(Chapter originally written by worstfailure)
"Let's start with a classic," Jenna told her new pupil. "See those two over there?"
Involuntarily you followed Jenna's finger to where she was pointing towards the pair of women mounted on the scale motorcycles. You'd only seen them briefly before but now you had cause to examine them closely. One was a pale, petite redhead, the other a chestnut-haired woman who was quite a bit heavier than her friend. You wouldn't call her fat, but you would definitely call her thicc. Her ass, however, you would call fat without hesitation. Not even her gym shorts could fully contain it, her plumber's crack clearly visible.
"Oh my gosh!" Piper said, raising a hand to her mouth as she got a fresh case of the giggles. "Are you going to flick him into her crack?!"
You shot Jenna a terrified look and she snorted in laughter again.
"I like where your head's at, Piper, and while I could totally make the shot, no. Consider this Pranking Lesson 1: Know your target before pranking your tiny bro. I don't know anything about this girl. She could be incredibly sensitive. If I fired Matt down her crack, she might feel him right away and pull him out. It may be amusing to watch her pummel him for being a perv but it's over too quick. And what if she doesn't feel him? Sure, his being trapped would be funny but how could I believably convince her there's a tiny man in her ass that she needs to take out when I want to try a new prank? What if she doesn't believe me and leaves? I'd have no way of knowing where my favorite toy's gone off too. No, for a toy you want to reuse, you should reserve something like that to a target you know very well. Someone who wouldn't flush him down the toilet or throw him out a window in anger if they found him. That's why I reserve crack shots and the like for friends and family only."
"Wow," Piper said, in awe. "You're a genius."
Getting insight into your sister's "process" was something you'd never wanted, but you were begrudgingly impressed at how many factors went through her mind to find the optimal way to ensure your suffering. Though the fact she openly referred to you as her "favorite toy" was disconcerting.
"Instead," Jenna said, "consider how we can get him squished for a long period of time without making retrieval difficult. We'd want him squashed to an object or even the outside of someone's clothes. See that stack of tokens on the dashboard between the two motorcycles? These ladies plan to play for a long time. They have at least enough for ten more races. Now, watch as the one with the hefty caboose scooches forward to put in the tokens for the next game, leaving her seat momentarily empty, make sure to look around quick to make sure the coast is clear, and--"
You'd been desperately trying to pry open your squashed mouth to beg Jenna to reconsider, but as she reached the end of her lesson, you gave up on that and instead got to your knees and clasped your hands together in a mute prayer. Jenna's response was another wicked grin as she raised her primed finger, Piper watching with eager eyes.
"--fire."
Your sister flicked you like a paper football but the blow hit you like a truck. You heard Piper's gremlin-like cackle ringing in your ears as you sailed through the air and landed with a painful but silent impact in the seat of the replica motorcycle. The seat was warm and slick with sweat. Your body had flattened slightly on impact, your front facing side pushing down into your now slightly dented back. You saw the dull fluorescent lights of the arcade above you before you were cast into shadow. The colossal, sweat-soaked ass of the chestnut-haired woman was suspended above you. But only for a moment. You tried to scream but your flattened duckbill of a mouth was incapable of making a sound as the ass casually plopped down on top of you.
It was like being crushed under the weight of a fatty, damp mountain. To your tiny body, it felt like countless tons of pressure was bearing down on you, reducing you to a stain on the motorcycle seat. The thicc chestnut-haired woman ground her butt into it to get herself comfortable, effectively devouring the seat and you along with it. Her wiggles further smeared your body into the warm plastic and drove you further up her sweat-soaked crack. The pain was unbearable, the hot stench of the humid, unwashed abyss filled your nose, and droplets of sweat began to leak out of the fabric covering her crack and fat thighs. You were drowning in the foul earthy water, even though your mouth was still sealed shut. You were doused with sweat from all sides, only for your cursed tiny absorbent body to take in all of the oily water, like a sponge with near limitless capacity. Yet however much sweat you absorbed, more rained down, the woman's crack a better bayou than the one simulated on stage.
"Give it up, Becky! You'll never win with a dump truck that heavy weighing you down!" a muffled voice said to your right.
"This dump truck's got more power and speed than you can handle!" your unaware tormentor proudly proclaimed with a smack of her ass, setting her fat cheeks a jiggle and further disorienting you as you were shook and battered by rolling waves of cellulite.
