You're Probably Wondering Why I'm Wearing a Maid's Dress...

by Tiki Bat

First published

A Stallion down on his luck has an interesting story behind why he's wearing a maid's dress of all things...

You ever just have one of those kind of nerve wracking conversations where you have to explain your job to some other pony that might not understand it?

Yeah, that's what I went through when I met one of my good friends, and believe me, it's never easy to explain why me, a stallion, is wearing a maid's dress to work, especially to a new friend that you're trying to make a good first impression with.

Just a silly one shot inspired by a picture drawn by lRUSU, which was in turn inspired by something I made in response to my passion project picking up comments more regularly. I told someone I'd draw my OC wearing a maid's dress if it ever picked up regular comments, and lo and behold it managed to do that shortly after as if the universe had willed it into existence.

... and It's Kind of a Funny Story!

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You ever wind up in that weird situation where you have to explain your job to another cute pony and you don’t know how to say it without sounding weird? Because that’s the exact situation I was in when I first met my friend Sheila. We hit it off well enough in passing, but I always got some weird looks whenever I was dressed for work, especially after work, but I guess it was inevitable that she’d see me that way. So why was this weird? Well that’s because I wore a maid’s dress everyday, you know, something like what a mare might wear… and I’m a stallion. It’s not the most uncommon or taboo thing in the world, and heck, there’s plenty of others that are into that kind of thing. But my situation was definitely unorthodox to say the least.

There we were, on a fine summer’s day sitting at some curbside cafe right in the center of Manehattan. Maybe not the best place to hang out if you were looking to avoid the curious glances of passing ponies, but eh, the Diamond Diner had good food and it was worth the casual embarrassment of dining after work in a frilly maid’s dress. I wasn’t deathly embarrassed about it, but I still wasn’t fully used to it, and the strange looks I got from her definitely didn’t ease my worries. I looked my companion in the eyes as I fiddled with the plate of hay fries that sat in front of me, being careful that my pristine socks weren’t messed up by the food.

Not wanting to delay the inevitable, I took a deep breath and began my unneeded explanation. “So… let’s just cut right to the chase, you’re wondering why I’m wearing a maid’s dress when I’m clearly a stallion… I can see that bewildered questioning look in your eyes, and believe me, I was in your horseshoes at one point too— It’s kind of a funny story though!”

Sheila slowly nodded, raising an eyebrow, “Uh huh… I’m sure it is. You know, it’s not really an issue though, I think it’s kinda cute.”

My face must have flushed red for a moment, before I regained my composure, “Well, I know, but I guess I just wanted to explain it. I don’t normally wear this kind of stuff, but it’s my work uniform.”

“Your work uniform? That’s a pretty unusual uniform for a stallion, I’m guessing there’s a good reason for it?”

I nodded, recollecting my story as best as I could “Oh believe me, there is. Kinda funny in retrospect too, as much as I’m still getting used to the idea,” I took a deep breath, taking some sips of water to help ease my dry mouth, “So this was a few days ago, when I was kinda strapped for some extra bits and a little desperate for a job. You see, I’m a graphic designer, or rather I guess I was.”

“A bat pony graphic designer? I’m gonna guess that didn’t work out for you, did it?”

“I know, I know. Weird job for a bat pony, but hey, it’s what my special talent is and it kept the lights on… or I guess did.”

“Let me guess, not a big market for that out here?”

“You think? I thought it was going to just wind up being the same as it always was for me. Jump city to city and find work wherever and whenever I could.”

“And it fizzled out when you hit Manehattan,” she deduced.

“Uh huh. It wasn’t the end of the world though, I had some cash that I could stretch out quite a bit. But that was never going to just work forever. So this is the part where you’d probably just run on home and find some other career to pick up, but unfortunately this place was my home.”

“Unfortunately? You really are a country pony aren’t you?”

I cocked my head to side, cursing my bad wording, “Unfortunately isn’t really the right word to use, inconveniently is probably more fitting. Turns out the job market for graphic designers in manehattan was pretty competitive and some hot shot newbie fresh in the city wasn’t going to stand a chance at getting picked up by some actual business, especially not a bat pony.”

“Rookie mistake eh?”

“Mhmm,” I agreed, “Silly me, thinking I could try my luck, this is Manehattan, not Los Pegasus.”

She laughed and shook her head, “So where does the maid dress come in? You don’t strike me as the fashionista type.”

“Har har, we’re getting to that. So I was out of a job, and needing one pretty desperately, so I did what any bat down on his luck would do, and trotted into the Helping Hooves Job Agency.”

“And then they got you a job as a maid?”

I shook my head, “Nope!.. Well, Okay, I guess they kinda sorta did in the end— but it wasn’t my actual job choice!”

“Oh? This outta be good.”

“Oh it is. As you might guess, the job market out here was reeeeeallly tied up unless you actually had some experience elsewhere.”

“And you had none… so they slapped you with the maid job?”

“Nope! — err, yes? Look, it’s complicated. I didn’t have any experience outside of my field, but that’s not why they gave me the job— or I guess not the full reason why. I trotted in and gave them my info, and more or less they said that my only options were working as the poor soul that has to go work in the sewers, or as a butler in one of the high end manors.”

“And you didn’t want to go work in the sewer?”

“Ha! No,” I laughed, “Yeah no, that didn’t sound appealing at all. Plus if I was already having trouble making friends out here, doing that would make it downright impossible.”

She considered this for a moment and nodded in agreeance, “Yeah, you got me there. So how’d you get from being a butler to being a maid? You lose a bet or something?”

“No… I uh just got a bad roll I guess. So basically I went and said yeah just give me the butler job, it’s better than nothing. The pony on my case did a little digging and said there was an opportunity opening up in the next couple of days and that she’d send me the information.”


“And I got the job!.. Well, sorta. So this is where the story gets funny. A few days went by and I got my job assignment just like they said I would… but there was a mixup.”

“Aha, so this is where the dress comes in?”

“Yep! Turns out that my file got switched with another pony’s somewhere along the way, but they had already settled into that position a day or two before me…”

“Which meant you were stuck with their maid position,” she finished.

“Mhmm, I was stuck with their maid position.”

“And you just stuck with it?”

“Well… I kind of had to,” I admitted, “That was the last job available that wasn’t the sewer worker job that’d cement my place at rock bottom, so I just had to bite the bullet and go with it.”

“And they made you wear that maid dress?”

“I mean they didn’t make me wear it,” I shrugged, “but my options were sit down and bite the bullet and wear it to my job because they had no real stallion uniform, or go work cleaning out the sewers so… Well, you get the idea.”

She laughed, “Oh I do. But hey, you seem to be handling it well enough. So, uhh… do you ever, well you know, get embarrassed wearing after work though?”

I let out a hearty laugh and nodded, “Oh no, I am sometimes.”

“So why wear it instead of changing for stuff like this?”

I shrugged, “What can I say? The dress is pretty comfy and it’s such a hassle to get out of.”

Sheila shook her head and chuckled to herself.

Just a Bat... a Bat Down on His Luck

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Now you're probably wondering how this all actually went down, at least from my perspective... the end of the story was a weird place to start, I know, right? But hear me out, you haven't heard the whole story yet, and as they say, it's not the destination, it's the journey that's the most important!

I was jobless, down on my luck, and desperate…

Oh, was I desperate.

How desperate are we talking though? Desperate enough that I’d take any job that I could hope to get my hooves on… well, almost any job. You see, I was a graphic designer, key word there, was. I mean I guess I still was, but you know, just unemployed. I had worked for years, climbing up from the bottom and working my way to hopefully the top, at least that was the hope. In reality I was just a freelancer roaming place to place and hoping I’d find something that would stick, and in my head Manehattan would be my gold mine.

