Teacher's Dilemma Ch. 10

He turned towards her and slurred, "huh? You know me?"

"Uncle Roger, it's me. Rachael," she saw in his face that he still doesn't recognize her. "Your niece. I'm Amanda's daughter."

And then his face brightened up as he remembered her. "Oh yes. Rachael. Oh, you're all grown up now. I'm so sorry I never checked up on you. Your mother was such a bitch, she threw me out. I mean, I was her younger brother. But I swore that day that I'll never see her again. How is she anyway?"

Rachael paused for a few seconds and replied, "she's dead. Both dead."

"I'm so sorry. When?"

"It's been a while now. I think I was six when they died. I have grown up in orphanages since then."

Roger couldn't respond to her for a few minutes. Then he finally said, "I should have kept in touch with you. I'm so sorry that you had to grow up in an orphanage when you had your uncle Roger. But honestly, I was dealing with a nightmare of life myself."

"It's alright. You didn't know. I had no way to contact you as well. I can see you're suffering in your life as well. I can help. You can come to my house."

"No. I can't burden you. I wasn't in your life when you needed me. I can't magically show up when you no longer need me."

"You are my only family uncle. Who said I don't need you? I need someone in my life who I can call family."

They argued for a while, but he finally gave up and left with his niece. A random lucky day changed his life again.

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Present Year (13 ^th February, Wednesday)

Roger shook his head in disgust while looking at Jessica. "Remember I told you, if you choose her, you'll end up like her. A whore!"

Jessica tried to bow her head down in shame but couldn't because the ponytail was bound to her arms. There was no other way to get away from this nightmare. She shut her eyes, trying to avoid the gaze of her father when she's at her lowest and most shameful situation.

"Open your fucking eyes and look at me when I'm talking to you," yelled Roger at her.

Jessica opened her eyes out of fear of the unknown. She did not know what could happen to her on this island if she disobeys these people.

"Now tell me, was I right?"

"No. Mom had nothing to do with any of this. I did nothing immoral till she was alive. I was blackmailed and trapped into all of this. Mom always raised us right," she replied.

"And yet you are a whore and Mike is in prison. Who wants the mother of the year award now?" he said with a smirk on his face.

"You were never at fault, dad. It was always her mistake. Trying to keep up with a drunk and angry bastard who would leave no opportunity to abuse his family. Everything was her fault, right dad? You were a saint, and she was a monster." She could see that she had hit the right nerve in him. His face was a dark shade of red and ready to burst out in anger. She was too familiar with this expression. Roger did not appreciate the sarcasm in her voice.

But something was new this time. Instead of lashing out, he closed his eyes and took several deep breaths. She had never witnessed him trying to control his anger. It was like someone had trained him how to control his anger. "Rachael," she thought.

Roger raised his right hand and snapped his fingers. It was a signal to move the gadgets to the next phase. Suddenly everything came back to life with an exponentially higher intensity than earlier she had experienced. Roger stepped back and comfortably sat back on the sofa chair in front of her. He said nothing for the next several minutes and continued watching her torment.

"Ah... Ah... Ah... Fuck... Oh... Oh..." she couldn't control her loud moans and groans now. It was too much. She tried her best to remain silent, but it was impossible now. It was the most erotic sequence witnessed by everyone, including Roger. When this time everything stopped, Jessica had tears in her eyes. She couldn't take another edge. It was too much and too intense. But she wouldn't give up and beg her own father for an orgasm. But after another round of torture, she realized it would not end until she begged him. Each round was getting much more intense for her. She closed her eyes and tears began rolling down as the realization hit her. She's defeated.

"Please," she whispered.

"You said something?" asked Roger in a loud and clear voice. He had a smile on his face at the realization that she's broken now.

"Please," she said in a much louder voice.

"Please what?"

"Please, let me..." still at the peak of her desperation, she couldn't muster enough courage to speak such words to her own father.

"You must speak louder and clearer about what exactly you want."

"Please let me cum!" she yelled at the top of her lungs. There was desperation, frustration, and anger in her voice. She recognized her defeat but couldn't let go of her anger towards her father.

