”We round a racetrack through your mom’s kitchen chairs, and fought the shadows back down your dark basement stairs…”

Sky’s personal alarm-clock went off atop her tower again. This time it was a song about hot air balloons, which was still close enough to gloating about the wonders of flight that Sky was sufficiently pissed off by it.
“Oh Luna, is the building on fire?” Shadow trotted into her big sister’s room, rubbing her eyes sleepily.
“If it’ll get him off the fucking roof, I’m tempted…” Sky growled, burying her head under her pillow and groaning.
Shadow rubbed her eyes on her wings, making her way over to the balcony and peering up at the perpetrator. “OI! PISS OFF!”
“He can’t hear you…” Sky shook her head, getting up while keeping the pillow clutched around her ears. “I’ll be back in a second.”
And with that, Sky clambered up the stairs, popping open the top hatch and making her way onto the roof.
“Unbelievable.” Shadow trotted over to the kitchenette, starting to make the two of them cups of coffee. Usually Sky was hesitant to let her drink coffee...apparently it turned her into some kind of evil bitch...but Sky wasn’t here right now. Besides, Shadow was pretty sure that she was exaggerating.

”I’ll be out of my mind, and you’ll be out of ideas pretty soon, so let’s spend the afternoon in a cold hot air ballOOOOOOO…!” There was the unmistakable sound of a pony bucking someone else where Celestia doesn’t shine, and suddenly Tone Deaf’s voice had changed to some kind of pained falsetto. The song died off not long after that.

“Now get off my bloody tower!” Sky shouted from upstairs. Shadow panicked. She didn’t have much time before her big sister caught her with the caffeinated contraband. The young mare stirred up the strongest mug of coffee she could, downing the whole lot of it and tossing the mug out of the window.
“What the hell are you doing with the kettle?” Sky cocked her head as she peered down the stairs at her little sister. She knew that Shadow was up to something, but couldn’t possibly have suspected that she was already too late to stop it.
“I...I was just…” Shadow’s mind raced. “I was just making you some coffee, that’s all!”
“You’re vibrating.”
“I...am?” The filly looked down at herself, her legs blurring. “Um...wow, I guess I...am...aren’t I?”
“You got into the coffee again, didn’t you?” Sky deadpanned.
“Pffft...no! I hate coffee! Besides, you told me I’m not meant to have any.” Shadow waved a hoof dismissively, spreading her wings defensively. They started rapidly beating of their own accord, catapulting her straight into the ceiling.
“For fuck’s sake, sis!” Sky giggled, trotting down the stairs and catching Shadow as she plummeted back to earth. “We’ve already talked about this! You can’t hold your coffee. You’ll be grumpy as fuck later.”
“Ugh...come on Sky...I’m old enough...I’ll be fine.” Shadow groaned, rubbing her head.
“Didn’t look fine when you were playing a game of pony squash just then.” Sky stuck her tongue out.
“I’ll be all right...I’ll be all...ri….riiiiAAAAAARGH!” Shadow hopped out of Sky’s grip an immediately shot off again, bouncing off of the wall and flopping pathetically onto her big sister’s mattress. “Owww…”
“Finished?” Sky rolled her eyes, giggling at her slightly concussed little sister.
“Wha...what’ve we gotta do today?” Shadow replied, opting to stay still for now to try to bring the room back into focus.
“We’ve gotta hit the library again.” Sky trotted over to the kettle, making herself a cup of coffee and taking a sip. “The letter in Money Bags’s office mentioned a pony calling themselves “RH.” I bet that’s one of the ponies whose details I took down last time we visited there, a mare called Red Herring.”
“Seems legit.” Shadow nodded, making a spirited attempt to keep her wings tucked in. If she spread them again, something terrible might happen. “Sure you’re not just looking for an excuse to check out your waifu again?”
“He...hey!” Sky protested, nearly spitting out her coffee as she spread her wings defensively. “She’s not my waifu! I’m not like that!”
“Sis?”
“What?”
“You’re blushing.”
Sky tucked her head under her wing, still sipping her coffee. “I...I was just thinking of something embarrassing…”
“Like what you’re gonna look like on your wedding day with her?” Shadow giggled, rolling onto her front and grinning wickedly.
“Shut up! I just said, I’m not like about! Seriously, what’s the longest you’ve seen me hold down a relationship?”
“About as long as it takes for them to come home and meet me, generally.” Shadow shrugged. “Want me to introduce myself to Penfeather today?”
“DON’T YOU DARE FUCK THIS UP FOR ME!” Sky freaked, dancing around nervously. “I mean...um...no, we don’t wanna get thrown out of the library because you won’t stop screwing around.” She took a deep breath, pulling her head out from under her wing.
“So you don’t want me to come?” Shadow cocked her head.
“Actually...I’d like it if you did. I kinda need a pony to help me talk to her...I mean, just in case we run into her...which we might not…”
“You want me to feed you lines?” Shadow cocked her head, fighting to keep a straight face as a million evil ideas crept into her caffeine-fuelled mind.
Sky nodded, blushing deeply. “Um...I mean…”
“Sure, sis.” Shadow nodded, getting to her hooves and trotting over to nuzzle her. “I’ve got your back. You know that.”
“Th...thanks…” Sky smiled with a little more confidence, nuzzling the filly before finishing her coffee and trotting off.
Shadow waited until she was certain that she was alone before she started to cackle, the evil power of the coffee in her system overwhelming her and turning her into a wicked filly of mischief and cheekiness.
When it came down to it, she wasn’t much different from normal.
“Oh, I’ll feed you lines all right, sister dear.” Shadow grinned, rubbing her forehooves together evilly. “And they’ll be unforgettable!”

