Cinderella's "Ugly" Step-Sisters

WARNING: This is a dark story featuring the humiliation and betrayal of people who may not deserve it.

It also features somewhat extreme body types, and some incest.

And remember: this is just a fantasy. Treat the people in your life with love and respect.

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Cinderella gasped as the bell tower gonged again - was that nine? Ten?

"Wait, come back!" A voice called from down the hall, its silhouette appearing in the door. "I didn't even get your name! How will I find you?"

GONG. Cinderella tried to pick up speed, but struggled to keep her footing in her sparkling glass heels. She pushed past the guards at the castle's grand entrance, out onto the long bridge connecting it to the town below.

GONG. Her dress began to glow, slowly unraveling around her with a series of swirls and sparkles. Up ahead, she could see the carriage she had arrived in POP back into a pumpkin. Why had she lost track of time!?Distracted, she stumbled down a short set of stairs, losing one of her heels in the process.

GONG. That had to be twelve. It was midnight. Cinderella gasped as, with a final glow, her dress fully evaporated around her, leaving her completely naked. She tried in vain to cover herself, and scurried off into the tree line, hoping to find a way to sneak home before anyone noticed she was gone.

The guards outside the castle got a nice eye full of a beautiful, skinny young woman sprinting past them fully nude.

Back in the castle, Lady Grey, Cinderella's stepmother, watched the events unfold from a high balcony. She had seen the skinny little bitch at the party, chatting up Prince Phillip. The idiot had thought a clean face and some shiny enchanted dress would disguise her that much? Lady Grey scoffed. Still, Cinderella had snuck off with the Prince just before midnight. Once again, the waif had tried to ruin Lady Grey's plans.

There was a commotion as the Prince re-entered the grand hall. He seemed to be in a slight panic, asking strangers if they had seen the beautiful young girl. Most of the guests merely reeled back, caught off guard by the smell of booze on his breath and his slurred words. That part was Lady Grey's fault - she had bribed one of the servants to keep refilling the Prince's flagon while he was distracted during the ball. Clearly the plan had backfired, though, as the drunken idiot had gone off with the ugly little stick Cinderella rather than the intended targets: either one of Lady Grey's beautiful actual daughters.

Speaking of which, her daughters Anastasia and Drusilla waddled up to her, bulging out of their dresses. "What's wrong, mama?" Anastasia asked.

Lady Grey took another gulp of her wine. "Your little stepsister ruined everything. Again."

Both of her daughters groaned. "I hate her so much," Drusilla replied.

"We all do, sweetie," her mother told her, as her attention shifted back towards the Prince.

A guard had just hurried into the grand hall, and presented the Prince with Cinderella's missing glass heel. The Prince held it delicately in his hand, before holding it up for the room to see. "I shall search the city for the owner of this magnificent glass slipper! Tell the people - any beautiful young woman should expect a visit from me in the coming days. If the shoe fits, they shall accompany me back to the castle, to be my wife."

The crowd murmured amongst themselves. Lady Grey felt someone tug on her sleeve, and she turned to see Anastasia. "Mama, I thought you said one of us would get to be with the Prince?"

"You will, sweetie," Lady Grey replied, more confident than ever.

---

Cinderella sighed wistfully as she finished her chores for the night. The party was everything she dreamed of, and the Prince more so. She wondered why the fairy's magic had to wear off at midnight. She could have stayed with the Prince...

Outside, she heard a wagon arrive. She rolled her eyes. Her evil bitch of a stepmother had just gotten back from the party, along with her two stepsisters. "Ugly stepsisters," she thought to herself, with a snicker.

She walked to the front door, and opened it in preparation. Seconds later, her stepmother Lady Grey walked in.

Lady Grey was once an exceptionally beautiful woman, Cinderella suspected. But her age had caught up with her - she had to at least be in her 50s now - as well as her addiction to her lavish lifestyle. Her hair was salt and pepper, though more grey these days. Her curves had filled out with weight, and a lot of places that weren't curves filled out, too. In truth, Lady Grey was fat, but her stepdaughters made her look small in comparison.

Anastasia entered next - or rather, her stomach did, and then the rest of her. Anastasia was the fattest of Cinderella's stepfamily. Her gluttony knew no bounds, and the weight went straight to her gut before filling anywhere else out. Two gigantic breasts sat wobbling on top of her belly. The result was a woman who looked more round than shapely - like a giant, wobbling ball, Cinderella thought.

