Pipsqueak Starts a Gang

by DwarvishPony

Rating: everyone
Tags: My Little Pony: Friendship is Magic, Snails, Pipsqueak, Cheerilee, Scootaloo, Random, Slice of Life, Snips
Length: 2523

After winning the class election, Pipsqueak gains a taste for ponies looking up to him. Things spiral from there.

Pipsqueak's won the class election. It's an amazing feeling, being in charge. Ponies listen to Pip more now. But why should he stop there? If other fillies and colts will listen to him, why can't the grown ups too? So Pip finds a way to get more ponies to listen to him. Aided by a group of friends, Pip sets off across town, much to the chagrin of Ponyville's residents.

Published 2016-03-19 21:40:01 UTC
Last updated 2016-03-19 21:40:01 UTC

Started from the Bottom (of a fantastic see-saw!)

Pipsqueak loved being class president. Thanks in large part to the Cutie Mark Crusaders, Pipsqueak Q. Hoppentrot had gone from frequent bullying victim to probably the most popular colt in school. If he had something to say, his classmates would stop and listen, rather than walk away. If he asked somepony to do something, they actually did it! If only the grown-ups around Ponyville would listen to the colt though. He had some really good ideas to help the town. Honest!

Like the time he thought it would be a good idea to make the fountain in the town square have cider instead of water. Then, when somepony drank from it (even though it was a faux pas, according to Miss Rarity) they would get a tasty, refreshing drink of cider. Or when Pip had suggested to Mayor Mare that Ponyville should build a fence around it's borders to keep out those darn monsters like Tirek. Sweet Apple Acres had a fence, and no monsters ever attacked it. Mayor Mare had simply said it "sent the wrong message to the rest of Equestria", whatever that meant.

So while Pipsqueak Q. Hoppentrot could keep his classmates happy with his great ideas, the rest of Ponyville was oblivious to them. It was a shame, really. Even ponies who were prone to listening to ponies younger than them seemed to brush of the ideas Pip offered to them. Twilight Sparkle had even laughed when he had told her that Twilight should have her own holiday based on lists.

"I don't need a holiday.Besides, making lists isn't the sort of thing most ponies would celebrate. Not even Pinkie Pie would be that weird." Was what Princess Sparkle had said.

It was this constant deflection and ignoring of ideas that lead Pipsqueak to a very frustrating thinking session on the see-saw after school. The see-saw had always been Pip's thinking spot. Not because he could move the darn thing by himself. Just because it was a comfortable seat outside. Especially the new see-saw. It had nice, padded butt cushions for sitting.

Pip sat on his favorite spot, staring upwards at the sky. A passerby may have thought he was watching a pegasus fly above him, or that he was waiting for rain. In truth, Pip wasn't sure why he was staring upwards. There were no clouds to watch, and certainly no pegasi flying above the school this late in the afternoon (though there was one in class that he wouldn't mind watching fly all day. That, however, is a story for another day.). Even Miss Cheerilee had gone home for the evening.

Pip simply sat and pondered. Sure, ideas floated through his head now and again, but nothing that wouldn't be shot down by grownups. What would Diamond Tiara do? Ponies listened to her. She even got her dad to donate the money for the new playground. Sure it was called the Filthy Rich Playground now, but it was still a new playground. And the see-saw was fantastic!

Movement near the front of the schoolhouse caught Pipsqueak's attention. It wasn't a sudden movement or anything. Just movement. Turns out it was Scootaloo, ~~the really cute-~~ one of the Cutie Mark Crusaders who had helped him win the class election. He waved an eager hoof at Scootaloo, but not too eager.

"Scootaloo! Hey!" Pip called with a goofy grin on his face. "What are you doing here?" Pipsqueak was one of those ponies you could always pick out in a crowd. He had an accent that screamed 'not-from-Ponyville'. Trottingham, if you were curious.

"Oh. Hey Pipsqueak. What are you doing here?" Scootaloo trotted over and stood next to the see-saw (which was really good. Did I mention that?).

"Oh, I was just thinking about stuff." Pip replied glumly. "What about you?"

"I... kinda forgot to turn in the homework from yesterday. I totally did the homework, I just left it at home next to Appleblooms homew- I mean on my desk at home. I was trying to turn it in, but Miss Cheerilee's not here anymore." Scootaloo replied smoothly. "What kind of stuff are you thinking about. Anything I can help with?" The orange pegasus fluttered her wings rapidly, lifting her just high enough to pull the see-saw down to her level and sit on the other end.

"Well... I just feel like nopony listens to me." Pip complained. "Like, I have all these good ideas. And nopony seems to care." The colt huffed with his last comment.

