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When you talk about erotic fan fiction, the word "erotic" tends to be redundant, because most people have no idea that any other kind of fan fiction exists. We've already talked about how brain-ticklingly insane some of these stories can get, but because the goal of the Internet is to boldly explore the furthest horizons of damnable madness, here are six more challenging pieces of fan fiction you can use to ruin any pleasant memories you might have had of the characters involved.

6
Barack Obama Has Unicorn Sex With Princess Celestia from My Little Pony

Andrew Burton/Getty Images News/Getty Images

The Scenario:

The story opens with U.S. president Barack Obama strolling out into the White House garden to masturbate with a bottle of beer and somehow missing the opportunity to make the "stimulus package" joke that all of us were expecting:

One hand under his head, he slowly begins stroking his penis. (...) he takes the cold beer bottle and places it sideways under his balls, letting the cool condensation seep into his sack.

Saul Loeb/AFP/Getty Images
Presidential historians call this "Coolidging."

Yes, we literally meant "masturbate with a bottle of beer," not that he was merely holding one while masturbating. You're in the world of erotic fan fiction now, this is how we roll. So anyway, at this point a majestic unicorn suddenly alights in the garden, prances over to the masturbating Obama, and starts giving him a blow job. Truly there has never been a more firm assurance that we are in the land of fantastical make-believe than that sentence.

Where It Gets Really Weird:

Still in his stupor, Barack let the unicorn to pleasure him with its mouth. His eyes rolled up into the sky, feeling the gentle sensation of the beast's soft lips rubbing against the skin of his cock, its saliva coating his shaft.

Hasbro Studios
"Friendship, with benefits, is magic."

Obama's new equestrian friend turns out to be Princess Celestia, the immortal ruler of the My Little Pony kingdom, who ventured into the world of global politics to comfort Barack Obama in his time of extreme loneliness. Obama (who, at the time of this writing, is the leader of the free world) accompanies Celestia to her pony kingdom, at which point he is forced to consume a magical potion of horse semen in order to stay alive:

"The elixir is transfigured from my excretion."

And Celestia doesn't deliver the serum in a convenient squeeze bottle or aluminum can -- she straight up craps it into Barack Obama's mouth:

Celestia positions her rear end over him. She lifts her tail and squats with her hind legs. (...) Her body shakes, and slowly from her ass hole, a drip of creamy white liquid begins to stream out. It lands in Baracks mouth, and instantly he begins to savour the warm chocolaty taste.

Jupiterimages/Goodshoot/Getty Images
"Forgive the grammatical errors. I was typing with one hand when I wrote this."

This raises several dozen questions about the biology of the creatures that inhabit the My Little Pony universe (or at least about what the author perceives it to be), and if you choose to investigate the matter further, we encourage you to never, ever share the results with us. Either way, we're considering everything we just read to be official MLP canon.

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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.

Where It Gets Really Weird:

I need an omega. Alpha werewolves can impregnate any gender, but only omegas can bear fruit (...)

MGM Television
"And lose these abs? Fuck nah, bros."

Fyodor and Nate inform Derek that they're looking for another male werewolf to bear their children and were wondering if Derek would be up to the task (there is a whole subgenre within the fan fiction community about men impregnating other men called Alpha/Omega, because of course there is).

Understandably unsure about their offer, Derek talks it over with his uncle, who responds by kind of raping him. Forcible incest proves to be just the thing to clear Derek's mind, and he agrees to let the two 19th century Russian werewolves inflate his stomach with wolf infants.

The first order of business is to make Derek an Omega (a man who can become pregnant), a procedure Nate performs by plunging his amputated leg stump into Derek's ass. This is surprisingly different from what we remember from the hilarious 1994 Arnold Schwarzenegger male pregnancy comedy Junior.

MGM Television
"Seems scientific enough. Fuck yeah, bros."

Nate took advantage of [the] moment of confusion, and in one motion introduced his crippled leg [into] Derek, to the knee (...)