Drusilla entered next, though Cinderella could smell her before she did - Drusilla was constantly smoking that vile Elfweed, and the earthy scent followed her wherever she went. As she entered, Cinderella saw her bloodshot eyes and stoned expression. Drusilla was just as fat as her older sister - well, maybe a little less - but it all went to her hips and ass. Most women had to wear padding and elaborate hoops to make their dresses project out behind them, but not Drusilla. Cinderella watched in disgust as Drusilla walked past her, her wide ass wobbling.

Cinderella closed the door, and turned around - only to see her stepmother watching her. "And how has your evening been, Cinderella?" Lady Grey asked, a strange note on her voice.

Cinderella blushed. "Same as ever... mother," she added, reluctantly. "Just did my chores and now it's off to bed."

Lady Grey picked up a bottle of cheap wine that sat in a cabinet near her, inspected the label, and then lazily tossed it at Cinderella's feet. It shattered, sending glass and wine across the room, and splattering over Cinderella's smock.

"Looks like you missed a spot," Lady Grey snidely told her, before turning and leaving the room.

Cinderella sobbed as she got her tools to clean up the mess. Her stepfamily was so cruel to her, and she had no idea why. Why had her nice, innocent father even married that vile, fat, greedy woman?

---

Cinderella's father had married Lady Grey because of her fat ass. Really, that was it. Cinderella's biological mother had died from plague, unfortunately. She had been a sweet woman, incredibly lovely and caring.

But she had also been skinny and dull. He had loved her, certainly, but when she died, he knew what kind of woman he wanted to fill the void with.

And Lady Grey filled that void. She was pleasant and mannered and beautiful, too, but she also had a fat ass. Every night, he would climb into bed and bury his face in that ass, and he knew all of life's miseries were worth it.

Lady Grey had married him, though, for the money. The way he worshipped her body was nice, of course, but anyone could do that. No, she needed his money.

The Grey family was destitute. They were one of the oldest families in the city, their estate was lavish and they continued to keep up appearances. But after years of ill-advised financial decisions, they were poor.

Marrying Cinderella's father put an end to that. She had access to his vast fortune, and her days of worrying about money were gone. She had lived content with that for a few years, but she knew eventually she would need to move onto greater things - in fact, she had her sights on royalty. She just had to get her husband out of the picture first.

And so, when he went off for business one day, Lady Grey bribed the carriage driver to arrange for an "accident."

And as the carriage containing Cinderella's father, having broken loose from its horse, plummeted off a cliff, his thoughts weren't on his beautiful young daughter. They weren't of his lovely dead wife and how they would meet again soon in the next life. No, his last thoughts were of Lady Grey's fat ass, and how he'd never get to see it again.

---

Lady Grey's big, fat ass jiggled as she bounced on the dick beneath her. It was attached to a man, of course, named... Karl? Kenneth? Something with a K. It didn't matter. What mattered was that Karl-Kenneth was the city's best glassblower, and the only one who could make a convincing glass shoe to fool the Prince.

When the idiot refused a large sum of money to have Lady Grey skip the line and finish the glass shoes immediately, she used a different tact - one that she used frequently. The glassblower had been easy to seduce, even with his wife sitting downstairs, tending the house.

And so she bounced on his dick, moaning loudly and erotically, as the mustachioed man huffed and puffed beneath her, his face beet red.

"OH, FUCK," she screamed, "RAM THAT GIANT DICK INTO ME!"

The dick wasn't giant, of course, but truth be told, it wasn't small. It had a certain girthiness to it that Lady Grey found appealing, and as the glassblower reached behind her to grab her fleshy, wobbling ass, she allowed herself to get lost in the pleasure, if only for a brief moment.

The man's breathing picked up, and his face got even redder. Lady Grey knew what was coming - she dismounted, and climbed between his legs. With one hand, she stroked his cock, and with a wink, she lowered her mouth onto his swollen red balls. The glassblower let out a strange, guttural moan, and shook as Lady Grey felt his balls contract in her mouth. Spurt after spurt of cum shot out of his dick, and landed on the Lady's face.

She let him catch his breath, and then stood up. "So, you'll make the shoes immediately, right?"

