Teacher's Dilemma Ch. 04

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."

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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.