Derpy's Vest

by Michael Hudson

Rating: teen
Tags: Sex, Comedy, Derpy Hooves, Slice of Life, Anthro, My Little Pony: Friendship is Magic
Length: 2979

There's just something so interesting about Derpy's vest today, not that anypony can place it of course.

Off to her normal day of work and deliveries, Derpy throws on her vest, just like any other day, so why is everypony always staring at it?

Thank you to my patrons for voting on and supporting this story.

Published 2016-10-01 17:00:02 UTC
Last updated 2016-10-01 17:00:02 UTC

It's just so... blue.

Derpy stopped for a moment as she got to the door to her house. A gentle breeze was blowing through the small, loud shack that she liked, due to the fact that she liked to leave her windows open, though today, the breeze was a touch uncomfortable. Not that she hadn’t expected it.

She looked to the full length mirror that rested by the doorway. She usually used it to make sure that she had everything she needed. Her mailbag, her vest, etc. This morning though, she didn’t really see the necessity for it, as she’d spent the whole morning making sure she had everything. Now she merely had to get to work.

She shuffled her hooves for a moment, still trying to figure out what might be wrong, before she looked back into the mirror. Her reflection looked back, before giving her a nervous smile. They’d discussed this last night in the bathroom, and for a long time at that. How it reflected how open they were, how it was more comfortable, and how she wasn’t breaking any rules, at least not for her job.

She looked back to the door, before smiling a touch wider. The weight on her chest began to shift as she remembered the last bit that she’d forgotten to bring up last night. The idea of what others would think of her choice.

But when you’re a clutz, destructive, and already pitied, there wasn’t much further down one could go, and she had long ago learned to ignore what others thought of her. So, with a flick of the wrist, and a check of her list of packages, she headed for-

Fluttershy

The shy mare jumped as a gentle knock came against her door. Fluttershy wasn’t expecting anypony today, so she started rattling her brain for what it could be. First option was that she had forgotten something, but looking at the calendar that hung beside the door proved that untrue. Next was her duty as an element bearer, which she dreadfully hoped wasn’t the case. She always was willing, but the journeys were long, and usually scary to some degree.

“Package for you!”

The voice lifted Fluttershy’s heart, as it simply meant some mail from a good friend. And, since she was making some morning tea anyways, she could even invite Derpy in for a touch of conversation. Just like she enjoyed it.

When she opened the door though, all of those thoughts flew away as her heart, stomach, liver, and really anything else leapt into her throat, and her brain said goodbye. She blinked a few times as she looked at her friend, her head feeling like it was boiling as Depy stared back.

The innocent, bubbly pegasus didn’t seem to take note of the issue as she held out a clipboard to her, a small box resting on one of her wings. “I hope your morning has been going well, Fluttershy. Mine’s been pretty good so far.”

Fluttershy swallowed hard as her brain began to work again. Not that she could actually say what was on her mind, even if it might make sure the other pegasus didn’t get embarrassed. So, instead, she simply took the pen, and mumbled, “Good,” as she signed for the package.

Derpy nodded, before frowning a bit, stepping forward, and placing a hand on Fluttershy’s head. “Are you okay? You feel really warm.”

Fluttershy thought she might have a heart attack. They were touching. They weren’t supposed to be touching. They couldn’t be touching.

Her hand shot forward, grabbing the package as she whispered, “Thank you for the package, it was nice to see you, bye,” and then slammed the door hard enough to shake the whole house.

Derpy stared at the door, before shrugging. She had never quite been able to peg her shy friend, and this must be one of those times. She did stop for a moment as she heard a thud from within the the house, but decided that instead of Fluttershy passing out, it must have just been her dropping the package, or something like that. Besides, she had other people to see.

Thunderlane

The self proclaimed ‘Stud of Ponyville’ grinned to himself as he heard those sweet words come into his house. The words that meant he got to see one of the best racks in Ponyville on his doorstep, and watch that big ol’ booty fly away.

Of course, they belonged to Derpy, so he kept his distance. Sure, she might be nice to bang, but if anypony found out he had made her a one night stand, they would probably castrate him. And making her a friend with benefits would be damn near impossible with how innocent she was. Besides, he had less troublesome mares he was already working on in the town, rather than one who could single handedly destroy your house on accident.

Or, at least, he had other targets until he opened the door. One look at Derpy in her vest though, and he knew he just had to have at her muffin tops. Once he got over the initial shock, he leaned against the door frame, a large smile spreading across his face. “Hey, how you doin’?”

Derpy tilted her head at the weird tone he had used. Sure, Thunderlane usually was a bit weird, hence why she could even join in on the jokes that the other mares told, at least, the ones she understood, but he sounded like he was almost from Manehatten with whatever accent he was putting on.

A shake of her head got her to come back to reality, and she extended her pen and clipboard to him. “I need you to sign here.”