So many businesses and ponies starving for ads, flyers, logos— everything you could imagine! And boy, were they hungry for content… imagine my luck though when it turned out that some hot shot freelancer would have little to no chance at getting scooped up here, but hey, it was little to no chance, and I just had to play my cards right and hope for the best.

So there I was, sitting in the lobby of the Manehattan Times, praying that this would finally be the job interview that’s work out for me, otherwise I’d have to make due with finding some job that’d pull a pony with pretty much no other experience in. That’s the ironic thing about getting your cutie mark that no one tells you about. You finally know what your special talent in life is and you’d figure out what you were good at, but sometimes you just got dealt a bad hand and all the good jobs were scooped up, leaving you scrambling to find something else.

A lot of ponies managed with this, but I wasn’t like most other ponies. I’m a bat pony, and it was just my luck that basically none of the good jobs were available at night. Sure, I could stay up during the day and completely flip my schedule on it’s head, but I didn’t want to, especially when my odds were pretty evenly stacked between the two. That’s why I was banking on this job more than anything. They needed a pony that could work through the night and get any designs and graphics drawn up for the early morning edition, and I was determined to be that pony! Even if it wasn’t the fancy job I had hoped for when I moved here.

“Next!” Shouted the receptionist at the desk, a deep purple unicorn with a blue mane pulled into a tight bun and a pair of narrow spectacles balanced on her muzzle.

I sat up in my seat and silently reaffirmed to myself that I was going to get the job. I would be the top pony and I wouldn’t have to scrounge around some job agency to find some low paying job. I stood up and trotted toward the desk, nodding as I came to a stop in front of her.

“You Stardust?”

“Sure am!” I nodded, trying to project as much confidence as I could into my voice.

“Alright, follow me. Hot Press is ready in his office, just finished up with the other applicant.”

“Perfect! Lead the way miss…”

“Morning Report.”

“Well lead on miss Morning Report.”

She rolled her eyes and muttered something under her breath about hot shots, but I didn’t catch the rest of it. Instead, I held myself high and followed along down the dimly lit hallway that I just knew would be my new workplace.

“So you work here long?”

Without glancing back, she replied, “Five years. Press’ office is that door at the end, just give it a knock and he’ll call you in.”

“Perfect!” I cheerfully replied, “I’m totally a shoe in for this job!”

“She let out a flat laugh and shook her head, “Good luck hot shot.”

“Thanks! I don’t know how much I’ll need it, but a vouch of confidence is always appreciated,” I replied back, reinforcing my confident facade.

I trotted toward the door as if I had walked that path thousands of times before. I wanted to look like I was the perfect pony for the job after all, and my would-be employer would definitely want to see a stallion that could carry themselves with confidence even if their qualifications were… slightly under the desired levels on the job listing. But those were just suggestions… right? I mean fake it ‘til you make it, that’s what they always said!

I stopped in front of the door and gave a hard, but not too hard knock, pulling the sides of my mouth up into what I could only assume was a confident smile, but in retrospect it probably looked fake and forced. It didn’t matter though, all I had to do was convince Hot Press that I was the best pick, and hope that the other pony hadn’t done the same.

“Come in!” Came the stern voice of the pony in the office, who I could only assume was Hot Press.

I pushed the heavy wooden door open and trotted in, giving a short wave to the unicorn with an outstretched hoof, “Good afternoon Mr. Hot Press, I’m Stardust, and I’m here for the design job!”

He gave a short, scrutinizing nod and gestured toward a plush seat in front of his desk, “Pleased to meet you. Why don’t you have a seat and tell me about why you’re the best pick for the Manehattan Times.”

I gleefully took a seat and pulled my saddlebag around, rummaging in it for a neatly pressed sheet of paper that I had prepared inside, “Well Mr. Hot Press, let me just start by showing you an organized resume of some of my best work,” I slid the paper over and straightened myself in the chair, “I’ve been a freelancer for the better part of five years now, and that is *exactly* the kind of pony that you need for this job.”

He pulled the paper forward and began to browse through some of my work, “Mhmm, and why’s that?”

“Well, I’ve been out there working in every graphics field you can think of. Advertising, design, marketing— all that! And let me tell you, I’ve got a fresh view on what ponies are into. I know the ind, the out, what’s fresh, what’s stale— you name it!” I excitedly pitched.

He nodded, “Right,” He looked down at the sheet, “So right here it says you were working mainly with logos and layouts, do you have any experience with layouts in a print context?”

“For ads I do!” I cheerfully replied, “You ever make your way out to Ponyville? You know the big advertisement for Barnyard Bargains right when you enter town?”

“Mhmm,” he nodded, “What about it?”

“I designed that,” I confidently smiled, “and a few others on the way into town as you pull up in the train.”

Hot Press pursued through my resume for a few long moments before looking up at me and frowning, “Mr. Stardust? I hate to cut it to you like this, but we’re going to look at our other candidate.”

My heart sank as I heard those soul crushing words. I had tried so hard to be as confident as I could be, had I overdone it?

“I… but…” was all I could muster in the way of a defense.

A sympathetic look flashed across his face, at least giving me some comfort that he wasn’t just some uncaring face, “I’m sorry. It’s not that your work isn’t any good, it’s just that we’re looking for a pony with a little more… professional experience in our specific field.”

I cursed my luck but didn’t make any further objections. I had already lost my chance, making a scene would only make it even worse for me. I didn’t need to be blacklisted from the entire industry after all…

I looked back up at the unicorn and nodded, “I appreciate your time Hot Press, thanks for considering me.”

I tried to sound as cheerful and optimistic as I could, but both of us knew that I was plainly lying through my smile.

“You’re very welcome Stardust, if we have any opportunities open in the future I urge you to re apply.”

I nodded, “Thanks, I’ll keep an eye out.”

As I slowly stood up and made for the door, my mind turned to my only other option at this point… the job agency.

Desperate Times Call for Desperate Measures... Really Desperate Measures

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Alright Stardust, there’s no need to panic. Sure, your last ditch effort of finding anything in your career field failed, but the job agency’s totally going to be able to set you up with something workable, I thought to myself. Sure it was probably overly optimistic, but hey, a job was a job and at least I wouldn’t have to go run off to some cave with some of the other bats.

Sure, they were good enough company, but a lot of the other bat ponies weren’t as business oriented as I was. They were into the more woodsy and artisanal careers. You know, stuff like hunting, fishing, logging— yes, believe it or not there were quite a few logger bats way up north by the crystal empire. All good careers, but stuff I wasn’t ever going to be able to fit in with. Well, not true, I could have totally made a fishing job work, but that meant basically running back to some far off lagoon or lake and cutting ties with civilization.

So those were all out, leaving me to seek out some professional help. I glanced up at the towering skyscrapers above me and then over toward the small hanging sign that sat above the entrance of one of the smaller buildings nearby.

“Helping Hooves Job Agency,” I read aloud, earning a confused glance from a passing pegasus.

This was definitely the place, but there was no telling what kind help they’d be able to offer. I had only heard a few things about them, and it was split right down the middle. Stuff like they could help any pony get any job, and alternatively that sometimes they had a tendency to misfile or even lose paperwork. I was desperate for a job though, so I was willing to take my chances. Like I said before, I had basically no experience outside my field, except for one janitor job I held for a few months back when I was starting out in Canterlot. It wasn’t a fancy job in the slightest, just a short stint bussing tables at some bat run restaurant in the caves under Canterlot, but at least it was something.

I could live with bussing tables in some cafe, heck, I’d even settle with some janitor job in one of the stuffy office buildings. I didn’t care what it was just as long as it kept the lights on. Taking a probably very unneeded deep breath, I pushed open the door and stepped in, my ears perking up at the bell chimes that rang out, alerting the pink earth pony that was sitting behind the desk.

He looked up at me and smiled, “Welcome to Helping Hooves, how can I help you today?”

