Cheerilee and Mayor Mare Hit Las Pegasus

by Yukito

Rating: everyone
Tags: Cheerilee, Random, My Little Pony: Friendship is Magic, Comedy, Mayor Mare, Adventure
Length: 3186

With Cheerilee's job nabbed by Twilight, Mayor Mare decides to take her friend to Pegasus to unwind. Things go wrong, of course.

With Twilight's new school offering so much more than Cheerilee's smaller one, and staffed by none other than Princess Twilight herself, more and more parents are making the switch to the new School of Friendship, leaving Cheerilee a proverbial shepherd with no flock.

To cheer her friend up, Mayor Mare takes Cheerilee to Viva Las Pegasus! Naturally, because the story would be boring otherwise, things go awry.

Published 2018-04-02 21:10:07 UTC
Last updated 2018-04-02 21:10:07 UTC

Cheerilee and Mayor Mare Hit Las Pegasus

It happened gradually, but surely. It started with just two students leaving her class, and then three more followed the next day. And then four, and then half her students were gone.

Ever since Twilight Sparkle's new School of Friendship was opened, parents had been attracted to the idea of a school run by Princess Twilight herself. A school which taught more than Cheerilee was qualified to and had state-of-the-art equipment. A school that Cheerilee simply could not compete with.

With no students left, Cheerilee had no means of keeping her school open. Her days as a teacher were… over.

"Of course, I applied to teach there, what with my years of experience and dedication to Equestria's youth!" Cheerilee downed another drink, sighing as she slammed the glass onto the counter. "'Oh, I'm sorry, Cheerilee! We've actually got plenty of teachers and can't really take another right now! But maybe one of us could take an assistant…' BAH! Assistant?! What is that?! I didn't bust my flank for half my life to be demoted to ASSISTANT!"

"Preach it to the choir," Mayor Mare said, twirling her empty glass on the counter as she glared into the space ahead of her. "Ever since Twilight became a princess, suddenly she's in charge of Ponyville! No, never mind that I was voted into office, or that I studied politics at Canterlot's finest institute. The librarian has wings now, so let's just let her lead us all!"

"At least you still get your fancy office and your nice big paycheque," Cheerilee said. "Without any students, I don't get paid, and the EEA are selling the land that the schoolhouse is currently on." Cheerilee downed another drink and slammed the glass down. "ARGH! They took my job!"

"They took her job?!"

"Dey took 'er jerb!"

"DERK 'ER JERRR!"

Cheerilee turned around and glared at the three stallions sitting behind her. "You don't need to rub it in!"

"So what now?" Mayor Mare asked. "If you want to burn down the new school, I could come up with some way to distract the townsponies…"

"No, no… Crystal doesn't burn easy." Cheerilee brought another drink to her lips, but stopped. She sighed as she gently put the glass down. "I don't know… I think… I think it may be best if I move on… I'm sure there's a school out there, somewhere, that's in need of a teacher."

"So, your mind's made up?" Cheerilee nodded. "Well… let me at least see you off with a blast." Mayor Mare finished her drink and turned to her friend. "Go home, get your money, and meet me at the train station. We're hitting Las Pegasus!"

"A straight! The mare from Ponyville wins again!"

Cheerilee squealed with excitement as the chips were pushed over to her side of the table. "Yes! I'm on a roll!"

"Wow, you're good at this!" Mayor Mare cheered. "Hey, another round of drinks on us!"

The crowd around them cheered, and Cheerilee dealt herself in for another hoof. Two of the contestants at the table left, leaving only one opponent, but another soon entered. He was a young stallion, possibly too young to even be in the casino, but he was dealt-in all the same.

"You're doin' pretty good there, Missy," the stallion said, grinning as he threw some bits into the pot. The other challenger folded, but Cheerilee called the bet. "Maybe a little too good." Three cards were placed into the river, and the stallion grinned wider. "Wonder how long your luck'll last, though?"

"Hun, lemme tell you somethin'," Cheerilee started. "I've spent the finer years of my life with children who will tell any stories they can to dodge responsibility and get out of trouble. I know a lying face when I see one, and frankly, yours is embarrassing."

"That so? Well, I'm gonna make this interestin', then."

The stallion placed a golden watch, covered in jewels, onto the table. "That… looks expensive," Cheerilee said.

"About five thousand bits," the stallion said. "Guy who made it only made fifty of these, and eight belong to the royal family. Ten are missin', and I have one of 'em right here."

Cheerilee's ears drooped. "I can't match that…"

"Hey, you sure you can beat him?" Mayor Mare asked.

