Teacher's Dilemma Ch. 08

Jessica woke up to find herself back in the dungeon. She did not know how she got here. This time, they tied her upside down with ropes attached to the ceiling. They had her legs spread wide open and hogtied her arms behind her back. This was one of the most vulnerable positions for her. Next began her painful and frustrating pleasure for the next couple of hours. Each man took their sadistic fetish out on her and wouldn't allow her to cum.

Eventually, when everyone was too tired to continue, they removed her from her bounds. The judge again ordered James to take care of her. This time, while massaging her body, Jessica begged, "please I beg you, don't torment me anymore. I can't take it. Please." James nodded and gave her a professional non-erotic massage this time. Once she had her dinner; he told her she must sleep in her cage. Jessica tried to negotiate with him but realized that he also has no say in the matter. Finally, she agreed and crawled her way back into that miserable cage. James tied her in the same way as she was last night.

"Good night," said James, and walked out of the dungeon.

Jessica couldn't respond to him and kept thinking about how much worse they were going to make her life from here. If this is a weekend at these creepy twisted sons of bitches, then what would it be like at the club? Her negative thoughts kept ongoing for several minutes until her tired eyes dozed off to sleep in an extremely uncomfortable position.

* * * * *

Sunday

Like last night Jessica woke up to the noise of her cage opening. As expected, it was James standing outside. He unbound her and pulled her out of the cage. Again that night, she had peed inside her cage. The routine was similar again. He gave her a nice bath, followed by the similar erotic and frustrating massage. After her breakfast, he brought her out into the living room area.

He had specific orders to follow. He cuffed her arms behind her back and attached all the gadgets back again. After pressing the button, everything came back to life. But the problem was the sensations were too low. It was frustrating and agonizing. Once done, he left her alone.

For the next few hours, people went in and out of that area without acknowledging her presence in the room. It was like she didn't even exist for them. The sensations grew even more frustrating for her now. This was the most anything had aroused her in her life without bringing her closer to orgasm. She desperately needed someone to touch her or fuck her, but no one did. This was their mind games. They needed a desperate pet begging to fuck her with no pressure from anyone.

Finally, when she saw one of Kurt's friends Ryan walk in, she couldn't control herself and begged him for something she never thought she would ever do on her own.

"Master Ryan, if you would like to fuck your pet, she would be extremely grateful to her master for his generosity."

"No, I don't want to fuck you, pet. But if you want me to fuck you, then beg properly."

Jessica felt a serious hurt from the rejection by this old man who she wouldn't even look at under normal circumstances. But these are not the normal circumstances.

"Master Ryan, your pet begs you to fuck her. Please, master. Your pet would be grateful to you throughout her life if you would fuck her."

"Okay, if you're so desperate then I'll fuck you."

"Thank you, master. Your pet will always be grateful to you."

Ryan came to her with a bottle of lube and forcefully mushed her face on the floor with her ass high in air. He poured generously on his cock and her asshole. He shoved his cock hard in her asshole and placed his foot on her face. It was a painful fuck for her. He came fast and deposited his seed in her hole. After he pulled out, she felt even more frustrated than before. He even forced her to suck his nasty cock clean, which she did.

It was then every friend of the judge made her beg to be fucked by them. All of them fucked her asshole with no care for her pleasure. James brought food for her, which she ate like a dog. It was 6:30PM now and she had tears in her eyes out of this prolonged frustration building inside her. Her cunt was soaking wet, yet she was nowhere closer to her orgasm. Then she saw Rick standing in front of her. She had a smile on her face after seeing her. Was it Stockholm Syndrome? Quite possibly.

Rick took her from the farmhouse. As per the judge's last demands, he made her do the extreme edging exercises throughout the trip back home. Jessica reached home excessively horny and willing to do anything for permission to cum. Which she would not get tonight. A brutal mental manipulation.

* * * * *

Devin's Mansion

Rachael walked inside and saw Jimmy leaving the house. "Where's Devin?" she asked him.

"In his office. Not in a good mood, so I'd say be careful."

"Okay, I will remember it. Thanks."

She continued towards Devin's office and when she reached there as the ritual; she knocked on the door.

"Who's there? If it's unnecessary, then just leave now," came the response from Devin.

"Hey this is Rachael. And yes, it's necessary," she said.

There was a loud groan from him and then he said, "come in."

She walked into his office and sat in the chair opposite him. "Looks like you're not in a good mood?"

"That's what you think is necessary discussion? Get directly to the point," he said in a detached tone.

This was a shock for Rachael, but she decided not to poke the bear. She continued, "I have credible intel from my source that we have a mole among us. This person is an undercover FBI agent. We need to find this person as soon as possible, Devin. If we're too late, it could crumble our entire empire."

"Did your source also tell you that Abraham Lincoln died on April 15, 1865?" said Devin in a sarcastic tone.

"What the fuck Devin? I'm having a serious discussion here. I'm tolerating your behavior that doesn't mean you get to disrespect me. If you're having your mood swings, that's not my problem," she said, now clearly angry and frustrated by the behavior shown by Devin.

"You're tolerating me? I'm tolerating you, Rachael. You forced me to kill my own little brother. He was like a son to me. I raised him most of his life. And you have the gall to tell me you're tolerating me. If you think you can run this fucking gang without me, then you're welcome to try. Don't fucking tell me how I should behave in front of anyone. Fuck you, Rachael." Devin's tone was much angrier than she expected, but at least he was letting things out of his system.

"I understand what you're going through, Devin. But this was something we all knew before we got into this. There will always be consequences and collateral damage to everything we do. But if you think I wanted him dead, then you're completely wrong. You should know that it was me who saved him for so many years. Just because he was your brother. You know it, if he wasn't he would have died long ago."

She took a deep breath and continued, "he had such an enormous ego and was a stubborn son of a bitch. How many times people reached out to me to get rid of him, but I talked them out of it. And you know why I did it, Devin? Yes, you guessed it right. Because he was your brother. But at some point, he was going to cross all limits. You should have known it, but you kept ignoring all the signs because he was your brother. I can't ruin years of hard work we put into just because he cannot handle his ego. Now if we're done with bullshit, can we talk business?"

Devin realized she was right at all counts. Eventually it was his decision as well to get rid of his brother and now he can't put all the blame on her. He took a few deep breaths and continued, "I had this information about the mole for a while. One of my sources confirmed this information a few days after Ty died. But I was waiting on full proof confirmation before going all in. A few days ago, I got that as well. I have a plan to flush the mole out. Ben and Jimmy are working on it as we speak."

"We have little time, Devin. Whatever your plan, make it work fast. A lot lies upon the club now. Steve doesn't know what's my real motive behind the grand club debut of Jessica and I want to keep it that way. Let him have all the fun he wants with her if it doesn't affect our plan. It is extremely important for our business' expansion, Devin. For now, Jessica is the key to the door that'll open all doors for us."

"I know what's at stake, Rachael. Don't worry, I'll flush the mole out before her debut."

Rachael felt relieved after the confidence shown by Devin. She finally left his office and hoped for the plan to work.