Cinderella's "Ugly" Step-Sisters

Drusilla shoved her again. "Lying isn't becoming of a lady, Ana. It was me. We had a VERY special night-"

The Prince cut her off. "That's enough! We'll just have to..." he eyed Captain Laurel, looking for advice.

Instead, Lady Grey interrupted, and stepped forward, next to the Captain (with his cum still leaking out of her asshole). "You'll just have to take both of them back to the castle, and court them. Surely, with a love so epic as the one you've been describing, you'll be able to tell who it was very quickly. And I, of course, will accompany them - it wouldn't be right to separate two innocent young maidens from their poor old mother, would it?"

Before the Prince could answer, Captain Laurel ushered the three women to the large carriage in the midst of the entourage. The carriage sagged lower to the ground was each of the fat women was loaded inside, and as it rode off, it nearly scraped the ground.

The Prince, mortified, followed at the back of the entourage.

---

Inside Grey Manor, Cinderella had finally broken the lock on the attic door, and climbed the ladder down. She rushed to the window, and swung it open, ready to see her true love waiting on horseback outside.

Instead, she saw only the dust of the Prince's entourage receding into the distance. She scanned the estate for her stepmother and hideous stepsisters, but saw no sign of anyone. Something had gone horribly wrong.

Still, she saw something glittering in the garden bushes...

---

Back at the castle, Prince Phillip sulked while the new guests were set up with rooms. He was starting to think that basing a quest on the drunken recollections of a admittedly very horny young man was actually a foolish idea. And now he looked like an idiot, and his subjects were all thinking he had some sort of fat fetish.

He sighed, looking up at the portrait of his parents, the former King and Queen. They had died when he was a teenager. By all rights, Phillip should have been crowned King after their deaths - and, indeed, he performed all the royal duties of one - but they had decreed in their will that Phillip would have to marry before he could be officially named King.

Admittedly, he understood their reasoning. When he was younger, the Prince had been... less responsible. He would party, and shirk his responsibilities, and flirt endlessly with any cute girl he would see. His parents were always trying to get him to settle down and understand his role in the kingdom, and had intended to arrange a marriage with a princess from a neighboring kingdom.

He shook his head. He had met that princess once - what was her name? Pale White? Really Fucking White? Whatever it was, she was an unimaginably fair and gorgeous young woman, small and petite if a little ditzy. But Phillip wasn't interested in an arranged marriage - while he had grown much more responsible since his parents' death, he could never suppress all of his old romantic desires. He wanted that classic romance, one where he would marry a woman he actually loved, like he remembered his parents had done. And he definitely didn't love the White girl.

And so he had started his stupid quest to find the fair maiden from the night of the Ball. And what he got were two overweight whores. He was certain neither one of them were the girl from that night, but Captain Laurel was right... he was drunk off his ass.

He sighed, looking again at the portrait of his parents. They looked so stately and proper, with indescribably perfect features and builds. He tried to imagine his own version of the portrait now, with him, a stunning classic hunk of a man, and that one girl he just brought back with the massive round belly and tits spilling out of her clothes. Or with the second girl, her hips and ass taking up most of the frame.

Despite himself, he had to suppress a laugh at the idea. He shook his head - all he had to do was make it through a date with each of them, and then he could kick them out and find the real girl he was looking for.

He had his servants change his outfit into more suitable eveningwear, and he told one of them to go fetch the first girl, Ana-whatever. The round one.

---

Across the castle, Lady Grey and Drusilla pulled with all their might to get the dress around Anastasia's portly frame. With a final grunt, they pulled it tight and secured the laces. They sat down, all three of them red and panting.

"You look awful," Drusilla teased. "Like a big roly-poly prostitute."

Lady Grey whacked Drusilla's shoulder with a gloved hand. "Be nice to your sister. No man could resist such a sweet, innocent beauty like Ana."

"Whatever," Drusilla replied, and went over to a small table to roll an Elfweed cigarillo.

"You really think he'll like me?" Anastasia asked her mother, ignoring her sister's comments.

"Sweetie, he's going to LOVE you, with a body like that. I've seen you with the boys you bring home - how many of them left without proposing marriage?" her mother replied.

