The Terribly Taxing Tribulations of Twilight Sparkle

by Blueshift

Chapter 1: The Terribly Taxing Tribulations of Twilight Sparkle

Rainbow Dash took a deep breath and rapped on the door for a second time, clutching tight the bouquet of flowers in her hooves. This is what it had all been leading to. It was now or never.

The door creaked open, and Fluttershy slowly peeked her head out. She blinked, taking in the view of a rather smart-looking but nervous Rainbow Dash sitting on her doorstep. “O-oh, hi Rainbow Dash!” She gave a smile. “Lovely morning, you look very uh, nice today. Are those for me?” She pointed at the flowers.

“Fluttershy…” Rainbow Dash held the flowers out. “We’ve been friends for a long time, and dare I say it, maybe more…” She swallowed hard before starting again. “I love all the time I spend with you, we’ve made so many happy memories, and I feel we could make many more. Both of us. Together.”

Fluttershy’s cheeks flushed bright red and her hooves clapped to her mouth in shock. “Oh Dashie! A-are you saying?”

“Fluttershy, will you marry me?” Rainbow Dash dropped to her forehooves, pulling out a ring case and presenting it to her friend. She looked up at Fluttershy with large, open eyes. “Please, say yes!” she whispered. “It would mean so much to me!”

“Oh, Rainbow Dash, I…!” Fluttershy gave a barely suppressed squeal of delight as she reached out for the case. But then something caught her gaze. It was the calendar, pinned next to her front door. “Oh.” Her eyes narrowed, flicking between the calendar and Rainbow Dash. “March 31st. I see,” she hissed, before assertively slamming the door in Rainbow Dash’s face with one hard motion.

Rainbow Dash sat on the doorstep for a good minute, before regaining her composure. “Horseapples!” she swore to herself, pulling out her notepad and crossing off another name from the list. This was going to be tougher than she thought.


Twilight stared suspiciously at her breakfast bowl, slowly prodding the contents with her spoon. The dry, brown cereal bobbed merrily about in the milk. “Spike!” She threw up her head and yelled out in frustration. “Spike! Have you eaten all of the marshmallows in the cereal?”

“No!” Spike lied, mouth full of marshmallowy goodness. “’hy ‘ould ‘ou ‘ink ‘at?” He swallowed hard to try to destroy the evidence.

Twilight mashed the cereal with her spoon, and then slammed her breakfast utensils down. “The marshmallows are the whole point, Spike! You have to endure the throat-scraping agony of the bland, oaty cereal to be rewarded with the sweet victory of marshmallow! It’s a metaphor for life! You can’t just eat all the marshmallows straight out of the packet!”

Spike licked a claw. “I beg to differ!”

Twilight was just about to try inserting her spoon into Spike, when the doorbell rang. In retrospect, this was a relief to all involved.

“Rainbow Dash! How lovely to see you!” Twilight beamed as she opened the door, all thoughts of harming Spike for his terrible crime forgotten. “This is early in the morning for you, it’s…” She broke off to look at the clock. “Before the afternoon!”

“I know, I didn’t know there was a nine am!” Rainbow Dash flashed a smile, and from behind her back brought forwards a rather battered bouquet of flowers. “But this is important, Twilight! We’ve been friends for a long time, and dare I say it, maybe more. I love all the time I spend with you, we’ve made so many happy memories, and I feel we could make many more. Both of us. Together. Twilight, will you marry me?”

“Oh Rainbow Dash!” Twilight clapped her hooves to her mouth in shock. “I… I… I don’t know what to say!” She blushed furiously. “Well, I mean, I can’t say this is totally unexpected given how much of a catch I clearly am, but even so!” She fell to her haunches, breathing heavily. “Wow, look, this is a huge decision. Give me a few days to think about it and – ”

“No!” Rainbow Dash stepped over the threshold, face pushing into Twilight’s, eyes desperate. “No, Twilight, it’s got to be today! I’ve asked everyone else, you’re my last chance!”

Twilight’s face slowly fell as she processed her friend’s words. “You… asked everyone else?”

