The Cloudsdale Trick O'Treat Extravaganza

by CanterlotGuardian

Rating: everyone
Tags: Derpy Hooves, Princess Luna, My Little Pony: Friendship is Magic, Comedy, Other, Romance, Random
Length: 1651

Luna and Derpy go to Cloudsdale for fall festivities.

When Princess Luna decides to go to Cloudsdale for their annual Trick O'Treat celebration, she has to bring another pony with. So what's going to happen if that pony just happens to be the one pony she's ever had feelings for? Things might get interesting...

Especially if her partner is Ponyville's official mailmare.

Published 2012-10-24 01:40:02 UTC
Last updated 2012-10-24 01:40:02 UTC

Here, The Fun Be Doubled!

Author's Note: I couldn't help but have P3RROHAMBRE's story M0re Than Gam3rs in the forefront of my mind as I was writing this, for a few reasons. One, it's quite possibly my favorite My Little Pony fanfiction ever; and two, it's the story that got me liking Luna and Derpy as a pairing, in the first place. Thus, why I'm writing this story the way I am.

Enjoy!

The sun dipped into the horizon, though its life-giving light and warmth were still present in the world. It would not be so warm for very long, though; autumn had come at last, and the chills of the impending winter were starting to make themselves known.

Celestia looked out at her handiwork as the last arch of the sun disappeared. As if on cue, the moon began to rise as the skies darkened and the stars came out for their turn in the grand scheme of things. She smiled and turned to her left, as her sister came up to join her on the palace balcony.

“Are you ready for tonight?” Celestia asked, a sly grin coming over her face.

“That, I am,” Luna replied with a grin. They both knew what that night had in store for them; it was Cloudsdale’s annual Trick O’Treat night, where ponies gorged themselves on candy and fun, and prepared themselves for the Nightmare Night celebration later on in the month.

“Do you have your special ponyfriend to go with you?” Celestia inquired.

Luna shook her head. “Nopony hast said anything about wanting to go with me…”

“I’m sorry…” Celestia replied. “If I knew of anyone that would possibly want to, I would tell you. I would recommend my student, but she is already attending with me.”

“That is something I wanted to inquire of thee. How is your student planning on going to the skies tonight, seeing as she hast not wings like us?”

“This is true,” Celestia replied, “but she does have magic, and I do believe she will be casting her wing-making spell for the trip up there and back.”

Luna was about to respond, when a cry could be heard from a short ways off: “Incoming delivery!!” The two alicorns separated to allow the mailmare enough room to crash-land onto the balcony as she always did. She skidded to a halt, her back legs comedically draping over her eyes. She grinned her usual lopsided grin.

Luna couldn’t help but laugh. “Ah, my dear Derpy. To what do we owe the privilege of your company tonight?”

Derpy got up and fluffed her coat back into its proper place. “I’m stopping by to drop off a package for Princess Celestia.” She got the box out and walked over to the Princess, respectfully placing it at her hooves.

“Ah! That’s probably the gift I ordered for my dear sister for her birthday.” Derpy looked over at Luna, who was a bit in shock. Celestia usually didn’t get Luna anything for her birthday, so for her to do so this year was a bit out of character.

Suddenly, an idea came to Celestia. “Say! Why don’t you and Derpy go to the Trick O’Treat party tonight? It’ll be fun!”

“Ooh, I’d love to! I’ve never been there before, and I can actually go this year!” She looked to Luna expectantly. “Do you want to?”

Luna was glad her dark coat was hiding the fact that she was blushing. She’d always had a thing for Ponyville’s mailmare, and no one had ever found about that secret. Now, the object of her affections was asking her if she wanted to spend the entire night alone with her? It seemed almost too good to be true.

“Surely,” Luna replied. “It would be a true honor to be able to accompany you tonight, Derpy.”

Derpy’s face lit up like a Ponymas tree. She jumped into the air and cheered, then ran up to Luna and hugged her around the neck. “Tonight’s gonna be the best night ever!”

Later on that night, Luna and Derpy walked side by side on Cloudsdale’s streets. Unfortunately for them, they weren’t alone.

“I’ve only been up here once,” Pinkie Pie was saying with awe in her eyes. “This is gonna be so awesome!!!”

Luna looked at Derpy. “I pray thou tell me, my friend… Why is the pink one with us tonight?”

“You heard what Celestia said, Princess,” Derpy replied. “She needs to get out and experience other cultures. That, and the only other option was for her to stay with the Cakes tonight, and Celestia was supposed to be going with them to the Trick O’Treat event… and, well, quite frankly I don’t think Celestia was up to being annoyed by Pinkie Pie all night.”