Anastasia giggled. It was true, after a night with her, almost any guy had tried to keep her for their own. She knew enough to turn them down, though - her mother had always told her she'd be marrying big.

There was a knock on the door, and a proper, if weak-sounding, voice announced, "His Majesty the Prince Phillip awaits the Lady Anastasia Grey."

---

The Prince sat slumped against the feast table, arm holding up his head. As he heard his servant and the fat lady approach, he made a half-hearted attempt to regain his composure and act properly.

When the woman came into view, Phillip was caught off guard. She was stuffed into a beautiful bright red dress, with intricate detail work and lace. The dress would have looked elegant on a woman half her size, but on her it bordered on obscene. Her enormous belly stretched the top and middle of the dress to its limit, and her massive, fleshy tits spilled out of the top-small cups of the front, creating a gigantic canyon of fat cleavage.

Again, he was equal parts disgusted and impressed by the sheer amount of flesh in front of him. Still, he couldn't deny she looked nice. He stood up and bowed, "M'lady," he choked out.

The woman gave a polite curtsey, and sat down at the table. The Prince motioned to the servant. "Anastasia, right? What can my servant here bring you for supper?"

Anastasia's eyes lit up. "What do you have?" she replied.

An hour later, and the food had been brought out. While the Prince nibbled quietly on the pheasant in front of him, he watched Anastasia absolutely devour enough food for three or four people. Despite himself, Phillip was impressed. There was something admirable about not fighting your figure, and instead feasting on what you truly wanted. And there was something about the pure hedonism of it...

Truth be told, the wait for dinner hadn't been bad. Anastasia seemed a little dim, but once she got going, she could really talk your ear off. And listening to her talk was a pleasure in itself - her voice was so smooth and soft, and glided like distant bell-chimes through the air.

They spoke of their childhoods, and parents, and what they liked to do for fun (Phillip liked to hunt and ride the country on his horse; Anastasia liked to sit by the window with a dessert and have her servant read her a story). Anastasia might not have provided much wisdom, but she sure was nice to listen to.

Soon after, Anastasia had finished the rest of the food on the table, and leaned back, a little red from the exertion. Phillip let her sit for a bit, and then suggested, "Would you care to accompany me to the balcony?"

He out his arm, and she hooked hers around it, and walked alongside him to the balcony. Phillip couldn't help but notice how soft and squishy her arm was, or the fact that she was wide enough that his arm was pressed against her fleshy side - and would rub against the side of one of her gigantic, wobbling tits as they walked. There was something... pleasant? Exciting? Different? About the whole experience.

Anastasia gasped as they got to the balcony, and Phillip couldn't help but smile at her. The view was stunning - the city below the castle was lit up against the dusk sky, and the deep forests around the city led to sunset-lit mountains. Phillip pointed out a few of his favorite spots across the land.

"It's sooo lovely!" Anastasia gushed. ""And it's all yours?" She asked, looking up at him with wide, twinkling eyes.

He nodded. "How about some dessert?" he suggested. "I'll have one of the servants bring out a selection of our finest treats."

And so a few minutes later, a cart was wheeled out, full of cakes and pastries and puddings and creams. Anastasia leaned back in her seat, and looked towards the Prince. Strangely, he knew what to do.

He grabbed a dessert he was particularly fond of, and pulled his own chair closer to the woman. He scooped some of the dessert onto his spoon, and guided it towards Anastasia. She opened her mouth and accepted the food, moaning with pleasure at the taste.

They didn't say anything for the next half hour or so - Prince Phillip wordlessly watched the woman as he fed her dessert after dessert, and Anastasia looked happier after each one. Phillip studied her face with each bite, and came to realize that she was actually quite beautiful. Her skin was flawless, her eyes large and brown. She had freckles across her cute button nose and chubby cheeks, and her hair was dyed a subtle pink-brown, and cut into a fashionable bob with bangs across her forehead. Even her wobbling double chin fit her face - Phillip tried to imagine her skinnier, but it didn't seem to work. For whatever reason this was just how her face SHOULD look.

As Anastasia finished a rich piece of cake, the Prince reached across her, and rubbed some frosting from the corner of her mouth. As he did, Anastasia grabbed his hand, and popped the frosting covered finger in her mouth, licking it clean. She could see the stunned look on the Prince's face, and knew this was her chance.