"Beg. Beg nicely and I might consider."

She opened her eyes and stared at him for several seconds. If there was a way to kill someone with a stare, she would have done it right now. But when she saw a giant smirk on his face, she realized there was no remorse in him. He has gone too far now. This man was no longer her father. This man was filled with rage, hatred, vengeance. Vengeance about something wrong done to him. But he was completely ignorant about what he had done to his family. There was no point in trying to explain anything to him. She finally surrendered.

"Please let me cum. I desperately need to cum. I beg you, please let me cum." Her voice was much softer now.

"I'm sure you can do better than that."

She was reaching another intense edge and knew these gadgets were about to stop. There was a small window to beg correctly. Only way to successfully do it was for her to assume that this man was another of her ruthless masters. "This man is no longer your father. He's one of your tormenting masters," she reminded herself.

"Please master. Please grant your humble slave whore the permission to cum. Master, please. Your slave begs you. Please." This time, her voice was much more convincing. She was too desperate now.

Roger smiled, stood up, and walked up to her. "Now we've reached somewhere. I have a few questions for you. If I like your answers, then I might grant you permission to cum. Nod if you understand, whore." Jessica nodded.

"First one, what is your name?"

"Jessica Peterson," she replied with an urgency.

"I will not repeat. Honest answers. What is your name?"

She knew what he was expecting. There's no going back. Her urgency was building faster with each passing second. "My name is Professor Whore, master."

"Correct. What are you?"

"I'm a worthless whore meant for the sole pleasure and entertainment of her masters."

"Perfect. You're doing well. Don't lose your streak. Who's responsible for your life's mess?"

Jessica knew exactly what he was expecting as an answer. Despite that, it was too difficult for her to defame her dead mother. She remained silent.

"I'm asking for the last time. Who's responsible for your life's mess?"

She began crying profusely this time. It was like every fiber of her being had been shattered into a million pieces. She was broken both mentally and physically as she responds between her sobs, "my mother, master."

"It takes a lot of time to find the true culprit, doesn't it? Now the last question: what was your mother?"

Completely shattered and nothing left for her to sustain and a bit of decency, she responded, "a whore."

"Well done. You may cum now, whore."

She no longer wants to cum. All her emotions were being crushed by this man. But physically, she couldn't control anymore. A massive, earth-shattering orgasm consumed her entire being as she yelled too loud in her own frustrations while crying through it. This was too much for her. A complete emotional and physical exhaustion. She passed out.

She woke up on the bed in the same room. Rachael sat next to her. "You did well for the first night on the island," said Rachael with a smile on her face.

"May I ask a question, mistress?"

"No, you may not," said Rachael, knowing exactly what her question would be. "There's food on the table next to your bed. Eat and take a good night's sleep. You would need rest for tomorrow. It's a big day for you, whore. Don't let your mistress down."

With that, Rachael left the room without giving her a chance to speak back to her. Jessica sat up with the question still lingering in her head. "How does she know my father? What does he have to do with all of this?" She must find answers to these questions anyhow if she wants to get out of this mess.

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September 2015

Rachael had worked hard on Roger to bring him out of his psychological darkness. Several simulated situations were created for him to control his anger through a special breathing technique. And worked towards his addiction. He had sobered up for over two years. It was a lot of work, but she felt proud of her work. Internally, she felt like she was helping her father. Only if she saved him.

After everything, she noticed him depressed again. Upon further questioning, he revealed his curiosity about the life of his daughter. He was worried that his ex-wife had already ruined her life. There was no way of knowing it because he did not know where they were. To cheer him up, Rachael told him she can find out about his family in a few days. She had a lot of resources at her disposal which ordinary people don't have.

Few days later, she returned with all the details about his family. Rachael entered inside the room excited and said, "I told you I can find everything about your family. I have all the details."

"Tell me how my Jessica is?" asked Roger with a level of curiosity in his voice.

"I'll tell you about everyone. But you must promise me you'll handle everything well. There is some good news and some bad news."

