A Rich Punishment

by TheCloppyComedian

Rating: mature
Tags: Sex, Diamond Tiara, My Little Pony: Friendship is Magic, Porn, Fetish, Spoiled Rich, Profanity, Non-consensual
Length: 4124

Diamond Tiara executes a plan to create a kinder, more considerate version of her mother. Of course, this plan involves sex and humiliation, but it's still good...right?

After witnessing her mother's unjustifiable, merciless firing of her favorite butler, the reformed Diamond Tiara decides that it's time her mother learned everything she had about being nice and kind. She will do this by ANY MEANS NECESSARY. There's no harm in helping somepony learn to be kinder...right?

Kinks: Foalcon, filly on mare, punishment, BDSM, straps, chains, whips, and one VERY dominant filly

This was a story suggested by superfun. If you like it, hit 'em up, and let 'em know!

Enjoy, everypony!

Published 2020-05-08 00:00:02 UTC
Last updated 2020-05-14 13:34:35 UTC

An Unfair Firing

Author's Note

NOTE: There is no clop here in the first chapter. That all takes place in the next installment. Gotta set it all up first! :)

An Unfair Firing

Diamond Tiara waltzed into her home, having finished her final day of school for the year. Ever since the Cutie Mark Crusaders showed her to the truth of who she was and how she was meant to behave, she had a new lease on life. No longer was she the secretly depressed schoolyard bully. She had learned how to love friendship and had also learned the traits of benevolence, kindness, and faith in herself and her fellow pony. She could not stop smiling that entire day as she had made much merriment at Ms. Cheerilee’s pizza party to end the year. She and her friends were ecstatic that the year was drawing to a close, and they could finally enjoy the warmth and beauty that summer offered. They even planned to kick off the season with a wonderful slumber party in the Crusader clubhouse.

“Mother, I’m home!” Diamond called as she trotted up the grand staircase of their Ponyville mansion, “I’m gonna get my things and head over to the Crusaders’ party!”

“Not in a million years!” Spoiled Rich replied. The snobby mare popped out of a side room and gracefully ascended the stairs until she stood on the same level as her daughter. She took a look at her offspring and pointedly turned her nose up. She couldn’t believe that her daughter, one of the elite of Equestria, wanted to befriend and socialize with ponies that were so far beneath their social class. She hated all that the Crusaders had done to Diamond, as she felt that her unique little filly was becoming drab and common.

“Diamond Tiara, you know how I feel regarding your incessant trotting about with those Crusader ponies.”

“But, Mother-“

“Don’t talk back to me, young filly!” Spoiled snapped, “you need to remember your place, my dear. You’re rich. They’re not. You’re special. They’re not.”

Diamond felt sick to her stomach. The Crusaders had introduced her to such wonderful things, and all her mother did was contradict them in her usual haughty manner. Her disposition seemed to be even more impertinent than usual that evening, and the red curtains draped behind her did nothing to soothe Diamond’s view of her. The young pink pony was on the verge of tears, as her mind fought with itself over what her mother said and what the Crusaders said. She knew that her friends were in the right, but her mother’s stern look nearly forced her mind to revert to its old, devilish ways.

“Ma’am,” said a kind voice. Spoiled and Diamond turned to see their head butler, Dumb Waiter, standing at the bottom of the stairs. Despite his name, he was far from inane or mentally moribund. In fact, he had helped Diamond on many a homework assignment and project. He worked for the Rich family to help offset the cost of living as a young bachelor, and Diamond had always secretly found him attractive. She batted her eyes a bit as he ascended the stairs to speak with them.

“What is it now, you putrid piece of rat droppings?!” Spoiled thundered, “I don’t have all night!” It was well known that she hated her wait staff and paid them next to nothing. But, all the same, Dumb Waiter still held his smile. Diamond admired him, along with all of the other members of their staff. She had learned to respect them and see them as ponies rather than stepping stones to her own satisfaction. She smiled up at him, trying to silently point out that she would be on his side no matter what.

“Well, ma’am,” Dumb said respectfully, “I had looked into my accounts earlier, and…well…the last check was only 10 bits instead of the usual 20. I don’t wish to be a bother, but-“

“It’s too late for that!” Spoiled barked.

“Yes, well…I was just wondering why you subtracted 10 bits from my pay?”