Suddenly, in the middle of their explosive all-male werewolf sex triangle, Derek realizes that his uncle might have gotten him pregnant earlier during that whole "rape" fiasco, and runs out of the house to get an abortion.

- Where are you going? - Nate asked in a sleepy voice.

- [I need an abortion!] (...) I'm sorry, you'll have to find someone else!

Then, in perhaps the most baffling twist of all, Fyodor and Nate reveal that in this universe, it's impossible for men to get pregnant, magical ceremony or not. They just made the whole thing up to trick Derek into bed with them, which was admittedly a bulletproof plan, because who could resist the allure of carrying the child of two leering strangers?

MGM Television
"Fuck why, bros?"

Once again, this scenario leaves us with numerous questions we suspect we'll never have the answer to, such as who is the audience for this? Is there a large segment of the erotic fan fiction consumer base that A) has read War and Peace, B) watches the MTV version of Teen Wolf, and C) has a male pregnancy fetish? Again, it's a question we're happy to leave unanswered.

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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?"

This of course leads to a sequence wherein Toothless impales Stitch on his giant dragon schlong like a nightmare kebab and begins flying around in parabolic arches:

As he does the alien shouts, fearful of crashing, loosening his sphincter enough that as the dragons pulls out of the dive, momentum and gravity manage to work him in a little deeper.

Are you picturing it? This is one of those times you should be thankful these stories aren't illustrated.

DreamWorks Animation
The look on that dragon's face suddenly became incredibly sinister.

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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!"

Where It Gets Really Weird:

Clark moved to take Jessica inside, she stopped him. "No. We're not watercolours. We won't run," she said.

Yeah, you read that right -- in this fan fiction, Superman and Jessica Rabbit are living cartoon-humans who have to worry about things like inclement weather smudging their colors and Christopher Lloyd dipping them into vats of turpentine. Apparently, Jessica Rabbit just isn't worth masturbating to unless she's blurring that line of forbidden Saturday morning cartoon attraction you crossed when Daphne came on screen in Scooby-Doo while your parents were out at the store.

Warner Bros.
"Always keep your ascot handy, kids!"

Superman and Jessica enjoy pages of torrid lovemaking replete with dialogue that sounds less like the cries of unbridled passion and more like a schizophrenic bus driver's suicide note:

"Sshhlllrrrpppuppppp!" Her pussy squelched.

"Pllp! Pllp! Pllp!" The sound of Clark fucking Jessica's tits.

"AaAunHH! Huurrnh! Awwwuh!" Jessica squealed and screamed.

"Huunh! Auuhh! Hu!" Clark panted.

Michael Ochs Archives/Moviepix/Getty Images
"If you like the sound effects, be sure to check out my Police Academy stories, too."

Finally, mercifully, we get to the big finale, which does nothing more to console our harrowing discomfort:

It hit Jessica with the power of a thunderstorm. (...) Fireworks burst from her slick slit and steam shot from her ears as she rode the wave of the most intense orgasm she'd ever felt.

The author isn't employing a clumsy simile here -- fireworks and steam are literally bursting out of Jessica's body as she achieves orgasm, because, as the story has gone to great lengths to constantly remind us, she is a cartoon character, and that's apparently what cartoon orgasms look like. So Daffy Duck wasn't really angry all those times his skull whistled out clouds of steam like a tea kettle -- he was actually gluing his underpants to his stomach with wads of animated duck semen.

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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."

The other 23,000 words are spent fleshing out a massive episode of Metalocalypse. The author actually does a respectable job of imitating the show's style of absurdist humor, such as a scene wherein Toki, Dethklok's childlike rhythm guitarist with a tenuous grasp of the English language, orders a drink with a small umbrella:

"What? It's totally brutals," Toki said (...) "You can takes de umbrellas, stab somes-one in their eyes. Make greats album cover."

See, that's legitimately kind of funny and doesn't involve graphic descriptions of any characters ejaculating on each other. Author, if you're out there, just take out the gangbangs and submit it as a spec script. You were meant for more than this!

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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.

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