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    Anime and Manga 
Miaka: (Accidentally rips Nuriko's upper dress and gets to see the chest area) N-nothing... YOU'RE A GUY!? (Super-Deformed rocket explodes on her)
Nuriko: (does a faux-Noblewoman's Laugh) Oh well, the cat's out of the bag... Yes, I'm a guy, what are you gonna do about it?
Miaka: You're a guy and you're in love with Hotohori!? And you even kissed Tamahome!
Nuriko: I've abandoned the path of manhood in the name of love!
Miaka: (My head hurts. I wonder if I'll ever get to Taiitsu-kun's home safely...)

Tsubomi: So cool... [Itsuki]'s so cool...!!
Erika: Oi... if you don't want to get into a big shock, maybe you should seek someone else other than the Student Council President...
Tsubomi: ... W-what!? What was that about?! (other students glare) S-sorry...
Erika: I'm telling you, the student council president is-
Tsubomi: You're disturbing his training. Could this be... first love?! Even if you say otherwise, my heart is burning!
Erika: Well, I dunno...
[...]
Servant: Itsuki-ojousama, here's your tea.
[...]
Tsubomi: "O-Ojou-sama?!"
Erika: The student council president is a girl. The entire school knows that. You were busy dozing off so you probably did not listen.
[...]
Tsubomi: The student council president is a girl... My first love... ended in three minutes... T_T

Desertrian Itsuki: These clothes are so cute! I love it!
Cobraja: Hey, uh... what are you saying?
Desertrian Itsuki: I... I... I'm a girl!!
Cobraja: *Beat* ... EEEEEHHHH!?!?!?
HeartCatch Pretty Cure!, same episode as the above.

Your sister has a palm tree and coconuts! Sausage... elephant... wiener! ***k o* destiny!

Ichika: I couldn't tell him my feelings after all. I'm so gloomy!
Akira: Ichika-san.
Ichika: W-W-W-What do you want?
Akira: Miku gladly accepted that chocolate.
Ichika: That's great.
Akira: She said the chocolate dog looks like me. Thank you so much!
Ichika: (fidgets and blushes) W-Well... Would you like to go out tog—
Genichirou: OH! You became friends right away!
Ichika: Dad.
Genichirou: Good for you. It's just like you have a sister.
Ichika: You say whatever you feel— A sister? You mean a brother, right?
Genichirou: What are you saying?
Ichika: Eh... (faces Akira, stunned) Eh?
Akira: (embarrassed laugh) Don't worry. I'm often mistaken.
Ichika: Y... you're... you're a womaaaaaaaaaaaaaaan?!

...Where are your boobs?!

(said after Tanukichi realizes his foot is pressed against Oboro's crotch)
Tanukichi: (thinking to himself) "...let's examine the situation."
(uses his foot to double-check, inadvertently causing Oboro's back to suddenly arch along with "her" foot)
Tanukichi: (sweatdrops) "That's a d*ck."
Shimoneta, chapter 10

Hisae: (holding out a Valentine's Day gift) I'm always, always watching you. You look so handsome when you're playing tennis. Um... please accept this.
Tennis Player: ...I'm a girl...
(Hisae falls to the ground in shock and bursts into tears)
Kodocha, Episode 45

Jeanne: Hey, what are you doing running around... naked...
Astolfo: (completely naked with towel on his back) Ruler, is something wrong? (zooms to near his crotch area) You're making a weird face.
Jeanne: ....... AAAAAAAIIIIIIEEEEEEEE!!!!!!

Kazuma: Sylvia, Sylvia, why do I feel like something is pressing my butt??
Sylvia: Because something is!!
Kazuma: (massive Oh, Crap! face) NNNNNNOOOOOOOO!!!!!!
Subtitle: (Kazuma was psychologically scarred)
KonoSuba - Legend of Crimson

Haku: Let us meet again one day. Oh, by the way... I'm a boy.
Naruto: !! (N-No way!! Even though you're cuter than Sakura!?)
Naruto

    Comic Books 
Fifty? Why'n't you show this mothafucka yo' dick?

    Fan Works 
Kyoko Kirigiri: Chihiro Fujisaki's corpse was moved into the girls' dressing room, but in reality the crime scene took place in the boys' dressing room. The reason for this... is because Fujisaki... isdesignatedmaleatbirthalthoughicannotsayeitherwaywhethertheyidentifyaseitheroranygenderbutnonethelesstheiridrecognizesthemasmale.
Everyone: (mass gasping)

Vegeta: Look at you, Dodoria. You're always so damn proud. And now here you are, crying like a woman!
Dodoria: I AM A WOMAN!
Vegeta: Wh...what?
Dodoria I SAID I AM A WOMAN!
(Beat)
Vegeta: WHAT?!
[...]
Dodoria: ...And that's why I was considered the most beautiful, and fertile, woman on my home planet. Before Freeza blew it up.
Vegeta: He tends to do that. Also, huuuurrrgh.
Dragon Ball Z Abridged episode 15

I told you before... I am not a woman! I'm a man!

