My Little Nightmare

by White Magical Stache

Rating: everyone
Tags: Crossover, Main 6, My Little Pony: Friendship is Magic, Comedy, Other, Adventure
Length: 4761

What happens when an upbeat, undead Halloween enthusiast accidentally discovers Nightmare Night? I don't know, you'll have to find out!

Every now and then, one gets bored of the same old routine all the time. When that happens, what do you do? Some people go out and find something new to do. Or sometimes, they find someone else who could clearly use their help with what they're doing. Because obviously you know how to do it much better than they can, and they'll certainly appreciate all the help...right?

Published 2013-03-24 00:50:01 UTC
Last updated 2013-03-24 00:50:01 UTC

Chapter 1

‘Twas a short time ago, when you look back,
That I told you the story of Skeleton Jack.
You may have thought his lesson was learned
When his attempt to take over Christmas was spurned.
But no, dear old Jack, thought to take on a whim,
Another day that was not for him.
An event, my dear reader, which could have been tragic,
Had Jack not discovered that friendship is magic.

Jack Skellington paced back and forth about the town hall, crossing nearly the entire length of it in a few paces. As he walked back and forth, scratching his bright white skull, a man nearly twice as wide as he was tall came running into the room, shuffling for Jack as fast as his small legs would carry him.

“Jack! I have the plans for next Halloween!” he exclaimed happily, dropping the scroll he was carrying on a table near where Jack was. Jack looked up from his thoughts and smiled.

“Excellent! I’ll just have a look at them, if you don’t mind, Mr. Mayor,” he said, striding over to the table and leaning down to pick up the scroll. The Mayor’s face was what could best be described as a smile with eyes, clearly pleased with himself and humming a tune while fiddling with his ridiculously tall hat, which still left him not even half as tall as Jack himself. Jack stood up straight and unrolled the scroll in front of his face, examining it for a few moments with his hollow eye sockets, his face quickly turning from a smile to a frown. “Oh, no, Mr. Mayor, this won’t do at all.”

“B-but, why not!?” exclaimed the Mayor, his face turning a full 180 degrees to reveal a pale white face with an oversized frown. “It’s just as scary as last year!”

“Exactly, and that isn’t good enough,” replied Jack, rolling up the scroll and placing it back on the table. “We need this year to be our most terrifying yet. Simply meeting last year is unacceptable.” He brought a bony hand to his chin. “We need to think of something. We’ve only got eleven months to plan this. There’s no room for mistakes.”

“Well, what are we going to do? You’re the Pumpkin King, you must have something in mind!” shouted the Mayor, unable to contain his panic.

“I have an idea of what I can do to get some ideas,” said Jack simply.

“W-what? That doesn’t make any sense!” cried the Mayor in anguish.

“Or does it make perfect sense?” asked Jack coyly, tapping a finger against his skull. “Ideas don’t always come to you unless you have an idea of how to get the idea you need. Luckily for you, Mr. Mayor, I know exactly what I need to do to get some ideas for this upcoming Halloween.” With that, he was off, leaving the building in a few short strides, before the Mayor could voice a complaint. The Mayor, now alone in the room, simply threw his arms up in defeat and shook his head, murmuring to himself and picking up the scroll from the table.

Jack jogged to his home as he left the town hall, his mind compiling a list of what he felt he would need for the trip he was about to take. He reached his home quickly, running upstairs to his room and workshop, and took a bag from a shelf, throwing objects into it, ranging from books and jars of strange substances to beakers and microscopes. When he felt his bag had what it needed, he closed it up and ran back downstairs, into the road outside and towards the forest outside of town. The Mayor, who was just leaving the town hall, saw him and called out to him.

“Jack! Where are you going!?” he cried, his face still stuck in the expression of worry and fear that it had been upon having his plans rejected.

“I’m going into Twisted Woods to get some new ideas!” Jack yelled back, already out of the gates of town. He turned around to face the town just as he was reaching the edge of the woods. “I won’t be gone long!” he assured the Mayor before heading into the trees. The Mayor simply shook his head and sighed, knowing perfectly well that Jack’s promise was not going to be kept.

