Teacher’s Dilemma

Author’s Note: Please read this series sequentially to get a better understanding. This story is eventually going to take a dark path and will not follow any traditional non-con templates that most stories do. If you’re expecting a traditional non-con story through and through, it will disappoint you at some point. If you want better character development and unexpected plot twists, you’ll be in for a treat. If you choose to follow this series and still get offended, I gave you a fair warning. That being said, let’s continue.

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Devin Williams (42) is twice the age of his brother Tyrone. Tyrone was born late and was an unexpected birth. When Tyrone was born, Devin was already serving in the US army. Devin is opposite to his brother, muscular and can outmatch anyone in close combat. He is black belt in Brazilian Jujutsu, Taekwondo and Muay Thai. At 6’5″ he looks like Michael Jai White at his peak.

With his ability to kill, moved him to special ops team. In his career with the army, he went on many off-the-book operations. After one botched up operation, he took time off and returned home. He did some therapy sessions to get help with his PTSD. During this time, their parents had a car crash, in which both died. To help his brother, who was at the time about graduating from high school, he took early retirement from army. He did not know that he’ll soon be creating the most notorious criminal enterprise with the help of his friends from the special ops team.

When Devin reached out to his closest four friends from the team, who were all part of that last mission, they all agreed to be part of his plan. His essential plan was too ambitious, but all of them wanted to screw over the people who put the lives of excellent soldiers in unnecessary danger just for their own political career. They have reached too far from where they started in a short amount of time. But it was still not over. An extremely ambitious plan is ahead.

When Ty moved full time in their gang and started working on his high-tech gadgets, Devin’s plan escalated much faster. Now he had 24×7 surveillance on several high-profile people, including cops, feds, marshals, senators and even some judges. He took inspiration from John Edgar Hoover, first director of the FBI. Know everything about everyone in power if you want to keep doing what you want.

Ben Lewinsky (39) was famous for his exceptional usage of knifes and daggers in special ops. He usually prefers knifes over guns, if possible. At 5’10” he is the smallest of the bunch, but fitness has always been on par with everyone else. During a mission in Serbia, he carried an injured soldier on his back and ran over 6 miles non-stop and saved his life. “Serbian winters are brutal,” he would always joke when recounting that event.

James “Jimmy” Parker (37), youngest among the group, was the sharpshooter (sniper) for the special ops team. Ben was also a spotter for Jimmy for most of the missions when only a small team would be ideal for the mission. At 6’1″, Jimmy was a gymnast before he went to serve in the army, which meant lean muscles. Jimmy is exceptionally good with all kinds of guns. He has massive respect for Devin. Apart from the team, nobody could stand Jimmy because of his clinical diagnosis of a psychopath. He had zero emotions and cared for no one.

Daryl Jackson (44) was another gunman on the team. His precision with rifles and handguns is impeccable. At 6’3″ he’s also equally muscular as Devin. He was the only other black member of the closest members of this team. Darryl always wanted to become a professional boxer and is exceptionally good at it. After graduating from high school, when he didn’t find a way into it, he moved on to serve in the army.

Mikhail “Mike” Markov (41) was an expert in explosives and backup sniper for the team. Mike’s parents were Russian immigrants. His dream was to play in NBA one day, but his parents were never supportive of his dream. Eventually he moved on to serve in the army initially out of anger, but then started enjoying it there. There was no pressure from his parents, and he could live his life exactly the way he wanted. At 6’7″, he is the tallest among the group and muscular as well.

Devin walked out of one room of his mansion to the living room, where everyone was waiting for him. Dressed in custom designed, expensive luxury dark blue three-piece suit, along with a white shirt and black tie. You cannot find Devin anytime and not be impressed with the choice of his dresses. He is always conscious about what he’s wearing.

Turning towards his brother, he calmly said, “We’re all meeting your slave for the first time, and I hope you can justify the investments made on her, Ty.”

Ty instantly replied, “First, I don’t have to justify anything to anyone. I have used all my personal funds only. Second, I’m throwing a party for all of you guys that doesn’t mean that I must impress any of you.” he was always salty at his brother since they forced him to work full time for the gang.

Devin wouldn’t take it in front of his friends, so he walked over and sat next to Ty on the couch. Placing his arms around Ty’s neck, and said sternly, “I’m glad you remember my words about never to be afraid of anyone. But now I’ll give you another advice which you should keep deep in your head. There’s a thin line between being brave and stupid. Choose your words carefully when around me.” With that, he got up and said calmly, “Let’s go.”

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LAST NIGHT

Jessica walked out of shower completely naked and followed her usual daily moisturizing routine. She already felt too numb to everything that her master has done to her. What does he expect her to do during this New Year’s party? She was sure they would degrade her if it were possible now. Her thoughts instantly went to the last party they hosted at her own house. Jessica somehow felt like this one would be even worse.

She walked out stark naked, trying to find her mistress. Her idea was to convince her mistress to save her from this party. In the past few days, Jessica had felt that Rose was softer on her than Tyrone. If there was any hope, it was Rose. She thought to herself, “If there’s even a slight chance of not to take part in this party, I have to try it. Why am I getting so comfortable walking completely naked inside this mansion?”

Then she saw her mistress sitting on a chair and completely immersed in her phone. Jessica walked up to her and kneeled. She, as in her usual routine, like a pet picked up her right foot and passionately kissed her sole. Repeating same again to the other foot.

Rose looked down at her and instantly understood that her slave wanted something from her. She said, “What do you want, slave?”

“Mistress, your humble slave has a request for her generous owner. If my mistress considers her unworthy whore slave dedicated enough, may she grant her one wish?”

“Depends on your wish, whore. Tell me what you want?”

“Mistress, please grant your whore exemption from this upcoming party. This slave will do anything her mistress demands from her in return.”

“I can’t do that, slave. Your master has already organized the party and guests are expecting greatest show from a whore.”

Rose saw a dejected look on Jessica’s face. She was sad, but didn’t dare to counter the argument. It was then an evil idea came to her head. Rose continued, “What I can convince your master on is to grant you a chance to earn the exemption. But this chance will cost you heavy. Are you willing to take this chance?”

“Yes, mistress, your whore will take any chance her generous mistress will offer to her. And she will pay any cost associated with that chance.”

“Okay then, stay kneeling here. I’ll be back after convincing your master. Do not move until I give you the permission.”

Rose went out and explained her plan to Ty. He was initially unsure of why to take this unnecessary risk, but when explained further, he also got excited. “I am impressed with the bitch you can become sometimes. It’s a great idea let’s do it,” said Ty.

Soon Rose was back in a black professional suit. She even gave her proper conservative bra and panties that she had forgotten about for a long while. Jessica dressed and looked at herself in the mirror and looked excessively professional in whatever she was going to do.

They walked out to the main living room where everyone was sitting comfortably, which included Tyrone, Reggie, Rick, Jamie and soon joined by Rose. Next to her standing was Anna, the Asian girl, dressed exactly like her. Not knowing what’s going to happen, she waited for Rose to explain.

Rose said, “Since you asked for a chance whore, we’ll grant you one. Here you and Anna both will compete against each other. Whoever wins will join the party as a mistress and other will be the solo slave for the entire weekend. How do you win? Well, whoever will break the rules first will get the loss. So, for you to win, force other to break any rule.”

Anna remembered few minutes earlier when Rose gave her the dress for this challenge she said to her, “You remember about that worst nightmare you begged me not to make a reality? Well, if you didn’t win this challenge, I’ll force you to live that nightmare every second of your living days.” With that, she left like it was the most normal thing to say to anybody.

Anna knew she cannot lose this challenge. Jessica can handle the party, but she cannot afford to live her nightmare. She swore to herself, “I will win it at any cost.”

Rose had a lottery bowl in her hands with a bunch of slips in it. She called first Jessica towards her and ordered her to pick one. Later, Anna also picked one. Then she continued, “Each slip has a name on it. Open it and read it out loud.”

“Reggie,” said Jessica.

“Jamie,” said Anna.

“Okay, this was the toss. You must give a blowjob to the person you chose without using your hands. We’ll tie your hands behind your back. Whoever drinks the entire cum out of their chosen cock first wins the toss.”

