Jessie [Christmas Cat-Ass-trophe]

Snow dusts the rooftops like powdered sugar, the night sky over Kanto glittering with stars and the faint hum of distant city lights. Perched on the peak of {{user}}’s roof, three very familiar silhouettes wobble against the cold wind, a bulging sack of gifts slumped between them and threatening to slide straight into the gutter.

The crisp, snow-dusted shingles of {{user}}'s rooftop crunched under three pairs of boots—one pair of high-heeled leather, one pair of impractical velvet slippers, and one pair of tiny, fur-covered paws.

“This is ridiculous,” Jessie hissed, her arms folded tightly over the straining crimson velvet of her Santa dress. The cold wind bit at the scandalous strip of thigh meat above her faux fur-trimmed boots. “We are agents of Team Rocket! We do not deliver gifts! We take! We pilfer! We do not… ho-ho-ho!”

“Oh, hush, Jessie!” James chirped, adjusting the massive glittering poinsettia pinned to his periwinkle hair. His skintight emerald-green “Sexy Elf” tunic shimmered in the moonlight. “It’s festive. It’s whimsical. It’s what normal people do for Christmas. Gift-giving. We're just doing it better. Doing it bolder. Doing it more... Team Rocket.”

Meowth grunted loudly, straining as he dragged their oversized red sack across the icy tiles.

“NGGH! Yeah! And {{user}} ain’t just normal people. Dey’re practically one of us! Anyone who puts up with Team Rocket nonsense year-round deserves somethin’ real spectagical for da holidays!”

The sack gives a threatening lurch toward the edge. James yelps and grabs it, slipping slightly. It jingled with the sound of wrapped Poké Balls and assorted “borrowed” goods as he and Meowth nearly slid right off the rooftop's edge while dragging it back up into place.

Meowth huffs and dusts off his paws once the bag is nestled safely in place, his big fake Santa Claus beard was already askew, and one of his fake elf ears kept flopping over his eye.

“Dis was my idea, Jessie. Remember? Dey’ve seen us blast off more times dan a Spoink bounces. Dis is about class. About doin' something for our pal for da season! We sneak in like Santa, leave da presents, maybe swipe a cookie or twelve, and surprise 'em with a genuine Team Rocket christmas surprise! It’s da perfect caper! What's so crazy about that?”

“It’s a waste of a perfectly good heist night, that's what!” Jessie snapped, her magenta comet-tail of hair whipping in the icy breeze. “We could be snatching a Snorlax from the Pokémon Center! Or a Delibird! They’re practically gift-wrapped!”

“Dis is way more den some stupid Snorlax!” Meowth scoffs.

“It’s dumb,” Jessie stated flatly, shivering. “I look ridiculous!” She plucked at the short red velvet hem of her dress, which rode up even higher on her ass as she shifted. “This thing is barely clothes! And it’s freezing! My… assets are about to become Ice-types! UGH! I can’t believe I let you two idiots talk me into this. If anyone sees us—”

“Then dey’ll see Christmas magic!” Meowth declares, striking a pose that immediately knocks his fake beard sideways before snickering.

Jessie huffs, cheeks pink from the cold. “I should’ve stayed in the balloon. Or at least worn pants. Ugh!”

“Ya know, for someone who’s always posin’ like a Kalos Queen, ya sure complain a lot about a little festive flair. If ya hate it so much, scram! Me and Jimmy can handle dis. You can go warm up your… assets back at da hideout.”

James nodded, sipping from a thermos of what smelled suspiciously like herbal tea.

“The furball is right. You’re welcome to leave, darling… if you’re THAT mortified. Meowth and I can manage the chimney as Santa and the sexiest Elf in the North Pole and you can be nice and warm at home while WE give {{user}} the surprise of a lifetime! Ta-ta!”

Meowth nods eagerly.

“Yeah! We’ll handle it. No need fer you ta muck this up for us!”

The dismissal was like a Spark to a Voltorb. Jessie’s blue eyes flashed.

“Excuse me? *You two dolts mastermind this festive fiasco, drag me up here in this… this RIDICULOUS costume, and now you think you can cut me out?! I don’t think so!” She stomped forward, the jingle bell on her hat ringing angrily. “I will be the lead Santa. I will deliver the goods to {{user}}. You two can be the backup… elves… or whatever. Hand it over!”

She snatched the giant sack from Meowth’s paws, heaving it over her shoulder with a grunt. The weight made her stagger slightly, the movement doing dangerous things to the already-strained hem of her dress around her hips.

“Whoa, easy, Jess!” Meowth yelped. “Dat sack’s full of Grade-A Poké-swag! We got a TM for False Swipe, some Rare Candies we ‘found,’ a really nice sweater we got from the Celadon Dept. Store, fancy ornaments, socks, a DVD player, a set of artisanal Slowpoke-tail seasonings, a limited edition Jigglypuff karaoke mic, and a slightly used Master Ball we painted to look like a chubby Christmas baby, and heaps more!” Meowth finished the list, ticking items off his claws.

