar]] herself is mistaken for a ''gorgeous'' man, only for Oscar or someone in the known to clear the mistake and unsettle the poor woman. Note that this did ''nothing'' to stop the creation of a rather large [[EvenTheGirlsWantHer all-female fan club for Oscar]]...
* Lesbian variant: In the first OVA of ''Anime/ElHazardTheMagnificentWorld'', 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. In ''The Alternative World'', the real Fatora tries to return the favor to Alielle, but instead finds Alielle's [[HalfIdenticalTwins very similar twin brother]]. "It just went... squish."
* ''LightNovel/AndYouThoughtThereIsNeverAGirlOnline'' plays with this quite a lot:
** Two years prior to the start of the series, protagonist Hideki proposed to a female MMORPG player who then revealed herself to be [[{{GIRL}} a man in real life]], causing him to believe that ThereAreNoGirlsOnTheInternet. Partway into the series, it's revealed that the player actually ''was'' a woman in real life, and was merely invoking this trope to avoid unwanted male attention, so the show manages to pull this off twice with the ''same character''. Admittedly, part of the reason Hideki was unsettled by the second reveal was because the woman in question turned out to be [[spoiler:his ''high-school teacher'']].
** The best interesting part is during the offline meet where Hideki meets Ako in real life for the first time. When you look at the entire Alley Cats Guild online, you may assume that Ako's is the only female player. But the truth comes out when during the guild's first offline meet, it turns out that Hideki's the only male player in the guild. Turns out that his other two "male" guild-mates, Schwein and Apricot is actually his classmate Akane Segawa and the StudentCouncilPresident Kyou Goshouin. Guess this anime really fits the title.
* ''Manga/PrunusGirl'': 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.
* ''Anime/MobileSuitGundam00'': 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, [[WordOfGod the people making the show]] claimed Innovators have no sex. They actually meant that they were androgynous. It was just badly translated and underwent MemeticMutation before the correction came around. He doesn't make it any easier in the 2nd season, when it's shown that when it's needed, he ''can'' really fill out a ballgown. Maybe [[Anime/{{Gravion}} 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 ''Manga/TheDayOfRevolution'' [[GenderBender 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 ''Manga/FamilyCompo''. The main character moves into his aunt and uncle's place and finds out they're both transgender. There are some other trans and crossdressing instances as well.
* In ''Manga/{{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 [[HilariousInHindsight "Who's my favorite pussy?"]] in the English dub... HilariousInHindsight or GettingCrapPastTheRadar?
* In episode three of ''LightNovel/KinosJourney'', a Bridget was dropped on all the audience members who thought [[AmbiguousGender Kino]] was [[spoiler:a boy]]. The ones who guessed right didn't hesitate to pat themselves on the back.
* In ''Manga/MariaHolic'' 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 StupidSexyFlanders moments.
* Azami in ''Anime/{{Himawari}}''. "Wait... [[StupidSexyFlanders the hot one]]?"
* In the Creator/ArinaTanemura manga ''Manga/TheGentlemensAlliance'', 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.
* ''Manga/PokemonAdventures'':
-->'''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''.
* Another Bugsy example happened in ''Manga/PokemonGoldenBoys'', another adaptation of ''VideoGame/PokemonGoldAndSilver''. 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.
* ''Anime/{{Pokemon}}'':
** In the anime, [[LovableSexManiac Brock]] wound up subverting this on one occasion. He knew something was wrong when a ridiculously HotScientist ''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 [[InexplicablyIdenticalIndividuals Jennies]] by the same lack of a RagingStiffie.
** And then later he accidentally hits on [[AmbiguouslyGay Harley]].
** He also failed to realize that Anabel/Reira was a {{Bifauxnen}}.
-->'''Brock:''' Hey, you're not changing with Ash and me? Is it because of May?\\
'''Anabel:''' No, it's because even if I don't look like the part... I'm a girl.
** Brock also sometimes falls for Ash whenever he [[DisguisedInDrag 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 ''Manga/{{NEEDLESS}}'' after rescuing a crossdressing Cruz.
* When [[IdolSinger Kouji]] [[TheCasanova Nanjo]] from ''Manga/{{Zetsuai 1989}}'' was a young boy, he once saw a rage-filled, beautiful {{tomboy}} named Izumi. He fell in love with her [[LoveAtFirstSight 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 ''[[TroubledButCute Takuto]]'' [[TallDarkAndSnarky Izumi]], as the young girl that captivated him, since "Izumi" was the kid's ''surname''. After quite some {{Gayngst}} about it, Kouji decides [[IfItsYouItsOkay that he doesn't care]], [[HaveIMentionedIAmHeterosexualToday he doesn't like men that way]], [[SingleTargetSexuality but... it's *Izumi*, dammit.]] Besides, [[StarCrossedLovers it]] [[TheMasochismTango would]] [[BigScrewedUpFamily soon]] [[{{Wangst}} get worse]].
* Himemaru in ''Manga/RappiRangai''. Despite being born male, he decided to become a [[{{Ninja}} 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.
* ''Manga/DetectiveConan'':
** 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 [[HarmlessLadyDisguise "she" is a man]].
** Much later, Conan, Hakuba and Heiji realize that the "Detective of the South", Natsuki Koshimizu, is a {{Bifauxnen}} instead of a waifish boy. They only find out when [[SheCleansUpNicely she puts on]] [[{{Joshikousei}} her school uniform]]... a feminine ''[[http://en.wikipedia.org/wiki/Gakuran#Sailor_outfit seifuku]]'' instead of a male ''[[http://en.wikipedia.org/wiki/Gakuran#Gakuran gakuran]]'' like the one Heiji has just put on. (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 ActionGirl Sera Masumi appears. Conan, Ran and Sonoko don't find out that the [[TroubledButCute 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.
** In manga chapter 830, it comes up ''again''. Sera is such a {{Bifauxnen}} that even [[spoiler: Kaitou Kid]] mistakes her as a boy. [[spoiler: ''After having knocked her out and stripped her down to her boyish underwear and shirt to steal her clothes''.]] Said person doesn't find out until Conan explais it to him, [[spoiler: and when that happens [[DynamicEntry a VERY upset Sera returns and kicks him to the face]].]]
* A mild version pops up in ''Manga/HowIBecameAPokemonCard''. Akira and his best friend Akari, a {{transgender}} boy, 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".
* In ''Anime/AkahoriGedouHourLovege'' episode 9, the son of a businessman that Kaoruko is babysitting (the kid, not the businessman) ends up being a girl, much to Kaoruko's dismay.
* This happens to Wataru Takatsuki in ''Manga/YubisakiMilkTea'' in recent chapters. However, despite Yoshinori Ikeda's initial beliefs to the contrary, Wataru actually likes him even more.
* A RunningGag with Aoi Futaba from ''Manga/YoureUnderArrest'', a {{Transgender}} woman whose gender issues are portrayed fairly realistically:
** Her in-canon introduction involved this trope, along with her new co-workers' reaction to the reveal.
** She invokes the trope deliberately in an episode of the anime, when she gets a marriage proposal from an IdolSinger that she's not interested in. Aoi asks for a meeting and shows up in male clothes, telling him about her issues. The guy respects Aoi's wish, withdraws the proposal, and they decide to stay friends.
* In ''Anime/HeartcatchPrettyCure'', Tsubomi quickly becomes smitten with the handsome StudentCouncilPresident Itsuki. When she learns that "he" is actually [[{{Bifauxnen}} a handsome girl]], she's upset and shocked enough to end up staying home with a fever.
-->'''Tsubomi''': O...[[{{Ojou}} Ojou-sama]]?!
** Cobraja ends up choosing Itsuki to be a Desertian (mostly) because he thinks she's a beautiful man. Then when Itsuki-as-a-Desertian swoons over a girl's uniform and reveals her actual gender, he promptly freaks.
** Also it's implied that before all these happened, Erika also had the same unsettling experience and stayed home with a fever like Tsubomi.
* Years later, Ichika Usami of ''Anime/KiraKiraPrecureALaMode'' ends up falling head over heels for Akira Kenjou, whom she doesn't realize isn't a boy. ''[[TheDitz Not even when Akira turns into Cure Chocolat right in front of her]]'' (to be fair, [[PrinceCharming Cure Chocolat]] is one handsome Precure when transformed). It takes the end of the episode and Ichika's dad pointing it out for her to realize what's going on.
-->'''Ichika:''' You're... you're a womaaaaaaaaaaan?!
* Natsume Takashi from ''Manga/NatsumesBookOfFriends'' tends to get mistaken for his [[IdenticalGrandson grandmother, Reiko,]] by Youkai on an almost constant basis. One of these Youkai is Hinoe, who ''[[LesYay really]]'' liked Reiko and DoesNotLikeMen. She gets as far as groping Natsume's non-existent breasts before she learns her mistake.
-->'''Hinoe:''' ... ''Where are your boobs!?''
* In chapter 279 of ''Manga/AirGear'' while fighting Agito, Shalott reveals to Agito that he is actually a guy ([[GagPenis 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 ''Manga/SakuraGari'', we have a boy named [[spoiler: Youya]]... better known as [[spoiler: Sakurako Saiki]]. This is ''not'' PlayedForLaughs as [[spoiler: s/he is an [[JerkAssWoobie insane, thoroughly broken]] {{Yandere}}, who ends up DrivenToSuicide.]]
* ''Manga/BlackButler'': 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.
* ''VisualNovel/TogainuNoChi'': Rin, a [[DudeLooksLikeALady 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!"
* ''LightNovel/{{MM}}'' has Tatsukichi himself. The CrossdressingVoices helped out a lot. Taro then gets disappointed since his crush on the first episode, is his cross-dressing friend.
* ''Manga/PrincessJellyfish'':
** In the first episode Tsukimi allows a woman who helped her to sleep in her all-female dorm. The next morning Kuranosuke is revealed to be male when he wakes up with disheveled clothes.
** This is subverted several other times. Tsukimi's friends, who are afraid of men, fail to notice that Kuranosuke is male even when they find out he pads his bra (they assume he's just ''very'' small chested).
* PlayedForLaughs with Karara's debut in ''Manga/SgtFrog'': Tamama spends the entire episode flitting between jealousy at the thought of being replaced as the platoon's cute tadpole and being charmed by the new 'recruit's' [[HeroWorshipper Hero Worship]] of him. Then, when Karara heads home, ''she'' promises to become a good future bride for him...
* In ''Manga/{{Aphorism}}'', this is how Hinata and Mino met for the first time. [[HoYay Hinata even had a crush on him for a while]]: his reaction at the Bridget-dropping was [[{{Squick}} throughly expected]].
* In ''Adolescence of Utena'', the ''Anime/RevolutionaryGirlUtena'' 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 [[WouldHitAGirl continues to attack her]].
* In ''Manga/{{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 ''Manga/KarakuridoujiUltimo'', Service, who up till then was the source of much ViewerGenderConfusion, got his shirt blown off during a fight in Chapter 23, revealing... a flat chest. We next see [[TheHero Yamato's]] face with an expression of pure shock. The fandom was mind-blowned too.
* In ''Anime/DigimonXrosWars'' episode 28, it's revealed that Cutemon, the two-foot-tall, pink, scarf-wearing [[TheMedic Healer]] of Team Xros Heart, is a boy. [[spoiler:Boys dont cry!]]
* In episode 6 of ''LightNovel/{{Kampfer}}'', Natsuru inadvertently does this to [[spoiler:Mikoto]] when his identity is compromised. Apparently, his clothes only change during transformations if [[GenderBender he/she]] is wearing the Seitetsu Academy uniform.
