The Dashing Rogue

by Tatsurou

Rating: everyone
Tags: Princess Luna, Original Character, Comedy, Pipsqueak, Pinkie Pie, Slice of Life, Applejack, My Little Pony: Friendship is Magic, Romance
Length: 3061

A little filly's first Nightmare Night in Ponyville leads to a 'life-changing' meeting. Birthday Story for Overlord-Flinx.

My name is Buttercup. I'm six years old.
My parents have always been on the move, since my father's a travelling merchant. However, my Mom finally put her hoof down, and said a little filly like me needs friends, schooling, and a permanent home. Now we're in Ponyville.
I've never dressed up for Nightmare Night before, beyond posing in costume at Father's stall. This is going to be my first Nightmare Night I get to go out and have fun with others my age. I hope it goes well.

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Birthday present written for Overlord-Flinx.

Published 2013-09-24 02:10:03 UTC
Last updated 2013-09-24 02:10:03 UTC

Chapter 1

I gently adjust the gilt tiara in my blonde mane, trying to get it to sit just right. I glance down at myself as I finish. I don't know about the green dress against my white coat, but Mom says it looks good on me and brings out matching shades in my eyes. I don't know what she means, but Mom says so, and Mom is always right, that's what Father says. He especially says it when Mom is in the room.

Smiling, I pick up the jack-o-lantern bucket I will be carrying with me to collect candy. This is the first time I've been able to gather candy on Nightmare Night, now that we've settled down here in Ponyville. We've only been here a few weeks, but I'm hoping tonight goes well. I still remember when we first arrived. A pink pony broke into our house with a bunch of the locals to give us cake. I've never seen such a friendly grown-up before. It was a little scary.

I walk carefully down the stairs, smiling. Despite not having been here long, I'm hoping to have a lot of fun and make a bunch of friends. It would have been easier at school, but Mom says there was a snafu in the paperwork, so I can't start my schooling yet. Either way, I'm sure it will work out.

As I come downstairs, Father smiles at me. "There's my little Buttercup," he says happily, coming towards me, intent on ruffling my mane with his hoof.

"Don't mess my mane!" I whine, backing up. "It took me hours to tame it!"

Mom laughs from the kitchen. "You know how mares are about their looks, Storm Wind. Don't mess it up for her."

Father looks at Mom. "But Daffodil, I just want to say goodbye to her!"

"You don't need to muss her mane to do it."

Father sighs. Leaning forward, he kisses me on the forehead, making me smile. "Have fun, sweetheart."

"I will!" I say happily.

As I turn to leave, I hear Mom whisper, "And so will we, right Storm?"

Father's wings pop open.

Grown ups are weird.

Stepping outside, I can see that the sun has set and the moon has risen. Lights are on in many houses. I decide to start at the outside of town and work my way in. That way, I can see the whole town and meet lots of ponies-

"And where are you going, silly filly? Buk-CACK!"

"Gah!" I jump and hide behind my bucket. It's the frighteningly friendly pink pony, and she's dressed as a chicken! "I-I-I-I-I-I-" I stammer away, scared.

"Your parents asked me to watch you along with the other colts and fillies tonight!" she says happily. "We gotta stay as a group, after all!"

I blink, seeing the other ponies behind her. There are fillies and colts my age. Maybe I can make friends. "Uhh...okay..." I step out from behind my bucket, picking it back up.

"Okie-dokie-lokie!" she says loudly. "Follow me, everypony!"

I let the others go ahead of me. I see a lot of interesting costumes. There's a marewolf, a vampony, a mummy, a few zomponies... I begin to feel a little unimaginative in my princess costume. I stare into my bucket, hoping nopony makes fun of me or anything like that. It's just that story Grandpa always reads me...

"She can be right scary when she gets friendly, can't she?" a voice asks me.

I look up. A white and brown colt in a pirate costume is smiling at me. I smile shyly back. "Umm...who?" I ask.

His visible brown eye twinkles. "Pinkie Pie, a'course. She can be a bit blinkered when it comes to making friends, but she's a'right once you get to know her." He chuckles a bit. "A bit barmy, but a cracking party planner. Also a great friend in a pinch."

