The Filly Fatale Folly

by DatZigga

Rating: mature
Tags: Fetish, Comedy, Filthy Rich, Sex, Spoiled Rich, Profanity, Diamond Tiara, Slice of Life, Human, Romance, Silver Spoon, Anon, My Little Pony: Friendship is Magic
Length: 3666

Diamond Tiara and Silver Spoon develop a schoolyard crush on the local human.

With the School of Friendship newly minted, Spoiled Rich asks resident human, Anonymous, to tutor her precious princess. However, The Rich Family seem to have ulterior motives in mind...

Mature tag is mainly for mature themes and to allow more creative freedom.

Published 2020-08-22 07:10:00 UTC
Last updated 2020-11-07 00:00:23 UTC

Prologue: Everything’s Coming Up Schoolhouse

“So what?” Anon asked, sizing up the dragon with a skeptical gaze. “You fly now?” Spike, that pudgy little dragon that Anon owes a lot for his newfound pony social life, hovers enthusiastically at Anon’s eye level. It was a strange feeling, not having to crouch down to interact with the drake. But he was sure it did wonders for his knees.

“Yup. I finally molted and now I’m rocking these bad boys.” Spike looked back at his wings dreamily, capturing himself under their charm. Anon snickered.

“You know, I thought they’d be bigger.” Anon teased. Spike reflexively grabbed on to his wings, coddling them to his chest like a baby.

“Hey! I’m still growing!” Spike shot back, before plummeting to the ground. He landed on his bottom with a thud. Anon chuckled deviously to himself. When he finally ceased before Spike could light his pant leg on fire again, he looked up at the massive school building that stood before them. It was massive and ornate, being built of crystal and having its own most surrounding the perimeter. It even had a scenic waterfall for some ungodly reason.

“I still don’t get why a ‘School of Friendship’ has to be this well funded.” Anon remarked absentmindedly. “I mean, you’re just teaching people basic social etiquette right? Shouldn’t this stuff be basic knowledge?”

“Well, it only makes sense.” Spike replied. “For thousands of years, all the kingdoms of Equestria have remained isolated from each other. By bringing in students from across the kingdoms and having them learning the Magic of Friendship, we guarantee a harmonious future built by these very students who can bring back the lessons of friendship to their homes!”

“Yeah, but is such a future really going to be achieved by telling a bunch of teenagers sharing is caring?” Anon raised an eyebrow, doubling down on his skepticism. Spike looked up at Anon, perplexed.

“Why wouldn’t it?” Spike asked.

“I’m just speaking from experience.” Anon answer. “Although, I guess humans just make things more complicated than they ought to be.”

“You sure did when you got here.” Spike answered back with a sly smile. “I always did say that Twilight and her friends would help you and you refused. Now look at you!”

Anon turned and glared at the dragon.

“You know, I bet I could pluck those little bastards right off your-“ Anon interrupted by the sight of gaudy carriage being pulled down the road by an elderly stallion. It looked like one of the royal carriages that would be occasionally found in Canterlot in the few times Anon visited. Yet, something about the wagon seemed off. It looked kinda like the ones collecting dust at Sweet Apple Acres, only spruced up to appear more elegant and ornate than it was.

“Oh boy...” Spike muttered, flying next to Anon to get a better look at the carriage. “That’s Filthy Rich’s carriage.”

“Who? Diamond Tiara’s dad?” Anon asked, vaguely remembering his time with Diamond Tiara.

“The one and only.” Spike seemed unimpressed with the carriage. “Although, it’s usually not Filthy Rich that rides them. It’s his wife.”

“Yeah, heard they were going through some rough patches.” Anon looked to Spike for confirmation, but was met with a shrug.

“That kinda stuff is usually Rarity’s wheelhouse.”

Anon raised an eyebrow. “Don’t act like you don’t eavesdrop.”

The carriage drew closer to the two, eventually stopping right next to them. The elderly stallion, who looked more like a butler now that he was closer, gave the human a curt nod in greeting. Anon nodded back cautiously. He was rather shocked that he was the apparent destination and prepared himself for the worst.