* ''Manga/IonoTheFanatics'': Well, [[GirlsLove 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.
-->'''Iono:''' Who would have thought even a dedicated skirt chaser like me could have been fooled.
* Subverted in ''Manga/WildRock''. Yuuen [[DisguisedInDrag dresses up as a girl]] for a HoneyTrap plot, but eventually feels guilty and upset that Emba is [[LovesMyAlterEgo 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.
* ''Manga/IceRevolution'' is one long series of dropped Bridgets after martial artist and extreme {{Tomboy}} (so extreme her hairdresser likens her to a fellow {{Transgender}} person) 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 ''Anime/NyanpireTheAnimation'' seconds after developing a crush on him. In a later episode, he fantasizes about marrying him and even get's jealous of seeing him drinking blood from Nyatenshi.
* PG version in ''Manga/CardcaptorSakura''. When Sakura, Kero and Tomoyo have to catch a Clow Card that has taken residence in a painting, they meet with a kid named Yuuki whose DisappearedDad is the artist who painted it. At the end of the episode Yuuki's NiceHat falls off and reveals ''very'' long RapunzelHair, thus showing the trio (and us) that Yuuki is a tomboyish girl.
* The "tomboyish girl wears a NiceHat and TheReveal happens when the hat's dropped and you see her long hair" also happens to Kunimitsu Tezuka from ''Manga/ThePrinceOfTennis'', when he meets Miyuki Chitose. Except it's GirlishPigtails instead of RapunzelHair.
* Much to the shock of the heroes of ''Anime/SamuraiChamploo'', this is not the case with the [[MachoCamp 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 ''Manga/{{Patalliro}}''. Fans are shocked to find out that the shounen-ai author is a happily married man with three kids.
* In ''LightNovel/MayoChiki'', 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 OrdinaryHighSchoolStudent 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 ''VisualNovel/{{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. In an OVA, [[spoiler: Jun temporarily does become a "full-fledged" girl]]
* The backstory of ''Manga/{{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''.
* ''Anime/CodeGeass'': 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. However, this is unsettling to us... but the person they're there to assassinate is fine with Lelouch being a boy. As long as it's pretty...
* In the ''Manga/DNAngel'' manga Satoshi once went DisguisedInDrag and Dark [[HoYay almost kissed him]] before he realized he's a guy.
* In ''Manga/{{Moyashimon}}'', a certain cute goth-loli attired girl is not all she seems. Oikawa goes on a rampage when this is revealed to her after she witnessed a kiss. [[spoiler:It turns out the ElegantGothicLolita wearing character is actually Kei Yuuki, a biologically male character who was PutOnTheBus several chapters in. She also seems to [[ChildhoodFriendRomance like the protagonist]].]]
* Prostitute Haru from FireCandy, 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 ([[http://static.mangatraders.com/view4/45806/797882de6c65e46feea0d1fa1ab831e6.jpg often already past the point when it would be just disturbing]]) 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).
* ''Anime/HanaukyoMaidTai'': Taro's maids (except the one who convinced him to dress up like a maid) got really shocked.
* ''Manga/{{Sazanami Cherry}}'':
** When Ren reveal himself to be a crossdresser the protagonist is confused at first however [[IfItsYouItsOkay gets over it]] and dates him.
** Ren gets one of these from [[spoiler:''his own sister'']]. [[spoiler:His sister]] is considerably older than him and he didn't know she was {{Transgender}}.
* In ''Anime/IxionSagaDT'', Kon instantly becomes attracted to the hot maid Mariandale... until she's revealed to be a {{Transgender}} woman. Whenever she reverts to her original male voice, he's creeped out.
* In the beginning of episode 5 of ''Manga/ServantXService'', Yamagami woke up from being drunk and saw a woman that looked suspiciously like her coworker Yutaka Hasebe [[BedmateReveal next to her]]. The latter then said she was indeed [[LastNameBasis Hasebe]] and asked Yamagami to hide it from their coworkers, causing the latter to go BlueWithShock. As it turned out, it was {{subverted|trope}}. Hasebe brought Yamagami to his sister Kaoru's apartment, and it was Kaoru who was sleeping next to Yamagami--and [[TheGadfly messing with Yamagami for fun.]]
* Happens to a larger percentage of the school in ''LightNovel/InfiniteStratos'' when [[spoiler: Charlotte]] reintroduces herself.
* In ''Manga/KingdomHeartsII'', Sora finds out that [[{{Disney/Mulan}} "Ping"]] [[{{SweetPollyOliver}} is female]] by accidentally getting a glimpse of her breasts while both are washing up at the lake. [[GirlsHaveCooties His reaction]] to TheReveal is priceless, especially if you compare the scene with the one from the [[VideoGame/KingdomHeartsII game]], where he and Donald find out via Goofy.
* ''Manga/MonthlyGirlsNozakiKun'':
** Wakamatsu is subject to this in Chapter 45. While spending time with the girls while they're swimsuit shopping, he assumes that Kashima is a boy, and it isn't until the very end that he's informed otherwise.
** The stinger of episode 8 of the anime reveals that this happened to Hori, with regards to Kashima. When they first met, Hori assumed that Kashima was a boy, despite the obvious signs indicating otherwise, like that she wears a skirt with her uniform. It wasn't until he saw her head to use the ''girls[='=]'' bathroom that he realized she was a girl.
* In ''Manga/ICantUnderstandWhatMyHusbandIsSaying'' Hajime hooks up his friend Miki with his younger sister. Said friend was not aware of the fact that said younger sister is actually Hijime's [[BigBrotherAttraction clingy]] cross dressing younger brother.
-->'''Miki''': Your sister has a palm tree and coconuts! Arabiki... elephant... wiener! ***k o* destiny!
* In ''LightNovel/DateALive'' Shido poses as a girl to get close to the man-hating Miku. When she discovers he's a boy she sets several ''thousand'' mind-controlled people to hunting him down for punishment.
* The episode of ''{{Anime/Kochikame}}'' in which Maria is introduced. His real name is Ai Asato and he became a woman after falling in love with his old coach, who looked a lot like Ryotsu. When Ryotsu himself meets Maria, he immediately falls in love with Maria, up to the point of marriage. Luckily Ryotsu manages to realize in time that Maria is a man, by accidentally feeling Maria's private parts.
* Tenma in ''Manga/KamisamaNoIutoori'' is revealed to be a boy when Akashi solves a puzzle by finding a mannequin that most closely resembles Tenma; all the other mannequins were women, while the solution was the male mannequin.
* ''Anime/MichikoToHatchin'':
** Hatchin is only ten and has BoyishShortHair for most of the series. More than a few people mistake her for a boy.
** One episode has Hatchin meeting a soft-spoken looking girl her age. When his father leaves he reveals himself to be a {{jerkass}} and then reveals himself to really be a boy when he pulls up his dress. Bebel crossdresses because he wants to get into travesty acting like his dad.
* Tetsuo from ''Manga/{{Yuureitou}}'' is a trans man. It's always PlayedForDrama when he comes out. He's stated that in the past women have gotten mad at him when he does.
* ''Manga/{{Adekan}}'': Anri and Shiro, both being effeminate {{Bishonen}}, have gotten people to think they're woman. In one scene, Shiro is walking in a public bath house and the men around him ogle him thinking he's a woman. When they get a look at his chest they're confused and horrified.
* ''Manga/HatsukoiZombie'' starts with one: the NewTransferStudent in chapter 1 has the same name and face as the girl the protagonist Tarou liked as a child. Turns out he's a very male boy who used to dress as a girl because of his mother's weird tastes. [[spoiler:Except not really. She really is a girl, but decided to pass as a guy because she didn't want any more boys to fall in love with her: she can see "first love zombies", and wasn't too fond of seeing multiple, scantily clad versions of herself floating in the air.]]
* Kimino from ''Boku to Boku'' is asked out on a date by a shy looking girl named Asou. She doesn't like girls but goes anyway. At the end of the date Asou reveals that he's a boy. He's revealed to be a boy when Kimino accidentally sees him peeing in the bushes, though the other WholesomeCrossdresser Yuuki says he already guessed it. Asou transfers to Kimino's school but is an AbhorrentAdmirer because Kimino likes her other friend, Josei, and because Asou is a CovertPervert.
* Despite being an OtokonokoGenre deconstruction featuring several crossdressers, this doesn't really occur much in ''Manga/BokuraNoHentai'':
** One day at school Marika (who was still living as a boy) is grabbed by a female student and gets asked if she's "a drag queen". Marika is uncomfortable by the question until the 'girl' reveals himself to be a boy named Satoshi. He crossdresses constantly and even several classmates don't realize his gender. He stops crossdressing by his second year because he hit a growth spurt and couldn't fit into his sisters hand-me-down anymore.
** Trans girl Marika invokes this when at a SchoolFestival. She was having worries about her gender and entered a crossdressing competition by saying she was a crossdressing boy. [[spoiler:She won it.]]
* ''Manga/AiNoShintairiku'':
** This happens to Naruse when he accidentally feels up Sara on the train. He falls for her by the end of the series and doesn't care that she's transgender.
** This occurs to Sara's entire class when Sara is ForcedOutOfTheCloset by her teacher.
* Chizuru from ''Manga/KimiToBoku'' mistakes the [[DudeLooksLikeALady feminine looking]] Shun for a girl when he sees him in the gym uniform. Even when the others tell Chizuru otherwise he doesn't believe them. Chizuru doesn't acknowledge that Shun is male until he sees him in his school uniform for the first time, which causes him to faint.
* Episode 5 of ''Anime/{{Punchline}}'' reveals the fact that [[spoiler:Yuuta]] is biologically female to the girls. It isn't until later that it's revealed [[spoiler:that he is a boy named Pine who bodyswapped with Chiyoko years ago]].
* ''Nise x Koi Boyfriend'':
** In the first story of ''Nise x Koi Boyfriend'' this occurs to the protagonist with his own boyfriend. He saw a girl and asked her out. It turns out his 'girlfriend' was actually a boy from his school crossdressing. Satoi didn't intend for that to happen. He thought Soutarou ''knew'' he was crossdressing and realized who he was. When Soutarou learns who his boyfriend is he becomes mad at Satoi because he thought it was a prank. [[BiTheWay He doesn't mind dating Satoi]] after learning Satoi honestly liked him.
** Two men tried to pick up Satoi without realizing he's a crossdresser. When they do learn they act violently, though Soutarou helps save Satoi.
* In ''Manga/DragonBall'', Krillin tries to hit on Upa, then gets embarrassed when Goku tells him Upa is a boy.
* ''Anime/{{Devilmancrybaby}}'': [[spoiler:Ryo/Satan]] reveals a fully male and female body [[spoiler:when he adopts his beautiful, angelic true form. Since angels are both sexes and since this is Netflix we get to see the dick and everything.]] Of course, the characters (and possibly viewer) have too much on their mind at this point to really say anything so it goes unremarked on for the whole show.
* ''Mnemosyne'': [[spoiler:Big bad Apos's]] reveal as being intersex has some truly ominous implications. [[spoiler: Your sex governs your powers in Mnemosyne's setting so Apos gets a full shot of everything and then some.]]

