My Little Payday

by Pippington Britishhooves

Rating: teen
Tags: Cutie Mark Crusaders, Pipsqueak, Dinky Hooves, Adventure, Crossover, My Little Pony: Friendship is Magic, Featherweight, Other
Length: 4922

A group of innocent, entirely legal young adult ponies are completely innocent, right? All this group needs is their payday.

A side story to Generations.

One day, Pipsqueak told a story to his friends- a story about a gang of criminal masterminds who topped all others in Equestria, who pulled off daring raids and captured vast amounts of money, accruing wealth and sometimes redistributing it to the fair citizens of Equestria. They were known across the land, feared and admired in equal measure, their identities hidden by their infamous masks. The question is not their identity, but how far this organisation descends.

This is a rough approximation of Pipsqueak's story.

(The cover picture is not meant to represent which characters appear in the story, only the general appearance of the actual characters in the story.)

Published 2015-12-02 04:10:01 UTC
Last updated 2015-12-02 04:10:01 UTC

The Proposition

The hit looked to be bad from the start, but they coped well to begin with. The jewelry store had eight customers in it, plus the cashier, which was eight more than they were expecting. It was a small town shop, and it never had that many ponies in it at any one time. Nonetheless, the group had masked up and slipped inside. It was the usual routine; Rooster up at the front, bellowing at the customers to get on the floor, Snapshot sweeping around to check for alarms or cameras, Manehatten moving around the side to size up the loot, and Sparks drawing up at the rear, eyes sweeping for any emerging threats from their hostages. Within minutes, the ponies in the store had been tied up and the place determined to have no security. A slight blip in the number of occupants, but that had been dealt with accordingly, and so it was time to move on.

"Nopony here needs to worry," Sparks announced, her calm, firm voice contrasting against the smash of glass as the others set about breaking into the display cases and pulling the jewelry into duffle bags. "We're only here for the jewelry, and nothing else. None of you are going to get hurt, we assure you of that. Just stay calm, stay quiet, and we'll be done soon. I apologise personally for any inconvenience here." The talk always seemed to keep the hostages occupied enough to let the group fill their bags with the loot and leave, and just as she expected, nopony bothered moving. None of them tried to resist or argue or reason with her. Manehatten was zipping up a third bag and lifting it onto her back with relative ease to join the other two, while Rooster was sweeping a batch of rings from one case with her wings. Soon, the crew had three bags apiece, many of them gathered in a small circle on the floor in front of Sparks. So far, so good.

Then the bell above the door chimed.

All four of the robbers turned to face the newcomer, a stallion who looked just as shocked to see a group of four masked, suited ponies as they were to see him. A few seconds passed in which he looked around at the customers tied up on the ground and the smashed cases before anyone thought to act, Rooster snatching her shotgun from its resting place and bringing it to bear with her wings.

BANG!

In her haste, she squeezed too hard on the trigger, shattering a window just to the left of the frightened stallion, who bolted out the door with a terrified yelp, screaming as he galloped down the street.

"It's the Ponyville gang! The Ponyville gang are here, somepony call the police!"

Sparks sighed and looked over to Rooster, the other two doing the same, although their masks gave nothing away. Rooster, however, managed to look sheepish.

"Bags through the back, now," Sparks ordered, elevating two with her magic as she slung her rifle across her back. It was time for a quick exit. The crew dragged, heaved and lugged the bags through the back door, pushing through the exit into a back ally. Following it along, they came to a small street where a wagon lay waiting, a grey mare with a blonde mane leaning casually against the side of the vehicle. At their arrival, she snapped her attention to them, stretching her hind leg under the tire until Sparks stopped her.

"No need for the mask," Sparks informed the mare as she slung her bags into the back of the wagon. The other pulled up alongside her, flinging theirs in in equal urgency. "The raid's done, the police are on their way, and we need to get out of here quick." She pulled her mask up and threw it in alongside the duffle bags, throwing the rifle and ammo in for good measure. The others followed her lead, tossing away their gear after the stolen goods. The grey mare nodded, sliding a mask out from its hiding place and slipping it into the back before making her way to the front of the vehicle, helping Snapshot into his harness.

