Stroke of Madness

by Ravensmith

Rating: teen
Tags: Comedy, Profanity, Random, Discord, My Little Pony: Friendship is Magic, Original Character
Length: 3890

An unusual salespony tries selling a rowboat in a desert and gets more than she bargained for.

Penny Pinch has always been considered an unusual salespony. Any other merchant would laugh at the idea of selling a rowboat in the middle of a desert, but not her.
Unfortunately, things do not go as planned, and the situation quickly spirals out of control for her thanks to a bizarre encounter...

Won first place in /mlp/'s 2nd PASTEJAM 2023. Only slightly edited to fix minor errors.

STORY RESTRICTIONS:
Write a short story set in Equestria. It must contain an unusual sales pony and the story must include a rowing boat. Also use the sentence 'Aaand she's gone overboard!'
Bonus prompt 1: The story takes place in a desert.
Bonus prompt 2: "Make a wish, then doom them all all in one go. That would be hilarious."
Hardmode: Use both prompts, the sales pony must not be an antagonist
Below restrictions are added by myself from a previous failed PasteJam.
Bonus prompt 3: As the saying goes, "A picture is worth a thousand words"
Minimum length 1000 words.
No maximum length.

Published 2023-10-17 06:20:00 UTC
Last updated 2023-10-17 06:20:00 UTC

Stroke of Madness

As Penny Pinch trudged across the desert landscape under the harsh sun, she mustered her remaining willpower to think about her situation. Only one thing came to her mind.

I made a terrible mistake trying to sell a rowboat in a desert.

"Are… are we there yet?" Coral Skip, her steadfast assistant, huffed. In spite of the fact that she had been hired for her strength, even the orange-pink earth pony would waver in these dire circumstances. Especially after dragging a heavy rowboat for hours on end. The mare was clumsily entangled with a rope attached to the rowboat, slowly moving forward as the sands grudgingly parted ways.

"Don't speak," Penny hastily muttered in response. "You can't afford to waste our water." Skip stifled the complaints on the tip of her tongue and went silent.

It might seem ridiculous at a glance, but they had a good reason to come here!

The rowboat caught Penny's eye at a yard sale in Ponyville. It was in perfect condition, yet it was being sold for a mere one bit. After interrogating the owner, she found out that the rowboat couldn't float in water. What kind of rowboat can't even float in water? Well, there was actually a very simple answer for that.

A cursed rowboat.

As an educated unicorn, Penny reached this conclusion and examined the rowboat. Although the magic seemed strangely twisted to her, she quickly confirmed her suspicions upon noticing the telltale sign of an enchantment, resulting in an immediate purchase.

When she later probed the rowboat, she discovered a charging crystal within a hidden compartment. Once it was fed magic… the rowboat started to float in the air!

It was a peculiar sight for any travelers when a hovering rowboat passed by them, Penny snoring sound asleep while Skip rowed enthusiastically. Their destination was the desert in the south.

Penny had figured the best place to sell a floating rowboat was one where the environment was open with no large obstacles. A desert fit the bill, not to mention how the ground can be a little rough to traverse. She would have preferred vast sand dunes instead of flat terrain, but the journey to such a place would not have been worth the time.

When they made it to Appleloosa, she was ready to sell it for a fine price. Unfortunately, no one took her seriously and she was laughed out of town.

Frustrated, she made Skip row them out in a random direction without checking the map. The rowboat faltered not long after, and when Penny furiously poured all of her magic into the crystal… it just broke.

Now we're stuck out in the middle of the desert. I'm so bucking stupid.

She wanted to cry, except that would make things worse. Despite having only recently been hired, Skip had been so trusting of her and seemingly ignored her egregious mistakes. Penny couldn't bear the guilt if she let her down now.

Sadly, she couldn't offer to carry the rowboat for Skip. Her magic was only good for being precise. When it came to strength, Penny failed spectacularly on all fronts.

But maybe… maybe there was something she could do. If she remembered correctly, there's a spell that gives you an eagle's eye perspective of the area from above.

Penny came to a halt. "Hang on, Skip. I'm going to try something." Looking back, she saw Skip tiredly nod in response and the nearly constant sound of sand grinding against wood stopped.

