Shakedown Cruise
The chartered yacht, Luxe Deluxe, staggered as the iceberg hit it.
"This makes no sense!" Twilight yelled. "Icebergs can't maneuver and chase a yacht!"
"Well, we ain't got no power," Applejack said, wiping grease from her hands onto a rag, "and I ain't getting steam back to the engine room by m'self."
In the fading light of the day and backlit by the distant lightning of the oceanic storm, movement could be seen on the iceberg.
"Ooooooh," Fluttershy whispered.
Rainbow Dash grinned and pumped a fist. "I knew we'd be going head-to-head with a sea monster!"
"I had rather hoped you'd be wrong..." Rarity muttered.
The iceberg wasn't a monolith of ice calved off a glacier, but rather, seemed to be a pile of cyclopean blocks of ice, arranged into a non-Euclidean madness. From within a hidden vault reared a huge, formless polypous shape with luminous eyes. It reared up to its full height, hundreds of long tentacles waving, backlit by the setting sun.
Everyone screamed. Bulk Biceps shouted, "Cthulhu fhtagn! Yeah!"
"This is going to be just like the time we put the beatdown on Gloriosa Daisy," Dash declared, pounding a fist into an open hand.
"No, I believe it ain't gonna be that easy," Applejack replied.
The girls began to argue. The nameless shape reared high from its fortress of ice.
Fluttershy raised her voice, actually yelling for once. "Stop! I know this species!"
"From your animal studies, Darling?" Rarity asked.
Fluttershy looked at the deck.
"From her dirty tentacle-rape hentai books," Applejack said. "Which, if I find one more in Apple Bloom's room, I will hold ya personally responsible for, by the way."
Fluttershy blushed and nodded. "It, um, this species obeys vampire rules. If no one invites it, it can't come aboard. We just have to wait it out until morning, and keep trying to get the yacht's engine back so we can put some distance between us and the iceberg."
Trixie stripped her magician's dress off over her head, standing on the deck, fists planted on her hips, wearing only her stage shoes and purple thigh-highs, displaying her perky breasts, erect nipples, and Brazilian-waxed snatch. The cuffs of the thigh-highs were darker purple, visibly wet, with Trixie's burgeoning excitement. "Trixie is ovulating and extremely horny. Trixie invites—"
Everyone scattered and ran for belowdecks as tentacles wrapped around Trixie's torso, holding her a foot or two above the deck. Massive tentacles pistoned in and out of her asshole and vagina. Other, smaller tentacles wrapped around her tits and bound her wrists together, above her head. "Trixie regrets her choices and Trixie never wishes to ovulate again!"
Twilight and Applejack ran through the dining room, around a corner, through a bulkhead hatch, and found themselves in a dead end.
"The pantry," Applejack said. "I always knew I would meet m' doom in a pantry, just like Uncle Rotten Apple."
Twilight turned to face the hatch as the tentacles rounded the corner and entered. "I'll- I'll use my geode!"
"It'll be an honor to go down fightin' with ya, Twi." Applejack squared her shoulders and pulled her stetson down. "Geodes at sunset. Not the most traditional wild west duel, but I like our chances—"
Twilight gasped in time with the tentacles thrusting up her pussy. More tentacles held her—now stripped naked—upside down near the ceiling of the pantry and yet another tentacle teased her ass, preparing to slip its tip in. Her boobs bounced in time with the tentacles' sways and thrusts.
Applejack, also stripped naked except for her stetson, just played with her phone and sighed as a massive tentacle slammed repeatedly up her pussy, clobbering her uterus, and another speared her ass.
"You look bored!" Twilight shouted. "Y—you're playing Wordle on your phone while the tentacle monster dilates our cervixes?!"
"Farming Simulator."
"—what?"
"Wordle sucks. I'm playin' Farming Simulator. Don't tell no one," Applejack dropped to a whisper, "but I grow pears."
"The operative part of my objection was tentacles up our cervixes, not Wordle specifically."
Applejack pointed at her twat, speared wide and dripping sexual fluids. "Honestly? This ain't so bad as Big Mac's sleepwalkin'."
DJ P0N-3 hung suspended above her turntables, the tentacles wrapped around her naked abdomen as they played with her nipples and rammed her pussy.
Her arms were free, however, and she just kept spinning the disks, never missing a beat. Lasers and smoke and waving tentacles and thumping bass all joined together into a R'lyeh-style rave.
She did a particularly epic bass drop as a tentacle slid up her ass.
Pinkie and Dash ran, eventually finding themselves at the buffet. Pinkie's eyes shot to a new, even larger chocolate fountain.
"Oh my gosh oh my gosh oh my gosh," Dash shouted. "Here it is!"
The monster slithered into the dining room.
Pinkie glanced at the monster, then at the chocolate fountain.
"Cover me!" Pinkie shouted, yanking Dash's trousers and panties down to hobble her around her ankles before shoving her at the monster. "I'll owe you one!"
Pinkie sprinted for the chocolate and dunked her head into the pool as the sounds of tentacles entering an anus filled the dining room.
"Uncool!"
Free of the tentacles, but still naked and dripping sexual fluids, walking stiff-kneed like a penguin hen that had just squeezed out an ostrich egg, sworn to secrecy to never reveal the pear-related Farming Simulator secret AJ had revealed in extremis, Twilight stagged back up the stairs to the next deck. She heard a familiar voice and barged into a cabin.
