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(this ended up taking a life of its own - it's a bit long, but I decided not to split it. It's a work of fiction. Really.)
Long ago in a faraway land there was a young woman named Sinderella. She lived in a small village with her stepmother and two stepsisters, Tegan and Greneril, in a house that had once belonged to Sinderella’s father. Alas he had died shortly after marrying Sinderella’s stepmother.
After his death money became short and they were unable to keep the household staff. It fell to Sinderella to take care of her stepmother and stepsisters and soon her stepmother, who had never much cared for Sinderella, came to treat her as little more than a servant. She forced her to spend her days cooking and cleaning, she took away Sinderella’s clothes leaving her only a few old tattered dresses to wear, and she forbade her from leaving the house alone. Sinderella was grateful for the company of an old woman who had recently arrived in the village and who passed by the house periodically. She lent Sinderella a sympathetic ear and gave words of encouragement.
“My child,” she would say, “Grieve not today, for tomorrow always dawns.”
When the others went out to the market or to visit the nearby town they would leave Sinderella behind to continue her housework, but in fact it was then that Sinderella could relax. She would head upstairs and watch herself in the mirror as she played with her pussy, and sometimes she would finger her ass. For you see, Sinderella was quite the whore.
Not a whore who took money from men in exchange for pleasure, mind you. No, Sinderella was a whore in the sense that she loved sex and cock and cum and took great joy in allowing others to use her body. Her father had been a merchant and when he travelled she would often entertain gentlemen at the house. She liked best of all to take several men at once, opening her mouth wide so she could gag on their cocks, then spreading her legs to allow their tongues to probe her moist folds and their cocks to sink deep into her steaming fuck hole. But most of all she loved it up the ass. She simply could not get enough of being reamed in her tightest opening and taking their loads deep in her bowel. She was blessed with a sphincter of great abilities - elastic enough to accept the thickest of cocks, but strong enough that she could milk a cock dry.
Sadly Sinderella was no longer able to enjoy such activities, and had to be content with her brief times alone. She told the old woman of her plight.
“My dear girl,” said the old woman sympathetically, “You must never deny your true needs.” She also told Sinderella of how various vegetables could substitute for cock.
One day the others announced that they were spending the entire afternoon at a party to which Sinderella had not been invited. After they left she headed to the barn of the neighbouring orchard, hoping that the orchard-boy Tom was there. She had long ago learned of his fondness for pussy and he enjoyed receiving blowjobs nearly as much as she enjoyed giving them. His was the only available cock to satisfy her cravings and she called on him whenever she had the chance.
Sinderella entered the barn but soon saw that there was nobody inside. Deciding not to waste the time she had, she went to the shaded far corner where there was a stool and took her panties off. She sat on the stool, leaned against the wall and pulled her dress up to her waist. Her fingers went to her already-moist pussy and she started to slide her fingertips back and forth along the lips. A jolt went through her body as she grazed her clit, and she started to massage it gently. She reached down the top of her dress with her free hand and squeezed her nipples which had become stiff and sensitive. She increased the pressure on her clit, rubbing faster and faster until a pulsating wave of pleasure hit, coursing through her body again and again, as she shuddered and moaned. Once the sensation had passed she brought her fingers to her mouth and licked them clean of pussy juice. Reaching again between her legs, she eased two fingers between her still-swollen pussy lips and started fucking herself.
Sinderella sensed that she was no longer alone and when she opened her eyes and looked towards the barn door she could see a figure silhouetted in the doorway. As it came closer she saw that it was Tom the orchard boy.
He walked to the corner of the barn and started undressing. He had a fine physique, honed by hours of toil amongst the fruit trees. When he took off his trousers his erect cock leaped out, pointing stiffly in the air. Sinderella also disrobed, revealing her the damp curls of her swollen pubic mound and her full breasts, her nipples still stiff. She squatted down and grasped the shaft of his cock, stroking it gently before taking the end into her mouth. One hand again started rubbing her clit as she sucked Tom’s cock. After a few moments of this she took his cock out of her mouth and turned around, resting on her hands and knees. Tom knelt behind her and taking hold of his cock he guided it to her dripping pussy where it easily slid in. After pausing for a moment he placed his hands on her hips and with slow deliberate strokes started to fuck her. Reaching between her legs she once again began fingering her clit and since she was still riding the wave of her first orgasm her climax took almost no time. As she cried out in pleasure the spasms of her pussy brought Tom to the edge. He leaned forward and grabbed a breast in each hand as with a final powerful thrust he spewed his seed into Sinderella’s belly.
