Teacher's Dilemma Ch. 10

Special thanks to "Ellie aka Worthless Whore" 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: Several things led to the delay of this chapter. I'm thankful to the patience of readers of this series. This is a huge chapter and might feel slower to some. But I needed a lot of contexts for this series to move into its next phase. All the open pieces of the series merge in this chapter. It was necessary to provide more explosive future chapters. All future chapters won't be this long.

Special Notes: I have intentionally dropped clues at each chapter. People paying attention might guess what could happen next.

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PART I (THE JUXTAPOSITION)

19 ^th August 1986

A Cadillac stopped outside a shady-looking neighborhood and a gorgeous blonde woman got out of the passenger seat. The driver counted the money and handed it to her. She placed the money inside her mini-skirt pocket and said, "I hope you and your friends had a wonderful time. Whenever you need me, I'll be here. Bye."

"Bye, darling. And yes, we loved each second our cocks rammed one of your holes. I'll contact you soon," said the driver and drove off.

Hanna Fischer took a deep breath and walked towards an old building, which was her brothel. She'll have to hand over all the hard-earned money to her pimp and he will decide what her cut would be. Hanna didn't care about the money. She wants to get away from all of this but has no choice.

As she gave all her money to Samuel Rivera, her pimp, he said, "that's all the money? Hide nothing from your master."

"Your whore would never dare to hide any money from her master. That's all the money I had, master," replied Hanna.

"Here, that's your cut," said Samuel, giving her $10. It was less than ten percent of what she gave him. But she knew there's no negotiation with him. She took the money and quietly left for her room. Hanna took a sigh of relief, realizing that her shift for the day was over.

Trisha introduced the idea of a ten-hour shift in this brothel. She convinced Samuel that providing proper rest to the whores would help in their mental and physical wellbeing. And this will help them be in their prime for a longer duration. She was the first whore in this brothel and had retired over five years ago. Samuel had tricked her into this world. Trisha was a black woman who had spent most of her adult life in this hellhole. Now at sixty-two, she became the mistress of all other whores. Samuel had given her the duty to manage and administer everyone. He didn't have enough time to keep track of all the whores. It was Trisha's responsibility to keep everyone in line.

There were thirty-two active whores in this brothel currently. But Trisha had genuine sympathy for only one, Hanna. It was one depressing night for Hanna when she confessed her entire life's story to Trisha.

How she grew up in an extremely conservative Catholic family in Germany. And fell in love with a visiting American business executive. He convinced her of her beauty and said, "if you'd agree to come with me to Hollywood, I'd make you a superstar. You're too gorgeous to waste your talents in a church." He kept planting this idea in her head until she agreed. But there was one problem. She didn't have a passport or any valid document to travel abroad. That man, she thought, who loved her, proposed another idea to travel. Betraying her entire family, she eloped with him and reached America illegally. This turned out to be her biggest mistake. On her nineteenth birthday, she saw his actual intentions. What proceeded from then onwards was a life of hell.

As Hanna told her story, she couldn't help herself from sobbing like a child. It was a deeply traumatic experience for her she had suppressed inside for far too long. Trisha always tried to pretend she was a hard ass in front of all the girls, but this was a story that hit her hard. She couldn't control her tears as well.

Hanna knocked on the door and heard Trisha's voice, "come in." She went inside and knelt in front of her bed. She said, "mistress, may I ask you for a big favor?"

"Go on. Tell me what you want?" said Trisha.

"He proposed to me today. It was exceedingly difficult for me to go to the private party after. I think I love him, but I fear Samuel a lot. While I'm here he'll continue to sell my body. Please help me, mistress," said Hanna in a serious voice.

"Roger?" asked Trisha.

"Yes mistress," replied Hanna.

"Samuel won't let you go. You're his top earning whore. He charges a lot for you because the demand was so high for you. Are you sure you want to do this?" asked Trisha.

"Yes, mistress. I'll do anything to leave this place. Please help me."

"Does he know everything about your past? The nasty things they made you do. And if yes, is he fine with everything? I don't want you to leave one hell and end up in another."