"Oh yes, he's got nothing. But I can't meet the bet."

"You can now." Mayor Mare placed a small crystal onto the table. "This here crystal is a fragment of Princess Twilight's castle!" Gasps and murmurs erupted from around the table. "It came loose when the castle formed and I decided to keep it as a down-payment on the new building. She wouldn't notice anyway, and you know what they say: what happens in Pegasus, stays in Pegasus."

"Still, are you sure it's okay to bet with this?" Cheerilee asked.

"Just think of it as Twilight's compensation for taking your job."

"She took her job?!"

Cheerilee turned to the stallion in the crowd with a glare. "YES!"

"Oh, okay. I was just checkin'."

Turning back to her opponent, Cheerilee said, "Okay, I'll bet with this. Wanna get it appraised, first?"

"Nah, I trust ya," the stallion replied, and the game continued. The crowd's muttering grew, and Mayor Mare noticed how many ponies were beginning to leave… No, not leave. They stepped further away from the table.

"Hey, Miss?" one stallion spoke up, but he stopped quickly. Mayor Mare noticed that he looked frightened.

"Miss Cheerilee has a three-of-a-kind," the dealer said, and then turned to the stallion. "… And Master Jacques has a…"

"Go on," the stallion said, still grinning over at Cheerilee.

"… A-A pair of threes." A silence fell, save for the erratic and excited cheering coming from the two mares.

"Oi, now," Jacques said, standing up and scooping up the pot. "That's not good, little lady. Cheating me like that."

Cheerilee and Mayor Mare suddenly stopped. "Cheating?!" Cheerilee shouted, standing up and slamming her hooves onto the table. "Now look here! How could I possibly have cheated with all of these witnesses around?!"

"Well, witnesses?" Jacques asked.

Nobody answered for a while, but eventually one stallion spoke up. "I was… too far away to see."

"I don't really know much about cards, so it's possible," one mare said.

"That's very naughty," Jacques said as he strapped his watch back on and pocketed the small crystal. "But hey, I had a good game, so I'll cut you a break… if you give me fifty percent of your remaining chips and leave right away."

"This is outrageous!" Cheerilee shouted. "Who do you think you are, bullying somepony like that?! Have you no respect?! I demand to speak to this casino's manager!"

"Sure, I'll take ya to him," Jacques said. "My uncle would just love to hear and you conned me, and then called me a liar!"

Suddenly, Cheerilee paled. "O-On second thought, I have a train to catch…"

As the two mares turned to leave, they found two large, very bulky stallions blocking their paths. Mayor Mare gulped. "Oh, crud…"

"Well, some vacation this is turning out to be," Cheerilee grumbled as she followed Jacques through the dark hallways at the back of the casino. They reached an elevator and all went in.

"I'm sorry, I didn't mean for things to go this way," Mayor Mare said. "But, hey, it was fun while it lasted, right? C'mon, let's enjoy our last moments together!"

"Or, we could think of a way not to be killed?" Cheerilee suggested.

"Right, of course, just… trying to lighten the mood…"

"Hey, we're here," Jacques said as the elevator's door opened. He led the mares into a large room, decorated with golden sculptures of various mythological creatures and ponies of legend. To the side was a hot tub where several mares were bathing, and at the farthest end of the room was a stallion with black, slicked-back hair.

He wasn't the large, hulking figure that the mares had feared, but he seemed intimidating enough even without that.

"Hey boss, these're the mares!" Jacques said as they drew closer, and then stopped some distance away. "The mayor from Ponyville and the… I dunno, her secretary, I guess?"

Cheerilee frowned. "How rude! I am a teacher, young man, and I will-"

"Hah! Teacher, eh? Last teacher I had quit only two weeks in."

"Thank you, Jacques," the boss said as he approached the three ponies. "You may go now. Oh, after giving me the prize you won from your little game."

Jacque's ears drooped. "P-Prize? What prize?" The boss clapped his hooves, and suddenly ponies appeared from behind the sculptures, cracking their necks and their hooves as they focussed on Jacques. "O-Oh! That prize! Yeah, sure! I was uh, I was gonna give it to ya after I got it appraised, I swear!"

"Thank you, but I can handle that myself."

"O'course, Mister- Doctor Caballeron. Uh, here." Jacques handed the crystal to the stallion – Caballeron – and then made his hasty retreat from the room.

"Isn't Caballeron a villain in Daring Do?" Cheerilee whispered to Mayor Mare.

"Officially, yes," Mayor Mare whispered back, "But the truth is that he's a real pony. A crime lord who's hunted by Her Majesty's Secret Service."