As they dressed Sinderella thanked Tom for his help.
“Not all, Sinderella” he said. “As always it was my pleasure.
Sinderella’s stepsisters tended to wear clothes that were more revealing than they needed to be and although each was attractive in her own way it seemed to Sinderella that they were both trying to be something that they were not. Particularly when it came to relations with men.
Often they would tell Sinderella of some tryst or other - their mother seemed less concerned with their whereabouts than Sinderella’s - and they would boast of acts that Sinderella considered most mundane.
“As he licked my pussy he stuck a finger up my ass!!” Greneril bragged after one encounter. Sinderella fought the urge to tell her about the time she had taken two cocks up her ass at the same time.
“He came in my mouth and I swallowed it all!” squealed Tegan while Sinderella thought fondly of the time when four men in turn had unloaded over her tits and she had licked them clean.
None of the others had any idea that Sinderella was a such a slut; in fact her stepmother would even mock her for being a prude. She had no intention of correcting them.
As the orchard was preparing for harvest it became more difficult to find time to fuck Tom and so Sinderella struggled to satisfy her craving for cock, even as her stepsisters continued to boast of their exploits.
“I did two men last night! Well, I gave one a blowjob while the other played with himself and came over my tits”
“I let a man fuck my ass - it almost went all the way in!”
One day a notice arrived at the house. Tegan read it aloud.
“‘By order of the King,’ she read, ‘all unwed ladies aged between 18 and 30 years are invited to the Royal Palace at the end of the month to attend a Masquerade Party in honour of the Prince’s Balls. The lady who can best satisfy the Prince will be asked for her hand in marriage.’”
“Marriage?” Sinderella’s stepmother exclaimed. “Why, this is wonderful! If one of you two can satisfy the Prince then we’ll all be royalty! How does he require satisfying?”
“Oh dear,” said Tegan as she read on. “‘The Prince longs for a fair slut who can take his Royal staff up their nether passage’. Mother I’m worried. The Prince has quite a reputation after all.”
And indeed he did. For it was known throughout the land that the Prince was endowed with a cock of great size. Firstly, it was of an imposing length. But it was the girth that was truly impressive. A single hand could not encircle it, and it had proved a challenge for many a mouth. It was a rare woman who could fit such a tool in her pussy, let alone her ass. But, listening from around the corner, Sinderella felt that if there was anyone who could satisfy the Prince it would be her.
The end of the month was only a few days away and the stepsisters wasted no time in preparing. Being inexperienced in such activities they initially neglected to use lubrication. When she suggested that they should use something to ease the process they sneered at her.
“What do you know about anal sex?” jeered Greneril “I’ve managed to get two fingers in there and it’s only taken a couple of days!”
Sinderella left them alone, returned to her room and fisted her ass.
The day of the party arrived. Tegan and Greneril were dressed, each wearing a tight black dress, cut so low that that they practically showed their nipples. Their ornate jeweled masks covered most of their faces. Their mother beamed at them.
“My dears, I’m sure one of you will give the Prince exactly what he needs.”
Sinderella entered the room dressed in one of her few remaining good dresses, pale blue in colour and of modest design. She held a simple mask that she had made from scraps of paper and was not wearing panties.
“What do you think you’re doing?” asked her stepmother.
“I’m going to the attend the Prince’s Balls,” she said.
“Ha!!” cried her stepmother. “You? Do you think the Prince longs for a frigid servant girl? I’m not going to let you ruin this evening!”
She grabbed Sinderella, dragging her towards the kitchen and the cellar. She tore Sinderella’s mask from her hands as she pushed her through the cellar door to the back of the room. She ripped the mask into little pieces, scattered them across the floor, then slammed shut the door and locked it from the outside.
“Now stay put while we find ourselves a Prince!” she snarled out as the three of them left.
Sinderella tried to open the door but it was no use. There was no way out and she was going to miss the chance to let the Prince fuck her ass. She could hear the clatter of hooves as the carriage left the house.