* Doug Stanhope: "[Transvestites nowadays] are ''good!'' You don't even have to pretend you got tricked any more!"
* Patton Oswalt claims this is his favorite reason to watch ''Cops'', even going so far as to give a name to the duped person's reaction: "The Transvestite Revelation Face".

[[folder:Comic Books]]
* Even Creator/DCComics' woman-lovin', homicidal, AntiHero 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''." [[MeaningfulName Lobo and everyone reading now knows what the name "T.V." stands for...]]
* In ''ComicBook/{{Camelot 3000}}'', Tom Prentice awakens memories of Camelot in Sir Tristan's reincarnation, who happens to be a [[GenderBender gorgeous young woman]]. Tom's [[LoveAtFirstSight instant crush]] on the reborn Tristan plays out this trope. [[spoiler: Ultimately it proves hopeless, as Tristan refuses to accept life as a hetero female, eventually entering a lesbian relationship with Isolde's reincarnation.]]
* In ''ComicBook/{{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 [[BuryYourGays humorously]] as most RealLife examples of this trope.
* Between ComicBook/XMen characters Scott, Jean and Warren in ''ComicBook/{{Marvel 1602}}''. 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.
* Creator/GrantMorrison's ''ComicBook/{{Zenith}}'' had the title character propositioned by Metamaid, an attractive {{Transgender}} 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.
-->'''Zenith:''' TNT Tom left with a smile on his face, mind...
* Klara Prast of the ComicBook/{{Runaways}} was appalled when Xavin suddenly transformed from a tall white guy to a pretty black girl during their first encounter. She got over it, eventually.
* One Creator/ECComics story features human astronauts being forced to land on an uncharted planet to repair their ship. Commander Morrison falls for a beautiful female native and [[IChooseToStay chooses to stay]] and marry her. Things go well, if a bit strangely, at first, but soon his new wife starts changing, cutting her hair short, losing her curves and spurning his advances. Morrison investigates, and comes to realize to his shock that the natives are biologically similar to snails. [[spoiler:When he gets back home, his brand new ''[[GenderBender husband]]'' expresses his hopes that Morrison will hurry up and change, so things can get back to [[IncompatibleOrientation normal.]]]]

[[folder:Comic Strips]]
* Used, of course, in ''ComicStrip/LibertyMeadows''. 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.
-->'''Dean:''' Damn hippies...
* ComicStrip/{{Garfield}} thinks a cat is a "cute chicky-boo" in [[http://www.gocomics.com/garfield/1980/11/30 the strip here]] until he realizes it's a cat he knows, named Frank.

[[folder:Fan Works]]
* Freeza did this to Krillin in ''WebVideo/DragonBallZAbridged''. Later, [[spoiler:Dodoria]] did this to ''everyone''. [[spoiler:Granted, part of the joke is [[ShesAManInJapan she's a man in the original series..]]]].
* In ''Machinima/FinalFantasyVIIMachinabridged'', Cloud ''attempts'' this after [[DisguisedInDrag crossdressing to gain an audience with]] [[DirtyOldMan Don Corneo]], but...
-->'''Cloud:''' I have a dick.\\
'''Don Corneo:''' (''gasps'')\\
'''Cloud:''' Surprise! I'm a guy!\\
'''Don Corneo:''' ''[[DepravedBisexual Even better!]]''\\
'''Cloud:''' Whaaaaaaa-
* A slightly different version used in the sequel to ''Theatre/AVeryPotterMusical'': 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 Franchise/SpiderMan 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 [[AccidentalPervert on top of him]].
* The anime and cartoon crossover parody/deconstruction blog ''Blog/BeochanPaiseanAgustAifeala'' did this with [[spoiler: '''[[WesternAnimation/ItsTheGreatPumpkinCharlieBrown The Great Pumpkin of all people]]''' turning out to be a cute little girl Linus has a crush on, much to the jealously of Sally]].
* In the ''Anime/PuellaMagiMadokaMagica'' fancomic ''FanFic/ThanksKyubey'', [[spoiler: a emotionfied Kyubey is turned into a human. Mami and Sayaka hoped Kyubey would be a hot male. They are not amused when Kyubey turns into a {{Moe}} girl]].
* A literal unsettling ''gender'', as opposed to sex, reveal in ''FanFic/{{Hivefled}}''; one of the many sources of Gamzee's current trauma is that his [[AbusiveParents bloodlink]]'s offhanded comments about Gamzee being feminine got him seriously thinking about his gender identity for the first time in his life and realising that he actually ''is'' genderqueer, though he doesn't currently know there's a word for it.
* In ''[[Fanfic/TheRacketRotterChronicles The Racket-Rotter Chronicles]]'', [[spoiler: Annette discovers The Builder has become a woman. In turn, the others find out The Twin has also become one.]]

[[folder:Films -- Animation]]
* In ''WesternAnimation/TheBoxtrolls'', [[spoiler:after Snatcher reveals himself to be Madam Frou-Frou, Lord Portley-Rind has a horrified look on his face and states "I regret so much"]].
* Francis the ladybug in ''WesternAnimation/ABugsLife'' has to constantly reveal his true sex. And given he's voiced by Creator/DenisLeary, he does it in the most caustic way possible.
-->'''Francis''': SO! Bein' a ladybug automatically makes me a ''girl''! Is that it, flyboy?!
* The Soothsayer in ''WesternAnimation/KungFuPanda2'' is initially mistaken for a man by Po due to her beard (she's a goat).
* In ''{{WesternAnimation/Robots}}'', during the climax
-->'''Madame Gasket''': Who are these losers?\\
'''Fender''': We, sir--\\
'''Madame Gasket''': I'm a ''woman.''\\
'''Crank''': Ouch. (''Diesel's eye lenses break'')
** Helps that the ugly lady in question is voiced by Jim Broadbent
* Played for laughs in ''Disney/TheLionKingIISimbasPride''. Timon and Pumbaa declare that they're gonna show Simba's new son how to have fun at his unveiling. Rafiki corrects that that it is a girl and the two promptly double take at that.

[[folder:Films -- Live-Action]]
* Handled much more realistically in possibly the most famous example, [[ItWasHisSled Fergus and Dil]] from ''Film/TheCryingGame''. Subverted in that, even after finding out about Dil, Fergus realises that [[IfItsYouItsOkay he still loves her]]. For most, this is AllThereIsToKnowAboutTheCryingGame.
* Madmartigan's performance in ''Film/{{Willow}}''.
--> '''Lug:''' Not a woman?
--> '''Madmartigan:''' ''(To soldiers)'' Gentlemen...
--> '''Lug:''' ''Not a woman!?''
--> '''Madmartigan:''' Meet Lug.
* In ''Film/AceVenturaPetDetective'', Ace Ventura figures out that [[VillainousCrossdresser detective Lois Einhorn]] is actually AxCrazy 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 {{Squick}}ed. [[BrainBleach 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 {{Squick}}ed. 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") [[spoiler:Roger Podacter also found out, presumably during an intimate encounter with Einhorn, and as Ace declares during the reveal, that's why he wound up dead; "He found Captain Winkie!"]]
* ''Film/TheAssociate'': 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 [[LatexPerfection well-disguised]] Ayres.
* The ending to ''Film/SomeLikeItHot'' has "Daphne" revealing his true identity to the millionaire who is about to marry "her". [[SubvertedTrope His response]] [[Funny/SomeLikeItHot is priceless]].
* In ''Film/WithoutAClue'', Reginald Kincaid (playing Sherlock Holmes) is quite attracted to [[spoiler:a woman impersonating]] Lesley Giles. [[spoiler:The real]] Lesley Giles [[spoiler:, who has been abducted,]] is a man who habitually dresses as a woman. [[spoiler:After Giles is rescued,]] "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 ''Film/{{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 ''Film/BladesOfGlory''. 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?"
* [[spoiler:Tanya]]'s silhouette reveal as (possibly?) a joke in ''Film/TheNakedGun 33 1/3''. The DVD commentary revealed it was a stand-by and they were going to use [[spoiler: a hairy butt instead]]. 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 ''Film/WildZero'', 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:
-->'''Guitar Wolf:''' ACE! Love has no borders, nationalities, or genders! DO IT!!!
* As you can guess by its title, ''Film/VictorVictoria'' 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 ''Film/{{Tomboy}}''. Laure is [[spoiler:forced to don a dress and her mother makes her apologize to the boy she fought earlier]]. She also goes to visit [[spoiler:her girlfriend, thus making the reveal to her too]].
* In ''Film/TheHangoverPartII'', [[spoiler:Stu discovers he slept with a MTF prostitute. [[{{Pun}} "You're in Bangkok, sweetie, there's a reason they don't call it Bang-cunt."]]]]
* The CultClassic horror movie form the 80s, ''Film/SleepawayCamp'' sets this up as a big reveal. [[spoiler:Angela, the main character and murderer, was really Peter, Angela's twin brother. Susie and Ronnie are ''mortified'' when they find out the truth.]] A rare instance where the trope is played for horror. ''WesternAnimation/RobotChicken'' even had a sketch about it!
-->'''WebVideo/TheCinemaSnob:''' [[spoiler: ''That's a dick.'']]
* A prime example of this occurs in ''Film/INowPronounceYouChuckAndLarry''. While at an LGBT party, Chuck (Creator/AdamSandler) hits on a [[CurvesInAllTheRightPlaces curvacious]] playboy bunny whom he thinks is Creator/JessicaBiel, but is actually a cross-dresser [[FanDisservice played none other than by]] Creator/DavidSpade.
* In ''Film/RatRace'', Owen drives a bus full of ''Series/ILoveLucy'' fans dressed in Lucy costumes. One of them asks for a pit stop as the bus' bathroom door was broken.
-->'''Owen''': So? You ain't got nothin' these other Lucys haven't seen before! \\
'''Lucy''': [in a deep voice] Not necessarily.
* In ''Film/GoodLuckChuck'', Chuck discovers that one of the many women he's been sleeping with to help them find their true loves was formerly his classmate - and a man.
* In ''Film/{{Surrogates}}'', the beautiful lady surrogate that was killed alongside the inventor's son via feedback weapon, turns out to be an over-weight man. Considering that each person is usually allowed ''one'' Surrogate, it means this guy has been going around as a woman for quite some time.
* The Extended Version of ''Film/TheHobbitAnUnexpectedJourney'' has a funny example. At the Rivendell dinner party, Kili begins eyeing up some of the elven maidens, causing Dwalin to shoot him a glare. Kili defends himself by saying that elven women aren't that attractive [[note]]too thin, creamy skin, high cheekbones and not enough facial hair[[/note]], but curtly points out that the one walking past him isn't too bad. Dwalin leans in and says "that isn't an [[{{Elfeminate}} elf]] ''[[{{Elfeminate}} maid]]''" and the entertainer turns around... Kili has an OhCrap moment as the other dwarves laugh at him.
* In ''Film/MabelsBlunder'' (1914), Mabel's boss hits on her--only to find out that it's her brother disguised in her clothes.
* ''Film/TheTigerMakesOut'' - the antihero protagonist is scheming to strike out at an indifferent world by abducting and dominating a beautiful woman. He's mesmerized by a sultry cabaret singer, who he follows to the dressing room, never noticing the lobby sign advertising a female impersonator performance.

