I jizz right in my pants, every time you're next to me, And when we're holdin' hands, it's like havin' sex to me, You say I'm premature, I just call it ecstasy, I wear a rubber at all times, it's a necessity
Bob, being the loser virgin or horndog he is, is... easily overstimulated— so much so that he ejaculates in his pants without even having sex, or in extreme cases, just from Alice talking to or brushing up against him. If he's in public, expect Hilarity to Ensue. If he's in private, expect Alice to be either extremely disappointed in Bob or proud of herself, depending on whether or not it was her intention.
In anime, a similar situation usually causes an explosive Nosebleed. Compare to Raging Stiffie. Contrast with The Loins Sleep Tonight. The end result of a Nocturnal Emission. A man ejaculating too quickly while making love is Speed Sex. Often combined with The Grunting Orgasm.
Happens in the anime version of Desert Punk to both Rain Spider and Desert Punk himself.
Scam in Rainbow walks past a whorehouse, sees one of the girls standing in front of it, and declares his intention to "become a man." But her room is on the second floor, and she goes up the stairs in front of him, wearing a very short skirt that provides occasional glimpses of her rear . . .
Comic Books
In Viz, this often happens to Billy No-Mates the Antisocial Teenager, such as when a female shop assistant measures him for a new pair of trousers.
Fan Fiction
Something must be said for this line from the Hetalia fic General Relativity:
"And for the very first time since high school, Matthew came in his clothes."
Film
In American Pie, Jim does this just before he tries to have sex with Nadia, ruining his chance. Twice.
In Forrest Gump, Forrest has a... moment with his girlfriend when she puts his hand on her bare breast, except he isn't wearing pants, and says "I think I ruined your friend's bathrobe." Even worse, said friend is in bed nearby, and has overheard what's going on.
Happens in a flashback in All That Jazz. When Joe Gideon was a boy, he performed a dance act at a burlesque show. One day just as he was about to go onstage a couple of female dancers started physically flirting with him and he had an accident. He had to go out and perform with a stain that caused the audience to laugh at him.
In She's Out of My League, this happens to the male lead right before he meets his new girlfriend's parents.
Non-humorous version happens in the Slasher MovieThe Funhouse. The deformed killer strangles the woman who made him go off too early and later starts hunting the protagonists who witnessed the whole thing.
One of the most frequent problems encountered during the sexual act is that of premature ejaculation. Should premature ejaculation occur, the Joy of Sex album comes equipped with *BOOM* BIG JIM SLADE. Big Jim, former tight end for the Kansas City Chiefs, is outfitted with various whips, chains, and a sexual appetite that will knock your socks off! Big Jim has satisfied women throughout the world, and the capital of Nebraska is Lincoln!
In Revenge Of The Nerds, Poindexter has this happen while watching footage from a video camera the boys snuck into the Alpha Bitches sorority house.
In Blankman, the title character has so little interaction with the opposite sex that a "thank you" kiss gets this reaction.
The Orgazmorator in Orgazmo causes this to whoever it is fired at, male or female.
Literature
Occurs in the Parrish Plessis series. Parrish tries to Show Some Leg to get past some security guards. It doesn't work until she taps into The Corruption to supernaturally boost her sex appeal, at which point it works a bit too well.
In Stephen King's The Dark Tower series, serial killer Jack Mort ejaculates whenever he kills someone by either pushing them in front of cars or dropping bricks from high windows.
Live Action TV
On Friends when Ross and Rachel have their first date he takes her on a "picnic" in the museum's planetarium display. As they get more intimate, Ross slowly rolls on top of Rachel, when she suddenly gasps.
Rachel: "Oh, God!"
They roll to their sides, and Rachel tenderly caresses Ross's face.
Rachel: "Oh... honey... oh, that's okay."
Ross: "What? Oh, no, you just rolled over the juice box."
Rachel: "Ohhh, thank God!"
Later, overlapping with a Noodle Incident, as their relationship is collapsing and they're having one of their more epic fights, Ross storms out angry, Rachel opens the door and screams out after him, "And just so you now, it's not that common, it doesn't happen to every guy, and it is a big deal!!!"
Happens to Mark in Peep Show. To be fair, Dobby was "accidentally" dry humping him at the time.
