Anon x DT - not me, by anon

>You are Anonymous
>And, well, you've made some questionable decisions lately
>For being someone dropped into a magical, alien land of colorful talking horsies, you'd like to think you've adjusted pretty well
>You made a few friends, got yourself a job, and you're even making a decent amount of money
>So, when Filthy Rich, your boss, asked you for a favor, you agreed
>After all, since luck has treated you so kindly so far, you feel like the least you can do is to try to give a few good deeds back in return
>Pay it forward, if you will
>So, one Friday afternoon, just as you're cleaning your desk off, Filthy Rich knocks on your office door
>"Evening, Anon. I see you're done early."
"Yeah, pretty much. Got the spreadsheets finished. Looks like sales are improving."
>Filthy nods, his slicked mane eerily still despite the motions of his head
>"That's great, Anon, really great. In fact, I think I might see a raise in your future."
>Fuck yeah
>"But that's not what I'm here to talk about. I need a favor, if you don't mind."
>Mentioning a possible raise right before he asks for a favor?
>Clever pony
"Sure, what's up?"
>"Well, I'm taking my wife to see Hinny of the Hills, up in Canterlot. We're going to be staying the night and, well... I don't really have a babysitter for our daughter."
"Oh. Listen, Mr. Rich, I'm really not that great with kids, to be honest, and..."
>He shakes his head
>"Ah, nonsense. She's a perfectly-behaved filly. Won't give you any trouble at all, I promise."
"I dunno... I mean, I'll do it if you need me, but--"
>"Excellent! Knew I could count on you!"
>Filthy claps you on the back, his strength impressive despite his small size
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 Anonymous  11/08/15(Sun)17:31:34 No.25380954▶>>25381134 >>25381218
>>25380825 #
>So, you decided to go along with it
>And that was your fist mistake
>After all, you thought, how hard could watching a tiny pony be?
>And besides, you could *really* use that raise
>You're getting enough money to stay afloat right now, but a little extra could get you a nice new place, or some... well, something more than your usual drab affair
>So, yeah, you take the job

>Filthy agrees to meet you at his home at seven sharp, giving you three hours to prepare
>On the way home, you stop and pick up some snacks: marshmallows, some soda, chips... anything you think a kid would want
>After all, what kid doesn't love candy?
>Back at home, you take a nice long bath, making sure to properly groom yourself afterward, apply a little cologne, and all that good shit
>You don't dress too fancy though, after all, it's just babysitting
>Or whatever the pony equivalent is
>Horsie-sitting?
>You show up at Filthy Rich's place ten minutes early, where a pink, snobbish mare answers the door
>"Oh. You must be the sitter..."
>Her voice seems to drip with disapproval as she examines you
>"Well... I suppose you'll do. Come inside."
>She leads you into the place, which is even larger and more opulent than you'd expected
>Hundreds of breakable-looking art pieces line the walls, and a huge spiral staircase leads from the foyer up into the higher levels of the house, as well as downward into a darkened, slightly-ominous space
>It's not often that anything in horsie-world makes you feel small, but this mansion is doing a pretty good job
>"Now, Mr... what was your name again?"
"Anon."
>"Mr. Anonymous. My little Diamond is a delicate, precious, sensitive little filly. I sincerely hope you're not too dumb to understand what your job tonight entails."
"Watch movies until she falls asleep?"
>Filthy's wife casts a disapproving look at you
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 Viral  11/08/15(Sun)17:43:36 No.25381134▶
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>>25380954 #
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 Anonymous  11/08/15(Sun)17:48:44 No.25381218▶>>25381503
>>25380954 #
>"Heavens no! You are to entertain her, do you understand? You are to keep her mentally engaged, enriched, and nurtured throughout the entire night! You are to make sure she enjoys herself, but not too much. You are here to make sure she stays healthy and safe until tomorrow afternoon. Anything else, and it'll be a nightmare finding work in this town again!"
>The pink mare puts her nose up, strutting deeper into the house
>Jesus, she needs to clam down
>You're just watching her kid for a day, it's not THAT big a deal
>Speaking of the kid, you still have yet to meet her
>Why would anyone need a house so big that it takes you ten minutes just to find anyone?
>The pink mare leads you through a long side hallway down to a pair of double doors, where she raps with three, short knocks
>"Diamond! The sitter's here!"
>No voice answers her, but you hear the pitter-patter of little hooves cross the room on the other side, followed by one of the doors swinging open
>A pink filly pokes her head out, her purple-and-white mane a poofy mess
>"I know, mother! I heard you talk--"
>Then she catches sight of you, and immediately ducks back into her room
>"Diamond Tiara! I wasn't finished speaking to you yet! Get out here this moment."
>"G-give me a minute!"
>You hear the sounds of frantic scrambling coming from behind the doors, and when they open again, the little filly -- Diamond -- has her mane arranged in a neat braid, which drapes prettily across her withers
>You think you even notice hastily-applied makeup under her eyes
>Kid's eager to impress, you guess
>Diamond's mother grabs her and forcibly scoots her out of the room
>"Come on, now, be polite! Introduce yourself!"
>The filly straightens up, trying to look you in the eye, but failing
>"M-my name is Diamond Tiara!"
>Her mother shakes her head, ashamed
>"That was terrible! Don't you remember what I told you? Try again!"
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 Anonymous  11/08/15(Sun)18:11:36 No.25381503▶>>25382651 >>25388119
>>25381218 #
>Diamond's little mouth twists into a grimace, and she forces herself to look you in the eye
>"Hello! My name is Diamond Tiara! How are you!?"
>"Hmph. Better."
>The filly exhales, sweating
"Hey, Diamond."
>You kneel down, thought that still leave you a head taller than her
"My name's Anonymous."
>You set the bags of snacks down and reach out a hand for her to shake
>Tentatively, she reaches out and places a tiny pink hoof in your palm, which you shake
>"Nice to meet you."
>She tries to do the same snooty turn-your-nose-up move that her mother does, but it doesn't work quite as well
>Speaking of her mother, the mare herself turns tail and begins to head back down toward the foyer
>"I've left extensive instructions with my daughter, Anonymous. She has a rigorous activity schedule tonight, and I expect you to follow it!"
>Diamond Tiara grumbles, plodding along grouchily next to you, staring at the ground
>Rigorous activity schedule?
>Jesus...
>You thought you were just babysitting, not being the kid's goddamn personal trainer
>She leaves the two of you in the foyer, taking her husband's hoof as he leads her out of the mansion
>"Take care, you two! If you need anything, talk to the neighbors! Ciao!"
>And with that, you're alone with the little pink filly
>Diamond continues to stare at the ground, sulking