* There is a pornographic story that was [[GenderNeutralWriting 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 [[TomatoSurprise a revelation to the reader]].
* Done with a twist in the ''Literature/{{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 ''Literature/SirAproposOfNothing'' novel, ''Tong Lashing'', the revelation that evil crime syndicate leader (and Apropos' brief lover) Verah Wang Ho is a man leads to his (anti)HeroicBSOD which ends with [[spoiler:the Hiroshima-like destruction of the city they're all in]].
* This is how the plot for ''Literature/OutOfPosition'' starts. Devlin Miski, a straight football player, starts having sex with a crossdresser, then finishes even ''after'' he reveals he's male, causing him to question his sexual orientation and way of life.
* Another similar incident like the one above happens in ''Jake's List'', where the main character is seduced by a crossdresser and spends the rest of the novel dealing with a large amount of {{Gayngst}}.
* In the Neil Gaiman short story "Changes", all possible reactions to this are explored as a drug allows quick, easy sex-changes in a few hours. The few people in story who can always tell someone's birth gender, well, the one shown is the subject of severe violence when she denies entrance to certain clubs (this was her job).
* A variation of this happens to Ivan Vorpatril in Creator/LoisMcMasterBujold's ''Literature/ACivilCampaign'' 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 [[GenderBender fellow with the black beard]] accompanying the Vorryuter Armsmen and why do his [[OhCrap eyes look so familiar]]?
* In the novel ''Literature/{{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 ''Literature/MoonOverSoho'' 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 [[SuddenlySexuality turns out not]] to bother him, because in his own words...
-->"We were having so much fun I thought, 'why stop?'"
* In ''Literature/LetTheRightOneIn,'' Oskar finds out that [[spoiler: Eli is actually a castrated boy.]] 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 [[spoiler: Abby is probably is an actual girl]].
* In German novel ''Gottes Bodenpersonal: Eine unwahrscheinliche Liebesgeschichte'', the protagonists are a hooker and a Christian preacher who gets on her nerves by trying to proselytise her customers (without much success). When one of the johns finds out the hooker is actually male, he freaks out and attacks him. Enter the preacher guy, who only heard fighting noises, and now attacks the john. After the police arrived, the preacher kneels down beside the unconscious hooker, sees "her" skirt ride up, and ... covers the hooker's private parts with his jacket. As he had no intention to have sex with the hooker, "her" gender is of no consequence to him. [[spoiler: It turns out he's gay, and actually very attracted to the man behind the hooker mask.]]
* In ''Literature/{{Ringu}}'', Sadako appears to be a supernaturally beautiful woman but is a hermaphrodite with fully formed testicles. When the last carrier of smallpox tries to rape her he discovers this, freaks out, kills her, and throws her down a well.
* In ''Literature/GettingPersonal'', three friends place personal ads for each other. They don't manage to find the person one of the trio met and was attracted to, which is revealed to be because she was a woman (although whether this is just a reveal to the audience/her friends, or whether she didn't realise either, is left unclear).
* ''Literature/SongAtDawn'':
** It happened to Estela and Dragonetz individually concerning the same person: [[spoiler:Sanchez]], one of Alienor's Ladies in Waiting.
** Dragonetz was crusading and saw some thugs about to rape a woman after killing her husband. They ripped open her dress and the surprise they found was great enough for Dragonetz to kill them with ease.
** Discovering the same thing was part of Estela's 'initation', so to speak, into Dragonetz' inner circle.
* In ''[[Literature/SomewhereBeneathThoseWaves Amante Doree]]'', English spy Horatio Quentin falls in love with the beautiful pro-French courtesan-spy Annabel St. Clair, only to discover during a romantic interlude that she is {{Transgender}}, although she still [[IncompatibleOrientation loves]] him.
* In ''Literature/AllMenOfGenius'', the revelation that "Ashton" is actually Violet (having disguised herself in order to attend the men-only scientific academy she's at) comes as rather a shock to the two people romantically entangled with him/her, though both get over it. Violet's non-romantic friends are pretty relaxed about it.
* It's mentioned in ''Literature/TailchasersSong'' that neutered males can be mistaken for females.
* Subverted in Lidya Charskaya's ''A Brave Life'', a fictionalized biography of Nadezhda Durova, one of the most famous examples of SweetPollyOliver. When Nadezhda is staying at a Polish officer's residence in her soldier guise, the officer's sister Zosya forms a crush on "Alexander". Nadezhda, unable to get away from the enamored girl, reveals the truth Ė and Zosya is very glad because she yearns more for a sister and a confidant than for a lover. Later the girl remains friends with Nadezhda and is shown as blissfully happy in a PerfectlyArrangedMarriage.
* The ''Franchise/StarWarsExpandedUniverse'' explains that Tatooine's Tusken Raiders only ever remove their body wrappings in the presence of their immediate family if young, or their spouses if married. The tribes try to keep good records of who's under those wraps when it comes to arranging marriages, but mistakes can happen, leading to some very unhappy wedding nights.
* Near-future thriller ''Literature/{{Victoria}}'' subjects the villainous [[AntagonisticGovernor Governor Hokem]] to this, with two attractive effeminate homosexuals dressing up as party girls and getting him into a compromising position, resulting in blackmail and ultimately the end of his administration.

[[folder:Live-Action TV]]
* ''Series/AllInTheFamily'': In the 1975 episode "Archie the Hero," Archie [[KissOfLife saves the life]] of someone named Beverly [=LaSalle=], who he thinks is a highly attractive woman ... only to realize (upon being told) that Beverly is a cross-dressing man. (Beverly had passed out in the back of Archie's taxi cab.)
* ''Series/TheJeffersons'': Twisted in the 1977 episode "Once a Friend" Ė Louise actually has this when a highly-attractive woman named Edie comes to visit George. George also experiences this when he doesn't immediately recognize Edie ... and both are in for quite a shock when they realize Edie was once a man named Eddie (the man George knew during his service in the Navy).
* Korean drama ''Series/TheFirstShopOfCoffeePrince'' 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.
* ''Series/KamenRiderDouble'':
** The heroes use Wakana as bait to attract the Liar Dopant. [[spoiler: Of course they couldn't really put Wakana in the line of fire. It's Philip in a dress and wig.]]
** Also Akiko is one of the male-seeming bodyguards.
** In ''Film/KamenRiderXKamenRiderWizardAndFourzeMovieWarUltimatum'', Series/KamenRiderWizard meets a beautiful young woman while inside her Underworld[[note]]the "mental realm" all people possess[[/note]] and they seem attracted to each other; when he gets back to the real world, the young woman is revealed to be the CampGay owner of Haruto's favorite donut shop. While there are elements of the trope's pure form (the Owner says "[[DudeLooksLikeALady When I was younger, I was often mistaken for a girl]]"), for Haruto it's more of an Unsettling '''Identity''' Reveal.
* The KoreanSeries ''Series/YouAreBeautiful'' has a convent novitiate [[WholesomeCrossdresser dressing]] like her twin brother to join a pop band. And the drummer was the last to figure it out...
* In the episode of ''Series/QuantumLeap'' [[http://www.hulu.com/watch/63211/quantum-leap-what-price-gloria---october-16-1961 What Price Gloria]], Sam uses this trope to enact revenge on his (female) [[FreakyFridayFlip 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 ''Series/CoryInTheHouse,'' it happens to Newt Livingstone when Cory [[DisguisedInDrag poses as his sister Raven]] (for reasons too convoluted to get into here) and Newt [[AttractiveBentGender falls for him]] despite "her" clearly being [[WigDressAccent his best friend in a dress and a wig]]. Then again, WigDressAccent was a staple of ''[=CITH=]'''s parent show ''Series/ThatsSoRaven'', and [[TheDitz Newt is very stupid]].
* Another sexuality-inverted instance occurs in an episode of ''Series/ThirdRockFromTheSun'', in which a [[GirlOfTheWeek Guy Of The Week]] dumps Sally when he finds out, to his dismay, that she ''isn't'' a guy in drag.
* ''Series/{{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. [[spoiler:Then learns that she is actually the missing embezzler.]] Afterward, Kate rarely missed an opportunity to remind Tony of the incident.
* ''Series/{{JAG}}'': In "Retrial", a sailor had unbeknownst to him hired a transgender prostitute. When finding out, the sailor changed his mind and the prostitute threatens him with a knife. The sailor defends himself and accidentally stabs the prostitute and runs away in fear and shame.
* Happened once to Sanchez from ''Series/TheCloser''. He made the mistake of [[spoiler: hitting on (and kissing) a pretty female witness...who turned out to be the perp in drag. In a somewhat darkly humorous twist, this was the incident that convinced him to start actually going to the mandatory therapy sessions with the department shrink. (Mandatory due to the fact that he was still suffering from PTSD after taking the bullet in the previous season finale; up until this incident, he'd been in denial about it.)]] Poor, poor Sanchez.
* ''Series/{{Farscape}}'' episode "The Flax" D'Argo discovers that [[spoiler:the scavenger Staanz]], who appears to be a rather ugly male, turns out to be, in fact, a female of her species, and is "considered quite the looker". This becomes Squick material for D'Argo when [[spoiler: Staanz announces her attraction to him]]. Briefly lampshaded at the end when a shaken Crichton asks Aeryn if she's actually a woman (which she is).
* Parodied(?) in an episode of ''Series/CelebrityJuice''. Host KeithLemon, in the episode following "Let's Dance for Comic Relief", in which he was a competitor with dancing partner PaddyMcGuinness, opened the show saying that said partner got off with 'Roberta' Webb- only to discover 'she' had a 'tallywhacker'. 'Roberta' being Robert "[[Series/ThatMitchellAndWebbLook Mitchell and]]" Webb, another competitor who [[http://www.youtube.com/watch?v=5Lz6k5Zg2wA performed "Flashdance" in a leotard and frizzy wig]].
* Inverted in an episode of ''Series/TheDrewCareyShow'' 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 store's staff was.
* ''Series/DoctorWho'':
** The Doctor [[spoiler:actually manages to do this to himself after his regeneration into Creator/MattSmith]].
** At the end of the 1999 UsefulNotes/ComicRelief AffectionateParody ''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". [[JumpingTheGenderBarrier the Master, on the other hand]]....
* In the "Who Can Bone More Women?" Contest on ''Kenny vs. Spenny'', Kenny hires a transwoman 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 ''Series/OneThousandWaysToDie'' 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 ''Series/{{Reno 911}}'': Dangle once had sex with a woman he mistook for a man in drag.
* Done for revenge in ''Series/RabCNesbitt'' when Mary Nesbitt's sexually abusive boss [[http://youtube.com/watch?v=xB-M_tYhLGU is tricked into groping]] Creator/DavidTennant.
* ''Series/{{CSI}}'' has had at least two murders traced to violent reactions to this trope.
* ''Series/{{CSINY}}'' had one as well.
* ''Series/ChicagoHope'' 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 {{Transgender}} - 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): {{Transgender}} woman Nadia Almeida, who won the fifth series of ''Series/BigBrother UK'' didn't tell her housemates of her... "situation". Said Bridget was Dropped upon evicted housemates in her post-eviction interview, until LGBT rights campaigners complained about five weeks into the game.
* ''Series/ArrestedDevelopment'': 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":
--->'''Maeby:''' "[[ItIsPronouncedTroPay It's pronounced 'Shemalé'.]]"
** Barry Zuckerkorn apparently ''seeks out'' this trope, exclusively:
--->'''Barry''': Hey, you’re not one of those silly men thatís dressed like a woman, are you?
--->'''Prostitute''': No, baby, Iím the real thing. (Barry floors it and drives away.)
* One episode of ''Series/LawAndOrderSVU'' involves a {{Transgender}} woman who appears female in every conceivable way except her 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 is trans), 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.\\\
A judge then decides to send the her 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 ''Series/DarkAngel'', 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.
* ''Series/{{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. [[spoiler: The character is a man...the actress is a woman.]]
** Another episode has the team realize that the victim was a {{Transgender}} woman. [[spoiler:This had absolutely nothing to do with the murder.]]
* An episode of ''Series/DiagnosisMurder'' plays this straight (as it were). The victim was a trans woman, 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, [[spoiler: she was killed by her former military buddy because he was {{squick}}ed, and the murderer is portrayed as a JerkAss]].
* ''Series/WillAndGrace'': Jack freaks out when he gets turned on by the stripper at Leo's bachelor party, until he finds out the stripper is a trans woman who dances to raise money for her operation.
* ''Series/TwoAndAHalfMen'':
** Charlie meets an old flame who has had a sex change and became Bill. He is freaked out by it but eventually comes to terms with the idea [[spoiler: until his mother starts dating his ex]]. And Alan's reaction when he starts seeing the similiarities in him and Jill is even funnier:
-->'''Alan:''' (''sees a picture of Jill'') She's cute. Very tall. Broad shoulders- '''HOLY MOTHER OF GOD!!'''\\
'''Charlie:''' Welcome to the [[Film/TheMatrix Matrix]].\\
'''Alan:''' So, s-s-so Jill is, i-is-\\
'''Charlie:''' Yep.\\
'''Alan:''' And, a-a-a-and you and Jill used to-\\
'''Charlie:''' Every chance we got.\\
'''Alan:''' A-A-And Mom is-\\
'''Charlie:''' At this very moment.\\
'''Alan:''' (''looks at the picture once more'') '''HOLY MOTHER OF GOD!!'''
** A RunningGag is a certain NoodleIncident 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.
-->'''Charlie''': How was I supposed to know?"
-->'''Alan''': She had an Adam's apple the size of my fist and could palm a basketball.
* A one-episode B-plot in ''Series/CenturyCity'' followed a lawsuit a man filed against a female-looking {{Hermaphrodite}} for causing him to question his sexuality. [[spoiler:The case was dropped when he turned out to be a trans too, but]] an in-universe ad for penis attachment surgery led to the observation that "someone should sue somebody for something."
* ''Series/NipTuck'':
** Matt starts a relationship with an older woman named Ava (played by Creator/FamkeJanssen), much to the displeasure of his three parents. 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 a non-passing trans woman, but as they start making out, Matt discovers [[BerserkButton she is pre-op]] and beats her violently.
* Happens to Herb Tarlek on ''Series/WKRPInCincinnati'' 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... [[OldFriendNewGender 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.
* DoubleSubversion in ''Series/TheITCrowd'' when, in a B-plot, Douglas embarks on a successful relationship with a trans woman who [[DefiedTrope insists on coming clean on their first date]] -- but it comes crashing down when he reveals that he wasn't really listening and [[DoubleSubversion thought she was saying]] that she was from Iran, not "I used to be a man."
* ''Series/{{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 [[CasanovaWannabe Chang]], leading to this beautifully ironic line:
--> '''Chang:''' Winger, no date? Huh. ''[[FailedASpotCheck Gaaaaayyyy.]]''
* In one episode of ''Series/{{House}}'', a beautiful teenage model appears to be female, but turns out to have Complete Androgen Insensitivity, with her symptoms being caused by a tumor on one of her undeveloped testicles. She is horrified to discover this, as is her manager[=/=]father, with whom she had been having sex. House's response to the manager's horror is priceless:
-->'''House:''' Oh, sure. ''Now'' it's creepy.
* An attempt to use this trope using a real-life trans person caused some controversy among the LGBT community in an episode of reality show ''Series/CakeBoss'', where Buddy invites Carmen Carrera (best known for being on ''Series/RupaulsDragRace'') and sets her up on a date with "cousin Anthony", the punchline being the reveal to Anthony that his date was "really" a man, with his shocked reaction PlayedForLaughs. Though usually thought of as a DragQueen, since she was one before she started transitioning, Carmen is actually a transwoman and was ''not amused'' when made aware of the nature of her appearance on the show, [[http://www.huffingtonpost.com/2012/06/12/cake-boss-carmen-carrera-transphobic-joke_n_1591366.html citing the fact that this has led to real life murders of trans people]]. Buddy later apologized for the incident and the episode was removed from rotation.
* On ''Series/{{Friends}}'', Ross reminisces about how he and Chandler once tried to pick up women in a bar. Apparently, he was unsuccessful, while Chandler ended up making out with his conquest. Monica comments that such behavior for Chandler would be highly unusual. Ross agrees that Chandler isn't the type to go to bars and make out with ''girls''...
* ''Series/{{Casualty}}'' once featured two patients from a car crash: a girl and her strangely high-pitched voiced boyfriend. The doctors realised the boyfriend needed a chest examination. This revealed what certainly wasn't a boy's chest.
* In ''Series/{{Miranda}}'', a chap complimenting large-boned Miranda on her dolled-up appearance ("You look amazing. You totally pass!") is thoroughly embarrassed to discover that she ''really is'' a woman, and is unwittingly ''dressed'' as a transvestite.
* One TitleSequence of ''Series/ThreesCompany'' shows [[CasanovaWannabe Larry]] getting into the same bumper car at an amusement park with who looks like a long-haired woman from the back. Then the bumper car turns around and the viewers ([[BehindTheBlack and Larry]]) discover that this "woman" has a mustache.
* A semi-common event on ''Series/TheJerrySpringerShow'' is a trans woman or man coming out as trans to their boyfriend/girlfriend/spouse. The person being told [[FreakOut rarely reacts well]], oftentimes because they're angry that they weren't informed sooner, feeling like their partner was lying to them or deliberately hiding information. Given this it's unsurprising that most of these events end with the spouse breaking things off with the transperson, sometimes due to IncompatibleOrientation, other times due to no longer feeling like they can trust their partner if they were willing to hide something so major.
* The first episode of the second series of ''Series/{{Blackadder}}'' inverts this trope. The episode opens with a beautiful but poor young woman named Kate deciding to disguise herself as a boy to find work and support her ailing father. She finds a job as Edmund's manservant, and the two fall in love over the course of the episode while he tries desperately to cognitively reframe the feelings he's having for another man. The relief he feels when she reveals her true gender is immense.
-->'''Blackadder:''' Then come, kiss me, Kate!
* PlayedForDrama with Blair and Drew on ''Series/DeadOfSummer''. Blair, who is gay and suspects that Drew is a closeted homosexual, tries to strike up a relationship with him, telling him about the importance of [[BeYourself being yourself]]. When he finds out that Drew is also {{transgender}}, however, [[spoiler:[[{{Hypocrite}} he wants nothing to do with him]] and is squicked out at the fact that he had kissed a boy who was biologically female. He later feels terrible about it, apologizes and they eventually make up.]]

