• Published 25th Oct 2020
  • 587 Views, 80 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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Dressing for Success... I Hope...

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!

Author's Note:

We’re nearing the end of our journey, but expect at least two more chapters (an ending plus an epilogue.)

This was a blast to write, and I’ve got some ideas for other jobs that Stardust might wind up picking up eventually.


Here’s the obligatory “Please go check out my passion project, any thoughts or feedback in the comments section would be super appreciated and would definitely motivate me to write more!” section too. (Consider it maybe?)

EDo Ponies on Earth have Magic Dreams?
The story of an optimistic young night pony, the special pony that enters his life, and how the two of them follow their dreams to make the world a better place!
Tiki Bat · 193k words  ·  65  10 · 1.1k views