“Yeah!” Rainbow Dash nodded furiously. “They all said no, can you believe it! But your name was at the bottom of my list and I thought, ‘Well, Rainbow Dash, you’ve gotta try! If you throw enough mud at a wall, some will stick!’”

“You… asked me last?” Twilight started to think back to her breakfast spoon and the terrible, terrible things she could do to Rainbow Dash with it.

Rainbow Dash nodded. “Yeah, Twi, but uh… not like that! I mean I still want to marry you, you’re just last on the list, that’s all!”

Twilight slammed the door in her face.

A few moments later, Twilight hesitantly opened the door, only to change her mind and slam it shut again.

Then curiosity got the better of her, and she opened the door for a third time. “Okay, what’s going on?”

“Don’t you know?” Rainbow Dash looked about frantically, and slipped past Twilight inside the library. “It’s March 31st, Twilight! It’s the deadline for tax returns! How can you not know!” She slumped down in a chair dejectedly, burying her head in her hooves.

Twilight frowned. “Well, yes, but that’s not a big deal, as long as you obsessively track all your incomings and outgoings like I do.”

“I spent it all already!” Rainbow Dash threw back her head and wailed. “I just keep squandering all my bits on stuff! I don’t even know what half the stuff I buy is! And now it’s the deadline to make my yearly tax return and I don’t have enough to pay all my taxes.”

She shuffled about and pulled out a battered-looking official green form. “But it turns out there’s a twenty percent discount for married couples! If I was married, I wouldn’t need to pay as much tax, and I could afford that and not go to jail or the moon or whatever they do to debtors nowadays!” She winked at Twilight. “And you’d be covered for twenty percent off too, Twilight! Bless the Equestrian government and their promotion of tax breaks for marriage! C’mon! What do you say?”

“No!” Twilight yelped out, surprising even herself with the force of her words. “Rainbow Dash, I am surprised and disappointed! Marriage is a sacred institution and shouldn’t be used just for tax purposes! You have to learn to be responsible – that tax money goes towards schooling and healthcare, you can’t just cheat the government out of it! Celestia would be so mad with you if she found out!”

Rainbow Dash sniffed back a tear, scrunched up her nose and reached for the opened box of cereal that sat on the table besides her. “Hey, there’s some marshmallows in here,” she mumbled, scooping out the remaining marshmallows from the packet and stuffing them in her mouth.

“Out!” Twilight pointed a hoof to the door.

“But Twilight!” Rainbow Dash finished chomping down her impromptu breakfast and looked at Twilight with the most pathetic, needy look she could come up with. “You’ve gotta help me! Maybe there’s some other tax avoidance scheme you could help me – ”

“No!” Twilight flushed with anger. “Rainbow Dash, I am not going to be party to any tax scams! You should be so ashamed of yourself! You don’t see anyone else sneaking about trying to cheat the Equestrian state! For shame!”

Twilight herded Rainbow Dash out the door to a chorus of "But's" before slamming it one last time. She shook her head in a huff and patted the neatly sorted box of receipts that sat on the dining table.

“That Rainbow Dash,” she sighed to Spike, picking up her spoon and beginning the arduous task of eating her marshmallowless breakfast. “She’s one of a kind!”


“Mornin’ Twilight!” Applejack doffed her hat as Twilight passed her in the Ponyville town square. It was market day, and traders of all shapes and sizes had set up their stalls to peddle their wares. Applejack’s cheerily homemade stall was covered with apples and apple-related products of all shapes and sizes. It was, in fact, impossible to comprehend the variety of produce that Applejack had managed to extract from the humble apple.

“Hi, Applejack!” Twilight trotted up to her friend, her side satchel bursting with precious boxes of breakfast cereal that proudly stated ‘EXTRA MARSHMALLOWS’ on the front. “Lovely day!” She looked over Applejack’s wares and gave a whistle. “You look like you’re doing well!”

“Ah, not really!” Applejack shrugged, and then broke off to quickly deal with a customer who was purchasing a cartload of apples. She stashed away her newly-gained bits and turned to Twilight. “Business is real poor, Twilight. Ah think we might be homeless if we get another bad harvest like this.”

