Generations

by Pippington Britishhooves

Rating: everyone
Tags: Cutie Mark Crusaders, Dinky Hooves, Adventure, Pipsqueak, My Little Pony: Friendship is Magic, Featherweight
Length: 3972

After Pipsqueak's move to Ponyville, he hopes to begin adventures in this new town. But after his first Nightmare Night turns out very different to what he expected, he may find that the real adventure is about the friendships made along the way

Pipsqueak is an adventurous young colt, and energetic at that! He's lively and curious, and never says no to adventure. After his move to Ponyville from Trottingham, he has his first Nightmare Night and finds it quite different to what he expected. Nevertheless, he pushes forward in the world to achieve his dream. His dream of having wild, endless adventures.........

So, I found an image on the internet and thought I'd make a story out of it. I love Pipsqueak and I'm so glad to be writing some much needed stories for the little guy. Enjoy. :)

Published 2014-01-26 22:40:04 UTC
Last updated 2015-12-02 03:49:18 UTC

Nightmare Night

The little pinto colt lay dejectedly on the mat in the town square, which was strewn with litter and debris. The entire town was a mess after the incident with the Princess, and the adults were cleaning up whilst the foals sat down either on the grass or the mat and tried to deal with the situation. Most of them were gathered around the little colt, listening to him as he moped.

"Gosh, I didn't think my very first Nightmare Night would be my very last." The colt hung his head down and pouted into the floor. Just how had all this happened? It'd had been great at first, trotting around the town with the others and getting candy from the adults. Even the Nightmare Moon scare had been amazing, making the whole thing just that bit more exciting. Who'd have thought that the Princess herself would turn up? But then somepony had panicked, made the Princess angry, and everypony had blindly run into everything, wrecking it all. To make it worse, she'd stormed off, announcing haughtily that Nightmare Night would be cancelled forever. It all made him so very sad.

A hoof raised his face slightly, and he looked up to see the zebra from before, Zecora, smiling down at him. She'd been their guide when Nightmare Mo- the Princess had first appeared.

"Come, little Pip, now don't you fret. Nightmare Night's not over yet." She always spoke in rhyme like that, but he wasn't sure if it was a setup for Nightmare Night or whether she genuinely spoke like that all the time. Whichever way it was, it comforted him, and he found himself smiling and standing up as the zebra mare stepped around him and continued. "We still have candy left to give, so Nightmare Moon might let us live."

Zecora was strange, but not in a bad way, Pipsqueak thought. She was mysterious and slightly spooky, although her costume may have caused her to appear spookier than she normally was. To him, she was a bit like the Princess; both were met with distrust and fear when they first came into the town (one of the fillies had whispered the story to him when Zecora was leading them into the forest before the Princess had arrived), both were strangers to the the Ponyville way of life, and both spoke in strange ways. If the zebra had managed to integrate herself into the town, then maybe it was possible that the Princess would be able-

"Yes, come on little ponies!" The voice broke Pipsqueak's train of thought, and he turned to its source. The mayor trotted towards them, apparently overhearing Zecora's words. "What's Nightmare Night without the annual candy offering?" She leaned towards the nearest filly and lowered her tone slightly. "You don't want Nightmare Moon to gobble you up, doooo yoooouuu?"

"Uh, the rainbow wig just kills it for me."

Looking at the mayor, staring at the cowering filly with wide-eyes, Pipsqueak found himself silently agreeing with the baby dragon who walked past, dragging a line of skull decorations; the clown outfit didn't really suit Nightmare Night, particularly if trying to scare somepony.

"Come on kids, doesn't that sound like fun?" called another enthusiastic voice. The group looked towards its owner, an orange earth pony dressed as a scarecrow. Two fillies in the group glanced at each other uncertainly, something that went unnoticed by the orange mare. "Come on then, let's get a-hustlin y'all."

The orange pony- Pipsqueak vaguely remembered her introducing herself to him as Applejack at some point earlier that night- shepherded the foals towards the edge of Ponyville, ushering them towards the Everfree forest. The statue was just a little way inside, making it an ideal location for the Nightmare Night candy offering; a naturally scary environment which was devoid of any real danger. However, the foals didn't feel scared as they trudged dejectedly away from the market and along the path that would take them into the little clearing.