I smile. Something about him is...calming. "I'm Buttercup," I say quietly.

He puts his hoof against his face. "Oy! Where'd my manners get ta? I'm Pipsqueak the Pirate, at yer service!" He gives a comic bow. "How may I assist you tonight, oh fair Princess?"

Giggling, I curtsy in return. "It would be an honor, gallant sir, if you were to accompany me on this fair night."

"Smashing!" he replies happily. "Come along then!"

As he walks off with the rest of the group, I happily follow, glad it looks like I made a friend.

At the first house, Pinkie knocks on the door for all of us. I look towards Pipsqueak. "What do I do?" I ask.

He smiles at me. "Just chant along with everypony else. No worries."

I smile back, my confidence bolstered by his words. As the door opens, I chant with everypony.

"♫Nightmare Night, What a fright,
Give us something sweet to bite."

The pony who answers the door smiles, passing out candy to all of us. With a big grin, I follow everypony else as Pinkie Pie leads us to a big farm at the edge of town. We walk up until we bump into an orange mare in a scarecrow costume.

"Howdy, everypony," she says happily, "and Happy Nightmare Night! Ya' all ready for the 'hayride of terror'?" She says this last in a somewhat spooky voice.

I shiver slightly, staring up at her afraid. Pipsqueak nudges me slightly, making me jump a little.

"Calm down, gel," he says with a smile. "The grownups won't let nothing happen to us tonight. It's all on the up and up, perfectly safe."

I smile back. "I-if you say so." I join him and the others as we all climb into the hay cart. A large red stallion pulls the cart. We ride through an orchard, decorated with holiday themed streamers and other objects. A few gravestones startle me, but Pipsqueak points out to me that they're foam props. As I begin to recognize the fun in the scary side of the holiday, I begin to enjoy myself a bit more. However, I still scream a bit and duck when the swarm of fruit bats in dark blue, purple, and red burst out of the trees and wing over us. Pipsqueak holds his sword in his mouth over me, swinging it back and forth protectively. I find myself blushing at how dashing he looks as he does so, so very brave and chivalrous.

After the hay cart ride, Pinkie Pie leads us back into town. I see that a lot of games have been set up, and I smile. I hope I get to give a few a try. Since the group seems to be splitting up, I stick close to Pipsqueak.

He looks at me. "You alright there, Buttercup?"

I look away. "I don't know many ponies yet," I say softly.

"That's alright," he says in reply. "I'm still pretty new myself. Glad to be your first friend." He smiles again. "Come on! Let's check out the spider toss."

Smiling, I follow him, eager for fun. He goes first on the spider toss, managing to throw the spider into the net, sticking to the top of it. "Alright. You're up."

I step forward. The stallion running the game chuckles. "Toss the spider as close to the center of the net as you can. Think you can beat your little coltfriend?"

I blush at that. I just met him, after all. In my embarrassment, I throw the spider harder than I intend to. It strikes the center of the net dead on, stretching it all the way back before it launches off and slams into the back of the stallion's head. The force of the impact knocks him head over fetlocks onto his back on the floor. "...last time I let Pinkie Pie build the attractions..." he groans.

I stare. "Is...is he going to be okay?" I ask.

"No worries love," Pipsqueak says easily. "Pinkie never builds anything actually dangerous. Come on, let's go get more candy!"

Smiling, I follow Pipsqueak from one house to another, gathering more candy. However, he was obviously collecting for a while before I joined the group, since his haul is quite a bit larger than mine. I don't mind all that much. After all, I don't need that much candy. After a time, he leads me back to the group, gathering around a scary looking zebra. I've seen zebras before in Father's shop, but they've never had spiders in their manes. I move closer to Pipsqueak.

He smiles reassuringly at me. "Don't worry, Buttercup. Zecora's not all that scary. She just gets dressed up for the holiday like everypony else. She's gonna tell us the story!"

I smile, but my smile doesn't last. I've heard the story of Nightmare Night - the costumes, the offerings of candy to Nightmare Moon, and everything else - but I've never heard it told in such a spooky voice before, and the rhymes make it even more frightening. However, Pipsqueak's reassuring smile gives me the confidence to keep going...until I see the statue of Nightmare Moon. I've never seen one before, and the reptilian eyes, the sharp teeth, the lifelike colors...I shiver violently as I pour the candy out before the statue along with the others.