* The music video for the song "Smack My Bitch Up" by Music/TheProdigy 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 [[spoiler:is actually a hot chick herself.]]
* "Well I'm not the world's most masculine man / But I know what I am / And I'm glad I'm a man / [[Music/TheKinks 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.
-->''I grabbed her hair\\
Came off in my hand\\
And that beautiful girl\\
Was just a beautiful man.''
** Used in this case to [[DepravedHomosexual show how depraved the homosexuals are]] [[ValuesDissonance in the singer's eyes]], and both preceded and followed by gay bashing, since one of the other patrons in the bar did [[DisproportionateRetribution flirt with him.]]
* The Filipino song "Chiksilog" [[note]] a portmanteu of [=CHIcK=] (in the girl sense), [=SInangag=] (Fried rice) and [=ItLOG=] (egg, specifically a sunny sideup); [Viand Name]silog is a popular meal in the country. Culturally translated, it effectively means "A Chick with [[DoubleEntendre eggs".]][[/note]] by Music/{{Kamikazee}} is about a ''VideoGame/RagnarokOnline'' player's reaction to finding out the hard way that the "girl" his character hangs out with a lot turns out to be a CrossPlayer.
* ''The Doug Anthony All Stars'' song Sailor's Arms also has this theme.
* Music/PetShopBoys' "One thing leads to another". The protagonist [[DrowningMySorrows 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 Music/{{Aerosmith}}'s '80s comeback singles was "Dude Looks Like A Lady," with a line that goes, "Love put me wise/To her love in disguise/She had the body of a Venus/Lord, imagine my surprise!"
* Happened near the end of "Nobody Move" by Eazy-E
* [[http://www.youtube.com/watch?v=TzjMPPyze7I Ritsu Namine]] is a boy
* [[http://blogcritics.org/music/article/the-duke-listens-to-once-more/ This]] review of Music/{{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... [[http://www.youtube.com/watch?v=wMGpcjzb67Q 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).
** [[http://i48.photobucket.com/albums/f231/phwi/J-Rockers/Antique%20Cafe/AC_bou.jpg Bou]] from An Cafe as well.
** Just. [[http://www.angelicvoice.fr/style/visual-mana01.jpg Mana.]]
** This is taken to its logical extreme by Piko, who has a known reputation as a "Ryouseirui" - aka, a trap singer. [[http://www.youtube.com/watch?v=PIo7ifkyuiY It's not hard to see why]].
* Music/LeetStreetBoys song: [[http://www.youtube.com/watch?v=t8WGCUHkucY "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, [[{{Fetish}} 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.
* Tone Loc's "Funky Cold Medina": "But when she got undressed it was a big ol' mess... Sheena was a MAN!"
* EPMD's "Jane 3" off of ''Business As Usual'': It all starts when Erick & Parrish befriend a hard gangsta named Jay... but when they visit "his" pad, the decor (and bathroom contents) don't seem right...
* Schoolly D's "Saturday Night": "What I thought was a girl was nothin' but a fag" (Needless to say he's not gonna win any GLAAD awards either)
* From Music/{{Eminem}}'s Just Lose It:
--> '''Eminem''': Now what's your name, girl? What's your sign?
--> '''"Girl"''': Man, you must be up out your mind. *is actually Dr. Dre*
* Stolen City's video for [[https://www.youtube.com/watch?v=ksYre7Av4OE "Faces"]] features a man chatting up a girl in a bar. When his friends reveal the girl is transgender, he is ''[[{{Understatement}} not]]'' happy.

[[folder:Print Media]]
* Occurred on a huge scale in an issue of ''Magazine/MaximumPC'' 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 ToplessnessFromTheBack, but a very effeminate male.

[[folder:Pro Wrestling]]
* Wrestling/{{WWE}} wrestler Wrestling/MarkHenry ran into this trope years ago when he found out that a lady named Sammy which he fancied really had a dick.
-->"Oh sweet Jesus she has a penis!"

[[folder:Tabletop Games]]
* The ''TabletopGame/{{Eberron}}'' setting of ''TabletopGame/DungeonsAndDragons'' actually notes that this possibility of this occurring is one of the main reasons for the FantasticRacism 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.
** Nevermind that picture from the Sharn sourcebook that showed a couple of the working girls in the red-light district. The jokes that picture alone spawned...
* While technically androgynous in the new fluff, Daemonettes from ''TabletopGame/{{Warhammer 40000}}'' will play this trope on one of their victims just to watch them squirm. Because, you know, that's what they do. (And then they gut their victims like pigs with their claws, which can go through PoweredArmor like a knife through butter.)

* The play (and subsequent film) ''Theatre/MButterfly'' is about a French diplomat who has an affair with a Chinese opera singer, unaware that she is a) [[FemmeFataleSpy a spy for the Chinese government]] and b) a man in disguise. This is, believe it or not, a case of TruthInTelevision: the play is partially based on the life of [[http://en.wikipedia.org/wiki/Bernard_Boursicot Bernard Boursicot]].
--> "There are no women in the Chinese Opera."
* This one's OlderThanSteam because [[JustForFun/TheZerothLawOfTropeExamples Shakespeare did it first.]] Someone falls for the SweetPollyOliver in both ''Twelfth Night'' and ''As You Like It''. In ''Theatre/TheMerryWivesOfWindsor,'' Master and Mistress Page arrange for the suitors they prefer for their daughter Anne to elope with her (because they both like different ones), but Anne runs off with the man she actually loves and the two rejected suitors end up with cross-dressed boys. (Although it's not uncommon for at least one of them to be played as fairly happy with that, since they're both pretty camp.)
* This is the plot twist in ''Epicene, or the Silent Woman'', by Shakespeare's contemporary Ben Jonson, in which the protagonist persuades his eccentric, noise-hating uncle Morose to marry the title character as part of a plot to secure his inheritance: since he stands to lose it if his uncle marries, his plan is to provide him with a wife he doesn't like and then offer Morose a reason to end the marriage on the condition he gets his inheritance. Which he does by revealing to both the characters and the audience that Epicene has been a boy in disguise all along -- which would have been a big surprise to an audience accustomed to seeing female characters played by boys.
* Inverted in ''Theatre/AVeryPotterSequel'': Dumbledore assumes that Umbridge is actually a man in drag ([[CrossCastRole as she is played by one]]) and becomes attracted to her, [[spoiler: only to find out that she's actually an extremely butch woman]].