As Skip conservatively sipped from her flask, Penny started concentrating on her horn with her eyes closed. Come on, please work!

A vision from the sky slowly came into focus in her mind. She scanned their surroundings for any sign of civilization.

Just as a low whine started in her throat from the nothingness on the horizon, she noticed a dark figure. Bipedal? It clearly wasn't a pony. Nevertheless, it was still something.

Penny opened her eyes and grinned. "Skip, there's somepony — I mean, someone out there! We can get help! It'll take a while to get to them, but—"

"Looking for me? I'm flattered."

As they turned around to find the source of the deep voice, they were confronted with an incomprehensible sight. A figure towered over them, a mix of many different animals. A deer antler, goat horn, goat beard, lion arm, eagle claw… Penny had seen depictions of Discord before. Well, this creature was covered with some kind of desert garb, yet she was sure it had to be him.

Why are you here?! Penny wanted to shout, but she struggled to say anything at all. Her throat had gone dry.

As Penny and Skip stared back in shock, Discord scratched his head. "Cat got your — actually, that joke is overrated. Perhaps you'd like a free beverage, ladies?" After a few seconds to register what he said, they rapidly shook their heads up and down.

The draconequus bowed and a one-legged wooden table flashed in front of them, presenting glasses of water filled with ice cubes. The mares nervously took a glass each, but somehow the table showed no signs of toppling over.

As they chugged and water dribbled down their chins, Discord chuckled. "Drink as much as you'd like! I have incredible kidneys, so any liquid that comes out is quite clear."

When the implication hit her, Penny spat the water out and started coughing, eliciting a guffaw from Discord. On the other hoof, it obviously went over Skip's head since she gave him a cheerful grin. "Thank you so much!"

Discord glanced at Skip, but his gaze was soon drawn to the rowboat next to her and his eyes literally bulged out. "T-that's my royal rowboat!"

Penny couldn't help but raise an eyebrow. "Your… what now?"

"My royal rowboat, of course!" A visible thought bubble appeared above his head, with a vision of him rowing over a green checker-patterned land as screaming ponies ran by. He sighed with a sense of nostalgia. "Good times. I'm glad to see it in good condition."

Suddenly, Discord vanished. Penny whirled around to find him sitting in the rowboat, now donning a navy captain's outfit. He waved back. "Why, thank you for taking such good care of it, Miss…"

"Pinch. Penny Pinch."

"Yes, I should have guessed from that drab color palette," he dryly replied. "Light brown coat, dark brown mane, reddish brown eyes… it's all brown."

Her left eye twitched. "Drab? And how would you even guess brown just from my name?"

"Pennies. You know, the copper coins?" He pulled a 'penny' out from behind his ear and tossed it to her. "Keep the change."

"Oooh," Skip said as Penny caught it with magic. "I didn't know copper bits exist! I've only ever seen gold or silver ones."

Penny threw the coin behind her. "Yeah, well, that's because they don't," she growled. "Are you just gonna take off with my rowboat? I've been trying to sell this thing off for so bucking long. I don't care if you're the lord of chaos or whatever, you can't steal it even if you did previously own it. You forfeited your ownership by abandoning it."

Discord put his paw on his chest as if in shock. "Whaaat? Surely that's not true, I merely left it alone for—" He glanced down at a previously unseen watch on his left wrist. "—over one thousand years. Oh, I suppose that may have been a tad long."

As he moved to get out of the rowboat, he ducked out of sight. Once he came back up, he clambered over the side wearing an artist's beret, gripping a paintbrush and palette. "You see, I would love to pay you. Unfortunately, I am broke."

"How could you be broke?" Penny scoffed.

"I'm afraid that my art career has not been going well. Not a single person has bought any of my paintings!" Discord threw his arms up in frustration. "I simply cannot understand why when I paint such wonderful masterpieces."

"How are you going to pay me, then?" she hissed, stomping her hooves in anger.

A light bulb appeared and hit the top of his head before falling to the ground. "Ouch. Anyway, I just had the most splendid idea about how to pay you!"