Then the statue bends over towards me. "Your offering is pleasing to me," it - she, it's the real Nightmare Moon I see by the billowing mane and tail - says, her voice echoing. "Perhaps I shall eat it instead of you!"

The others scream, running back towards the bushes. I'm too scared, my muscles locking up as I tumble over.

"What's this?" she cries out, leaning closer to me. "Not running? Could it be that you want to be eaten?"

Whimpering, I curl up, shaking in fright, struggling not to cry.

"Have no fear, Buttercup!" Pipsqueak yells out, leaping between me and Nightmare Moon. "I'll protect ya from the evil monster!"

I look up. Nightmare Moon has taken a step back, seeming confused. Pipsqueak stands between her and me, brandishing his sword. Pipsqueak makes some sort of motion with his head, and Nightmare Moon suddenly grins. "Do you think you can stand against me, foal?" She lunges towards him.

He dances back, staying between her and me. "No honorable pirate would leave a maid in distress!" He lunges forward, pushing Nightmare back. "Besides, I have a secret ya don't know!"

Nightmare Moon snarls. "Oh? And what, pray tell, might it be? You aren't left-hooved?"

Pipsqueak grins fearlessly. "Well, that too. But this ain't no ordinary sword!" He pops the blade off his wooden sword.

"What?" Nightmare Moon asks, shocked.

Pipsqueak poses dramatically. "It is really the all powerful, mystic...sword of light!" He flips something on the handle and a beam of light shoots out from the hilt, illuminating a spot on Nightmare Moon's chest.

"NOOOOO!" Nightmare Moon cries out, writhing as though in pain as Pipsqueak holds the light on her. "And I was so close to resurrection! I will have my revenge!" With a flash of light, Nightmare Moon seems to explode...and Princess Luna appears as the light fades.

"Huzzah!" she proclaims. "Well done, young friend Pip! You have freed me from Nightmare's grasp once again!" She smiles down at me. "But it appears that this time, the rescued princesses have been doubled!"

Pipsqueak chuckles. "Sure does, Princess Luna. This is my friend Buttercup! It's her first Nightmare Night in Ponyville!"

"Umm...first Nightmare Night ever, actually," I hesitantly correct him. Since I never left Father's stall when I dressed up to help with sales on Nightmare Night, it seems accurate to me.

Princess Luna frowns, looking upset by something. "You mean...you are not familiar with the 'scary but fun' tradition? I...truly frightened you?"

"But it wasn't you who was scary," I say, confused. "It was Nightmare Moon."

Princess Luna and Pipsqueak look a little nervous. "Nightmare Moon was never here," the Princess admits. "It was me the entire time. I assume the form of Nightmare Moon to enhance the scary fun for the fillies and colts. I had thought...that you wanted a greater fright thrill. It was not my intention to give you true fear. My deepest apologies."

I blink, processing this. Then I turn to Pipsqueak. "Did you...know about this?"

Pipsqueak nods. "Yeah. Prin- Luna's my friend. She'd never hurt us."

"Hold not his foreknowledge against my young friend, I beg you," Princess Luna says to me. "As well as I know him, I believe it was his intention to enhance your experience in a more fun way, watching him slay a monster to save you." Pipsqueak nods at her words. "Besides, I know him quite well. Even had my threat been real, he would have leapt to the defense of his friends without hesitation."

Pipsqueak rubs the back of his head with his hoof. "I guess I'm just reckless that way," he admits.

"I would say courageous," Luna corrected.

"Aww, Luna!" He covers his cheeks. "You're making me blush."

I smile as I notice the final sign of the charade. The 'all powerful, mystical Sword of Light' is actually a glowstone in the base of the hilt. He had made the base out of a flashlight. I come up to him. "Well, my Dread Pirate, I think you were quite gallant." Leaning in, I give him a light kiss on the cheek, making him blush further.

