The Many Adventures of the Grim Reaper

by Vertigo22

Rating: teen
Tags: Death, Princess Luna, My Little Pony: Friendship is Magic, Dark, Comedy, Other, Princess Celestia, Slice of Life
Length: 4055

A series of one shots revolving around the continuing adventures of the Grim Reaper as he learns the meaning of friendship.

Cover art by CaioCola and Steadfast Hoof. Thank you both so much.

After a successful letter to Canterlot Middle School, an even more successful Q&A at Ponyville Elementary, and a not-so successful speech at Canterlot Brewery, the Grim Reaper is now set for even more friendship lessons!

Written more as a collection for future installments in my Grim Reaper series, rather than to tell a straightforward story.

Published 2016-10-31 15:40:01 UTC
Last updated 2016-10-31 15:40:01 UTC

The Grim Reaper Goes Trick or Treating

Nightmare Night. A night when foals dress up and go door to door to get candy (and cavities).

However, Nightmare Night isn't restricted to just foals. Teenagers, and even adults, go trick or treating.

As do millennia old embodiments of sad facts of life.

“Celestia, I don't see how this is going to help me learn the values of friendship,” the Grim Reaper said as looked in a mirror. Around his cloak was a plastic pumpkin container. “Unless my lesson is to collect the wrappers from candy, I'm pretty sure I'm just going to look really goofy.”

“Oh, Grimmy, this isn't a friendship lesson!” Celestia said as she levitated a pom-pom onto her left wing. “I just wanted to have you go trick or treating this year!”

“Celestia, I go trick or treating every day,” the Reaper retorted. “I call it my job.”

Celestia sighed and levitated a pom-pom onto her right wing. “Grimmy, just go trick or treating this year, and I promise I won't ever bug you about another holiday ever again!”

“Celly, you told me that same thing about Easter egg hunting,” the Reaper replied, a hint of irritation in his voice. “Along with Hearths Warming Eve Carol's, Hearts and Hooves Day card making, and—for whatever inexplicable reason—New Year's resolution making, which neither of us ever kept those resolutions!”

“Pwease?” Celestia asked with doleful eyes.

“No,” the Reaper deadpanned.

“Pretty pwease?”

“You aren't going to stop asking, are you?” the Reaper asked, frustrated.

“Nope!”

“Fine, I'll go trick or treating,” the Reaper said. “But I refuse to be accompanied by anyone. I'm doing this myself.”

“Fine by me!” Celestia exclaimed. “By the way, what do you think of my costume?” she asked as she flared her wings. “I'm going as a cheerleader!”

The Reaper looked at Celestia, who wore a sports jersey, had two pom-poms on her wings, and yellow face paint. “Why exactly are you going as a cheerleader?” he asked “I thought this holiday was about being scary, not looking like the thing that I could only describe as a clown that got fused with an alarm clock.”

Celestia frowned. “Well, I've never been one for dressing up as something scary, and I didn't want to go as a butterfly this year,” she said sheepishly. “You don't think it looks bad, do you?”

“I, honestly, don't know,” the Reaper said. “I do, however, think you look like a lemon with that face paint.”

Celestia sighed. “Fine, I’ll go ask-” Before she could finish that sentence, the throne room door swung open, and Princess Luna—who was dressed as a astronaut—ran in.

“Sister!” Luna exclaimed excitedly. “Your costume looks terrific!” She looked at the Grim Reaper, who simply looked up at the princess of the night. “Hey, Grimmy!”

“Hello,” the Reaper replied. “I'm guessing you're also excited to go rot your teeth out eating candy?”

Luna nodded happily. “Well, I doubt I'll rot my teeth out. I won't eat it all at once!”

“Sure you won't,” the Reaper said to himself. “Anyways, I'll leave you two to discuss whatever it is you wish to discuss,” he said. “I guess I'll begin my night of collecting stuff that I'll never eat.”

“Don't forget to use that spell I gave you!” Celestia said as she and Luna saved to the Reaper.

“Yeah, yeah,” the Reaper replied as he walked out the throne room door. A few guards jumped at the sight of the Reaper, but quickly calmed down and waved to him—to which the Reaper waved back before he continued towards the castle entrance.

After a short walk, he arrived at the front door and exited the castle. Outside, dozens upon dozens of ponies were out trick or treating. “What a variety of costumes,” the Reaper said to himself. “And here I am wearing my normal attire, and a plastic pumpkin bag around my neck.” He let out a sigh and walked down the steps and towards the rural part of Canterlot.

