Teacher's Dilemma Ch. 09

Special thanks to "Ellie aka Worthless Whore" for volunteering with the editing of this chapter. Apart from helping with the grammatical issues, her valuable research and inputs were the core for this chapter. Her understanding of the vision of this series has been impeccable. If you enjoy it, I'd appreciate if everyone can give her the deserved recognition in the comments section.

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.

Special Notes: I have intentionally dropped clues at each chapter. People paying attention might guess what could happen next.

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Devin's Mansion (25^th January)

Reggie parked his Ford F-150 outside Devin's mansion. As he got out to walk inside, he saw Terry, David and Mark waiting for him. "They also called you guys for the meeting?" asked Reggie to them.

"Yes. I'm surprised that Jimmy called everyone individually for the meeting. It's unlike him. Why do you think he called us?" asked Terry, with fear in his voice.

"Don't be scared. We're already here, so we'll find that out soon," replied Reggie.

They all went inside and saw Rick, Jamie, Ray, and Steve already waiting in the living room. Reggie walked up to Rick and said, "do you guys know the agenda of this meeting?" Rick shrugged his shoulders and shook his head, indicating no knowledge of the meeting. He looked towards others with a questioning expression, and everyone shook their heads. Now Reggie knew this was out of normal behavior for Devin and his inner circle. At least someone should have an idea about the meeting's agenda.

Everyone in the living room was discussing the reason for the meeting when Rose joined them, along with Anna. This completely threw all their logic out of the window. "Why would they call them to this secret meeting?" thought Reggie. This made no sense at all. Why so much secrecy? They continued various probable reasons but could not reach any conclusion.

"Why are you guys so worried? We'll soon find out why we're here. Now stop freaking out and let's wait in silence," said Rose. She also felt the fear but showed her brave character to everyone else.

It was then the members of Devin's inner circle Mikhail 'Mike', Jimmy and Ben walked in. Jimmy had a custom designed butterfly knife in his right hand with which he showed some expert level tricks while casually walking towards them. They reached the living room where everyone sat impatiently waiting. From the center table, Jimmy grabbed an apple and using his knife, he gestured to everyone to follow them.

The suspense was killing everyone as they followed Mike, Jimmy, and Ben towards Devin's office. Once inside, Ben sat in Devin's chair and calmly placed both his palms on the giant wooden desk in front of him. Mike took a sofa chair a few feet away from Ben. Jimmy casually sat on top of the desk, as he cut a thin slice of apple from his knife and ate it. All three of them were facing the door where everyone else stood patiently waiting to know what the hell was going on?

"Well, I think you all must be dying to know why we've called you here suddenly. I'll keep it short, so we don't waste anyone's precious time. We've got information from credible sources that feds are on to us and possibly we've a mole among us. So, we've changed the rules of engagement from now onwards. It's extremely difficult to sweep every place we go and every person we meet. From now onwards, we'll make and communicate all critical decisions only within the confines of this room," said Ben, looking into everyone's reaction to this latest information.

"It's easier to look for any bugs in a smaller space daily. Plus, we will check everyone before entering this room for potential wires. We will compartmentalize all the information. Meaning you get to know what you need to know, nothing more. Questions?" Ben looked for anyone who might be nervous.

"But why am I here? I don't even work for you guys?" asked Steve, now significantly frustrated after waiting so long.

Jimmy stood up from the desk and walked up to him with a smirk on his face. He sliced another thin piece from the apple and ate it while keeping eye contact with Steve. While chewing the apple, he said, "like we give a shit. Everyone who receives help from us is here. Whether you work for us is never the question." Softly, he ran the tip of his knife on his cheek to send a chilling message, causing no physical harm. "Does that answer your question?" he finally said in a condescending tone.

"You know who you're talking to, right? I'm not the punk who works for you guys and would be afraid of people like you," said Steve, now getting even more angry at such disrespect by Jimmy.