He watched as the window of this carriage slowly descended. Inside was indeed a pink mare wearing shades, which only made the human noticed the oddly sharp schnoz. Hell, it looked like a rhinoceros horn. Anon silently noted that it probably helped keeping the shades in place, never mind the fact there was no reason to wear shades inside a carriage unless you were that far up your ass. He further noticed that while the mare looked to be still, he could see by her shoulder that she was in fact turning a crank that lowered the window.

“Would you that, Spike?” Anon joked aloud. “She got the windows that you can roll down. Now, that’s a sign of high society!” He had hoped Spike would have at least chuckled, but the dragon instead looked away, attempting to not be part of the interaction.

“So,” the mare started, pulling her shades down to look at the human. Her cerulean eyes scanned the human, as if she were inspecting him. Anon merely rolled his own. “You’re the alien prowling around town?”

“Shit, I hope I am.” Anon replied. “If there were another one, I’d feel a little less special. What brings you out of your ivory tower?” Spike nudged him in a futile attempt to curb Anon’s usual assholery.

“I was lead to believe that you are friends with the Element Bearers, correct?” The mare removed her glasses entirely. Anon always thought he was the only one in this land of rainbows and magic to be cursed with resting bitch face, but to his surprise, the mare almost had him beat. Her eyes were hard and judgmental, her muzzle a permanent sneer. “You’ve also interacted with my daughter as well, right?”

“Yes to both. Is there a problem?”

“Oh, far from it!” The mare answered with a smile. Yet, the smile did little to convey anything positive. “Actually, it’s quite the opposite. You see, I have certain aspirations for my darling daughter. She is a smart and resourceful filly, just like her mother. However, at her current school, I find that her curriculum has been a little...lacking. Furthermore, I’m worried that the students and teacher there are becoming a bad influence on her. I-“

“You want me to convince Princess-I mean, Principal Sparkle, to enroll your daughter into the School of Friendship.” Anon crossed his arms, cutting to the chase.

“You catch on fast.” The mare sounded impressed. “But that’s not exactly it. See, I know that Principal Sparkle would not allow me to simply buy our daughter a seat in her school. Believe me, I tried.” Anon and Spike rolled their eyes in unison. “So, I was hoping that a gentle-stallion like yourself would instead become a tutor for my daughter.”

“A tutor?” Anon asked. “What’s being her tutor going to do for you?”

“Well, you see, the School of Friendship has a placement test.” The mare rests an arm on the carriage door. “The test covers a whole myriad of pointless subjects, all in the hopes of determining a students willingness to learn and their capacity for learning. I want to ensure that my little Tiara passes that test.”

“And you assume that I know how to prepare her for that?”

“You were a student of Celestia, were you not?” The mare smirked as Anon rubbed his neck.

“I mean, technically.”

“Then that’s good enough for me.”

Spike decided now was the time to cut the conversation short. “Sorry, Ms. Spoiled. But my friend here has no interest in letting someone as mean and rude as Diamond Tiara enter the School of-“

“What’s in it for me?” Anon asked bluntly. Spike’s jaw nearly dropped to the floor, which is impressive given how he flies now.

“The Rich Estate will pay you for your time, of course. 30 bits an hour sounds like enough.”

“Bump it to 50.” Anon smiled devilishly. “I have a life beyond the pony world, so this would be rather inconvenient to my own studies. Besides, as a student of Celestia, you can expect quality lessons that were earned from real experience.” Spike rubbed his eyes to make sure he wasn’t hallucinating. The mare, on the other hand, grinned happily.

“Fine. 50 it is. Come by the Estate tomorrow at noon.” The mare places the shades back over her eyes and leaned into her seat. “I’d give you directions but you’ll know it when you see it.” Wordlessly, the butler begins to pull the carriage once more, carting off the mare down the road. When the wagon was out of earshot, Spike spoke up.

“Are you serious?!” Spike shouted, his wings flapping furiously. “You’re gonna help Spoiled Rich, the rudest, most cutthroat mare in Ponyville!?”

“Hell no!” Anon answered, feigning offense. “The broad has massive Karen energy! Plus, I hate rich people.”