After a short walk, the Reaper arrived at street where dozens of foals were dressed up in a variety of colorful costumes. “Well, I foresee a lot of diabetics,” he mused to himself. He walled down the street and up to a young earth pony mare with an amethyst coat, who shivered as he neared her.

“Geez,” she said as she looked up at the Reaper. “Did it just get really cold? Or is just me?”

“No, that's just my radiant personality,” the Reaper replied. “Also, uh… trick or treat?”

The mare grabbed a chocolate bar and raised an eyebrow. “Are your hooves… bones?” she asked as she handed the Reaper the chocolate bar.

“Yep,” the Reaper said. “They have been since I was born.”

The mare chuckled. “You're really embracing your character,” she said. “I'm glad to see you're enjoying Nightmare Night, even at your age.”

“Gee, thanks,” the Reaper grumbled. “Happy Nightmare Night, Lucy.”

Lucy's eyes shot open. “H-how do you know my name?”

With a snicker, the Reaper walked away, leaving Lucy with an unnerved expression on her face. He walked across the street and walked past a few foals, who all shivered. I liked it better when ponies didn't acknowledge the cold aura, he thought as he trotted up to the front door. He knocked on it and watched as the wood deteriorated away. “Uh…” The Reaper looked around, and saw a few foals behind him, their mouths agape. “Termites did it.”

The foals screamed and ran away.

“I need to work on my diplomacy,” the Reaper said to himself. He turned around and looked up at a stallion with a ghoulish mask. Its eyes were blood red, and had razor sharp teeth. “Oh, hey,” the Reaper said casually. “Trick or treat.”

“I pick trick!” the stallion declared. “Pull a trick for the ages, and you'll get your candy!”

“Uhh…” The Reaper levitated over a nearby Jack-o-Lantern and placed it in front of himself. “Here you go,” he said as he kicked it over.

The stallion looked down at the fermented pumpkin. “That was my foals,” he said as he looked back up at the Reaper. “How'd you do that?”

“Magic,” the Reaper deadpanned. “Now, can I get my candy? If I wanted to answer questions, I would've become a politician.”

The stallion handed the Reaper a lollipop. “You don't have to be so pushy,” he said. “Part of the fun of Nightmare Night is enjoying the scares!”

“I know,” the Reaper said as he turned around. “By the way, tell your foal that I'd give the Jack-o-Lantern a six.” With that, the Reaper walked towards the house next door. “Huh, wonder the lights are off.” He trotted up and levitated a rock up before he knocked it on the door.

A teenage unicorn filly answered the door. “No, we don't have any candy!” she snapped. “Also, your costume sucks!”

“I see your holiday spirit is as terrific as your personality,” the Reaper said. “I'll be sure to visit you on Hearth's Warming Eve for a dose of joy and happiness.”

“Screw you!” the filly snapped, a scowl on her face.

“If I had a bit for every time I heard that, I could buy you a lifetime supply of happy pills.”

The filly slammed the door and locked it.

“Happy Nightmare Night!” the Reaper yelled before he walked away. He trotted down to the sidewalk and looked up the block. “Ah, geez,” he said as he noticed the numerous houses that lined the street. “This is going to be a nightmare.”

“Oh, come on,” a passing earth pony stallion dressed up as a royal guardsman said with his foal, who was dressed up as a knight. “We've been to at least forty houses! How many have you been to?”

“Three houses,” the Reaper answered. “Although, I didn't get candy from one because the filly inside has the holiday spirit of a roach.”

“That's it?” the stallion asked. “How on Equus are you already exhausted?”

“I’m not exhausted,” the Reaper snarled. “I'm not used to this kind of thing.”

“What do you mean?” the father asked.

“Well, my job involves a lot of… going to places where heartbreaking things have occurred,” the Reaper said. “And if you'd like to not see me showcase that talent, you'll go get your son, because he's about to blindly run across the street.”

“What!?” The stallion looked around before he saw his son getting ready to run. “Shield Carrier, don't you dare!”

The Reaper watched as the father scolded his son before he walked to the next house with its lights on. Curse my inability to lie, he thought as he walked up to a cyan colored house. It’d be so nice to not have to explain to ponies that I'm death itself. Maybe I can somehow convince them I'm actually Cupid.

The Reaper levitated another rock over and knocked it on the door. He tossed it aside as a silver coated unicorn colt answered the door with a large smile. “Ah, what joy!” he said in an overly excited tone of voice. “I do love trick or treaters! The costumes are so creative and cool!”