“Well uhh,” I cleared my throat, “I’m finding myself in need of a job… and I was kind of hoping that you guys would be able to help.”

He nodded, “Well you came to the right place!” He waved me over to a cubicle in the corner of the room, “Office Job can help you out.”

I nodded and took a seat in front of the older looking pony, “Nice to meet you Mr. Job.”

“Oh just Office is fine,” he smiled, “So, you’re looking for a job eh?”

“Yep!” I cheerfully replied back, “I just got turned away from a bunch of interviews, and had a friend say you guys could get anyone a job.”

He chuckled, “Well we certainly try our best. So what kind of job are you looking for Mr…”

“Oh, Stardust. And to tell you the truth, I just need a job. Any. Job.”

“Mhmm,” he nodded, “and what kind of experience do you have?”

“Well, I’m a graphic designer… or I guess I was, and I bussed tables at the Knight’s Light down in the Canterlot Caverns a while back.”

“Anything else?” He inquired, turning toward the nearby filing cabinet and rummaging around.

“Yeah actually, I can make a pretty mean grilled cheese too.”

“Right…” he dug through the cabinet some more, muttering incomprehensibly to himself. Finally he pulled out two folders and laid them across his well worn wooden work desk.

I was a little worried that he only had two folders out of what seemed like a few dozen or so that were crammed into the cabinet. But these were the professionals. Clearly they didn’t need to grab out all of them, because they were the experts at finding a pony any relevant jobs, and clearly Office Job had narrowed it down to two.

“So, Office, I’m guessing you’ve found the best fitting jobs for me?”

He nodded, “At least based on what you told me about your job history.”

“Right… So what are we looking at, anything exciting?”

He shifted in his seat and glanced between myself and the folders for a few moments, giving me the sense that he was trying to figure out how to break some bad news to me. I braced for the inevitable yeah you’re unhireable but before I had a chance to panic, he spoke up.

“We have two jobs that might work for you.”

“Okay, two’s better than nothing. So what are they? Busser at a restaurant or janitor at the theater?”

He shook his head, “The two jobs we have right now are junior sanitation agent and a butler position at Orange Manor.”

“So janitor somewhere or fancy janitor in an old mansion is what I’m getting?”

“That’s… one way to put it,” he hesitated, “Although I don’t know how interested you’d be in the first one.”

“Oh? Why wouldn’t I be?” I asked as I tried to steal a glance at the job’s folder. It couldn’t be that bad right?

“Well, the junior sanitation agent position requires a fair bit of time spent doing maintenance in the sewers, and I can say that this is a job that rarely gets filled for long.”

I scrunched up my muzzle at the thought of that. He didn’t really give me the full detail, but I could piece together enough. Trotting through raw sewage in a narrow sewer duct— yeah no, I didn’t need to imagine that any further.

“I can guess why,” I looked over to the other folder on his desk, “What about that? The butler job?”

“Ah yes, the butler job. You’re looking at most likely a night shift doing basic tasks around the estate. Making sure the family’s needs are tended to, running errands, that sort of stuff. It’s tiring and boring work, but they pay well enough.”

I didn’t need to even think about this, my choices were trudging through sewage and probably never having a chance at getting that smell out of my coat, or tidying up some dusty old manor. I mean the choice was pretty obvious.

“Well, guess you can call me Graves.”

“You’re interested in the butler job I presume?”

I nodded, “It’s that or dealing with raw sewage and considering that makes me want to throw up just thinking about it, I’m gonna go with the other job.”

He jotted down a few notes and nodded, “I’ll have to send this into the head butler there for approval, but I’m sure they’ll be fine with it.”

“Perfect!” I cheered back, just relieved that I’d be able to make end’s meet, “So any idea when I’ll probably start?”

“You’ll probably be good to go in a few days,” he slid a form over toward me along with a fancy looking quill that must have been older than I was, “I just need you to fill out this form and we’ll be able to send it away.”

I peeked down at the simple paper, taking the quill in my hoof and filing in the basic information. I signed my name, wrote down my address, dropped in my prior job history, and just like that Office Job had trotted off to some back room to send it off. An anxious, but excited feeling welled up inside of me. This had been way easier to deal with than I thought it would be…

Almost too easy…

A Minor Mixup

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The next few days went by pretty uneventfully. I hung out in my apartment and relaxed, watched one of the cheaper plays (which was still pretty great mind you), took some nice late night strolls in the park, and really not much else. I could have celebrated getting a new job by going out to eat and spending a night on the town stopping by all the awesome hangouts and doing all of the stuff I wouldn’t have time to do anymore, but I was a frugal bat… well, that and I also didn’t really know how my new job would pan out. It wasn’t worth spending a bunch if I didn’t even know how the job would go.

For all I knew it could have been a crappy job that I’d wind up working for a few weeks before stumbling into something else. Taking all of this into account, I decided to hold off on celebrating until I had actually worked there for a little while— just long enough to see how everything would play out. Plus I didn’t really have a whole lot of friends here… really none at all come to think of it.

Don’t get me wrong though, I wasn’t completely alone. There were the few bats I passed on the street and had hung out with in the park a few times, but no one I’d consider a super close friend. Well, that is until I met her, but that comes later in the story, and I promise we’ll get to that sooner rather than later. The point we’re at now is where my story really took an interesting turn. Whether it was for better or for worse… well, I already know the answer, so I’ll let you put the pieces together.

I was sitting in my apartment watching the sunrise out of the small window in my room when I suddenly heard a knock at the door.

“Delivery for Stardust!” Came the courier’s voice, a kind sing songy sound that belonged to an equally kind pegasus that I had befriended.

Now I know I just said that I didn’t really have any friends out here, but that didn’t mean I didn’t have my own little hooffull of acquaintances. That’s besides the point though. A twinge of excitement filled me up like some kind of electric charge and I took off toward the door, excited to get the details on my brand new job.

I snuck a quick glance in the nearby mirror, making sure I looked presentable enough even if the mare was someone I’d consider a friend, and flipped on the lights, meeting her with an overexcited smile that I couldn’t hope to hide.

“Heya Moondrop! Off to a busy morning so far?”

She nodded, “Yep, lotsa packages and letters to sort through, but ya know, that’s what makes it fun.”

“Glad to hear!” I beamed, “Sometimes you just gotta keep upbeat about work like that.”

“I try my best,” she smiled, “Got a couple of special deliveries to you from Orange Manor, I didn’t realize you did any work for them,” she passed me a dark Orange clothes bag and an ornately decorated envelope that bore a seal stamped with a stylized orange.

I looked up at her and shook my head “I actually didn’t do any work for them, but I am going to work for them.”

“Oh? That sounds exciting. What kind of job is it?”

“Just a butler job over at the manor,” I responded, “Nothing fancy, but it’ll pay the bills and keep me in town at least.”

“Sounds boring, but shouldn’t be too hard, eh?”

I nodded, “Just tending to the family and doing their running around. Should be a breeze and at least it’s only the night shifts so it’s not like it’s going to be very eventful anyways.”

“That’s the spirit,” she cheered back, “Now I hate to just drop off your stuff and dash off, but that’s kinda my job, so we’ll have to chat later.”

“Sounds like a plan, see ya later Moondrop!” I smiled, “And tell Ray I said hi.”

“Will do, see you later Stardust.”

In a flash the mail mare was gone, leaving me alone with my odd package and exciting letter. Without any real hesitation, I tore open the bag and pulled out the contents within, stopping dead in my tracks as I turned the garment over in my hooves.

It was a maid’s dress…

A very frilly maid’s dress…

And I was a stallion… Something didn’t line up right here, and truth be told, I half thought this was some weird dream or prank.