"Enlighten us. Who the fuck do you think you really are? President of this country? You're just a guy with a lot of money and we've destroyed people way richer than you are. So never overvalue yourself in front of us. You're alive because we don't have a reason to kill you. Don't give us one," said Mike from the other end of the room in a very stern and commanding voice.

"And the way you're responding brings a lot of attention towards you. Why are you so nervous about being here? Are you the mole?" asked Ben.

"What? Why... why would... I be the mole? I have nothing to... gain... f... from... the FBI," said Steve, stammering through his sentence.

"We don't know. But we suspect everyone. Can't be too careful, right?" said Jimmy, still eating the apple.

This time, Steve stayed quiet. He thought, there's no point in escalating the matter further. All these people are crazy, and they won't think twice before killing him for their ego. "I'll have my time and then I'll show these thugs who I am," he thought.

"But I don't understand. If the mole is in the room, why would you share the entire plan with him or her?" asked Reggie.

"So that the mole knows that the game is fair now. If the FBI is on to us, then we're also on to them. It's a race to find who wins," replied Ben.

"We don't have all day to talk about this new arrangement. I just want a nod from everyone here that they understand this rule and will always abide by it. At least till we find the mole," said Mike again in his stern voice.

When everyone agreed to the updated terms, Ben told them to leave. "Do you really think that the mole will take the bait?" asked Jimmy to Ben.

"We'll see. But the probability is high that it'll work. But if it doesn't, then I have another plan," said Ben, in a confident voice, "either way we'll find out who's the mole."

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Friday, 1^st February

It was the Friday after Jessica's terrible ordeal at the farmhouse. Per Rachael's command, both Rick and Jamie need to give her rest. She didn't want to break her physically before the much-anticipated debut at the club. Which meant they cannot fuck Jessica until Rachael gives a green light. They could play with her to keep her on the edge, but no bondage or physical punishments allowed. Every day, she received a full body massage which was extremely relaxing but erotic. By the end of each massage, she desperately needed to cum, but they wouldn't allow it.

Jessica got out of the shower with her morning routine and makeup done. Completely naked, she walked to the living room as instructed by Rick. He would give her the dress for her day. As she entered the living room, both Rick and Jamie were waiting eagerly for her entrance.

"Let's get you ready for your day, professor whore. Come here fast," ordered Rick with childish excitement in his voice. She followed the instructions and waited for him to do as he wished. "Stand in your waiting position and do not move until I say otherwise," commanded Rick.

Jessica followed the command with no hesitation. He pulled out a curved silicone g-spot stimulator and inserted it inside her cunt with one smooth push. The base of it had a small, insulated wire that dangled outside of her cunt. Jamie followed his brother's lead and quickly inserted a similar sized butt plug in her ass. Then came even smaller versions of clips that she had endured during her stay at the farmhouse. They attached those clips to each of her piercings.

"These are the refined versions of our patent-pending chips. They can be much more intense and energy efficient than the previous version," said Rick boasting his knowledge, as if she should grant him higher grades based on it.

Next, both brothers picked weird underwear, at least that's what she thought. It was a combination of soft stainless steel and leather. Jamie told her to push her hands through the top part of the leather straps of this custom bra. The outside of the bra was stainless steel, while the inside was soft leather for comfort. He carefully attached the metal clips on her nipples to some sort of charging connection designed inside the bra.

Once satisfied, he went towards her back to tighten the leather straps. He tightened the straps more than what she was comfortable with, but she had become habitual to their tricks and torments by now. The bra also had an attached leather collar with a giant stainless-steel ring at the center. He tightened the collar as well. Below the bra was an attached soft black leather corset. Jamie then worked towards tightening the corset and made her take a deep breath, and decided that it was now tight enough. This combination would need some practice for her. It was too tight.

Below the corset was the stainless-steel chastity belt with padded soft leather for some comfort. Rick carefully attached the wires from both her g-spot stimulator and butt plug and the clip on her clit, piercing to various smallest connection ports she had ever seen. Then he worked towards tightening the chastity belt. Once the fit satisfied him, she heard a click sound, which meant that the belt's locked.

