5

Teen Wolf Has Amputee Sex With Characters from War and Peace

MGM Television

The Scenario:

Derek Hale, a teen wolf from MTV's 2011 Teen Wolf reboot, is out werewolfing one night when he suddenly catches the scent of other shape-shifting angst beasts nearby. He tracks the smell to the house of Fyodor Dolokhov and Anatole Kuragin (Nate for short), two characters from Leo Tolstoy's 19th century historical/philosophical epic novel War and Peace, who, according to this fanfic, are also werewolves. This helps explain how two 150-year-old literary characters are still alive in the modern era, because otherwise that would be too much suspension of disbelief for readers to swallow. It is also the least insane part of this story.

4

How to Train Your Dragon's Toothless Licks Chocolate off of Lilo & Stitch's Stitch

DreamWorks Animation

The Scenario:

"An Experimental Encounter" opens with Lilo & Stitch's Stitch traveling back in time to the island of Berk, which, for those of you who don't commit DreamWorks films to memory, is where How to Train Your Dragon took place.

DreamWorks Animation
And where any fond memories you do have of this movie will go to die.

Stitch accidentally gets covered in chocolate (as one does), and Toothless, the endearing hero dragon from the aforementioned dragon-centric film, swoops down to lick the chocolate off of Stitch's underwear bulges. Stitch has no choice but to masturbate to completion, because on the island of Berk, there is no God:

The moaning little alien lets two paws slip to his cock, madly stroking as one branch of the forked tongue stretches him wide open and the other one tickles the base of his nuts. With a grunt the blue balled little critter squeezes hard, cumming into the grass (...)

Where It Gets Really Weird:

What transpires next is a vicious oral sex fest between Toothless and Stitch culminating in a gigantic bukkake shower:

With a roar the dragon climaxes, showering them both with a white rain of sticky warm dragon seed.

Walt Disney
"Who trained you to do that?"

3

Superman and Jessica Rabbit Have Literal Cartoon Sex

Walt Disney

The Scenario:

On the surface, this seems to be much more familiar ground for erotic fan fiction. Clark Kent is relaxing in his home one stormy evening when Jessica Rabbit unexpectedly drops by to tell him that she has just left her husband, Roger. In the most childhood-ruining reveal since that time grandma's bathrobe fluttered open when she reached across the table for the marmalade, Jessica confides to Superman that Roger Rabbit literally has no penis.

"He's a eunuch." She said (...) "He doesn't have anything ... down there."

Luckily, Jessica came to the right place for curing absentee-genitalia marital strife, and a few moments later Superman is plowing her out on the balcony in the rain, more powerfully than an opportunistic locomotive.

Warner Bros.
"This looks like a job for Superman!"

2

Captain Kirk Has Sex With Metalocalypse's Nathan Explosion in Space

Williams Street

The Scenario:

"Heavy Metal" places the members of the band Dethklok from the animated Adult Swim show Metalocalypse into the distant future as they adventure through the galaxy aboard the U.S.S. Deathclock, which honestly isn't much of a stretch beyond what they do on the actual show. That's not the weird part.

The U.S.S. Deathclock, with the band's vocalist Nathan Explosion at the helm, docks at a nearby space station, where they meet the crew of the starship Enterprise from the original Star Trek. And by "meet the crew," we mean "Captain James T. Kirk has powerful, submissive anal sex with Nathan Explosion, a death metal cartoon character":

"Do you ... nnngh! Fuck!" Kirk - Jim, you couldn't call someone you were fucking by their last name - ground down on Nathan's cock, his knees pressing down into the mattress.

Picture that dialogue getting hammered out of the waterlogged, stuttering face of William Shatner. And that also is not the weird part.

Where It Gets Really Weird:

This isn't a few paragraphs of jerk-off material -- this is a four-part, 25,000-word novella, and only 2,000 words of that are devoted to Nathan Explosion engaging James T. Kirk's warp drive.

CBS Television Distribution
"Come on. 'Able to Ride Roller Coasters Danzig' isn't even in the top three of the weirdest things I've had in my ass."

1

Xander from Buffy the Vampire Slayer Has Sex With the Biker Mice from Mars

20th Television

The Scenario:

Xander, the goofball smartass from Buffy the Vampire Slayer, gets stranded en route to dealing with some vampires in Chicago. He wanders into the Last Chance Garage, owned and operated by the Biker Mice from Mars, because Xander's bus evidently broke down in Bad '90s Cartoonville.

Because of the vampire problem in Chicago and a building sexual tension between him and one of the bikers, Xander ultimately decides to move in with the alien humanoid cartoon mice, with predictably sexy results.

Brentwood Television Funnies
"Biker Mice are from Mars, women are from Venus ... Looks like we'll have to make do."

Where It Gets Really Weird:

Hey, remember when we were impressed by the 25,000-word epic above? Well, this one is 90 episodes and over 1 million words of lusty sci-fi fan fiction in which Xander gives in to his passion and has sex with a Biker Mouse:

"I never used to but your fur is very soft. It's like a good velvet (...) I think I like fur. At least tan fur over really hard muscles and under leather and jeans." He stole another kiss then pulled back to rub himself against the soft fur. He moaned, shifting back to do it again. "Oh, yeah."

Fur and leather are big boner triggers for Xander, because apparently he always dreamed of fucking a couch.

20th Television
"I will turn any sofa into a love seat."

Also, please notice that in this scene, Xander doesn't have a tail, whereas in the next chapter, he spontaneously grows one for no reason:

Then he laid down on top of the boy, his tail swishing in the air. That's what caught his attention. He looked back, flicking his tail. There was a second tail.

The tail is followed by fur and then full-on Martian antennae, effectively morphing Xander into a Biker Mouse.

Brentwood Television Funnies
"Finally."

It goes without saying that this transformation frees him up to have sex with sentient space motorcycles:

He grabbed the tease with his tail, planting him on his bike, face down so the vibrations would tease him.

"I feel like I'm part of a threesome. You mind, babe?" The bike shook her front wheel and slowly moved into deeper shadows.

In case we didn't stress this enough earlier, this fan fiction is over 1 million words long. That's longer than the longest novel in the English language, and it is fueled entirely by the author's desire to see cartoon mice have sex with the nerdy guy from Buffy. Hey, have you ever been so dedicated to a project?

Follow Eric on Twitter, or even better, check out the Webcomic he runs with his brother, Donuts for Sharks.

Related Reading: Okay, so the internet is a carnival of obscenity. But it's not like descriptions of ridiculously depraved sex acts are a modern thing. The Bible has a scene where Lot has drunk sex in a cave with his daughters. And while we're on the subject of religion, there's a surprising amount of sexy Christmas fan-fiction. And if you haven't had enough of being baffled by the Internet, read about the SWAT Kats fucking the town of Eureka.