Don’t get me wrong, it wasn’t out of the ordinary to see stallions pick up fashion trends and clothing styles that were traditionally reserved for mares, but I had never even considered getting something like this in my life, let alone wear it for work. I had to admit though, it was a cute design and the Orange family sure didn’t cheap out on it. I rubbed a hoof over the soft fabric, confused at why I had even gotten this instead of the expected butler uniform.

I scratched the side of my head with my other hoof and blinked my eyes a few times, as if that would just magically change the garments. Confirming that this wasn’t just some weird dream, I set the dress aside and reached for the envelope, checking the address and name to make sure it was actually addressed to me and not some clerical mixup. Maybe it was just some weird misunderstanding, or maybe they just sent the wrong uniform… I didn’t know, but I was determined to find out.

A quick glance at the fancy script written on the outside confirmed that it was definitely addressed to me, but none of this made any sense. I was a stallion that was hired for the butler job, not a maid job. But a maid’s dress had been sent to me from the manor, making the situation confusing to say the least.

I carefully pulled the letter out of the sealed envelope and turned it over in my hooves, making sure this wasn’t some weird trick.

“Salutations and congratulations Starshine!” I began to read aloud, already noting that they got my name wrong, “We would formally like to extend a welcoming hoof toward you as you begin your new job as one of the maid’s in the manor,” Yeah, no, this was definitely not right, “Please report to the maid’s quarters in full uniform at sunset tomorrow evening for your orientation. We look forward to having you, and have a pleasant day!”

I read through the letter probably a good three or four more times before shaking my head. Something was definitely mixed up, and I needed to get to the bottom of it before sunset tomorrow. I mean, I didn’t have to, but at the same time I kind of did. I needed this job, and I couldn’t afford to just walk away from it, especially if it was just some silly error. That’s what it had to be, right?

Okay Stardust, it’s just a clerical error. You just gotta go see Office Job and explain the mixup and he’ll get everything sorted out for you… I thought to myself, not sure if I believed myself or not…

As I looked out the window and squinted at the rising sun, my mind was made. I needed to go check in with the agency and get to the bottom of this, surely they’d be able to help sort it out. I mean… they’d have to right?...


Tricky Talks and Desperate Decisions

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I flew through the morning sky, dodging and weaving between the many tall buildings that peppered the skyline. While I would have normally opted for taking the scenic route, today was different. Today was more urgent. It wasn’t life or death urgent, but still urgent. It was the I need to sort this out before the end of the day kind of urgent, which never made for a fun day.

I could already feel a headache coming on, but now wasn’t the time for stress. No, that was only going to be an issue if things didn’t work out here. But they would, these ponies were professionals and I knew they’d get everything sorted out in no time, I just had to keep an open mind and trust that they knew what they were doing.

Catching sight of my target, I dropped out of the sky, coming to a graceful, (though probably frightening for any passerby) landing on the sidewalk out front. A small crowd of ponies jumped back in surprise, but I didn’t stop to apologize or listen to their complaints. I was on a mission.

I trotted into the agency’s lobby and glanced around, taking sight of Office Job in the far corner filing something away. Right off the bat I was approached by the receptionist from the other day, who seemed to pick up on my annoyed demeanor. Probably because of the expression on my face, which was a potent mixture of confusion, annoyance, and even a little curiosity.

Curiosity, weird right? But look at it from my point of view. I was desperate for a job and had started to make peace with the idea that I might just have to bite the bullet and deal with this clerical error for the time being. I didn’t personally want to go with that opinion, but my only other option was working in the sewers and I was not going to resort to that.

“Stardust, right?” He asked, bringing my attention back to the urgent issue at hoof, “Can I help you?”

I nodded, pointing toward Office Job with an outstretched hoof, “I need to talk with them about my job, there was some kind of mixup and I need to get that sorted out as soon as possible.”

He nodded, walking me over toward Office Job’s cubicle, “Alright, just hang out for a minute and I’ll go get this sorted out.”

“Thanks,” I smiled as they trotted away, leaving me alone with my thoughts for a few solitary moments.

I genuinely had no clue if Office Job was going to be able to help me or not, but I had to keep an open mind about the situation. These were professionals… even if they did get my papers all mixed up somewhere along the way. Granted, maybe I should have listened to the few warnings I had gotten, but there wasn’t much I could do now.

“Good morning Stardust, anything I can help you with?” The older stallion asked me, “I’ll take it you got your assignment in the mail?”

“Oh, believe me, I did,” I nodded, reaching for the letter, “That's what you can help me with.”

He arched his brow, “Is there an issue with the assignment?”

“You could say that,” I passed him the letter, giving him a few moments to read through it.

The stallion browsed through the ornately decorated paper and then flashed me an embarrassed look, “I can see why you might be dissatisfied with this…”

“Uh huh… dissatisfied... So, what can you do about it?”

Office Job sat in silence for a few long moments. as the gears turned in his head. He glanced back down to the letter and then up to me, “Do what about what?”

“The mixup!” I unintentionally shouted, “Did you read the letter? Starshine, working as a maid? Doesn’t that seem a little off?”

A look of realization flashed in his eyes as if he realized the severity of what he had done. He opened his mouth but quickly stopped, pausing as if he was trying to find the right words to ease my frustrations, “Your file was accidentally switched with Starshine’s…”

“Right,” I nodded, not wanting to make a bigger scene than I already had out front, “So… can you just, you know, switch them back?”

He shook his head, “I’m afraid I can’t. It’s already been finalized.”

I raised an eyebrow, “What do you mean? The letter said I still had until sunset.”

You still have until sunset, but Miss Starshine started her shift last night.”

“You mean my shift!” I let out a deep breath and calmed myself, “Okay, sorry to get loud, I just really need to make sure this gets fixed. Let’s start over, you said she started my shift last night. So what’s that got to do with anything?”

“The job earmarked for you has been… filled, I’m afraid.”

“Filled,” I flatly replied, “So uhh… can we just call her up and get this sorted out?”

The stallion flashed me an embarrassed look, “I… I’m afraid that isn’t doable. It appears your files were both mixed up, but she still started your job regardless, and we can’t just ask her to leave it.”

“But she’s not leaving it, we’d just be switching so we can both have the jobs we’ve signed up for.”

“I wish it was that easy Stardust, but once a candidate starts their shift it’s out of our hooves. You could go talk with the respective heads at Orange Manor, but outside of that there’s not really much that I can do here.”

I let out a small sigh, “So what you’re saying is that I’m out of a job then?”

“Not necessarily,” He glanced back at the letter, and then over to a file on his desk, “You could always take the sanitation job if you were interested… It’s not ideal, but it’s still open.”

I shook my head, my voice dropping into a desperate whimper, “Anything but that… please!”

He turned his attention back to the letter, “Well, you do still technically have an open opportunity in front of you.”

“What?” My eyes flashed open, “You mean the maid job?” I skeptically replied.

He shrugged, “It’s an option to consider… you said you bussed tables in a restaurant in the past, you wouldn’t be doing anything too terribly different during the night shift if you took that job… just… scaled up a bit.”

I paused, glancing between the letter, the file, and Office Job. Was I seriously going to consider this? I mean I had made peace with the idea on my flight over, but I didn’t actually think that I’d be doing it…

“I… I…” I let out a frustrated sigh, “Do I need to wear the dress if I take the job? Or can I at least keep some of my dignity?”

“If that’s what they sent you for a uniform then that’s what you’d need to wear to the orientation. You’re free to take it up with them once you’re there, but you’d be wearing it for at least a work day.”

I shook my head, letting out a bewildered laugh, “Right. Guess I can check that off my bucket list then.”

“Oh? So you’ll take the job then?”

I nodded, “I’ll take the job.”

The stallion perked up, “Splendid! Be sure to show up right on time, and make sure your uniform is in order. Those ponies are kind and understanding, but they can be sticklers for the rules and they’ll be expecting you to show up dressed accordingly.”

