Waking Night

by CrowMagnon

Part 6 - Returning Generosity

Waking Night
by Crowmagnon

"I promise, there is a very good explanation for all of this... and as soon as I know what it is, I'll tell you."

-- Agent Dashing Doo, circa 798AE, regarding "The Noodle Incident"

---

It was Waking Night morning, and Applejack scowled at the sight before her. She was staring into a full-length mirror, and was thoroughly displeased with what she saw.

Off to the side, Fancypants offered a genteel smile. "Well, if nothing else, you look ravishing. Green is most certainly your color."

"I know. I hate it," Applejack replied sourly. In all honesty, she truly wished that she could argue with her dear friend's appraisal. In her day-to-day life, she favored a certain level of androgyny in her appearance; mostly because, as Apple Orchard's founder, she insisted on working at least as hard as her employees so long as the company was still getting off the ground. Long hours in the office day after day while needing to present a respectable image at all times made a short, easily-managed manecut and straightforward business suit far more practical than if she favored a more high-maintenance, "frou-frou" ensemble.

The mare looking back at her from the mirror's reflection, by contrast, was one who was ready for a night out on the town. The cut of her dress created an alluring illusion, making her legs look longer and slimmer than they actually were. Makeup carefully applied by Silk Sheets, the head maid, further enhanced her femininity, drawing attention to her lips and eyelashes. Her somewhat coltish blond mane had barely been touched, but with the addition of the cosmetics and a professional styling, she looked more like a sophisticated fashion model.

"It's just a shame that Fleur isn't here to see this. I'm sure she would be delighted," Fancypants offered. His optimism was rewarded ever so slightly as the flicker of a smile graced Applejack's lips.

"If Fleur were here, she would suggest some insane caper to smuggle me to Ponyville."

"And, as retribution for putting you in such a position in the first place, plot to embarrass the prince while somehow securing his endorsement for Apple Orchard at the same time."

Applejack laughed and looked toward her friend. "Why Fancypants, you almost sound approving of such delinquency."

Fancypants gasped in mock indignation. "My dear, I would never approve of my sweet cousin engaging in such scandalous behavior." He stepped forward to place a hoof around her back and added, "Your beau proving her love by running circles around your enemies, no matter how powerful or influential, though... well, I would certainly enjoy seeing that."

Applejack smiled, but her eyes began to water as she leaned in to embrace Fancypants. "I... I really wish that she was here right now," she whispered, her voice breaking as she sniffled against his neck. "I don't know how I'm going to get through the night."

Hugging her back, her friend assured her, "You are a good mare, Miss Applejack, and you aren't alone. We're all doing our best to find a way to fix this."

-----

"There's no way I'm going to be able to fix this," Check List groaned. After running around the city on his employer's behalf the entire day, struggling in vain to catch the prince and talk him into re-scheduling, the unicorn's path ended in a Lower Canterlot tavern with nothing to show for it but a mug of hard cider.

"Must've been somepony special."

"Hmm?" Check List looked over and saw an older, cherry-red unicorn mare nursing a cocktail a few seats down the bar.

Despite the heavy makeup and wrinkles around her eyes, the mare was still quite attractive, bringing a blush to his cheeks when she gave him a drunken, flirty smile. "Whoever you're moping over, cutie. In my experience, a pony doesn't look that sad on Waking Night unless some mare broke their heart. Or stallion."

"She's a mare," Check List quickly clarified. "B-but it's not like that! She's my boss. I let her down."

The older mare lifted her drink in her aura and skeptically replied, "Really? A young fellow like you getting all worked up over his boss? And you aren't carrying a torch?"

Check List shook his head. "Really, it's not like that. I owe her... everything." He took a sip of his own drink, then asked, "You ever heard of Flim Flam Incorporated?"

The mare tapped her chin in thought. "I think I read about that in the papers a while back. Wasn't that some kind of scam?"

Check List nodded. "Tricking inventors out of their work and patenting it for themselves, shady investment deals, fraud... and I worked for them. I-I didn't know what they were doing, at first. I mean, I was fresh out of college and I just needed to get my hooves wet, and whenever something seemed crooked, they had this way of making it sound like everything they wanted me to do was just how things worked in the business world. So I did whatever they said until one day, it was just too much to handle.

"So I blew the whistle on them. I took the records that had all their dirty dealings and turned them in to the authorities. It was a big scandal for a while, but they made some deals. The company was dissolved and almost all their assets got seized to pay back the ponies they'd scammed... and I was out of a job."

The stallion sighed and rested his chin down on the bar. "I tried to find another job somewhere else. Somewhere better. But wherever I went, as soon as they found out I was a whistleblower, they turned me away. Even honest businesses don't want to keep somepony around if they think he might snoop around and steal their secrets.

"So there I am, barely out of school, desperate for work, and every place I apply at treats me like I've got pony pox."

"It's a rough world," the mare sympathetically replied. "At least your boss said 'yes', right?"

Check List chuckled and lifted himself up to shake his head. "That's the thing. She wasn't the one who had to. I'd already given up by then, and was about to go beg for a job at Burger Princess just to make rent when I heard a knock at the door. I open it up and there's this mare standing there. She looks me over, then asks, 'Check List? My name's Applejack. I heard you're looking for a job, and I need some good ponies on my team.'"