“So then why are you taking a tutoring job for Diamond Tiara of all ponies?”

“Why not Diamond Tiara of all ponies?” Anon turned the question back on the dragon. “She’s not the brat that she was before anymore, right? The CMC got her to be a little nicer, right?”

“Emphasis on a little.” Spike held his claws millimeters apart for emphasis. “She’s still the daughter of the Rich family, and the Rich family aren’t known for their politeness.”

“Neither was I.” Anon retorted. “Spike, it was you that said that by teaching the youth the magic of friendship, they can guarantee a more harmonious future. And what better way to secure that future then with a philanthropist? If Diamond Tiara passes the placement test and gets in the School of Friendship, think about all the things the wealth that the Rich Family hoard can be used for. Urban redevelopment, job creation, outreach centers, you name it, they could buy it.”

“You’re doing that thing again.” Spike noted.

“Doing what?”

“Overcomplicating things.”

“I’m not overcomplicating things!” Anon shouted defensively. “I’m planning ahead! You think that the world will be a better place just because people will be nicer to each other?”

“Yes.” Spike answered bluntly. “Yes I do.”

“Exactly~!” Anon booped Spike on the nose, causing the dragon to reflexively cover it. “And what better way to achieve that goal than a happy, rich filly empowered by the magic of friendship?”

“Okay, okay. You got a point.” Spike relented as he rubbed his nose. “But, why you?”

“What’s that suppose to mean?” Anon asked seriously.

“Anonymous, let’s be real.” Spike said, clasping his claws together. “You’re not exactly teacher material. You’re abrasive, vulgar, and you hardly practice what you preach.”

“Are you saying that I’m not a good role model?” Anon placed his hands on his hips.

“That’s exactly what I’m saying.” Spike answered, mimicking Anon’s gesture. Anon scoffed, throwing his hands in the air.

“Unbelievable.” Anon shook his head. “My own dragon-from-anotha-wagon doesn’t believe in my ability to inspire the youth. Truly, friendship is dead.”

“I just think that you should maybe go about this a little differently?” Spike pleaded. Anon remained quiet for a moment, before suddenly laughing.

“Oh, my little drake.” Anon patted Spike on the head, much to his displeasure. “There is another reason I’m doing this.”

“I’m afraid to ask.” Spike admitted before swatting away Anon’s condescending pets. “But why else are you tutoring for the Rich family.”

Anon holds up his hand. “Five words: Cash Rules Everything Around Me.”

Chapter 1: Meet The Riches

“It is an honor to finally meet you in person, Mr. Anonymous.” Filthy Rich greeted the human, raising a hoof to be shaken.

Anon took note of the well kept mane and the professional tie. It was a smart move then for Anon to have visited Rarity a day prior to this meeting. He got fitted for a full suit, just in case. You never know with rich people. Besides, it was a nice looking tuxedo with a red tie. Putting it on, it almost felt familiar. Like it was an extension of himself or at least of his legacy. Still, the suit was about the only good thing he was feeling.

The honor is mutually exclusive. Anon thought internally, as he faked a smile and shook the stallion’s hand. “It’s a pleasure to meet you as well. I must admit, you got quite the home out here.”

“Indeed I do.” Filthy Rich smiled, a sense of pride filling his chest. “It was my family that helped founded Ponyville after all. We created the wonderful, vibrant community that has welcomed you with open arms.”

“Weren’t the Apple Family also present?” Anon asked.

“Yes.” Filthy answered. “They helped too. Now, if you will follow me, I’ll show around the mansion. It’s quite easy to get lost, you know.”

“Oh ho ho, I bet.” Anon’s words dripped like venom. Despite knowing very little about the stallion, Anon couldn’t help but feel the upmost contempt for the horse. Filthy seemed out of place to him. An upper class implies a lower class, which in turn implies a lower standard of living. If the average pony lives life carefree, how good do these fuckers have it? Before Anon could revel in any Marxist fantasies, he found himself in the first location is the tour: the kitchen. The kitchen was enormous, easily able to fit a staff of at least 10 ponies. However, the only one doing any cooking was the butler from earlier.

