Teacher's Dilemma

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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Jessica was driving to meet Mike for her usual Sunday meetings. This was her first time since her miserable stay at Tyrone's mansion. She thought it would help her clear her head before her vacation was over and her life becomes miserable again. Her constant planning and consideration to trap Rachael had been a failure. She hadn't been able to come up with any solution. How could she interrogate her for something she doesn't know about? There must be a solution, she's just not able to find it.

She stood outside the door but couldn't knock for a few minutes. It's been so long, and her life had changed so much during this time. She felt somehow Mike could read her misery and ask uncomfortable questions. After a few deep breaths, she finally knocked on the door, hoping her face wasn't showing her sadness.

Mike opened the door and said, "finally I can see my lovely sis. You've been so damn busy I thought something's wrong. Is something wrong?"

Jessica walked inside, avoiding eye contact, and placed the food on the kitchen counter and said, "No. Why would you say something like that?"

"What's wrong Jess?"

"I told you nothing is wrong. Why would you get such an idea?"

"Because you're avoiding eye contact. You never do that. Plus, what's with this new hair color? Now quit your bullshit and tell me what's wrong? You've lost a lot of weight as well," said Mike. She felt better because she was at least wearing her hair extensions.

Jessica knew she won't be able to lie any longer, but she can't tell him the truth either. She'll have to make something up which would sound believable and closer to the truth. She turned and looked into Mike's eyes and said, "nothing much. I'm just upset at Jason. He's gone so long and it's the first time I've been away from him. I never thought I'd miss him this much. I don't want to burden you with this shit. I'm being silly here. He has to do his work, and it's going to be better for both of us." Jessica thought to avoid the questions about the sudden drastic changes to her physical appearance, hoping he won't probe more on it.

She was convincing enough that Mike believed her and said, "do you want me to go there and check on him? I can verify if he's cheating on you."

"Shut up Mike. I know my Jason would never do such a thing. Once he returns, he'll get a promotion and it will set both our lives."

"Okay, if you say so. Now let's see what you've got for breakfast." Mike skipped further questioning as he understood he was making her uncomfortable.

They both had breakfast and had a nice heartfelt chat after a long while. Mike suggested she take a walk with him. It was a pleasant weather for January. While walking in his neighborhood, Jessica realized she could ask for a suggestion from him, revealing nothing. She said, "Mike, I was wondering, how did you fetch so much information out of the Latino gang? I heard they never share too much information outside the community. You literally had information about the entire operation in depth."

Mike felt a little weird after hearing the question, since she had shown no interest in his past before. But he assumed she's trying to have a conversation, or she's genuinely curious. He said, "Everything depends on how you present yourself. It's all a game of psychological warfare. If you want any information from those people, you must be completely docile. They must believe that you're not a threat and you cannot be a threat to them. Bring their confidence nay overconfidence out. Even the elite warrior falls to overconfidence. Smartest of people make silly mistakes when they feel invincible."

He analyzed if she was paying attention and then continued, "I created such an environment around me they felt my absolute loyalty. Plus, they looked at me as a guy who wouldn't go against their command, no matter what happens. Which gave me an unfair advantage over them."

He looked at Jessica and realized she was too serious while listening to him. She was considering how she could implement a similar approach with Rachael. She'll have to make her feel like she's invincible around her. Mike again had the feeling that something's wrong. He asked, "don't lie to me Jess. What's wrong? I can feel it something's wrong, and it's not Jason. If someone is troubling you, let me know and I'll fix any problem for you."

Jessica knew she could trust him with her life, but the problem was caused because of him. She cannot tell him that. Mike will do something stupid to save her and lose his own life. This is now her own fight and she'll have to figure it out on her own. So, she said, "there's nothing wrong, and no one is troubling me, Mike. You worry a lot about me. Keep calm, enjoy the delightful walk, and have some fun."

Mike didn't believe her, but said nothing. He'll have to figure out what's going on in her life. But for now, he must let it go. When they reached back to his so-called apartment, they chatted some more. After dinner, Jessica said her goodbyes and left for her own home. This Sunday was fantastic for her. She felt better and was ready to fightback. "You're going down, Rachael. You just don't know it yet. I swear to god, I'll bring you down."

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Next Sunday was her last day off on vacation. She called Mike and canceled their meeting because of two reasons. First, he was getting on to her and she felt extremely vulnerable around him. Second, she needed to prepare for the week ahead. She had to prepare herself for what's coming her way. As she was going to her bed after dinner, she got a text message from her master.

I kept my word and didn't bother you for the rest of your vacation days. Now it's your turn. From tomorrow onwards, you must follow all rules. Including no clothes inside house rule. I will remove all your access to all the doors, windows, and wardrobes. You must remain in your waiting position to get access to your clothes. You'll get instructions for the day once you reach your office desk. And since you have an appointment with your psychiatrist, you'll get one more task after work.