“C’mon, Zero, we’ve got work to do,” Jack said as he passed a small tombstone on the side of the path. A small ghost dog with a glowing orange nose emerged from the stone and barked happily, following Jack. “We’ve got to find something new and scary to make this next Halloween something special. It needs to be our most terrifying one yet.” Zero barked in approval as Jack continued on the path.

Jack continued walking down the path for what seemed like hours, though he knew it was only a few minutes. He didn’t let the strange sense of time get to him, he knew it was likely both his excitement combined with the strange effect given off in the area he was going to. When nearing the trees he was looking for, time seemed to change, moving faster, slower, or not at all, depending on where one was standing. Not long after he began feeling the strange time effects, he came to a clearing with trees all around the edge of it, each one decorated with a festive door. Jack entered the middle of the clearing and began turning, trying to decide which door to go through, when a door caught his attention.

“I don’t believe I’ve seen this one before…” he mumbled to himself, approaching one of the doors as Zero floated behind him, barking nervously. The door was shaped like a sun, a yellowish circle with a light orange ring around it, with eight orange waves protruding from it. In the middle was a handle shaped like a crescent moon. “Well, it’s rather simple, wouldn’t you say, Zero? Nothing like the door to Christmas Town,” said Jack, running his hand along the door. “It couldn’t hurt to take a look inside, now, could it?” he asked to nobody in particular. He took hold of the handle and turned it, opening the door and looking inside the tree. Inside, it looked just like the tree to Christmas Town: pitch black and seemingly bottomless. Jack smiled. He could already tell this would be fun. He turned to Zero, waved, and leapt into the tree, letting the magical forces inside take him wherever they wanted him to go, laughing all the way.

Twilight Sparkle woke up with a start, with the sensation that she had just had a nightmare, but unable to remember what the nightmare was. After a few moments, she decided that it didn’t matter and got out of bed, going over in her head what she had to do for the day. She was about to schedule the entire day for studying when Spike came from the kitchen, carrying a tray with a daisy sandwich and a glass of orange juice on it.

“Good morning, Twilight! Here’s your breakfast!” he said happily, holding it out to Twilight, who took it from him with magic and placed it on the table.

“Good morning, Spike. How did you sleep?” Twilight asked as she magically lifted the orange juice from the tray and took a sip.

“I could barely sleep, not knowing what today is!” Spike responded enthusiastically. “So when are we gonna go?”

“Go where, Spike? What’s today?” asked Twilight. She hadn’t the slightest idea what Spike was talking about, but it sounded important to him.

“You said that we could go out and get our costumes for Nightmare Night today, remember?” Spike chuckled in delight at the idea. “I already know what I’m gonna be.” He chuckled again as he thought about it.

“Oh, that’s right!” said Twilight, remembering what she had said. She still needed to get the supplies for her Star Swirl the Bearded costume, and Nightmare Night was just a few days away. “I still need to get that dye for my costume from Zecora…but first, let’s go pick out a costume for you.”

“Alright!” exclaimed Spike enthusiastically, hopping on Twilight’s back. Twilight left the library, unsure of where to go first. This time of year, there were costume stands all over town. As she walked through town, Spike analyzed every costume he saw from her back, trying to decide which one would be best for him. Twilight laughed quietly to herself, shaking her head and wishing that Spike would put as much effort into tidying up as he did into looking for a costume. Just as she was about to leave the town square, she noticed a vendor with a hat that looked perfect for her costume. Surprised that anypony had such a hat, she went to see how much it cost.

“Um…excuse me?” she said as she approached the vendor. “How much is that hat?” she asked, motioning to the hat. The pony behind the stand, a large pony that looked like he didn’t get out much, looked back at her in annoyance.

“That one’s 20 bits,” he replied in a voice befitting his gruff appearance. Twilight gasped upon hearing that, appalled at what she thought sounded like nearly twice what it was likely worth.

“20 bits? You must be joking! That hat isn’t worth 20 bits!” she exclaimed. The vendor looked back at her with a bored look on his face, suggesting to Twilight that he had this sort of discussion nearly every day.