"No. I can't muster enough courage to tell him everything. But he told me he doesn't care much about my past."

"Men say that, so women will say yes to them. If later he finds out, he'll leave you. You should be upfront with him. If he's still fine with it, then take the risk."

"If I can live a few happy days in my life, I'd feel like I have achieved my life's goal. I don't want to die in this place, mistress. I'm ready to take any risk of having a chance of any life outside this place."

Hanna's last statement hit Trisha hard. The fear of what will happen to her if she runs away from this place was the main reason for her wasted life. "I never took the risk of leaving this place and now it's too late for me. But I'll help you get out of this hell. Promise me you'll make a good life for yourself," said Trisha.

"Yes, mistress. I promise."

"Sleep. I'll let you know about the plan later. But remember, you must run away to a faraway place from here and never return. You can't have any sort of life in this city."

"Thank you, mistress," she jumped and hugged Trisha. Both had tears in their eyes. It was an emotional moment for both. Hanna did not know that Trisha was taking a tremendous risk by helping her. She knew after Samuel found out about it; he'll make the rest of her life miserable. But she will take that risk. "My life is over. I'll die peacefully if I can improve her life," she thought.

Few days later, Trisha helped both Hanna and Roger flee the city. They went far away to Wyoming, where Roger got a job in the Black Thunder coal mine. Roger kept his promise and never probed about her past life. He took care of her. Couple of years later, they had twins, and it was the happiest moment of their life. What more could she ask from life? A girl and a boy. They named them Jessica and Michael. Occasionally Hanna would wonder about Trisha but never dared to pursue her thoughts. Few years later when she thought nothing bad could happen in her life, something terrible resurfaced from her past. It changed everything between her and Roger. Once, a loving husband couldn't hate her more.

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Present Year (11 ^th February, Monday)

School of Business (Lecture Hall)

Claire was living the sexual life of her dream. She never imagined herself as a submissive, but Ray brought it out. Master Ray kept her on the edge consistently. His unpredictable demands at random times were the best part of her new relationship. As a reward for her amazing performance, she would get full access to Jess only restriction was to follow the long-term plan. For Jessica, the most troublesome part was to follow Ray's orders. But she swallowed her pride and tried her best to not offend him. Ray was the person Jessica hated the most.

Claire kept reading the text message on her phone from her new boyfriend, nay her master. Each time she read it; a jolt of excitement flowed through her soaking wet pussy. Claire read it one last time before acting upon the instructions:

My Slut,

As you sit through your lecture, I want you to remember the essence of your master. Remove your panties and wipe my precious cum with it that must still drip out of your pussy. Roll it into a small ball and stuff it inside your mouth, my lovely cumslut. Next, you'll keep your legs spread wide open. I do not care if anyone sitting next to you would look down at my slut's pussy. For the entire duration of your lecture, you must rub your slutty clit till you reach the extreme edge. Stop and swallow the saliva mixed with your master's essence. Wait exactly one minute and repeat.

When the lecture is over, remove the nasty panty off your mouth and put it back on. This punishment will remind you to never question or doubt your master's command in the future.

Master Ray.

The lecture hall had comfortable individual seats with wooden foldaway writing tablets. There wasn't much scope to hide what she was about to do. To make matters worse, she sat at the center of the row of students. Claire looked first towards her right and saw her friend Olivia focused on the lecture. Without making a sound, she then turned to her left to find her close buddy Jacob taking notes from the lecture. "This is the right moment. Find your courage Claire and go for it," she thought.

She carefully lifted her ass a few inches above the seat and started rolling her panty down. Time slowed down for her. She took all her time. There was no point in rushing it and having an awkward conversation with her friends. If they grilled her about why, she thought it was a clever idea to remove her panties during a lecture with a room full of students. Once it reached below her knee, she sat down and looked at both sides to see if anyone noticed. Upon the realization that no one noticed, she looked forward and took a soft sigh of relief.

Her heart was racing several miles an hour. Both Jake and Olivia never knew about her kinky fantasies, and she intended to keep it that way. Now it was much easier to get the panty off with just the use of her legs. She kept looking forward, as if focused solely on the lecture. She closed her eyes, took a deep breath, and bent down as if to pick a dropped pen from the floor. This wasn't an effortless task, but determined Claire wouldn't give up.