Luna laughs. "How wonderful! The true reward every gallant hero longs for, so nobly granted. Oh, this is truly the most wonderful of nights!"

I can't help but giggle, blushing at how the Princess put it. Princess Luna then scoops us both up onto her back, and races back into the main part of town. I hadn't realized that Zecora had led us out into the forest. She then engages in many of the games, pulling us along for the ride. It is quite fun.

After a time, however, the merriment and festivities start to die down. Pipsqueak smiles at me. "May I walk you home, Princess?"

I giggle. "As you wish, Dread Pirate."

He suddenly blushes. I look at him confused for a moment, until I recognize my wording and blush as well. At least his name isn't Wesley, I think to myself, remembering Grampa's story.

After we get over our embarrassment, I lead Pipsqueak to my house. Once there, I try to open the door, but it's locked. Frowning, I knock. When there's no response, I try to knock louder. Glancing in, I see the lights are out, and sigh. "It looks like my parents feel asleep after playing Twister, or wrestling, or something like that."

Pipsqueak blinked at me. "You mean you're locked out?"

I nod sadly. I see him reaching into his candy bag. "What are you doing?"

"Just a sec...aha!" He pulls out a quill, an ink pot, and a parchment scroll. "Twilight sometimes slips school supplies in with the candy." He begins writing something on the scroll. I glance over and read it silently.

The dor was lucked and Buttercup couldn't get in.
We made frends, so I took her to my place for the night.

He scrawled an address afterwards.

Didn't like the idia of my frend being locked out at night.
Come by to pick her up tomorrow morning.
Pipsqueak the Pirate, age 7.

Finishing the note, he slipped it into the mail slot. "They'll see it when they wake up."

I smile sadly. "I don't think they meant to do it. None of us are used to having a set address with a door that locks yet."

"Don't worry about it," he replies. "I'm not gonna judge. Come on, you can sleep at my place. My family won't mind."

Smiling, I follow him to his place. "Nice place," I say, seeing the three story house.

He shrugs. "It's just our place in town. We don't really use it much, since transportation's no issue for Mum or Da." He steps onto the welcome mat. It glows green for a moment, and something pops out of the doorframe at mouth height on him. He speaks into it. "Pipsqueak the Pirate," he says clearly.

Several large metal structures, obviously weapons of some kind, pop out of the side of the house, pointing at me, startling a yelp out of me.

Pipsqueak glances towards them, then says into the device he spoke into before, "And guest." The metal structures withdraw back into the house. "Sorry about that. Da's got tons of cool toys that make big booms since he likes them, and Ma's kinda security paranoid at times."

I catch my breath. "It's okay. I'm fine." While it was unexpected, I try to file it under the 'scary but fun' of Nightmare Night as the door swings open.

Pipsqueak leads me through the house to the third floor. "My room's up here, since I like high places." He opens a door.

Inside, I gasp. His bed is a full fledged miniature pirate ship, complete with crow's nest and rocking motion reminiscent of the waves, although it's not large enough to sail in. "Wow!"

Pipsqueak smiles dismissively. "Da has weird ideas about furnishings, but I like it." He climbs up to the crows nest happily. "You can use the bed on deck."

I climb onto the deck, crawling under the sheets. It is actually surprisingly comfortable, and I curl up easily. However, I notice something quite quick which will make it hard for me to sleep. "Umm...Pip?" I call. "Do you have any...plushies?"

Pipsqueak glances down at me. "Nope. Never needed 'em. Why?"

I blush. "Umm...I need something to cuddle up to, or I can't sleep."

Pipsqueak leans back, thinking. "Hmm...I know Ma and Da don't have any...even if big sis has some, she'd kill me if I touched her stuff...oh! I got it." He shimmies down the mast and ducks into the covers beside me.

"P-pip?" I ask, shocked.

He smiles at me. "You said you needed something to cuddle up to to sleep? Will I do?"

I blush happily. Leaning in, I kiss him lightly on the cheek. "Thank you," I say, curling up to him as I almost immediately begin to drift off.

He blushes, then curls around me. "Good night, Princess Buttercup," he says with a smile. "Sweet dreams."

And sweet dreams to you, my Dread Pirate prince.