Teacher's Dilemma Ch. 08

Special thanks to "Ellie aka Worthless Whore (Ellie_RH)" 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.

* * * * *

Few days ago

Rick was excited as he walked to Rachael's office. She had given him certain directions to follow for Jessica's further training. He and Jamie had both followed the instructions to every detail, and it worked its magic. At the university they kept her in a constant state of arousal using the advanced gadgets on her body. They didn't contact her but kept her at the peak of her arousal. At home, both brothers would practice various forms of advanced bondage position and techniques on her.

Each night, both brothers would fuck her multiple times but wouldn't allow her to cum. From all the events of her recent past, she had lost all hope. Somehow, she continued through her misery. She had done as they demanded but wouldn't give them the pleasure of breaking her mentally further. Jessica held her fort for several days. She fought well and pretended that her extended and extreme orgasm denials were not affecting her.

The problem was the whore within. Jessica was fighting her for days. But she loved to grant absolute control to her tormentors. Jessica's biggest enemy was the whore within. Each day, she was winning a little more. The whore was overpowering Jessica and the more they aroused her, the more powerful the whore got. Jessica knew she couldn't control her any longer. Whore's screams were getting louder by the day and Jessica couldn't get them out of her head anymore.

Jessica just didn't want the whore to overpower her. The whore didn't care about Mike or Jason or her own career. The only thing that mattered to the whore was her physical pleasure. If they would allow the whore to cum as much as she wants, she would do whatever they wanted from her. Even forget Mike and Jason completely. These days, Jessica didn't fear Rachael as much as she feared the whore. They knew how to play the whore like a musical instrument.

All Rachael intended to do was make the whore primary and Jessica secondary. The moment that happened, they would own her completely. Mentally, emotionally, and physically. Last night's session was too much, and the whore took over completely. First time in days, she begged the brothers to let her cum. She agreed to do whatever they demanded of her if they let her cum. They continued to torment her further for several hours. The whore cried and begged for permission to cum. Eventually, when they felt she couldn't take it anymore, they denied her.

That night, the whore blamed Jessica for all her miseries and torments. There was a massive fight between the whore and Jessica. Whore won it clearly, as she was way too powerful for Jessica to control now. Jessica meekly accepted that she'll do whatever the whore tells her to do with no question if she stops yelling at her. The whore was fully out. She had become primary, and Jessica is now secondary. The whore doesn't care about Jessica and her life. Not even a bit.

Rick opened the door to Rachael's office and directly entered inside and said in his excitement, "your plan worked like a magic trick. Flawlessly. I must tell you, one thing I'm dying to say. You are a fucking twisted bitch who knows exactly what to do to gain absolute control over people. And I love it." With that, he sat on the chair opposite to her.

Rachael was working on a disaster recovery issue for the gang. She had got information from a source within the FBI that someone unknown is doing an undercover investigation on their gang. The person in charge of the investigation leads a small team. And it's appointed on a need-to-know basis. Not even her source inside the FBI knows about who is leading the team and who all the members of this team are. All he could find out was there's a deep undercover agent already in place. FBI had infiltrated their gang, and she didn't know it. This was the biggest failure in her planning. And she couldn't accept it. She needs to find this mole and deal with it.

Rachael stared into Rick's eyes for the longest period and didn't say a thing. If you could kill someone from a stare, she would have at that moment. Rick realized he did something wrong and looked down, trying to avoid eye contact.

"Who are you?" asked Rachael in a stern tone.

"What?"

"Are you dumb? It's a simple question. Who are you?"

Rick swallowed in his nervousness. "I fucked up more than I estimated. But how?" he thought. "I'm Rick. We know each other," said Rick in a broken, soft, and nervous tone.

"Do we?"

Now she confused Rick. "Did she genuinely forget me, or this is one of her twisted mind games?" he thought. But all he could do was just nod.

