tagBDSMCassandra the Wicked

Cassandra the Wicked


Part I

Princess Cassandra Orsini smiled wickedly at Dina, as Dina was repeatedly whipped. Not permitted to punish Cassandra physically the school master had to resort to whipping Dina.

Cephalonia was a Kingdom with fairly uncommon rules for their monarchy, the crown was passed down through the female lineage. This made room for ambitious men to take the throne. The King himself was once an ambitions wealthy merchant that bought the throne. The heir to the thrown would be whomever married his only daughter Cassandra. The spent his time making Cassandra the most suitable type of bride. Cassandra was always beautiful but she lacked discipline in her studies, and would rather mingle with the aristocracy than study.

Cassandra loved the fact that everyone practically had to worship the ground she walked on. She would make members of the aristocracy do humiliating things simply for her pleasure. Once an aristocrat that lived in the palace spilled some wine on Cassandra's dress, she made him clean out the pig sties naked and made many of her aristocratic friends watch forcing them to laugh.

It had been five years that Dina had been whipped mercilessly almost every week. It had never gotten easier. Her knees pressed up against the marble floor of the grand palace of Cephalonia. She was completely naked, her hands properly folded behind her own head. She let out sniffles and whimpers as members of the aristocracy strode by scoffing at her predicament. Cassandra might do the same to the members of the aristocracy if they didn't approve of everything Cassandra did. All the while Cassandra smirked wickedly. She enjoyed this spectacle.

It was after all that God had personally chosen that Orsini family to rule their tiny kingdom of Cephalonia. It would be sacrilegious to even lay a finger on someone as divine as Cassandra Orsini. Dina was chosen from the peasantry, out of hundreds of applicants Dina was considered the most lovely and compatible for Cassandra. The peasantry lived in squalor for the most part, any money they did make was taken from them to pay for the Royal Family's(mostly Cassandra's excess) It was the hope of the Orsini family that their wayward daughter would form a bond with Dina, and although Cassandra herself could never be harmed she would behave because her behavior would lead to the kind and gentle Dina to be punished. Unfortunately Dina rivaled Cassandra in beauty and this threatened Cassandra.

Dina had the title of whipping girl, she was humiliated regularly at the hands of Cassandra Orsini. She was allowed to mingle with the aristocracy, but she constantly serving brutal punishments for the sins of Princess Casandra. Although Princess Casandra sometimes feigned sympathy for Dina she secretly enjoyed inflicting pain indirectly on Dina. Cassandra was the heir to the throne and she was going to make an awful Queen, cruel in every way Cassandra delighted in watching others suffer. Cassandra would purposefully do cruel and unwarranted acts towards her teachers in order to watch Dina get punished. Dina once was punished severely because Cassandra destroyed a copy of one of Plato's dialogues, the man assigned to teach Cassandra was understandably upset as it was the last remaining copy of that dialogue, the teacher was in the process of copying it by hand(the only method of the time) it is said to have held the secrets of Atlantis.

Cassandra was a brat that absolutely despised learning classical education, a type of education rarely given in the tail end of the European dark ages. Although Cassandra was given beauty by god, she was not given a good moral predisposition, perverted and sadistic to a fault Cassandra cared for no one but herself. She regularly was absent from scheduled meetings with her teacher, participating in decadence not even imagined by the peasantry. Even now at 24 years old Cassandra's aging father required her to attend classes on etiquette and classic philosophy and history. Dina was at the service of the royal family for five years, and today was her final day of service. Cassandra did everything she could just to see one last glimpse of Dina's naked backside being whipped.

Now as Dina was sobbing facing the corner, the philosophy teacher absent Cassandra approached her.

"So this is the last day I get to use you, you little harlot. You know your lucky your leaving alive, I could have done something so bad it could have gotten you hung. Then daddy wouldn't have to pay you, I could use the money for crushed Rhino horn, it is suppose to make your skin very smooth."

"Thank you Princess Cassandra Orsini." Dina responded as authentically as she could

"I can still just ask my father to take you to the gallows, he'd do it he would have you killed for no reason at all just if I asked. You owe me one Dina."

"What do you want me to do?" Dina replied, she had been in this situation before.

"Lets go to my chamber I'll tell you there."