[[folder:Video Games]]
* Bridget, the WholesomeCrossdresser teenage boy in a nun habit from the ''VideoGame/GuiltyGear'' series, and former {{Trope Namer|s}}. 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 [[DownplayedTrope 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}} nun outfit.
** Even Zappa from ''VideoGame/GuiltyGear 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 [[http://danbooru.donmai.us/post/show/19660/4koma-axl_low-bridget-comedy-comic-crotch_grab-gui 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 OneHitKill attacks from the games.
*** Speaking of ''VideoGame/BlazBlue'', if you pit Bang Shishigami against Noel Vermillion in ''[[VideoGame/BlazBlueContinuumShift Continuum Shift]]'', he mistakes her for "a young man" despite her rather girlish clothing including a DangerouslyShortSkirt. Noel will believe it's because of [[ACupAngst her lack of boobage]] and [[BerserkButton GET PISSED OFF.]]
*** Amane Nishiki makes that mistake in Arcade Mode, too. He comments how Noel would be perfect playing the roles of women (never mind Noel is a girl) with the kind of crossdressing she's wearing at the time.
--->'''Noel''': [[foldercontrol]]

[[folder: [[Robo Speak Target deemed hostile. Commencing termination. ]]
*** Also speaking of ''VideoGame/BlazBlue'', [[ChivalrousPervert Kagura Mutsuki]] has a match intro where he scans the female anatomy, complete with targeting reticules and readouts. He does this with [[DudeLooksLikeALady Amane Nishiki]] as well, and expresses disappointment at the obvious. For FridgeBrilliance, Kagura's exact quote is "Not another dude...", which means he's already experienced this trope ''a lot'' and Amane wasn't his first case.
** Over here in RealLife, 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 (s/he and other characters of this trope are called "traps" for this reason). [[MemeticMutation As the meme says]], "Everyone is gay for Bridget".
* ''VideoGame/LeisureSuitLarry'' has this happen in both the sixth game ("Shape Up or Slip Out!") and the eighth game ("Magna Cum Laude"). The former involves a plot-critical sexual encounter with a very well-endowed transvestite (according to the documentaiotn/design notes) named [[spoiler: Shablee]], whilst in the latter, an optional character to pursue, [[spoiler: Koko the shy mime]], is actually a crossdressing boy.
* And for the most famous female example, you have Sheik of ''VideoGame/TheLegendOfZeldaOcarinaOfTime''. 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 War}}s over it.
* ''Franchise/{{Disgaea}}''
** This happens to Tink in ''VideoGame/{{Disgaea 2|CursedMemories}}'' when he tries to hit on a CuteMonsterGirl after joining your group. Of course, nobody bothered to tell him that the aforementioned "girl" is, in fact, Bridget's LawyerFriendlyCameo...
** Also happens in ''VideoGame/PrinnyCanIReallyBeTheHero''. The cute little [[HornyDevil Incubus]] is revealed in the hidden [[AllThereInTheManual Monsterpedia]] section that "she's" a he.
** The Alraune trap is brought back again in ''VideoGame/{{Disgaea 4|A Promise Unforgotten}}'' when the CuteMonsterGirl 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 ''VideoGame/DragonAgeOrigins'', it turns out that [[spoiler:Shale was actually once a female dwarf]]. Thanks to TheFogOfAges, even the character in question is stunned by this, making it a rare case of the ''character in question'' experiencing the unsettling reveal.
** It's implied that she was aware of the fact beforehand, just considered it, for all intend and purposes, unimportant, since she is, after all, a genderless golem.
* In ''VideoGame/MetalGearSolid2SonsOfLiberty'', 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?!''
** [[http://i31.photobucket.com/albums/c365/peachifruit/hiimdaisy/mgs/mgs2comic14.jpg This comic]] offers another perspective.
** According to an in-character Creator/QuintonFlynn, "Why would I even care? I'm not even [[BarbieDollAnatomy anatomically correct]]! I run around naked and I got no junk!" ...That might say something...
* ''Franchise/FireEmblem'':
** ''VideoGame/FireEmblemElibe'':
*** 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.
** ''VideoGame/FireEmblemAwakening'':
*** Averted with Lucius's {{expy}} [[DudeLooksLikeALady Libra]]. He mentions after being called a sister by Chrom that he's actually a priest. When he apologizes, he mentions that it could have been [[LampshadeHanging awkward]]. Very awkward. [[CrowningMomentOfFunny Very Very awkward]]. Unsurprisingly, Chrom tells him to stop. ("[[DeadpanSnarker God give me strength.]] ''Even the Queen's brother confused me for a woman''.")
*** Things indeed become funny and awkward in Libra's supports with [[ChivalrousPervert Virion]], who [[IfItsYouitsOkay continues to flatter his beauty]] even ''after'' finding out he's a man.
*** And he's also mistaken as a woman ''by at least one potential girlfriend/wife''. See his C support with Sully... who, [[MasculineGirlFeminineBoy ironically]], is one of ''the'' {{tomboy}}s of the cast.
*** And in Libra's solo ending, it's explicitly said that he both [[spoiler: built an OrphanageOfLove]] [[EvenTheguysWantHim and was asked out by both guys and girls]].
*** [[spoiler:It might be a trap for players to trap players who are [[OverlyLongGag expecting a "trap"]], but there is a masked young man who claims to be Marth and backs it up by wielding Marth's legendary sword, the Falchion. People are already very aware of Marth's gender at this point, right...? Turns out, this "Marth" is an imposter... [[{{Bifauxnen}} and a girl]]. Yeah. [[SamusIsAGirl Marth is A Girl]], [[http://fireemblem.wikia.com/wiki/Lucina and a very beautiful one too.]]) (You may now squee)]]. In fact, according to the promotional manga, [[spoiler: in-story this took place sooner than we thought]]... [[spoiler: Remember that Lon'qu was defeated by "Marth"? One of the reasons is that, during their fight, [[MasterSwordsman Lon'qu]] [[AccidentalPervert accidentally]] [[ThanksForTheMammary bumped head-first into Marth's chest]] and realised that his opponent was a woman. Since Lon'qu has a ''bad'' case of [[CannotTalkToWomen gynophobia]] due to his DarkAndTroubledPast, [[CurbstompBattle well]]...]]
* Flea from ''VideoGame/ChronoTrigger'' 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 MiniBoss. It's possible that Flea could, however, be FTM or the result of a magical experiment that stuck him in a female body/gave him breasts.
* ''VideoGame/FinalFantasyIV'' has a certain dancer in the town of [[spoiler:Fabul]].
* ''VideoGame/FinalFantasyV''. [[spoiler:The leader of a band of pirates called Faris is assumed to be a male due to occupation, but once the party gets halfway through the second dungeon it turns out he is a she. To quote a boss later on in the game, ''And now we shall fight like men. And women. And women who dress like men.'' She even occasionally mistaken refers to herself as male.]] 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 [[{{Bokukko}} stops]] some [[OreOnna people]].)
* ''VideoGame/FinalFantasyVII'': 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 [[http://i2.photobucket.com/albums/y4/madamhydra/FF7AC/female-cloud.jpg THIS]]. [[StupidSexyFlanders Stupid Sexy Cloud]].
* The ''Franchise/{{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 ''[[Anime/DigimonTamers Tamers]]''). Let's ignore the UnfortunateImplications of a male Sakuyamon. [[ShesAManInJapan The German fans must've been laughing hard at that one.]]
* Iita in ''VideoGame/BlazeUnion''. Oh, ye gods, Iita. She's a perfectly adorable little FilleFatale, cute and squeaky and very girly. Then night falls, and the other half of her SplitPersonality takes over -- the side that is male, brash, HotBlooded, 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 {{Fanservice}}-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 ''VideoGame/{{Atelier Annie|Alchemists of Sera Island}}'' 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 ''VideoGame/ForumWarz'' 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=].)
* [[spoiler:Erica]] from ''VideoGame/{{Catherine}}'' is actually a trans woman. 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.
* ''VideoGame/DarkSouls'' 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. ''[[UpToEleven He even has tits.]]''
* ''Franchise/{{Pokemon}}'':
** One of the Ferris Wheel date options for the male player character in the Japanese version of ''VideoGame/PokemonBlack2AndWhite2'' is a schoolteacher who, mid-ride, takes off his shirt in the heat and [[WholesomeCrossdresser admits he had to pose as a woman to get the job]]. This is censored in most translations.
** [[spoiler:Gothorita]] mentions in ''[[PokeParkWii PokePark 2: Wonders Beyond]]'' that many Pokemon mistake him for a girl.
* ''[[Franchise/ShinMegamiTenseiPersona Persona]]'':
** In ''VideoGame/Persona4'', exactly how Unsettling [[spoiler: Naoto]]'s Gender Reveal is to Kanji is a vital piece of the latter's characterization. Kanji, who can be interpreted as [[AmbiguouslyGay struggling with very deep sexual identity issues]], textually expresses almost the exact same mixture of anxiety and eagerness in interactions with [[spoiler: Naoto]] before and after the scene in question. Perhaps most tellingly, though, Kanji is at his most resolute when [[spoiler: Naoto]]'s life is in imminent danger of [[ShadowArchetype Shadow]]-fueled destruction, only moments after the Reveal itself.
** ''VideoGame/Persona3'' has the more basic PlayedForLaughs version of the trope during "[[MundaneMadeAwesome Operation Babe Hunt.]]"
* [[spoiler:The thief]] in ''VideoGame/RatchetAndClankGoingCommando'' is revealed to be a girl, upon which Ratchet comments "Whoah! He's... a she!"
** Happens to Clank in ''[[VideoGame/RatchetAndClankUpYourArsenal Up Your Arsenal]]'', in which the duo find a video of Qwark DisguisedInDrag. Clank's first thought is "What? That Qwark had a sister?"
* The Japanese ''VideoGame/AnimalCrossing'' has this according to [[ShesAManInJapan Blanca's]] bio. It translates to: "When I suddenly met her she asked me to please paint her face, it really surprised me! Did her makeup fall off maybe? Huh? Sheís a boy?!"
* ''Videogame/NieR'' has an unusual version of this in that one of the main characters, Kainé, is revealed to be a hermaphrodite. This is done very subtly in-game, so a lot of people might have ended up not realizing it if that piece of information hadn't been leaked somehow before the game even came out.
* [[MysteriousWaif Elh]] from ''VideoGame/{{Solatorobo}}'' talks and acts like a boy, but is revealed to be a girl when [[ShowerOfAwkward Red walks in on her bath.]]

[[folder:Visual Novels]]
* In ''VisualNovel/DanganRonpa'', this trope happens with [[spoiler:Chihiro. Since this happens after he is murdered, it becomes even more unsettling]].
* In ''VisualNovel/FateStayNight'', there's a reason why Guinevere had that affair with Lancelot, since her husband, KingArthur, aka Saber, [[SweetPollyOliver turns out to be a woman]] (and stopped aging at the age of 15), but Guinevere agreed to the marriage as [[SexlessMarriage political fiction only]], and due to that reason Arthuria never blamed Guinevere nor Lancelot for their romance and was forced to take action against it by her enemies.
** This also occurs in the {{prequel}} series ''LightNovel/FateZero'', 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, Kiritsugu's wife Irisviel explains to her that it's more than he's saddened because he realizes what [[TheWoobie Saber]] was forced to go through, including hiding her identity.
** The Japanese version of ''VideoGame/FateExtra'' subverts this trope by implying "Sir Francis Drake" is [[SweetPollyOliver actually Queen Elizabeth in disguise]].
** However, in ''VideoGame/FateGrandOrder'', male heroes turning out to have been women in disguise all along is an UnusuallyUninterestingSight to the protagonist.
* Shika in ''VisualNovel/KiraKira'', 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, [[IfItsYouItsOkay but quickly got over it]] even offering to ''be his wife'' since the idea seemed to make him uncomfortable.
* [[spoiler: Robin Newman]] in ''VisualNovel/PhoenixWrightAceAttorneyDualDestinies''. It catches EVERYONE in court off guard, [[UpToEleven including]] ''[[TheStoic Blackquill]]''.
* ''VisualNovel/SteinsGate'':
** Invoked and parodied by the narration when Ruka is introduced. Without prior knowledge of the character, you ''will'' assume they're a girl (the {{Miko}} outfit doesn't help), but Rintaro will eventually start making complementary remarks in narration "More feminine than any woman alive..." only to end them with "...But, he's a guy!".
** Kurisu also appears quite disturbed the first time Rintaro corrects her when she talks about how nice Mayuri's 'female' friend was.
** In-universe example for Rintaro after [[spoiler:Ruka manages to change her sex to female (at birth) using D-Mail. The fact that she looks exactly the same either way doesn't help matters. Arguably, it's just as unsettling for Ruka herself, as Rintaro tries to grab 'his' area to prove 'his' gender]].
** Much later, Ruka receives one of these for [[spoiler:herself, when she comes to remember parts of another world line where she was a he]].