“Yo, who’s that guy?” Anon asked, pointing at the butler.

“That would be Randolph, our most esteemed butler!” Mr. Rich introduced. The butler didn’t so much as acknowledge either of their presence. “He’s been with my family since the very beginning. He’s as much of a Rich as any of us.”

“Man’s got hustle, I’ll give him that.”

“This is our kitchen! We modeled it after the royal kitchen in Canterlot.” Filthy Rich bragged. “Granted, we don’t necessarily have the staff to occupy and make proper use of it, but is quite a beauty to look at, is it not?”

“No.” Anon answered flatly. He looked back at Filthy Rich, only just remembering his faux manners. “Oh, I mean, yes. Of course. Very pretty.”

“Ooookay.” Filthy Rich segued, a little awkwardly. “Well then, allow me to show you the guest bathroom. It has a sauna.” Filthy left through the kitchen doors, leaving his host behind.

“Of course it does...” Anon muttered under his breath, before following.

And so they went from bathroom, to guest bedroom, to other guest bedroom, laundry room, private swimming pool, game room, other game room, and other pointless rooms that one family did not need. Finally, the tour concluded with Diamond Tiara’s room. Behind its closed door, the sounds of two fillies at play. Before Mr. Rich could open the door however, Mrs. Rich exited from the only bedroom they haven’t visited, likely the parent’s bedroom. When she sees the human, a sly smile peeks from under her pointed muzzle.

“Well well, if it isn’t Mr. Anonymous.” She greets, trotting towards the two men. Actually, it was more of a saunter, as if she were making her way across a red carpet and not the hallway of a mansion. They may as well be the same anyway.

“Ah, I see you are already acquainted with the missus.” Mr. Rich takes Mrs. Rich’s hoof in his own and gently plants a kiss. “This is Spoiled Rich, my beloved wife.”

“Oh, that’s actually your name...” Anon mumbled. “I thought Spike was being a dick...” He quickly cleared his throat before the parents asked for him to speak up. “A pleasure to meet you again, Mrs. Rich.”

“Oh, trust me. The pleasure is all mine~!” Mrs. Rich cooed in a...friendly way. Anon shook her hoof slowly, nodding his head.

Well. That’s foreboding. Anon thought to himself, carefully withdrawing his hand. “Hey, so how about we meet the little princess, shall we?”

“Of course!” Mr. Rich agreed, none the wiser to the man’s internal plea. He gave the door a cursory knock before immediately opening it. “My little princess! Daddy found a tutor for you!”

“Hey, Ms. Tiara how gooooooo-“ Anon greeted with the wave of his hand before using said hand to shield his eyes and turn his head. “-oooh shit.” Anon was promptly reminded once again that he was a modest, human alien in a horse world where modesty is a fashion statement.

With their backs turned to the parents and new tutor, Diamond Tiara and Silver Spoon laid on the bed reading a single, large textbook. Whatever the textbook contained could not be studied by the parents nor tutor as Diamond Tiara and Silver Spoon collectively pushed the book off the other side of the bed. They turned back with guilty faces.

“U-Uh, Hi M-Mr. and M-Mrs. Rich!” Silver Spoon stuttered unconvincingly.

“Daddy!” Diamond whined, jumping to her hooves to face her dad. “I thought we agreed you weren’t going to barge into my room anymore!”

“But, sweetie, I knocked before entering.” Mr. Rich answered, genuinely confused.

“If I may, Mr. Rich.” Anon lowered his hand to address the stallion. “Usually you knock and then wait for a response before entering.”

“Yeah! Exactly!” Diamond was quick to agree. Silver Spoon stealthily slipped off of the bed and started trotting quickly towards the door.

“It was fun, Diamond but, uh, I gotta go. Enjoy getting tutored.” She spoke quickly before squeezing past the parents and human. Once she was passed, she full sprinted down the hall, the stairs, and out the door.

“What in Celestia’s going on here?” Mr. Rich inquired to a bullet sweating Tiara.