Spoiled looked like she was about to go the way of an old freight train and explode. Diamond swore she saw steam pour out of her mother’s ears, and her eyes were set ablaze. Spoiled’s selfish, nasty attitude was famous throughout the land, but this was a level that Diamond had never seen before. As the little filly watched in horror, Spoiled slowly advanced on the quivering butler.

“You…dare…to ask me…a question like that?” She asked with venom in every word.

“I…I’m so sorry, ma’am. I mean, it’s fine by me, but I’ve also spoken with several other members of the staff, and they’ve reported the same situation. Have…we done something to offend you?”

“You offend me every single time you draw breath, you alligator-skinned, pompous, sick son of a Hydra!” Spoiled Rich thundered. “In fact, every time any of you are in my presence, you offend me! You’re BENEATH me! So…let’s put it this way. Either you become happy with the new arrangement of 10 bits, or you go crawl through the sewers while you look for another job!”

Diamond gasped. She knew her mother was legendarily mean, but her cruelty had taken a turn for the worse. The queasiness crept up again, and she had to dash up the next flight of stairs and take refuge around a pillar. She just could not bear to watch her favorite butler get evicted, both from his job and from his friends around the house. As she listened, Dumb Waiter begged Spoiled to reconsider, and even offered up a compromise of fifteen bits instead of twenty. But Spoiled would not be brought to reason, and she mercilessly fired him. Diamond sat in her dark shadow and wept bitterly at the loss, for she counted on Dumb Waiter in many aspects of her young life.

Oh, Mother… she thought, …how could you be so unjust and uncaring? Poor Dumb Waiter doesn’t have any other source of income! How the hell can you even THINK of firing him?! Worse…you unfairly took 10 bits away from him! You STOLE from him!

Diamond felt her anger rise, only this was a new kind of rage. She had never been angry with her mother before, because she was too afraid of her. But now she realized that it was time for her to stand up to Spoiled Rich’s tyranny. It was time for her mother to learn how to respect the ponies around her, not just those who had as much money or fanciful possessions as her. Diamond grit her teeth together as a plan began formulating in her head. Yes…her mother would learn how to be nicer, whether she liked it or not!

The Punishment Begins

After heading to Rarity’s boutique to let Sweetie Belle know that she wouldn’t be a part of the sleepover that night, Diamond put her plan into action. She hated to disappoint her new friends like this, but creating an unforgettable night of pain and submission for her mother had become her number one priority. She would make it unenjoyable for the victim, but would reserve a great deal of pleasure for herself. She knew how to cause her mother pain, and she would do it until Spoiled agreed to be a little more flexible with everypony around her.

“Oh, Mother,” she called sweetly right before her bedtime, “may I ask you something?”

“Make it snappy,” her mother said coldly.

“Well, I was wondering if you might come to my room with me? For what I need to ask you, complete and utter privacy is required.”

“Oh, fine,” Spoiled snapped, “let’s go, then. I don’t have all night.”

So the pair made their way up the grand staircase and hung the right hand (or, hoof) turn down the magnificently decorated hallway. It was lavish, as anypony who lived in the luxury of the Rich family would expect. Suits of armor stood at attention all the way up and down the corridor, and door after door led into rooms filled to the brim with expensive objects and old family antiques. They did not spend their money on television sets or the latest in the electronic world, because Spoiled Rich did not believe in those things. She referred to them as frivolities, yet would go on shopping sprees costing thousands of bits.

She’s such a fucking hypocrite, Diamond thought as they trotted along.

When they reached her door, she grandly stepped aside and allowed her mother to enter first. She knew that Spoiled had reign of the house, and anypony who did not let her in before them was swiftly punished. She wanted to be the one administering judgment that evening, and she could not acquire a penalty for herself just as she was about to start. So, she bided her time, waiting for just the right moment to strike. Like an innocent little dove, she went and sat on her bed and waited for her mother to come to her. Little did Spoiled Rich know that, inside this particular filly, lay a cobra, coiled and venomous.

“Alright, my little Diamond,” Spoiled said somewhat sarcastically, “what is it?”

“Well, Mother,” Diamond said in a purposefully bratty way, “I have come to hate the Crusaders again.”

“Splendid, splendid!” The matron said, “but…only a few hours ago, you were bound and determined to attend their little slumbering soiree this evening. What changed?”