“There’s no way you’re going in there dressed like that, missy.”
“What?” Sky asked. “What’s wrong with it?”
Shadow deadpanned at her. Somehow, Sky had managed to pick up a light blue skirt on the way to the library, and she was now wearing it. It wasn’t that it didn’t suit her, Shadow was just honestly concerned about what would happen if somepony she knew saw her with this big galoot.
“Look, it’s nice, okay?” Sky said defensively. “And you can go in first so you can pretend that you’re not related to me, all right?”
“I’m not related to you.” Shadow chuckled, tightening the belt that she’d fastened around her wings to prevent any further accidents. With one last look at her sister, Shadow shook her head, trotting into the library.
Silly filly… Sky thought to herself, following behind her.
The two of them made their way past the counter, trotting into the personal records section of the library and beginning to search for more details on the pony named Red Herring.
“Here we go.” Sky grinned, holding up a book triumphantly. “She’s a mare...not bad looking either…”
“Oh come on sis, at least fuck one pony at a time.” Shadow groaned exasperatedly.
“Make me.” Sky giggled, looking through Red Herring’s details. “Huh, she builds ships.”
“What, so she’s like a matchmaker or something?”
“No, like, airships.” Sky clonked her sister around the back of the head. “She runs a company that makes them.” She frowned as she read further. “It looks like Red she’s made a fuckton of money off of building ships for the Equestrian Navy.”
“Is that what we’re gonna do, sis? Piss off two incredibly rich ponies in two days?” Shadow chuckled. “We’re either ballsy or completely off our rockers.”
“Maybe a little bit of both.” Sky chuckled, ruffling Shadow’s mane and copying down the factory address. “Besides, since when have we let common sense get in our way?”
Shadow gave Red Herring’s file one last concerned look before smiling up at Sky. “You’re right. Come on, let’s go get in even deeper shit.”
Sky gave her little sister a quick hug before putting the book away. “You’ve got it.”
The two of them were halfway to the door before Sky froze.
“Pssst…”
“What?” Shadow grinned. She already knew exactly what Sky had just spotted.
“Um...she’s just over there…” Sky whispered, nodding across the library at the as-yet-unsuspecting Penfeather.
“So go over and talk to her.” Shadow shrugged, giving her big sister a nudge.
“Um...okay...I can do that…” Sky hesitated, biting her lip. “How...how do I...you know…start talking to her?”
“Slap her ass.” Shadow said seriously, the tiniest hints of a big shit-eating grin playing about her innocent features. “Trust me, it’s super-romantic. It’ll get her attention for sure.”
“Are you sure about that?”
“Positive.” Shadow replied, struggling to hold a caring, compassionate expression on her face. “Librarians love that sort of thing. They’re all secretly kinky. You know that.”
“Ye...yeah, I guess you’re right.” Sky gulped. “Well...you’ll come with me to help me...speak to her, right?”
“Sure! I’ve got your back, sis!” Shadow beamed, trying to suppress the urge to cackle maniacally again. She placed a hoof on Sky’s shoulder encouragingly. “Come on, you’ve got this. Just go and slap her and I’ll run you through it from there, okay?”
“O...okay…” Sky nodded. Any other time, alarm bells would have been going off in her head about Shadow’s sudden willingness to help, but right now she was too nervous to really register them, more fixated on making sure she didn’t mess this up. As she trotted towards Penfeather, Sky’s mind raced, her head filling up with a million ways that this encounter could go horribly wrong.
It’s okay. She thought to herself, carrying herself with a little more confidence as she approached the librarian. Shadow’s got my back. Everything’s gonna be all right.
With the same confidence, Sky drew back a hoof and promptly slapped Penfeather across the flanks.
There was a deafening smack, followed by the world’s most damning silence.
“Um...can...can I help you?” Penfeather asked timidly, slowly turning to face Sky with wide, shocked eyes.
Sky had gotten her attention, all right.
“This is going great!” Shadow whispered in her big sister’s ear. “Okay, say this next…”
Sky listened intently to her little sister, failing to realise what a titanic mistake she was making by so doing.
“Erm...okay...Penfeather...do you have a map?” She asked, forcing a very nervous smile.
“Huh? Why?” The hapless pony cocked her head, taking a step back out of confusion and just the tiniest twinge of fright.
Shadow muttered something else in Sky’s ear, before sticking a hoof in her own mouth to stifle her giggling.
“Because…I keep getting lost...lost in...your ass!” Sky blurted out.
Shadow lost it at that point, rolling over onto her back and descending into a fit of the giggles.
It was in that moment, the longest, most agonising moment of her life, that Sky realised that she’d been had.
“H...huh?” Penfeather took another step back, spreading her wings as if she was really considering fleeing for her life.
“I...am...so...sorry…” Sky said quietly, trying to ignore Shadow’s hysterical laughter. “I...my little sister...she said...that she’d help me talk to you...because...I got...erm...nervous...and...WHAT’S THAT OVER THERE?” Sky gestured madly at something over Penfeather’s shoulder.
Against all the odds, the poor confused librarian glanced over at where Sky was pointing for the briefest moment, and when she looked back, the pony was gone. All that was left was the sound of the library’s front door slamming shut, the sound of Sky’s terrified retreat dying away to nothing, and then Penfeather was left in awkward silence.