The Reaper shook his head. “I can't tell if you're being sarcastic” he said, “or if you're the single most upbeat pony I've ever met in my entire life.”

“There’s nothing wrong with being positive,” the colt said. “It’d make the world a much better place if we were-”

“Listen, I just want the candy,” the Reaper growled. “Not a lecture. I get that enough from Celestia.”

The colts eyes lit up. “You know the princesses!?” he asked in an overly excitable voice.

The Reaper groaned. “Yes,” he said. “Now, candy. Please. I don't wish to be here any longer-”

The colt threw a candy bar at the Reaper, which struck him in the face. “I need to tell all of my friends I met someone who knows the princesses personally!” he said as he shut the door.

The Reaper levitated the bar into his bag and walked back down to the sidewalk. He looked up the block again and groaned. “Awesome. Another nineteen houses,” he said before he walked across the street and trotted up to a peach colored house, where an elderly earth pony mare was handing out candy.

“Why hello there, sonny!” the mare said. “My, you look just my husband. He loved Nightmare Night.”

“Uh, that's… that's very fascinating,” the Reaper said as the mate continued to drone on. “Also, trick or treat.”

“And he'd always hand out candy apples to the foals.”

“Are you going to continue to just ramble?”

“What's that?” the mare asked. “I lost my hearing aid last month.*

The Reaper pointed to the candy bowl, and then to the bag around his neck. “Candy. The stuff that makes dentists say ‘I told you so’. Can I have some?”

The mare stared blankly for a bit before she said, “Oh! Yes, of course, sonny!” She landed a few pieces of taffy to the Reaper. “Take care now!”

The Reaper shook his head as he walked away. I'm ninety-nine percent sure that I'll be visiting her in a week's time, he thought as he walked next door. “Well, someone takes Nightmare Night seriously,” he said.

The maroon colored house had numerous orange lights outside of it, and a large, inflatable Nightmare Moon near the porch.

The Reaper waited by a nearby bush as he waited for a family to get down from the porch, where a unicorn colt and pegasus filly were handing out candy together. As he waited, a pegasus foal with a beige coat—and wearing a Grim Reaper costume—ran up to him. “Wow, mister!” he said. “That’s a great costume!”

The Reaper turned his attention from the decorations to the foal. “Uh, it's not a costume, kid,” he replied. “I'm the real deal.”

The foal laughed. “You're funny!” he said with a smile. “What do you think of mine?”

The Reaper remained silent for a few seconds as he looked over the cloak and plastic scythe. “I give it an eight,” he said. “Your cloak’s a bit too pristine.”

The foal cheered as his mother walked up to him. “Aviate, I told you not to go ahead of me!” she said. She turned her attention to the Reaper and smiled. “I'm sorry. He's got too much energy for his own good.”

“Yeah, and he's out collecting food that's full of something that makes ponies get a burst of energy,” the Reaper said. “Good luck with that!” he yelled as he walked up to the colt and filly.

“Hey, Candle,” the filly said. “Isn’t this the fifth adult trick or treater tonight?”

“Yep!” Candle said. “Five more, and we’ll win that bet, Sweet!”

“What do you get out of that bet?” the Reaper asked. “Fifty bits?”

“Nope!” Candle said as he levitated a chocolate bar into the Reaper’s bag. “Candy!”

The Reaper remained silent for several seconds before he finally asked, “Why?”

“Why not?” Sweet asked. “It’s candy!”

“If you're handing out candy right now, why make a bet to win some when you could've just as easily eaten some tight now?” the Reaper asked.

“Because bets are fun,” Candle said. “You don't seem to be very fun.”

“Well, you're right to assume that,” the Reaper said before he trotted away. I swear, I'm going to get back at Celestia for this damn night. He walked across the street to a dimly lit house and walked up to the door.

“Boo!” an earth pony colt with a monster mask said as he leaped out from the nearby bushes.

The Reaper turned around. “Oh, hey,” he said. “Trick or treat.”

The colt took off the mask and frowned. “I didn't scare you?” he asked, disappointed.

“No.”

“Not even a little?”

“No.”

“Not even a teensy bit?”

“Kid, I'm more afraid of my tax returns.”

The colt sighed and grabbed a piece of candy. He tossed it over to the Reaper and grabbed his mask. “Happy Nightmare Night,” he said before he put his mask back on and went back into the bushes.

