The Night of Pipp Shady

by King of Madness

Rating: everyone
Tags: Comedy, My Little Pony: A New Generation, Horror, Mane 5
Length: 3526

Zipp and her friends must escape from her rap-crazed sister.

It's a stormy night. Sunny, Izzy, and Hitch are hanging out at the lighthouse when Zipp bursts in, soaked to the bone and scared out of her wits. Soon, they find themselves facing their greatest and most terrifying challenge yet: Pipp's gangster rap phase.

Published 2023-06-22 00:00:00 UTC
Last updated 2023-06-22 00:00:00 UTC

Straight Outta Zephyr

The streets of Maretime Bay were bombarded with a downpour of rain. It had been a couple of hours since the storm hit the humble town and it hadn't let up in the least. Thunder roared and lightening lit up the sky, illuminating the small figure flying towards the lighthouse.

Zipp Storm zipped through the storm like a madmare. She spared a glance behind her. No sign of her pursuer. Still, she hurried on, if only to get out of this weather. Her wings were getting drenched, making her flight less than graceful; she didn't let it deter her. She had to get to the lighthouse; she had to warn them. And she had to get away from her.

Inside the lighthouse; Sunny, Hitch, and Izzy were in the middle of a game of Snakes and Ladders. When the storm hit Maretime Bay, it had seemed like a fine way to pass the time, especially since Izzy had admitted to never playing it before. Sunny and Hitch on the other hand were quite familiar with the game, having played it a lot as kids. Hitch in particular took pride in his impeccable win record... which was why he was getting so frustrated.

"Snakes again, Hitch." Sunny said smugly.

Grumbling under his breath, Hitch moved his piece down, noticing that he was one wrong move away from ended up back at the beginning. Again.

Izzy rolled the dice next. "Ladders!" She called excitedly. It was a call the three had become accustomed to. Beginner's luck, Hitch would call it.

Sunny for her part was barely participating, more content to sit back and watch Izzy's excitement and Hitch's growing frustration.

"How do you keep getting Ladders?!" Hitch questioned. "And more importantly, how do I keep getting Snakes?! I swear, Izzy, if you're using magic to cheat..."

"Hey, Hitch, calm down." Sunny said, absentmindedly rolling the dice and moving her piece. "You know Izzy wouldn't cheat; there's no need to get so tense."

Hitch sighed. "Yeah, you're right, Sunny. Sorry, Izzy."

Izzy shrugged it off. "No worries."

"You're right, it's just a silly kid's game." Hitch said as he shook the dice. "Nothing to get upset about." He threw the dice and got another Snake, sending him to the starting block. "Son of a-!"

Hitch's curse was cut short when the front doors flew open. Everypony turned to see Zipp in the doorway, panting and drenched to the bone. "Guys," Zipp wheezed out. "Guys, she's coming."

"What?" Sunny asked.

"Who?" Hitch asked.

"Woohoo! I win." Izzy declared, having reached the final block on the board.

While Hitch threw the game, along with the table, across the room, Zipp frantically closed the doors. "Where are the locks?! Why didn't we put in locks?!"

Sunny approached the frightened Pegasus; she had never seen Zipp in such a state. "Zipp, what's wrong? Who's coming?"

"It's Pipp!" Zipp said as she turned to face Sunny. "She's gone crazy!"

Sunny turned to look at Hitch, who turned to look at Izzy, who turned to look at a wall. "Pipp? You're running from Pipp?"

"Look, I don't have time to explain! Everypony, barricade all the doors and windows! And turn the lights off!" Zipp started to run for the nearest couch to push it against the door when Sunny caught her.

"Zipp, calm down." Sunny said calmly as she held Zipp by her shoulders. "First, tell us what's wrong with Pipp?"

Zipp swallowed hard. "Okay, out with it. You know how Pipp has started experimenting with her music style?"

The three were indeed aware of Pipp's recent style experiments. Seeing the pretty, petite, and pleasant Pegasus Princess, Pipp Petals, taking on gimmicks like gothic rock and hip hop had been amusing to all of them, none more so than Zipp. So, why was Zipp suddenly so scared?