"I don't think so. Because if you would know me then you WOULDN'T FUCKING DARE TO BARGE INTO MY OFFICE WITHOUT KNOCKING AND SIT IN FRONT OF ME WITHOUT MY PERMISSION," she lost her composure and yelled at him.

She made it absolutely clear to Rick who was the boss around. He gets excited and forgets where he belongs on the ladder. "I'm sorry. I'll go out and come back again. I got excited. I'm sorry," he said and left her office.

When she heard the knock on the door, she took a deep breath to calm herself down. "Come in," she said.

Rick walked into the office again, but this time, he was more cautious of what he would say to her. He stood in front of her but didn't dare to sit this time. Rachael, as a punishment, didn't allow him to sit as well.

"Now speak. I don't have all day for you here. I have important work to do," she said in her seething anger. She was angry at her own failure but took it out on Rick.

"We did exactly as you've told us, and it worked like a magic trick. She finally gave up and begged us to allow her to cum. But as per the plan, we didn't," said Rick but with total lack of excitement in his statement.

"Perfect. Now listen to me carefully and don't use your own head. Do exactly as per the plan. Nod if you understand," said Rachael, humiliating Rick like he was some dumb kid who wouldn't understand basic instructions. But Rick knew the power dynamics and swallowed his ego and just nodded. Rachael explained her detailed plan to him. She had detailed it down to a tee.

"I'm sorry to ask, but it's really aggressive. Do you think it would work? And would she still do as we say afterwards?" asked Rick.

"It would work if you don't use your own head and do exactly, I've told you. And if she wanted to back out, she would have done it already. We've done way more to her already where a normal woman would have backed out. Her brain is stuck in a dilemma where she can't decide what she wants. She will continue to do as we command her. If you follow my plan, her dilemma will continue to grow, creating more confusion for her. She wouldn't be able to make any sane decisions."

Rick nodded and agreed with her statements. "I don't think there would be much problem forcing her to sign those documents. She's already struggling to make basic decisions because of her prolonged arousal and orgasm denials," he stated.

"Yes, that's not what I'm worried about," she said. She opened her desk drawer and pulled out a small bottle of an unknown gel and threw it towards Rick. He caught the bottle and looked at her with a questioning expression. She continued, "this will help gain her absolute compliance. One of Steve's club members made it. This is extremely strong and long duration. They had written instructions of use on the bottle. It's remarkably simple."

Rick placed the bottle in his pocket. Rachael continued again, "I'm more worried about that fucking horny judge. I've handled everyone. Witnesses, lawyers and even folks at the university. Everyone is under my control. Most of the folks are already members of the club, so it wasn't too difficult to manipulate them."

"But I thought the judge was also a member of the club?" asked Rick.

"Yes, he is. But that fucker had promised some of his friends about a crazy weekend with her. He says that now it's about his prestige. He had agreed to do it but wanted her at his farmhouse for one weekend with his friends."

"What's the problem with it? She can handle it."

"You clearly don't know a thing about the judge. He's fucked up. Complete sadistic person. His friends are even worse. I don't care if she can handle it. I'm worried if in their excitement they do too much to her and we don't even get to see her debut at the club. The club is more important than the judge. But you're right. She'll have to handle it. Even Steve couldn't get through to the judge, so I guess we must trust them. We've made him understand that there shouldn't be any permanent damage done to her physically. I'm hoping he will follow through with his words. We're so close to her debut now that I don't want to take unnecessary risks. And he's an unnecessary risk."

Rachael thought for a moment and then said, "fuck it, let's do it. Make her promise that she'll give her absolute compliance to the judge over the weekend. Any complaints from him will cause a profoundly serious punishment."

"Will do," said Rick.

As Rick turned towards the door to leave, she said, "and remember Rick, who's the boss around here. I won't forgive that kind of behavior again. Know your worth and place in the grand scheme of things. You're replaceable. So, show your worth before I replace you like Ty." Her mention of Ty was an explicit threat, and he instantly got the point. He nodded and left the room.