With a flash of light, an easel appeared in front of him, occupied by a blank canvas. Licking his lips, he eyed it for a few seconds before furiously painting at a speed Penny had solely seen from Rainbow Dash. He was a blur, randomly rotating his entire body in nonsensical ways and dipping into different colors to finish his work.

When Penny blinked, he had already finished. He spun the easel around to show her the painting. Her first impression was that it looked good. But as she gave it a closer inspection, she found it more and more off-putting. It depicted four large ponies trotting down a dirt road in the forest, two of them wearing hats. One of them was… wearing pants, maybe? Then she noticed the missing or, worse yet, contorted legs. Although she initially thought they were just big ponies, they really didn't resemble any ponies she had ever seen.

"I don't mean to offend," Penny cautiously stated, "but uh, what kind of ponies are they? Are they perhaps from Saddle Arabia?"

"Hmm? Why, they're horses, of course!"

"Wh-whorses?" Penny stammered. "I don't see what makes them whorses…"

Discord's eyes rolled back all the way as he sighed in exasperation. "No no, HORSES, not whorses." Suddenly he gasped. "Ohhh, my mistake. I forgot to enable captions." Words sprang up in the air with a snap of his talons, showing an exact transcript of what he had said. "We're getting off track here. Is this enough payment? I dare say it may be my best piece yet."

"You can't be serious!" she sputtered in outrage. "You obviously put no effort into this, judging by the glaring mistakes. No wonder no one wants to buy your art."

"As the saying goes, a picture is worth a thousand words. I think you'll come to understand its value if I tell you a story about it." Discord reached behind his back and brought out a seemingly small piece of paper. As he held it up, it started unfolding… until the bottom was piled up on the sand below.

He cleared his throat and began a dramatic narration. "One day, Twilight Sparkle and her friends walked into the art museum. Rarity excitedly led the group, praising the exhibits on the wall as the rest of them looked confused about how a taped banana could have such groundbreaking cultural impact. As Twilight trotted along, she…"

Skip was intently listening, curious to hear more about the bearers of the Elements since she had barely ever interacted with them. Unfortunately for her, Penny was fed up with Discord's charade. "You painted it in a matter of seconds, right in front of us. It has no history."

Upon hearing her words, he froze. Then, he hurriedly scrolled through the paper to get to the bottom. "Author, author… made by chaos?!" he groaned as the paper laughed in his face and imploded on itself. "It appears that this is not my own work. Well, I have to admit that you're right about its value."

He chucked the painting away from the easel. When the painting hit the ground, the four horses galloped out and rushed towards the distant horizon. At least they tried until their limbs twisted and they collapsed.

The two mares winced at the sight, yet Discord merely shrugged. "Don't worry about them. Now, I have a proposition for you."

"Well, let's hear it then!" Penny eagerly demanded.

He wagged his finger at her. "Not so fast. First, we should go somewhere more interesting." He strutted over to the boat, plopped down, kicked his feet up on its front rim, and invitingly patted the empty seats.

Penny eyed the seats with distrust. "You realize the boat is broken, right?"

"You realize I'm the lord of chaos, right?" A wrench appeared in his paw and he leaned down, loudly twisting some metallic sounding components despite Penny never having seen anything metal inside the boat. After tossing the wrench, he gave them a wink. "Ready?"

Although they were hesitant, Penny and Skip sat down in the boat.

Discord excitedly clasped his hands. "Fantastic! Let us be off." Immediately, the boat started to float with reinvigorated magic and slowly inched forward.

Before Penny could question where they were going, the boat instantly launched itself into an upward curve with a burst of speed. Slicing through the air, it quickly gained altitude and soared to new heights for rowboat kind. If there were clouds in this desert, they would have been just above them at this point.

Skip gaped as they flew through the sky, the wind wildly blowing through her mane. "This is soooo amazing! Hahaha, weeeeeeeee!"

She wasn't the only one being loud. Penny was screaming, although she gradually dropped in volume. Skip looked around the boat for her, but just saw Discord. "Hey, where is Penny?!" she shouted.