“Well, I realized that, even though they got their cutie marks, I STILL got mine WAY before them! That makes me even more special than they are, right?”

“Oh, yes, darling! Yes, it does!”

“Good, so…I was wondering if you might give me some ideas on how to make them feel like rats.”

Spoiled sneered. These were the opportunities that she loved to take advantage of. Bullying ponies who did not have as much as she did, or had made her family look like fools, was a pastime that she took very seriously. She hated all the ponies who she felt were “beneath” her. Heck, she even hated a lot of her fellow rich ponies! The matronly scoundrel carried a lot of animosity in her black little heart, and she would unleash it all upon her daughter. By the next afternoon, the Crusaders would be small, blubbering piles of fur, and Spoiled wished that she might witness it.

“Alright, my dear,” she said wickedly, “I can give you a LOT of tips…”

“Come closer,” Diamond said with a fake sneer crossing her face, “I wanna hear it in full detail.”

“Of course,” Spoiled said as she leaned in.

Then, all of a sudden, Diamond struck. She pounced on her mother and quickly grabbed some rope she had hidden under the covers. She tied her mother to all four bedposts, forcing her back legs open and revealing the gems in between them. She then forced Spoiled’s head back against the headboard and slinked up her chest, leaving small bites along the way. Her mother yelped in pain as her daughter’s teeth made their mark. Just like darts nailing their bullseyes, Diamond’s pearly white incisors created deep red areas on her mother’s fur.

“Oh, you naughty thing!” Spoiled yelled, “get me down from here at once! This is no way to treat a lady!”

“You? A lady?” Diamond asked before howling with laughter, “that’s a fucking laugh!”

“Wha…what word did you just use?!” Spoiled screeched, “oh, I’ll have your tail on a silver platter for this insulting disgrace!”

“Disgrace?” Diamond asked as she shoved her own vagina into her mother’s mouth, “I happen to think it’s an improvement. You’re my puppet, and until you agree to be nice and rehire Dumb Waiter…I think my pussy will make a terrific gag. Now, SUCK!”

Spoiled saw no other way out of this and she began to slurp and bite at her daughter’s nether regions. Diamond howled with absolute pleasure as her mother’s tongue and teeth did their work. She had experienced sex in a foursome with the Crusaders before, but this was so much different. Standing up to her mother was one thing, but humiliating her like this created a level of happiness and joy unlike any other. She grabbed her mother’s mane with her hooves and forced her tongue in deeper.

“Yeah…you like that, bitch?” She asked with biting sarcasm, “mm…I know you LOVE the taste of pony pussy! I’ve seen you with the mares on our staff, and I don’t think Daddy would be too appreciative of the way you treat them!”

“MMMAHEUHJEUBWKEBWIEWKBI!” Came the muffled response of her mother.

“Oh, I’m sorry, what was that?” Diamond asked as she pulled herself away.

“You wouldn’t DARE tell your father about that!” Spoiled growled as soon as she was free.

“Oh, I would…that is, unless you were to agree to be nice and rehire Dumb Waiter.”

“NEVER!” Spoiled thundered, “that putrid, worthless excuse for a stallion was the worst thing that ever happened to this family! I shall not bring him back!”

“Fine,” Diamond said, “then, we’ll just continue.”

She got off of her mother and ensured that the bonds were secure. She then grabbed a whip from under the bed, along with a riding crop. Her mother’s eyes went wide as she realized that they were her own personal implements of sexual torture. She would use them whenever a maid went wrong, beating the poor pony within an inch of her life. Then, she would savagely rape them, and threaten them with death if they told anypony. Diamond had witnessed all of this evil, but had been too scared to do anything about it. Now, she was brave, and she felt her friends’ spirits around her, urging her forward.

She didn’t say anything, but began unleashing a beating on her mother. Spoiled yelled in pain as the whip found its mark over and over again. Once the whip had drawn enough blood, Diamond swapped to the riding crop and smacked her mother’s reproductive organs. Spoiled yelped again, but this time, there was an air of pleasure to the noise. She liked having her pussy, anus, and nipples smashed. Diamond realized this and quickly returned to hitting above her mother’s belt. She didn’t want Spoiled to feel any kind of pleasure from this. This was punishment, and it was not meant to be enjoyed.