* * * * *

Present Day

Jessica had felt so much better over the past few days since the whore took over. Whore's only purpose was to satisfy her masters, and she enjoyed doing it. She wouldn't miss any opportunity to humiliate and degrade Jessica. According to her, Jessica had caused all her misery. Only if she stops being such a cunt, everything would be fine. It's because of Jessica, her masters wouldn't allow her, her long awaited orgasm.

Jessica had surprised both Rick and Jamie with her absolute desire to please them. She had been perfect since the whore took over. She was standing in the living room, entirely naked, with just her high heels on. Her hands locked behind her head; legs spread wide open. Her satisfaction just to please her masters was clearly visible on her face and body language.

"How many times do I need to remind you to keep that cock hole of yours nice and wide when waiting. Your cock holes should be ready for use at all times, if you forget again then I'll start using a ring gag or mouth lock on you bitch"

The whore immediately opened her mouth wide to form an inviting "O" for her masters.

"In-fact open wide, whore I'm going to measure you and I expect you to always have your cock hole this wide when commanded, if it's not you will be punished. "

Rick then took a measurement vertically between her top and bottom teeth clearance and then across the width at the first molar.

"You'll stay exactly in this position until I say otherwise. Understood." Said Rick.

"Yes, master. Your whore will not move until her master gives her permission to do so," replied Jessica in a never seen before excitement. "You will shut the fuck up and let me handle everything from now onwards. If I even hear a peep out of your mouth, I'll make you regret it. I'll please my master and he will take care of me." Powerful voice of the whore echoed within Jessica's head, and she didn't dare to argue with her.

Rick took out the bottle of the gel given to him by Rachael. He had disposable latex gloves on. After taking out a generous scoop of the gel on his fingers, he bent down and inserted those fingers into her cunt. He used those fingers to apply the gel evenly inside her cunt. For a good measure, he took another scoop and applied more. Once satisfied, he took another scoop and generously rubbed it on her clit and around her clit hood. While doing so, he didn't miss teasing her more than he should have. She already felt too aroused.

"You know, whore, you're not allowed to cum, right?"

"Yes, master. Your whore will not cum without permission."

He felt satisfied with the application of the gel on and around her clit. He stood up and applied another generous amount of gel on and around her erect and sensitive nipples. Rick ordered her to bend and spread her ass cheeks. As per her expectation, the generous application of the gel finished the task.

She stood up and Rick ordered her to grab her dress from the box outside and once dressed, wait for him outside her car. It was a black turtleneck dress that went a couple of inches below her thigh tattoos. Once she had her hair extensions and dress on, she went outside and waited for her master next to her car. Rick and Jamie came out, and she drove them to the university as per her daily routine since last few days.

On her way to the university, she felt a serious tingling and warmth begin everywhere her master had applied the gel. It was too strong and her need to cum increased exponentially. As she parked her car, she turned to her master and said, "master, your whore is struggling to control her orgasm. Please master, if your humble whore has been good, please allow her to cum. Whore promises she'll cum right here if her master allows her. Please, master."

Rick looked directly into her eyes and said, "No. You do not have my permission to cum. You'll not touch yourself as well, no matter how much desire to do so you feel. After all your classes, you'll meet us in your office. Is that understood?"

Dejected and disappointed, Jessica said, "yes master. Your whore understands."

The entire day for Jessica was a nightmare. She felt too aroused to focus on her lectures or any other work. Her desire to cum clouded every aspect of her life. She had her last lecture of the day till 5PM and when it finished, she urgently rushed to her office. "Master will allow me to cum now. He'll allow me to cum now. Hurry. Rush. Fast. Cum. Oh. I'll finally cum..." thought Jessica while rushing to her office.

She opened the door in excitement but felt a sudden disappointment to find it empty. "Where's master?" she thought. The tingling and warmth from the gel had subsided by now, but her arousal was at its peak now. Only thing she needs is to cum. She waited in anticipation and then the door opened with Rick entering inside.