“Cheer up, silly Princess!” Pinkie Pie exclaimed,  bounding over to them. “I won’t be too much of a burden on you! We’ll have a blast!”

Luna tried to put a genuine smile on her face. “I believe it.”

As they walked along the street, they began to see all of the costumes that the ponies were dressed up as. Derpy waved at Rainbow Dash, who was flying above everyone else, clad in a home-made Daring Do costume.

Suddenly, a pony appeared out of nowhere in front of them. He was dressed in a red and black jumpsuit, with a pair of swords crossed over his back.

“Ooh!” Pinkie cried out, obviously interested in this new pony. “Who are you supposed to be?”

The stallion grinned. “I’m Deadpony, of course! The Mare with The Mouth!”

Luna looked to Derpy for some kind of explanation. “What is a Deadpony? If a pony is dead, how can they be still walking around?”

Derpy looked over at Deadpony, and saw that he had suddenly been joined by a somewhat familiar character, hooded face and all.

“Look, Princess!” Derpy said, pointing to the pair. “Recognize the other one?”

Luna, as much as she didn’t want to, looked away from Derpy. Her eyes grew wide. “New pony… Are you not the one they called Mare Do Well? And where is the pink one?”

“Enough questions!” Deadpony suddenly exclaimed. “Away… FOR JUSTICE!” He darted off, with Mare Do Well hot in pursuit.

Luna looked up to the mid-night skies. “Is this what I missed during my exile…? This… random chaos?”

“It’s all in fun,” Derpy replied, looking around. “Ooh, hey! They’ve got candied apples over there. Want to go get one?” The prospect of eating something with the mailmare was sounding very appealing to Luna, so she nodded in assent.

A few moments later, they were crunching away happily on the freshest candied apples that either of them had ever tasted.

“Well!” Luna exclaimed after she’d finished hers. “That was extraordinarily delicious!”

“I see that,” Derpy replied. “You ate the core and everything!”

Luna looked down at the stick that had once had the candied apple impaled on it. Sure enough, the core was gone.

“Whoops…” she murmured. She hadn’t really been paying all that much attention to how she was eating; she’d been too busy thinking about the rest of the night, and being able to spend it with Derpy.

“It’s fine,” Derpy replied, smiling. “Hey, do you want to go Trick O’Treating next?”

“Are we not already doing that? Being here at the festival?”

“Well a bit, yeah, but it’s a totally different activity! It’s the highlight of the night! We go out to all the different houses and they give us candy! Just for coming to them! It’s awesome!!”

Luna couldn’t help but share in her friend’s enthusiasm, even if his exclamations did remind her a bit much of Pinkie Pie.

“That sounds like a grand time,” Luna replied. “Let us go forth!” Derpy grinned, and they grabbed two bags that had spontaneously appeared beside them. They started walking off towards the nearest house, music that had nothing to do with the scenario beginning to play as they walked.

It was almost morning by the time the pair got back from the Trick O’Treat festival. They had ended up Trick O’Treating for almost five hours, Luna was having so much fun with it. Derpy didn’t mind, really, especially not since they’d ended up with so much candy that Luna had had to carry it back with them using her magic.

When they landed on the balcony, Derpy yawned. “I’m glad I don’t have to go to work tomorrow. Scribe and Quill are taking over for me tomorrow, since tomorrow’s my regular day off anyways.”

“Tonight was the grandest night I have had in years,” Luna declared. “And, I dare say, it had much to do with you.” She smiled. “Being with you tonight was better than I could have ever thought possible.”

Derpy smiled back at her. “I feel the same…” She swayed on her feet a bit. “Well, I’d better get going back to the house; I’m really tired-“

“Why not just stay here tonight? With me.”

She now had the mailmare’s total attention again. “Really? Here, in the Canterlot palace?”

“Hast thou not seen mine bed? There is more than enough room for both of us.”

Derpy smiled and nodded tiredly, and the two of them walked inside. Luna deposited the candy by her dresser, then hopped up onto the bed. She patted the bed beside her, and Derpy got in.

After they were situated underneath the covers and comfortable, Luna turned to say something to Derpy, when suddenly the mailmare laid her head on her shoulder and snuggled up to her. Luna could tell that Derpy had immediately gone off to sleep.

She smiled and closed her eyes, drifting off as well. Her last thought before going to sleep was how perfect the night had been and-

“Wait. Something is not right… How did the pink one even get up there to begin with?”