Polnareff: Hey Mr. Joestaaaar! Hohahoi! Oh boy, man oh man. I was totally tricked. [Nena] turned out to be a boy.
Joseph: Hahaha, that's too bad! Can't expect things to be easy in the world we live in. Especially for someone like you.
Polnareff: What the hell does that mean?!

Joey: Yug, why do you hate women so much?
Yami: Why wouldn't I hate women? I mean, they hate me.
Joey: What?
Yami: Yeah, that Marik chick is always saying how much she despises me.
Joey: Er, Yug, I don't know how to tell you this, but Marik's a guy.
Yami: What?! That's crazy!
Joey: I know.
Yami: But look at the way she dresses!
Joey: Totally a guy.
Yami: That's crazy ... What about Bakura, is she-?
Joey: Bakura's a guy.
Yami: That's crazy! And what about Tea, guy or girl?
Joey: She's a girl.
Yami: Oh ... that's crazy! Anyway, I should probably finish this duel ... but that's crazy!
Joey: Yeah.

    Film - Animated 
Francis: So, being a ladybug automatically makes me a girl! Is that it, flyboy?!
Fly 1: Yikes!
Fly 2: She's a guy!

Gasket: Who are these losers?
Fender: We, Sir—
Gasket: (deadpan) I'm a woman.
Crank: Ouch.

    Film - Live-Action 
What the... That's it. That's it. Einhorn is Finkle. Finkle is Einhorn! EINHORN IS A MAN! (remembers that he kissed Einhorn) OH MY GOD!! EINHORN IS A MAN?!

Oh, my name is Tim. I'm always available. By the way, I also do engine work on BMW's.
Transvestite Hooker, Bachelor Party

You're in Bangkok, honey. There's a reason they don't call it "Bangcunt".
Kimmy, The Hangover

Is this a magic show?
Zach (upon seeing Kimmy has a penis), The Hangover

I had sex with a man with boobies!
Stu (upon his drug-fueled encounter with a transvestite hooker), The Hangover

Donald: Whenever you're ready, dude.
Cynthia-Rose: (sighs in annoyance, taking off her cap and revealing her pink hair)
Donald: Oh. Not a dude...

Angela. Such a lovely name. Why I believe it means "angel!" Why, yes, I'm sure it does! I know you're going to like that name, won't you, Peter?

Oh my God! She's a boy!
Bobby, Sleepaway Camp

Jerry: I'm a man!
Osgood: Well, nobody's perfect.
Some Like It Hot, final lines of dialogue

(Fergus undresses Dil, only to discover she has a penis) You didn't know, did you? Oh my God.
Dil to Fergus, The Crying Game

That blonde chick's a dude? Oh man!
Male Fan, (about Jimmy McElroy), Blades of Glory

Ned the Cameraman: You were a dude this whole time?
Dr. Jonathan Jacobo: Of course, dummkopf.
Ned the Cameraman: But we cuddled!

    Live-Action TV 

    Music 
So I took her to my crib, and everything went well as planned
But when she got undressed, it was a big old mess, Sheena was a man
Tone Lōc, "Funky Cold Medina"

Bitch was frontin' but I didn't say nothin'
Then all of the sudden after someone pushed the button
I got a funny feeling like something was real wrong
Looked at her shoes and her feets was real long
Then it hit me, oh please God no
Don't let this ho turn out to be a John Doe
He pulled a fast one on me, yo
I guess that's one of those things that make you go
Shit!
The Pharcyde, "Oh Shit!"

    Professional Wrestling 
Oh, sweet Jesus, she's got a penis.
Mark Henry, WWE Monday Night RAW

    Video Games 
Not another dude...
Kagura Mutsuki upon confirming Amane Nishiki's measurements, BlazBlue: Chronophantasma

Oh, my stars and comets! He's a she!

Bridget: Hey, what's wrong with you? You suddenly went limp right in the middle of the fight...
Johnny: Ahh... Johnny... What have you done... You... you're a guy, aren't you!
Bridget: Sure am. This appearance... Well, it's kind of a long story.
Johnny: I can't believe I just tried to seduce another man...
Guilty Gear XX, in which Johnny learns the truth about the former Trope Namer (long before she proudly identifies as a transgender female in Strive)

Saika Magoichi: My, my... there are some beautiful girls on the battlefield today!
Mori Ranmaru: Who are you calling a girl!?
Saika Magoichi: Gah! I must be losing my touch! How can I make that mistake!?

