So this is me just posting an update, discussing this idea further and seeing if anyone has any fun feedback to offer. Thus here is what I have so far.

The story follows an earth pony mare named Sherry, who had this misfortune of being named by a mother who loves to drink. Due to a combination of her name and her decent appearance, Sherry is often treated rather poorly by the unicorn stallions in Canterlot. However, one day Sherry's fortune changes when one evening she is saved by a noble stallion named Dark Moon (he's actually from the show). Much to her surprise this rich unicorn didn't want her to repay him with her... assets, but to instead come work for him as a maid in his mansion.

Seeing that Dark Moon is actually interested in helping her and not in using her, Sherry starts to develop romantic feelings for her new master, however, there's two problems:

1. When it comes to romance, Dark Moon is as dense as a block of concrete.
2. Sherry isn't the only mare that is romantically interested in Dark Moon.

As it would turn out, Sherry isn't Dark Moon's only maid. As it turns out there are three others and they aren't too thrilled that another mare is on the battlefield. To make matters worse, these three mare's aren't completely normal either as they all have some sort of monstrous trait that they can manifest when they desire (something that Sherry is seemingly lacking).

While Sherry and the other three mares start off as rivals, after a terrible incident in the manor, it soon becomes clear that they four of them must start working together and try to get along, otherwise their employment at Dark Moon's mansion will come to an end. As the story goes on Sherry learns more about her fellow maids and gradually the four of them become good friend.

Of course, it isn't all just cleaning inside the mansion, with Dark Moon being a researcher of magical artifacts (or interdimensional magic, I haven't decided), sometimes strange monsters appear and run rampant around the mansion and our beloved maids must work together to defeat them.

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Now with the premise out of the way, let's get to the discussion.

As you can probably see, I haven't established much for the other three maids aside from the fact that they have monstrous traits. That's mostly because I'm still working on these characters, however I can mention my ideas for what they will be.

• A mare with a mane/tail that can turn into tentacles.
• A mare that is actually a werecat/neko.
• A mare with horns kind of like an oni.

As for the monsters, I felt that it would be fun if it wasn't just the maids that were monsters.

Now I'm still trying to figure out what kind of work/research Dark Moon does that could warrant these strange creatures occasionally showing up in the manor? One thought is that he would research magical artifacts and sometimes these artifacts are holding a monster or are perhaps a magical creature themselves. Then again, there's also the of having a Dark Moon study magical portals/interdimensional anomalies and that could explain the monsters' presence.

Of course, if you have a suggestion for the type of career Dark Moon might have that would warrant that, I'm all ears. Constructive feedback is always welcome.

Another question to ask is this, if you have a monstrous maid who can create tentacles and a monster is unleashed inside the mansion that is a swirling mass of tentacles, is that too much tentacles?

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Of course, if you have a suggestion for the type of career Dark Moon might have that would warrant that, I'm all ears.

Hats. He cleans the hats of wizards and magicians and occassionally pulls out some weird object or a monster out of there.

Seriously though, I think going with a dorky magical researchers that works at everything and nothing at the same time should work well and also complement his somewhat dense personality. It’s not like all the non-maid monsters have to come from just portals or magical objects.

Another question to ask is this, if you have a monstrous maid who can create tentacles and a monster is unleashed inside the mansion that is a swirling mass of tentacles, is that too much tentacles?

Sounds like a great opportunity for a tentacle wrestling match.

Also, you can never have too much tentacles!

The premise sounds great, by the way.

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The premise sounds great, by the way.

Thank you.

Seriously though, I think going with a dorky magical researchers that works at everything and nothing at the same time should work well and also complement his somewhat dense personality.

Well, that is kind of what I had in mind. I just wasn't too sure how well people would like that. "One day he was studying a Sombulian artifact, the next teleportation magic." I thought people might think that was a bit too goofy. That's why I had suggested him being a researcher/collector of magical artifacts. One thought I did have was that Dark Moon is part of a "secret society," which is revealed just to be a group with of ponies who like studying magic, sharing secrets and pretending to be part of a secret society.

Might include a few other characters in the "society" (if I went along with it), including Comet Tail and perhaps even Twilight Sparkle.

It’s not like all the non-maid monsters have to come from just portals or magical objects.

I suppose. The question is, what other ways are there? Now that I think about it, there could always be a Pokemon reference in there. A wild tentacle monster appears.

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"One day he was studying a Sombulian artifact, the next teleportation magic." I thought people might think that was a bit too goofy.

That's actually how most reserchers, naturalists, and anyone else worked... and some work this way up to this day as well.

One thought I did have was that Dark Moon is part of a "secret society," which is revealed just to be a group with of ponies who like studying magic, sharing secrets and pretending to be part of a secret society.

I'm honestly not sure if this would really contribute to the story, as it seems like you'd need to make it into a larger part of the story for this kind of humour to work properly.

The question is, what other ways are there?

Well, they might be drawn to his house from elsewhere due to the sheer concentration of magic there, for example.

"Hey, boss, another monster appeared in the manor."

"Damn, I knew I should have put the magic dampener on that cursed ring before it summoned something."

"No, sir, the monster walked in through the front door."

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I'm honestly not sure if this would really contribute to the story, as it seems like you'd need to make it into a larger part of the story for this kind of humour to work properly.

More than likely it is something that would be jokingly hinted at (made out to be some sort of big deal) only for there to be a society meeting unveiled in one chapter.

Well, they might be drawn to his house from elsewhere due to the sheer concentration of magic there, for example.

"Hey, boss, another monster appeared in the manor."

"Damn, I knew I should have put the magic dampener on that cursed ring before it summoned something."

"No, sir, the monster walked in through the front door."

That's funny. I like it.