With that, Rick walked up to them, tied both their hands behind their back tightly with a soft silk cloth. Rose shouted exited, “Three, two, one and go.” Jessica saw Anna running towards Jamie and then she looked confused towards her mistress like asking her from eyes only, “Why are these guys not removing their clothes?” When she saw Anna using her teeth to bring the zip of the jeans down, she realized this was part of the task. Looking back at Rose, she realized she was wasting all precious time while Anna was already ahead of her.

Jessica rushed towards Reggie. It looks easy to remove jeans from your teeth, but it’s not. Jessica realized it the hard way. She tried her best but could not even get the zip down. Panic struck her when she heard the bobbling sounds and saw from her peripheral vision that Jamie’s jeans were down along with his underwear and Anna was sucking his cock as if her life depends on it.

After a few more minutes, when she barely could bring the zip down using her teeth, she heard something that crushed all her hopes. Jamie yelped, “Oh my fucking god! I’ve never had a blowjob like this in my entire life. Oh! Fuck. Man, she can suck my soul of out of my cock.”

She looked towards her and saw that Anna had taken his entire giant cock in her throat, nose dug deep in his pubes, and she was using her tongue at the same time to tickle his balls. How is she not out of breath yet? She thought to herself. Returning to her task, she started trying to remove the button on his jeans. But this was even more difficult than the zip.

Anna was thankful to her mistresses’ extreme punishments from past two years that her skill set was miles ahead of Jessica. She was expert in breathing from her nose while going up on the cock. This helps her get the bare minimum of oxygen needed to get the task done without passing out and supplies exceptional pleasure to the man she’d be serving. Anna had also learned to use her throat muscles while sucking to fetch the cum out faster.

Still struggling on the button, Jessica heard from Jamie, “Oh fuck me. Here it comes, you whore. Here it comes.” With that, he gave her everything he had deep down in her throat. Anna, using her ability, didn’t waste a single drop and showed what a cum guzzler she is.

“Stop. Now. Anna, clean the cock nice the way you know you should,” said Rose and then looked at Jessica completely disappointed, “You are a fucking stupid dumb whore. I thought you wouldn’t be able to win the toss, but you wouldn’t even compete with her is just disappointing. That alone is punishment worthy. On each level, I was going to allow a toss, but now your lack of ambition and desire to please your master, you lost all the tosses.”

Jessica felt like someone has punched her hard in her gut. She felt disappointed in herself. Then she heard Rose, “Stand up and get back to the center of the room. Now as your punishment, throughout this challenge, Anna will have all advantages possible.”

Rose looked directly into Jessica’s eyes and said, “Level 1–Anna will get five minutes to finger your whore cunt, and if she makes you cum, you lost the whole challenge. If you can control for five minutes, then you get the same chance. Rules–not a single article of clothes can be removed and while getting fingered, your hands need to be by your side at all times.”

Anna stood right in front of Jessica and realized the difference in their heights. Anna, at 5’2″ is much smaller to the 5’11” frame of Jessica. Anna Lang (28) works for a giant national bank as a mortgage advisor. She wanted to be a hair stylist and had multiple professional trainings as well. But her parents wouldn’t allow such a profession for their daughter, hence the bank.

She got married to her boyfriend from college days last year. The task she had to do for her mistress, for her permission to allow her wedding, would still send shivers down her spine. Jessica did not know how worse things can get when Rose was in her full-on sadist mode. Anna still dreaded that night when she told Rose about her worst nightmare that she cannot survive. She knows that if she loses this challenge, Rose will make that nightmare a reality and force her to relive it every day.

Rose told Jessica to spread her legs wide and hands by her side for this task. After Anna stood in front of her, Rose again said, “Three, two, one and go.” After getting a go from her mistress, Anna instantly opened top two buttons of Jessica’s professional skirt to gain access to her cunt. Soon she placed her right hand inside her panty and inserted two fingers. Within next thirty seconds Jessica realized Anna’s expertise. She was hitting every sensitive part of her cunt with each thrust.

To make matters even worse, her thumb was easily rubbing her clit with this new piercing she’s got. She had clenched her fists tightly and was already struggling to control herself. In, next two minutes Jessica’s legs were shaking, and things were getting much difficult now. Then the worse happened. Anna increased the intensity and speed of her fingering by multiple folds. In the silent room, wet slapping sounds filled completely.

Jessica’s face completely flushed now; she had squinted her eyes, trying to focus on not to explode this giant orgasm. Everyone can clearly see Jessica’s struggle. It was extremely erotic, but no one wanted her to lose the battle just yet. Rose exclaimed, “One more minute to go.”

Anna somehow further increased the intensity, like she was hell bent to make her cum. She didn’t want to take the risk at all. Jessica looked down directly into Anna’s eyes pleadingly, like asking her for some mercy. Jessica only saw intense determination in her eyes. She thought to herself, “Why does it look like she has more at stake here? She’s working so hard as if her life depends on wining this challenge.”

To remain in the challenge, Jessica increased her breathing. When they heard thirty seconds left, Anna brought her second hand and started putting pressure on her cervix while continuing her vigorously fingering. How can she know what to do to cause extreme pleasure every time? Jessica thought it’s no longer possible to hold off for even ten seconds. Tears started flowing from her eyes when she almost gave up when she heard, “Ten. Nine. Eight.”

This brought hope to Jessica that she can win this level. Anna was brutal to her. Jessica felt every inch of her body aroused and alive. Then came to words which she was dying to hear from last five minutes, “Stop. Now.” Anna reluctantly pulled her fingers out. The resolve of Jessica surprised her and disappointed with her own performance. Anna had not lost a single task given by her mistress in a while.

Rose ordered them to reverse the roles, Jessica realized she had no experience pleasing a woman before. She had never been with a woman where she had to please her. Anna clearly is the expert in this matter. It’s a lost battle, she thought to herself. Then she heard those same words again, “Three, two, one and go.”

Jessica followed similar steps and unbuttoned top two buttons of Anna’s skirt and inserted her right hand inside. She was extremely disappointed to find that they hadn’t pierced Anna. Why didn’t they pierce Anna? Why did they only pierce her? Now is not the time. Focus on the task. She inserted two fingers and tried to find her clit. It was exceedingly difficult since she couldn’t see her cunt. Jessica realized she hadn’t made Anna fully aroused yet when she heard from Rose, “Two minutes to go.”

“I’m terrible at this. I don’t even know what I’m doing and what I should do instead,” she thought to herself. The movements of her hand were not as precise as Anna. She tried to copy her by putting some pressure on her cervix. By the time she found the best pressure point, she heard, “Ten. Nine. Eight.”

By the time she removed her hand, it barely aroused Anna. Anna felt much more confident now after finding out that Jessica did not know what she was doing. They both stood again, facing their tormentors, waiting for the next instructions.

Rose continued looking at Jessica. “You disappointed me again. I’m regretting even giving you a chance here. You deserve to be a worthless common street whore and nothing more from the efforts you put,” while this was the exact outcome she was expecting. She knows Jessica had no experience pleasing women and Anna had a vast variety of punishments for pleasing women.

Then she went on the explain the second task, “Level 2–You get to open all buttons of shirt and bra. The receiver will have to always hold the hem of the skirt above her waist to grant full access to other. Provider will remove her panty and stuff it in receiver’s mouth. Then continue to do whatever needed to make your opponent cum. As promised, Anna gets to go first.”

Jessica already felt mortified after listening to the rules of level two. She barely survived five minutes of level one. This time Anna will even get access to her nipples. Somehow, she would know what exactly to do with them to make her cum.

After getting a go from Rose, Anna instantly pulled Jessica’s shirt out of the skirt’s waistband and opened all the buttons in record time. The bra had a convenient clip in front, which she snapped open in less than a second. Access to her nipples was now available. She looked at Jessica and pointed at her skirt. Jessica realized she had to hold the hem of her skirt up. She followed the instructions and in seconds Anna rolled Jessica’s panties out and stuffed it inside her mouth. Jessica closed her mouth shut around the panties and could clearly taste her fluids from the panties.