“20 bits. Nothin’ less,” the vendor replied simply. Twilight was about to argue more when Spike tugged at her mane.

“Just pay, Twilight,” he said. “You know you’re not going to convince him to lower it.” Twilight sighed. Spike was right, and she knew it. She reluctantly counted out 20 bits from her bag and dumped them on the stand, magically lifting the hat from the stand and pushing it down into her bag, leaving the vendor, who was looking rather proud of himself. “Don’t feel bad, Twilight,” Spike said from her back. “At least you got your hat.”

“I know, but now I don’t have as much money for your costume,” she said, sighing. “I only have 30 bits for your costume now. So hopefully we can find something cheap that you’ll like.” She could hear Spike’s disappointed groan, which almost convinced her to go back and haggle with the vendor more, before Spike suddenly jumped up on her back.

“There! I want that one!” he shouted, pointing excitedly at a stand with a multitude of small costumes hanging on display. Twilight laughed at his reaction.

“You really are enthusiastic, aren’t you? Alright, let’s go look at them,” she said, walking to the shop. When she reached the cart, though, it seemed to be without a vendor to run it. Twilight looked around for a moment before calling out. “Hello?” she asked. “Is anypony there?”

“Hiya Twilight!” exclaimed Pinkie Pie, jumping up from behind the stand, causing Twilight to jump in surprise, which almost caused Spike to fall off her back. Pinkie Pie couldn’t help but laugh when she saw Spike scramble to get back on Twilight’s back. “And hiya Spike, too!” she said, waving at them both. “What brings you two to my costume stand?”

“Well, we wanted to buy a costume,” Twilight started.

“Well, duh! Of course you did! Why else would you be here at my costume stand?” interrupted Pinkie Pie.

“What? But, you just asked…” Twilight attempted to say.

“I asked what you’re doing at my costume stand, yeah-huh. So, what is it that you’re doing here?” asked Pinkie, seeming genuinely curious about the reason she had just stated and seemingly forgotten.

“Uh…I’ll let Spike handle this. It’s his costume,” Twilight said, turning to let Spike face Pinkie Pie, and sighing in relief. At least now it wasn’t her who’d have to deal with Pinkie Pie being Pinkie Pie.

“So, yeah, I wanted that costume!” Spike said, pointing. Twilight turned her head to see which one he was pointing at, and was surprised to see him pointing directly at a dragon costume.

“Oh, great choice, Spike!” exclaimed Pinkie, with as much enthusiasm as if she’d just been told that she’d won the lottery. She pulled down the dragon costume, folded it up in a box, and put it in a bag, giving the bag to Spike. “I’m sure it’ll look great on you!” she said, smiling.

“How much is that going to be, Pinkie?” asked Twilight, removing her money bag, but Pinkie held up a hoof.

“I’m not going to charge you! You’re my friends! You can just have it,” she replied with a smile. “Anything else you need? I’ve got all sorts of fancy costumes for you too, Twilight!” Twilight shook her head.

“No thank you, Pinkie, I think I’m…” she trailed off, looking at a robe folded up on the stand. “Actually…maybe I’ll have that robe,” she said, pointing to it. “It’s perfect for my costume.”

“Okey dokey lokey!” replied Pinkie happily, putting the robe in a box which Twilight lifted with magic and gave to Spike. “Anything else?” Twilight thought for a moment, then realized she was missing something.

“Do you have any dye?” she asked. “Blue dye for the robe. It’s white and I need it to be blue for my costume.”

“Maybe!” replied Pinkie, disappearing behind the stand. Twilight glanced over to see where she had gone, but couldn’t find her anywhere, or see where she had gone. As she examined the spot Pinkie had been standing, a hoof tapped her from behind. She turned to find Pinkie Pie standing behind her, smiling. “Whatcha lookin’ at?” she asked.

“What? But…you…” Twilight sighed, realized it was just Pinkie Pie being Pinkie Pie. “Never mind. Did you have any dye?” Pinkie shook her head.