“In a frilly maid’s dress…” I muttered out.

“What was that?” His ears perked up.

“Nothing, I was just saying I can’t wait to start…”

Office Job smiled, “That’s the spirit, Stardust! I know it’s an unorthodox job with an even more unorthodox uniform, but just go into it with an open mind, you might find that you actually enjoy it.”

I nodded along to his sage advice, though I didn’t know how much of it would actually prove to be true. I needed the job though so I’d have to at least try and keep in good spirits.

I can do this, it’s just wearing some frilly dress and hoping you don’t die of embarrassment on the flight to work, once you’re there no pony can bother you or laugh at you or whatever, I tried to convince myself. As they said, fake it until you make it, and if I pretended like I’d enjoy it then maybe I actually would in time.

I knew one thing for certain though, I’d have to spend the rest of the day figuring out how to get dressed for work… and get used to wearing dresses in general…

Dressing for Success... I Hope...

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I stared at the clothing bag for what must have been a good hour before I finally decided to carefully open it. With less than careful precision, I dumped the contents out onto my kitchen counter and began to sort through them. There was the obvious dress, which I set aside for later, but also some other garments that I hadn’t noticed before. Nothing overly surprising if I’m going to be completely honest, and it’s not like I really should have been in the first place. It was just your standard fare accessories that you’d expect with an ensemble like this. A set of long pink and black socks and a couple of large pink bows were nestled in their own bag, and I carefully pulled those out and laid them out next to the dress.

I didn’t really know where to start, so I hovered my hoof near the socks and paused, trying to figure out the best way to go about getting them on. I had never really worn socks before, which is ironic considering that nowadays a comfy pair of socks are basically a part of my everyday getup. But at the time I had no idea how in equestria I'd manage to pull them up my legs. Having no real clue where to start, I shrugged and grabbed a sock in my mouth, pulling it over my front left hoof and dragging it up as best as I could. Surprisingly enough, the sock went up with ease, though I figured my front legs would be the easy part.

Taking one of the other socks, I did the same with my right hoof and then paused as I considered how I’d do this with my back legs. I lifted my back leg and flexed it for a second, and then dropped a sock on the ground, trying to pull it up as best as I could. You could probably picture this well enough in your mind, but I must have looked completely ridiculous to any onlooker, which thankfully there weren’t any. I fumbled around for more than a few minutes to no avail, only being able to pull the sock up part way. In my frustration I attempted to lean down and get a hold of the sock with my mouth, but all I managed to do was fall flat on my face with my back legs sticking up in the air.

I let out an annoyed sigh and rolled over, blowing a loose strand of my mane out of my vision. Suddenly an idea came to me while I stared up at my back legs. Maybe I was going at this with the wrong angle? I backed myself against the counter and leaned up, taking the top of the sock in my mouth and pulling it down as far as I could, using my other two hooves to bring it the rest of the way. This turned out to be an effective method, albeit a little unorthodox. With any luck though, I wouldn’t have to do this with any regularity. Repeating my unusual method, I pulled the last sock onto my other leg and in no time I was dressed… well, at least my legs were.

That left me with the bows and the dress… and I honestly had no idea where to go next. Deciding that the bows would be easier to put on without the dress, I opted for those next. A quick inspection of the ribbony accessories showed that my life was going to be a lot easier than I thought. Both bows seemed to be designed as one piece, that I’d only have to pull my mane and tail through. This did come with the realization that my mane would be pulled into a ponytail, and my tail would be pushed up more, but none of this really mattered in the long run. I was going to go out into the world in a dress and a few extra articles of clothing would do little to change how embarrassed I’d feel.

Lastly I turned to the dress, running a hoof over the soft, silky material and gave a confident head nod. I was going to probably look dumb and goofy, but who cared. Not wanting to delay the inevitable, I grabbed the silky garment in my hooves and pulled it up over my head, struggling to get my front legs into the proper holes. Thankfully this outfit was designed to go on with ease, and only needed a sash to be tied around the waist. That part itself was surprisingly easy to tackle, and no doubt it was designed that way.

I made a couple of quick adjustments to the dress and trotted over to the mirror, slowly opening my eyes to take in my new appearance. The pony that greeted me in the mirror was unmistakably me, but it was almost hard to recognize my reflection at the same time if that makes sense. I mean heck, there I was, staring at myself wearing a maid dress, socks, and bow in my mane. It was odd to say the least, but I had some time left in my day to adjust.

I couldn’t believe I was actually going to do this. I mean, well, I was doing it already, but I didn’t actually think I’d ever reach this point in my life. I nervously adjusted the pink and black socks that I had painstakingly put on, (I mean really, why do ponies even bother with these? Like it takes so much time to do, is it even worth it?) and slowly trotted around the room, trying to get used to the feeling of wearing a… of wearing a maid’s dress.

That’s something I never imagined myself saying— well, thinking. If there was a bright side to all of this though, at least the awkward outfit I was being asked to wear was comfy, and maybe even a little stylish? I glanced over to the mirror again, feeling strangely… kind of cute. Look, I know I said I wasn’t one of those ponies that just wore stuff like this around, but I was starting to see why others did. Not to say that there still wasn’t something inherently embarrassing about the thought of going outside dressed in a maid’s dress, but I could actually get used to the getup. Sure, it wasn’t my preferred attire, but it also wasn’t going to be the hassle that I thought it would be at first.

I took a deep breath, facing the door with the letter held under a wing, and my head held as high as it could be. Alright Stardust, one hoof in front of the other. You’re just a pony going to their job, and no pony else is going to bother you. Sure, you’re wearing a frilly maid’s dress, but you look cute in it and other ponies think you look cute in it too, I mentally pepped myself up and pushed open the door, not even giving myself a second to consider running back to the agency and trying to find some other job. But no, I didn’t have that chance.

This was going to be simple, and I’d hopefully only have to wear this attire for a day. No need to get cold hooves and run back with my tail between my legs over something silly like that. I stepped through the door and trotted out as cheerfully and confidently as I could.

I was ready for this! I was maid for this job!

The Awkward Walk and an Embarassing Talk

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What did I get myself into? I frantically thought as I anxiously trotted down the street.

I had been briskly making my way over to my new place of employment for the better part of I don’t even know how long. The embarrassment of wandering through a familiar city wearing some frilly dress made the minutes stretch into hours, and I was on edge. To make matters worse, I was clearly the only pony out that had any article of clothing on, and it made me stand out even more amongst the crowd. Just what I needed, even more anxiety and worry.

I trotted along fast as I could in the dress, barely even moving my eyes from their straightforward gaze out of fear that I’d make eye contact with someone I’d recognize. Much to my own relief that hadn’t happened yet, and I sure hoped to keep it that way. I was clearly making a mountain out of a molehill, but could you blame me? The anxiety and excitement of this unorthodox outing did little to calm my nerves, and in fact it only really seemed to heighten my senses. To my dumb, panicky mind everyone was staring at me and silently judging me, even if the reality was that no one gave any second thought to a stallion wandering through town in a maid dress. That didn’t stop my mind from racing to the worst conclusions however.

I was quickly lost in thought and as I continued along the rest of the world slowly faded into the background. I was on autopilot now, which was a dangerous path to trot down, but I didn’t consider this until I collided with a passing mare, knocking the both of us down and striking any chance at not drawing any more attention to myself.

“Hey! Watch where you’re going!” the blue bat pony shouted. I let out a nervous squeak and she flashed an almost embarrassed, sympathetic look of her own, “Oh I’m sorry miss, guess I got a little jumpy.” She helped me up, earning a nervous eep!

“I’m uhh… not a mare.”