[[folder:Web Animation]]
* This joke was done as a gag during a scene where Hal is trying hit on women in episode 6 of ''WebAnimation/BowsersKingdom''.
* A RunningGag in ''Machinima/GamerPoop'' which takes place at LEAST once an episode.
* Parodied (along with many other anime tropes) [[http://www.youtube.com/watch?v=r8UicVSqXi4 here.]]
* Unsettling in-universe for Carl from ''WebAnimation/LlamasWithHats'' to learn that his roommate, who had been unidentified prior to that point, was a male named Paul (in Carl's defense, Paul's hat is rather feminine, but he couldn't even remember Paul's name after three years). After asking Paul if he's sure, which Paul confirms to his annoyance, [[spoiler: Carl then says he has to go delete some pictures from his computer]].

[[folder:Web Comics]]
* In ''Webcomic/ElGoonishShive'', 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.
* ''Webcomic/TheWotch'' manages to do this to ''both'' participants, [[http://www.thewotch.com/index.php?epDate=2003-09-10 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 ''Webcomic/WelcomeToTheConvenienceStore''.
* ''Webcomic/GhastlysGhastlyComic'':
** A rather ridiculous case when the two similar-looking characters in the rather ambiguous fighting game (within a webcomic) "''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 RunningGag 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.
* ''Webcomic/TheOrderOfTheStick'':
** Averted very carefully by Vaarsuvius, an elf whose gender remains unspecified (and just to keep the readers guessing, the gender of [[spoiler:V's lawfully wedded spouse]] is also unspecified and [[spoiler:their kids are adopted.]])
** Invoked when Belkar hits on a [[GenderBender magically gender-swapped]] Roy. Turns out, he knew it was Roy the whole time, and he was just doing it to squick him out.
* ''Webcomic/{{Concession}}'': Artie wakes up to discover he has [[spoiler:engaged in inappropriate acts with hypersexual preteen Chelsie Warner while in a brain-tumour-induced -- or, as it turned out, Joel-induced --]] trance, and confides in his boss:
-->'''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.'''
** This [[http://concessioncomic.com/index.php?pid=20090327 later]] happens during an occasion where Joel, Matt, and Aaron "Nicole" O'Connor meet with a crude ursine associate of Matt's who initially believes Nicole is a girl after Joel introduces them. Needless to say, said ursine friend is [[http://concessioncomic.com/index.php?pid=20090331 moving to kick Joel's ass]] when he finds out the truth of Nicole's gender.
* [[http://www.somethingpositive.net/sp10272004.shtml This]] strip of ''Webcomic/SomethingPositive''.
* In [[http://www.sluggy.com/daily.php?date=971007 this]] strip of ''Webcomic/SluggyFreelance'', 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.
-->'''Torg:''' Aw, you think what you want.\\
'''Riff:''' Can you jump up and down for us, mister?
* ''Webcomic/DanAndMabsFurryAdventures'':
** 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. (In an omake, the doctor delivering Mink at hir birth [[TheUnReveal never gets to say]].)
* ''Webcomic/VenusEnvy'' has this happen to Lisa when she assumes that Chris is a {{transgender}} woman only to discover that he's actually just a WholesomeCrossdresser. 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.
* ''Webcomic/MaterialGirl'', in which the character the title refers to is a trans girl.
* [[http://doublek.thewebcomic.com/comics/1358248/chapter-1-03/ This page]], from ''Webcomic/DoubleK''.
* Used in ''Webcomic/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 ''WebComic/TehGladiators'', 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 [[http://headtripcomics.comicgenesis.com/d/20060330.html this strip]] of ''Webcomic/HeadTrip''.
* ''Webcomic/JetDream:''
** Averted by the [[WholesomeCrossdresser Elle-Boys]] of J.E.T. T.E.E.N. Despite looking exactly like girls, they make no secret of the fact that they're actually boys. As a rule, they're also [[HaveIMentionedIAmHeterosexualToday heterosexuals]] who exhibit many "traditionally masculine" traits.
** In the story "South Pacific Powder-Puff Power!"[[note]]''Jet Dream and her T-Girl Counterspies'' #3[[/note]], there's a startling revelation about a longstanding character. [[spoiler:The T-Girls learned that Ting, the Polynesian princess and only "female" member of the Thunderbirds, had actually always been a male. In Ting's matriarchal tribe, male royals are expected to live as women. When the rest of the team changed sex, so did Ting.]]
* Reversed in ''Webcomic/KevinAndKell''. Rachel, upon first meeting Bruno (a herbivorous wolf), tries to romance him because she thought he was a sheep. To be more specific, ''not a male sheep''. You see, 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's wool. The end result was Bruno added ram horns to the sheepskin so he's never mistaken for a girl again.
* Done in [[http://www.duelinganalogs.com/comic/2010/08/05/package-deal/ this]] strip of ''Webcomic/DuelingAnalogs'', where one man mistakes a Bridget cosplayer for [[Manga/ChronoCrusade Rosette Christopher]].
* [[Manga/{{Hellsing}} Alucard]] pulls this off as Girlycard in ''Webcomic/AndShineHeavenNow''. Granted, the person he fooled is [[Literature/JeevesAndWooster Bertie Wooster...]] And then many years later did it to [[Anime/RODTheTV Maggie Mui...]]
* From ''Reversed'', after a long overdue reveal: [[http://www.seigane.net/reversed/index.php?&s=a&p=0528 "What is this, Effin Trapsville?"]]
* Happens to Pintsize in ''Webcomic/QuestionableContent'' when he learns that the [=AnthroPC=] with whom he's been chatting is actually a male [=AnthroPC=] [[http://questionablecontent.net/view.php?comic=339 whose online icon happens to be pink]].
* Doubled up in the now defunct comic ''Roomies'' with Corey and Dave(ina), they were both posing as men so their boss and co-workers in IT would take them seriously when they went on a date and revealed to one another that they were actually women. They started sleeping together anyways.
* ''Webcomic/SexyLosers'' 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 [[spoiler:she is a woman, but he's gay and he thought he was hitting on a man to begin with]].
** [[spoiler:Would that be a booby trap?]]
** 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. [[spoiler:So the guy jumps before the cross-dresser does]].
*** This was later revealed to be [[IncrediblyLamePun jumping to conclusions]] in a [[http://sexylosers.com/g081.html guest comic that]] [[spoiler: both of her parents are crossdressers who are angry that their daughter isn't.]]
** And a final one has a [[TheChikan subway groper]] realize this. [[spoiler: [[ItMakesSenseInContext It ends up with the "and that's how you were born"]] RunningGag.]]
* The [[TheReveal big reveal]] in chapter one of ''Webcomic/LavenderLegend'' is that Felicia, the tall and dour maid in the employ of Princess Lavender (and also LaResistance), is actually male, but was raised as a female by [[WordOfGod his]] mother in order to keep him from [[DraftDodging being conscripted]] into the kingdom's ruinous war that also killed his father. [[SingleTargetSexuality That doesn't stop Princess Lavender from enjoying their earlier first kiss]]... [[AllWomenAreLustful or from constantly tempting Felicia with sleeping in her bed.]]
* One ''Webcomic/ManlyGuysDoingManlyThings'' comic has Jared unsettled and warning Commander Badass that [[VideoGame/FinalFight Poison]] was, in his words 'a dude'. Commander Badass then points out that it shouldn't matter what a person has in their pants unless you're planning to get into them. He's more surprised that Jared thought he had a chance to score with Poison, gender aside.
* In the "Railway Children" arc of ''Webcomic/SkinHorse'', Violet Bee tries to invoke this trope by revealing his gender to Tip. This plan falls flat because A) Tip was never particularly attracted to Violet and B) Tip is an ExtremeOmnisexual.
* It was apparently a common occurrence for the flat-chested namesake of ''Shayla The Pink Mouse'' to be unknowingly picked up by gay men who thought she was a man until they got her to bed.
* ''Webcomic/ScandinaviaAndTheWorld'':
** Averted. Denmark asks Thailand if he could buy 'the sexy lady' a cocktail, but Thailand admits he's ''Brother'' Thailand, not Sister Thailand. Denmark thinks about it for a {{Beat}}, then [[http://satwcomic.com/no-surprise asks if he'd rather have a beer]].
--> [[WordOfGod Denmark doesn't care what you are. Only thing that matters is if you want to have sex with him or not.]]
** And in another [[http://satwcomic.com/confusion strip]] we have Sister France hitting on Sister Denmark (she thought that it's a handsome long-haired guy). And when they get to the action...
-->'''Sister France:''' Where did those breasts come from?! And where is the penis?!\\
'''Sister Denmark:''' ...I don't know.\\
'''Sister France:''' I WANTED PENIS!!!
* A blatantly explicit one is seen in ''Moon Over June'' when Hatsuki (a highly promiscuous lesbian) barely makes it to the parking lot before she had that evenings hookup's head between her legs. When she went to return the favor....
-->"You picked me up in a transvestite bar! I thought you knew!\\
"I just ''had'' to go someplace new didn't I?"
* In ''WebComic/DarthsAndDroids'', this trope is used wonderfully with TheReveal. [[spoiler:In this universe, Darth Vader is actually Padme Amidala, not Anakin Skywalker. When this bombshell was dropped during the [=RPing=] of ''Film/TheEmpireStrikesBack'', it totally waylays the entire team, who demand how this was possible.]]
* Discussed in [[http://www.molebashed.com/post/136860753713/virtual-reality this MOLEBASHED comic]]. Wes talks to his wife about reading a book in which characters live their lives in virtual reality. (The book is unnamed in the strip, but in the accompanying post, he confirms that he's talking about Literature/ReadyPlayerOne.)
-->'''Wes:''' What if '''we''' are the computer-game-avatars for people in the "real world?" What if, in reality, I'm a seventy-year-old cat hoarder who smokes two packs a day?
-->'''Kari:''' What if I'm a dude?
-->'''Wes: [[BigNo NOOO!]]'''