Actually a plot point and Chekhov's Gun in Glee: Finn's problem with premature ejaculation is what leads him to believe that he impregnated his girlfriend, even though he's never had sex with her. It's actually his best friend's baby, and he most certainly did have sex with her.
Comes up eventually in Sex and the City, with a boyfriend of Carrie's, whose family is ridiculously open about sexual stuff.
Kenny Powers does this in an episode of Eastbound And Down. He's drunk and making out with April in her bedroom.
Played for drama in Season 2 of Deadwood, when psycho mining expert Francis Wolcott has Carrie the New York Whore brought out to the camp. The audience finds out, one episode later, that he will only allow her to get him off through his trousers.
Saturday Night Live had the "Orgasm Guy" skit starring Rob Schneider, with the joke being the various nonsexual things that caused him to lose control (his favorite baseball team, beer in a bottle rather than a can, etc.)
Mike: Oooooh boy, this is gonna be great this is gonna be—oh. I'm done.
Seems to happen to Karen's husband Stan on Will And Grace: they have phone sex (or rather, Karen stands there fully clothed and says "Yeah, I'm naked") and after a moment or two she says "Oh, already? Good for you!"
Noah's Arc: This is what happens to Noah during his and Ricky's sexual experience in a flashback.
On Everwood Ephraim was making out with his girlfriend when she reached over his head to get some condoms. This reaching pushed her boobs into his face, and she kept wiggling on top of him to get to the condoms. They were quickly unnecessary.
Deconstructed in Scrubs when JD recounts how exactly he got his girlfriend Kim pregnant before their third date. He never actually had sex with her, just got overly stimulated and "fired his cannons" too early.
Turk: [trying and failing to contain snickering] What you're trying to tell us is that you never actually had sex with her?
J.D.: [after a brief pause] I didn't have a condom.
[Muffled giggles from Turk, Carla, and Elliot]
J.D.: And uh, we decided not to have sex because, here's the kicker, I didn't want to get her pregnant.
[Carla, Elliot, and Turk break out in hysterical laughing]
In Californication Charlie Runkle gets off in a strip club while seated during a lap dance. He tries to present it as a compliment. The stripper doesn't respond so well either way.
In Stephen Lynch's Live At The El Rey performance of the song "Superhero," he asks the audience to call out superheroes of their own, resulting in him doing a skit about Premature Ejaculator Man...
Rough Trade's "High School Confidential": "It makes me cream my jeans when she comes my way".
Actually happened to Heath, bassist of X Japan, during a performance at Lollapalooza 2010. No underwear + a vibrating bass?
In A Dance with Rogues, one optional sidequest involves a sexually frustrated mage offering to teleport you into the Dhorn barracks to retrieve some potentially damning evidence of your identity in exchange for sex. You have the option of making a show out of stripping down, which causes him to ejaculate prematurely and teleport you (naked) into the Dhorn barracks in a fit of rage.
Visual Novels
This is the result of Hisao's first H-scene with Emi in Katawa Shoujo.
In Sunstone, Anne gets a geek at a convention to do this by describing the sex games she'll partake in with Ally and Lisa that night. Lisa notes afterward that Anne can be really evil when she wants to.
In the Zero Punctuation review of Metal Gear Solid 4, after describing Snake and Otacon's "friendship," Yahtzee remarks that all the world's Slash Fic writers just experienced the female version of this trope.
Ray William Johnson of Equals 3 has the spoken version: "EPIC FACE, EPIC FACE, EPIC FACE, EPIC FACE, JIZZ. IN. MY. PANTS." Usually, this is set to a series of bizzare paused faces from the reviewed video.
One episode of Neurotically Yours has a fat Germaine wear an extremely revealing costume out in public as she waits in line to buy a copy of a new video game. The recurring pizza guy stalker behind her sees the revealing outfit and winds up completely ejaculating in his pants as a result.
Western Animation
Reverend Putty from Moral Orel does this in "Numb" when Orel's mother flirts with him.
In Family Guy, Quagmire does this after walking in on Peter and Lois being nudists.
King of the Hill: At a church group for born-again virgins, a character tearfully admits that while getting a massage at an arts and crafts fair, he "sinned his pants", then gets kicked out for being an actual virgin.