Her eyes widened, “Oh my gosh, I’m sorry. Guess I saw the dress and just jumped to conclusions,” she glanced over me and laid a comforting hoof on my side, “but is everything okay? You’re not hurt, right”

I shook my head, “Everything seems okay. What about you?”

“Good,” she helped straighten my dress and paused, “Name’s Sheila, I don’t think we’ve met before.”

“S—Stardust!” I squeaked out, earning a confused glance from her.

“Stardust eh? Well it’s nice to meet you. You in a rush for something?”

“I uhh— I gotta get to work. It’s my first day.”

“Right, well I’ll let you get to that Stardust,” she replied back, almost disappointedly.

“Wanna meet up after work sometime? Maybe in a few days?” I blurted out.

She scrutinized me again before flashing a small smile, “Diamond Diner in two days, sunrise?”

“I… I’ll be there!” I replied.

“See you soon Stardust!” She cheered back as she started to trot off.

What are you doing?! I thought to myself. She’s gonna recognize you now. You just bumped into a cute mare while wearing a maid dress and you’re going to go have breakfast in a couple of days! Good going genius!

I shook my head and picked up the pace, now wasn’t the time to sit and mentally berate myself over this. I had two days to make up some explanation, I didn’t need to stress over that now. I turned my gaze forward and hastily continued toward my destination, glad that at least no one had actually recognized me yet.

“Heya Stardust, that you?!” Came a cheerful voice of my mail mare friend.

My face turned a deep red and I silently cursed the universe for its dramatic irony as she landed next to me, clearly trying to hold back a giggle.

“Moondrop!.. it’s uhh, nice to see you. Got a busy day with the mail?”

“Earlier I did,” she paused, seeming to hang on the verge of asking something, “So… what’s with the dress? I never pegged you as the fashion forward type.”

“Dress? What dress!” I nervously blurted out. What dress? Why did I always have to jump to the flimsiest excuse imaginable?

“The one you’re wearing, silly!” She teased, bopping me on the muzzle.

“Ohh, that dress,” I nervously laughed, “Well uhh… funny story. Remember that package you delivered earlier?”

“The rush package from Orange Manor? What about it?”

“Well uhh— you see, that was my work uniform. I’m uhhh their new maid.”

“Huh, well that’s good for you. Not the uniform I’d expect them to give you, but it’s cute and you totally rock it.”

My eyes shot open in surprise, “I’m sorry, what was that?”

“You totally rock the dress. Not a lot of stallions can pull it off like you can. Think this is gonna be a regular look for you or just an occasional thing?”

My face flashed an even darker shade of red, “I… I don’t know. I didn’t think about this.”

“Well definitely think about it, it’s a cute look!”

I almost didn’t know what to think aside from being embarrassed over this, and maybe even a little flattered. Weird, right? But in a really odd turn of events, Moondrop complimenting me on my look almost made me feel more at ease. The mare from before hadn’t poked fun at me, and the one pony that recognized me on the street had said I looked cute in the outfit.

I returned a confident smile and raised my head up, “You really think so?”

She smiled, “Oh no, I know so.

I couldn’t help but let out a small laugh, earning one from her in return.

“You don’t know how much that helps to hear. I’ve been trotting along feeling so nervous about what other ponies would think, guess I psyched myself up.”

“Don’t worry about what other ponies think. Worry about what you think.”

As nervous as I was, she had a good point. What did it matter what other ponies thought? Maybe I thought this was a weird getup, but clearly I was making it a much bigger issue in my head.

“You know what, you’re right Moondrop. I was so worried about this, but it’s really not an issue at all.”

“See? Just roll with it and see what happens. As long as you’re comfortable and happy that’s all that matters.”

I smiled, “Thanks again. This means a lot more to me than you probably know.”

“No sweat, now I don’t want to just spoil a good mood, but I gotta get back to my mail route. You have a great day though, keep me updated on how the whole job goes, I know you’re gonna do just fine there.”

“Thanks, I’ll let you know how it all goes for sure.”

“Cya later Stardust!”

“Goodbye Moondrop.”

Just as soon as she had shown up, she was gone leaving me alone, but feeling far more confident than I had felt before.

I continued on my walk, but this time something was different. Instead of being anxious and embarrassed, I carried myself way more confidently than I had before. As Orange Manor came into view, I couldn’t help but feel confident that everything would work out just fine.

I just knew that things would turn out fine!.. right?

Maid For The Job

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I slowly, but confidently trotted up to the gate and gave the bell a ring, waiting for a few moments as an attendant trotted up. The sun was low in the sky, but not quite at sunset yet, but I figured being early was far better than being late, and if I wanted to sort everything out then that would be my best option. First impressions really made a huge difference between whether you’d be able to swing someone or not, and I really needed to put my best hoof forward.

“Greetings, how may I help you?” They asked, cutting through my thoughts.

I greeted them with the warmest, most confident smile that I could muster, which really wasn’t all that hard anymore, “Good afternoon, I’m here to start my orientation as one of the maids.”

“Oh you’re our new hire. Splendid,” he opened the ancient looking iron gate and waved me in, “Starshine, right?”

I shook my head, “Stardust. It’s a long story though, there was a mixup with some paperwork but I’m here to start the job. Just need to talk with the head maid and get everything sorted out.”

The attendant seemed to eye me with a confused mix of surprise and indifference, which dug into me a little bit. For a moment I felt as if I said something wrong and was about to be escorted off property, (which probably would have made me look like some kind of lunatic mind you), but soon enough his face softened and that chipper smile returned.

“Right this way. Satin Ribbon will be able to assist you with anything you might need.”

He began to lead me along a fancy cobblestone path, taking me alongside the manor’s lush gardens and meticulously manicured lawn. A smaller, though just as ornate looking building sat a short distance away, and I could only assume that this was the servant’s quarters. Did the rest of the staff live here? I wondered to myself.

As if he had read my mind, he chimed up, “This is the servant’s quarters and main area for all of the manor staff. Some of our staff live on property, but from what I understand, you have your own lodging?”

I nodded, “Yeah, just an apartment like 20 minutes away.”

“Wonderful. Now of course, there will be a room assigned to you, you’re free to use it at your discretion, but you won’t be expected to live on property.”

“So I get my own room even though I have my own place?”

“Yes. Some of the shifts here run late, and it’s exhausting work at times. If you find you need a place to rest your head before or after work you’re free to do so. It also gives you a place to change and rinse off after a hard day’s work if you so desire.”

I nodded along, unsure of what to make of this so far, “That’s a pretty good deal. So what kind of shifts am I looking at?”

“Head maid Satin will be able to answer that for you.”

I nodded as he led me through the ornately carved wooden door and into a cozy looking foyer. He turned to me and held up a hoof, “Go ahead and wait right here, I’ll go call for the head maid and she’ll explain the rest to you.”

“Thank you Mr…”

“Stone Wall.”

“Thanks,” I smiled.

He nodded his head and trotted through one of the nearby doors, leaving me alone to inspect the place. I probably should have just stayed put, but I couldn’t help but wander around the foyer, scrutinizing the details of my new workplace. The whole place looked like it was straight out of some Hearth’s Warming card, and every inch of the place was textured with artisanal detailing that was definitely not cheap.

You wouldn’t guess it from my designs or the way I decorated my apartment, but I was in love with the way this place looked, and a part of me was more than overjoyed that I was going to be working here for the foreseeable future.

“Mr. Stardust?”

I perked up and turned away from the large grandfather clock I was looking at and caught sight of a dark red pegasus with her bright blue mane tied up in a large flowing satin ribbon.

“Satin Ribbon?” I questioned, though it was pretty obvious to me.

“Nice to meet you. So you’re our new maid eh?”

“I uhhh… well, you could say that. I’m gonna wager a bet and say you were expecting a mare named Starshine to show up?”