Dina followed Cassandra into her large bedroom. It was Dina's last day in the palace and she knew this was coming. Cassandra loved to be pleasured by Dina for the last few years Cassandra had been rejecting suitors left and right and although she felt as though she was too good for almost every man, she did have her own needs. She loved to have her pussy licked by Dina. Dina did not like it so much.

Dina's face was buried into Cassandra's most vagina, Cassandra's hands pushing Dina's face into her pussy. Dina lying on her stomach kicked her bare feet against the soft bed as her lips were pressed so hard against Cassandra's vagina that her teeth cut into her lips. Cassandra didn't care about the painful sounds Dina made. Cassandra held a ridding crop and would whip Dina's already tender and scared backside if she tried to pull her head up for air.

"Put your tongue into it!" Cassandra barked

Barely breathing through her nose Dina furiously worked her tongue around Cassandra's clitoris. The only way to be released from Cassandra's grasp was to give her an orgasm.

Cassandra kicked her feet wildly while repeatedly spanking Dina in the buttocks with her riding crop, Dina wondered what the Eunuch guards thought when they heard the Princess squeal, when they heard the loud slaps of the riding crop on Dina's ass.

Rumor has it that Cassandra had requested to personally view the castration of the latest Eunuch guards who were slaves captured from the last campaign against the island of Malta. After Cassandra watched the castration it is said that she immediately convinced Dina against her life that she pleasure her in bed, it is said that she made the Eunuch watch, making sure that the job was done right. No man could look at that sight without getting aroused. Cassandra was the most feared member of the Royal family, no one crossed Cassandra.

Breathing heavily with vaginal juices smeared all around her mouth Cassandra tied Dina into a hogtie position. Dina lying on her stomach had her arms tied behind her back and her feet tied to her arms. Not even given time to wipe Cassandra's now stinging vaginal juices from her face, she was forced to go to sleep in this position. Dina always slept while immobilized and on the floor next to Cassandra's bed. Cassandra once woke up to Dina trying to masturbate quietly and for the last five years has made it a priority that Dina would never again receive sexual pleasure of her own.

When Dina was woken up and untied by a Eunuch then led out of Cassandra's room this was the way she woke up everyday, except today she had a smile on her face, it was her last day as a whipping girl. She was to receive payment for all of her years at the palace and she was to be free. She was promised enough money to purchase property, possibly now she could move on with her life and marry a nice man and start a family, she could leave all the torture and cruelty of the palace behind her.

"Ah beautiful Dina, I am so grateful for your service, you have sacrificed your backside for the good of my daughter." the King spoke.

"It is true I am glad this day is finally here." Dina replied

"Such a sweat lady you are, despite everything. I hope you know you really helped Cassandra out, she doesn't speak outwardly about your contributions but believe me, you have been a friend to Cassandra." The King refused to see his own daughters cruelty.

"You are free to go my dear, I regret to inform you that we cannot afford your full pay and unfortunately we will be unable to pay you anything, the Royal coffers are dry I am afraid."

Dina was building with rage, she wanted to kill the King for a moment. She knew of at least three feasts scheduled in the next month simple to wow some of Cassandra's suitors. It was outrageous all of these years she had waited for this day, her only solace was her promised pay, and now that was gone too. Dina began to sob uncontrollably, as tears streamed down her face two guards dragged her off and took her outside of the palace walls. Dina was wearing rags, she did not even have shoes on her feet. She looked into the squalor of the main village as the guards abandoned her. There was only one hope left.

Part II

Before Dina was taken to the palace as a whipping girl, she had a love. After leaving the orphanage she grew up in she met a young seaman named Marcus Chatzi and had a whirlwind love affair. He had left to sea and never returned, desperate Dina agree to become the Palace's new whipping girl in order to survive. If she could do it all over again, she would have died waiting for Marcus. If Marcus had indeed survived he may be able to rescue Dina from her predicament.

Dina fondly remembered Marcus and her mind wandered to the sex they used to have, Dina not being allowed to orgasm for five years, had a unstoppable desire to find a safe place to remember her old flame and play with herself.

Dina scanned dark alleys, but the streets were so crowded. Finally she found a shack that looked unoccupied at the moment, in Dina's sexually deranged mind sneaking in and spending five minutes to pleasure herself was worth the risk of being caught. Lying down on the straw bed was the greatest comfort she had felt in five years, she imagined Marcus.