"Let's go back to your room," she said, not a mere suggestion.

The Prince wordlessly rose from the chairs, took her hand, and led her to his bed chambers. He wasn't sure what was happening, but there was something so alluring about this woman who unabashedly sought that which gave her pleasure. He found himself wondering what kind of pleasure he could bring her - beyond feeding her treats on the balcony.

When they entered his bed chambers, Anastasia stood in front of him, facing away, and raised her arms slightly, and waited. It took Phillip a second to realize she was waiting for help removing her dress. He obliged, and clumsily worked the back laces. A few minutes later, and the dress spilled to the floor, revealing the naked form of Anastasia Grey.

From behind, he could see her hips and ass unhidden by the large dress. Contrasting the rest of her body, they were sort of narrow and small. Well, comparatively small - if that ass had been on a normal sized girl, it likely would have been massive. But compared to her rotund stomach and boobs, they looked quite small. And yet somehow she made a complete package - her proportions worked for her.

Anastasia turned towards the Prince, completely confident in her wobbling, jiggling body, and started undoing his clothes. Soon he was naked, and he watched Anastasia's gaze go up and down his body.

At his crotch, Anastasia let out a small gasp. Phillip was used to that reaction, be it good or bad - but his dick was massive, and he was proud of it. But as he looked down at himself, he realized something - he was incredibly hard. All because of this massively fat woman he'd spent the night talking to and feeding.

Phillip expected her to drop to her knees, like most women did, but instead she pushed him back towards the bed. As he laid on his back, he watched her body jiggle as she approached the bed and climbed up - and then climbed over the Prince, and kept going until her fat pussy was hovering over his face. She lowered herself down, and ground her pussy against his face.

Phillip was once again caught off guard - this was certainly something he'd never experienced before. Sure, he'd occasionally deign to put his mouth on the women he'd slept with, but they'd never been the ones to initiate it, and they had certainly never sat on his face.

After a moment of worry, Phillip surrendered to the act. There was something so... sexy about his head being completely enveloped by this woman's flesh, her hips, her inner thighs. He stuck out his tongue, and worked feverishly to find her clit, while taking short breaths where he could. He reached his arms up, and grabbed Anastasia's fat little ass, and squeezed, guiding her as she gyrated her hips.

Above him, Anastasia writhed in pleasure, he eyes screwed shut and her face flushed red. She started grinding faster, and after a few seconds longer, she cried out as he body shook. Between her legs, Phillip gasped for breath has Anastasia's legs and pussy spasmed around his face.

As Anastasia finished orgasming, she slid forward slightly, until her tight asshole was rubbing across the Prince's face. He'd never considered touching a woman there, but without thinking, he stuck his tongue out and licked. And once he got his first taste of ass, he knew he needed more.

But that would have to wait. For now, Anastasia slid off of him, and plopped down on her back, shaking the bed frame. Phillip, no longer being crushed beneath her giant frame, got up, and moved above her. He grabbed her meaty legs, and rested them on his shoulders - and then lined his dick up with her pussy, and plunged in.

Anastasia gasped - this was the biggest dick she'd ever had, and it was stretching her out. Phillip gasped, too - not only was this the tightest pussy he'd ever fucked, but each time he thrust into her, her entire body jiggled beneath him, and he was enamored with the sight. He used to love watching a woman's breasts bounce as he fucked them, and with Anastasia, it's like her entire body was a bouncing breast.

As he picked up his pace, he leaned forward, and Anastasia wrapped her legs around his waist. Phillip was in heaven, his body pressed up against and wrapped up by her giant, fleshy body - and it was so soft and sexy.

He slammed into her a few more times, and screamed out as he unloaded into her pussy. He collapsed on top of her, and she wrapped her arms around him. He drifted off to sleep wrapped in this fleshy paradise.

He awoke soon after, a little embarrassed. Anastasia was still awake, and looking at him. For the first time, he kissed her, and her mouth was just as soft as the rest of her body.

"That was amazing," he said, softly, then chuckled. "How about I get one of the servants to bring us more food, and we have a bit more fun?"

---

Across the castle, Drusilla pouted. She exhaled a thick stream of Elfweed smoke, and turned towards her mother, whining in her stoned drawl. "Moooom, the Prince is gonna choose stupid Ana..! They're probably up there... fffucking each other's brains out!"