The older mare raised an eyebrow. "A white horse come to your rescue, just like that? That sounds a little too good to be true."

Check List couldn't help but laugh. "Tell me about it. After all those rejections, half of me wanted to throw myself to the ground and kiss her hooves, the other half figured it had to be a trick. Like maybe she wanted to hold the fact that nopony else would take me on over my head, to keep me loyal. But I started working with her and... and she was everything those con artists at Flim Flam Inc. weren't. She said she wanted me to work for her because she wanted ponies who'd do the right thing, even when it was hard.

"And it sure wasn't easy, starting out. Still isn't, but she never let the fact that it was tough stop her from putting everything she had into it, and that made the rest of us want to do the same." His ears drooped as he admitted, "That's probably where I screwed up. I was trying so hard to impress her with what I could do to help the business that I forget sometimes that she's a pony like the rest of us."

"Sounds rough," the mare replied, swirling her drink around in her glass. "But there's no point beating yourself up over it now, is there? Sounds like you did everything you could."

Check List hung his head, but then jolted upright again when he felt a hoof slowly running up and down his back.

Leaning in, the older unicorn whispered, "You seem sweet, and you're not doing anything else right now. How about you just stop thinking about your boss for a while and come on up to my place? I'll put on something nice, and we can have our own Waking Night ball."

Check List's face turned beet red as the mare leaned in closer. Despite the age difference, she really was attractive, and her perfume smelled like apple blossoms...

All of a sudden, he gasped. "That's it!" He quickly chugged the rest of his cider and hopped down off the barstool before turning to the mare and taking her hooves in his own. "I'm really, really sorry, but there is still something I can do. Umm... but maybe later...?"

The mare's flirty demeanor evaporated into a bemused frown.

"Right... sorry. Thanks for the talk, I've just gotta go. My boss... she's special," he stammered as he put enough bits on the bar to cover both his drinks and the older mare's. He then ran off out into the crowded streets.

Once he was gone, the mare's frown turned upward into a wistful smile. In a thick, lower-class Manehattan accent, she mused, "Well, can't argue wit' dat. At least I don't gotta use Plan B." Her horn began to glow with a pink aura which spread down over her entire body. As the crow's feet around her eyes faded to nothing, her mane and coat changed color to pink and a creamy white, respectively. She then picked up her drink again and took a long sip. "Ugh... between Trixie an' Blueblood, I'm gonna need ta actually take a trip ta Prance after this..."

-----

Applejack sighed softly as she looked out the window. The afternoon sun shone down on Equestria, and from her vantage point in Fancypants's tower mansion, she could see the township and farms of Ponyville off in the distance. Within sight, but so far away.

After the initial fitting, she had taken the dress back off. Ostensibly, this was to keep it from getting dirty or damaged before the ball, but the truth was that wearing it felt like being wrapped in chains, and she intended to remain out of it for as long as absolutely possible.

"Why does Prince Blueblood even want me to accompany him, anyway? I'm not even on the market, let alone for some stuck-up, antiquated, useless know-nothing who doesn't have anything better to do than demand a date with a mare who doesn't even want to be here, and ride around in his gaudy sky carriage. Just look at that thing..." she grumpily muttered, catching sight of a team of pegasi in platinum armor, carrying along a blindingly white and gold carriage.

The Blueblood family crest was clearly visible on the doors, set in glittering blue sapphires. While she watched it circle around, she realized, to her horror, that it was descending toward the street in front of Fancypants's tower.

"He's here? Already?! I thought I would have more time!" Applejack began to panic, and rushed back to the guest room.

When she arrived, she immediately went to the wardrobe, only to find nothing but air where the party dress had been. Her green eyes went wide in shock as she pulled open the lower drawers and started frantically searching through them, discovering in the process that even the clothes she had brought from Manehattan were missing.

"Ms. Applejack?" Silk Sheets poked her head into the room. Her voice cut through the blind panic that Applejack was in.

Turning toward Silk, Applejack rushed to her and started shaking the unicorn maid. "My clothes! Where are my clothes?!"

"I-I-I pa-a-acked them awa-a-a-ay fo-o-or your tr-i-i-ip ba-a-ack to Po-onyvi-i-ille!" Silk explained through the shaking. Applejack stopped and stared in disbelief at her, and once Silk's eyes stopped spinning, she gave Applejack a smile. Her horn glowed, and a train ticket rose up from the neckline of her uniform to hover in front of the businessmare. "You have to hurry, though. The train departs soon."

Applejack's eyes started watering, and she let go of Silk in order to wipe them dry. "You... Please don't tease me like that. It's a sweet thought, but the prince...! Apple Orchard's future..."

"Don't worry about Prince Blueblood," a familiar male voice told her. "I started this whole mess, so I'll help you get out of it."

"Check List?" Applejack looked up to see her assistant, and the tears that had been welling up in her eyes instantly evaporated as her jaw dropped to the floor. She placed a hoof beneath her chin and lifted it up so that she could ask, "... What are you doing in my dress...?"