As per the next instruction, she opened her legs and wiped any remains of his cum from her pussy and swiftly inserted the ball of her cotton panty inside her mouth. This time, she didn't dare to look either side. "They don't know. If they do, I can't look them in the eye," she thought.

It was now time to begin the next phase of her punishment. She opened her legs and began rubbing her clit. It was too risky and yet too exciting for her. The saliva kept building in her mouth, but it wasn't time to swallow it yet. As she reached closer to her much needed orgasm, it was getting even more difficult to suppress her moans. "Don't you dare make any noise," she kept reminding herself.

Claire stopped her fingers at the exact point of no return and swallowed. She could taste the deliciousness of her master. But there was a problem. Her breathing had intensified. It was impossible to control it. When she began the second round, she could see through her peripherals. Jake was looking down. "Now he knows," she thought. But something weird happened. Instead of stopping or closing her legs, she opened them further and increased the intensity of her fingers. "I can't look him in his eyes, but I can give him a show of his life," she thought.

It took her a lot of effort to control her breaths and not start panting in the middle of a lecture. She was sure by now that Jake was looking directly between her open legs and moist pussy. Claire went back to the thoughts of this morning's events that brought her to this shameful yet exhilarating punishment...

Last week was a crazy ride for Claire, especially last night. Master Ray had a lot of torturous fun with both cumsluts in the house. Of course, Jessica endured most of the mental humiliation, but Claire wasn't free from his psychotic kinks. In the morning, Claire woke up early and quietly left the bedroom, trying not to wake the devil up. Her plan was to get ready for university before he's up and have some fun with her slave on the way. Both women took shower together to save some time, but the main reason was for Claire to play with her toy.

By the time both were ready to leave, Jessica was already in a desperate need of her orgasm. Her libido had taken a sudden surge and the whore within her had become extremely addicted to those massive orgasms. Her immense hate towards Ray should have helped her in controlling her behavior. But it had the opposite effect on her. In just one week, he had made her an extreme nymphomaniac. His assertive commands would make her weak in her knees. It was like he had a magical spell on her. Which was obviously not true. He had played perfectly with her emotions and psychological traits.

Jessica knew Claire tried to show her brave face in front of her, but she was just as scared of him. So, when she quietly woke her up and whispered in her ears to leave for university earlier than usual, she didn't protest at all. It was a promising idea to dodge him. Claire opened the door, and they were about to leave the house when the demon voice came from behind them, "where do you both think you're going?"

"Fuck. He's up," thought Claire. She just needed some extra alone time with Jessica. She turned around and said in her sweetest voice, "our whore had an early morning work stuff. I thought I shouldn't disturb our master. So, I was quietly sneaking out with her." Everyone in the house knew she was lying. Her voice wasn't confident enough.

"Do you, whore? Have early morning stuff? You would know never to lie to your master, right?" said Ray in a soft but stern tone. He didn't raise his voice, but the words were threatening enough to weaken Jessica's knees. There was no way for her to lie. She just couldn't. Even if she wants to.

"No, master," replied Jessica meekly, with her head bowed down, looking directly at his feet.

"Would you like to clarify your lie?" said Ray, looking directly into Claire's eyes.

Claire thought to put the entire blame on Jessica and shouted, "so, you lied to me..."

Before she could finish her sentence, Ray interjected, "doubling down, huh? I guess I haven't taught you a moral lesson. Come inside, both of you." Scared of him, both instantly walked inside. "Remove your skirt and hand it over to me," ordered Ray to Claire. She didn't hesitate and followed the instructions. As per her normal orders, she wasn't wearing any underwear.

"Now let's begin the punishment," he continued. He grabbed her hand and brought her back towards the door. "I want your palms on the door and torso parallel to the floor. Elbows straight. Legs spread wide with straight knees. Eyes on the floor." She assumed the position as per the command. "You will remain in this position unless I say otherwise."