Jessica had turned numb to these miseries. First time since her blackmail started, she felt confident and determined. "I will go through anything till I bring these monsters down. Give me your worse but remember I will have my vengeance," she thought. She reminded herself, "Until that moment comes, I'll have to be the most submissive slave. They need to believe that they hold all cards but when it's my time, they'll not even see it coming." She discarded the clothes she was wearing. Her thought was to get into her routine from tonight.

Monday morning, she followed her routine that her master had always commanded her to follow. After taking the shower and applying all the lotions, she looked at her reflection in the mirror. She felt something she always hated herself for over the last few weeks, arousal. Her hairless and artistic body just looked too exotic.

"Why are you such a whore? They did so many horrible things to you and you still can't control your libido. Please pull yourself together. If you continue losing control over your own body, there's no way to win this war," she reinforced the motivational words in her head.

"But when those monsters don't allow me to cum for an extended period, there's no way for me to think straight. They force me to a point where I want nothing more than my orgasms. They know exactly how to play me like a piano. What is wrong with me? I can lie to anybody, but deep down I know when they're playing me, I have no control. I was a born whore slave. They just brought my whore out in the open," she hallucinated her reflection, saying back to her.

"No. No, I'm not a whore. I don't have a choice. I must do what they command, but I don't want to do it," she said out loud, this time trying to suppress the voice of the reflection. "I'm going insane. I need to fix this situation as fast as possible," she thought.

After wearing her hair extensions and the six inches black heels, she left her house. She had to stand in her waiting position for ten minutes before the metal box unlocked. Jessica rushed towards the box to grab her clothes. At the top she saw an envelope with text written outside,

Professor whore, read before proceeding.

Jessica picked the letter and nervously opened it. The letter read:

To Professor Whore,

This box has the dress for today, along with some important items as well. First open the black box and carefully attach the nano chips in all your piercings as I've instructed to you before. Then use the lube and insert your favorite black dildo all the way up your asshole. Next, insert all familiar balls in your cunt. Then you can wear your dress.

Today you've just two lectures. Those two lectures are going to be the most difficult lectures in your life. You have my full permission to cum as much as you want while you're giving your lecture, and there's at least one student in the room. My aim is to make you cum in front of everyone. You can hold it if possible. Since you'd not want to cum with all your students present (as everyone knows what a gusher our whore is), I'll give you a choice.

The moment you feel it's impossible to control, you'll have to open one button of your blouse. Each button gives you five minutes of rest. Remember, any button once open, you cannot close it again for the rest of the day. So, you'll have to be cautious to open buttons.

If you skip those lectures for any reason, punishment would be so severe that you'll regret it for the rest of your life. Best of luck.

Your generous master.

Jessica threw the letter back inside the metal box and started working towards her instructions. She quickly placed all the nano-chips on all her piercings as they were magnetic it took little time. Next, she grabbed that giant black cock and applied generous lube on it. After applying even more lube inside her asshole, she inserted the monstrous dildo all the way up her ass. By now, her juices had already started flowing from her cunt. "Why am I such a whore?" she mumbled in frustration. She inserted all four balls up her cunt and took deep breaths to calm herself down.

Then she grabbed the red satin, silk buttoned shirt and searched for a bra inside the box. There was no underwear available inside the box. She sighed and mumbled, "this is going to be extremely difficult." After she had the shirt on, she felt a little better as the buttons cover the burning flames tattoo above her tits completely. But if she opens a few buttons, the tattoo will be available for display. Next, she grabbed the black professional skirt. Once in place, it was a few inches above her knees. So, her dress covered all her tattoos.

Fortunately, her shirt was tight on her waist but had a little wiggle room on her tits. While walking, her tits would bounce freely, but her pierced nipples were not pronounced to casual eyes. You'll have to focus intensely on her nipples to see it. Before leaving, she tried opening her shirt buttons to analyze how much wiggle room she has for the day. Only two buttons could hide her tattoos, that too with utter care. Third button and it would be impossible to hide the flames. She made a note in her head to perfect her timing and limit herself to the maximum of one button per lecture. "This is going to be the most shameful lectures of my life. God help me. Give me strength to control myself for those two hours," she thought. Jessica knows she cannot cum in front of her students in any condition. "Let's go whore," she surprised herself when she mumbled those words, "why would I call myself that word when I'm alone? They're getting into my head. I need to be cautious of how I act when I'm alone."

While driving her way towards the university, Jessica felt extremely nervous. It was like the first day at school when she was a kid. It's been a long vacation for her, and her life had turned upside down meanwhile. She tried to focus all her energy on her plan for vengeance, but the butterflies in her tummy won't go away. She parked her car at her assigned spot and took a deep breath and said to herself, "you can do it. Believe in yourself. You can get through it. Just focus on the plan," and she left the car towards her office.

As she opened the door of her office, she saw both Jamie and Rick sitting already. Rick spoke first. "It's really nice to see our professor whore after a long time. How're you doing, prof?" She bowed her head in shame and fear. Jessica somehow expected to be troubled only during her lectures, but now she realized there's no limit for them. They're going to make sure she had her massive orgasm in front of her students. Jessica knows that if she came while in her class, she wouldn't be able to hold those balls inside her cunt. Dropping those giant balls during a lecture would be absolutely humiliating and potentially career ending.