“Nope, sorry, Twilight, nopony in town had any,” Pinkie said, shaking her head. But that’s okay, I’m sure you could make some. All you need are a couple flowers from the Everfree Forest, I can give you a list of them.”

“Thank you, Pinkie, that would be wonderful,” replied Twilight, slightly disappointed. Nopony in town had any? Blue must have been popular around that time of year. A few minutes later, she was walking past Fluttershy’s cottage to enter the Everfree Forest, having received the list from Pinkie Pie of what she needed. At the edge of the forest, she took the note Pinkie had given her out of her bag and read it. “Blue forest flowers…and that’s it?” She groaned. “Why couldn’t she have just told me that?”

“Um…excuse me, Twilight…are you okay? You sound bothered,” said a small voice from behind Twilight. She turned and there stood Fluttershy with a slightly concerned look.

“Oh, no, it’s nothing, don’t worry about it, Fluttershy,” Twilight said, rubbing the back of her neck in embarrassment.

“Oh…okay,” replied Fluttershy, seeming calmer now. “So, what are you doing out here by the forest?” she asked.

“I’m just going to go in to get some blue forest flowers to make some dye for my costume,” Twilight replied, giving a smile to help Fluttershy not worry as much as she was certainly going to about Twilight going into the forest. As if on cue, Fluttershy gasped.

“Into the forest? But Twilight, there are dangerous creatures in the forest,” she began.

“I know, its okay, Fluttershy,” interrupted Twilight. “I won’t go very far in, okay? I just need to get some flowers. I’ll be fine.” She smiled, and Fluttershy stood quietly for a moment, nodding slightly after a few moments. Twilight waved goodbye and trotted into the forest, leaving Fluttershy standing at her cottage, watching her go.

“So, how many of these flowers do we need?” asked Spike.

“Only about a dozen to make enough dye,” replied Twilight, trotting down the path and looking from side to side to see if she could spot any flowers. Spike groaned, obviously not wanting to spend the time looking for a dozen flowers. Twilight simply shook her head and giggled. About ten minutes later, Twilight was far enough into the forest that seeing anything without lighting up her horn became a challenge, but she had also collected four of the flowers that she needed. She spotted another collection of the flowers, but as she approached them, a series of strange event occurred at what seemed like the same time.

First, there was a very loud whooshing sound, as if a hurricane were passing directly overhead. The sound subsided almost immediately, but was followed by a strong gust of wind and an incredibly bright flash, seemingly from nowhere. Twilight covered her eyes with her hoof out of instinct, but was knocked to the ground by the wind, causing her collected flowers to fall out of her bag and land near the flowers she had intended to pick, as well as knocking Spike off of her back and onto the ground, the boxes he was holding landing near Twilight’s flowers. Twilight groaned and shook her head as she sat up, regaining her composure.

“What happened?” she asked groggily as she looked around to try to get her bearings. To her left was Spike, laying on the ground in much the same state as she had been a moment ago, also groaning. To her right were the notepads, inkwells and quills she always had in her bag. And in front of her were the flowers she had picked, the costumes she’d gotten from Pinkie, the flowers she had been about to pick, and…something she couldn’t make out very well, standing on those flowers. She mustered what focus and strength she could to illuminate her horn, and as she did, she laid eyes upon something she couldn’t very well describe.

Whatever it was, it was standing on its hind legs and was tall, impossibly so, taller even than Princess Celestia or a manticore. It was also incredibly thin; its limbs couldn’t be more than 2 or 3 inches thick at most. It seemed to be wearing clothing of some kind, a deep black suit with white stripes and an odd looking tie. Most confusing were its hand and face, which seemed to be pure white, and without any real features. It looked like it was just a skeleton in a suit, but a skeleton of what, she had no idea. As she looked on in awe and terror, the creature looked around for a moment, then turned and noticed her, smiling and leaning down to her.

“Well, hello there,” it said, “I’m not from around here, but it’s absolutely wonderful to meet you.”