“Oh, Applejack!” Twilight rolled her eyes in amusement. “I don’t understand how the most successful apple orchard in Equestrian history is constantly on the bread line. Maybe you need some accounting help. I could – ”

“No! It’s fine!” Applejack cut across Twilight sharply. “Ah take care of the books, Twilight. It’s just that we’re not gettin’ in much cash at all. We’re always totally broke!”

“Excuse me, Applejack.” Filthy Rich popped his head into the scene. “Have you got this month’s supply of fifty apple cider barrels? It’s just that Gumballs said he could pick them up today if you do, and –”

“Yup!” Applejack nodded. “Jus’ tell him to drive down the back of the orchard, Big Mac’ll load em up. Usual arrangements?”

“Of course. We’ll pay in cash.” Filthy Rich tapped his nose.

Twilight looked at Filthy Rich, then back to Applejack, a puzzled look crossing her face. “Well, there you go, if Filthy Rich is buying your apple cider in bulk then you’ve got a huge income! You’re saved, Applejack.”

Applejack stared at Twilight blankly. “Ah don’t know what you mean,” she stated back slowly. “Ain’t no money to be made apple farmin’, Twilight. Our orchard makes a loss each month.” She scrabbled around under her stall, and emerged with a green form and a quill. “Actually, while you’re here, could you jus’ sign this for me? Ah need an upstandin’ member of society to corroborate the fact that the Apple family are destitute. Jus’ paperwork, you understand?”

Twilight took the form and read over it carefully. “But Applejack!” she exclaimed after she finished reading the fine print in detail. “This form says that I have personally checked over all your accounts and take liability for them!”

“It’s jus’ words, Twilight!” Applejack groans in frustration. “Sign the form, y’all know how poor we are.” She broke away again as Bon-Bon approached to buy her usual five cases of apple chutney.

Twilight glared at Applejack suspiciously. “Applejack, if I didn’t know better, I’d say you were lying about your income to the tax pony to avoid paying tax! But…” She dropped the piece of paper, face screwed up as conflicted emotions flitted about her. “But you can’t be, because that would be lying and you’re the Element of Honesty so you can’t be!” She looked at Applejack, who had just taken another fifty bits and was hiding them under the stall. “But you’re clearly raking it in!”

“It ain’t like that!” Applejack huffed impatiently. “It’s mah money fair an’ square! An’ it aint a lie that we’re poor, ‘cos in comparison to Princess Celestia we are poor! So don’t go accusin’ me of bein’ a liar!”

“You can’t lie to the government about your income!” Twilight screwed up Applejack’s piece of paper and stomped it into the ground. Then she had a small pang of guilt, and carefully unwrapped and smoothed it down, before handing it back to Applejack. “Taxes pay for the fire service! And public building work! How are the roads going to be fixed if there’s no money?”

“Everyone does it, Twilight!” Applejack looked at the paper in annoyance. “Ah shucks, ah’ll just get Carrot Top to sign it.”

“Everyone does not do ‘it’, Applejack!” Twilight’s face flashed red with anger. “And you can’t just rope me into a… a… tax avoidance scam! What would Princess Celestia say? She’d be furious!”

“Hey, Carrot Top, come sign this!” Applejack waved the crumpled paper in the direction of the next stall along. Carrot Top waved back and trotted over.

“She’s not going to sign that!” Twilight pouted. “No-one’s going to lie on an official document, Applejack! It’s dishonest!”

Carrot Top barely glanced over the document as she signed it with a flourish. “Sure thing Applejack!” She smiled at her fellow market trader. “You should do what I do. All my fields are rented from Carrot Top Incorporated, which is based in Aquantis, the Sea Pony tax haven. The rent matches my profits, so it all gets paid there and counted as outgoings, perfectly legal. I pay no tax as I don’t make any money. Then the president of Carrot Top Incorporated collects her tax-free profit from her office in Aquantis.” She tapped her nose. After a short pause, she added: “I’m the president of Carrot Top Incorporated.”