Timber Spruce—whom she hadn't even realized was on board the yacht—was pounding Sunset Shimmer's ass while Flash Sentry probed her larynx with his cock. Sunset was tentacle-tied belly-down on a writing desk folded out from the wall.
"Sunset!" Twilight shouted. "My boyfriends! You're fucking both my boyfriends!"
Mouth more full of cock than Pinkie's had been of dessert at the buffet, eyes wide in panic, Sunset gave a tiny head shake and said "Nrrrrm!"
"Not our fault," Timber said, grunting as he rapidly blasted Sunset's ass. Flash shook his head no.
"How is this not your fault!" demanded Twilight.
Timber pointed as his ass. A tentacle was up it, controlling his thrusting as if he were a puppet and the tentacle in his colon a proctologist-puppeteer. Flash pointed at his own similarly-invaded bum.
"Oh," Twilight said, then reached a hand down to her own sloppy twat. "In that case, mind if I watch?"
Sunset gave a thumbs-up.
"You get back here!" Fluttershy shouted, shuffling as rapidly as she could with her sopping-wet panties around her knees and her skirt hiked up to reveal a freshly-waxed snatch. Her inner thighs and buttcrack glistened with her excitement.
The monster slithered down the passageway and around a corner in terror.
"I'm getting tentacle-raped today, and then you're signing my hentai collection!"
Wallflower Blush pulled the garden hoe from her bags. "They said I was mad to bring gardening tools on yacht week, but who's mad now?"
The tentacles slithered into her stateroom and began to split left and right to envelop her.
"I remember Gloriosa Daisy! I remember the vines well! Even if no one remembers that I was there!" She spun the hoe like a karate master with a bo-staff, over her head behind her back in a figure-eight, and then completed her display with the shaft of the hoe behind her back, the steel head forward, and balanced on one leg, the other leg tucked up, like the cover of a kung-fu movie DVD case.
"Heeee-yah!"
The tentacles hesitated.
"I'm the queen of the vegetables, friend," Wallflower declared. "I'm not trapped in here with YOU, you're trapped in here with—"
Fluttershy followed the noises and stuck her head into Wallflower's room. Wallflower was tied down by tentacles in the face-down/ass-up position, with the hoe's wooden shaft several inches up Wallflower's ass, as if she'd run afoul Vlad the Impaler's agrarian cousin. Several tentacles entered her pussy and penetrated her cervix, pussy juices running down the tentacles' shafts. She squirted as they stroked her g-spot. Another tentacle went up her throat, plucking her vocal cords like playing a stand-up bass.
"It's not a plant-form monster," Fluttershy informed her.
Lyra and Octavia leaned against the door to the stateroom—they didn't know whose stateroom it was, but the massive stash of hentai comic books, spiky dildos, and jars of anal lube spilling from one of the duffle bags gave them a hint—as the monster pounded on the door. Small tentacles found gaps in the seal and waved around the edges of the door.
Glass shattered as Bon Bon, clad in a Navy SEAL-style digicam wetsuit, swung through the porthole.
"Bonnie!" Lyra shouted, relief in her voice.
"Call me Agent Sweetie Drops."
Octavia's face went stiff as the stateroom became saturated with the smell of Lyra's panties getting moist.
Bon Bon pulled an old-timey hand-pumped bug sprayer from her backpack and attached to it a rusty steel can marked Manufacturing Date 1968. "And this is my back-from-retirement colleague... Agent Orange."
"Open the door." Bon Bon tossed off her swim mask and donned sunglasses "Let's defoliate."
The tentacles held Bon-Bon, Lyra, and Octavia—all stripped naked, although Lyra still wore one sock—off the ground, their arms trussed to their torsos and legs kicking ineffectually.
Tentacles spread all three sets of buttcheeks wide as more tentacles unscrewed the agent orange canister from the pump-sprayer and replaced it with one of the large jars of anal lube from the duffle bag on the floor.
Fluttershy stuck her head in the door. "Still not a plant."
"Oh heck," Ragamuffin said, "is this the end of the line for Ragamuffin and Rarity?"
They stood in Rarity's stateroom, staring at the bulkhead door as tentacles ripped it off its hinges. Rarity grabbed his hand in hers as the tentacles reared up and prepared to grab them. "I'll always be glad that now, at the end of the line, I met a man like—"
The tentacles held Rarity down on her bed and spread her legs wide, preparing to spear into her. Ragamuffin sobbed, held upside down by his ankles.
The tentacles made a ? shape upon encountering the extraordinarily diminutive size of Ragamuffin's own tentacle.
"Perhaps I should have held out for a different man at the end," Rarity muttered as a tentacle pressed into her ass.
Fluttershy, wet panties now fallen to hobble around her ankles, dress stripped off and boobs flopping in time with her rapid shuffling gait, chased the monster down the passageway.
The monster wriggled out a porthole and swung, outside the ship, up to a different deck.
"I saved my virginity for you!" Fluttershy cried, shaking an angry fist.
Treehugger sat on a lounger chair on the lido deck and lit a blunt the size of her leg.
The tentacles paused, hesitated. Treehugger was already naked.
"Toke?" she said, offering the blunt to the monster.
After about an hour, the others slowly began to get re-dressed and limped from their staterooms, closets, or other hiding places.
Eventually, Sunset Shimmer was the first to risk heading up to the lido deck. She peeked around a corner.
The tentacle monster reclined on a lounger, next to Treehugger's lounger, a joint in every tentacle and toking mellowly.