Chapter 2

Twilight stared up at the creature, her mind working furiously to try to identify it and a way to get away from it, but her thoughts were too clouded by fear to come up with any feasible solutions. The creature just sat still, leaning down to be just about a foot from her face, looking her over with its empty eye sockets. She couldn’t understand how it could see without eyes, but she didn’t care. All she knew was that she had to get away. That was all her mind would tell her. Run. Run. Run. That’s all she could think. She scrambled to her hooves and took off running, not caring which direction she went in. The creature made no effort to follow, instead simply watching her go in confusion. She ran and ran, but not for very long before she heard Spike scream and remembered that she’d left him back with the thing in the flowers. She turned around without a second thought and came into the clearing, where the skeleton now stood next to Spike, who had backed against a tree.

“Get away from him!” shouted Twilight, illuminating her horn to see the thing more clearly, her fear now overshadowed by her concern for Spike. It looked over at her and somehow smiled, despite having nothing even resembling lips.

“Please, please, I think we’re all getting off to a terrible start,” it said, turning to Twilight. “I’m not here to hurt you or your friend. I’m not even certain where ‘here’ is. Perhaps we could help each other? My name is Jack Skellington, Pumpkin King of Halloween Town, at your service.” He took a deep bow, and then extended his bony hand. Twilight watched for a moment, unsure of how to react, then turned to Spike, who was still backed against the tree, but looked much more confused than scared. Cautiously, Twilight took a few steps forward, her curiosity overpowering her fear, which melted away more and more with every second she was near Jack. As she looked at him now, he didn’t seem very menacing at all. He actually looked fairly comical, now that she got a good look at him, but he gave off a sort of feeling of fear, like the little voice in the back of your head would always warn you of him when he was there.

“I’m Twilight Sparkle,” she said cautiously as she extended her hoof to his hand. He took her hoof and started shaking vigorously.

“Oh, wonderful! I’m already meeting new people. Positively wonderful!” Jack exclaimed, smiling even more broadly. He looked down to Spike and released Twilight’s hoof to slap his forehead with his hand. “Oh, where are my manners? Here, please, allow me to assist.” He leaned down to pick up Spike, who scrambled out of the way to hide behind Twilight. Jack looked confused for a moment, and then sighed. “Ah, yes, I do have that effect on people. Can’t be the Pumpkin King without being scary, now, can you?”

“Pumpkin King? Halloween Town? I haven’t heard of those…” said Twilight, thinking clearly now that her fear had mostly subsided. “Where is this Halloween Town? And why is foreign royalty in the middle of the Everfree Forest?”

“Well, it’s really more of a title than anything,” chuckled Jack. “I don’t really give orders nor have subjects or anything of that sort. As for where Halloween Town is, it’s…far away. That’s about the best I can describe it. But right now, I’m more interested in knowing where I am, and who you are. More than just your name, I mean.”

“Well, like I said, I’m Twilight Sparkle. I’m a unicorn pony, as you can see, and I live in the Ponyville Library and work there as the librarian. This is Spike, my assistant,” she said, moving out of the way to let Jack see Spike, who looked up at Jack for a moment in fear before his expression changed to one of wonder.

“Whoa…you’re tall!” said Spike, looking Jack up and down. Jack chuckled.

“Oh, and I’m the protégé of Princess Celestia herself,” said Twilight with pride, puffing out her chest slightly and closing her eyes.

“Oh? She sounds important,” commented Jack curiously. Twilight’s eyes snapped open.

“Important? Important doesn’t even begin to describe it!” she commented furiously. “She’s the head of Equestria, not to mention the most powerful pony around!”

“Okay, I didn’t mean to offend,” said Jack. “I’m terribly sorry if I caused some offense, I simply haven’t been here before.” Twilight blushed as she realized how she’d reacted.

“Oh, no, it’s nothing, I’m sorry, she’s just sort of my idol,” responded Twilight. “Well, come on, I’ll take you back to Ponyville and introduce you to everypony, but you’ll need to wait a bit for me to get them ready to meet you, since you have that…effect on ponies.” She used her magic to lift up all the items that had fallen out of her bags and placed them back in, also picking the few last flowers she needed.