"What are you talking about? Everypony in school listens to the stuff you say." Scootaloo raised a confused eyebrow and kicked off from the ground, raising her end of the see-saw. "I'm pretty sure they have to, you being class president and all."

"Not the class. Everypony else. Ponyville. Mayor Mare! Princess Twilight!" Pip kicked off on his end, setting the see-saw into a rise-and-fall pattern. "How do the Cutie Mark Crusaders get ponies like Princess Twilight Sparkle to listen to the stuff they say?"

"I dunno. I mean, Applejack is Apple Bloom's sister. That probably helps. As for the rest of Applejack's friends... I dunno. Maybe because there's three of us saying the same thing? Rarity seems like she says yes to sleepovers a lot more often when me and Apple Bloom are with Sweetie Belle when she's asking."

It was as if Princess Luna (Pip's favoritest princess) had swooped down from the sky to answer Pipsqueak's problems. The answer was so simple! Pipsqueak just needed other ponies with him whenever he pitched his ideas! He wanted to hug Scootaloo, and even got off the see-saw to do so. But then his insides got all squibbly and he turned red. He stopped shy of the pegasus instead.

"That's a great idea Scootaloo!" Pipsqueak said with a voice that was a few notes higher than usual. "Thank you for helping me! You're the best!"

Off Pip ran, leaving Scootaloo somewhat confused about how she had helped. But she shrugged it off. 'Hanging out with Rainbow Dash must have made me a natural at helping others. I guess Dash's awesomeness is starting to rub off on me.' Scootaloo thought to herself as she trotted away from the playground.

~~~

Pipsqueak was looking for some of his closer friends from class. Preferably Rumble and Featherweight. They always thought his ideas were good. Maybe Twist? Maybe. She was always acting a little funny around Rumble. Like couldn't-ever-say-words funny. So she was a definite maybe.

"Where ya headed, Pipsqueak?" A voice called out as Pip ran through the streets.

"Uh, yeah! Where ya goin'?" Another voice called from roughly the same location.

The voices belong to Snips and Snails, respectively. The two were best friends from Pip's class. Diamond Tiara had once said that they were better than best friends, but Pip didn't really get it. Because best friends wouldn't be called best friends if there was something better than best. Unless bestest friends were a thing like Pinkie Pie said. But Pinkie Pie always said weird stuff, so she was hardly a credible source to cite.

"I was goin' to find Rumble and Featherweight and tell them a great idea I had!" Pip said when he had caught his breath a little bit.

"What kind of idea?" Snips asked curiously.

"It's a surprise, but if it works I'll make sure to tell everypony!" Pip explained excitedly before dashing off again. Snips and Snails took one look at each other before running after the diminutive colt.

~~~

Pipsqueak found Rumble and Featherweight playing hoofball in an open area of grass near the town hall. And by playing hoofball, it was more Rumble charging through Featherweight multiple times while he held a hoofball.

"Guys! I just had the greatest idea ever!" Pip ran up to the pegasi with Snips and Snails close behind.

"Yeah? What's that?" Rumble asked, holding the hoofball under a wing.

"I know how to get grown ups to listen to my ideas! Scootaloo told me how." Pip exclaimed happily. "Just follow me, and it should work. I want to try out my new idea now!" Pip could hardly contain his excitement. He darted off again without waiting for a response from his friends, who followed behind him eagerly.

~~~

Bonbon's Confections Galore was a lovely little shop in the heart of Ponyville. Bonbon had saved up a small fortune in order to buy the place. It had a perfect location, and during business hours always had customers looking to buy. When five colts entered the tastefully decorated shop, Bonbon welcomed the group with a warm smile.

"Welcome. What can I get for you today?" Bonbon asked happily.

Pip stepped forward. "Um... I was thinking..." He scuffed a hoof on the ground nervously.

"Yes?" Bonbon gave another warm smile, expecting Pip to place an order for himself and his friends.

"Um," Pip took a deep breath and steeled himself. "We think you should start giving away free samples."

"Well I would, but that's just not possible at the moment. I don't have enough chocolate to-"

"Pleeease?" Pip begged, desperate for his plan to work. It worked for the Cutie Mark Crusaders, after all.

"Look, I really like you all. Really, I do. It breaks my heart to say this, but-" Bonbon couldn't finish her sentence. Pip had resorted to flashing the most pathetic, heart-broken look he could. "I- Fine. Just this once though."

Pipsqueak could have gone through the roof, he was so happy. His friends stared in awe. They'd all tried getting samples from Bonbon's shop before, but none of them had ever been successful. Ever! With sweets in hoof, the group quickly thanked Bonbon and darted outside to enjoy the treats.

"Aww. That was sweet, Bonbon." A turquoise unicorn gushed after the colts had left. "Just what I'd expect from my best friend."