She nodded, “Yep. And obviously you aren’t her, so I’m going to wager my own bet and say that this is another case of mixed up paperwork from the job agency?”

“How could you guess?” I teased, “So does this happen a lot or something?”

Satin Ribbon let out a cheerful laugh, “If I had a bit for every mixup they’ve caused I’d have my own manor. So that leaves you in an awkward position, but I hope we’ll be able to come to some kind of compromise that’ll work for you.”

This all seemed great so far. Satin was very cheerful and welcoming, and the way she carried herself in the conversation made it feel less like a work related conversation, and more like a personal one.

“I was hoping you’d say that,” I paused, “So what do you have in mind?”

“Well that depends on what you want to do. The maid position is still open if you’re interested, and you did take the time to show up in full uniform, but what do you actually want to do?”

“Well, I guess first thing’s first, is there any chance I could just switch to the butler job? That’s what I originally signed on for and if it’s possible I’d like to go do that.”

She nodded her head slowly but began to frown, giving me a sense of worry. Why would she be frowning if there wasn’t bad news coming?

“I see… well… I don’t know how to break this to you in a way that doesn’t just kill your spirit, but that position’s been filled, and the pony that filled it isn’t interested in switching over to the maid position.”

“Right… So, I guess I really only have two options here then.”

“Which are?” She asked with a raised brow.

“Well, I can either stick with the maid job or go find work somewhere else. Considering that I know what the other option is, and I really don’t want to go for it,” I took a deep breath, “I’ll stick with the maid job.”

Satin’s eyes opened wide and I couldn’t tell whether her expression read I can’t believe he’s actually doing this or He doesn’t know what he’s getting himself into. But I didn’t really have another choice.

“That’s… unexpected, but perfectly alright!” She cheered back, “I’d love to have you onboard, and if you want I can show you the ropes and get you started on your very first shift!”

A small smile slowly spread across my face, “I’d love that… but just one more thing…”

“Oh? What’s up?”

“Is there any chance I could get a different uniform?” I gestured down to the dress I was wearing.

She paused for a moment and flashed me another sympathetic glance, “I’m sorry, but there aren’t any others available. Is that going to be an issue at all?”

I felt my heart drop a little, but seeing as how I didn’t really have any other options, I shook my head, “No… no, it won’t be.”

The smile returned to her face, and she cheerfully waved me toward the door she had come out of, “Super! Now if you just want to follow me I can go show you the ropes!”

I nervously adjusted my dress and began to follow her, excited to start my job, but unsure of what the future held in store.

Everything would work out in the end, right?

Settling In For the Long Haul

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So there I was, a maid in training in Orange Manor, unsure of where my future would lead. What I did know was that I had a job that would at least stay steady, even if the uniform I had to wear was more than a little embarrassing. Still though, it was a paycheck, and I could put up with the hit to my dignity… plus, I totally rocked the outfit, which I had to admit, was definitely comfy and cute. As cute as it looked the dress was still a massive hassle to put on, so as much as it was embarrassing to do, I found myself wearing it more than I ever thought I would have to.

This wasn’t as bad as I thought it would be though, turns out that when you wear cute outfits around town you tend to pick up more attention and compliments than you normally might. Needless to say, what I thought would wind up being incredibly embarrassing and mortifying wound up giving me an unintentional confidence boost. Sure, it wasn’t always the attention I wanted to get, but being told you rocked an outfit and looked cute really did wonders for your own self image.

So what was the training itself like? Simple mundane boring stuff mainly, though I got plenty of odd looks and laughs from the mares I worked with on that first day. By the second they had all mellowed out, and it was business as usual, or rather, I guessed it was business as usual. I still didn’t really know what my day to day life here would entail, but that’s what I was here to learn. And that’s what I was doing tonight with Satin Ribbon, my new boss who was proving to be a surprisingly kind and casual pony. Not that I expected her to be harsh or anything, but she was the head maid in a prestigious manor, so the fact that she was so… friendly… stood out to be— in a very good way.

“So Star, what brought you here anyways?” Satin Ribbon asked me as we gathered up the dinnerware from the now empty dining room, “I know you applied as a butler and not a maid, but the question still stands.”

I smiled, “It’s a long story, but basically I’m a graphic designer that’s stuck doing freelance work whenever I can, which doesn’t really pay the bills,” I lifted a few plates off the counter and into the cart we had pulled along, “Didn’t have much luck finding work in an actual place, which basically meant I had to either find anything or go move elsewhere, and I didn’t want to have to do that… again.”

“So you chose maid— I mean, butler service? Why not something… you were more qualified for?”

I shrugged, “Well, my option there was basically go work in the sewers or go run errands for a bunch of rich ponies at night… which you know, I figured was the far better alternative.”

Her face scrunched into a frown as she sorted through the utensils, “Yeah… I can see why you chose this place.”

“Uh huh, and why I stayed with it.”

“I didn’t realize that that was your alternative, and I can really see why,” She waved me over to the end of the table, “Alright, you grab one end, I’ll grab the other, and we’ll pull this over and fold it up. We bring the dishes to the kitchen for cleaning, and then bring the linen to the laundry room next door for washing.”

I nodded, “And we have to do both?”

She shook her head, “No, that’s somepony else’s job. You might eventually cycle into that position, but for now we’re the ones that tidy up rooms and get them into a presentable shape. You’ll also dress the tables before every meal, though in your case that’s just for breakfast at the end of your shift.”

I nodded, pulling my end of the table cloth over to the edge of the table, “And then I can either head back home or go spend time in my quarters?”

She nodded, “It’s your choice. You won’t be allowed to roam the manor itself, but if you’re feeling tired or just don’t want to fly all the way back to your apartment then you’re free to go rest your head in your room. It’s nothing fancy, but it’ll give you a place to rest after work.”

“Now you said this was all taken out of my salary. Say that I don't want to use that, is that something I can opt out of, or no?”

“Whether you use it or not is up to you, but it’s included in your employment. Sleep in it, take your breaks there, hang out after work, whatever you want, as long as you keep it tidy and don’t trash it.”

“Do you live in yours? Or do you have your own place elsewhere? I don’t know if that’s weird to ask or not, just curious.”

“It’s not as weird as you’d think. A lot of the new hires ask that, believe me, you’re far from the first,” She finished folding the table cloth and began to push the cart toward the door, waving me along, “To answer your question, I’ve got my own place about five blocks away. I still stay there, but if I’m pulling a late shift or just feeling lazy I go hang in my room here. It’s pretty much like my private study, and there’s a few others that do the same.”

“Guess that makes a lot of sense actually. So any dos and don'ts I need to know about it?”

“Uh huh,” She trotted over to the kitchen and began to unload the cart, “Do use it as a place to relax in, do not use it as a place to hide from work in. Trust me, it seems pretty straightforward, but we’ve had some maids in the past that thought they could just go hang out there whenever they wanted to while on the clock. It’s on property, but as long as you’re on the clock and not on break, I don’t want to see you spending time in the servants quarters.”

“What if I have a friend I want to bring over? Or a special somepony? How does that work?”

“In that case you go check them in with that nice gatekeeper you met yesterday. He’ll add them to the list of ponies allowed in the servants quarters and staff common areas, but you’ll be responsible for anything they do here.”

“Meaning that if they break something, I buy it?”

“Mhmm,” She cheerfully nodded as we unloaded the rest of the dishes, “If they wander into the manor itself, or step away from the staff grounds then it’ll reflect back on you. So just keep that in mind. Also make sure they won’t distract you from your work, we’ve had that happen on more than one occasion too.”

I nodded as we moved into the adjacent laundry room, “Gotcha, keep whoever I bring over in line and make sure they don’t do anything bad otherwise I’m one hundred percent responsible for them.”