"What do you think got her so upset?" asked one of the fillies as they passed the last of the buildings in the town. "She swooped in and started shouting. I thought we were meant to run and scream."

"Maybe she's just playing the part of the villain?" another filly, dressed in a ladybug costume, suggested hopefully. "Maybe she'll tell us tomorrow that it was all a joke or something?"

"Did you hear what she said?" demanded a third filly, her tone matching the wolf outfit she wore. "She said that Nightmare Night was cancelled forever. She's not just going to un-cancel it."

"But why?" pondered the first filly. "What did we do? Did we offend her by not complimenting her costume?"

"Maybe she felt left out because we kept running away from her," Pipsqueak spoke up. The other foals looked at him.

"Left out? Why would she feel left out? She kept doing scary stuff, like shouting."

"And the lightning!" added the ladybug filly.

"And the eating you thing!" remarked a squeaky filly dressed in a vampire costume. Pipsqueak blushed as he remembered running away in a panic after the group when the Princess had grabbed him from the barrel. He'd run off shouting that his backside had been gobbled, to which the Princess had shouted angrily after him that he was ungrateful and called him a 'whelp'. He still needed to ask somepony what that meant.

"But she saved me," he objected. "I fell into the barrel and she pulled me out. If she didn't I'd probably still be trapped in there."

The filly in the wolf costume seemed ready to retort when a voice from behind them cut her off. "Wait everypony!" The group turned to see a purple unicorn trotting from the town, the baby dragon in tow. She smiled as she drew close to them. "I wanted to give Spike a chance to take part in the candy offering."

"But I don't want to give up any candy, Twilight," huffed the little dragon. The purple mare glanced disapprovingly at him.

"Now Spike, you've already eaten enough for tonight, and you know what I've told you about sugary foods. If you eat much more you'll get stomach aches and won't be able to get to sleep for days."

"But Pinkie can eat so much and still not get ill."

"Pinkie is...well, Pinkie. She's an exception."

"An acception to what?" The foals jumped as a pink mare in a chicken suit seemingly appeared from nowhere, leaping out from behind Twilight, who only looked mildly surprised at this occurrence. "Are we accepting something now? Is it more candy? I love candy! I mean, I know everypony loves candy, but I really really love candy! Is that where we're going now, to get more candy?"

"I wish," muttered Spike.

Pinkie looked around expectantly, eventually spotting the group of foals. "Oh, hey Pip."

"Hey Pinkie," Pip replied unethusiastically.

"Can't we just get this over with?" asked the wolf-costume filly in a slightly irate tone. "Standing around here isn't going to get our candy back."

"Yep, that's a good idea," chirped Pinkie happily, apparently missing the disdain in the young filly's voice. "If we want candy, we're going to have to go and get it!" She started to bounce towards the forest, getting a good distance before pausing in mid-air and somehow bouncing in reverse back to where she started, as though she were a film reel being played backwards. She glanced at all the foals and the candy bags around their necks. "Hang on a second. You already have candy." She gave them suspicious glances. "Are you all being greedy?"

"Pinkie, we're not going to the forest to get candy, we're going there to give it," Twilight explained to the pink mare who was currently leaning towards the ladybug filly with a rigid look of mistrust locked on her face. Pinkie's head whipped round at this revelation.

"Give candy away? But who are we giving it to?"

"The statue of Princess Luna," Twilight reminded her. Pinkie continued to look at her with confusion. "The candy offering? The tradition where everypony goes to give some of their candy to Nightmare Moon so that she doesn't gobble them up?" No reaction. "Pinkie, you were there when Zecora explained the tradition to you. Didn't you listen to what she had to say?" A mote of annoyance crept into the purple unicorn's voice, something the foals knew to be more from Pinkie's disregard for learning the history behind the legend rather than her lack of recollection of the event itself. Twilight had been around Pinkie enough that she had garnered a large amount of patience for the mare's antics and usually dismissed them with a shrug or a roll of the eyes.