“Hey, not for nothing, but I'm pretty sure that most ponies know you're in there,” the Reaper said as he levitated the piece of candy into his bag. “Just saying,” he said as he walked towards the house next door when he was met with a horrifying sight.

“Grimmy!”

“I knew I should've brought vodka when I agreed to do this.”

Princess Celestia and Princess Luna both ran flew over to the Reaper, who simply sighed. “How's your trick or treating going?” Celestia asked.

“Uhh… I've gone to seven in total,” the Reaper said. “It’s been a life altering experience.”

Celestia raised an eyebrow. “How so?”

“I've learned that nobody will believe you when you say you're the actual Grim Reaper,” the Reaper replied. “I've also learned that this is really boring—and that I'd love it if I could stop.”

“Aw, come on, Grimmy!” Luna chimed in. She levitated over a large bag full of candy. “This is awesome! Look! I got a ton of candy!”

The Reaper looked in the bag. “I see a stomachache and one very rich dentist in there,” he said. “And several very angry maids.”

Luna levitated the bag back and frowned. “Stop assuming I'm going to gorge on it all tonight,” she said with a look of indignation. “I learned my lesson last year.”

“Calm down, Lulu,” Celestia said. “Now, Grimmy, just go to three more houses. Pwease?” she asked with beady eyes.

“Fine,” the Reaper replied. “But you're keeping the candy I get.”

The two princesses looked at each other, and then back at the Reaper. “Why?” Celestia asked.

“I don't want it.”

The duo looked at each other again and smiled. “Woo-hoo! More candy!” Luna exclaimed.

“Well, see you two later,” the Reaper said with a chuckle as he walked next door and up to the pegasus stallion who was handing out candy.

“Hello there, bud,” the stallion said. “Happy Nightmare Night.”

“Yes, happy Nightmare Night,” the Reaper said. “Trick or treat and all that other stuff.”

The pegasus handed the Reaper and a large lollipop and smiled. “I made them myself!”

“I'm pretty sure this thing is the size of a frying pan,” the Reaper said. “What in the world were you trying to accomplish when you made this?”

“It's an old family recipe,” the stallion said. “We used to sell them in Cloudsdale!”

“I’m going to imagine that, at some point in time, someone used this to clip another pony's wings.”

The pegasus looked at the ground. “That's why we stopped selling them.”

“Next time, don't make it large enough to be a child's battleaxe,” the Reaper said. “Maybe try a mirror.”

“Will do!” the stallion said with a sudden smile.

“I wasn't serious.”

“I am though!”

“Great, I'm going to be indirectly responsible for somepony trying to do makeup while walking with a lollipop for a mirror,” the Reaper said. “I hate myself some days.”

“Don't worry, bud!” the stallion said. “Just focus on the positive aspects of life!”

“Okay, I'm going to just go now,” the Reaper said as he walked towards the house across the street. He trotted up to the front door and levitated a rock over to himself before he knocked on it.

“Uh, hi,” a green coated earth pony mare said. “You out trick or treating?”

“Yes,” the Reaper answered.

“One moment.” The mare walked away and returned with a candy apple. “Here you go.”

The Reaper looked down at the apple. “Well, that's something I didn't expect,” he said. “Thank you.”

The mare nodded and closed the door as the Reaper walked next door to an extravagantly decorated house—complete with moving Nightmare Moon animatronics and enough lights to cover Celestia's castle.

“Someone either has too much time on their hands, or has a cutie mark in decoration,” the Reaper said to himself as he admired the various decorations. He walked up to a unicorn stallion and said, “Impressive work.”

“This is nothing,” the stallion said. “You should see inside!”

The Reaper remained silent before he finally said, “You have a real dead pony in there, don't you?”

The stallion laughed. “No, but I'm pretty sure there are real tarantulas in there!”

“Yeah, I'll pass,” the Reaper replied. “Can I have some candy though?”

“Only if you make it through the house!”

The Reaper promptly walked towards the house across the street. I haven't got time for haunted houses, he thought to himself. I see enough ghosts when I do my job. He trotted up to a yellow coated earth pony filly. “Trick or treat.”

“You look like somepony I saw in a dream last night,” the filly said as she handed the Reaper a piece of candy. “Only, he was shorter, and much more muscular.”

“Fascinating,” the Reaper replied. “I'm sure that's a story for the ages.”

“Well, I thought it was good,” the filly said.

The Reaper shook his head. “How exactly do you even know what I look like?”