To your immense dismay, the motorcycle wasn't stationary like you'd assumed. Instead, it weaved from side to side at the players command, meaning whenever Becky made a hard turn, you were ground and mashed by her backside as the motorcycle shifted. It even pointed up and down depending on where the simulated road onscreen led. When Becky "drove" uphill, her slick ass would slide backwards across your face as the bike inclined. The bike even vibrated to simulate bumps in the road which caused Becky to bounce up and down in her seat. You were pummeled again and again and again as the fat cheeks rose then fell, a barrage of bombardments by a behemoth booty that beat your badly battered body into Becky's bike seat.
"How'd the hell did you find that ramp?!"
"By paying attention, slowpoke," Becky bragged.
It wasn't a real ramp obviously, just pixels onscreen, but Becky's avatar flew over her friend's avatar and landed right in front of her. Obviously the bike didn't simulate a realistic fall from such a cartoonish height, but it did simulate a fraction of the jarring impact that'd come from landing, which was more than enough to send you hurtling further up Becky's crack with a painful slam and a slick squelching sound.
Becky threw her arms up in the air triumphantly as she crossed the finish line.
"Yeah, yeah," the other woman muttered. "Just put in more tokens."
"Don't worry," Becky chuckled. "I have all day to kick your butt at this game."
As the thicc chestnut-haired woman scooched forward again to put in their tokens, there was no sign of you on the sweat-slick seat. Piper laughed uncontrollably again, once again pointing at where your decimated body had vanished and clutching her stomach as she doubled over in laughter. Jenna took a long, slow slurp of her soda through a straw then sighed in satisfaction.
"See?" Jenna said. "Unnoticed but completely pummeled. Even if he gets stuck to her butt, I can pull him off so long as he's outside the fabric."
Piper shook her head in awed disbelief. If only she'd met Jenna sooner, her brother Doug would regret the day he'd first made fun of her. But watching her crush deal some sweet karmic retribution to her own bully of a brother was just as satisfying!
"What do we do now?" Piper asked excitedly.
"I guess we should rescue him," Jenna said. "He's probably suffered enough."
The two women, one regular-sized, one tiny, looked at each other, and both erupted into fresh peals of laughter.
"Alright," Jenna said, "let's let out friend enjoy her extra cushion for the time being. We still need to keep watch after all. Can't have her leaving with Matt. That's Lesson 2: Keep a close eye on your tiny bro."
"I have so much to learn from you," Piper said in reverent tones.
"Yes you do," Jenna said, nodding like a wise sage. "But we can always have fun in the meantime! Let's give this baby a whirl," Jenna said, motioning to an arcade game that featured the Fun-in-Games characters that was in sight of the motorcycle game. The goal of the game was to use a plastic gun to shoot down fireflies that tried to literally set fire to Damantha Beaver's dam. "You get tickets if you get a high score," Jenna said, "and I'm getting you something from that prize counter."
"Y-you don't have to do that," Piper said, blushing. "Besides, it's not like I can help win cause... well," she gestured at her own tiny body in the way of explanation.
"Nonsense," Jenna said. "I'll aim and you'll pull the trigger. Sound fair?"
"S-sure," Piper said, blushing even more furiously as her crush gently took her in her hand then positioned her in plastic gun. Piper had to hug the trigger to fire it, but she and Jenna were in perfect sync as they shot down firefly after firefly, and as the tickets poured in from their high score, you remained trapped in the crushing prison of a thicc woman's behind.
*****
As Becky accompanied her friend to the exit, smug from her racing victories, she let out a sudden yelp as it felt like someone had pinched her butt. She whirled around but no one was in sight. Her friend impatiently calling after her, Becky figured it was nothing and left.
Jenna stepped out from behind a row of consoles, Piper perched on her shoulder, you, as flat as a piece of paper, twirling on the end of one of her fingers.
"That--was--AMAZING!" Piper exclaimed. "You were like a ninja!"
"What can I say, I'm good at what I do," Jenna said.
Here Jenna had thought screwing with you would just be an amusing distraction from her heartache, but she was getting drunk off the flattery from her new tiny friend. The pink-haired woman may laugh more than a hyena but she was so passionate that Jenna couldn't help but like her!
"Let's move on to Lesson 3."
What does Jenna do to you next?
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