As soon as they were well clear of the library, Sky yanked Shadow off of her back, doing a terrified little dance.
“What the fuck were you thinking!” Sky yelped. “Now I’ll be lucky if she doesn’t call the guards on me!”
“Aw come on, sis!” Shadow giggled, grinning up at her sister with happy tears in her eyes. “You’ve gotta admit, that was pretty good.”
“Pretty good? PRETTY GOOD? That was pure evil, you psycho bitch!” Sky grabbed her little sister by the shoulders, shaking her wildly. It did nothing to quell Shadow’s case of the filly-giggles.
“You sh...should see your face right now!” Shadow squealed, wiggling her hooves with excitement. “It’s fucking priceless!”
“Okay, just for that, you’re officially worst pony.” Sky pouted, holding onto Shadow. Her hooves drifted down to the belt fastening her little sister’s wings in place. If she released it, that little filly would likely go shooting off like an untied balloon, but Sky wasn’t that mean.
She was far, far worse than that.
Shadow’s giggling subsided as Sky grinned at her, hugging her little sister in much the same way as she’d hugged Sparky only a few nights earlier.
“Uh...sis...you’re...um...you’re not mad about that, are you?” Shadow gulped, suddenly quite nervous. It was something about the look that Sky was giving her. Something about it was making her more scared for her own safety than that golem had done last night.
“Nah, I’m not angry at all!” Sky beamed, holding Shadow close. “It was a great prank. You really got me, didn’t you?”
“Ye...yeah…” Shadow nodded. Something told her that she’d just somehow signed her own death warrant, or that perhaps some kind of horrible revenge was forthcoming. Any minute now…
However, to Shadow’s surprise, it didn’t look like Sky wanted revenge. She honestly seemed to be okay with this. In time, Shadow found herself hugging her big sister back, resting her head against Sky’s chest.
Why the hell is she taking this so well? Wondered the filly. Something’s wrong here…
Sky finally pulled away, still smiling kindly. “Come on sweetie. Let’s go get ready to case Red Herring’s place.”
Shadow smiled timidly as Sky wrapped her good wing around her, not suspecting that her big sister was going to bide her time, waiting for the perfect moment to strike and get her revenge. Someday soon, sooner than Shadow would have liked, things were going to get incredibly bad for that poor filly.