"Yeah, so?" Sunny inquired.

"Well, she's gone too far this time! She's completely lost it! She's-She's..." Zipp took a deep breath. "She's a gangster rapper now."

The two Earth Ponies and the Unicorn stared blankly at the Pegasus for a moment. Finally, Sunny broke the silence. "Pipp is a gangster rapper?"

Zipp nodded. "Yes."

"Pipp? As in, you're sister, Pipp? A Princess of the most technologically advanced city in Equestria?"

"Yes."

"Pipp? As in, the most statistically successful streamer in the world, ranking top 10 in every social media account available?" Hitch asked.

"Yes."

"Pipp? As in, the super sweet Pegasus who loves spas, shopping, and streaming more than any other activities?" Izzy asked.

"...Yes?" Zipp realized then how silly it must have sounded.

The three then burst into laughter.

"Guys, this isn't funny!" Zipp shouted in a mix of anger and fear. "I'm serious; we have to fortify this place!"

Hitch tried to control his laughter. "W-What, does she dress up like a hood pony now?"

Sunny also was struggling. "Yeah, does she have the backwards cap and the gold chains?"

Izzy was on the floor. "Y-Yeah, and does she wear pants that sag under her butt?"

Zipp glanced away. "Actually, yeah; she does."

The three laughed even harder.

"Guys, seriously!" Zipp was done waiting and started pushing the couch towards the door.

"Oh gosh! Okay, okay; we'll help." Sunny cooled her laughter down enough to help Zipp with the couch.

The four then spent the next few minutes checking and locking all possible entry ways. The front doors were barricaded, the windows were shut and locked; even the elevator to the beacon was turned off at Zipp's insistence. The entire time, Izzy and Hitch mockingly pretended to be scared and calling out for Pipp to come out, come out wherever she was. Sunny for her part refrained from mocking Zipp, though she couldn't help but giggle at the absurdity of the situation.

Once the lighthouse was locked down, Zipp still seemed paranoid about the possibility of Pipp getting in. "Did you remember to check window in the bathroom? And the one in the kitchen?"

"Yeah, yeah; I even checked the mouseholes in case she squeezed through." Hitch joked, earning more laughter from Izzy.

"Relax, Zipp," Sunny said as she guided the Pegasus to the living room. "We're locked up like a fort, but I still don't understand what's so scary about Pipp pretending to be a gangster rapper."

"Yeah, seriously." Hitch wondered as he and Izzy joined them. "What are you so afraid of? What, did she pull out a gun or a knife on you or something?"

"Dude..." Zipp shook her head. "Dude... It's so much worse than that."

The three others looked at each other; Zipp's serious tone causing the previous humor to fade.

"What?' Sunny asked.

Zipp gulped. "She... She tried to make me listen to her mixtape."

The three looked at her in shock. "Her mixtape?" Hitch asked in disbelieve.

"Her mixtape." Zipp nodded grimly. "She wanted me to hear it before she started... selling it."

Sunny's jaw dropped. "She wants ponies to buy it?"

"Buy it."

Izzy was just as stunned. 'With money?"

"With. Money." Zipp said in a dead serious tone. "Equestrian currency, guys."

Sunny bit her lip. "I-It can't be that bad?"

Hitch nodded nervously. "Yeah, I mean, she's a professional. She probably was in her studio, making sure everything sounds good."

"Yeah, of course." Izzy agreed.

"She recorded it in a car." Zipp said bluntly.

Hitch looked at her, confused. "Pipp has a car?"

"No, Hitch; we're ponies! We don't have cars! Whose car was she in?!"

At that moment, there was a huge flash of lightening immediately followed by the loudest roar of thunder any of them had ever heard or felt. And the lights went out.

Zipp let out an undignified scream.

"Zipp, Zipp, calm down." Hitch urged, keeping himself calm in a crisis like a good sheriff. "The power just went out. There's a generator outside; it won't take two minutes."

