The Caterpillar — Alice In Wonderland Erotic Fan Fiction

Picture credit: Maggie Taylor

Winner of Shipwreck SF, San Francisco’s premier literary erotic fan fiction event.


“Finally” the Caterpillar mumbled to himself as Alice left. “Fucking whiny-ass white girls”. He took one last inhale from his hookah before inserting it back up into his anus and prepared himself for bed.

Times had been tough for the Caterpillar. He had grown more curmudgeonly in his old age and his drug problem, although very cool, had become all-consuming. There were only two things he truly wanted in life: to blossom into a beautiful butterfly, and to get his fuck on. However, at this stage, the Caterpillar had given up hope of ever filling the empty hole in his soul with a soul in his hole.

He took one last anal bong hit, and began to drift off. Just as his eyelids started to droop, he heard a rustling in the garden. There, through the dark, quivering blades of grass emerged a Dodo. The two stared at each other for a moment before the Dodo whispered, “You ‘Bottom Steve’?”

The Caterpillar was taken aback “Uh, no”.

“Oh, I’m meant to be meeting someone here. We’re going to Crusty Cavities”.

The Caterpillar was intrigued. “Crusty Cavities? As in teeth?”

“No my dear, as in buttholes. Crusty Cavities is a wondrous place! A place where creatures from far and wide gather to pleasure each other in all sorts of fun and horrifying ways. You want a rimjob from a raccoon? You got it! You want to freeze your turd and use it as a dildo on a dodo? You got it! You want a nice Cobb salad? You got it! Because they also do food there and it’s pretty good”.

The Caterpillar was speechless. All this time he’d been looking for a key to unlock his baser instincts, and as it turned out, that key was firmly lodged in Crusty Cavities.

The Dodo took pity on the old Caterpillar “Listen, looks like ‘Bottom Steve’ stood me up. You wanna come?”

“Me?” Asked the Caterpillar

“No, your shit-covered hookah pipe. Of course you!”

The Caterpillar’s mind began to whirl. Crusty Cavities sounded intimidating, but what if it was his only chance at rumpy pumpy?

The Dodo grew impatient. “Hellooo? Now or never”.

The Caterpillar nodded. “Let’s do this.”

They arrived at Crusty’s around midnight. The Caterpillar expected giant, wrought iron gates but instead found himself in front of a tiny wooden door. His nerves started to fray. The Dodo, antsy to get into Crusty Cavities, knocked on the door.

“I can’t do it! I’m going back!” The Caterpillar cried.

“Jesus what’s this now?” Muttered the Dodo.

“I can’t! I didn’t tell you this before but I’m a virgin, a crotchety old virgin! I don’t have any business being in a sex club!”

The Dodo had grown tired of the Caterpillar’s shit.

“Ok honey, first of all, it’s not just a sex club, I told you they did food and they have shuffleboard. Second of all, this may be your only chance to experience true happiness. Let’s look at the facts — you’re old, you’re not a butterfly, and the only person you really talk to is Alice and we all know that bitch cray. It’s time to get fucked or die fucking!”

Before the Caterpillar could respond, a voice came from behind the door.

“Password?”

The Dodo sighed “You are hard, Father William, the young man said. And your pubes have become very white. And yet you insist on giving me head. Do you think, at your age, it is right?”

The door flew open and The Caterpillar was immediately engulfed by the sights, sounds, and smells of Crusty Cavities. Inside, the place was enormous and opulent. Like if Buckingham Palace had sex with a sex club — a Fuckingham Palace, if you will. There were turtles going down on hares, unicorns pegging lions, and a rat king situation, but instead of entangled tails: penises. Every creature in the land was here and getting theirs. There were sheep sucking off horses, snakes erotically asphyxiating eagles, and a ring of centipedes eating each other’s asses, otherwise known as a ‘centipede centipede’.

The Caterpillar suddenly found himself alone and started to panic. His fuck-or-flight response kicked in, but as he went to leave, a familiar, floating face blocked his path.

“Cheshire Cat? What are you doing here?”

“Don’t you know?” Chortled the Cheshire Cat, “I own this place”.

The Caterpillar scoffed, “Makes sense. I should’ve known you’d be into this stuff”

“I’ll have you know that I originally wanted Crusty’s to be a bed and breakfast, but it turns out y’all are nasty, so here we are”

Just then, a Bear sidled up next to them.

“‘Sup Cheshire, who’s this giant turd?”

“Why this is my friend, the Caterpillar”

“Nice to meet you. The name’s Bear — Bear by name, Bear by nature”

“You know, Caterpillar, Bear here has a thing for feet”.

“Damn right, sure I’ve fucked all the centipedes, but I’m bored of them now. Whereas you, you’re fresh meat, fresh feet, fresh feet meat, gimme that sweet feet meat!”

The Cheshire Cat flashed his famous, shit-eating grin, “Go on, Caterpillar. Now’s your chance”.

The Bear led the Caterpillar to the center of Crusty’s and proceeded to unravel the Caterpillar’s years of sexual repression. There were feet in every possible orifice — asshole, peehole, earhole, eyehole, nosehole. Anywhere you could stick something, a foot was stuck there. The Caterpillar writhed around in pure ecstasy, filled with euphoria and Bear cum.

It wasn’t long before their antics caught the attention of the other creatures. Everyone stopped what, and who, they were doing, and gawked in awe. Slowly, the animals formed a jerking circle and began masturbating furiously over the pair of perverted podiatrists; chickens were choking it, monkeys were spanking it, and lizards were absolutely milking it. The Caterpillar looked out into the crowd and saw all these beautiful, contorted faces looking back at him. His eyes started to well up with emotion, among other things. This wasn’t just sex: this was love.

The floor shook as the creatures readied themselves for a simultaneous climax. There was a brief moment of silence and then, boom — a volcanic eruption of cum rose up through Crusty’s and blew a hole straight through the roof. The ejaculations were magnificent and synchronized, like a jizzy Bellagio fountain, and as the liquid pearls rained down on him, the Caterpillar opened his mouth to catch the falling cumflakes on his tongue. He could die happy now, but he wasn’t done yet.

A Unicorn beckoned. The Caterpillar knew what to do. He mounted the magical beast and crawled gently into its butthole. The Unicorn reared up onto its hind legs, furiously kicking and bucking. All of a sudden, it let out a symphonic wail, and from its ass emerged, not a caterpillar, not a butterfly, but a dazzling, winged vagina. The crowd cheered as the vagina flapped its labia and flew off through the cum-wrecked roof.

The Bear looked up to the sky. “Away, my sweet Vagi-fly, you are free now”.

The animals stood in stunned silence. The Cheshire Cat walked out to the middle of the club, cleared his throat, and addressed his patrons, “Cobb salads are on the house!”