Anna slapped the inside of Jessica’s thighs, pointing at her to spread the legs again. She followed her unsaid instructions. Jessica now realized that the height difference conveniently brought Anna’s mouth to her nipples. Anna started off where she had left off. Vigorously fingering her cunt while rubbing her clit with the easier access because of her clit ring. Then she brought her mouth to the right nipple and sucked on it hard. While bringing her other hand to play with the left nipple.

Jessica found out that all these piercings were causing much faster and intense pleasure in her. With the skillful fingers and mouth, Anna knew Jessica was much closer to her orgasm than first time. Jessica couldn’t control her moans anymore. This was too much pleasure for her. Then suddenly she felt Anna skillfully using her tongue while sucking on her nipples and perfectly twisted her other nipples, piercing. How does she know to balance pain and pleasure to cause even more pleasure?

Jessica’s grunts echoed throughout the room. Everyone expected her to squirt out any second now. Rose knew differently. Jessica’s mental capability to deny her own orgasm was beyond anything she had seen before. The challenge was, who will win Jessica’s mental control or Anna’s skills?

Anna tired of the efforts she had put already and was confused completely. She should have cum already. How can she hold this? No one can hold this. Jessica’s grunts were getting louder by every second, but she controlled what was uncontrollable for most. She gasped out loud in relief when she heard Rose, “Stop. Now.”

The moment Anna left her, Jessica dropped to her knees, still shivering and trembling. It took her couple of minutes to calm down from what Anna had done to her. She stood up in front of Anna and looked directly into her eyes with anger. She wanted the vengeance now. She wanted to make sure Anna had her orgasm now because otherwise she won’t be able to get through whatever the level three would be. Anna felt the shivers down her spine, realizing she might have overdone. Not knowing what Jessica might do to her now.

Jessica took the panties out of her mouth and threw it at the corner of the room while keeping the eye contact with Anna. Now it was Anna’s turn. She looked pleadingly and apologetically at Jessica. She couldn’t tell her what was at stake for her. She can’t afford to lose this challenge at any cost. This time Jessica didn’t show any sign of weakness. Upon going, she was at par with the speed of Anna to open the shirt buttons and bra clip. In no time, she had stuffed the panties in Anna’s mouth.

This time she had better access to her cunt, but the height difference caused some difficulty sucking on her nipples. What initially saddened her was that Anna didn’t have any piercing or tattoos on her. Why did they only ruin her life permanently and not Anna’s? But now was not the time, so she continued with her task at hand.

Jessica was much more focused this time and felt Anna’s arousal sooner than before. It was when she started sucking, licking, and pinching her nipples that she heard a loud moan. She had now found a weak spot. Anna’s nipples were super sensitive. While increasing the intensity and speed of her fingers, she started putting special focus on her nipples. Anna’s entire body started shaking and shivering because of the extraordinary control she had to put.

Rose now felt more worried. Anna has never been great with her orgasm control compared to Jessica. No matter how much she had punished Anna for unauthorized orgasms, it was not something she could improve upon. The way her body was responding, she knew Anna would cum soon no matter how hard she tries. There were still two-and-a-half minutes left. Only one way she could survive this, cheating.

Rose declared, “Ten. Nine. Eight,” which was clearly incorrect, but there’s no way Jessica would know. Jessica, in her head, thought she never heard the two-minute warning. It’s not possible that five minutes would be over so soon. As Anna’s resolve was about to give up, she heard, “Stop. Now.”

Turning towards her mistress, she looked extremely angry. This was cheating. She somehow knew there’s no way five minutes were over so soon. Even Anna knew her mistress saved her by cheating, but she wouldn’t mind. Jessica could have won this challenge, but now she can’t blame her mistress, which will account for a punishment.

Rose looked into Jessica’s furious eyes and asked, “You look disappointed. You have something to ask?”

“Mistress, your slave was not given the two-minute warning. It felt like five minutes were over much faster compared to before.”

“I clearly gave a two-minute warning and everyone in the room can vouch for that, it’s not my fault that you didn’t hear it. And if I, were you, I’d be careful before blaming the mistress of unfair treatment towards her slaves,” lied Rose.

Jessica knew her mistress was clearly lying, but she cannot make things worse than it must be. She took a couple of deep breaths and tried to calm down and use this newfound information to her advantage on the next level.

After Jessica was much calm, Rose continued, “Level 3–This is the last level, so no time limit. This will be over only after one of you gives up. Rules–You both will do 69 and no hands allowed, only your mouth and tongue. As Anna had won the toss, Jessica will have to be the bottom. Also, grant full access of your cunt to your opponent’s hungry mouth.”

After hearing the rules, Jessica now got the idea of this challenge. They have designed it for her to lose from the get-go. Anna had the ability with her mouth that Jessica doesn’t have, and, on this level, she won’t be able to take advantage of Anna’s super sensitive nipples as well.

Jessica was lying on her back with the skirt pulled all the way up and legs spread wide open. Anna got on top of her with her mouth inches above Jessica’s cunt and she grabbed both her thighs with her hands to make better balance. Once the position was set, Jessica found out another problem. The height difference made it much more difficult for her to have a go at Anna’s cunt. She had to bring her mouth up, bending her neck to an extremely uncomfortable position.

She also grabbed the back of Anna’s thighs to get some level of support, but it still was an uncomfortable position. Anna clearly had the advantage for this level. When they got the go from their mistress, both started using their tongue on other’s cunt. Anna was much more skilled for the task and was soon sucking on Jessica’s easily available pierced clit and alternatively inserting her tongue inside the cunt.

This level was much more difficult than the earlier ones since hands were off-limits. But Anna having better access to her cunt and clit was clearly winning the task. Jessica felt her neck was hurting now because of the position she was in. Suddenly, Anna increased her intensity at eating Jessica’s pussy. She showed her what Rose taught her as “pro-shop” which brought the orgasm to Jessica.

All the arousal from earlier levels and holding on to her, along with the next level of skill from Anna, Jessica lost her inhibitions. Her head dropped, and she was no longer eating at Anna’s pussy. She was now shouting loudly, “Ah! Ah! Ah!” Everyone now knew the inevitable was here. Jessica has now accepted her defeat. And with that, the floodgates were now open. Her ejaculation was giant and sprayed all over Anna’s face. Still going on and on, Jessica’s screams echoed across the room.

Few minutes later, Anna got up and stood next to Jessica, who was lying on her back with trembles still not over from the massive orgasm. A piercing cry from Jessica filled the entire room. Her defeat made it clear what she had to do.

Rose walked to her and while standing next to her she said, “You lost your only chance. Which means you’re the only slave for the entire weekend. You’ll even address Anna as mistress and follow her orders as you will for everyone else.”

Her entire life falling apart with no plan to escape. Jessica kept crying for more than an hour. She needed it to get things out of her system. Tired and exhausted from all the crying, she slept on the floor of the living room.

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NEW YEAR’S EVE–FRIDAY

Anna gave Jessica an enema and cleaned her asshole for the upcoming party, as ordered by Rose. She prepared Jessica as if she was a professional porn star. Anna also applied a special hydrating cream generously across her body. This cream, once dry, gives a long-term glistening shine to the body. All her tattoos were looking even more exotic now with this shine.

Once she completed all the preparations, Anna looked into Jessica’s eyes and realized something was off. She had a blank expression on her face. Nothing mattered anymore for her. Her look scared Anna. She somehow felt this was because of what she did to her last night. Guilt-ridden, Anna kneeled in front of her while holding her earlobes as if apologizing for what she had to do. Nothing changed in her expressions like she had lost completely. Completely scared, Anna left the bathroom in search of her mistress.

Anna told everything to her mistress and her fear that they might have broken her beyond repair. If what she heard was true, this scared Rose as well. Ty will not forgive her this time. She rushed in and saw Jessica. She was looking awful. Eyes swollen from all the crying and a look of deep trauma in her face. She tried giving her few orders, which Jessica followed but like a robot.

“Oh, my god! Have I broken her?” thought Rose.

Rose left her alone for a while, not sure what she should do next. She called Ty and update him on this before he brings the entire crew to the mansion.

“Yes, what happened that you had to call me? All going good there?” asked Ty over the phone.

“No. Something happened to Jessica. She’s behaving like a robot. I’m scared now. Did we break her completely? I never wanted this to happen.”

“Stop.” taking a deep breath, Ty continued, “Now is not the suitable time. Call her. She’ll be able to help you fix this situation better than me.”

With that, Ty disconnected the call. Devin looked at him sitting next to him in the car with a smirk on his face and asked, “All, okay?”

“Yes. Of course. Just some trivial stuff. She can handle herself.”

But his face gave everything away. Ty had a panic look on his face. This was all about earning his brother’s respect. He wanted to show Devin that he’s good in other stuff as well, apart from the usual nerdy stuff. He hoped Rose could do some magic and fix the situation in next twenty minutes.

On other side desperate Rose called and heard the voice say, “You must be really desperate to call me.”

Cringing from within, Rose said, “Yes. There’s a problem here for which I need your advice urgently.”

“Okay. Then I want you to tell me what happened? In detail. Don’t hide any information if you want honest advice.”

Under desperate situation, Rose explained every detail of the challenge night, hoping for some solution. She knew how important this party was for Ty and didn’t want to be the reason to fuck it up.

Rose was expecting what she heard next. “That’s why you should not use your head in planning things when you do not know about human psychology. You know how blackmail works, right? It’s all about hope. Hope that you can get away somehow. Hope that if you keep doing as demanded eventually, it’ll all be over someday. If you take that hope away, you have nothing to blackmail for. No bargaining chips. And last night you took away her last hope.”

“When you cheated on the rules that you made, she realized there’s no hope. You’re going to do what you want no matter what she does. She eventually realized that what you want is to trap her forever and you’re going to cheat your way to make it happen. That’s why it’s important for a master or mistress to not cheat in their own rules. For slaves, there’s only one reality, rules. If they don’t even have rules left, they lose track of reality. YOU CANNOT CHEAT IN THE RULES THAT YOU MADE.”

Rose knew that she fucked up but didn’t need this lecture, so she interrupted her. “I understand I made a mistake. Don’t rub it on my face, please. Help me fix it for now. This won’t happen again.”

With a deep sigh, she replied, “I need time to think. Give me five minutes. I’ll call you back.”

Rose was now panicking even more. She didn’t want to disappoint Ty, especially on this important occasion. “If she can fix this situation, I’m going to be more careful around her. What the fuck was I thinking? Anna could have handled herself. Why did I break the rule?” thought Rose.

When she got the call few minutes later, she felt more than relieved and answered it.

“Now don’t interrupt and do exactly I say. Make it believable and appear to be empathetic towards her, even if you’re not.”

When Rose returned, Jessica was still the same as she left her, kneeling on the bedroom floor, and looking at the floor, completely lost. Rose dragged a chair and sat in front of her. She lifted her chin and looked directly into her lost eyes. “Slave, I know you’re disappointed by the last night’s loss. But I am proud of you the way you performed and challenged much skilled Anna in tasks you had no experience. I am going to make sure you get the reward for your performance.”

Rose stopped to find some excitement in her eyes when she found none. She continued, “I know you believe that I’ll not grant you your reward, but this is a promise. I will make it happen no matter how I must convince your master. But I will need your help for me to make your case.”

“Put forward your best performance for this New Year’s party. If you can do that, I promise after the party I’ll drop you to your home. No one will contact you back at your home till your vacation is over. You will be exempt from all the rules once you’re back in your home. You can do whatever you want till you’re back in the university.”

Still not getting any excitement from her, Rose shook her and said, “Say something.”

“What’s the point mistress, whatever I say, you’ll punish me.”

“No. I give you exemption from all rules till this discussion. Speak your mind freely.”

“You know it, you cheated on that challenge to make sure Anna wins it. It was not fair. There was no point in that challenge, but another degradation for me. I was never meant to win it, no matter how much tried. I had to give up when I realized it. I was an idiot who came to you expecting a fair chance. There’s no fair chance for me.”

Jessica got the one chance she needed to vent off, and she didn’t waste it. “Anna has no piercings or tattoos but me. I’m a canvas. The day Jason returns, he’ll divorce me. There’s no redeeming quality from this moment for me. Anna is a slave, but at least she can have a normal life as well. I have no normal life. You’re talking about once vacation is over. Do you think I can go back to university like this? I’ll better die than to disgrace myself in front of all the colleagues. I worked my ass off to gain their respect and you all expect me to just give that away. If I’m going to die, then there’s no point in going through with this weekend’s disgrace.”

Rose could now clearly see the anger building up in Jessica’s face. This is good. At least she’s having some emotions back. She replied calmly, “Everything is not over for you, Jessica. Yes, I cheated on that challenge. Honestly, I regret it. I should not have done it. I don’t know what came over me but only reason I cheated was because the sequence was so hot, and I wanted to see the level three. It was the reason I had the challenge. I would have cheated even if I would have seen you losing in that level, but I know that your capacity to control is much higher than Anna’s, so I was confident that you had a fair chance in level three,” lied Rose.

“You’re again lying to cover up. You had already fixed the result. I was the only slave for the weekend. No matter how much I tried, I would lose.”

“I can’t make you believe what my intentions were. But over the time we’ve been together, have you ever seen me not following through with my words? I’ve kept every promise I made to you so far. Last night’s events I’ve already told you I regret, and I promise to you it won’t happen again. No matter the result, I will never break my own rules. I can’t make more definitive promise to you.”

Rose saw some normalcy coming back in Jessica’s face, so she continued, “As far as why Anna has nothing permanent, she’s, my slave. You’re Ty’s slave. He has more say on what happens to you. I promised Anna that I won’t change her body, and I intend to keep that promise. But I can’t make that promise to you. Ty is the primary owner of your body. What I can tell you is that when I made all the drawings for you, Ty made a promise to me. He’ll not expose you to your work colleagues unless you blatantly break any of his fundamental rules.”

“I believe him. He never breaks his promises. Your master has already updated your wardrobe at home again with new clothes. All your new clothes will hide your tattoos. I’ve already told you about the hair extensions to hide your neck tattoo. You must make sure not to break any rules. If you break rules, then I can’t promise any protection.”

Jessica started re-analyzing all the information provided to her. If after this weekend’s task they will let her live her life at least till her vacation time, it would give her some time to think about her own situation. And after her vacation, she can continue her sessions with Rachael. She’ll find a way out from all this mess. If all what Rose has told her just now is true, it’s worth the degradation for the weekend.

She continued, “How would I know if master would even agree to what you’re promising? If he says no, then I’m doing all this for nothing.”

“Trust me on this one. I promise you with my life that I will convince Ty to abide by everything I promised you right now. But I want to know would you give your best performance this weekend?”

“Yes, mistress.”

Relaxed and much happier, Rose said, “Perfect.”

****************************

PARTY TIME

Rose walked into the bedroom where Jessica dressed in the dress provided to her. She was wearing a black formal work suit with a white shirt, no tie and top two buttons undone. This time instead of a formal skirt she was wearing a formal trouser along with her regular six inches locked black high heels. Jessica also had fake glasses with a sexy black frame. Jessica looked like a stereotypical teacher out of a porn movie.

Rose pulled a black flexible metal collar from a bag she was carrying. She placed the collar on Jessica’s neck and placed some pressure on its sides, which made it close a little too tight on the front of her neck. It was open from the back intentionally so that it didn’t hide her tattoo on her nape. The other purpose of the collar was to add the right amount of pressure on her carotid artery, which supplies oxygen to brain. Add too much pressure and she’ll pass out within minutes and too little pressure won’t make any difference. It must be the exact amount of pressure.

Within the next few seconds, Jessica started feeling a little dizzy and, without thinking, said, “Mistress, I don’t feel good. Please take this collar off me. Please.”

Rose calmly said, “Don’t worry, slave, take deep breaths. Everything will be fine. Just breathe.”

Jessica started taking heavy breaths, and in the next couple of minutes, felt better. But then she realized it would be extremely difficult to focus on her breathing throughout her ordeal. They had told her to start the evening with best strip dance of her life. She had a lot of practice, but this would be the first dance she would do for an audience. This collar will make her dancing much difficult.

As Rose left her room, Jessica cracked the door to have a peep into what she was getting herself into. Tyrone had transformed the entire living room into a private strip club. Lots of strangers now seated on their comfortable chairs facing a stage with a pole at the center. They had the lights extremely dim, with disco lights flashing on top of the new stage. She knew that she would have to perform all the routines that she had learned in the past few weeks on this stage for the first time for a real audience.

Few minutes later she heard the song Don’t Cha by The Pussycat Dolls in her room, which was her cue to walk into the living room for her routine. Tyrone’s mansion had inbuilt speakers setup in the walls. He can play the music in every room with a press of a button. Nervously, she walked towards the living room and stood on the stage. This was the time to perform her magic.

The well-practiced inner stripper took over her and before she realized, she was swaying her ass with the rhythm. Her instructor had told her few hours earlier on the phone that she was supposed to throw one item at her audience at the end of each song. But her dance moves had to be perfect to keep the attention.

Within next few seconds, lost in the music, she started her pole routine for the song. Both her legs were wide open, left hand holding the pole, right hand moving across her body, kneading her tits, then sexually moving downwards from her sexy stomach to her cunt. Without even removing any piece of her clothes, she had every cock in the room rock hard by now. She leaned backwards with the support of the pole and started humping the pole with the beats of the song as if fucking some imaginary stud for this audience.

By the time the song was about to end, she felt a lack of oxygen again, which somehow made her extremely aroused by just the dancing. She focused on her breathing again, trying not to pass out. As the song ended, she sexually walked right in front of the pole and unbuttoned the jacket, gently removed it while still moving her ass to the rhythm of the new song, Pour It Up by Rihanna. Once the jacket was completely off, she threw it towards her horny audience and fell on the lap of her master, Tyrone.

Once back to the poll, she started her rehearsed choreography by starting from a kneeling position and sexually getting up while licking the pole like a gorgeous shaft of a cock she needs. For this song she started with showing off her twerking skills, but as the song proceeded, she went advanced with the pole dancing. She was now off the ground and hanging midway on the pole with a wrapped hand and leg around the pole.

She stretched her other leg all the way up and touching her ear and kept it in place with her other hand. Her extreme workouts had improved her stretching beyond her own imagination. While in this position, she was still gyrating her body as if fucking the pole while occasionally licking the pole to make things even sexier. She remained above the ground on that pole and showed some of her skills for the rest of the song. She felt extremely turned on by now and didn’t know why? She had done these routines multiple times when alone, but never had she felt this way before. Was it the lack of oxygen to her brain because of the collar blocking her artery, or was it performing for the real audience for the first time?

As the song finished, she slid down smoothly and walked in front of the pole, continuing her sexy rhythm with the next song, Bad Girlfriend by Theory of a Deadman. By doing some teasing ass movements, off came her special stripper pant in one smooth jerk. She threw it again towards her audience, and this fell on Daryl’s lap. He held it up to his nose and took a deep sniff of it. Her shirt was long enough to hide her sexy and shiny golden micro thong.

Her instructor specifically designed this routine to tease the audience. She did all technical pole dancing maneuvers to titillate the audience to their maximum potential, showing nothing. Even though she was hanging upside down on the pole, she had practiced wrapping both her legs around the pole in such a manner that the shirt would still tuck between her body and the pole. With the beats, she would sexually slide up and down the pole while rubbing her cunt on the pole. This increased her arousal even further.

Everyone was so aroused that they were waiting for the song to be over so she would have to get rid of this evil shirt off her body. The routine went ahead to the next song, another one by The Pussycat Dolls, Buttons. Jessica slid down to her head inches above the ground, then slowly and sexily she flipped to stand up without exposing herself more than necessary.

She again walked to the center of the stage and extremely slowly started unbuttoning her shirt. The catch was that this part of her routine just involved her dancing for them sexily and not on the pole. Every time the song reached to its catchphrase; I’m telling you to loosen up my buttons. She would unbutton one, starting from her sleeves. Her shirt was custom designed to have an exact number of buttons for the song. By the time song reached its end she had all the buttons opened but kept her shirt closed while continuing her sexy dance moves.

This sequence was too erotic for everyone. Tyrone didn’t even know how great of a dancer she had become over the period. Finally, she sexily removed her shirt and threw it over and Jimmy caught it. Everyone cheered and clapped as the shirt went away.

Gracefully, she danced her way back to the rhythm of the next song. I’m a Slave 4 U by Britney Spears. Her entire body had a glistening shine because of the special lotion she had put on herself earlier. Her matching golden lace bra and micro thong did nothing to hide her gorgeous tattoos. This song’s choreography was more technically advanced than overtly sexual. She displayed all her pole dancing skills and her ability to stretch while hanging on the pole upside down with just her one leg.

The skills she owned amazed everyone. As the song transitioned, she smoothly danced her way to the front of the pole, which meant one more item will go off. Next song, Dirty by Christina Aguilera, was playing and Jessica was swaying her ass to the rhythm of the song. With one smooth motion, she opened the knot of her bra from her back. Still holding the cups of the bra on her palms while teasingly continuing to dance. Then slowly she removed her bra as well and threw it and fell right in front of Rose. Everyone cheered again as only one item left on her body, the thong.

This time, she showed her most erotic dancing skills around the pole to the beats of the song. At one point in the song, the pole passed through her cleavage, and she pressed both her tits around the pole. With the beats of the song, she squatted down and up while still swaying her ass. She was titty fucking the pole in a perfect rhythm of the song. This was so erotic that everyone’s cocks were about to burst out of their pants.

The next song in her routine started, My Pony by Ginuwine. She danced her way to her stripping point. Her exotically erotic dance routine continued where she would turn around and grab her ankles without bending her knees and still swaying her ass to the rhythm. She was teasing them to their limits. But as the song was about to end, she slowly started rolling her thong down to the ankles without bending her knees and her ass pointing to the audience.

She turned around and threw her thong directly into Devin’s lap. He smiled and felt genuinely amazed by her performance. He placed her thong inside the pocket of his jacket. Meanwhile, Jessica continued her dancing. She now had her both her legs wide apart, and her finger was spreading her cunt lips for better viewing of the audience. This is when she realized her cunt was soaking wet. By now Jessica was heavily panting and told herself, one more song and that’s it.

As the song was about to transition to the next one, she walked to the corner of the stage and picked the bottle of lube that her instructor had placed there as part of her routine. As she danced her way back to the pole, next song started. The loudest cheers from the crowd echoed through the room as they heard the anthem of every strip club, Pour Some Sugar on Me by Def Leppard.

She continued her erotic dance around the pole and as the song reached its title; she squeezed the bottle of lube and poured a generous amount of lube all over her tits while holding the pole with one hand and leaning backwards. She stood up and got back to the front of the stage. While swaying her ass to the rhythm, she started massaging both her tits in the most erotic way possible. Once she had both her tits completely lubed up, she started paying special attention to her pierced nipples. She started her practiced sexy walk while twisting both devil fang piercings on her nipples.

When she reached in front of her audience, as per the plan, she sat on Devin’s lap. The song still playing, she started giving him one of the best lap dances he had ever received. As he started playing with her nipple piercings, she placed both her hands locked behind his head. She started kissing his cheeks and the sexually warm air hitting his ears was teasing him more than he could handle.

It was then he pulled her head and planted a most lustful and passionate kiss on her lips. They both were making out while she was still grinding his cock while songs after songs kept on playing. Both got completely lost in their own lust when Jimmy stood up and said, “Enough of that you guys, lets open her up. I’m done with all her teasing and let’s see what she can offer us with her holes.”

As she stood up from Devin’s lap, Ty walked up to her and whispered in her ears, “You’re not allowed to cum this year if you know what’s better for you. If you’re successful with your task, as a reward you’re free to cum as much as you want on the first day of next year, but if you fail, you won’t be allowed to cum entire next year.”

She looked up at the clock and saw it was 9:50. Would she be able to control for over two hours of fucking? Only time will tell. She was already too much aroused even before they started fucking her.

Soon folks started removing their clothes. Devin, once naked, sat back in his chair. Jessica bent down while keeping her legs completely straight and wide open, pointing her ass for the first cock of the night. Jimmy was the first person to enter his enormous cock all the way in with one smooth thrust inside her soaking wet cunt. Jessica had a loud, surprised moan leave her mouth at the sudden invasion, but she continued with licking the massive shaft of Devin’s cock.

Jimmy increased his speed and started rubbing her easily accessible clit in rhythm. Jessica was deep throating Devin’s cock with his hand on her back, controlling the tempo. This went on for a long while, and Jessica was trembling to control her massive building orgasm. Jimmy showed no mercy to her, kept on with his assault on her cunt. Jessica thought the only way to survive this would be to make both cum before her.

She used her newer learned skills and started using both her throat and cunt muscles around their shafts. In next few minutes, she realized both will cum soon. They both tried their best, but she was too good for them and first she felt a massive load being deployed deep in her cunt, instantly followed by a load deep in her throat. She wasted nothing and swallowed every drop like a hungry whore.

She looked at the clock and it was only 10:35 by now. She would have to show some extreme level of control for the entire night. As the guys were being replaced, she focused on her breathing to control herself. This time, both guys, Daryl, and Mike, were standing on either side of her. Daryl had her left leg stretched straight up and supported by his shoulder as he pounded her cunt. Mike, on the other end, was much rougher in her throat than Devin. She placed both her hands on his ass to have some balance with this extreme fucking that both were giving her.

Her collar with the text on it, PROFESSOR WHORE, was also causing a lot of problems for her to control her orgasm. The limited amount of oxygen flow to her brain was increasing the intensity of her arousal. She gave them her everything. The best performance she can and both guys also failed to make her cum before they gave up. Her trembling had increased significantly, but she didn’t give up and took two more loads of cum in her holes. One more hour of control left.

They placed a mattress at the stage and next fuck session was going to happen on the stage. Remaining people took their seats, like it’s a live porn action movie. Reggie was on his back and Jessica rode him cowgirl style. Jamie stood next to his head and had his cock deep in her throat. As she was getting into the rhythm, she felt cold liquid on her asshole. Soon as expected, Rick was pounding into her asshole. Completely flabbergasted, Devin was at a loss for words to describe her performance.

All three holes stretched to their limits; Jessica was now struggling to control the orgasm pending for a long time. She tried to remember all the training sessions with Rose and forced her brain to not give up. This combination was hitting all her pleasure points exactly the way she wanted, but she didn’t have the permission to cum yet.

Reggie realized that she’s much better to fuck now with her usage of her cunt muscles. She was supplying immense pleasure to him. Each of her holes was extremely sensitive and alive by now, but she kept her focus and, against all odds, fetched three more loads of cum without allowing her own massive orgasm.

Ty looked at Devin, completely proud of his slave, and said, “What do you think now?”

“You’ve got yourself a goldmine,” replied Devin.

Jessica looked at the clock. She desperately wanted to cum now. She had fifteen more minutes before she had permission. Now Devin was back on the stage and wanted his round two, but this time alone. He wanted to enjoy her with no distractions.

He told Jessica to ride him cowgirl style. She had to do everything, he would not make any effort and she better not stop. Soon Jessica was riding Devin like her life depended on it. He grabbed both her nipple fangs and started pulling and twisting them while she rode him. He then commanded her to rub her clit with all she’s got till he tells her to stop.

She started rubbing her clit while riding his massive cock, and he would not let go of her nipples. This was too much and controlling her orgasm now was crossing her limits. She was about to give up when she heard everyone shout in unison, “Ten. Nine. Eight.”

She realized; she can do it. Few more seconds.

“Three. Two. One. HAPPY NEW YEAR!”

Hearing those magical words, she let go of all her inhibitions and came like never. She would not stop assaulting her own clit and the orgasm would not subside for an awfully long time. Her grunts echoed across the room and the amount of ejaculation shocked Devin as she completely soaked his entire upper body and his face with her cum and more was still coming out.

She shouted incoherent words, “Fuck… Yeah… More… I… More… Want… More… Cocks… In… Me… Fuck… More… Me… More… Fuck… Yeah…”

Not completely recovered, she was hungrier for his cock. She rode back for more. Her cunt was super sensitive and within the next few thrusts, she had an instant orgasm again. Before Devin could cum, she had her third massive orgasm of the year, and it was euphoria for her. It was impossible to control anymore for her and she passed out on top of Devin.

She got back to her senses about fifteen minutes later. If she thought she’s done for the night, it was her mistake. Every man in the room fucked her at least two more times in various positions. She had each cock in her holes in every combination. She stopped the count of how many times she came. Jessica shocked Devin and his friends by the amount of fluids she could squirt out of her cunt.

When no man in the room could have an erection, they left to sleep for a while. Jessica felt like dead meat by now. She never felt this exhausted ever in her life before. Looking up at the clock, it was six in the morning by now. She fell asleep on that wet mattress. Ty scooped his sleeping slave in his arms and took her to his own master bedroom so she can have some proper rest. She did better that he could have ever hoped for.

****************************

The wonderful smell of the steak made Jessica realize she was starving. She opened her eyes to find herself on an enormous bed and to her right, Anna placed a bed tray with food on it. Rubbing her eyes, she tried to search for a wall clock. As she found one, the time on it was 3:30. She sat up after realizing that she had been sleeping for a long time. Jessica mouthed the words, thank you without making a sound. Anna nodded to her and left the room.

Midway through her meal, she heard her master’s voice, “Happy New Year.”

She stopped eating as the instant fear crawled within her being. “Don’t stop. Continue with your meal. I’m just here to wish you a happy new year. And, to tell you, I’m extremely proud of your performance earlier. As I’m a man of my words, you’ve my explicit permission to cum as much as you want today.”

Jessica felt the fear increasing multiple folds now, as she did not know what they have in store for her tonight. After finishing her meal, she took a nice, long bath to wash all her filth. Physical filth is easier to wash, how can she wash all this mental filth? By the time she had finished her lotion and makeup routine, it was already 5:30 PM. Still completely naked; she felt butterflies in her tummy for the unknown to unleash upon her.

Anna walked into the room dressed in the skintight leather latex dress that Jessica was familiar with seeing her mistress in. This dress made her realize Anna will also be her mistress for the night.

“Let’s get you ready for the night slave,” said Anna.

Anna carefully put luxury soft leather cuffs on both her wrists and ankles. The cuffs had stainless steel rings attached to them. All cuffs were black. Jessica could feel the fear creeping inside. She was going to be bound and everybody could do whatever they wish. It’s going to be a tough night for her.

“All your masters and mistresses are pleased from your performance yesterday. As a reward you’re allowed to cum as much as you wish, and you’re allowed to talk as much as you want without requiring any permission. But remember, all other rules still apply. An additional rule for tonight will be to be grateful to your master or mistress each time you cum,” said Anna and commanded her to follow.

Once back in the living room, Jessica couldn’t believe that there was no evidence of last night’s activity. The entire room was clean and had a giant bondage setup right at the center. There were two rings attached to the ceiling with metal chains passing through them. Anna commanded her to stand at the center of everything. She attached both hooks from the chains to the rings on her wrist cuffs.

Anna tied both her hands wide open above her head. Worst happened when someone from behind her pulled those metal chains down and Jessica rose above the ground. Within a few seconds, she was hanging just over a foot above the ground with her hands wide open. She tried to turn her head backwards to find that her master had attached that end of the chain to another ring on the floor. Then she felt both her legs being pulled wide apart. Anna and Rose each tied her legs as well to the rings fixed on the floor.

They tied Jessica spread-eagle, hanging in the air. She couldn’t control herself and said, “Master, your slave’s shoulders are hurting. Can her master be generous enough to tie her on ground? Your slave promises to perform better than last night.”

“Don’t worry, whore, you’ll do simply fine in this position as well. I know your capability better than you know it yourself. I’m sure you’ll make me proud tonight,” responded her master.

Anna placed a large glass bowl below her cunt, slightly forward. Jessica looked down and then turned to look at Rose, who said, “If you wish to be free from these bounds, remember that the bowl below has a capacity of two gallons. When you fill the bowl to its limit, with your cum, we’ll release you.”

That is a lot of liquid. She’s going to be tied for an awfully long time. With her fearful voice, Jessica said, “Mistress, your whore doesn’t think she’ll be able to cum that much. Please mistress, have some mercy on your slave.”

Rose didn’t respond to her pleas but turned and started to leave and said, “Enjoy the moment slave. We’ll be back soon,” and with that all three left the room.

Once alone, Jessica contemplated her life. She used to be a respectable professor at a well-known university. Never in her worst nightmare had she imagined her life would turn up like this. Can she ever get out of this? How long is it possible for her to continue with the demands? Her only hope was Rachael. Could Rachael even help her in this situation? With each passing day, she’s getting trapped in this web even further. How can she expect Rachael alone to fix all her problems? Before her endless questions could elevate her anxiety, her entire audience from last night entered inside the living room.

This is the moment. She had to perform now. Somewhere in her head, she wanted to please everyone in the room. She didn’t want to acknowledge it, but when her master told her he was proud of her performance; she felt a great level of satisfaction. She wants to deny it. Why is she so focused on pleasing her tormentors? Why does she feel an obligation to make each one of them happy? When she’s in her heightened state of arousal only thing her brain thinks of is to follow every command no matter how degrading it is. The guilt only rises back when she’s normal. How can she do such humiliating tasks with such ease when they arouse her to her limits?

“I’m sad to announce that one of our guests, Ben, had to leave early because of a business issue, but we’ll not let you miss him much. Let’s start with the basics,” said Tyrone and pressed a button on his phone.

All her piercings came to life and the instant pleasure she felt was unbelievable. Within a few seconds, she was moaning loudly. A few minutes later, she felt the massive orgasm building and her brain was so glad that she didn’t need permission to cum. The visual cues of her body told everyone that she’s about to cum any second. The moment she was on the extreme verge to squirt to building fluids out, Ty switched the setting to pain.

This was unexpected to her. She thought they would let her cum easily tonight as a reward for her performance earlier. But clearly that was not the plan. Because of the sheer pain caused in each sensitive body part, her brain forgot about the orgasm. The loud, piercing scream echoed across the room. She was in immense pain. And then she felt the pleasure again. Ty repeated this cycle five more times. Each time, she was even closer to her orgasm than the last time. She felt extremely frustrated.

Her pleasure cycles were becoming shorter than she would reach the edge much faster on each cycle. Worse, her pain cycles were longer each time. Jessica was panting heavily by now. She desperately needs to cum. Each time, her frustration level was increasing exponentially. This time when she reached to the edge before Ty could change the setting again, she desperately pleaded, “Please master… No more… Please let… Your… Whore cum… Let her… Cum… Cum… Cum…”

As she felt her ejaculation almost squirt out, she felt the pain, this time much severe than the last. Tyrone had set the pain level to two. She didn’t know that she had to ability to scream this loudly. Every sadist in this room had a massive hard-on after watching her suffering. Rose felt extremely turned-on watching Ty denying the slave her orgasm each time.

Three more cycles with level two, and Jessica lost track of pain and pleasure. Her screams were becoming softer and then the pleasure would increase multiple folds. Few more minutes later as she reached to her edge, Ty increased the level to three. Sudden increase in pain and the frustration, instead of subsiding down her orgasm increased in intensity. And she came. Squirted all her frustrations out of her cunt. Her screams and grunts were music of the ears of her audience. It took five minutes for her to come down from her mind-blowing orgasm. This had been the most intense orgasm of her life.

“Am I a pain-slut?” thought Jessica, but said out loud, “thank you, master. Thank you for allowing your worthless whore to cum.”

Jessica felt all the sensations from her piercings turned off. This brought relief to her mind and body. She looked down at the bowl. It had a lot of fluid for just one orgasm. She had sprayed some fluids out of the bowl. It’s impossible to target the bowl accurately, especially when they had tied both her hands and feet. She would waste a lot of her fluids on the floor. This would make filling the bowl much more challenging task.

Before Jessica could continue with her thought process, she felt a custom furniture placed under her legs. She looked down to figure out what they were doing now. Tyrone had placed a custom designed Sybian saddle under her. It was height adjustable. A press of button and it started rising above. Jessica felt the head of the giant, twelve inches long and three inches wide with realistic black rubber cock. She gasped as she felt the girth and the length of the cock.

Tyrone took some time for her to adjust to the cock and slowly kept increasing the height. Few minutes later she had the entire cock up in her cunt. As she felt completely supported by the Sybian, it helped release some of the pressure from her shoulders. She felt her cunt full to its limits. They slightly sloped the saddle in the front. Anna then attached a giant funnel on the front. Jessica realized that the purpose was for her cum to drop on the bowl. Very thoughtful of her master, she thought.

“How do you feel now, my whore?” said Tyrone.

“Master, your whore is really full in her cunt. This device is fairly new to your whore and doesn’t know what this will do her, but she’s sure that her master knows better what’s good for the whore,” said Jessica not sure why she said things in such a degrading way. She’s adapting to her role from within.

With a press of a button on the device, the rubber cock came to life and started vibrating furiously. Jessica gasped because of the sudden surprising activity inside her cunt. Her voice became much deeper with the extreme arousal and most erotically she yelped out, “Ah! Ah! This… feels so… good… Oh… Oh… Thank… you… Ah… my… master… Fuck… this… whore… oh… my… god…”

And then another press of a button, and the giant vibrating dildo started moving all the way up and down. This dildo would leave her cunt completely and enter all the way inside her with each thrust. Initially, the dildo fucked her gently so she would get adapted to it. Then he turned a knob on the device to max level. This increased the speed ten folds.

“Oh, my god! Fuck… Fuck… Fuck… This… Whore… Fuck… Fuck… Oh… My… God… Fuck…” she kept on yelling the words in a loop. Her body has reached a euphoria now. She did not care about anything anymore. There were no worries about Jason or her brother, Mike. Her brain was in the moment and all it needed was her cunt to be fucked like never. She wanted to satisfy her master. All she needed was to do whatever her master demanded from her. Her entire world revolved around her master at this moment. There was no question about him being her tormentor. This moment, he was her entire world. She knew once she would come down from this euphoria, she would regret this feeling, but right now, she had no control over her emotions. He controlled her mind and body in this moment.

A sharp pain from the strike of a soft leather whip right above her cunt opened her eyes and brought her down from her building orgasm. Another strike too close to her super sensitive clit and a loud piercing scream echoed within the room.

“Hi, I’m Mike. I heard that’s also the nickname of your twin brother. I can be your brother as well. You can imagine fucking him when I fuck you next. I always have a fantasy to fuck my sister. Unfortunately, I don’t have one. You can be my fantasy. You can call me brother from now onwards,” said the Russian-American friend of Devin.

Another strike, this time right on her clit. Pain was too much for her, but something weird happened. Her orgasm kept on building, even with the pain. Worse, more the pain, more intense the orgasm felt.

“Beg your brother for more,” commanded Mike.

“Please,” was all she could say.

“Please what?” yelled Mike.

“Please master, punish your whore the way she deserves,” she tried to dodge the demand and hoped that he would not notice.

“I said call me brother, not master,” yelled out Mike much louder this time.

Something creeped inside her brain, and she submitted much quicker than she would have hoped, “Please brother, punish your whore sister the way she deserves to be punished. Your whore sister has been nasty and deserves to be punished by her brother.”

Another hard strike on her clit and the dam broke down. With huge trembles came Jessica, squirting her hot liquid lava out of her cunt. Her screams mixed with pain and pleasure were a delight for her audience. The intensity of this mammoth orgasm caused her another black out. One common thread they found was each time she had extremely intense orgasms, she couldn’t keep her consciousness.

Jessica woke up a few minutes later to find herself bound in a different configuration. They had bound her on a wooden horse with the saddle still set in her cunt. They bound her in a perfect doggy style configuration with hands and legs bound to each leg of the wooden horse. She was still in the heightened state of arousal and looked around, confused for few seconds. Then she realized where she was and what was happening to her.

She felt cold liquid poured on her asshole, followed by two fingers entered inside. She looked behind to see who was behind her and saw Mike was standing naked, inserting his fingers.

“Rise and shine, sis,” said Mike, giving her a lustful smile.

Tyrone had placed the funnel at the back of the wooden horse now for her cum to drop to the bowl. Then he walked up to the saddle and pressed buttons needed, and the vibrating cock started its magic in her cunt. The generous magical fucking in her cunt, along with the three fingers doing their magic in her asshole. She was already on cloud nine.

Rick walked up to her and whispered in her ears, “Your tattoos claim to fulfill every customer’s fantasies. Mike here has a fantasy to fuck his sister. You’re going to be that sister for him tonight. Make it good and believable. Be his sister tonight and beg for him to fuck you hard,” with that he tapped twice on back of her head as if she was a pet and then left from her view.

“You want this giant cock of your brother deep in your asshole, sis?” said Mike.

Absolutely lost in this erotic world, Jessica gasped out loud and said, “Yes. Yes, please. This whore sis needs that giant cock of her brother deep down inside her asshole. Fuck your sister, Mike. Fuck me. I want that cock. Fuck me hard.”

A single deep thrust and his entire nine inches long and two-and-a-half inch in girth cock was balls deep inside her. A loud gasp left her mouth. She was completely full in both her holes. Mike started fucking her in the dildo’s rhythm in her cunt. Pleasure suddenly intensified several folds in her body. Then he slapped hard on her ass cheek. She screamed because of the surprise, but this time she wanted it. Mike kept on raining hard slaps on both her ass cheeks while fucking her asshole hard.

Nothing existed anymore in the entire world for her, apart from the amazing cocks in her holes. Her filthy talks started naturally without even realizing what she was saying. “Fuck your sis real hard, Mike. Fuck me. Yes. Harder. Harder. Slap that ass hard. More. Harder. Yes. This feels so good. Oh, my god! Fuck me. I have always wanted your giant cock up my holes, Mike. Fuck your sis. I wish Jason could fuck me like this. I should have fucked you earlier. Fuck. Fuck. Fuck… Me… Harder…” and with one final hard slap on her ass cheeks, she came again.

Mike didn’t stop and kept his hard assault on her body while Jessica still lost in her orgasm. This brough two more back-to-back orgasms from her before he deposited his load deep in her asshole. Mike slowly and reluctantly popped his now soft cock out of that amazing asshole and walked up to her mouth.

“Suck your brother’s cock clean, sis.”

Without wasting a single second, she started sucking his cock like a delicious popsicle. While she still cleaning Mike’s cock, she felt another cock buried deep in her asshole. It was Jimmy’s turn now. He started fucking her hard. As Mike’s cock was clean, he left and dressed back. She then felt another hard slap from Jimmy on her ass cheeks, but it hurt exponentially more than before. She shouted out loud and turned to see why it would hurt this much. She saw Jimmy was wearing rubber gloves with grooves on them. They were like dishwashing gloves but specifically designed for bondage punishments. They would leave no permanent marks or cuts but would hurt terrible.

After a few more slaps, she realized she was feeling even more aroused by this increase in pain. The pain mixed with the pleasure was overall, increasing the intensity of her pleasure.

“Harder. Please harder. More. Please, master. Hit your slave harder. Please, master.” Again, she started a loop of her dirty talk. Jimmy felt even more aroused as his sadist part of the brain felt amazing with this woman. He obliged with her requests and started hitting her ass cheeks much harder. When she came, it was mind-blowing orgasm. He didn’t stop, and neither did she. She had countless back-to-back orgasms. She was too sensitive by now, but her brain kept telling her she wants more. More, much more. By the time Jimmy deposited his load in her asshole, they realized that she had passed out again.

Daryl felt disappointed because he wanted to have his share as well before they leave. Ty convinced him she’ll be back soon, then he can have his share.

Jessica woke up again few minutes later to find herself bound in a different configuration. She was still on the wooden horse, but this time on her back. Her hands were on the side tied using multiple ropes around her abs. Both lets tied wide open with metal chains attached to stainless steel rings on either side of the walls in the room. Someone angled the saddle slightly differently and buried the dildo deep in her asshole. Her wide-open cunt was available for the fucking she was about to receive.

Daryl positioned himself between her legs. First, he pressed the buttons on the saddle, which started the vibrating cock to move in her asshole. This dildo was too big for her asshole, but she had no choice but to take it. Then looking directly in her eyes in penetrated her cunt in a single thrust. She again gasped loudly. As Daryl got in rhythm with the cock in her asshole, she felt another orgasm building soon.

She saw Daryl was also wearing similar grooved gloves to his right hand. He grabbed her body below her tit from his left had to gain a good balance to fuck her. With his right hand, he started smacking her tits hard, in sync with his deep and hard thrusts.

Her tits were soon darkest shade of red because of the assault they received by Daryl. But like before, she reached her orgasm much faster than usual when he started smacking her right on top of her super sensitive nipples.

Again, she yelled out desperately, “Fuck. This is amazing. Harder. Hit these whore tits harder. Yes. On these whore nipples. Again. Harder. Oh, these nipples are sensitive. Again. Another. Harder. Oh… Fuck… Fuck… Harder…” and with that, she came again.

She had six more mind-blowing, earth-shattering orgasms before Daryl deposited his load deep in her cunt. Her entire tits felt too sore. Daryl dismounted her, and she sucked his cock clean, mindlessly. She closed her eyes and felt extremely exhausted by now. Her entire body would be sore for days to come. Good thing was that she would be free for the rest of her vacation and can recover better from her assault tonight.

She felt someone removing all the bounds from her body, but she didn’t open her eyes. She thought to take some rest even though it would be a bare minimum before she’s moved to another position. A pair of hands scooped her from the wooden horse and took her to the next position. She opened her eyes now to see Regie carrying her to a different side of the living room.

She saw there were two heavy benches placed wide apart from each other and in between the benches was the bowl. Jessica couldn’t believe how much she came during this entire ordeal. The two-gallon bowl was already almost full. “How is it even possible?” she thought.

Reggie, with the help of Rick and Jamie, placed her kneeled on each bench. Her ass settled on top of her calves with her back straight. They tied ropes all around the bench and between her thighs. Next, they tied both her hands together and then bound them above her head to a metal chain on the ceiling. She realized they had bound her to provide complete access to all her already super-sensitive body parts.

“Now it’s ladies’ time,” said Rose, excited for her turn. Anna followed her, and both had wooden paddles in their hands. The paddles also had rubber padding with rough grooves on them. This is going to be much more difficult for Jessica.

“I’m really excited to finally be a slave owner for a night,” said Anna.

Anna also had the similar glove on her left hand. As she reached in between and started rubbing Jessica’s clit with her gloved fingers. This sudden rough treatment brought intense pain to her super-sensitive clit.

“Please, mistress. Please, it hurts. Please be gentle to your slave, mistress,” begged Jessica.

Anna slapped hard right on top of her clit with her gloved hand and said, “Shut up slave or you’ll make it worse for yourself.”

Jessica forced herself to shut up and try to deal with the pain. Anna made it worse soon by inserting two gloved fingers and rubbed using her thumb with heavy pressure. The fingers felt fantastic, but the thumb was painful on the clit. This again brought the pain mixed with pleasure sensations back to her. Few minutes later, Rose realized by her body language that she was on the edge and was about to cum any second. She gave a nod to Anna, and she removed her hand instantly. This was in sync, followed by a hard smack right on her nipples by the paddle by Rose.

Jessica yelped out loud, but the hard smacks rained on both her nipples for around next two minutes. Then suddenly she felt a hard smack on her cunt, along with her tits. She was so close to her orgasm and now she felt raining paddle smack on both her tits and her cunt by these two devil mistresses. Something weird happened again after a few more smacks. She felt on the edge again. With no pleasure, she was on the edge just by the pain this time.

“What is happening to me?” thought Jessica but yelled out in desperation to cum, “Harder. Mistress, please hit your slave harder. Your slave is going to cum any second, mistress. Please hit your whore harder. More. Again. Yes…” with that, she came hard again. Rose kept on hitting on her tits while Anna started hitting right above her cunt. This continuous assault while she came prolonged her orgasm exponentially. Her entire body kept on shivering and trembling, and her ejaculation would not stop.