"You know what to do, gang," Sparks said to the group. Her voice was much more sultry and heightened now that her mask had come off, the voice-altering spell on it serving to coat her voice as much as the mask itself coated her face. "Rooster, you're with Snapshot. Get that loot to the safehouse and make sure that nopony follows you." The orange mare nodded in affirmation and joined the stallion at the front of the wagon, strapping into the second harness and stretching her wings out in preperation for flight. "The rest of you, go to whatever you've arranged. Make yourself scarce until tonight, then meet up at the safehouse." The others gave brief nods before trotting away in differing directions, casting occasional glances left and right as they turned their respective corners. The vehicle and its two pegasi drivers accelerated along the narrow street before launching into the air, lifting above the buildings and turning in a careful arc. Sparks watched them all disperse before she too moved away from the scene of the crime, aware that she was already wasting time.

The waiting room had two other ponies in it when she entered, and within a few minutes both had been admitted. Sparks only had to pretend to peruse the generic magazines for ten minutes or so before her name was called and she was ushered in. Shutting the door behind her, she closed the sound of the outside world out and allowed herself to relax. No need to worry. After all, she was here. Nopony could accuse her of anything when she'd clearly had an appointment with Colgate, the town's dentist, and especially not when said appointment had been booked a week in advance of the tragic incident at the jewelry store.

"Please, take a seat," the dentist offered her, gesturing to the reclining chair in the middle of the office. Sparks obliged, settling herself into the contours of the chair and letting out a sigh. "That's a lovely suit. I take it that you're helping your sister with her business nowadays?"

"In part," she replied. "I'm setting up my own, but I'm helping her on the side to learn the ropes."

"A wise move." The dentist appeared over Spark's vision, a surgical mask obscuring her muzzle. "I learned much about running a practice from visiting other dentists in Manehatten, Fillydelphia, Canterlot, and all over Equestria. In the end I decided that I preferred the rural life; less competition, and it's generally much quieter. The connections I made were priceless, though. Open wide, please." Sparks obeyed, opening her mouth as the dentist's horn lit up, bringing a miniature mirror and a sickle probe to bear. A few moments passed where the only sounds were the clicking of tools against Spark's teeth before Colgate asked, "What business are you trying trying to set up?"

"A music company," the patient answered once she was free to do so. "I'm hoping to inspire Ponyville's youth to bring their talent forward. It shouldn't be that only places like Canterlot can show off their talent."

"I agree," Colgate responded, observing the back of a tooth with the mirror. "Ponyville has a lot going for it, and it would be lovely to see some of the talent recognised by the major cities in Equestria. What will you call it? Sweetie Belle Productions?"

"I'm still working on the name."

"Maybe something that would attract attention? Something that shows off the most noticeable parts of Ponyville, like 'Everfree Records', or 'Harmony Studios? Or maybe I'm thinking too narrow here." She began to tap against the rearmost tooth, testing it with the probe before reaching down to collect something from the row of equipment she had ready for surgery. "Maybe it should be something a lot more subtle; something that everypony knows about, but which still elusively retains mystique. Something like, hypothetically, 'Ponyville Gang & Co'?"

"I'm not sure that would send the right message to other cities if I'm trying to show of the real talent of this town."

"Maybe you're right," the dentist conceded, rummaging down below for a tool that was stubbornly hiding from sight. "Especially given the latest robbery. The jewelry store just down the street from here was hit. In broad daylight, no less! It's a shame, because I had an expensive necklace reserved, and I know for sure that they won't refund my deposit." She gave a sigh of disappointment, sitting back up with a dental drill now held in her telekinetic grasp. "It's a shame, really. I still think a reference to them would bring Ponyville out into the spotlight."

"In the wrong way."

"I don't know, I quite like 'Scoots and Sparks'." In the chair, Sparks stiffened at the dentist's mention of her code name, but the mare continued on. "I know, of course, that it should be 'Rooster and Sparks', but it doesn't have such a ring to it in my opinion. Neither does 'Scoots and Sweets', which is such a shame. I've always preferred 'Sweetie Belle' to 'Sparks'."

There was a pregnant pause as the words sunk in. A second later, Sparks jumped up, already scrambling for the door, but felt herself forcefully pushed back against the chair and restrained by magic, the drill buzzing to life as it came to rest an inch from her throat. She wiggled in vain for several seconds before admitting defeat, staring coldly at Colgate as the dentist pulled her mask down.

"Oh boy," Sweetie sighed.

"When I said it's a shame that my necklace was stolen," Colgate continued. "I didn't mention that it would actually benefit me, did I? It pays to fall prey to crime sometimes, you know? It's harder to be a suspect or a perpetrator if you're already firmly determined to be a victim. Nevertheless, you and your gang has come to my attention, and now that I'm at least a little bit down on my funds, I want your help in achieving something that I want just an intsy-wincy bit more than jewelery. I think you'll like what I have to offer."

"I'm not so sure," Sweetie replied stonily. "I prefer choosing my contracts."

"That is always preferable," Colgate admitted, waving her hoof dismissively. "But consider the situation here. You are, undoubtedly, not in control of this situation; I have you restrained, and I have a drill. Now, assuming that you could overpower me and escape, you'd have to contend with the police who are waiting outside, and who, with an unconscious or dead body on your hooves, will highly likely arrest you and then, in gathering evidence, will end up investigating into your involvement in the local incident that took place not half an hour ago. In this room, however, I could have one of two ponies. I could have Sparks, the mastermind and head of the Ponyville gang who recently attacked a jewelry store and who foolishly boasted about her past exploits and the names of her compatriots- none of whom shall be named just yet, of course- or I could have Sweetie Belle; a beautifully delightful mare who was just telling me about her love of the music industry and how she intends to start a small company in Ponyville to bring attention to the raw talent that we have in this largely unrecognised town."

Sweetie scowled at the mare. "And just what would your job offer happen to be?"

The dentist licked her lips and leaned in closer. "The Discordian Boulder."

"That thing?" Sweetie could have laughed at what she was being asked if she didn't have a potentially life threatening tool whirring close to her neck. "That's just a pony's tale. It doesn't exist."

"Doesn't it?" The conviction in Colgate's tone gave Sweetie pause, and she tilted her head. "What if I gave you a location? Equipment? Enough money to send you and your team to every corner of Equestria whenever you want for the rest of your lives?" She was sincere, that much was evident. If it were true that such an item existed, and they could find it...well, it was definitely true that they would be set for life. It was an enticing offer, even without the coercion of dental equipment.

"Fine. I'll go on your wild goose chase for you."

"Wonderful!" A beaming smile split Colgate's face and the drill purred to a stop, withdrawing from Sweetie's locality. The white mare lifted a hoof and rubbed at her throat, happy to be able to move again. "Of course, I'll stay in contact and make sure to set you up with everything you need. How is the tooth feeling?"

"Uh, fine," Sweetie replied, taking a second to follow the change in topic.

"Good, good. Stay off chewy, toffee, sticky and crunchy foods for the time being. In short, stay away from Sugar Cube Corner." She gave a quick laugh at her own joke. Sweetie wasn't so amused.

"Just because I'm doing this, it doesn't mean that I'll find it," she warned. "Only one pony ever attempted to find it, and he's not doing so well right now. " She turned to leave.

"I know, and that's the second part of our deal," the dentist's voice intoned from behind, sounding mildly amused. Sweetie stopped in her tracks and turned around, fixing the other mare with a suspicious gaze. "You need a certain stallion to help you find my treasure, and I don't doubt that you'd want him back in the fold with you. I say we hit two pegasi with one cloud."

"You can't mean-"

"Cyclops," she interrupted, answering the white unicorn's question and drawing a silent gasp from her. "I believe that was the name he went by. Regardless, I want to help you rescue him. If we can pull this off, I have no doubt that you'll find The Boulder."

"I'll...need to talk to my crew about this."

"Of course, of course," Colgate smiled, opening the door. "Remember what I said, and don't forget to floss."

"How do we know that she's telling the truth?" Rooster demanded, jabbing a hoof at the table. "For all we know, she could be leading us on for a job she know we wouldn't do otherwise."

"I know that," Sweetie sighed impatiently. "But she told me she can help us get him back. If that is the truth, we can't pass up this opportunity."

"How much do you trust her?"

"Not much, but I'm willing to risk it if it means that we'll get Cyclops back."

"Ah'm inclined to side with Scootaloo here," Manehatten added in her southern drawl. "It does seem a mite risky." She gave a shrug. "It seems like we're riskin' an awful lot based on her word, an' ah don't like it."

"Exactly," Scootaloo confirmed. Sweetie Bell looked at both of them.

"Guys, this is no different to any other contract we take on," she urged them. "We do some jobs for her and we get paid, and as a bonus, we get a friend back."

"Assuming we don't get shoved in jail with him first," Scootaloo suggested morosely. Apple Bloom looked at her uneasily.

"This isn't worse than anything we've already handled, and-"

They swung around as the door creaked open, Sweetie's horn glowing as she snapped a pistol towards the unexpected arrival.

"Do you treat all the guests like this?" Dinky Doo grinned as she walked in, looking at the pistol aimed at her, Featherweight beside her. Sweetie flipped the safety on with her magic and placed it safely on the table again. "Sorry I'm late, things got a bit hectic once we scooted. I checked on Featherweight at the press, and it turns out he managed to write a pretty decent story about the tragic incident down the road. Have you guys heard about it yet?"

"Is it somethin' about two unfortunate ponies being shot by a twitchy friend?" Apple Bloom jibed, pointedly ignoring Sweetie Bell. "Ah can just imagine the headline; 'Ponyville Gang down two members in friendly fire incident'." She held her hooves up and punctuated each word with a hoof jab for effect, and then imitated holding a newspaper, leaning closer and squinting as though reading. "Sources confirm that two members of the infamous Ponyville Gang, known as Cornsilk and Snapshot, were found dead in the treehouse of Sweet Apple Acres this morning after what appeared to be an unfortunate incident of failing to notice ponies coming up a creaky wooden ramp." She shot the unicorn a mischievous smirk.

"Tragic," Sweetie intoned dryly. Scootaloo grinned in silent mirth.

"Anyway," Dinky pressed, closing the door once the Featherweight had stepped in. "I found something today, posted to me. It's weird, because post normally comes to my home, but this was delivered straight to my office. It was there when I got back from stashing the goods." Stepping closer to the table, she slid an envelope onto the wood, letting everypony look at it.

"So what's it about?" Scootaloo asked curiously.

"I dunno. I was waiting until I got here to open it." She gave Sweetie a nod, who carefully pried the paper open with her magic and gently pulled the contents out, laying them down for the rest to see. The group leaned in closer. There were several pages of paper, the topmost page being a letter which all the ponies read through in silence.

Dear Dinky Doo,

Or should I call you Cornsilk? Whichever you prefer. Regardless, I have a proposition for you and your team.

Your work thus far has been impressive, and I am intrigued by your methods and your tenacity, which undoubtedly have proven vital during your recent rough patch, as it were. I find it truly heartbreaking to see such a talented group striking some rocky ground. To this end, I want to help you, and in return, I believe you can help me.

It doesn't need to be said that your crew is lacking a certain member who we all hold dearly in our hearts. He was very prominent in his position, and I think that it's time to call an encore, so to speak. I am offering you a chance to rescue the pony you refer to as 'Cyclops'. Inside this envelope you will find several other documents which detail plans and procedures. This is, however, only the first step.

In order to setup the operation to rescue your friend, I will need you to perform a few prerequisite tasks, but I have no doubt that you'll absolutely smash them, no problem.

Once you have completed your tasks, I will contact you again for another assignment, one which I think you will be pleasantly surprised to receive.

I hope this letter finds you in good health,

The Dentist

"Is that...Colgate?" Featherweight asked uncertainly, glancing at the others, who were all regarding the letter with varying degrees of confusion.

"She could have chosen a better alias," Scootaloo stated, frowning at the page. "How many dentists are there in this town?"

"This isn't the biggest town in Equestria, and yet so far nopony has noticed who we are," Sweetie Belle remind her as she rifled through the paperwork. "I think it's safe to say that the ponies here aren't too observant." The orange pegasus thought about that for a minute before giving a conceding shrug and a nod of the head.

"What ah want to know is, just what is this job anyway?" Apple Bloom spoke up. "And are we gonna take it?"

"From the looks of it," Sweetie murmured, flicking and turning the pages over, "we're going to-" She stopped mid-sentence, a look of comprehension dawning on her face. "Right, that's what we're going to be doing." She gave a nod and placed the papers on the table, getting up and walking over to the drinks cabinet on the other side of the treehouse. The other leaned in closer to the documents, scanning them to see what Sweetie had just realised, but turn their head as they might, and peer as hard as they could, nothing appeared. They glanced over questioningly at the unicorn mare who was in the process of pouring herself some red wine.

"Are you going to tell us what's going on or what?" Scootaloo asked impatiently, waving her hoof in a small circle. Sweetie levitated her glass over and smiled.

"How do you all feel about the mayoral elections?"

"They're boring and dumb, why?" the orange mare responded bluntly.

"Because we are going to dig our hooves into politics."

"That's even more boring and dumb. You know I don't do boring and dumb, Sweets. I do rad and awesome."

"Ah don't see-" Apple Bloom began before her eyes widened in understanding. "Oh, THAT'S what we need to do."

"What?" Scootaloo asked in frustration.

"Ah think we're gonna put Mrs Mare back in her job," the country mare replied, looking to Sweetie for confirmation.

"How?"

"It's simple," Sweetie interjected, pulling a blueprint across to her and pointing a hoof to it. "First, we need to get inside Mayor Ironhoof's house, just here, during his late night meeting while Featherweight provides overwatch."

The group slithered through the shadows, sticking close to the walls and bushes to hide themselves. It was past curfew and security ponies were patrolling the street. Normally, being caught outside after dark would mean a fine, the more expensive the later you were caught out, but for the group, as recognisable as their masks were, they'd be immediately detained. They could not afford for this to go loud.

"Guard approaching from the street on the right," Snapshot informed them, his binoculars sweeping the group's path up to the house. He saw them disappear into the darkness, the guard pony rounding the corner and moving past them a few seconds later. When they were clear, he called them out again, and they continued towards their target. From his position on the roof, he could see Cornsilk telekinetically fiddling with the lock on the back gate as they approached, trying to unlock it on the move. She succeeded, and they pushed the gate open and slipped inside, quietly closing it behind them.

"Okay, we're inside," Cornsilk's voice reported in his earpiece, the familiar clicking of a lock sounding through, followed by a door opening. "He shouldn't be home for another hour and a half, right?" she asked. Snapshot quickly checked the watch he kept on him; 21:57. Perfect.

"Correct," he confirmed. "Need some company?"

"That would be appreciated," she replied, and he could hear her smirk in her voice. Smirking himself, Snapshot stealthily launched himself off the roof and glided towards the house.

"Dinky will pick the locks on the gate and door and get us into the garden, and then into the house," Sweetie continued, sweeping her hoof across the blueprint. "Remember, we need to lock everything on the way out, and leave it exactly as it was. Nopony must know that the house was compromised." The others nodded their understanding. "Once inside, Featherweight will join us, and we'll work our way upstairs to his bedroom, and then across to the lounge. Both rooms have a safe in them, and we need to find the contents of those safes."

Snapshot lead the way, his light touch making him the perfect lead, keeping an eye and ear out for anything out of the ordinary. Manehatten followed closely, as did Cornsilk. The stairs creaked a little as they ascended, but not to a worrying extent. Once on the landing, they moved in opposite directions, checking each door to see what lay behind it.

"Over here," Cornsilk whispered. Sparks peaked through the door and nodded, and the two slipped inside. Meanwhile, Rooster motioned Snapshot over and together they crept into another room. It was the bedroom, and Snapshot immediately slinked over to the cupboard. At the back he found a hidden pannel, and behind that, the safe they were looking for.

"Found it," he whispered, reaching out to fiddle with the heavy metal construct.

"Fake pannel?" Sparks asked through his earpiece.

"Yep. In the wardrobe. Was yours behind the portrait?"

"As always."

"But if we're not meant to let anypony know we were ever there, then how are we gonna get into the safe?" Scootaloo asked. "Pretty sure we can't drill, saw, or explode it open." Sweetie Belle smirked and tapped at one of the documents. The orange mare looked where she'd pointed and gave a comprehending nod.

"Ah guess time under anesthetic makes honest ponies outta scoundrels," Apple Bloom commented. "Nice of her t' include it fer us."

"Remind me to never go under anesthetic again at Colgate's again," Scootaloo mentioned.

The combinations they'd been supplied with worked and the safe door was soon opened at Snapshot's deft touch. He had to shield his eyes from the golden glow as it swung open.

"Gold?" Rooster asked, looking inside. "Where did he get that from?"

"Equestrian Central Bank, where else?" Sparks replied through the earpiece. "Less obvious place to keep it safe than the bank itself, and probably a payment for the mayor to deal with us. Probably helped fund his campaign to get into office. Two pegasi, one cloud."

Rooster snorted. "What, they think we're gonna rob them?"

"More than likely." There was a pause.

"Are we?"

"More than likely."

Rooster shook her head as she unzipped her bag and opened it for Snapshot to start placing the gold inside, one brick at a time. After it was carefully stacked, Rooster zipped up the bag and slung it back onto her back while Snapshot placed a replacement into the safe before sealing it back up and replacing the pannel. When he shut the door, it was like the safe had never been opened.

"What's even in the safes?" Dinky asked.

"We don't know," Sweetie replied. "All we do know is that we need to find out because its apparently valuable and dangerous enough to keep secret. Also, Colgate wants us to put this in one of them." She levitated up a jewel-encrusted necklace.

"Where did she-"

"She had a reservation," Sweetie preempted. "Clearly, she knew what we were going to do and decided to use it to her advantage. Unfortunately for Mayor Ironhoof, the police are going to find it in his possession."

"What have you found?" Rooster asked as she and Snapshot entered the lounge. Cornsilk and Sparks looked at each other and then moved aside for the other two to see.

"Gotta say; I didn't expect that," Snapshot commented. He gave the contents a look over and glanced at Rooster. "Fancy any?" She shot him a look from behind her mask.

"I've got a diet to stick to," she retorted. "Clover would be fine, but I'm not into the heavier stuff."

"We're taking a bag," Sparks informed them, a command which drew the attention of the other three. "We're planting one in his office drawer, and tomorrow, Snapshot is going to attend an interview. When he opens the drawer, photograph it, and publish a story with it, if you can. The scandal will bring the police's attention here, if not the public's." The group nodded at the plan, and Sparks threw a packet of the white powder to Rooster and closed the safe, levitating the portrait back into place. The pegasus ignored the look that Snapshot gave her.

"Sounds simple enough," Apple Bloom commented, looking confident in the plan. "Get in, find the safes, open 'em up, take anything valuable inside, plant evidence, lock everything back up, an' get out. Nice an' simple, like old times." She shot the others a grin. "Ah'm definitely in."

"Good," Sweetie chirped, a smile brimming on her face. "Any objections?" Nopony spoke, and she gave them all a nod. "I'll let Spike know," she said, standing up.

The timing was perfect. As the mayor left the town hall, turning the light off in his office, Cornsilk picked the lock on the window, allowing Snapshot to creep in with the illicit package. He was only inside for around ten seconds before he emerged at the window again, motioning for her to lock it again. He closed it swiftly and silently, giving an exaggerated nod a few seconds later to let her know that it had worked. Creeping noiselessly around the roof, he was out of sight before the mayor had even stepped outside the door. As Ironhoof made his way down the steps and the nightly patrol locked the door shut behind him, the gang was heading to the very edge of the town, making their way over to their hideout to dispose of their masks, suits, bag, loot, and latex hoof wraps. There was no indication that anypony had unlawfully entered either the town hall or the mayor's house, or even been out after the curfew. Nopony would know. The mayor would go to sleep, his mind at ease believing that with another tax collection in a week, he'd have more money from the townsfolk to accrue more luxury, and a disposable amount to deal with the pesky Ponville Gang.

The morning after, he would wake up and begin the most stressful day of his career.