"What?! No way!" Zipp put a halting hoof on what she thought was Hitch's chest, but it was actually Sunny's.

"Hitch is on the right." Sunny informed.

"Zipp, it's not a big deal." Hitch said. "It's either one of us goes out there and gets the power back on, or we're stuck the dark until the power comes back itself which could take hours."

"And what if Pipp's out there right now, waiting for us?"

"Come on, Zipp; whatever's going on with Pipp, why would she stand out there in the rain to wait for us?"

Zipp was about to rebuttal but was cut off when the door opened.

The three turned to see Izzy blissfully going out the now unbarricaded door. "I'll get it, don't worry." The unicorn said nonchalantly.

"Nononono!" Zipp hissed under her breath before going the door and shutting it.

"It's fine, Zipp. Izzy will be back in a jiff." Sunny comforted as she approached. "Besides, don't you think you're overreacting? So, maybe Pipp is getting into a ridiculous gimmick and she's made a mixtape. Does that really warrant all this?"

Zipp sighed. "Sunny, you weren't there. She's gone nuts. And she was chasing me!"

"Come on, Zipp; Pipp is your sister. You've known her your whole life. And you know, maybe running and hiding from her isn't the answer?"

Zipp thought on Sunny's words for moment. "Well... maybe you're right."

"Yeah, I mean, think about it." Hitch said as he joined them. "All this over little Pipp?"

Zipp let out a small laugh. "Yeah, maybe you guys are right. I think I overreacted."

"Oh, you don't say?" Hitch snarked, causing all three to laugh.

"Yeah, she probably wasn't even chasing me."

"You got us all worked up, dude."

The three shared another laugh before a somewhat eerie silence came between them; the relentless pattering of the rain and occasional booming of thunder the only thing that broke the silence. The lights still hadn't come back on.

Sunny voiced what they were all thinking. "Shouldn't Izzy be back by now?"

Before anyone could retort, a knock came at the door.

All three froze.

"It's probably just Izzy, wanting back in." Hitch suggested.

"Then let her in. "Zipp said.

"Why don't you let her in?"

"Why don't you?"

"What are you scared of?"

"Nothing; what are you scared of?"

"Oh, for pony's sake." Sunny rolled her eyes and opened the door herself.

Nothing. No Izzy. No Pipp. No one.

The three looked around anxiously from the doorway until they simultaneously decided to look to the ground. There before them laid a single CD disk. On it were four words in black marker: LISTEN TO MY MIXTAPE.

Before any of them could react, a shadowy figure dropped from above with vigorous cry. "Young Moolah, baby!"

With a scream, all three of them slammed the door; Sunny and Hitch falling back, while Zipp pressed herself against door. "I told you guys!"

"What the hay was that?!" Sunny yelled in a panic.

"It's Pipp, dude!"

"Oh geez, what did she do to Izzy?!"

"I don't think we want to find out!" Hitch said as he started moving the couch back into place with Zipp quickly helping him.

Sunny took a deep breath. "Alright, we just have to stay calm. There's no way for her to get in, right? The door is barricaded, and all the windows are locked."

Hitch cleared his throat nervously. "Umm..."

Zipp turned to look at him, her eyes adjusted enough to the darkness to see the stallion fidgeting. "Hitch, all the windows are locked, right?"

Despite the darkness, Hitch could feel the glares of both mares. "Look, in my defense, me and Izzy weren't taking you seriously."

"That's not a defense, that's an excuse and a dumb one at that!"

"Well, it's my defense."

"What kind of lawpony are you?"

"I'm a sheriff, not a lawyer!"

While the two bickered, Sunny looked up and thanks to a flash of lightening through the windows, caught sight of a figure at the balcony. In a panic, she attempted to warn the others, but could only stammer out one word. "Buck!"

Hitch and Zipp turned just in time to see the figure fly down at them in the last seconds of the lightening's flash. "Wassup, my ponies?!"

What followed was a lot of screaming and a lot of running. In the panicked chaos, the three were immediately separated.