“Thank you very much,” replied Jack politely. “If I may, though, I simply must ask. Is all of Equestria as horrid as this…what was it, Everfree Forest?” He looked around in wonder, and Twilight shuddered as she began walking back down the path she’d come from, with Jack in tow and Spike on her back.

“Thankfully not,” she replied. “This is the only part where everything is so dark and scary and…well, like you said, horrid.”

“Oh, that’s a shame,” sighed Jack. “I suppose I’ll need to spend some time in here, then.” Twilight couldn’t figure why he would think it was bad that only the forest was so dark and dangerous, but decided it was a question based saved for later, as they continued down the path back to Ponyville.

The town that Twilight brought him to, Ponyville, was amazing to Jack. Everything was brightly colored, from the buildings to the inhabitants, to whom Twilight had said Jack was simply a decoration, animated by magic. While it had slightly disappointed Jack to not get to meet the townspeople, it hadn’t ruined his mood. This town was too wonderful for that, and Twilight had agreed to introduce him to her friends, anyway.

“This is my friend, Pinkie Pie,” Twilight said as she brought Jack to a bright pink pony that had been standing around eating candy. Jack smiled at her color. This single pony was more brightly colored than all of Halloween Town.

“Hello there,” said Jack, smiling and waving down at the pony. “My name is Jack Skellington, and contrary to what you might have thought, I’m not a decoration.”

“Hi! I’m Pinkie Pie!” exclaimed Pinkie Pie, bouncing up to look Jack at eye level for a moment. Jack chuckled at the pony.

“You’re quite the jumper,” Jack observed. “It’s nice to meet you. Something tells me we’re going to be good friends.”

“Oh, can we? I love making friends!” Pinkie shouted happily, bouncing around Jack and Twilight as they walked to the library. “Oh, Twilight, did you ever find those flowers for the dye for your costume?”

“Yes, I did, Pinkie. In fact, that’s how I met our friend here,” Twilight said, motioning to Jack. “I’m sure the costume will look wonderful now.”

“Oh, that’s great, Twilight!” said Pinkie excitedly, as if Twilight finding the flowers had been the most important thing in the world.

“Um, excuse me?” said Jack. “I couldn’t help but overhear you talking about costumes, and I noticed a lot of costumes and decorations being sold in town. Might I ask what it’s all for?”

“Oh, of course, I can’t believe I forgot to mention it,” said Twilight. “This is all in preparation for Nightmare Night, which is just a few nights away.”

“Nightmare Night?” asked Jack, now full of interest. “What’s Nightmare Night?”

“Oh, it’s great!” cried Pinkie Pie. “Everypony dresses up in costumes and goes around to other pony’s houses and gets candy and everything is scary and it’s all just great!”

“That’s a very rough summarization, but for the most part, she got the main parts down,” said Twilight. “It’s a holiday where we all go out and have fun with games and candy and the occasional scare.”

“Scares, you say?” repeated Jack, putting a hand to his chin in thought. “Nightmare Night…I like the sound of this holiday. I like it very much,” Jack said, grinning.

“Well, why don’t you stick around for it? I’m sure you’d fit in just fine,” Twilight said smiling.

“Oh, I think I will,” chuckled Jack. “Maybe I could help you prepare for it? I have a bit of a knack for this kind of thing.”

“That sounds like a great idea,” Twilight said, nodding. Jack smiled. A whole new holiday, just like Halloween, but with a brand new audience, just waiting for his amazing tricks of terror. He chuckled to himself at the thought of everything he could do.

“We’re here,” said Twilight, breaking him out of his day dream. He looked up and noticed that ‘here’ in this situation was a large tree with windows and a door. As Twilight and Pinkie Pie walked in the door, Jack had to duck down to nearly a third of his normal height to fit in the door.

“SURPRISE!” yelled Pinkie as Jack got in the door. He turned to face her and saw her, Twilight, and four other ponies all standing around a table with cakes and other treats all over it.

“What is this?” Jack asked.

“Were you surprised? I knew it!” Pinkie Pie exclaimed, laughing. “This is your surprise party to say welcome to Ponyville, silly!” Jack smiled. He was going to like it here.