A few minutes later the key turned and the cellar door opened. It was Tom.
“Oh, Tom!” Sinderella cried as she threw her arms around him. “Thank you so much!”
“I heard the commotion and thought you could use some help. You don’t want to miss the big night, do you?”
“No I don’t, so thank you again. However can I repay you?”
Tom paused. “Well, do you need to warm up for the party?”
Sinderella smiled at him. “Of course I do - thank you for offering.”
She reached out and started to rub his cock through his trousers. She stepped forward into his arms and his hands pulled the back of her dress up, revealing her bare ass. He led her to the kitchen table and she hopped up, leaning back and spreading her legs as he buried his face between her thighs. His tongue started darting in and out of her pussy, lapping up her flowing juices, as she started to massage her breasts. Standing up her took his trousers off and guided his cock into her waiting pussy, slowly thrusting back and forth. After a few minutes he withdrew his cock and knelt down again. This time Sinderella pulled her legs back further, exposing her asshole. She felt Tom spread her cheeks wide and then she felt the firm moistness of his tongue probe her tight opening. She relaxed as he increased the pressure of the tip of his tongue against the sphincter, which eventually gave way allowing him into the depths of her rectum. She moaned as his tongue swirled around, lubricating her passage with his saliva. Standing once more he placed his cock head against her ass and with gentle pressure slid his cock into her. This time he fucked her with short, sharp thrusts. She pulled the front of her dress down to expose her breasts and he took one in each hand, pinching the nipples as he ploughed into her. Before long his breathing became rapid and his cock became more rigid and engorged and finally he let out a grunt as a great load of jizz exploded into her ass. She squeezed him with her ass muscles, milking the last of his cum from him, before he finally withdrew.
“Thank you for stretching me out Tom, but how am I supposed to get to the castle? The carriage is long gone.”
“I may be able to help with that, my dear” said an old voice.
Sinderella and Tom turned to see the old lady from the garden standing in the kitchen doorway. The two of them started to cover their naked bodies.
“Oh, you don’t need to bother with that” she said. “I’ve seen it all in my time.”
“Do you have a carriage that I could take to reach the Prince’s Balls?” Sinderella asked.
“Not at present” the old woman replied. “But I’m sure I can provide something suitable.”
With that she walked over to the table and stuck two fingers into Sinderella’s still-gaping ass. Sinderella gasped with surprise.
“It’s alright my dear” the old woman said as she scooped a glob of cum from Sinderella’s ass. “Come with me” she beckoned as she led them outside.
“It was not by chance that I came to this village after your father died. I have been watching over you since then, helping you meet your needs. For you see Sinderella, I am your Fairy Godmother.”
And with that the old woman flung the cum from her fingers. With her other hand she took a wand from her robes and muttered a spell. A flash of light flew from the end of the wand towards the pool of cum on the ground and suddenly there appeared a magnificent gilded carriage, pulled by a pair of fine white horses.
“Is this was you were hoping for?” the Fairy Godmother asked.
Sinderella could hardly believe her eyes.”Yes, thank you! How wonderful! Oh - but what about my mask? My stepmother broke it.”
The Fairy Godmother reached up to Sinderella’s face and smeared cum across her cheeks. She pointed her wand at her and the most ornate mask appeared on Sinderella’s face. A pearl necklace appeared around her neck.
“You look beautiful” said Tom. “I’m sure you’ll take the Prince’s cock all the way up your ass”
“The one thing you must remember is that this magic will last only until midnight so you must leave before then” the Fairy Godmother said. “Now, be on you way - the horses will know their destination.”
Sinderella thanked Tom and her Fairy Godmother again and climbed into the carriage. As soon as sat down the horses took off. She turned to wave goodbye and saw that her Fairy Godmother was kneeling in front of Tom, sucking his cock.
Before long, Sinderella arrived at the palace.
When she entered the Main Hall she found that a tremendous fuck-fest was underway. There was a great crowd of people, comprised mostly of young women from all over the land, all wearing masks, and in various states of undress. A number of chairs and beds were laid out in the Hall, and small groups crowded onto and around these. A few men were scattered throughout, fucking various women in turn, and some women were wielding dildos made of glass and ivory, and holding bottles of oil. Sinderella realised that rather than guests, these were palace staff charged with ensuring the women were sufficiently wet and stretched for the Prince.