With an annoyed tug at his ear, Discord turned off the sound of the wind so they could hear each other better. Regardless of whether he had heard the question, he peered down and laughed maniacally. "Aaand she's gone overboard!"

Penny was plummeting towards the ground at an alarming rate after falling out from the surprise launch, flailing around the air in a panic. Before she could become a pony pancake, a huge angled trampoline popped into existence beneath her. Time seemed to stop as it caught her.

Then, she was flung back towards the rowboat in the sky at an insane velocity.

Anypony who saw a speck shooting through the sky simply assumed it was a pegasus. But in reality, it was a unicorn cursing her luck for encountering the spirit of chaos in the middle of nowhere.

Before she could fly past the rowboat, Discord snatched her with a comically large baseball glove, causing her to come to a sudden stop.

He chuckled. "That was one heck of a curveball you gave me!" When silence followed, he grabbed her out of the glove and inspected her face up close. "You okay there, sport?"

Penny's tongue lolled out as she hung unconscious from Discord's claw, not answering his question.

Looking unsettled at what had just happened, Skip said, "I don't think she's okay…"

He waved at her nonchalantly in reaction to her concern. "Nonsense, she's fine! Just got a bit overexcited, that's all. Unicorn's first flight. Probably went a lot faster than Twilight did, so she gets an above average score from me." He put her down and snapped next to her ear.

As her eyes blinked open, Penny carefully looked around, pinched herself with magic, and sighed. "It wasn't a nightmare."

Discord clicked his tongue. "Oh, don't be like that. I haven't even told you about my proposition! Here it is." He held out a golden lamp towards her.

She swiftly took it from him to magically inspect the lamp, checking every nook and cranny. "What's so special about this thing?" she pondered.

When Discord slithered out of the lamp's tip, she was caught off guard and dropped it. He came out, flexing and puffing with all of his might as he grew to his original size, albeit with smoke replacing his lower half. Then, he gestured with his claw, holding up three talons.

"I shall give you—" He checked how many talons he was holding up and hastily put down two. "—one wish. You can wish for anything you want."

"Hey," Penny blurted, "what about the other two wishes? That was clearly three!"

"Look, I really shouldn't be doing this," Discord snapped. "The last time I did this for a pony, the world ended. Then he had to use his last wish to revert his other two wishes. You should be grateful that I'm even giving you one wish."

Her jaw dropped as she tried to imagine it. "So it's r-really anything?"

He yawned in reaction, simply bringing out a small cassette player and pressing a button. "You can wish for anything you want," his static-filled voice repeated back from the device.

However, it was still difficult to come up with a wish on the spot. Penny squinted at passing large rock structures in the distance as she went into deep thought. Unimaginable wealth, eternal life, power, and even ascending into alicornhood came to mind. But she could only pick one.

"That's a tough choice," she murmured.

When she looked back, the lamp was gone and Discord's legs had returned. He was lying back with shades on as he held a foil reflector in front of him. It didn't seem very comfortable with all the gaps in the seats beneath him. He noticed her gaze and slid his glasses up to meet it. "Well?" he asked impatiently.

"Just give me a bit more time to think about it." A few seconds after that, with a panicked look, she added, "That's not my wish, by the way!"

"Please," he retorted, "I know I have quite the reputation, but you offend me! Tricking you like that would be so… boring. Wasteful."

Discord's shades and reflector vanished in a white flash. He sat up straight and stretched his limbs slightly longer than they should naturally extend, giving Penny a smirk.

"If you won't make a wish, I suppose I'll have to start making suggestions." He pointed towards the distant town of Appleloosa, filled with ponies that could be mistaken for ants from this height. "Make a wish, then doom them all, all in one go. That would be hilarious."

Penny and Skip returned the smirk with horrified looks. "W-why would you even say that?!" Penny shuddered. "Aren't you supposed to be reformed?"

Discord giggled in response to their exaggerated reaction. "Come on, lighten up! They'd merely be doomed to die from a prank that even Pinkie Pie would blanch at!" When they appeared even more frightened, he suddenly coughed, "I don't mean they'd actually die, of course. Just figuratively speaking."

As they relaxed again, he drawled, "Or do I?"