"Oh! THAT candy offering!" Pinkie suddenly exclaimed, breaking off into a giggle. "Silly me!" Twilight gave Spike a glance, to which he shrugged in response. Without speaking, the group set off once again, Zecora leading them into the forest and towards the clearing. The foals followed closely behind, with the mayor, Pinkie, Spike and Twilight bringing up the back of the line.

Before long, the statue came into sight, looming menacingly out of the darkness like a spectre, rearing up on the pedestal. It looked very lifelike, Pipsqueak noted, shivering slightly. The craftspony had clearly put their heart and soul into their work, managing to capture the fierce look that he remembered from the Princess' face, although maybe that was the way the shadows played across its face. Either way, some amazing talent had gone into producing it. It was just a shame that he'd never be able to come here to see it again, or at least not during Nightmare Night. He wondered if the townsponies would have to remove it at the Princess' behest,  but that train of thought dug him deeper into his pit of sorrow, so he tried to stop thinking at all.

The filly in front of him deposited her candy into the pile before stepping back glumly, not turning to look at him but merely staring straight ahead. He stepped forward and placed his bag on the ground, looking up at the imposing figure of Nightmare Moon for what he realised would be the last time. It sneered down at him, offering him no remorse, no compunction.

"Goodbye Nightmare Night," he whimpered, lowering his head and closing his eyes despondently as the disappointment crashed down on him. "Forever." He turned to walk away, not wanting to stay any longer than he needed to. He was leaving it all behind, and he'd only had the chance to experience one. It seemed brutally unfair to him, but his gloom gave him no room to feel annoyed or angry.

A sudden crash of thunder brought him back to his senses, and his head shot up, his eyes springing open. The wind picked up, whistling around him. Leaves whipped at his coat as they were dragged along in the sudden gale. He didn't move, his mind attempting to register the spontaneous change from stillness to the billowing storm, uncertain of what he should actually do.

"Citizens of Ponyville!" a powerful, authoritative voice called out, easily drowning out the whining of the wind. Pipsqueak looked around in terror, searching for a source to the commanding tone. The others were searching too, and even Zecora was backing away, something which frightened the little colt; this wasn't some setup like when she had first lead them here. Nopony knew what was going on this time. "You were wise to bring this candy to me. I am pleased at your offering."

The wind picked up in strength, howling as the ponies clutched themselves tightly in an effort to both prevent themselves being snatched up in the ferocious squall and to fight off the bitter cold it brought. Applejack barely noticed as her straw hat was swept from her head and dragged along the ground, bouncing along the dirt. Pipsqueak followed its path with frantic eyes.

"So pleased that I may just eat IT...." The hat was lifted up by the currents and floated several meters before passing in front of the statue, where a sudden gust propelled it upwards and....

Pipsqueak's breath caught in his throat as he found himself gazing up into the face of the now animate carving of Nightmare Moon. She leered hungrily down at him, eyes glowing a fierce white as though possessed, ethereal mane fluttering placidly in spite of the wind whipping around her, and teeth bared.

"...instead of eat YOU!"

The foals screamed in unison, turning and fleeing as quickly as their legs could carry them. Pipsqueak leaped hurriedly behind them, trying to keep up and just managing to do so. Sparing a terrified glance backwards as he ran, the little colt espied a bright glimmering light emanating off Nightmare Moon. She seemed to shrink, her dimensions changing into something far less intimidating and familiar. In fact, it almost looked like....

"Everypony, wait!" he called out to the others as he pattered to a halt. The group looked back and ground to a halt too, frantic expressions carved into their faces.

"Run!" one of them shouted back to him. "What are you stopping for? We have to get away!" Pipsqueak didn't move.

"I think it's okay," he replied, peering back to the plinth where Princess Luna had started conversing with the purple unicorn. "I think it was all an act." His eyes widened at the possibilities. "It's an act! She just wants to scare us! It's all in the spirit of Nightmare Night! If somepony just talked to her-"

He felt a pair of hooves spin him around, and found himself inches away from a disconcerted orange pegasus. "Are you mad or something? It's Nightmare Moon! You don't stop and talk to her, you run!" The colt pulled away slightly.