At the far end of the Hall was a raised platform on which had been placed a large bed. And standing next to the bed, having his cock sucked by two women who were kneeling in front of him, was a young man whom Sinderella recognised as the Prince. Even from across the Hall she could tell that his organ was of daunting dimensions. As she watched, one of the women stood up, turned and climbed onto the bed on her hands and knees with her ass in the air, and the Prince attempted to enter her. After a few moments he shook his head and the woman was led away. The other woman took the same position but with the same outcome. Soon another two women were brought to the bed and the curious dance repeated itself.
Sinderella understood that this was how the Prince hoped to find his perfect bride - any woman whose butthole could take such an organ would be a treasured find. Sinderella intended to be that woman.
She went to a side table laden with dildos of various sizes and selected one made of glass. It was of great size and was designed to mimic the shape of a real cock. Taking a bottle of oil she went to a nearby bed and proceeded to coat the glass dildo. A few people noticed what she was doing and murmured their surprise that she would try such an object. She knelt on the bed with her face in the sheets and placed the tip of the phallus against her asshole.
At first it seemed that she had taken on too great a task, for her ass would not allow the dildo to enter. But Sinderella relaxed and took deep breaths as her sphincter slowly stretched, and as she continued to push the tip sank deeper and deeper between her ass cheeks. Those watching gasped as inch by inch the dildo disappeared up Sinderella’s ass and when the only the flared base was visible they started to applaud. With small thrusting motions she started fuck her ass, and was so aroused that that her pussy started to drip.
“Young lady, you will come with me,” said a stern voice. Sinderella opened her eyes and saw an older man wearing the Royal crest. She pulled the dildo out of her ass and followed him towards the front of the Hall. On her way she recognised her stepsisters in their masks, unenthusiastically giving hand-jobs to a couple of courtiers.
“Your Highness,” said the man as they reached the platform, “I believe we may have found a candidate.”
Sinderella paused nervously as she came face to face with the Prince, still wearing her mask. Remembering her manners she curtseyed and as she bowed her head she got her first proper view of the Prince’s cock. And such a cock it was! Certainly she had never seen the like. It was now semi-flaccid, but even so it would have dwarfed most men’s erect cocks.
The Prince pointed to the the glass dildo that Sinderella was still holding. “It is a rare woman who can take such a thing in their pussy, let alone their ass. Could you demonstrate your abilities?”
“With pleasure, Your Highness.” she said as she lay back on the bed. Lifting her knees to her chest she once again placed the dildo against her darkest opening and eased it deeper and deeper in. The Prince took hold of the dildo and started to fuck her ass with it, while stroking his cock with his other hand. Leaning forward he put his face between Sinderella’s legs and started to eat her pussy.
After a while he removed the dildo from her ass and stood up. Sinderella slid off the bed and knelt in front of him. With both hands she grasped his cock - it was wider even than the glass dildo and even with two hands her fingers could barely meet. She pulled back the foreskin and took the mushroom head in her mouth. Opening her mouth as much as she could she was able to take it to the back of her throat but even then there was room for both hands on the shaft. She lay back on the bed as the Prince coated his cock with oil.
“Please tell me if I have to stop,” he said as knelt between her legs.
Holding his slick cock in one hand he pushed against Sinderella’s ass. Little by little her hole opened and as he increased the pressure she could feel it about to penetrate her ring. With a final effort she bore down on his cock and then suddenly the tip was in. With a gentle rocking of his hips the Prince sank deeper and deeper until his balls came to rest against Sinderella’s ass-cheeks.
The watching crowd let out a cheer, as the Prince paused to allow her ass to get used to his cock. Then he started to slide his cock in and out, slowly at first, but with increasing speed and depth. Sinderella reached down and started to rub her clit, moaning with pleasure, as he leaned forwards and started sucking on her nipples. A wave of pleasure started to build deep inside her and then her body tensed as a powerful orgasm ripped through her. He did not stop his pounding of her ass and before long she came once more, her whole body spasming, as she let out a guttural grunt. The Prince too started to moan as his thrusts grew faster still, until with a cry he buried his cock to the hilt and released a gush of cum into her rectum.