"Your whore slave is fine, master," replied Jessica in a soft, submissive tone.

With a big grin on his face Rick said, "close the door, drop that purse and crawl towards your master."

Jessica followed the instructions and was kneeling in front of Rick as he himself sat in her chair. While patting her head like a pet, he said, "you must have known by now that your mistress Rose can no longer train you. So, both me and Jamie will move in with you full-time to keep you comfortable and update your daily training schedule." She looked up, shocked. "Aww! Our whore didn't know about her mistress being fired from her position. Well, we'll make sure she won't miss her mistress at all," said Rick while holding her chin in a childish voice.

"Now be a darling and remove your clothes and give it to your lovely master," ordered Jamie from the other end while setting up his notorious camera on the tripod. She stood up and followed their instructions. Now standing completely naked (except the heels) and her clothes in Rick's hands. He opened her desk drawer, placed the clothes carefully inside. And locked it. Placing the key in his pocket, he stood up and went behind the camera frame.

"Hop on top of the desk, on your knees, legs spread wide," commanded Rick.

She already knew this position as she had done it before. Once in the position needed, he told her to drink two bottles of 16-oz water they had conveniently placed on her desk. Jessica followed the instructions easily, as she had gained the ability to drink a sizeable amount of water in a brief span of time. Then to her misery Jamie pressed the button and all the nano-chips on her piercings came to life along with the intense vibrations in her cunt and asshole. She sighed instantly, followed by clear and audible moans.

"Lock your hands behind your head, back straight and offer your tits," came to next command from Jamie. With no hesitation, Jessica followed the command. For next few minutes, both brothers kept looking at her like watching a live porn sequence without a word. Once they realized she was on the edge of her much-needed orgasm, Rick said, "do you want to say something whore?"

Through her heavy panting she said, "yes. Master, your whore slave needs permission to cum. Please master, let your whore cum."

"You can't control your whore cunt for only a few minutes how are you going to control yourself during the lectures. Tell you what, if you agree to not control your orgasms during your lectures, I'll let you cum now. Do you want to cum now?" said Rick in a very cocky tone.

"Um... oh... ah... fuck..." all these masterful devices from hell were breaking her will. Jessica's ass already started moving like she was yearning to fuck an imaginary cock. She had closed her eyes and found it impossible to find her control. "Please... master... fuck... cum... whore can't cum... ah... fuck this whore... your whore can't cum in front of her students, please have some mercy on your humble slave," she said the last words forcing herself to gain some control while still dry humping.

"Then, unfortunately, I can't allow you to cum now as well. Jamie would be in your first lecture, and I would be in your second. Tyrone had given us a challenge. Whoever makes you cum in front of everyone first gets exclusive ownership of you. Which means the winner can do whatever he wishes to you for a week with no restrictions. I would love to own you completely for a week."

Jessica heard the terrifying words but couldn't remove her mind from the desperation to let go. The stimulations were too much for her. They specifically designed these artificial gadgets for extreme pleasure. Jessica had successfully controlled herself and denied her orgasms for an extended period, but these nano-chips were not on for a longer duration. The vibrating balls, anal dildo and the stimulating nano-chips combined were too much for anyone. Her entire body sexually alive and desperately screaming for release.

Rick continued, "but since Jamie had an advantage to go first, I don't think I'll get my chance at all. Since you're allowed to cum as much as you want during your lectures and limited buttons to open, we must come up with something interesting. We'll not have the stimulations on for the entire duration, but set to randomize. We'll have no control over it. The algorithm will make sure you have your massive orgasm in front of everyone. Also, it'll be fair to both as it'll be luck and the unpredictability will create more excitement in you."

Jamie, from behind the camera, recording her sexual peak, said, "now the algorithm itself can make you cum in the first lecture so we came up with a solution to that as well. As you know, opening a button gives you five minutes during which we'll pause the algorithm. But we generously added another lifeline for you. There'll be twelve 16-oz water bottles on the desk in front of you. After finishing each bottle during the lecture will grant you a two-and-a-half-minute rest. One caveat to it is that you cannot pee until after your appointment with Rachael."

Jessica was already struggling to hold her orgasm, and she knows controlling orgasms with the need to pee will be exponentially difficult from her earlier experience. If they would let her cum right now, she'll feel better for her task later. She begged again, "please master, let your whore cum. She'll do anything her master wishes. It's... fuck... too... much for your... whore... God... oh... oh.... Ah..." Her verbal nastiness came out in time of desperation. She had completely forgotten about her plan for revenge. Nothing mattered more for her than the need to cum.

"Anything?" asked Jamie.

"Yes... Yes... Oh God... Yes... Whore will do... ANYTHING... AH..." her excitement increased multiple folds after seeing a window of hope.

"As per your deal, you already have a task after work because of your appointment with Rachael. Are you sure you want another deal on top of it? Your day will become extremely hectic and if you made any excuses after the deal, we won't allow it," said Jamie.