Penny glared back at him and he gracefully held back another chortle. "Make your wish and the dreadful dooming won't happen," he asserted. "Easy solution, right?"

Yet she hadn't gotten any closer to deciding on the wish. Sure, she could try abusing the wish system, but she had a feeling that he wouldn't take it well. Scrunching up her face in annoyance, she turned to Skip and asked, "Do you have any ideas?"

Skip awkwardly looked away. "Even if it's silly?" she mumbled. Penny nodded.

"Well," Skip began, "I've always wanted to see what it's like to be a, uh… seapony." She blushed as Penny gave her a funny look.

Skip's shifting drew attention to her own flank, where a stylistic splash of blue droplets could be seen. "I guess I haven't mentioned it since you hired me to carry stuff, but I'm really good at moving in the water. It's like… I'm meant to be in water. But I can't stay in for very long and I can't go too deep since I'm just an earth pony."

Penny was taken aback when suddenly Skip started to cry. "I-It's so cruel!" she bawled. "There's a whole world down there in the ocean, you know. Seaquestria, they call it. But it's impossible for me to travel there by myself, and it's not like I can afford the magical enchantments to breathe underwater. That's why I'm doing odd j-jobs in the first p-place, it's s-so I can s-save up for it… I-I just w-want to g-g-gooo~…" By the end, she had turned into a blubbering mess.

"It's okay!" Penny reassured Skip with a hug as she sobbed into her coat. She wasn't expecting such a drastic change from this bubbly mare she had hardly any familiarity with. It was clear that going to Seaquestria was extremely important to her. I guess that's what happens when you get the chance to make a wish for anything, she thought.

It was a surreal situation for Penny. Despite her salespony lifestyle, she did not have an urgent goal like Skip did. Making profit off of unusual items was her passion. It might sound contradictory, but wishing for wealth would take all the fun out of having it. She wanted to earn her wealth.

She didn't exactly care for much else either. Wishing for power was purely a nonsensical thought she had toyed with. It might be accurate to say that she was aimless.

Was that wrong? Weird? She couldn't say.

However, there was a pony with an aim and a strong desire right in front of her.

Gently breaking out of the hug, Penny smiled at Skip's tear-stricken face before they briefly heard a golf clap and a claw holding a tissue box was thrusted between them.

"Tissues anypony?" Discord asked with a heavy voice, as if he had been stunned by a performance. But for once, his antics did not get to Penny as she continued smiling, and Skip snuffled before grabbing a tissue to blow her nose.

Penny turned to Discord and looked up at him, now certain of her decision, although she hesitated for a moment to ensure her wording was correct. "Discord, I wish for both me and Skip to be able to adequately breathe underwater, without restricting our current ability to breathe air."

"A rather descriptive wish, is it not?" he snorted. "But it is what I'd expect of one so experienced in making deals. Your wish is my command." With a snap, the two mares were gifted magical gills by the draconequus, although they could only tell from a new subtle feeling on the sides of their necks.

Penny looked at Skip, who was stone-still, with her eyes wide open. "Sorry," Penny apologetically said, "I kind of prefer my hind legs to a fishtail."

Skip slowly shook her head, dazed. "No… that's fine. Why both of us? I'm sure you could have squeezed in something else for yourself, right?"

Penny could only shrug. "There wasn't anything else I particularly wanted to wish for, and besides, that's a completely new region I can sell in. Imagine the opportunities and what oddities we might find there!" Her smile transformed into a grin. "And… I want to get to know you, Skip. You've been a brilliant companion, even if we never spoke much about ourselves personally in the past."

"Penny… thank you so much," Skip responded with heartfelt gratitude in her voice. "I'd be more than happy to go with you as a friend."

Discord cleared his throat. "Yes, yes, how lovely," he grumbled, "the magic of friendship and all that. Now, get off of my boat."

"Discord, could you please take us to the coast?" Penny pleaded.

"Oh, fine," he moaned. "I suppose I can give you a ride there. No more favors after that!"

The two mares cheered as he reluctantly flew the rowboat in the right direction. As they left the desert high above in the air, a hint of a smile could be seen on Discord's face.