Across the city, a rotund unicorn hesitantly pushed open Screwdriver’s front door. He wasn’t used to coming to this part of town alone, but something told him that he couldn’t rely on the Royal Guard for a matter of this nature. He had to resort to other means, and he wasn’t exactly certain how to proceed.
“Um...hello…” Money Bags whispered to the bartender. “I’m...erm...looking to employ the services of...a...specific kind of pony…”
Screwdriver stopped his obsessive glass-cleaning, staring at Money Bags as if he was some kind of alien.
“You want Wild Night, just down the road from here. Nicest mares in town.” He said simply.
“Um...no, I mean...a different type of pony…” The millionaire corrected himself, shaking his head. “One with a...erm...specific skillset.”
“Oh, well if that’s the way you swing, there’s a little bar called Rock and a Hard Place a couple blocks over.” Screwdriver nodded, smiling. “There are stallions down there that’ll do anything if you grease their hooves just right.”
“No, I mean...erm...a pony who can do certain things to another pony…”
Screwdriver burst out laughing. He never could resist messing with ponies like Money Bags. They were so innocent and awkward. “O...okay...okay mate...what kind of pony do you really need?”
“A...erm...bounty hunter.” Money Bags said, a little taken aback by Screwdriver’s attitude.
The bartender nodded. “Upstairs, first door on the left.” He gestured at the staircase at the back of his inn.
“Thank you…” Money Bags nodded politely, trying not to make eye contact with anypony else at the bar as he made his way towards the back.
“Um…” He said nervously, looking back at Screwdriver. “This isn’t going to be a prostitute or something, is it?”
“Now why would I lie to you?” Screwdriver replied, giving Money Bags a yellow-toothed grin and a wink.
Money Bags gulped, making his way up the stairs and into the dark hall beyond. Screwdriver’s doubled as a cheap hotel and hideout for some of the city’s undesirables, and it was just such an undesirable that Money Bags sought today. No one got away with robbing and humiliating him, and he was going to show everyone in Canterlot what happened to ponies who messed with him.
He took a moment to tidy himself up, before knocking on the door.
“Come.” Came a gravelly voice from within.
Fully aware that he was putting himself in mortal danger, Money Bags pushed the door open.

The room beyond was bare and dark, unfurnished besides a bed, a table and two chairs. Money Bags’ eyes were drawn to the occupant of one of the chairs, a pony shrouded in shadow, smoking a cigar, the dim light reflecting off of his red eyes.
“What do you want?” the pony demanded, sounding like someone doing the worst and most offensive Batmare impression possible.
“Um...are you a bounty hunter?” Money Bags inquired, closing the door behind him as he stepped into the room, cautiously approaching the table.
“No.” The pony shook his head, his shaggy black mane flying out around him in the darkness. “I’m an assassin who sometimes takes ponies alive...when my clients really want me to.” He leaned across the table, revealing a scarred grey muzzle. Everything about this stallion screamed dark and edgy. Money Bags suppressed an excited squee. This guy was perfect.
“I need a pony...taken care of.” Said Money Bags, taking the seat across from the mysterious edgy pony and grinning. “Her name’s Sky Runner.”
“Yeeeeeeah...Sky Runner...I know her.” He growled, baring his teeth. “I can take care of her for fifty thousand bits, plus expenses.”
“Are you sure you can do the job? I don’t want to invest my money unless I know you can deliver.” Money Bags frowned sceptically. “That pony’s given me a lot of trouble.”
“You sound just like my sergeant when I was in the Royal Guard.” The stallion growled grimly. “And look where that got him...in a shallow grave, just like the rest of my unit. Eighty good ponies, all gone the same way as my mom and dad, who were killed by a rampaging bear. I’ve got a morbid fear of bears because of it, you know…”
“Erm...okay, right, I believe you.” Money Bags waved a hoof to silence the stallion before he gave away his entire life’s story. “How about your expenses and twenty-five up front, and the rest when you bring her back to me?”
The pony sat back, his cigar burning in the darkness. After the longest time, he held out his forehoof. “Call me Whiplash.” he growled. “You and I are gonna do some business.”
“Oh...good…” Money Bags smiled, shaking it gratefully. “How soon can you start looking for her?”
“Right away.” He nodded, getting to his hooves. “Just one question. Dead or alive?”
Money Bags bit his lip for a moment, looking at his hooves before meeting Whiplash’s gaze.
“The world won’t miss her.”