[[folder:Web Original]]
* A common prank that people pull on the internet is to post a picture of a hot girl for everyone to ogle, only to reveal that the hot girl is really a very feminine man. Some goons at Website/SomethingAwful 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.
* All the hot women on the Internet that are actually [[{{GIRL}} guys posing as women online.]]
* Many [[http://www.youtube.com/watch?v=HAs7IFvnhZA online]] [[http://www.youtube.com/watch?v=aZ8oTyG0ey8&feature=channel_video_title webcam]] pranks invoke this trope.
* [[http://www.fmylife.com/love/245607?utm_source=fmylife&utm_medium=illustrated&utm_campaign=245607 This]] illustrated FML.
* The title WholesomeCrossdresser in ''Literature/TheSagaOfTuck'' does this both when crossdressed and in his normal, baggy boy clothes. The latter tends to annoy him.
* ''WebVideo/{{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 adoptable petsite VideoGame/{{Valenth}}, one of the [=NPCs=] is the person of intelligible gender of the week, [[http://valenth.com/lore/Elliot Elliot Christoph]]. Considering many of the humanoid [=NPCs=] are like this, and all of them as such are 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 is referred to as being female about twenty pages into the thread. The real kicker was the fact that she never bothered correcting them once. [[DudeLooksLikeALady Lady looks like a dude]] indeed.
* ''Website/DesuDesBrigade'': Professor Otaku admits in his Quick Hits review of ''{{Manga/Gravitation}}'' that he didn't realize [[{{Uke}} Shuichi]] was male until he was halfway through an internet porn search of "her".
-->'''Prof. Otaku:''' Well... wow, she really likes it in the butt. Hmm... Why does she... ''Oh.''
* WebVideo/TheNostalgiaChick uses the Austin Powers "She's a man!" joke to express her doubts about Mel C being a real woman.
* In the WebVideo/TheCinemaSnob review of ''Sadomania'', he repeatedly remarks how beautiful the female warden is and checks the back of the box to find out her name...and discovers she is played by "the stunning transsexual adult film star Ajita Wilson". Cue a horrified "Oh my God" followed by a SmashCut of him sitting in the shower fully clothed calling Jillian on the phone claiming that they have to have sex "right NOW" since he's "so confused". According to the video description, this was based on a friend of Brad's having had the same revelation.
* In the ''WebVideo/KeyOfAwesome'' parody of Music/CarlyRaeJepsen's "Call Me Maybe," Carly meets a cute guy at the club. The two of them get drunk, then go to Carly's house and make out. The next morning, the guy wakes to find that Carly is actually a madman dressed as a young woman.
* Fairly common in the ''Literature/ChakonaSpace'' setting considering how many characters are {{Hermaphrodite}}s. Perhaps the most notable example being when Garrek and Chakat Goldfur first started seeing each other and he spotted hir male parts and freaked. Though Garrek later apologized, saying he should have looked up Chakats on the net and realized that they were herms, and they got back together, so far they've got two cubs by one another.
* In ''WebVideo/VaguelyRecallingJoJo'', Nena isn't a fat woman wearing the skin of another woman. Instead, Nena is a boy pretending to be a girl. Polnareff is shocked when he finds out.
* Zigzagged in the [[Literature/DeadWest Dead West Porcelain Doctor]]; the narrator, a journalist named Gervas meets the titular porcelain doctor on a steamship, and concludes that the waifish, slim redhead with the creamy skin and the narrow waist ("like wearing a corset") and soft voice, wearing dainty glasses must be a crossdressing woman. He swores to protect the doctor, who is quite baffled, but accepts... then later, on a train, after a clash with [[OurZombiesAreDifferent "shamblers"]], the doctor disrobes a bit. Our narrator promptly tries to look away, but peeks a little, and takes a DoubleTake. The doctor was, in fact, a he. Not that this stops Gervas. Even better, almost everybody mistakes him for a girl. Carolina even grabbed his loins (cue minor freakout, from both parties), and wasn't too sure even after that!
* ''[[Website/NotAlwaysRight Not Always Learning]]'' has the story [[http://notalwayslearning.com/new-meaning-to-gender-displacement/33589 "New Meaning to Gender Displacement"]], where the submitter does this to a group of girls at her school ("OH, MY GOD! HE'S A GIRL!"). [[http://notalwaysfriendly.com/new-meaning-to-gender-displacement-part-2/35950 The sequel]] on ''Not Always Friendly'' has the same person do so again, in a different way; bonus points for the target being with her boyfriend, who started laughing hysterically in the aftermath.
* Discussed in an episode of ''WebVideo/NeedsMoreGay'', where Rantasmo points out how ''hugely problematic'' it is that the vast majority of trans representation in media (which isn't very large to begin with), falls under this trope. Especially when the reaction of many male characters to discovering the girl they liked is actually trans is to throw up.
* Common for Phase in ''Literature/WhateleyUniverse'', as he is an [[{{Hermaphrodite}} intersexed]] mutant whose body is mostly female (and [[AttractiveBentGender extremely gorgeous]]) but who retains his original male gentalia, gender identity and sexual orientation. Unfortunately, more than a few males can't see past his appearance, and some (such as Imperious, who as the reincarnation of Zeus never gave much of a damn about the sex of his partners anyway) are actually ''more'' interested in him knowing that he's a 'she-male'.
** Averted with Mega-Girl and Stronghold. When Mega-Girl reveals that she's both {{Transgender}} and a GenderBender (but still mostly male for the time being because of the slow manner in which she is changing), Stronghold answered that he loved her anyway.
** [[ZigZaggedTrope Zig-zagged]] for Absinthe and Flytrap; Collin had been a bully to Adam, but they didn't know each other very well beyond that. When Gwen (formerly Adam) meets Collin again after she is [[ItMakesSenseInContext 'rescued' by the Mutant Supremacist cell who were trying to recruit Collin]], she let's Collin assume that she is Adam's sister. Later, on the trip out to Whateley, they hit it off as friends, and during the first month of school they quickly start feeling romantically towards each other - until Collin finds out that Gwen ''was'' Adam. Collin flips out, not because of the gender issue (well, not entirely) but because he thought she actually was just Adam using an illusion to trick and humiliate him. When she finally explains that she was a GenderBender due to her mutation, he stops being quite as angry, but still feels betrayed because she wasn't upfront about it. They do eventually get back together, though.
* Subverted at the end of the first episode of ''WebVideo/PopQuizHotshot'', as General Anesthetic reveals that he used to be a woman. Critic's surprised, but he ends up wanting to be invited to the General's BDSM parties.

[[folder:Western Animation]]
* ''WesternAnimation/SpongeBobSquarePants'': 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. (Take note that he [[NakedPeopleAreFunny strips himself butt-naked in the process]], resulting even more {{Squick}} to both suitors.)
-->'''Squidward:''' Um...I think I need to take a shower.
* In the surprisingly serious short ''WesternAnimation/WhatsOperaDoc'', Elmer Fudd finds out that the girl he fell for was WesternAnimation/BugsBunny in a dress -- and ''[[DownerEnding 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.
-->'''Bug:''' Well, what didja expect in an opera? A ''happy'' ending?
* ''WesternAnimation/FamilyGuy'':
** Pervert Glen Quagmire gets quite an unsettling revelation when he tells Peter and the gang that if he could have any woman in the world, he'd choose Taylor Hanson from the 1990s band Music/{{Hanson}}.
-->'''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!
** 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:
-->'''Brian:''' And you had sex with two Filipino women. ''(sniffs again)'' And a man.\\
'''Quagmire:''' You mean ''three'' Filipino women!\\
'''Brian:''' ''(DisapprovingLook)''\\
'''Quagmire:''' ...'''''[[BigNo Aaugh!]]'''''
** In a similar vein, Brian, on the way home from a convention, goes to a hotel bar, meets up with a woman (who the audience knows the identity of), 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 to find 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 is the man going through a sex change operation and how everyone around was dealing with it.
* ''WesternAnimation/TheClevelandShow'' 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 ''[[NoCelebritiesWereHarmed not]]'' Creator/TylerPerry / 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 abandoned her. And then when Cleveland DOES tell him, it's not heard, but you see the two men gesturing... then just like Brian Griffin in the above example, the dad [[VomitIndiscretionShot vomits for thirty seconds.]]
* ''WesternAnimation/{{Futurama}}'':
** There is the Valentine's Day episode in which [[GeneralFailure Zapp Brannigan]] is on a blind date with a very burly man in drag, who leaves unexpectedly early...
-->'''Zapp Brannigan:''' Honey! Wait! You didn't show me your surprise!
** Inverted in "War is the H-Word," when Zapp finds himself attracted to "Lee Lemon." He is quite relieved when he finds out it was Leela all along.
-->'''Zapp Brannigan:''' Leela! So it's you I've been attracted to! Oh, God, I've never been so happy to be beaten up by a woman.
-->'''Leela:''' Let's do it again sometime.
** 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) [[DoesThisRemindYouOfAnything cross-species dresser with a fetish for aliens]]. He feels shocked and violated.
** "In "Fry and the Slurm Factory" when Fry and Bender are messing around with the Professor's x-ray gun, Bender uses it on a fembot that catches his attention, but is horrified to learn she's a manbot ([[DoesThisRemindYouOfAnything who only has one more upgrade to go before becoming a fembot]]). The {{transgender}} robot bitches Bender out for leering at her and reacting in disgust.
* ''WesternAnimation/BatmanBeyond'' sees Ra's Al-Ghul transferring his mind into his daughter Talia's body... and Bruce Wayne has quite the history with her [[CelibateHero (Well, as much as he does with anyone)]]. What transpires thoroughly creeps both Bruce and Terry out.
-->"I did not mean for you to find out this way. But I suppose what's done is done...[[LarynxDissonance DETECTIVE!]]"
** And then later:
-->'''Terry:''' Lady, that is the ''sickest'' thing Iíve ever seen! Youíre creeping me out!
-->'''Bruce:''' You?! She ''kissed'' me!
** Note that this is ''Batman'' saying this, and considering his career (which he is more-or-less retired from at this point), it should say a lot.
* In the ''WesternAnimation/JohnnyBravo'' episode "As I Lay Hiccuping," Johnny goes to a very shapely female doctor to do something about his really bad case of the hiccups. When he returns to her for her "special treatment," the female doctor [[FullBodyDisguise pulls off her rubber woman suit]] to reveal a male, bald and heavy doctor with a beard. Johnny's shocked reaction cures his hiccups, and the doctor reveals this trick works every time.
* The ''WesternAnimation/TinyToonAdventures'' episode "Pluck O' The Irish" ends with a pretty lass revealing to Plucky and Hamton that she is actually three male leprechauns [[TotemPoleTrench stacked up]] with the top one [[LatexPerfection in a rubber girl mask]].
* In a later episode of ''WesternAnimation/KingOfTheHill'', Peggy befriends a drag queen, after discovering "she" has size 16 feet like her. The reveal is unsettling for both of them since Peggy thought Carolyn was a woman and Carolyn thought Peggy was a drag queen.
* Done in a two part episode of ''WesternAnimation/SouthPark'' when Cartman, who's stuck in the future (long story, basically one of his usual schemes backfired), calls back to the past to reach Mr. Garrison who's recently had a sex change operation. [[{{Squick}} Garrison is currently having sex with Richard Dawkins]], Dawkins is the one to answer the phone and Cartman lets slip that Garrison is a post-Op. Needless to say Dawkins is repulsed. Not only that but by revealing this, it ''completely changes the future''.
* In ''WesternAnimation/TheLegendOfKorra'', Bolin falls for both of Korra's cute twin cousins, Desna and Eska, before Korra reveals that they're actually {{Half Identical Twins}}--Desna is a guy.
* ''WesternAnimation/TheVentureBros''.
** Inverted. Dr. Girlfriend tried to seduce Brock a couple of times. Brock thinks Dr. Girlfriend is a {{Transgender}} woman because of [[CrossDressingVoices her masculine voice]] so it doesn't work. However the real reason she has a deep voice is due to her smoking habits.
** Inverted again. Doc never finds out [[ButchLesbian Ginny]] is a woman because he's not even remotely attracted to her.
* in ''WesternAnimation/TheSimpsons'' episode "Bart's Girlfriend", Bart hears angelic singing coming from the Springfield church, and assumes that it's Jessica Lovejoy. Turns out it's Ned Flanders.
-->'''Bart''': Ughhhh. That's very disturbing.
* Near the end of the ''WesternAnimation/DannyPhantom'' episode "One of a Kind", he discovers up close that the rare purple-back gorilla "Samson" is actually a "Delilah". This is his reaction.
* ''WesternAnimation/BeavisAndButtHead'' watch a Creator/RuPaul video:
-->'''Beavis''': Hey, Butt-head, that chick is pretty hot!
-->'''Butt-head''': Uhhh, ya think so?
-->'''Beavis''': Yeah, I'd do her in a minute!
-->'''Butt-head''': Huh huh, that's a ''guy'', Beavis! Huh, huh, you wanna make out with a guy!
-->'''Beavis''': SHUT UP, BUTT-HEAD!
* ''WesternAnimation/AtomicBetty'': At the end of the "No Business Like Snow Business" Betty gets on the boys' hockey team, unbeknownst to Penelope and her friends who swoon over "him" from the stands. Then Betty takes her helmet off. Penelope storms off angrily while her friends just laugh it off.
* In ''WesternAnimation/TheLooneyTunesShow'' apparently even ''Sylvester'' thought Tweety was a girl until Tweety himself told him.

[[folder:Real Life]]
* Taken to it's most unpleasant extreme by the red wolf fish, a predatory fish native to the Amazon. The wolf fish mimics the appearance of the female of another species of Amazonian fish. When an amorous male of that species comes seeking a prospective mate, he gets eaten.