“Oh!” Applejack’s mouth fell open. “That’s mighty crafty, Carrot Top! That sounds like a great idea!”

“No it doesn’t!” Twilight squeaked in frustration. “That’s illegal!”

“It’s not illegal!” Carrot Top smirked and slipped back to her own stall. “It’s a loophole, completely different! If they didn’t want ponies to do that, they’d make it illegal!”

Twilight ground her hooves into the grass, trying as hard as she could to not snap out in anger. “I would have thought better of you two!” she hissed between clenched teeth.

“Oh, Twilight, don’t let Applejack wind you up.”

Twilight turned to find Rarity standing next to her. “Rarity!” she exclaimed in relief. “Did you know what Applejack is doing? She’s trying to cheat the tax pony!”

“I know!” Rarity flicked back her mane in a show of contempt. “Awful business, Twilight! If you can’t find honesty in the literal embodiment of honesty, where can you find it?”

Twilight bit her lip. Already she was running through the scenario in her mind where she reported Applejack to Princess Celestia. Would the princess stop at stripping Applejack of her Element? Or would Applejack be thrown in prison forever as well? She came to a decision. “You’ve still got the rest of the day to amend your tax return!” she announced to Applejack. “If you do that, I won’t tell anyone what you tried to do, not even Princess Celestia! Please, Applejack. Look at Rarity and me for a good example, we both pay taxes like everyo – ”

“What?” Rarity pulled a face. “I don’t pay taxes, Twilight.”

“Yeah!” Applejack looked at Twilight like she had gone crazy. “Rarity don’t pay taxes, what the hay are you talkin’ about?”

“But…” Twilight furrowed her brow. “Rarity, you have a dress design business! You sell dresses all over Equestria!”

“Oh, Twilight!” Rarity gave a tinkling laugh. “That’s not a business, it’s a hobby! It doesn’t count!”

“It’s still income!” Twilight snapped back, getting more and more concerned that she had fallen into some strange parallel universe where she was the only reasonable pony left. “Any income over ten thousand bits a year has to be declared and taxes paid! And you make more than that, because that last dress you sold to Duke Midnight cost well over ten thousand bits alone!”

“But it’s not a business, it’s my little hobby!” Rarity exclaimed as if talking to a very small foal. “It’s just a fun thing I do to pass the time. I don’t have an office or anything, it’s just me in my house.”

“It’s a dress shop!” Twilight snapped back. “It’s not a house, it’s a dress shop!”

“It’s not a crime to decorate your house with dresses!” Rarity gave an exaggerated roll of her eyes to Applejack. Applejack shrugged in response and tapped her head with her hoof.

Twilight sunk to the ground with a whimper.


Rainbow Dash kicked a can along the street, muttering to herself. The day had not gone as planned. Silently, she cursed the fact that she had tried to start her scheme at the last minute. Perhaps if she had bought Fluttershy a dinner or two earlier in the year, that might have made her more agreeable. It was too late now. If she couldn’t get married, she had half a day to come up with the rest of the money. There was no-one left to ask, and –

She looked up from the ground, eyes falling on a stallion she had never seen before. A slow smile crept across her face as she sauntered up to her new target, fluttering her eyelashes. “Hey there,” she said in her most disarmingly sultry voice. “I know we’ve only just met, but I believe in love at first sight. Let’s get married!”

The stallion slowly turned towards her. He struck Rainbow Dash as a very grey pony. Very grey indeed. And oddly familiar. She paused. “Do I know you?”

“Maybe,” he muttered, raising an eyebrow. “My name’s Past Dues. I’m the tax auditor. What was that you asked me?”

“OH HORSEAPPLES!” Rainbow Dash screamed in his face, turning tail and running as fast as she could.


“For the last time,” Twilight stood in the middle of the market place, shaking her head at Pinkie Pie. “You have a job. I’ve seen you! You work at Sugarcube Corner! You’ve got to pay tax on your earnings!”

“Nope!” Pinkie Pie shook her head again, a stupid grin plastered on her face. “Silly Twilight! I work for the Cakes for free! In return they give me free lodgings and food, and give me money from a set budget for all the things I want to buy!”

But that’s the same as having an income!” Twilight hissed, barely restraining herself from lunging at Pinkie Pie and smacking her round the head. “How can you not see that?”

“Twilight, leave her alone,” Applejack called from her apple stall whilst selling a crate of apple tarts to Lyra. “She said she ain’t got a job!”

“Yes, Twilight.” Rarity patted Pinkie Pie on the shoulder. “Didn’t you hear her? Now just sign her form as an official witness.”

“I did hear her! Did you?!” Twilight looked about in frustration, to be met only with blank stares from the crowd that had begun to surround her. “I’m not signing any form to claim Pinkie Pie is unemployed when she clearly isn’t! Don’t ask me to abuse my position as student of Princess Celestia and lie to the tax pony for you!”

“It’s not lying!” Pinkie Pie exclaimed. “It’s true!”

“Technicalities!” Twilight cast about for anyone to come to her aid. No-one did. “Princess Celestia believes strongly in ponies helping each other and doing their duty, and that includes taxes! She would be ashamed of you all! I am not getting roped into any of your scams! Furthermore – ”

“HE’S HERE! HE’S HERE!” Rainbow Dash raced through the market like an omen of doom, wild eyes staring ahead as she ran as fast as she could. “THE TAX PONY’S HERE!”

The ponies gathered in the marketplace started to scatter as they heard Rainbow Dash’s words. One or two of them screamed. Distantly, Twilight could hear Bon-Bon shouting “Lyra! Burn everything!”

A grey pony in a grey suit trotted up to Twilight, casting a withering look all around at the fleeing ponies. “I had thought,” Past Dues began, “that I could make a start a bit early, if any pony was actually ready with their tax return. But it seems not.”

Twilight puffed her chest out in pride. “I guess it is my turn once more to be a moral exemplar!”


“Curse it! Curse it!” Rainbow Dash skidded round the corner of the town hall and came to a screeching halt, cowering behind a stairwell. She wiped the sweat that had begun to bead on her forehead. “C’mon Dash, you’ve been in tougher situations than this!” she whispered to herself. “There’s gotta be something you can do!” She took out her green tax return form again and stared at it, as if willing it to transform into something more reasonable.

She looked up from the form to meet the gaze of a pair of tiny eyes.

“Beat it kid,” Rainbow Dash muttered at Scootaloo. Scootaloo just sat still, unmoving in front of her. “I said, beat it.”

“Uh…” Scootaloo raised a hoof. “I uh, heard you were going around uh, asking ponies stuff?”

Rainbow Dash sighed heavily. “Yeah, but no. Don’t be silly, Scootaloo. Besides, you’re too you – . Wait, how old are you?”

Scootaloo thought about this for a moment. “Six!” she eventually ventured.

“Yeah. Not gonna happen.” Rainbow Dash looked at her tax form again, desperately trying to find any loophole. Then a thought struck her. She slowly put down the piece of paper to fix her gaze on Scootaloo, a friendly smile creeping across her face. “Say, kid, here’s an idea…”


Twilight’s library had been turned into an impromptu tax inspection office. A line of ponies stretched out the door, all of them looking extremely nervous and sweating profusely. All of them, that is, apart from Twilight, who stood next to Past Dues looking extremely pleased with herself.

“That’s all in order, Ms Sparkle!” Past Dues stamped Twilight’s form with a flourish. “I have never seen such an exhaustively sourced tax return in all my life.”

“Wow.” Applejack stood grimly at the front of the queue. For some reason she was now wearing a burlap sack with holes cut in it and mud smeared over her face. Her hat was replaced with a special substitute made entirely out of old cardboard. “You got totally done over, Twilight!”

Twilight shook her head. “Just paying my dues, Applejack, like any honest pony.” She glared at her friend, leaning in closer. “There’s still time to do the right thing!”