The glassblower wiped his brow and nodded enthusiastically. "Of course, of course! Anything you want. Uh, let me get you a rag or something-" he replied, but when he looked up she was already leaving the room.

Lady Grey descended the stairs in the glassblower's modest home with a preternatural grace. Beneath her, she could see his wife, awkwardly sitting and avoiding her gaze. She was a pitiful, scrawny little thing. Lady Grey approached her, and put her hand under the wife's chin, raising her face and forcing the woman to look at her.

What the wife saw was a stunningly gorgeous, if aged and fat, woman's face - and it was covered in her husband's cum. Lady Grey could see the wife's face turn red and tears well up in her eyes.

"I did this for a pair of shoes," Lady Grey told her, and then turned and left the home.

---

A day later, and the shoes were complete - and not a moment too soon, as news spread quickly that the Prince and his entourage had started their search. Naturally, they would be visiting the various nobles' homes first, and he would likely be at the Grey estate shortly.

Thankfully, Anastasia and Drusilla's feet were roughly the same size, so she'd only have to switch out the glass slipper once. And she knew how she'd do it.

Cinderella annoyingly had heard the news of the Prince's search, too, and she could barely hide her excitement. She had been walking around the manor singing songs and dancing, and when confronted would smugly act as if she knew something they didn't.

Of course, they DID know - they knew everything. Lady Grey had filled Anastasia and Drusilla in on the plan, and even if Anastasia was a little slow, they both understood the rough idea.

And when the Prince rode up to their estate with his royal entourage, no one in the manor could conceal their excitement - even Cinderella's spirits weren't dampened by the fact that her step mother had locked her in the attic. She just knew true love would win in the end.

Lady Grey had good information that the Prince's most trusted Guardsman would enter the house first, and announce the Prince's presence, and escort any of the house's women outside to try on the magical slipper.

She also had it on good authority that this particular Guardsman had a predilection for... larger women. Apparently he frequented the city's more prestigious brothels, and word traveled.

And so, when Lady Grey and her two daughters heard a knock on their door, they opened it, all three dolled up in their sluttiest, most outrageous dresses. As the Guardsman was led inside, Lady Grey could see the man's eyes almost bulge out of his head.

He announced the Prince, and escorted Anastasia, then Drusilla outside, and announced them. As he re-entered the house for Lady Grey, he noticed she was no longer in the foyer. "Ma'am?" he called out, but before he could take a step forward, Lady Grey emerged from the next room - completely naked.

Only the Guardsman's strict military composure kept him from gasping, but even he could barely keep himself together. The woman was exactly his type - all the women here were, to be honest. She was fat, with soft, round stomach with several rolls on her sides. Her breasts sat lazily against her belly, fairly large and still somewhat firm, even through the woman's years and physique. Her hips were wide and led to large, meaty thighs. He wished this woman was one of the girls at the brothel.

She turned towards the stairs, and looked back at him over his shoulder. "Why don't you... come help me with something in the master bedroom, Mr...?"

Without a second's hesitation, the Guardsman followed her. "Laurel, Ma'am," he replied dutifully. "Captain Laurel."

"Well, Captain," Lady Grey purred, as she ascended the stairs, "I think you'll be a BIG help."

Captain Laurel marveled at the fat, wobbling ass in front of him - and just as they reached the top of the stairs, Lady Grey bent forward, and pushed her fat ass into his face - and then continued on before he could react. Captain Laurel followed with all haste, knowing this would likely be one of the best days of his life.

When they got in the master bedroom, Laurel was startled by the extravagance - the furniture and decorations looked more expensive than some of the rooms in the royal castle. But he was also startled by something else: a pair of glass slippers, almost identical to the one the Prince had in his possession.

He looked quizzically at the Lady Grey. She gently put her hand on his face, and then guided one of his hands to her ass. "Switch out the Prince's slipper for one of these, and I'll do anything you want - whenever you want."

Captain Laurel looked at Lady Grey, then the fake glass slippers - and then out the window, where he could see the Prince waiting on his royal steed.

---

Prince Phillip fidgeted impatiently in his saddle. Captain Laurel was taking forever in this house, and he had no idea why. Judging from the two women who had already emerged from the house, the fair maiden he sought was certainly not from this family. He eyed the two young women fanning themselves near their front porch, their obscenely fat frames bulging out of their slatternly dresses.