"Now let me explain your new gadgets here. I've already explained the clips to you. I connected the stimulator in your whore cunt and the one in your butt, as well as the clips, to your new underwear. It's custom made with a much larger battery pack inside it. So, it can keep all the smaller gadgets to function for days without interruption and need to recharge. Best part is that if the main battery pack needs charging, we can charge it while you're wearing it. Which makes it possible for us the never remove it and we can keep on torturing you forever. Plus, if you need to use the restroom, you'd need our permission to remove it. It means that you should not disappoint us ever, if you wish to cum or pee," stated Rick.

Jessica couldn't believe what she just heard, but since she had no choice, she nodded meekly, showing that she understood her situation.

"Now, carefully listen to your task for the day. You must call Professor Phillip in your office, seduce him, and give him a glorious blowjob in your office. How you would achieve this task before the end of the day is your responsibility, but if you failed, then I will not remove this belt until you finish your task. That would mean at the earliest it'd be Monday," ordered Jamie.

Jessica's worst fear became reality now. Professor Phillip's respect as a professional has been her utmost priority. She raised her hand to ask the question. "You better not beg us to change the task. Ask your question, whore," said Jamie.

"Please, master, your whore will seduce anyone else in the university but Professor Phillip. Please, master, have some mercy on your humble whore," she begged, hoping for some mercy.

"I already gave you the choice. Either seduce him and give him a mind-blowing blowjob or stay locked in this chastity belt. Choice is yours," replied Jamie.

She knew that there's no other response for her now, so she agreed. After today, her relationship with Phil will change forever. He would have no respect for her as an assistant professor who once was his student. They gave her a black turtleneck dress that went a few inches above her ankles. "At least the dress covers me adequately," she thought. To complete her dress was the six inches high black heels that were also locked by Rick. Only Rick's phone can unlock both her heels and the chastity belt.

"And for your information, my girlfriend and your new mistress, Claire, will also join us tonight. She'll also stay with us and help us better train you," said Jamie.

She didn't react to the last statement by her master. Rick commanded her to wait for them in her car. She followed the instructions like a trained pet.

"Why the fuck would you bring Claire into all of this?" said Rick.

"Because she's my girlfriend and I also have a say in this matter. Don't forget you're her master, not mine," replied Jamie.

Rick stared into his brother's eyes to intimidate him like he has done multiple times in the past. But this time it didn't work. Jamie was determined by his decision and Rick didn't want to break a fight with Jessica standing outside. He reluctantly agreed.

As they were walking outside, Jamie asked, "I heard you broke up with your girlfriend?"

"Yeah. I don't think she was for me, anyway. Constantly nagging me for not spending more time with her. I simply called it off," replied Rick.

Jamie knew he was lying. They both could easily tell when the other was lying. He also knew that Rick was getting obsessed with Jessica and she was the reason behind his breakup. Both brothers sat in the car as Jessica drove them to the university.

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London (18^th February)

The past month had been an intense training routine for Jason. Sam would bring him to extreme edge and then ruin his orgasm, sometimes painfully. What she didn't realize was that this painful frustration was breaking him mentally, just not like she wanted. He had lived his entire life as an alpha male, and he wouldn't adjust to this submission. The plan that worked flawlessly for Jessica wasn't working that well with Jason. And the problem was that Sam did not know about this recent change in him. He had reached a point where he no longer cared for the consequences. The only goal for him was to end this misery and soon he will do it.

The breaking point for him occurred when, as part of his humiliation training, she used cock and balls as vibration rings inside a painfully tight cock cage. But the worst part was that he was giving a presentation at work showing his innovative marketing campaign. Sam would turn the vibrations on randomly, causing heightened arousal and pain. The entire hour and a half long painful humiliation brought him to reality. He had worked too hard to reach where he was in his career, and he can't let ANYTHING ruin it. This was getting too far, and he needed to get back in control.