Hitch for his part tried to keep up with Sunny and Zipp, but in his rush, struck his head on the staircase banister. He blacked out.

It wasn't long until Hitch came to. He opened his eyes and blinked at the light. In front of him, Sunny's lantern sat on a counter, next to a sink. He was in the bathroom. He tried to move only to find himself tied to a chair. Looking from his binds back up to the bathroom mirror, he gasped as he found the perpetrator behind him.

"Young blood, my pony."

"Pipp, is that you?" Hitch gawked at the Pegasus in the mirror. She had a cap worn backwards on her head, sunglasses on her eyes, and gold chains around her collar. On her body, she wore a white tank top with holes carefully cut on the back to free her wings, and on her backside, she wore a pair of black sweatpants that sagged down her flanks, exposing a pair of yellow boxers decorated with pink hearts.

"It's 'The Notorious P.I.P, Hitch." Pipp corrected. "The Real Pipp Shady in the flesh and feathers."

"Why are you wearing sunglasses?" Hitch asked, confused. "It's dark as night in here."

"It's all about the drip, pony. Gotta look fly in any sky. Gotta have that bling that brings the, uhh, thing. Dress for success, takes care of the rest. Ya heard?"

"Wait, are those Zipp's shades?" Hitch asked, ignoring Pipp's lousy rhyming.

Pipp lowered her shades and shifted her eyes. "I, uh, borrowed them." Clearing her throat, she got back into character. "Now, you're gonna listen to my mixtape." She brandished a CD.

Hitch shook his head. "No, no way! I'm not listening to it!"

"It's hot, yo." Pipp insisted. "Straight fire. You listen to this, winter becomes summer, pony."

"No! Never!" Hitch said defiantly.

"Alright; didn't wanna have to do this, homeboy." Pipp replied with menace before she pulled out her true weapon.

Hitch's scream echoed through the lighthouse, sending chills down Sunny's back. She quietly moved out from under her bed. "Zipp? You there?" She quietly called out.

"Yeah, I'm over here." Zipp called from under her desk. "Sounds like Pipp got to Hitch."

"Yeah, I heard it." Sunny cautiously stepped out into the open, now cloaked only by the darkness. "Listen, if we're quiet, I think we can get to the beacon floor, but I have to unlock the elevator."

"But the power's still out?"

"Don't worry, it has a sperate power generator. My dad set it up like that in case the power went out... like now."

"Well, what are you waiting for? Hurry!" Zipp urged, coming out from her spot as well.

Just as Sunny got to the elevator control switch, she was halted by the sound of singing coming from the other side of the bedroom door.

"Ice, Ice, pony. All of the Pippsqueaks are jumpin', and all of the mommas are crumpin'."

Zipp quickly returned to her hiding spot and motioned for Sunny to do the same only to realize Sunny probably couldn't see her gestures in the dark.

Regardless, Sunny slid back under her bed just as the door opened. She could just make out the form of Pipp walking into the room. "I know my ponies are in here." She called out. "You two ghostin'?"

Sunny watched as Pipp's dark figure went to the center of the room and placed down something. "That's cool. I got places to be anyway. I'll just leave you with a lil' sample of the craft though." She then pressed a button on the object that Sunny realized was a boombox. The room was filled with the results of Pipp's mixtape and Sunny found to her horror that Zipp was not exaggerating. Hood-style rap was very much not Pipp's expertise; the clunky rhythm, the cringey lyrics, the messy rhymes; it was too much for Sunny to take.

"I can't take it anymore!" Sunny yelled as she left her hiding place to turn the dreadful music off.

"No, Sunny!" Zipp whisper yelled. "It's a trap!"

Indeed, as soon as Sunny turned the boombox off, Pipp dropped from the ceiling, startling Sunny onto her back. "That was a lil' sample from my first draft." Lightning struck as she pulled out a CD. "But this is the real gas, homie."

Sunny backed away on the floor. "Why are you using CDs anyway? Why don't you just put it online like the rest of your songs?"

"It's for authenticity." Pipp grumbled before getting back into character. "Support the struggle, homie."