“Coming through! Coming through!” A commotion at the back of the queue erupted, as an extremely smug looking Rainbow Dash and Scootaloo pushed their way through to the front. Rainbow Dash presented her form with a flourish to Past Dues. “All here, present and correct!” she smirked, producing an official looking form and passing it over. “I’d like my twenty percent discount please!”

“What!” Twilight looked between Rainbow Dash and Scootaloo. Scootaloo sat beside Rainbow Dash, wagging her tail like a little dog, barely able to contain her excitement. “Rainbow Dash! What have you done?”

Past Dues checked the form over, and quickly scribbled a note with his quill. Then he took out his stamp and thumped it onto the paper. “Yes, that seems all present and correct, Ms Dash.”

What?” Twilight exclaimed again in disbelief.

Rainbow Dash rubbed her forehooves together in victory. “Oh yes. There’s also a twenty percent discount for dependants! Twilight, meet Scootaloo, my new legally adopted daughter!”

“Yay!” Scootaloo cried out, tears of joy running down her face.

What?” was all Twilight could muster.

Rainbow Dash stifled a yawn. “Well, that’s me done! Time to get home for some well-earned rest I think!”

“Yay!” Scootaloo cried again, grabbing on to Rainbow Dash’s back leg. “Let’s go home, mommy! I’m so glad I don’t need to sleep in a cardboard box in the Cutie Mark Crusader clubhouse any more!”

Rainbow Dash’s face paled as she started to desperately try and shake Scootaloo off. “Wait. No. Wait!”

“I’m so happy!” Scootaloo wept. “We’ll be together forever and ever, just me and my new mommy!”

“Oh flipping hell!” Rainbow Dash hobbled out of the library, with Scootaloo attached fast.

Twilight turned back to Applejack and the other assembled ponies. “Well, I guess we’ve sort of learnt a valuable lesson about contract law,” she began. “You see, when…”


Twilight’s speech ground to a halt as the ethereal voice of Celestia cut through the air. “P-princess?” she gasped, looking around her in confusion. The air started to shimmer, sparks of light surrounding her as she felt a wave of magical energy lift her up.

“Twilight! My most faithful pupil!” Celestia appeared in a blinding flash of light, a warm smile permeating her face. “I have watched your trials and tribulations today. Out of all ponies you have proven yourself to be the most honest and diligent of all!”

“Yes! Yes I have! Thank you Princess!” Twilight’s heart almost burst with pride at this praise. Wisps of magic curled around her as she was caught in the mysterious aura.

“This was your last test, Twilight,” Celestia continued. “The final temptation! You have avoided all opportunities to cheat the system despite their legal grey areas! You have shown that you are indeed worthy of the love and trust we all put in you! Worthy to finally ascend!”

Twilight’s mouth dropped open in utter shock. “Y-you mean…”

“Yes, Twilight!” Celestia spread wide her wings. “It is finally time! Do you accept the gift? The gift of princesshood?”

“I do! I do!” Twilight cried in sheer delight. As she spoke, the waves of energy washed over her and she felt a new power growing inside her, glorious purple wings bursting forth from her sides. The magic gently deposited her back on the ground amidst the cheering of all the ponies in the tax queue. “This… this is the happiest day of my life!” Twilight sniffed, a tear trickling down her cheek. “I knew you believed in me, Celestia! I knew my destiny lay in princesshood, but I never dared believe…”

Celestia smiled warmly at Twilight, and then turned around to Past Dues, presenting a green form. “I think you’ll find everything is present and correct,” she purred, pointing at Twilight. “And, of course, a twenty percent discount for princess dependants.”

Past Dues looked at Twilight, then back to the form and gave it his stamp of approval. “Very good, ma’am,” he grunted.

“What?” Twilight yelled, her new-found wings curling in sheer shock and betrayal. “W-what?”

“Oh come on!” Celestia rolled her eyes and pointed at the long queue out the door. “It’s a loophole, Twilight. Everyone’s doing it!”

Author's Notes:

Thanks to Nicknack for editing help, and Noble Cause for coming up with the name for a tax pony!

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