"Yes, I promise I'll handle everything well. Please tell me now."

"Bad news first. Your wife passed away from cancer a couple of years ago. Mike works for a Latino gang in the city." as she was telling him the bad news, there was no visible change of expressions in his face. It was like he didn't care about them at all.

"Tell me about my Jess. I don't care about those two at all," he responded with clear irritation.

"That's the good news. She's doing fantastic. Finished her PhD in physics and worked as a professor at the same university and married to her childhood boyfriend. Her now husband is also doing well in his life. You should be proud of your daughter. Your ex-wife raised an amazing and talented young woman."

Rachael's last statement brought some harsh reality to him. He didn't have expressions of joy or pride. In fact, he started crying like a child. Initially, she thought he had the tears of joy but soon realized they weren't. "What happened? I thought you would be glad to hear the success story of your daughter," said Rachael.

"It was me all along. I was the one holding them back. I kept this lie in my head that Hanna was the reason everyone hated me. But no. After I left, their life became much better. My Jess became successful after I left. I'm a terrible human. I was a terrible father," he said while crying. He continued his depressed rant. It had reached again to where he sounded like suicidal.

Rachael had to do something. Roger was her last family member. She can't fail him. "What do you mean, then? If her life was terrible, would you be happier?"

"No. I didn't say that. I always thought that if she chose Hanna over me, she'd eventually turn up a..." he paused for a second, unable to say the words but then continued, "a... whore like her mother. In fact, those were my exact last words to her. My last words to my daughter were a warning. I was wrong."

"I'm sorry things didn't turn out the way you expected. I thought I could help you. But I'm not your blood. You obviously care more about your own daughter more," said Rachael. She felt extreme jealousy at that moment. Even after trying so hard, she didn't have what Jessica had. A father. She thought after giving everything to him, he would appreciate her more. In her mind, he was the father figure she always craved.

Roger turned towards her and said, "it's not like that, Rachael. I'm not sad because of her. I'm sad because I was wrong all along. She's not my daughter anymore. The day she chose her over me, it was over. In my darkest time, you were there to support me. You are my daughter, Rachael. She just has my DNA, and it doesn't matter. In a weird way, if you would have told me I was right all along, maybe I would have felt better."

Under ideal circumstances, she would have tried to diagnose this person with some sort of mental disorder. But right now, she has her own bias. She had her own needs. If she could make his last words a reality, everything could become perfect.

"My sources did the basic research on her because we weren't looking into her personal life. It's possible that if we do a deeper dive in her life, things could turn out differently," she said to him.

"How would you do that?"

"By going closer to her. I can take a job at her university and get closer to her. Even try to be a friend. Girls tell everything to their friends. It's possible that you were right all along, but we just don't know it yet."

"You would do that for me?"

"Of course. I'm your daughter, after all."

"Yes, you are," he said in excitement and hugged her.

"It'll take some time, but I'm sure I can find her deepest and darkest secrets," she whispered in his ears. She did not know what she would achieve. This one decision changed the course of her life. A woman who would create an empire of money and absolute power. And ruin Jessica's life completely.

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14 ^th February (Present Year)

Jessica woke up late in the morning. The level of disgusting emotions she felt were overwhelming for her. She thought, "keep your eyes closed Jess. You're not ready for this horrible world yet." Everyone was plotting against her. There were no visible allies near her sight. How long can she hold on? "Was he right? Was I born to be a whore? If not, then why do I cum like a worthless street whore every time I'm forced into such humiliation? Why am I always so desperate for orgasms? No matter how hard I try, in the end I always end up begging for permission to cum. If this is not a typical behavior of a whore, then what is?" The questions kept getting worse by the minute in her head. It affirmed the belief that she was born to be a whore.

The intelligent and sophisticated woman felt lost somewhere in this whoredom. Her will to open her eyes and face this cruel world was lost. She pretends to sleep more and assumes that they'll leave her alone. But she knew it never works that way. Soon, her tormentors will enter and make her life much more miserable. She heard the door open and someone walking towards her. Jessica kept her eyes closed, still pretending.

"Well, don't tell me Professor Whore is still sleeping. Come on now, get up. It's time. It's your big day. You don't want to be late today. Up now," commanded Rachael.

Jessica knew there was no way out of this. She finally opened her eyes and pretended to rub them as if she's having difficulty waking up.

"Good morning, whore."

"Good morning, mistress," replied Jessica in almost a whisper.

"Now let's begin the big day. Get up and go freshen up. The bathroom is that way," said Rachael, pointing towards the bathroom. "I'll be back in thirty minutes. When I return, I want you cleaned with the whore makeup kneeling right here facing the door and hands locked behind your head. When the door opens, I want my whore to be the first thing in my sight. If that doesn't happen, then you're in trouble. Punishments here are unimaginable. Let's just say you don't want to be punished here. Your time starts now." With that, Rachael stood up and left the room. Jessica didn't have time to process anything, so she rushed towards the bathroom instantly.

She did her morning ritual as fast as possible for her. Finally, with a quick shower and her now well-practiced whore makeup, she rushed towards her designated spot. She looked at the wall clock and took a deep breath as there were less than two minutes left. Wasting no time, she took her position and waited for the mistress. The door opened and Rachael walked in, followed by three strangers. One woman and two men. All were naked and had black collars with leashes attached. "They all must be slaves like me," she thought. The woman was white. With her 5'6" height, she was much smaller than Jessica. The common aspect was their tits. This woman also had D cups which jiggled with every step she took towards her. As she got closer, Jessica noticed her eyes were also deep blue and was blonde. She had a tray in her hands, which must be the breakfast for her.

Both men were black. One was 6'4" while the other was 5'11". As per the stereotype, both were well hung. When she looked at their flaccid cocks, the first thought in her head was, "they must be at least 11 inches when in their full glory."

The woman placed the tray in front of Jessica on the floor. As expected, it was food for her. All three slaves went behind Jessica and took a similar position as Jessica. Anyone witnessing the sequence would instantly know who the mistress in the room was.

"Eat the breakfast and then they'll help you prepare for the rest of the day. Keep this," said Rachael, handing her a folded piece of paper. Jessica opened the note, and it had a lot of words written on it. She couldn't hold her curiosity and asked, "what is this, mistress?"

"They are your vows. Don't worry, my other slaves will help you remember the vows properly before you leave this room," replied Rachael with a giant smirk on her face.

"But vows for what, mistress?"

"Wedding vows, stupid. You're going to get married to your Master Ray as part of your club initiation ceremony," said Rachael in a matter-of-fact way.

"Married to Ray?" she thought, and cringed within. "But mistress, your whore is already married," said Jessica.

"Not on this island."

"But mistress, legally, your whore can't marry twice," said Jessica, trying to come up with excuses to avoid this cringe fest.

"Don't put stress on your little dumb head about the legality of things. Since when have we done things legally?" said Rachael with a rhetorical question at the end.

"But mistress..."

"Stop." Yelled Rachael, stopping her words with clear irritation in her voice. "It wasn't a choice. I didn't make a request. I said what's going to happen. Now do as they say and be prepared for the ceremony. It's very important. A lot of high-profile visitors will join the ceremony. A slightest mistake will cause compounded punishments. Don't take it lightly. I want perfection and you'll give it to me." With those last angry words, she turned and left the room.

Jessica turned back to look at the strangers who now stood up. The woman said, "first things first. Give me your wedding ring."

"What?"

"Your wedding ring. Give it to me," she replied, but this time with a more commanding tone.

"Please don't take my ring. This is the last shred of link left between me and my husband," begged Jessica.

"It wasn't a request. We'll take the ring. It's better if you give it on your own."

"Please, I can't."

"Okay, let's take it from her then," she said to the men in the room.

Both men pinned her down and twisted her arm behind her back. Jessica tried her last attempt by tightly forming a fist. The woman also joined in the efforts to remove the ring. Jessica tried her best, but the collective power of these three people was too much for her. After a significant effort, the ring was now off her finger.