He rode forward, closer to the house, and stopped short of the two fat whores. "Captain Laurel!" he cried, "What takes you so long! Surely we do not wish to waste any more of these... lovely... ladies' time!"

"Oh, he'll be out shortly," one of the fat women replied, in a surprisingly soft voice. "He's just helping our poor old mother."

"Mhm," the second woman replied, in a lower, slightly harsher voice. "Our mother needs lots of... help. She's always recruiting the help of strapping, young lads like your royal guard."

"Oh," Prince Phillip responded, sort of dumbly. He hadn't expected the women to engage with him at all - they were nobles, but that didn't mean they should be speaking so casually to their Prince.

He looked them over, now that he was closer. The first one was... round. She looked sort of like a giant balloon in a pink dress, just with giant fleshy tits bulging out the top. And the second one was certainly curvy - she had hips to spare, and a fat stomach and legs to balance her out.

The Prince's initial thoughts were of disgust, but even he had to admit there was something alluring just from the sheer volume of flesh on display. Still, they were nowhere near the classical beauty he remembered from that night. He called again to his Guardsman.

---

Upstairs, Lady Grey was on her back, her legs propped up to her shoulders. Above her, Laurel was pistoning in and out of her tight asshole. With each thrust, he looked down at her massive frame wobbling and jiggling - and when she grabbed her tits and squished them together, it pushed him over the edge as he watched them bounce back and forth. Stifling a moan, he unloaded into her bowels, and quickly pulled out.

"Now, as promised, switch out the slippers when you return outside. And I'll uphold my end of the deal," she instructed him. Honestly, she would be happy to fuck this man regularly - he was large, both tall and muscular, but in a more naturalistic soft kind of way, rather than a bodybuilder. He had swarthy skin and a nice face - and a giant cock.

Captain Laurel nodded dutifully, helped Lady Grey into a more modest dress, grabbed the fake slipper and led the Lady outside.

---

Outside, Prince Phillip was ready to get one of his other Guardsmen to go inside and see what was going on - when finally, the doors reopened and Captain Laurel led another fat woman outside.

Phillip sighed. This one may not have been quite as fat as the other two, but she was clearly middle-aged. This was still the wrong house, and they'd wasted so much time.

"Captain, get the slipper," the Prince commanded, unenthusiastically. This was already becoming a chore, and not the grand romantic adventure he had hoped for.

The Captain returned to his horse, and fished out the real glass slipper - and quietly tossed it into the garden bushes. He palmed the fake one provided by Lady Grey, and feigned pulling it out of his pack.

He returned to the front of the house, where the Lady Grey and her daughters waited, all three sweating and red in the afternoon sun. He motioned to the first woman, the particularly round one in the pink dress. He knelt down and prepared to slide the shoe onto the woman's foot.

Anastasia approached the Guardsman, kicked off her own shoe, and held up her fat foot. Captain Laurel slid the shoe onto her - and it fit perfectly.

The Prince's entourage gasped as they saw what happened, and the Prince, startled, looked down at the obese woman, and saw the slipper sitting perfectly on her foot. "That- I can't- she's not-" he stammered.

Before he could formulate a thought, however, Drusilla stormed up beside Anastasia, and shoved her aside. "My turn, dummy."

Captain Laurel removed the slipper from Anastasia, and slid it onto Drusilla's foot. It also fit perfectly. The crowd murmured in confusion and gossip.

Laurel looked up at his Prince. "Your highness, it seems one of these women is the fair maiden you've been searching for!" He turned back towards them, and asked them their names again.

He stood back up. "The Ladies Anastasia Grey, and Drusilla Grey," he announced to the Prince and his entourage.

The Prince looked horrified. These were not the kind of women who he wanted to be seen with - and definitely not after organizing a highly public quest to find the woman he was so enamored with. "Captain, I- these are NOT the woman I was with the night of the ball!" he declared, trying to save face.

Captain Laurel cleared his throat, "With all due respect, Your Highness, you were VERY... shall we say... inebriated that night. Your memory may be slightly faulty."

Prince Phillip grew bright red, and was caught off guard. "Okay, but... which one of you was with me that night? It couldn't have been both of you."

Anastasia politely curtseyed, "It was me!" she declared, in her buttery smooth voice.