Marcus had just come back from a successful voyage across the Mediterranean to North Africa, he had come back with plundered treasure from the ruins of Egypt and the two 18 year old's had a brief moment of stability. She remembered dropping to her knees and sucking down on his penis shaft, all the way to the pubic bone, all while staring directly into Marcus's rugged eyes. Marcus completely clothed in his sailor's outfit, with only his pants half down, Dina completely naked with not a stitch of clothing. Dina loved feeling like a whore while she sucked off Marcus. Marcus would notice Dina's right hand playing with her clitoris and he would instruct Dina to put her hands behind her back while she sucked him off. This just built up the tension more for Dina.

Eventually Marcus would instruct Dina into a prone position, with her head down, and her ass up high. On their earnings the two could not afford a child, so Marcus would usually not grace Dina's vagina with the presence of his large cock, instead he would spit and finger Dina's asshole with two fingers. When Dina first tried this she thought it too painful, but now she was masturbating vigorously to the thought of having anal sex with her old flame.

Dina couldn't help it she would rhythmically sway her ass into Marcus's penis. Marcus eventually would hold Dina's arms behind her back preventing Dina from touching her badly neglected clit. Dina would beg to turned over. It was at this point in the recollection that Dina could feel an orgasm coming. Here she was in an abandoned shack that some random pauper masturbating furiously.

When turned over Marcus would place his erect penis near Dina's mouth, it was at this time that he started playing with her clit at a very slow pace, as she furiously sucked on his large member. Eventually she would take over masturbating herself furiously while sucking on Marcus's dick. She did this until she could no longer take it. Just as she was having an orgasm Marcus would pull out his dick and cum directly over her face, not sparing her eyes or nostrils. As Dina remembered the warm semen falling on her face she had an orgasm right there in the middle of the seemingly abandoned shack. Desperate loud animal like noises came out of her mouth.

"Are you alright young lady." the voice of a desperate old man startled Dina, her orgasm still subsiding, she also felt panic and humiliation.

Dina streaked out of the dwelling with absolutely no garments on her back, as she ran through a shocked and sometimes laughing crowd. Her breasts covered by her arms, her whipped back exposed, her scared butt giggling for the onlookers.

If the church officials found her she would be tried and hung due to indecency, she desperately scanned her mind for a friendly sanctuary she remembered a tavern she and Marcus used to visit when they had money, possibly the owner would recognize her and give her mercy.

Part III

The tavern goers were shocked when they saw a naked woman burst through the door immediately pleading for help. Dina didn't know what to do other than get down on her knees and beg the slightly familiar looking tavern owner for help. Dina knew she looked so pathetic on her knees in front of so many burly and drunk men begging and crying, her medium length black hair in disarrayed her medium sized naked breasts heaving.

After the initial shock the tavern owner looked at his customers and told them "Halt this is a friend of Marcus we must get her a room."

Dina was whisked away to an upstairs bedroom, not just any bedroom but the master bedroom.

"I'll sleep in the cellar tonight mam' Marcus has been looking for you, he will be happy that God sent you here."

"What do you mean?"

"You are Dina am I not correct."

"Yes that is why I came here, I knew this place five years ago, it is the only place I knew to go."

"Well Marcus is a very rich man now and he still fancy's you, he has been looking for you for the last three years, he had all but given up hope, I know not when he will get back, he is doing business in Omala at the moment."

Dina was overjoyed

"He wants me, he really has been looking for me for all this time."

"Yes my dear is never stopped, he does love you so."

For the next few days Dina day dreamed and masturbated to the thought of Marcus returning. She slept well on a soft bed and ate find foods the tavern keeper brought for her. She nervously wondered what Marcus would think about the permanent wounds on her back and buttocks. She couldn't believe her luck. Anger swelled up inside, when she thought about the cruelty in the palace, and the lost years away from Marcus. She felt guilt for leaving Marcus in the first place.

Then one day she saw him in the flesh. Dina was just waking up, with nothing but a white sheet covering her naked body she saw Marcus, he looked much different.