Lady Grey rolled her eyes at her daughter. "Of course they're fucking each other - it's well past midnight, what the hell else would they be doing?"

Drusilla continued to pout and puff away at her third Elfweed cigarillo of the evening. Lady Grey opened the window again to let out some of the smoke - sure, she loved Elfweed too, but she needed to keep her wits about her.

She returned to her daughter, and gently cupped her face with her hands. "This is a good thing. Or did you forget the plan?"

---

Prince Phillip woke up late next morning, his head resting on Anastasia's giant belly. He jumped up, the morning-after shame hitting him quickly. He watched her sleep for a moment, and then gently shook her.

Without looking her in the eye, he told her, "Ahem, I, uh- I have some... royal matters to attend to this morning, so if you'd please-"

Anastasia giggled, sat up and kissed him. "Okay, I'll leave you be."

The Prince watched as she wobbled off the bed, and as her body jiggled while she gathered up her clothes, Phillip could feel his dick start to stiffen again, to his great shame.

"I'll, uh, help you into the dress and get a servant to escort you back to your chambers," Phillip said as he swung his legs over the side of the bed

Anastasia giggled again, "No, that's okay. I bet I can find the way," she replied, and then, still naked with her clothes in a bundle in her arms, she stepped out into the hallway and disappeared around the corner. Prince Phillip flushed red as he imagined the servants seeing the freshly-fucked fat woman wandering the halls completely naked, covered in his dry cum. He didn't know how he'd live that one down.

Still, through all the shame, he had to admit that that was one of the most fun nights of his life, even if it wasn't the girl he remembered from the Ball.

Well, only one more date and then he could sort all this out.

---

As Anastasia returned from her bath, Drusilla glowered at her. "Always hogging the boys, distracting them with those giant tits and big fat belly," Drusilla complained. "Well, I'll show the Prince what a REAL woman looks like," she said, shaking her gigantic ass.

"Oh Silly, we're BOTH real women," Anastasia replied with a giggle.

Drusilla turned a bright red, and went to slap Anastasia before calming down. "I hate it when you call me Silly. It's not a cute nickname! Why can't you call me Dru?" she whined.

"'Cause you're Silly, silly." Anastasia replied.

From the other room, Lady Grey once again rolled her eyes at her squabbling daughters. Still, some healthy competition would make the girls try harder, and make the plan more likely to succeed. She entered the girls' bed chambers, and started helping get Drusilla ready.

Her dress showed off less cleavage, but it cinched a bit at the waist, and the skirt portion had no structure to it. That way, the Prince could see Drusilla's incredibly shapely hips and butt - plus, they have arranged a little surprise beneath the dress.

Drusilla smoked like a chimney that day, as she usually did before seeing a boy, and by the time evening rolled around, her eyes with little more than bloodshot slits, her eyelids too heavy to keep open.

"Oh Silly, why do you smoke so much of that Elfweed?" Anastasia asked her sister.

"It calms me down. And plus, it makes the sex feel soooo much better," Drusilla informed her, completely missing the derogatory nickname this time.

---

Prince Phillip could smell Drusilla approaching before he could see her - it wasn't a bad smell by any means, but it was that sort of sticky-sweet earthy scent that he knew came from Elfweed. He wasn't a smoker, but he would smell it on his visits into the city, and on some of the courtesans at parties.

When he did see her, though, she looked gorgeous. Or maybe gorgeous wasn't the right word. Sexy..? She was wearing a simple but elegant green dress, and as she walked, he could see the dress cling to her massive hips, butt and legs, allowing him to see every movement. While her chest wasn't as big or on display as Anastasia's was, her exaggerated hourglass figure made up for it.

At the very least, through all of this, the Prince was learning to appreciate other body types, even if they weren't to his normal taste.

Drusilla and the servant escorting her approached the table, and then Drusilla stopped, and glowered at the servant. There was an awkward few seconds as the servant tried to puzzle together what was wrong - and then looked at the table, and pulled out the seat for her.

"It's hard to find good help, isn't it?" Drusilla asked the Prince, as the embarrassed servant scurried away.

The Prince cleared his throat. "I, uh, I apologize for my servant's obliviousness. She will be seen to at once."