"Great," Cheerilee deadpanned. "First I lose my job, and now I'm taken prisoner by a mob boss from a book."

"Am I boring you, perhaps?" Caballeron asked.

"Oh, no! Not at all!" Mayor Mare asked. "We were just, uh, admiring your lovely decorations!"

"Ah, yes. I suppose, coming from a rustic little village such as yours, this humble little workspace of mine would seem impressive."

"So, uh, what did you want with us?" Cheerilee asked.

"Well, I hear that you cheated my dear little nephew in a good-spirited game of Poker," Caballeron said. "We can't have that now, can we?"

"But we didn't-"

"Then you are calling my nephew a liar?" Caballeron asked. "Because if so, I do ever-so-hope you have proof. For your sakes."

The mares fell silent. So silent that their heartbeats echoed through their ears.

"W-We'll let you keep all the money we won," Mayor Mare said.

"Yes, you will," Caballeron said. "But dishonesty is not so easily forgiven, capisce? I will have you pay for your crimes by working in my casino for, oh, twelve months?"

"Twelve- I can't- I have a town to run-"

"Of course, I am not without mercy."

"Could've fooled me," Cheerilee muttered.

"I will allow you to pay off your crimes in another way."

Mayor Mare gulped. "W-What other way?"

"Welp, here we are," Cheerilee said, gazing at the cottage dead ahead of her with Mayor Mare by her side. "First we get called cheaters, then nopony defends us, then we're taken up to the big boss who turns out to be a villain from a popular fictional series, and now here we are, outside of Daring Do's cottage with poison that we're meant to use to kill her."

"Usually my vacations turn out bad," Mayor Mare admitted, "But like, the weather pegasi mess up bad, or a monster attacks Ponyville and I'm called back early bad."

"You ever killed a pony before?"

"Not in reality. It's bad for public image."

Cheerilee nodded. "Same. I think they'd revoke my teaching licence."

"But, Daring Do is believed to be fictional, so maybe it's okay?"

"But then again, she's a hero to foals everywhere, so you'd be crushing their dreams," Cheerilee added.

"Hey, you two can discuss your moral dilemma after you've finished the job," Jacques said, prodding Cheerilee's flank with the blunt end of a spear. "Go on, get to it!"

Cheerilee turned back with a glare, but then noticed something interesting. "Say, he's only got two ponies with him."

Mayor Mare also turned around, and noticed the same thing. "… You're right."

The two mares exchanged looks, and then together, they smiled. "That was careless, huh?"

"They underestimated us. We defend Ponyville from monsters every week!"

"Hey, we're not payin' you by the hour here!" Jacques shouted.

"Uh, right, just one question about this poison," Cheerilee said as she approached the stallion. "Haven't done this before so I wanna make sure I get it right." Suddenly, she lunged forwards, clocking the stallion's face with her hoof.

The two ponies escorting Jacques charged towards her, but were intercepted by Mayor Mare. "Move it, Granny!"

Mayor Mare felt a vein pop in her head. "'Granny', you say? I'll have you know I dye my hair this way!" Mayor Mare grabbed one stallion by the foreleg, lifted him into the air, and then used him as a bat against the other, sending the two flying into a nearby tree.

"Why do you dye your hair grey?" Cheerilee asked as she unloaded her saddlebags on Jacques.

"Ponies believe you more when they think you're older. They think it makes you wiser."

"Fair enough. So, what now? Do you think Caballeron will still come after us?"

"Well, we didn't exactly kill Daring Do," Mayor Mare noted.

"Yeah, thanks for that."

"I don't exactly want to kill anypony," Cheerilee said.

"Yeah, please don't."

"But on the other hoof-"

"Let's not look on the other hoof."

The two mares blinked, and then looked up to where the third voice was coming from. Above them, a tan-coloured pegasus swooped down. Cheerilee could barely believe her eyes. It was really her! It was really…

"A. K. Yearling!" Cheerilee cried, squealing with excitement and resisting the urge to glomp one of her favourite authors of all time.

"They attacked us!" Mayor Mare shouted, pointing to the downed stallions around them. "This was self-defence! I was well within my rights to-"

"Don't worry! I get the gist," Yearling said, picking up a small bottle by Jacques' side. "Don't worry about it, I get this all the time. Comes with having your arch-nemesis know exactly where you live. I really oughta look into that."

"'Arch-nemesis'?" Cheerilee asked. "Wait, I'm seeing a resemblance here… Don't tell me that you're… Daring Do's sister?!"