Marcus used to be so rugged, now he was clean shaven, wearing the finest of merchant clothing, with a colorful hat complete with an expensive plume darting out of it. There were no words either could say, they just both embraced each other in a long kiss, which eventually led to sex.

Marcus didn't waste any time he pulled down his trousers just enough to expose his erect penis, and he climbed on top of Dina dangling his penis in front of Dina's mouth, Dina began to suck while laying on her back, eventually Dina couldn't help it she started fingering herself while doing this. Marcus grabbed her hands and pinned them down over Dina's head and began to thrust his penis into Dina's mouth. It was no longer a blow job, it was now a face fucking.

Dina's lower body squirmed as Marcus fucked her face with his Penis. Dina could barely breath, finally Marcus pulled his penis out of Dina's mouth and Dina muttered the words "I love you."

"I love you too" Marcus responded then he continued fucking Dina's face relentlessly.

Dina was worried Marcus might blow his load right then and there, but he had never had an orgasm before she had, she felt his penis bulging in her mouth. She would forgive him this one time if he ejaculated before she was spent, it had been three years.

Suddenly Dina found herself on her stomach, she spread her own ass cheeks open for Marcus to insert his penis. Marcus paused.

"What on earth happened to you?"

Mortified Dina remembered her scars, "Oh I am sorry Marcus."

"Do not apologize."

As erect as ever Marcus speared into Dina's anus, the pain was almost unbearable, it had been five years Dina screamed and her toes curled she kicked her feet as Marcus trusted into her anus.

As painful as the experience was it was also comforting, and amazingly arousing. Marcus allowed Dina to rub her clitoris with her fingers. Marcus grabbed a clump of Dina's hair and pulled it back, Dina was faced with a small hand mirror that Marcus had propped up on her head stand while she wasn't looking. Dina saw her pressured and sexually overwhelmed face. Minutes passed Marcus kept up a steady thrust. Soon Dina was starring directly into her own face while she was experiencing an orgasm. When it was all said and done Dina practically passed out, she became completely immobile laying face down with her legs spread and semen dripping from her ass. She was glad Marcus was back.

The two lovers eventually got around to talking. Dina was in a considerable amount of pain from the anal sex, which simply served as a reminder of the dirty sex she had just had with Marcus making her practically permanently aroused, during conversation it was hard for her not to touch herself.

Dina asked for forgiveness for leaving to the palace, Marcus held no ill will towards her. When Marcus heard of the treatment that Dina received at the hands of Cassandra he was appalled.

"You know the peasants call her Cassandra the Wicked, they blame her for the high taxes, the Royal family's excess has put the economy in dire straights, the Royal family will be over thrown if they are not careful, the King has put all the burden of his own families excess onto he poor peasants of this Kingdom and they won't stand for it. The taxes are oppressive"

"I hope they are overthrown, I have no idea how they can claim they were appointed by God to rule." Dina replied

"You see I have this already covered, the King needs money in his coffers and he is soon to die. I have plundered the ancient ruins of Minoa and melted down so much gold I have more wealth than three Kings."

"Continue, continue" Dina said excitedly, Marcus smiled wickedly and continued.

"You see I am invited to a lavish feast, the monarchy in Cephalonia is passed down through the females, this is why Cassandra is so important to the King, as his only daughter, he needs an ambitious ruler to take the thrown, and save his own life from a peasant revolt."

"So the King wants you to marry Cassandra?" Dina replied confused.

"Oh yes he has practically begged me, he even made Cassandra take off her clothing and spin in a circle to show me "what I was getting""

"Were you impressed?" Dina questioned

"She is a beauty but has a very wide buttocks and she has such a bad attitude, she was so embarrassed to expose herself to me. She pouted relentlessly when he father asked her to do it, but finally gave in when he reminded her how much wealth I had. Now that I hear about her absolute wickedness to you I see little reason to bail her family out of this pickle. I shall refuse the invite to the feast they have prepared for me."

"Oh Marcus don't you see now is your chance to get revenge for me, to get revenge for the whole peasantry that has suffered under this incompetent and decadent family for far too long. They are desperate, you must strike." Dina said with a wickedness seldom heard.

Report Story

bystrangenickle© 2 comments/ 37595 views/ 10 favorites

Share the love

Report a Bug

2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: