Teacher's Dilemma Ch. 04

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 24x7 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.