"I know, it's a rush job, but it's the best I could do," Check List said, looking himself over. Dyed orange and blond, he fidgeted to make the party dress fit better. Applejack stared in silence, unsure if she should be impressed or chagrined that the illusion was actually fairly effective. The features that had enhanced her own femininity when she had tried it on earlier now did an equally good job of masking her assistant's masculinity, and the addition of a hat with a light veil hanging down over his face covered up his horn.

Applejack stood poleaxed at the sight for a few seconds, then shook her head to clear it. "I... have no words. You helped him with this?" she asked Silk, who proudly nodded. "This is insane! What if he wants you to dance?"

"I'm prepared to make that sacrifice," Check List replied resolutely.

"What if he wants to kiss?"

"... I'm prepared to make that sacrifice."

"What if he wants to-mmmph?"

Check List quickly interrupted her by placing a hoof over her muzzle. "Please... don't ask how far I'm willing to go," he pleaded before lowering his hoof. "Look, you've spent years thinking of the company, your employees, your customers... so tonight there's only one pony you should have to think about, and she's waiting for you down in Ponyville. I'll take care of things up here."

Applejack seriously considered arguing against it. As much as she wanted to simply take the tickets and run, the risks were so great... but as soon as she heard a loud, insistent knock at the front door, she wrapped her forelegs around him.

"This is the most insane thing I've ever given somepony a bonus for," she told him, "but if Apple Orchard is still in business when this is over, you'll have more than earned it."

"All part of the job, boss," Check List replied.

With that said, Applejack let go of her assistant and grabbed the levitating ticket in her mouth so that she could tuck it away in one of the pockets of her suit.

-----

The run to the train station was a hard one. As a veteran runner of charity marathons back in Manehattan, Applejack was no stranger to staying fit or pushing herself, but the massive herds that she had to weave her way through as she hurried down the mountain kept her from going all out.

A particularly dense throng of ponies had gathered in the square beneath the palace as they waited for Princess Celestia to make her annual appearance. She did her best to avoid running into anypony, but as she hurried along, she felt the urge to check her pocket to ensure that the ticket was still securely in place. Applejack lifted one hoof to verify it, and as she loped along in a three-legged gait, several young ponies came running, screaming and giggling, out of the hedge maze exit and right into her path.

With a startled yelp, Applejack did her best to swerve out of the way. Her unstable footing caused her to lose her balance, though, and as she felt her hooves slip out from beneath her, the cobblestone streets swiftly rose up toward her.

Before her face could have an intimate encounter with the street, however, Applejack felt four legs wrap around her, and she was yanked up above the crowd! She gasped in surprise, unsure if her eyes were deceiving her, but when she glanced over her shoulder, she found herself looking into the fang-filled grin of a vampony holding her aloft on leathery wings.

"Careful, there," the yellow, pink-maned "vampony" giggled, her voice slurring from the effort of talking with false teeth in her mouth. Fortunately, the wing coverings designed to mimic a thestral's bat-like appearance were designed with pegasi in mind, so she had no trouble keeping Applejack aloft. "That'd be one trip you wouldn't want to take a souvenir from!"

Applejack let out a sigh of relief. "Thank you! I was just in a rush, and--"

"What's the rush?" the pegasus asked, cheerfully interrupting her. "Did you want to try the hedge maze before Princess Celestia shows up? You might just have what it takes to save Princess Luna from eternal slumber!"

Applejack shook her head. "No, no... I need to get down to the train station, so I can get back to my family!"

Fluttershy pouted as she carried Applejack over the crowd. "Awww, no time for a thrilling maze adventure, huh? Well, I guess I can give you a drop."

"Give me a drop? What does that mean?"

"It's like giving somepony a lift, but the other direction," Fluttershy replied as she released Applejack from her grip. The businessmare's eyes opened wide, and she let out a scream as she tumbled down, finding that the pegasus had carried her out beyond the edge of the level she had been on moments ago!

Instead of crashing against the rocks below, or the roof of somepony's house, though, Applejack's short fall ended with her landing safely (if roughly) into the back of a moving wagon, the impact cushioned by piles of empty sacks. After reminding herself to breathe, she picked herself up and looked around. The two goats pulling the wagon also looked right back at her, and let out a questioning bleat.

"No hard feelings, I hope? It's just not Waking Night without some surprises," Fluttershy called down to her with a giggle. To the goats, she waved and told them, "Just drop her off at the train station before you come back with the candy! We can hold out a while longer with what we've got up here!"

Applejack blinked a few times and wheezed to catch her breath before calling back up, "Th-thank you! I really appreciate this!" Though in the back of her mind, she desperately hoped that it would be the last Waking Night surprise she would have to deal with.

Author's Note:

[Note: 7/30/17] Made some slight edits to resolve continuity issues with future chapters.

Comments

[goldfencer]

Check List, you mad genius. You have redeemed yourself.

[Frankie2]

Wow. Fleur is very crafty. I worry what Plan B was though. Now, one of them are going to Ponyville. Leaving only four. How will this play out? We will have to wait and see.