“Alright,” she said as she set the whip down, “you lean back…because now the fun truly begins.”

Breaking Tension

Diamond forced her mother’s head back even further, and then told her to open wide. She then spread her pussy lips and relieved herself all over Spoiled’s face. Her stream would have been magnificent to anypony with a fetish for such things, but to her mother, it was the ultimate sign of daughterly disrespect. Diamond’s smile turned even more wicked as her golden shower cascaded upon her mother’s waiting lips and face. Spoiled tried to avoid it, but every time she did so, Diamond would simply yank her head back over into the path. The target was being drenched to the core, and the administrator was thrilled to the teeth.

“Mm…oh my fucking Celestia, it feels so good to humiliate you, Mother!” Diamond exclaimed lustily, “you deserve every single drop of what I’m giving you. It might just be pee, but consider it a reminder. All that I’m saturating your fur with right now represents those ponies whose lives you’ve taken and shredded over the fields and farms of Ponyville.”

“They needed to be shredded!” Spoiled said before feeling more of her daughter’s urine enter her mouth and play with her tongue.

“Nopony needs what you’ve done,” Diamond said as her stream finally finished, “what they need are friends and good neighbors who can be trusted. You are the most untrustworthy pony I’ve ever met!”

Spoiled’s mouth nearly dropped through the bed. “Ah…I’m your MOTHER, young filly! Don’t you DARE speak to me like that!”

“I’ve already gone to the bathroom on you,” Diamond said, “frankly, I see no reason why you should be making threats right now.”

Diamond slid off of her mother’s chest and maneuvered down the bed to where Spoiled’s luscious nipples, glistening pussy, and beautiful rump hole lay. She flashed a smile back at her matron, before going down on her fiercely. Spoiled howled as her daughter bit and grabbed at all of her most sensitive body parts. Pain was the main feeling, but there was an amazing dose of pleasure laced throughout the sensation. She had no idea where her daughter had picked up such an incredible bedroom performance, but she didn’t want it to stop. Her cries quickly turned into moans of deep gratitude.

When this happened, Diamond decided to turn up the pain. She bit down on one nipple and would not let go. Spoiled screamed and cursed, but Diamond’s grip held. The filly smiled to herself as her mother thrashed about above her, crying and squealing for her to release her teeth. But Diamond silently refused, holding down and licking up the milk that suddenly burst forth. Her mother’s lactation was sweet to taste, and she realized that she’d missed nursing at her mother’s bosom. She latched on and fed to her heart’s content, relishing every pain laden scream that came from the evil matron. She knew that she was doing this for her Crusader friends, and for everypony else in Ponyville. Still, though, she also did it for her own satisfaction.

Estrus had enslaved her, and she had been itching terribly. But with her mother at her command, and her friends on her mind, the heat had died very quickly. She loved being able to suckle on her mother’s teat, and when one of them seemed to dry up, she popped over to the other one. It was the same cycle, and her mother continued her agonizing wails. She couldn’t believe some of the language that Spoiled was using, but she didn’t care. She remembered how amazing this had felt when she did it with the Crusaders, and how dirty the words had gotten. She loved hearing the street slang come out of the normally prim and strictly proper Spoiled Rich. It was cathartic in a way, as it showed that her mother truly held some kind of ponydom inside her greedy black heart.

“ALRIGHT!” Spoiled squealed, “CAN’T YOU LET GO OF MY TIT?!”

Diamond giggled. “No, Mother, because we’re not through with your punishment yet. In fact, I don’t know if I’ll ever be done. Perhaps, until Dumb is rehired, we should do this every night! I mean, can you imagine? You, tied up to my bed, helpless and completely at my mercy…and then I come in with the whip and the crop! I could use you as my own personal toilet, too! Then…then, I could fuck you. I could fuck you until you screamed. I could fuck you in your pussy, deny you any sense of pleasurable release, and then jam my big, plastic toy deep inside that anus of yours. As a matter of fact…I think I’ll try that right now!”

She then leapt from the bed and dug out a large strap-on dildo that she’d borrowed from Apple Bloom for this very moment. She put it around her small rump and loved the way that it rubbed against her vagina. She knew she would receive a great deal of happiness from the ensuing punishment, and she knew exactly what to do to garner her mother’s acquiescence to her demands. She got on top of Spoiled, placing the toy right at her mother’s entrance. She could tell of the looseness of the pussy with which she was about to do sexual battle. She just couldn’t believe how much of a whore her mother was!