"But it's not Nightmare Moon, it's just Princess Luna, look." He stepped aside to allow the filly to look where the statue had been not long before. The rest of the group slowly trotted forwards to join them, trying to listen in on the conversation. The orange filly's expression loosened slightly, but she still bore a look of deep suspicion. "If she really was Nightmare Moon, would she really be standing there talking to another pony like that?" A small murmur of agreement passed through the foals at this.

"Okay," the filly conceded. "But even if she is just Princess Luna, how does this help us?"

"Because we don't need to be afraid of her. If she is a Princess, maybe she just wants to fit in."

"Why would a Princess want to fit in?" asked the ladybug filly. "She has power, she doesn't need to fit in."

"Maybe she's bored or something. But if she is, and we don't want Nightmare Night to be cancelled, maybe we can still have her come and scare us every year. Even if we don't have Nightmare Night to look forward to, we would still have this."

"But how are we going to get her to come along and scare us every year?" squeaked the white unicorn in the vampire costume. The pinto colt took a deep breath.

"I could just ask her."

Silence fell across the group for a few brief seconds in which they all stared at him. Finally, a small voice spoke up from the back.

"Maybe somepony should go an' talk ta her. After all, that's how I...we met Zecora, an' she's really friendly. What if this is the same?" The foals shifted their gazes to her, uncertain of how to respond.

"She does have a point," agreed the squeaky filly slowly. "Nightmare Night is meant to be scary, and we were scared tonight." The other foals readily nodded their agreement. Pipsqueak smiled.

"I'll go and ask her if she can keep coming to scare us each year, and hopefully she'll say yes." Turning around, he heard a rustling from behind and gave a quick glance over his shoulder, seeing that all of his friends had immediately choose to hide behind a bush. Facing forwards, he gulped audibly and started his walk towards the towering Princess. Each slow, small step seemed a risk, as though she would turn around and see him approaching her, and angrily banish him to the moon, or smite him down somehow, but despite his nervous disposition clawing at him as he made his way forwards, the purple unicorn was apparently holding her attention enough get close to her without her noticing. She leaped down from the plinth, turning to face the unicorn once more and raising a hoof in scepticism.

"For what? For...for them to scream some more?" she asked in a disappointed tone. The little colt was close to her now, and he thought about how he should address her. What should he say when talking to royalty? Whatever the procedure, he needed to get her attention first, and that was his biggest hurdle. He was the youngest foal in the group, a good three years younger than the rest of them, and as such, his frame was smaller. He couldn't do a throaty cough like he had heard Filthy Rich do to gather attention, and he couldn't catch her eye with a gesture either. Left with little else choice, he decided to tug on the nearest thing he could reach of hers- her mane.

He was surprised that he had even managed to grasp it, expecting it to be some sort of gas. Instead, he pulled down gently, and tugged the mane of royalty to get her attention. His nerves doubled when he took hold.

"Ummm, Princess Luna," he began uncertainly, releasing her mane as he did so. She looked down at him in surprise. "I know there's not going to be anymore Nightmare Night, but do you suppose maybe you could come back next year and scare us again anyway?" Excitement crept into his voice as he continued, and, despite himself, he finished his question with a wide beam of a smile. The Princess looked up towards the bush, spotting the nervous heads peaking around it.

"Child, art thou saying that thou..." she began before trailing off momentarily, bewilderment evident in her tone. "...likest me to scare you?" She gave him an astonished gaze, her eyes narrowed and her head pushed forward, as though unsure of what she had just heard.

"It's really fun," Pipsqueak confirmed, nodding excitedly. "Scary, but fun!"

"It....is?"

"Yeah. Nightmare Night is my favourite night of the year!"