That night when they were in the bedroom, Sam said, "remove all your clothes, you pathetic loser."

Jason followed the instructions instantly. He had the plan clear in his head. First, he needs to get his cock free from the cage. It was a high-tech cage only unlocked by her phone upon entering a passcode which he didn't know. Once he was naked, he desperately looked at her, waiting for some release of painful pressure on his cock.

"Aw! Do you need me to let you pathetic cock free from its cage?" asked Sam with a smirk on her face.

"Yes, mistress," replied Jason.

"Beg. If I'm happy with it, then I might consider it," said Sam.

"Please, mistress. Your slave desperately needs some relieve from the pain and pressure from his cage. He'll do whatever his mistress desires as a requirement for her generosity," begged Jason, acting as genuine as he could under the circumstances.

Sam smiled after listening to the response from him and pulled her phone out to unlock his cock cage. She entered the passcode and pressed the button, and it unlocked the cage. Jason didn't waste a single second and threw the cage and vibrating rings away from his cock towards the corner of the bedroom. With his cock now released from the pressure, he took a deep sigh of relief.

"What the fuck do you think you're doing? I never gave you permission to remove the cage. This will be punish..." Sam couldn't finish her sentence as she walked up to him in her anger, but as she reached in front of him, he quickly pounced on her and soon she found herself in a headlock. She struggled for a couple of minutes, but he was too strong for her. Before she knew it, everything went dark.

Sam opened her eyes to find her hands bound spread wide and her legs stretched and bound either side of her head to the bedposts. This was an extremely uncomfortable position for her, and it granted full access to her holes. She looked around to find the bedroom empty. Several minutes later, Jason entered the room. "Oh, rise and shine, sweetheart," he said with a bigger grin on his face now.

He walked up to her and inserted two fingers in her cunt and began fingering her cunt while massaging her clit. It took only a couple of minutes for her cunt to release the fluids, and her breathing increased substantially.

"When you're physically weaker than your opponent, stay within your limits," he said calmly while continuing to finger her. "I was never a submissive person, but it surprised me I waited this long for my revolt. And you know why it took me this long? Because of Jess. I love her way too much and never imagined my life without her. But when you brought this stuff to my work as well, something clicked in my head. There's no way out of this shit until I take matters into my own hands," he continued.

It was at this point Sam realized her mistake. Jason wasn't the same person as his wife. She followed the same plan to trap him, but she didn't account for his aggressive revolt if things got out of hand. Jessica had multiple opportunities to break free, but somehow, she didn't. She was too afraid of the outcome. Jason no longer cared about the outcome anymore.

"The worst outcome for me would be a divorce. Honestly, it'll break my heart and I'll be a mess for a long time, but if I keep following your commands, things could get much worse. I have a chance with my Jess, but with you, I don't have a chance. So today I took my chances with the love of my life. I guess you didn't take this outcome as a possibility under your plan. Oh yeah, don't dare cum without my permission, you fucking whore," said Jason with clear aggression in his voice. The sudden change in his tone frightened Sam as she didn't expect him to be like a dom.

As she reached to the edge of her orgasm, he removed the fingers and gave her five hard smacks right on her cunt. Her screams echoed through the room. The smacks were much harder than she expected. It was like he was taking his revenge for the entire month of agony pushed upon him. He continued his torture on her for over thirty minutes with smacking her tits and cunt every time she reached the extreme edge of her orgasm.

He realized how much he needed his own release. He inserted his cock in one thrust, deep in her cunt. What followed next was pure raw animalistic pounding of her hole. He was too rough, which turned her off, but he didn't care anymore. All he needed was his satisfaction. It only took a few minutes before he pulled out and jerked off a giant load of cunt all over her tits, lips, eyes and covering her entire face. It was too much cum for her. He hadn't had an orgasm for over a month and now the amount of jizz was massive.