Serra: I just make a policy not to make friends with girls who are as adorable as I am. I don’t need anyone else drawing attention away from me! So stay away from me, got it? Is that all sinking in?
(.....)
Lucius: I’m not a cleric. I’m a monk, so... So...
Serra: A M-Monk!?
Lucius: Yes...
Serra: But...to be a monk, don’t you have to... be a... Well...a guy?
Lucius: Yes. Yes, you do.

Pedestrian: Where you goin', pretty lady?
Châtenay: [Turns to face him and stroke his chest] Anywhere you want, mon ami.
Pedestrian: [Whimpers] Oh my goodness.
Arthur: [Trying not to laugh]

Toby: All the guys knew you as "Eric" back in school! I want my damn V-card back!!
Erica: Sorry, but once that hole's punched, there's no refunds.

    Web Original 
Wait, Bridget is a dude?
Oh god.
Oh God!
OH GOD!
— A new Anonymous that needs to lurk moar

Hal: Hey baby, what's your name?
Birdo: (in deep manly voice) My name is Susan.
Hal: Ahhhhhhh!
(Susan blows a kiss at him)
Bowser's Kingdom episode 6

That's a dick!
The Cinema Snob reacts to the aforementioned Sleepaway Camp

You know I'm in love with this chick
Because it seems we really click
There's no room for doubt
I think I'll ask her out
Wait... did you say she has a dick?

So I was looking up Shion's story... until I found out "she" was a "he"... GODDAMN YOU SNK AND YOUR POINTLESS SQUAREENIX-STYLE GENDER BENDING!!!
M.U.G.E.N user zigg4d gets a Bridget dropped on him

Natascha: How about ve get room and continue zere, Miss Kenshin?
(Kenshin blinks out of confusion)
Kenshin: Uhhhh....
Natascha: ?
Kenshin: I'm a boy.
(Natascha looks confused)
Natascha: ...vat.
Kenshin: Yeah.
Natascha: ...you very look like voman.
Kenshin: I get that a lot.

Alice: How about we raise the stakes? Winner gets to savor my tenderloin.
Mr. Krabs: (screams)

Vegeta: Look at you, Dodoria. You're always so damn proud! And now here you are, crying like a woman!
Dodoria: I AM A WOMAN!
Vegeta: Wh-What...?
Dodoria: I SAID I AM A WOMAN!!
Vegeta: *beat* WHAT???!!!

    Western Animation 
Quagmire: Hey there little lady. Why don't you turn around and show me your lower east side.
Lady: (in masculine voice) Sure.
Quagmire: Whoa, transvestite! Back off! Wait a minute, pre-op or post-op?
Lady: Pre-op.
Quagmire: Whoa, transvestite! Back off!

Peter: If you could be stranded on a desert island with any woman in the world, who would it be?
Quagmire: Taylor Hanson.
Joe: Taylor Hanson is a guy.
Quagmire: (laughs) You guys are yankin' me. "Hey, let's put one over on Quagmire."
Peter: No, he's actually a guy, Quagmire.
Quagmire: ...What? That's insane. That's impossible. ...Oh god. Oh my god. I've got all these magazines! Oh god!

Brian: Hey, is [Quagmires's sex-changed father] over there right now? We should go take a look.
Stewie: No, they had a fight. She's staying at the Marriott.
Brian: Aw, damn, I was just there!
Stewie: Really?
Brian: Yeah, maybe I saw him in the lobby and didn't even know.
Stewie: Oh no, you'd know.
Brian: Oh man, w-what do we call him now? We still call him Dan?
Stewie: No, and I'm not crazy about the name change.
Brian: What it it? Like, Danielle or Dana?
Stewie: No, Ida.
(Brian's eyes widen, gasps in horror and vomits nonstop for about 30 seconds before catching his breath)
Brian: AAAAAAAAAHHHHH!!!
Stewie: OH! WHAT?! WHAT THE HELL?! WHAT'S WRONG WITH YOU?!
Brian: I HAD SEX WITH HER!
Stewie: WHAT?!
Brian: I HAD SEX WITH HER AT THE MARRIOTT!
Stewie: AAAAAHHH! WHY?!
Brian: I DON'T KNOW! I DIDN'T KNOW IT WAS HER!
Stewie: OH MY GOD!
Brian: AAAHH!
Stewie: AAAHH!
Brian: AAAHH!
Stewie: AAAHH!
Brian: HOW DOES THIS HAPPEN?! WHEN THEY MOVE TO A NEW PLACE, THEY'RE SUPPOSED TO NOTIFY THE NEIGHBORHOOD! THAT'S HOW IT WORKS!
Stewie: HE DIDN'T ACTUALLY MOVE! HE'S JUST VISITING!
Family Guy, "Quagmire's Dad"

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