Now, Anon was many things. An asshole? Yes. Socially inept? You betcha. Depraved? Depressingly so. However, the one thing he isn’t, a trait not shared by Mr. Rich, is oblivious. Whatever Diamond Tiara was doing is something that need not be explained to the parents. So, he acted quickly.

“Ah, I see what’s going on here.” Anon spoke up, holding a curled finger to his chin.

“You do?” Mr. Rich looked up at him.

“Of course!” Anon walked over and took a seat on the bed with the flustered filly. “You see, Ms. Tiara here caught wise to your plan to send her to the School of Friendship. So, she arranged a group study session with Silver Spoon, to get a head start. But they didn’t want you to know because they wanted to impress us all at the first possible chance. Isn’t that right, Ms. Tiara?”

Anon looked down at the filly, giving her a knowing wink. She stared back, dumbfounded, before regaining her senses to corroborate the story.

“H-He’s right!” She spoke up, putting on her acting chops. She looked moodily at the ground, drawing little circles on the ground with her hoof. “I just wanted to show you all that I’m a hard worker. I didn’t mean to cause a scene.”

“Are you kidding, sweetie?” Mr. Rich trotted over to Diamond Tiara, squishing her cheeks. “I’m so very happy to hear that my little princess is taking her studies so seriously!”

“Daddy!” Diamond whined again, her lips puckered together.

He looks over to the human, fist pumping in success. “And you, Mr. Anonymous. My darling wife was right about you! You are perfect for the job. I mean, such a way with kids.”

“Yeah, I’m a child at heart.” Anon rubbed the back of his head, selling the sheepishness Mr. Rich was looking for.

“Well, I’ll leave you to the tutoring then.” Mr. Rich backed off, adjusting his tie. “I have a meeting with the Apple family that I have to attend to and the misses will be in attending me, right honey?”

“Oh, but of course dear.” She said in a sweet tone as she rolled her eyes. Mr. Rich takes his wife hoof and leads the two out of the room. Before she closes the door, she looks back at the human with a lecherous gaze. “Perfect for the job indeed...” With that she closes the door, leaving him alone with a Diamond Tiara who collapsed on the bed.

I’m sensing a few red flags. Anon admitted. An oblivious husband, an unfaithful wife, and a child that is discovering herself is not the ideal household in which to take a job of any kind. But cash rules everything around me, so...

“Thanks for bailing me out, Anon.” Diamond Tiara mumbled into the bedding, still embarrassed for having been caught unawares. Anon reached over and patted her on the head.

“We all go through it, sometime or another.” Anon offered as comfort. However, curiosity lingered in his mind. Just what was Diamond Tiara and Silver Spoon reading? While Diamond collected herself, face engulfed in a finely embroidered blanket, Anon circled the bed to the book laying on the floor. He crouched down to pick it up. Almost instantly, Diamond Tiara shot up, acutely aware of what he was doing.

“Wait!” Diamond crowd out helplessly.

“It’s just an anatomy book?” Anon asked incredulously, looking at the cover. He thumbed through the pages, which at best had pictures of anatomical models that were more scientific than risqué. “Come on, I figure you ponies can do better than that-“ He nearly choked on his word.

Cleverly hidden deep within the pages of the textbook were pages of what could only be described as the pony version of Playboy. Playpony? Anyway, the pages were torn from their original publication and glued to the pages of the textbook. On this particular page, a blue stallion stared back at him with the same lecherous gaze given to him by Mrs. Rich before.

Anon inhaled through his nose. He held for four seconds as he closed the book. He exhaled through his mouth. Diamond Tiara laid speechless, unknowingly holding her breath. Anon turned towards her with a cheerful smile and closed eyes.

“I never read this textbook.” Anon stated simply.

“You...never read that textbook?” Diamond Tiara repeated slowly, confused. Anon violently threw the book to the adjacent wall with only the pivot of his hands, otherwise remaining perfectly still. The book landed behind a drawer. The sudden activity of motion startled the filly.

“What textbook?” Anon asked innocently. “I saw nothing.”

“You...saw nothing.” Diamond Tiara nodded, understanding the unspoken.

This is gonna be a long semester.