Thunderlane nodded to himself. This was a good sign. She’d already become flustered by his charm, just as an inexperienced mare like her probably should. Now he just had to keep working it. “Say, you’re looking pretty good today. New vest?”

Derpy let out a little giggle at the obvious joke as she grabbed the blue fabric. “No, though I am coming up on five years of service, so they’ll be giving me a new name tag then.”

Thunderlane forced himself to nod with interest, instead of just rolling his eyes. He didn’t really care about her work history when she was like this in front of him. Celestia only knows when it would happen again. “Well, I’ll say that it looks a bit chilly in that. Maybe you want to come inside for a bit?”

Derpy shook her head. “I’m good, but thank you. Now, please, will you sign. I have a couple of other packages I need to get to, and I don’t want to keep their owners waiting.”

Thunderlane slightly panicked at the excuse. Derpy liked stopping to chat normally. Did she know? No, that couldn’t have been the case. He frowned slightly as he scribbled down his signature. “Are you sure? Not even like… ten minutes?”

Derpy thought for a moment as she gave him his package. This sounded familiar, from times when she’d hung out with Roseluck and Redheart. What did they usually say to him giving time estimates? Oh yeah! “You, um, wouldn’t last long enough?”

Thunderlane’s blood boiled at the comment, but he had to force himself to smile. If he didn’t the vest would never be his. Instead he simply began to close the door, and said, “Well, you have things to do, and so do I,” through clenched teeth.

Derpy blinked a few times at the action, before shrugging, and taking off. Maybe one of her mare pals would be able to tell her later what that was all about.

Button Mash

The excited, young colt was practically bouncing in front of the door as he waited for Derpy to arrive. His Playstation 4 was supposed to come in today, and he couldn’t get it soon enough. He just hoped that it wasn’t going to be damaged. If it was anything like the Playstation 3 though, a system him and Rumble had somehow not destroyed, not even Derpy should have been able to break it.

On the other hoof, it was Derpy…

Ding dong.

Button shot forward, yanking the door open. What he saw though, shut everything off except one part of the young colt.

Derpy, for her part, simple bent down, bringing her vest down, and causing it to shake a little from the wind generated by the sudden movement. “I noticed what you got, and congratulations! I know you’ve been saving up for a while now to get it.”

Button slowly nodded, unable to take his eyes off of Derpy, even as he got the clipboard. He didn’t even know what she was talking about, let alone why he was signing something.

Derpy merely smiled, handing the larger package to Button Mash with a wink. “Well, if you and Love Tap ever want, remember that I always want to get better at games, and that I love hanging out with the two of you.”

Button nodded again, his eyes glued to her, even as she flew away. Only once she was out of his sight did he realize what she’d said, and shouted, “Mom, can we have Derpy over tomorrow?”

Love Tap glanced out of the kitchen, an eyebrow raised. Button was good friends with Derpy, and she herself considered the clutzy mare to be one of her best friends, but it was rare for him to think about bringing her over. When she saw the package in his hands, she had a feeling as to why. “Alright, I’ll call her up later. For now, you don’t get to play that before you do your homework.”

“But mom!”

Applejack

Derpy bobbed her head, having heard a song on the way, and getting it promptly stuck in her head. Not that she minded though, as she definitely needed something like this for when she came to Sweet Apple Acres. The chance of not having to hunt down a family member in the fields was usually pretty low.

Luckily, to some degree, she got lucky today as Granny Smith opened the door. The old mare looked at Derpy, before letting out a loud laugh. “Well, I’ll be. You’re looking quite nice today, young mare.”

Derpy let a small blush come over her cheeks at the compliment from her elder. “Ah, please Granny, I’m not really wearing anything special.”

Another bark of laughter came from Granny Smith. “Yeah, and that’s what I used to tell the boys when I tied up my shirt too. Ah, those were the days, when I could flaunt like you are.” She then bit into her cheek, and yelled back, “Hey, Apple Bloom, I want you to come here. I think Derpy has the right idea for you to get the attention of that dancing colt you say you like.”

Derpy’s face became brighter, especially as she thought about giving dating advice. She was lucky to have what she had, let alone figuring out how to get another pony a special somepony. “Please, Granny, I’m not trying to flaunt myself or anything like that. I’m just dressed like this for, well, my own reasons.”

Granny glanced at her for a moment, before cracking a grin. “Well, I suppose for a mare like you, it makes sense. Don’t go giving too many stallion’s the wrong idea though. Some of us already have too much competition as it is.”

“Granny, go back inside, and stop harassing Derpy about your lov li-” Applejack stopped as she turned into the doorway and felt her heart skip a beat. “D-Derpy?”