“Well, the stallion in my dream was a mysterious cloaked figure,” the filly said. “And he saved me from an evil dragon.”

“Did he have bone hooves?”

The filly looked down. “Hm… I don't think so,” she said. “Maybe!”

“Welp, I'm going to go before it turns out I'm that pony,” the Reaper said as he speed walked towards the house across the street. He trotted up to a pegasus mare and foal at the top of the steps and said, “Trick or treat.”

“Mommy, he's scary,” the foal said, fear filling her voice.

“Kid, I scare a lot of ponies,” the Reaper said. “Except for ponies who drink tabloid journalists.”

The mare let out a nervous chuckle. “He’s joking, dear,” she said as she quickly handed the Reaper a candy bar. “Right?” she asked with a glare.

“Nope,” the Reaper answered as he walked away, and began his walk back towards the castle.

After a bit of walking, the Reaper stopped and leaned up against a wall. “Okay, I've got a whooping ten pieces of candy,” he said as he looked down at his bag. “I can't wait to see the look on their faces.” The Reaper chuckled to himself, but then noticed a few colts near a statue.

“Okay, let's egg it!” an earth pony with a grey coat said.

“No, let's TP it!” a unicorn colt with a red coat said.

“No,you idiots!” a third earth pony—this one with a purple coat—said. “Let's do both!”

“Uh, excuse me,” the Reaper said as he approached the trio. “I can't help but notice you wish to screw with a monument dedicated to Shining Armor.”

The three colts turned and looked at the Reaper. “Why's an old stallion like yourself out trick or treating?” the red coated colt asked. “And why such a stupid costume?”

“It's not a costume,” the Reaper deadpanned. “Now, I'm a nice entity. Leave now and I won't take those eggs and rolls of toilet paper and turn you all into sunnyside up mummies.”

“Hah, I'd like to see you try,” the purple coated colt said. “Hey, Quart, toss that damn cloak back so we can see who bozo is.”

The Reaper shook his head as Quart’s horn lit up and the top of his cloak was thrown back, which revealed his skeletal head, empty eye sockets, and horn—which had a vivid white glow around it. “I told you I was the real deal,” the Reaper deadpanned. “Or are you going to accuse me being a puppet being controlled by a ventriloquist?”

The trio all cowered and shook in terror. “N-no, we believe you,” the grey coated colt said. “One hundred percent, just please, don't kill us!”

“Oh, calm down you foal,” the Reaper said. “That said, why don't you clean up the eggs and toilet paper you dropped?” He pointed down at the mess on the ground. “If you do that, I won't tell your parents.”

In a flash, and without a word, the trio began to clean up the mess. Idiots, the Reaper thought as he watched the colts clean. I wonder if anyone will believe them. With that, the Reaper put his cloak back over his head and walked away.

A short while later, the Reaper arrived back at Celestia's castle. He entered the castle and, unsurprisingly, saw the two princesses in the main hall, talking.

“I got your candy,” the Reaper said as he levitated his bag over to the duo. “May I just say that this was somehow worse than your karaoke, Celly?”

Celestia chuckled. “Oh, come on, Grimmy,” she said with a warm smile. “It couldn't have been that bad.“

“I’m absolutely certain that I've scarred three colts with my face,” the Reaper replied. “I'm also certain that they've been told that at least twice in school, but that's besides the point.”

Celestia let out a sigh. “I'm so going to get angry letters about this.”

“Oh, come on,” Luna said. “Don’t dwell on that now, sister. You have all of this candy!”

“I swear, if you eat enough that you get a stomachache, I'm sending you a letter that reads ‘I told you so’ a hundred times.”

“I've told you before: I won't eat that much!” Luna protested.

“Yeah, okay, sure,” the Reaper said. “Now then, I must be going.” With that, the Reaper teleported away.

Celestia turned to her little sister. “Candy time?”

“Candy time!” Luna replied as she and her sister ran to their throne room.

The next day

“Oh, why did I eat the entire bag?” Luna groaned as she lay in her bed.

“Because you're a millennia old princess with the mindset of a foal when you get excited,” the Reaper replied as he stood next Luna's bed. “I'm just amazed that Celestia didn't bother to stop you.”

“She too ate her entire bag.”

“Yeah, I figured,” the Reaper said. “By the way: take this,” he said as he handed Luna a scroll.

Luna levitated over the scroll and unraveled it.

I told you so.

“You're the worst,” Luna said.

“I bet that stomachache of yours is worse,” the Reaper replied.

“I hate you.”