Yearling's eyes shifted side-to-side. "Er, yeah. Sure am!" She cleared her throat. "Now, don't you guys worry! I'll handle- er, I mean, I'll ask my sister to handle Caballeron! He'll think you guys tried but failed to poison me and won't even care enough to track you down. Trust me, happens all the time. Though this is the first time somepony actually fought back and- whoa, you slugged 'im good!"

Cheerilee blushed and chuckled quietly. "Well, you know… I always have to be ready to protect my students…"

"So, we're in the clear?" Mayor Mare asked.

"Oh yeah. I'll hand Jacques and his goons over to the Royal Guard and then foil Caballeron's next scheme. You guys just follow the path behind my house to find the nearest village."

"Thank you, Miss Yearling."

Cheerilee nodded her head. "And, um, by any chance-"

Yearling handed Cheerilee a piece of paper with her name on it. "Here ya go."

"EEEEEEEEE!!!!!" Cheerilee hugged the paper close to her chest and hopped happily in-place. She calmed down and noticed that Mayor Mare was grinning her way. "A-hem! Um, thank you, Miss Yearling. I'll uh, keep it safe."

"Always a pleasure," Yearling said, waving goodbye to the two mares as they followed the path through the forest. "… Wow, she was louder than Rainbow Dash."

"Well, that may not have gone entirely as planned," Mayor Mare admitted as the two departed the train, "But still, it felt good to unwind, did it not?"

Cheerilee couldn't help but laugh. "Yes, I have to admit that I enjoyed letting myself loose for the first time in a while. Still, we're back now, which means we're back to the reality that I'm… going to have to leave soon…"

"Oh, you're back!" The mares were stopped by Bon Bon, owner of a local confectionary store, as she approached them in the street. "Where have you been? Ponies have been looking for you!"

"We went to Las Pegasus," Cheerilee said. "Mayor Mare took me, as a sort of farewell party."

"'Farewell party'? You're leaving?!"

"What?" Berry Punch asked, approaching the three ponies together with several concerned-looking mares and stallions. "You're leaving, Cheerilee? Why?"

Cheerilee sighed. "I don't have a job here anymore. Not since Twilight Sparkle and her friends opened up their school."

"You didn't know?" Caramel asked.

"Know… what?"

"The school's closed!" Berry Punch answered.

Cheerilee's eyes widened. "What? I mean, are you sure?"

"We sure are," Derpy Hooves said. "Princess Twilight and her friends had to keep going to solves friendship problems all over Equestria, so they had to shut down."

"It wasn't just that," Berry Punch said.

"Twilight was killed by a ravage monster and now you all need somepony new to lead you through these dark times?" Mayor Mare asked.

"Er, not quite…"

Mayor Mare clicked her tongue. "Well, maybe next time," she muttered.

"Rainbow Dash was called away for a month-long retreat with the Wonderbolts, Applejack and Fluttershy couldn't balance teaching with their other duties, and frankly, I think Rarity's mane was starting to turn grey from all the deadlines she was missing."

"Guess we should've figured this'd happen," Twilight said as she approached the crowd, a nervous grin spread across her features. "We had so many duties already, and I just sort of underestimated how much hard work it would be."

"Not to mention you ran out of things to teach two days in," Bon Bon said, "And then your friends had nothing to teach that was actually on any school curriculum."

"I heard Applejack couldn't even multiply or divide," Lyra whispered to Mayor Mare and Cheerilee.

"Well, whatever the case, we're glad to have you back, Cheerilee," Bon Bon said.

"The foals enjoyed the time off," Berry Punch said, chuckling with some of the other parents around them, "But I think it's about time they get back to classes."

"Of course," Cheerilee said, "And I think we've all learned a little something today, haven't we?"

"We sure have," Twilight said. "Passion is important, but so is hard work and dedication. Teaching isn't just something you can jump into, and neither is running a school or a business – and it's certainly not something you should do without devoting yourself fully to it."

"Well, yes, that. But also…" Cheerilee wrapped her foreleg around Twilight, pulled her closer, and whispered into her ear, "The schoolyard is my turf. Stick to the library where you belong, or I will do worse than put your in detention." Cheerilee pulled back with a warm, cheery smile. "Capisce?"

"C-Capisce…"

And so, life in Ponyville returned to normal. Well, as normal as living in a town that was frequently ravaged by monsters from the local out-of-control magical forest could be, at least. Cheerilee resumed teaching her classes, and was even willing to accept the new foreign students who had originally joined Twilight's school. And they all lived happily ever after until the yaks declared war on the hippogriffs, but that's a story for another time.

The end.