The whole Hall broke into applause as the Prince collapsed exhausted onto the bed next to Sinderella, who herself could barely move. His cock remained in her ass.
“My goodness,” he gasped, “That was the most tremendous fuck of my life. You are a truly remarkable woman! May I learn your name?”
“My name? Why yes, it’s….”
But Sinderella was interrupted by the chimes of a clock that echoed through the Hall. Looking up she saw with horror that the clock was about to strike midnight.
“I’m sorry your Highness, I have to leave.” And with that Sinderella rolled off the Prince’s cock and ran from the bed, cum dribbling out of her dilated asshole. She made it out of the castle just as the final chimes rang out, just in time to see her horse and carriage turn back into a puddle of cum. She felt the cool night breeze on her face as her mask vanished. Slowly she started to make her way back to the house.
The next day there was a great commotion throughout the land. Everyone spoke of the mysterious woman who had successfully taken the Prince up her ass. Sinderella came downstairs slowly, tired from walking back from the palace, and with an ass that was still a little sore. Her stepsisters were arguing.
“It could have been me!” pouted Tegan.”I was just about warmed up when that slut made him waste his cum on her!”
“Oh really? You could barely take that courtier in your pussy!’ said Greneril. “I on the other hand was almost gaping.”
“Both of you can keep quiet,” said Sinderella’ stepmother curtly. “You’ve wasted the chance to marry the Prince. And you,” she said as she saw Sinderella enter, “How did you get out of the cellar? And why are you in such a state?”
Before Sinderella could answer, a trumpet blew outside, announcing a Royal Messenger. All the villagers went out to listen.
The messenger explained that the Prince was searching the Kingdom for the mysterious woman whom he had fucked in the ass. The only clue to her identity was the glass dildo. Whoever managed to take the dildo up her ass would be asked to marry the Prince.
There was a commotion as all the gathered women lined up to take their turn with the mighty glass dildo. Tegan and Greneril were first to try, but try as they might there was no way that their tight assholes would take such a thing. All the other women then tried and failed in turn, each one reluctantly handed back the dildo to be cleaned and lubricated with oil for the next attempt.
“Is there no-one else?” the Messenger asked after the line emptied.
From the back of the crowd Sinderella raised her hand.
“I haven’t tried yet” she said.
She moved forward but her stepmother grabbed her by the arm.
“How dare you even suggest that you could fuck the Prince! Get back inside!” her stepmother commanded.
“Wait!” said a powerful voice from the Royal party. A man wearing a hood stepped through the crowd and removed his cloak. It was the Prince!
“I think she should be allowed to try.” he said. “Does anyone object?”
Sinderella’s stepmother lowered her head and said nothing.
Sinderella took the glass dildo in her hand and covered it generously with oil. She knelt on the ground, lifted the back of her dress and leaned forward, pushing the tip of the dildo against her asshole. Taking a deep breath she bore down against the dildo and after a moment her ass opened and swallowed the mighty glass cock. In it sank until soon its whole length was inside her. The Prince stared in surprise and delight. He knelt down to face her.
“Fair maiden, last night you took not only my cum but my heart too. Will you marry me?”
Sinderella paused. “Yes, but…”
“What is the matter?” the Prince asked.
“Well, your highness, I would like to accept your proposal, but I am worried. For you see, I am a tremendous whore and despite your magnificent cock ….”
“My darling,” the Prince said, “I will ensure that you have as much cock as you need. None of your holes need ever be empty again. And fortunately I like to watch.”
“In that case, I accept!” said Sinderella as she embraced the Prince.
They were married soon after, and before long there was satisfaction throughout the land. After his encounter with the Fairy Godmother, Tom discovered how much he like to fuck older women and was very popular at the local nunnery. Sinderella’s stepsisters found husbands to satisfy them, although Greneril later realised she was bi- and got pussy on the side. Even Sinderella’s stepmother was fuck-buddies with the blacksmith (and his son).
As for Sinderella, her needs were truly satisfied. She was regularly gang-banged, with the men either spraying their cum over her face and tits or dumping it in her holes. The Prince would watch, and once the other men had had their way with her he would finish her off in the ass. She never wanted for cock again.
And they all lived happily ever after.