“Uh huh, you got it,” She opened up one of the large washing machines, “Now this part’s a little tricky, you have to find the right machine for the type of linen you have. This one here is what we wash all the table cloths and other dressings in.”

“I thought we weren’t in charge of this?”

She shook her head, “We’re not in charge of drying, pressing, or folding the laundry, but we do start the machines,” She pointed to a row of machines, “Those are for other things, like clothing, uniforms, napkins from the table… you get the idea. Each machine’s all set up for the specific linen and all we have to do is load them and press start, the other staff will take over from there.”

I helped lift the small bundle of linen we had taken from the dining room into the machine and paused, waiting for her instruction.

“Alright, now see that big green button?”

“Uh huh,” I replied, looking at the button in question.

“Go ahead and give it a press, and then follow me. We’re going to go grab clean linen and dress the table for breakfast. They won’t be dining for another hour, but it takes some time to get everything set up, and once we’re done with that then you’ll be done for the night.”

“Sounds great,” I paused, “So one last question, am I going to be doing this on my own eventually, or do you pair maids up for their shifts?”

She grabbed the required clean linen and smiled, “Good question. You’ll be working with another maid once you’re all trained and I’m confident that you’ve got a good grasp of your duties. I don’t think that’s going to take long at all with you, and if you’re ready to move on I can show you how we set the table.”

I smiled, “That sounds great, thanks Satin.”

So far, so good. This was only my second day on the job and I was already falling into a good routine, and seemed to be doing better than I ever could have imagined doing in this job. Truth be told, I wasn’t keen on this job before, but it was starting to grow on me, and I knew that I had made the right decision in the long run.

The only thought left in my mind was how I was going to explain all of this to my new friend on our not date in the morning…

Awkward Explanations

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I nervously shuffled my hooves as I sat at one of the cozy tables on the patio out front. Work had run a lot later than expected, and by the time I clocked out I had no time at all to change out of my uniform. So there I was, sitting in public waiting to go meet some mare I had bumped into the other day and my anxiety was back in full swing. They always said that first impressions meant everything, and my first impression so far was running into her, knocking her over, and then awkwardly explaining that I was a stallion dressed in mare’s clothing for my work before hastily agreeing to meet up with her again, and then running off full speed ahead in the opposite direction.

Yeah Stardust, you’ve totally got this, I tried to convince myself. Needless to say, I didn’t have this, as much as I tried convincing myself that I did. I mean I didn’t have to do this if I didn’t want to, I could have just disappeared and avoided this part of town for the rest of my life, or just try and hide my face. I mean what were the odds of randomly running into the same pony twice in a city as big as Manehattan?.. Small… but with my luck I probably would have ran right into her the next day, which would have made matters even more awkward. No, I needed to stop being dumb and just deal with this like a stallion… even if I was dressed like a mare right now.

So I shook my head, swallowed my pride, and put on the most confident face that I could. She wasn’t going to just freak out and treat me like I was some weirdo, she didn’t even seem phased by my outfit at our first meeting… so I just had to take that as a sign that everything was going to be fine, even if that little voice in the back of my mind was freaking out left and right and telling me that it in fact, was not going to be fine.

“Miss, are you ready to order or do you need a few more minutes?”

I looked up at the waitress and shook my head, “I’m just waiting for somepony, but I’ll take a couple glasses of water and an order of hay fries if you don’t mind.”

Her eyes shot open as she heard my distinctly stallion sounding voice, “Oh my gosh, sorry sir, I—”

“ — Thought I was a mare and you’re profusely sorry, it’s fine, don’t worry about it, easy mistake” I smiled, “I’ve gotten that quite a bit the last few days. Nothing to worry about.”

She breathed a sigh of relief and nodded, “I’ll be right back with that in just a few minutes.”

“Thanks,” I smiled.

As the waitress trotted away, I caught sight of her, making me momentarily panic again. I didn’t have a chance to run off though, I was committed whether I liked it or not. She said something to the host, but I couldn’t tell what it was, only that it ended with a smile from him and a cheerful point to my table, where she made eye contact with me.

With a smile, she trotted up to my table and took the open seat, laying her saddle bags down next to her, “So, Stardust right?”

I nodded, trying my best to look cool and confident, “That’s me, and you’re Sheila?”

She nodded, “Yep.”

“Glad to see you again…” I didn’t know where to go, and I was already starting to feel like this was a bad idea.

“Me too… So…” She awkwardly started, giving me reason to start internally panicking.

“So.” I replied back, feeling my anxiety crush me again, “Have a busy morning?”

“Not really,” She shrugged, “Got some errands done and did a little running around, you know, the usual. How about you?”

“Just a lot of work, you know, the usual,” I let out a small, nervous laugh, “I gotta tell you though, I’m glad I just get to relax now.”

“I bet, you do cleaning stuff, right? That’s gotta be exhausting after a long day… or, I guess night in your case.”

“Mhmm,” I confirmed, “Over at Orange Manor.”

“Orange Manor, that’s that old house in the historic district, right?”

I nodded, “Yeah, probably the oldest building there.”

“I always thought that place was kinda interesting.”

I began to perk up a bit, feeling a little more confident and a lot less anxious. It was all going well so far, and I silently prayed that things would stay this way, “Oh believe me, it is. I’m a history nut and that place is like right out of Victorian Equestria. Probably one of the best examples of remaining architecture from that era, and it’s amazing how well preserved the inside is too!”

“Oh? Is it still stuck in the past? I went on a tour there back when I was a filly and it seemed so… old I guess? Like it hadn’t been touched in ages.”

I shook my head, “No… well, yes… kinda? It’s got all the old decor but they modernized everything else. It’s like the best of both worlds.”

“Huh, that’s actually kind of cool,” She smiled, “So what brought you there?”

“Excuse me, I’m sorry for interrupting,” the waitress from earlier interrupted, sliding a glass of water over to both of us, and an order of hay fries to me, “Now, do you already know what you’d like? Or do you need some more time to browse the menu?”

My not date shook her head, “I’ll take the fresh fruit platter with extra strawberries please” she turned to me, “How about you Starry?”

I glanced down at the menu and then back over to the two, “I’ll do that too, that sounds pretty good.”

“Oh believe me, it is,” she commented, “Diamond Diner has some of the best fruit in all of Manehattan,”

“I know right? I’ve only tried their hay burgers and fries, but you just can’t beat them.”

“That’s the secret, it’s the hole in the wall places that are the best. None of that fancy schmancy overpriced luxury bistro stuff.”

I smirked, “Oh man, you don’t need to tell me that twice. I thought I’d treat myself to a dinner at the Golden Horseshoe after starting my job and let me say, way overpriced and way under portioned.”

“Oh you poor devil, you actually ate there?” She gave me a playfully sympathetic look.

“First and last time, I’ll tell you.”

The waitress returned with our fruit plates carefully balanced on a tray on her back and slid them over to us with expert precision, “Order’s up, you two enjoy.”

“Thanks!” I cheerfully replied back.

“No problem, just give me a holler if you need anything else.”

“Will do, thanks,” Sheila replied, taking a few bites of the fresh fruit, “So Starry, how did you get into that job in the first place?”

I paused mid taste and almost dropped one of the strawberries right then and there as a wave of embarrassment flushed over me again. I let out a small cough and cleared my throat, making sure that I hadn’t spilled anything on my dress. These things were a pain to clean, and I was not going to deal with that today. I looked my companion in the eyes as I fiddled with the plate of hay fries that sat in front of me, being careful that my pristine socks weren’t messed up by the food.

Not wanting to delay the inevitable, I took a deep breath and began my unneeded explanation. “So… let’s just cut right to the chase, you’re wondering why I’m wearing a maid’s dress when I’m clearly a stallion… I can see that bewildered questioning look in your eyes, and believe me, I was in your horseshoes at one point too…”

It’s kind of a funny story though!