"Remove your dress and hair extensions and hand it over to me. Quick," ordered Rick.

In her excitement, she completely tore the dress off her body and removed her hair extensions in record time. Her brain couldn't process what she would wear to return home. All she needed was to obey her master so he would allow her desperate orgasm. He took both and threw it next to his feet. Next came out that miserable gel again. He generously applied the gel again on every sensitive spot.

"Climb up on the desk, kneel, legs wide spread and hands locked behind your head," ordered Rick.

"This is the time. My master will make me cum," thought Jessica and jumped on top of the desk instantly and took her position.

"Cock Hole," shouted Rick.

Jess instantly opened her mouth wide, aiming to please.

He took something from his pocket and held it up. It looked like some sort of gag, but had no straps. It had two vertical, rubber tipped posts either side, connecting the two posts top and bottom were two nylon coated bars that started off straight then formed semicircles. Protruding backwards from the two posts were nylon coated D rings to complete the mouth lock. Unbeknown to Jess, it was a mouth lock that had been picked to the correct size from the measurements Rick had taken previously.

He told her to open wider and tilted the mouth lock slightly up and at an angle as he inserted it into her mouth, popping the remaining D rind behind her lip so it was fully in her mouth. He then played with the lock until the semicircle sat behind her front teeth and the posts sat on her first molars. He then rotated both posts together, this then extended the gag causing her jaw to open even wider and locking the gag in place making it impossible for the gag to be spat out but forming the perfect and inviting hole to use and abuse as they wanted.

It didn't take long before saliva started to build up in her mouth and without the ability to close her mouth and swallow this soon pooled at the front of her mouth before slowly trickling over her lips and down her chin. The slow movement of the saliva down her chin was like water.

Rick brought out the zero vision contacts and ordered her to place them on. She removed her hands from the locked position and placed the contacts in place. No vision, mouth wide and hands again locked behind her head. This increased her arousal even further and the gel's effects also kicked in. Her juices were flowing freely, and her inner thighs were completely wet.

"You will remain in this position until I return and tell you to move from this position. I'll be watching you, so do not dare to touch yourself. Do you understand?"

"Yes, master," she tried to say, but it was just a noise.

"Nod your head if you understand fully, whore?" asked Rick.

She nodded to confirm.

Rick grabbed the dress and hair extensions and left the office. Jessica never heard the door close. This increased the fear and increased her excitement and arousal. She was struggling to keep her position because of her arousal. "What if someone comes up and watches me in this vulnerable position? I won't even see anyone. It can end my career," thought Jessica.

"I told you to shut the fuck up. I don't want to hear a word from you. You are a fucking cunt. My master punishes me because of you. Master loves me, but he hates you. I'm in control now and you'll do as I say. Even if the entire university crowds outside, I'll stay in this position, and you'll not say a word. Is that understood, you cunt?" Voice of the whore scared Jessica.

"Why are you doing this to me?" asked Jessica.

"Because I love every cock in every hole of my body that my master wants. I'm a true cum guzzling whore for my master. I will fuck and suck whoever and wherever my master wants. That is my destiny, and no one can stop me from fulfilling my destiny. Especially not you. If you come in my way, I will ruin you. Am I making myself clear, cunt?" The anger in the whore's voice was clear to Jessica.

"Crystal clear," responded Jessica to the whore's voice in her head.

When Rick left, it was 6:30PM and when Jessica heard someone walk around; it was 9PM. Jessica had been in her position for the past two and a half hours. Her arms and shoulders hurt because of holding them locked behind her head. Her knees hurt because of kneeling on the firm surface of the wooden desk. Her jaw ached from being open wide for so long and her tits were covered in spit and saliva. But the whore within wouldn't allow her any rest. Jessica managed the physical pain just fine, but the mental attack by the whore was too much for her confidence.