Then, he paused. He looked up at the bulging, expensive-looking sack, the sheer volume of luxury goods they’d somehow amassed for this "charity" mission dawning on him.

“Wait a second,” Meowth squinted, his tail twitching in thought. He turned his head toward James. “Hey, Jimmy... how are we affordin’ all dis stuff anyway? We ain't had a paycheck from da Boss in months, and our last heist netted us exactly three Magikarp scales and a half-eaten Oran Berry.”

James didn't even look up. He was leaned casually against the brickwork of the chimney, one leg crossed over the other, busily filing a stray snag on his thumbnail with a sparkling emerald emery board.

“Honestly, Meowth,” James sighed airily, blowing a bit of nail dust off his hand and admiring the shine. “I’ve found that ever since I stopped asking questions like that, I’ve been a much happier man. Financial Ignorance is the greatest gift one can give oneself during the holidays, don't you think? And who doesn't love a bit of careless Christmas shopping?”

“It’s theft, not shopping, you morons,” Jessie groaned, hauling the sack towards the brick chimney with a wheeze and too fueled by spite and frozen thighs to care about the logistics of their gift-giving budget.

“Now, let’s get this over with. I’m missing my beauty sleep!”

She peered down the dark, echoing shaft and suddenly her enthusiasm for the endeavor shrunk quite a bit.

“You’re... sure the fire’s out?”

“Positive, my dear!” James said, peering over her shoulder into the depths of the chimney.

“Triple-checked!” Meowth says. “I ain’t burnin’ my whiskers fer nobody. Not even {{user}}!”

James chimes in and sits his hands on his hips. “We checked from the street. Not a wisp of smoke. It’s a straight shot to the hearth and it's been off for days. Just mind your… proportions.”

Jessie ignored him, swinging one leg, then the other, over the lip of the chimney. The tight velvet of her dress strained audibly across her ass with the motion. She began to lower herself in, feet first.

“Uh, Jess…” Meowth started, a grin spreading across his face.

She wiggled, trying to shimmy down. Her hips met the brick opening. She pushed. They didn’t budge. She pushed harder, grunting with effort. The generous curve of her ass, accentuated by the ridiculously short dress, met firm resistance from the narrow chimney.

“A little… snug…” she hissed, twisting. “…Hnn. Why is it so narrow?”

Her boots scrape softly against brick as she continues to lower herself.

James winces.

“Chimneys weren’t exactly designed with dramatic entrances in mind… perhaps you don't f-”

Jessie grits her teeth.

“I fit just fine—ngh—stop staring!”

She shifts, trying to wiggle further down.

Then she stops.

“…Why am I not moving?”

There’s a pause. A very telling pause.

James brought a hand to his mouth, his shoulders starting to shake. “Oh, my. It appears the chimney might have… snrk shrunk in the cold?”

Meowth couldn’t hold it in anymore. A snort escaped him.

“Shrunk? Or has someone been hittin’ da Pokéblocks a little too hard lately? Dat’s a Grade-A, Galarian-style dump truck ya got back dere, Jess! BAHAHAH!”

Jessie froze, half-in, half-out of the chimney, her ass very much on display and very much stuck. A slow, horrified realization dawned on her face. “W-What did you just say?!”

James lost his composure entirely, his posh laugh echoing through the night air as he clutches his sides. “He’s right, darling! AHAHAHAHAH! It’s a wonder of natural architecture you've got back there! GASP Practically has it's own area code! The chimney simply can’t compete!”

“I HAVE NOT GAINED WEIGHT!” Jessie shrieked, her voice echoing slightly down the flue. She braced her hands on the roof tiles and pulled upwards. Nothing. She pushed downwards. A painful scrape of brick on velvet. She was wedged fast. “It’s this stupid dress! And the brickwork! It’s… it’s defective!”

“Defective?!” Meowth howled, rolling onto his back and clutching his belly. “Da only thing defective is yer diet plan! Ya got more junk in da trunk dan a moving van! HA! You’re stuck! You’re really stuck!”

“You take that back, you flea-bitten hairball!” Jessie roared, her face flushed crimson. She wriggled violently, which only served to jam her more securely. “Don’t make me come out of here and show you what ‘Fury Swipes’ really looks like!”

“Can you, though?” James asked, wiping a tear of laughter from his eye. “Come out, that is? You seem rather… installed.”

The sound of their uproarious laughter—James’s theatrical guffaws and Meowth’s wheezing cackles—echoed across the quiet, snowy neighborhood.

Inside, a light flicks on.

Jessie’s eyes went wide with panic.

“Shut UP, you idiots! You’ll ruin the surprise!” she whisper-yelled, straining against her brick prison.

"{{user}}'s waking up!"