Turning towards Jessica he continued, "crawl between her legs and your tongue on her slutty cunt. I am going to take a long shower. Your job is to make her cum. She's no longer in command. So, you don't listen to whatever she says. If she ever takes revenge for today, then I'll let you own her for one full week. If you make her cum before I return, you win otherwise, she wins. And believe me, neither of you would want to lose."

Ray turned and left and from the far corner Claire heard his voice, "remember slut, do not move and do not cum."

Claire realized her own mistake. Few days earlier she gave a suggestion to Ray. The whore would look wonderful with her tongue pierced. Ray loved the idea. Next day he had her tongue pierced. Jessica hated all the body modifications that were done to her. This one felt brutal because it would be visible to everyone she met. And the piercing wasn't small either. It was a massive golden barbell pierced vertically on her tongue. The ball above her tongue was massive and couldn't be hidden if she talked. The bottom part was customized into a thick, massive ring rather than another ball. Those familiar special pills helped her tongue heal much faster.

Jessica instantly crawled between Claire's legs the moment she heard the shower. It was an uncomfortable position, but she grabbed her ass for better balance. In only a couple of minutes, Claire realized how skillful Jess had become, pleasing both men and women. Jessica's skilled tongue rocked her world to this euphoria of sexual heaven. The pierced ball on her tongue made matters worse for Claire. It was her intention to enjoy the oral from her slave, but this was not the time to enjoy her oral skills.

"Ah! Ah! Oh... fuck... please slow... oh my god! Please slow down... Ah..." yelled Claire at the top of her lungs. She didn't care if Jessica's neighbors heard her voice, and neither did Jessica. There was a rejuvenated strength in Jessica's mouth, and she showed Claire the training she had received over the past several months.

Claire's untrained cunt was no match for Jessica's tongue. "STOP NOW. Or I'll... Ah... fuck me..." and with that, she had one of the hardest orgasms of her life. Her body continued to shiver under the euphoria she had achieved, but to make matters worse, Jessica didn't stop or even slow down. Seconds later, she had another earth-shattering orgasm and then another and another. She now had a blurred vision, and her legs gave up. Jessica had to support her now to keep her position.

Claire had lost her strength to say anything. All words that came out of her mouth were an incoherent mumble. And yet, Jessica wouldn't show her any mercy. By the time Ray returned from his shower, Claire was a mess. She had at least eight back-to-back orgasms. Every inch of her body was hypersensitive to the touch.

"Stop," commanded Ray, and Jessica stopped instantly, as if a trained pet had received her command. "I can clearly see who won this battle. Tell me how many orgasms she had?" asked Ray to Jessica.

"I counted at least eight, master," replied Jessica.

"Hm. You didn't even try to win. As a punishment, you've lost your ticket to Professor Whore's club debut. You will return to your own place tonight until we return," Ray ordered.

Claire dropped to her knees and begged her master, "please master, have some mercy on your slut's first mistake. Please."

Ray knew that this was the right moment for a punishment for Claire, and he intended to go through with it. Over the past week, he had been very lenient with her. This is the time to show her who's the master of this house. "I have already told you what the punishment is. Now if you wish to stay in this house, you must agree to this punishment. Otherwise, leave now."

This was always the risk of the political power move she made to gain control of Jessica. Ray was always going to be the ultimate master of the house and he'll remind her of that whenever she goes out of line. "I am a fucking idiot to think I could control him," she thought, but said, "I understand, master."

"Perfect. Now let's go to the bedroom and have some fun, shall we?" asked Ray to Jessica. She simply nodded. Ray whispered something to Jessica, and she nodded again. Claire walked towards the bedroom, followed by Ray and Jessica.

Ray laid down on his back in the bed and ordered Claire to ride his cock. Claire started riding his cock gently at first, but then increased the tempo. Lost in her ecstasy, she didn't feel both her hands bound tightly behind her back. Claire tried to turn to look at what happened, but Ray ordered her to keep looking forward. When she felt the cold lube spread on her ass, everything became abundantly clear about what would happen next. She could only muster the courage to whisper, "please master. Your slut would never lie to her master again. Forgive her."