• Published 25th Oct 2020
  • 756 Views, 82 Comments

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

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

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

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.

Author's Note:

So I was trying to come up with ideas for outfits to draw my OC in a while ago, and someone said "Draw him in a maid outfit!" So to that I said "Sure... but only if my passion project gets regular comments"... and it wound up finally getting that many months after the fact. (Or at least it started to.)

So keeping to my word, I made a pointy pony of my OC in a maid's dress, and it all went downhill from there, leading to a few friends in another server suggesting I turn the picture into a story, and well, here we are. I hope you all enjoyed this random one shot, and I'm sure I'll have plenty of other stories and chapter updates on the way soon!