This is for Daddy… she thought as she jammed herself inside, relishing the scream that came from below. She began violently thrusting in and out of Spoiled, who begged and pleaded for her to stop. But she just went harder and harder, loving every single second of embarrassment and utter degradation that she brought to the evil, greedy matron. Each one of her thrusts was accompanied by a thought of a pony or something else that she was doing it for. One thrust would be for her father, another would be for Dumb Waiter, and a third would be for Apple Bloom. She pounded her mother for the rest of the Crusaders, all of their wait staff, and everypony else that Spoiled had ever mistreated or bullied.

She felt her own pussy grow hot with excitement, and a gorgeous new itch came over it. This wasn’t heat, as it was the same kind of itch she experienced with the Crusaders. She knew that her orgasm was coming, and she’d be damned if she allowed her mother to experience the same feeling. So, when she heard Spoiled’s squeals turn to moans of happiness, she quickly yanked herself out and shoved deep into her asshole. Spoiled’s scream would have woken the dead, and a little bit of blood followed the plastic penis. But Diamond did not care for her mother in the moment. She just wanted to make her feel the way everypony else felt: completely and utterly fucked up the ass.

“MM-HMM! YEAH!” Diamond screamed, “THIS IS WHAT YOU GET, BITCH! THIS IS EVERYTHING YOU DESERVE!”

“OH, YOU FUCKING WHORE OF A DAUGHTER!” Spoiled screamed, “I HATE YOU! I FUCKING HATE YOU!”

Her venom laced words of hatred pierced into Diamond’s heart, but the filly kept going. They screamed horrible things at each other as years of tension and mistreatment finally exploded into one hour-long session of passionate rage. Diamond’s thrusts were so violent and forceful, that Spoiled felt as if she were being ripped in half. Tears filled their eyes as they pounded away at each other, continuing to scream and yell. It became so loud that some of the staff got curious. They found Diamond wailing away at her mother, and some of them tried to stop her.

“Don’t stop me!” Diamond ordered, “I’m doing this for you! She fired Dumb Waiter, and she’s slept with so many of the mare maids! She deserves every single inch of this cock! Now…if anypony would like to join in…”

The staff smiled in glee and quickly whipped out their various penises and vaginas. Soon, the entire room turned into an orgy as the butlers and maids made love to each other, and then forced Spoiled into mating with them. So many of them had been so abused at her hooves. They reciprocated the pain, and then some. A few of them even dared to punch and kick their mistress, and when Diamond had finished orgasming for the fifth time, she allowed every butler and maid to have their way with her. They fucked Spoiled until she fell unconscious, drenched in various bodily fluids, and completely spent from her night. When this happened, Diamond gently ordered everypony to stop and then they all spat on her.

“This is what you’ve brought on yourself, mother,” Diamond whispered, “for the record…I don’t hate you. I can’t speak for everypony surrounding you right now, but for me, your punishment was well deserved.”

Spoiled coughed and suddenly came to. “You…really…gave it to me.”

Diamond smiled. “Yeah, I did…and everyone else did, too. You don’t know how amazing it felt to have our way with you. Now…will you rehire Dumb Waiter?”

“Yes,” Spoiled responded, “I will.”

“Will you be nicer, kinder, and less greedy from now on?”

“Yes, I will. Just please promise that you’ll never put me through something like this again.”

“On my honor,” Diamond said, “and on everypony’s honor here. All I want is for you to be a nice pony, Mother. I want you to accept my new friends, and I want you to quit being so abusive to our household staff. In fact, I think they deserve a raise.”

“A RAISE?!” Spoiled roared as she suddenly came to life, “THEY DON’T DESERVE-“ She stopped and looked at the faces around her. When she saw them returning to rage, she quickly doubled back. “I mean…they don’t deserve such a low pay! Yes! A raise is in order!”

The ponies all cheered, and thanked Diamond for going to bat for them. It took a lot of pain, a lot of rope, and a lot of pussies and dicks…but it seemed that Spoiled had learned her lesson. From then on, she was a nicer pony, and some of her staff said that she was the greatest boss they’d ever had. All thanks to one filly, and some very rich punishment.