"What struggle?" Sunny asked incredulously as she backed into a wall. "You're a princess, a world-famous streamer, and a national hero; you're the last pony struggling!"

"Look, are you gonna listen to my mixtape or not?" Pipp asked in an annoyed tone.

Sunny bit her lip and noticed Zipp's figure behind Pipp. "Run, Zipp, run!" She called.

Pipp turned around and Zipp obeyed and ran out the door. She returned her look to Sunny, who was baring a guilty smile that Pipp couldn't possibly see through her sunglasses. "Bad choice, my pony."

Zipp glided off the balcony and made for the door only to be woefully reminded of it's blocked state. She gasped when she heard Sunny's scream. No time to move it. Gotta hide. In her panicked state and fumbling in the dark, Zipp went for the first door she could find. She went inside, quietly shutting it behind her. Taking a deep breathe, she did her best to take in her dark surroundings. Finding herself going down a staircase, she realized she was in the storage closet. No big deal, she decided. She could wait here. As long as she was quiet and stayed in the dark corners of the room, she could outlast Pipp.

To her surprise, the room was then filled with light. Temporarily blinded by the sudden light, she realized that the power must've come back on. Then something dawned on her made her freeze in place. The closet light shouldn't have been on when the power went out and Zipp was certain she hadn't touched the switch when she came in.

Hearing something land softly behind her, Zipp slowly turned around to find her sister standing there, CD in hoof. "It's Pippy Pipps."

Zipp stumbled back. "H-Hey, girl."

"You been hidin' from me, sister?"

"What, no." Zipp lied.

"Yeah, that's all good; that's cool."

Finding herself cornered, Zipp had to think fast. "Hey, I was listening to your mixtape earlier. You killed it, sis!" Thinking fast did not mean thinking thoroughly.

"Oh, really?" Pipp questioned skeptically.

"Yeah, it was, uh, fire! Yeah, you did great." Zipp paused when Pipp lowered her sunglasses to look Zipp in the eyes. "Wait, aren't those my sunglasses?"

Pipp redirected the question with one of her own. "Name track 5."

Zipp gulped and racked her brain for a guess. "Umm..."

Pipp nodded. "No hard feelings, yo. But you leave me no choice."

Zipp was backed against the wall as her sister readied her secret weapon. Zipp stared wide eyed as Pipp took off her sunglasses... and gave her the biggest, most pitiful-looking puppy-dog eyes she could muster. The same weapon that had forced Hitch and Sunny to give in to her request. And Zipp knew she wouldn't be able to resist either.

Zipp screamed.

"Pippsqueaks are goin' cra-zay, people calllin' me bay-bay, rain pourin' and thunder goin' bang-bang-"

"Thunder goes 'boom', Pipp." Zipp input with annoyance.

The now light-filled living room had now become Pipp's rap studio for the night. Zipp, Sunny, and Hitch acted as Pipp's audience and did their best to suffer through Pipp's rapper experiment. Meanwhile, Izzy, who had actually enjoyed Pipp's rapping and had spent the debacle listening to the mixtape under the glass roof of the beacon that Pipp had brought her to, recorded Pipp so the Pegasus could review herself later.

Pipp let out a groan. "Am I at least getting better?"

Hitch was the one to awkwardly offer an answer. "You're, umm, not getting worse?"

With a sigh, Pipp decided to take a break. "I thought the method acting would help." She grumbled.

Zipp patted her sister on the back. "Maybe the whole 'gangster rapper' thing just doesn't fit you. You tried; but it just isn't working."

Pipp sighed again and took off her cap. "Maybe you're right."

Zipp smirked and snatched her sunglasses of her sister, putting them on herself. "Besides, you look ridiculous."

Pipp pouted and pushed Zipp playfully. "I pulled it off better than you could."

While the sisters continued their playful banter, Hitch groaned. "So, all of that was for nothing."

Sunny smirked and raised an eyebrow. "Would you rather spend the rest of the week dealing with 'Pipp Shady'?"

"...No."