This was something that was easier for her to deal with, especially since the package was addressed to Applejack herself. “Yep, that’s me! Unfortunately, I do need you to sign this. Though, you’re my last stop before I need to just deliver some letters, so if you want me to come back afterwards-”

“Oh, I bet she would love you to. She could even try out her package with you.”

“Granny, shut up!”

“What did you want me to see, Granny?”

“Apple Bloom, to your room, now!” Applejack was not about to let anything worse happen though, and scribbled her signature down faster than Derpy had seen anypony do before, before slamming the door shut.

She tapped against the long, rectangular box that Applejack forgot to take, but decided against knocking again. They seemed to be under a lot of stress after all. So, she left the package on the doorstep, and flew off, her mind on where she would go after she got the letters in their respective mailboxes.

And frowned.

======+++++======

Derpy slipped her vest off as she came to the smaller farm house. It wasn’t anything like the Apple Family’s, sure, but it was still nice and quaint, and would grow with the years to come. One pony couldn’t handle a whole orchard anyways.

Of course, those thoughts were only at the very fringe of her mind. For the first time since she had left her house, she was nervous, and held her folded up, blue vest to her chest. She knew she should’ve talked to the mare she now would see before she had gone with her choice, but Derpy had been too afraid.

Now that she’d done it for a day though, and found it mostly successful, she knew she couldn’t put it off anymore.

After a small knock, the door opened up to the familiar, yellow mare that Derpy had been seeing for the past year: Carrot Top. The farm mare blinked a few times, before pinching the bridge of her nose. “Derpy, you’re naked.”

“I-I know.”

“Look, I don’t care if you don’t…” Carrot Top looked down and into the scared eyes of her special somepony. “Wait, you know? But you never know what you did wrong.”

Derpy dug the edge of a hoof into the ground as she looked away. “It-It’s because I chose to do this. It wasn’t an accident.”

Carrot’s eyes widened, before she creamed, “What? You know you’re letting everypony see literally everything on you, right? And don’t tell me that you still wore your vest or something, as I know they can’t hide those giant tits of yours! What were you thinking?”

Derpy tried to mouth something, but unlike with everypony else, all she could do was look down. Her body began to shake as she begged for some way to explain to Carrot why she thought this was a good idea, but she just couldn’t, no matter how much she hated that fact.

Luckily, Derpy had a good marefriend. One who had been there for all of her mistakes. Who knew that Derpy was an odd mare, but that she always had some reason, and never did anything in an attempt to hurt another pony. And now, she could see that this mare was crying, and needed her.

Carrot Top wrapped her arms around Derpy, gently shushing the hurt pegasus. “It’s okay Derpy. I was just shocked, and… Well, I still need a reason, but I promise I’ll listen.”

Derpy looked up into Carrot’s eyes, and managed a small smile at the words. She just had to say her case right.

Which did not fill her with confidence.

“Well, you see, it all started with that fancy party Rarity asked us to. They all liked the dress I wore, while it constricted me, but comfort isn’t the issue. Well, I mean, being like this is comfy, but that’s not the real reaso-”

She stopped as Carrot placed a finger on her lips. “Just tell me why.”

Derpy fidgeted for a moment, before breathing in, and resolving herself to this. Carrot wouldn’t hate her for this after all, so why should she be so afraid? “I feel like this is me. I like being open, honest, and not hiding anything. To feel the air on my skin though, the sun on my bosom… It’s all a plus, I guess.”

Carrot Top shook her head for a moment, before giving Derpy a small squeeze, and leading her inside. “Alright. If it makes you feel like you, and you aren’t going to start sharing yourself… I really see no reason to stop you I suppose.”

Derpy smiled at that, before nudging Carrot Top with her head. “Hey, let me make you something, to make up for it, and let you process. Alright?”

Carrot Top nodded for a moment, before she heard the phone ring. She rolled her eyes at the introduction, before stepping away from Derpy. "I'll get it."

“Hello, Carrot Top of Carrot Farms speaking. Oh, hey Love Tap. Yeah, Derpy is here, why do you ask? Oh, Button wants us to…”

“Tell me, did Button see Derpy today? And did you? Well, I mean, it doesn’t matter, so long as you don’t mind indulging in Button just wanting her over because she’s a nudist now.”

Carrot Top smiled to herself as she heard screaming on the other end, and suspected that, at least for a while, she might have to deal with a lot of calls like this. Looking at that bubble butt shaking in her kitchen though, she knew it would all be worth it. At least, so long as she got her at the end of the day, and only her.

Derpy turned around and raised an eyebrow. “What was the call about?”

Carrot Top smiled. “Nothing. At least, nothing that you’d ever worry about.”

Derpy blushed at that as she turned back towards the stove. “Sorry.” She jumped as two, strong arms wrapped around her, before she laid back into her lover’s arms.

Carrot Top gently pecked Derpy’s head, before whispering, “Nothing to be sorry about, not when it’s why I love you. Vest and all.”