~~~

"That was awesome, Pip!" Rumble hoofbumped his friend as he congratulated him. "We should totally do more stuff like that!"

"Yeah! It was cool the way you convinced Bonbon to give us free candy." Snips chimed in.

"Yeah, it was cool." Snails agreed.

"What should we do now, Pip?" Featherweight asked, looking to Pipsqueak for suggestions. Everypony else turned to Pip as well.

"Um..." Pipsqueak could have really used the see-saw for thinking at that moment. A trickle of sweat slipped down his forehead. "We should..." 'Think, Pip, think!' "We should go test all the sofas at Davenport's shop!" It was the best thing Pipsqueak could think of on the fly. His friends looked at each other with confused expressions.

"Yeah!" Snips cried out, breaking into a grin. Soon everypony was smiling and agreeing with the idea. Pip silently thanked Princess Luna and lead his friends over to Quills and Sofas.

~~~

Quills and Sofas was a lovely little shop located near the Golden Oaks Library Memorial, and happened to be Princess Twilight's favorite shop in all of Ponyville. The owner, Davenport, was a cheerful fellow with a disposition that never seemed dampened by the fact that ponies shopping for quills didn't want sofas and vice-versa. He greeted everypony who passed by his shop, even if they weren't looking to shop there, and had garnered a reputation as one of the friendliest shopkeepers in town.

So when five colts ran up to his shop, Davenport gave his trademark smile and greeting. He'd expected them to move on. To go play somewhere. Instead, all five of them entered Quills and Sofas and began sitting and climbing on the sofas!

"Now wait a minute, now." Davenport said, his voice lost in the excitement. "I- please don't do that!"

The colts paid no attention to the distraught stallion.

"Please don't jump on- No that's not- Don't climb that!" Davenport could barely hear himself over the noise the colts made. After what seemed like an eternity of trying to gently dissuade them, Davenport sat down on one of the few fainting couches in stock (Rarity replaced hers on a near monthly basis) and buried his face in his hooves until Hurricane Coltplay passed. It took about a half-hour for the colts to get bored and leave, laughing and chasing each other.

~~~

And so the day continued well into the dusk hours. The colts ran all over Ponyville, mischief following in their wake. They played hide-and-seek at Sweet Apple Acres, tried on all sorts of costumes at the costume shop, pranked each other in the joke shop, and even did Princess Twilight impersonations with a crate at the soap stall in the market. Each shop they visited and each venue played in left disgruntled mares and stallions behind.

By the time dusk had rolled around, Pipsqueak and his friends were playing in the playground back at the school. Pipsqueak and Featherweight were on the see-saw, Rumble was on the jungle gym, and Snips and Snails were on the swing set. Everypony was rather pleased with the fun time they'd had today and chatted excitedly about their adventures. They'd even started talking about doing it again tomorrow when Miss Cheerilee walked up. She didn't look pleased with her students.

"I hear you've been having quite the adventure around town today." Miss Cheerilee mentioned. A tone in her voice made the colts stop what they were doing, leaving Pipsqueak in the air as the see-saw stopped.

"Yeah! It was super fun!" Snips answered, oblivious to the disappointment plastered on Miss Cheerilee's face.

"And what about the ponies at the places you visited? Did they have fun?" Miss Cheerilee pointed out.

"Uh..." Snips thought hard about his answer. "Yes?"

Miss Cheerilee sighed. "No. They did not. I've been getting complaints all afternoon about your... games. Harassing Davenport? Begging for free sweets from Bonbon? These are not the things I try to teach you, my little ponies. I'm very disappointed."

Everypony flattened their ears and stared down at their hooves at the reprimand before replying with a "We're sorry" in unison.

"I'm not the one you should be apologizing to, am I?" Miss Cheerilee raised an eyebrow to punctuate the question. "I want all of you to go back to all the places you visited and apologize to everypony you've upset."

"Okay..." Another group response.

"And after that, I want you all to see me after school tomorrow for detention." Everypony let out a groan.

"But Pipsqueak's the one who told us to do it." Snips pointed out, becoming the Bridledict Arnold of the group.

"I don't want any excuses. You're all equally to blame here." Miss Cheerilee rebutted.

Off everypony shuffled, dejected looks on their faces. The went to every shop and location they visited, offering sincere apologies to everypony they'd seen over the course of the afternoon. It was awful. Everypony had mad looks on their faces. Then the next day they served their detention. Detention sucked.

Author's Note

The results of mixing insomnia and rewatching Crusaders of the Lost Mark. Saw the frame I used for the cover image in the "Vote Song" and had to create this.

I regret nothing.