"Well then," the Princess replied with a small intake of breath and a wide smile, apparently as happy about this as Pipsqueak was. "We shall have to bring NIGHTMARE NIGHT BACK!" The sudden use of the Royal Canterlot Voice blew the colt back several meters, but he immediately jumped back to his hooves, giddy with the news that his new favourite festival wouldn't be cancelled after all.

"Woah! You're my favourite princess ever!" He ran up and wrapped his forelegs around one of hers as a quick gesture of thanks before darting back towards the group, who now wore similar giddy expressions as his. He didn't wait until he reached them to share the good news, shouting out to them as soon as he had turned away from the princess. "She said 'yes', guys!"

The group cheered as he raced towards them, moving out from behind their hiding place to bounce about in their excitement. It took a few minutes before any of them thought to stop for a moment to go and share the news with the others in town, or even to go back to celebrating the festivities.

Their hectic arrival into town brought them a lot of attention, and so they were quickly able to spread the word about the reinstatement of all Nightmare Night festivities. When Princess Luna herself walked into the town, none of the ponies cowered away, and although some remained at a cautious distance and held a wary gaze, she was welcomed into the celebrations warmly, particularly after she helped repair and reset some of the damages and decorations. Alicorn magic had many uses, and renovations were no tough task for those who wielded it. Within half an hour, the festivities were back on in full swing as though they had never deviated from that state.

"Hey, Pipsqueak." The little foal pulled his head out of the bucket, giving up on trying to catch the apple for the meantime. Three fillies were approaching him, and although he'd spent the night going around the town with them, he hadn't caught their names. The white unicorn in the vampire costume, the orange pegasus in the wolf outfit, and a yellow earth pony dressed as what looked like, well, some sort of zombie. Bolts in the side of her neck? Looking as though she was stitched together? He certainly hadn't heard of anything like that before, but he did feel impressed by her creativity.

"Hi there," he responded chirpily, dropping down to the ground. They stopped in front of him.

"We just came to say thanks for sorting everything out tonight," the unicorn told him. Pipsqueak smiled.

"It wasn't a problem. I'm just glad that Nightmare Night's still on."

"So are we, an' that's our point," the earth pony interjected. She had a strong accent that he usually associated to farmers and rural workers, although his parents had always taught him to never judge a pony by their outward appearance. He realised at that point that it had been her who had spoken up for his idea to just speak to the princess. "We like it, you like it, an' everypony likes it. What you did took guts, and we wouldn'ta had this ever again if it hadn'ta been fa you."

The colt blushed profusely. "Um, thanks."

"Well, we wanted to say thanks for saving Nightmare Night-"

"I could have done it if I hadn't have been held back," the orange filly interjected.

"Nopony was holdin' ya back, Scootaloo," the earth pony responded with a sigh, rolling her eyes.

"-and we thought that the best way to say thanks was to invite you to hang out with us," the unicorn continued, apparently used to these sorts of interruptions. She smiled brightly at the smaller colt.

"I think that would be nice," he replied. "I'd need to ask my parents, but that sounds awesome to me."

"Well, just tell your parents that you'd be hanging out with the Cutie Mark Crusaders, there's no way they could say no!" the pegasus told him confidently. The other two shared winces.

"Or," the unicorn suggested, "maybe just say that you're hanging out with Sweetie Belle," she indicated herself, "Apple Bloom," she motioned towards the earth pony, "and Scootaloo," pointing a hoof at the pegasus who was, at this point, striking a pose. "We're never sure how ponies will react to hearing about the Cutie Mark Crusaders."

Pipsqueak nodded happily. "I will guys, thanks for the offer."

"Thank you for the heroism."

With a final wave and a smile, the three of them turned and walked away, Scootaloo whispering to Apple Bloom that she did too have somepony holding her back. The colt smiled. This night really had turned out great. He'd been excited for it when he was getting ready, and in the days and weeks before the event, but now everything seemed even better. Nightmare Night would remain a public holiday, he had potentially made three new friends, and he'd met the Princess of the Night herself. With a smile that would impress even Pinkie Pie, he clambered back up the side of the barrel, ready to try to get at least one apple before the night was over.

Daydreaming

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Afternoon activities

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