Teacher's Dilemma Ch. 09

This was an absolute humiliation for her, especially considering Phil's presence. She nervously looked around and found one person she had seen before. Only problem was she couldn't remember where. When he walked up to her and said, "how are you whore? Remember me?" Now she remembered he was the truck driver who had fucked her on the way to the farmhouse. She didn't know that Rick had exchanged numbers, and she was here to earn some money for Rick. He didn't dare to cross the orders from Rachael by making her fuck everyone, but found a loophole in her order. "Her throat is fair game," he thought. He had this arrangement for two grand. It's good cash for a student.

Rick handed the leash to the truck driver and sat down on a bar stool.

He brought her to the center of the bar with a group of folks surrounding her. On her knees, she received the second cock of the day deep in her throat. It was the truck driver, and he didn't let her settle down. One merciless push deep down her throat. Then began the stimulation from the gadgets again. Only this time, the stimulation was frustratingly mild. It would be enough to keep her on the edge, but wouldn't allow any relief.

Rick pulled his phone out to find seven missed calls from Jamie. He hadn't told him about this arrangement. "He's too weak and scared of Rachael. I would tell him after I reach back home," he thought. Calling him would be a worse idea and it would take a lot of effort making him understand the situation. So, he texted him:

Sorry buddy, I left early with the whore. Didn't have time to talk to you earlier. Claire can drive you home. You should also help her settle down in her new home. I'll see you later, directly at our whore's house.

After he sent the message, he got a few more calls from Jamie, which he ignored. Then finally he got the response in text:

What the fuck are you up to? This wasn't part of the plan.

Rick ignored this text as well. He saw the preview of the text but decided not to open it so he can claim the innocence of not reading the text. He knew iMessage will show him the receipt and it'll be hard to explain why he ignored the text message. "Just enjoy the party. He'll forget everything after he finds out about the money," he thought. He turned and saw Phil sitting next to him, but completely lost in the moment.

"Oh, fuck yeah. The whore has one heck of a throat. She's clamping her muscles around my rod," exclaimed the truck driver. There was a loud laughter mixed with a cheer from the crowd surrounding her.

"What would you say if I tell you folks, she's a teacher at my university?" shouted Rick.

"Hell no. I'd say you're lying. She can't be a teacher. I can't believe her to be anything other than a street hooker," replied one biker. He was a muscular black man and must be over fifty.

This crass response from this unknown man worked its magic on her. There were people consistently making comments to ridicule her. Someone said, "I can't believe anyone dumb enough to suck cocks in a place like this for money could have any sort of brains, let alone be able to work any other job. She's no teacher. I can guarantee that."

"I never asked for any money," thought Jessica, but then she realized Rick must have asked for money on her behalf. It was this realization that the whore took over completely and said to Jessica, "that's it. You've finally achieved your life's mission. Now you're officially a street whore. You've become me. I didn't make you do anything this time. You became a common street whore on your own. This is your destiny all along. I'm so proud of you, Jess. Or Professor Whore."

The driver pulled his cock out and jerked his entire load all over her face. Some of it dropped around her eyes, nose and some went into her hungry mouth. This extremely humiliating situation intensified her frustrated cunt, eager to cum at any moment. Her entire body shivered because of the level of control she had to display to not cum without permission.

This went on for an hour as each guy would fuck her throat with no care for her safety or her feelings. For them, she wasn't a human; she was just a hole for their relief. Some came directly inside her throat, filling her hungry stomach with their precious load, while some chose to cum on her body. They completely covered her face and the ridiculous dress with jizz.

Then came one guy who must be in mid-sixties and was definitely a homeless guy. She could smell the piss from his cock even though they had already plastered her face with their cum. He hadn't taken a shower in months. The thought of sucking his cock made her repulse and vomit. But she had no choice. As this guy started fucking her throat, the whore responded to her, "now you can never be a normal person. You're a worthless cumslut whore. Even a homeless guy is fucking your throat and I know you're enjoying every moment."

This moment made her lose her entire composure, and her moans and grunts echoed through the bar. It was so loud that people stopped talking. It was an unbelievable situation. There was an absolute silence in the bar, with only her moans and grunts echoing across the floor. They knew by now she was about to cum any moment. And as predicted, her control was over as she came hard. Her squirting fluids came around the edges of her chastity belt, covering her inner thighs.

The guy pulled his cock out, instantly fearing she might bite it while in her orgasmic euphoria. She was still in the middle of her massive orgasm when he added his load on her already covered face. It took her several minutes to recover from this massive orgasm. She surprised herself as she came hard, but still controlled her bladder. But now it was hurting her. Every man in the bar had their share of her, the homeless guy being the last person. And seeing her performance, everyone cheered and clapped while some whistled.

She looked around, which was difficult as they had plastered her eyelids as well with their cum. Jessica crawled slowly on her knees towards Rick and begged, "master, your whore's bladder is too full, and it hurts terribly. May your whore have the permission to relieve her bladder?"

Rick was waiting for this moment. He announced loudly, "guys, our whore here desperately needs to pee. And she agrees that if you all can collect an extra 500, she'll pee in front of everyone and exactly the way you guys decide. Let me know your decision."

There were many people in the bar, and he knew they were drunk and something like this was not something they would get to witness that often. So, it wasn't a big ask for them collectively. But for Jessica, this was a nightmare. She looked towards Phil and realized there's no respect in his eyes for her. She disgusted him. It shattered all her confidence. How can she ever talk to him professionally? He would never take her seriously now.

Soon, the truck driver returned with a bundle of fives, tens, and twenties. Handing the money to Rick he said, "we've another condition though. The bar owner contributed the most to this. He needs her dress as an exhibition for future customers, plus he wants to record everything to show it to them as proof. Let's just say it's for his marketing."

"Deal," replied Rick, putting the money in his pocket. He unlocked the lock for her dress from his phone, unbound her arms from behind. It took him a few minutes to remove the entire thing from her body and handed it over to the driver. He then sent it over to the bar owner. "I need a carry bag, though. These gadgets are precious, and I can't lose them," said Rick. When he got a plastic bag, he removed and placed all her gadgets in it. Once satisfied, he said, "she's all yours. She'll do exactly as you guys want from her."

The driver ordered her to stand and turn around. When she did, everyone saw her tattoos and piercings in its full glory. "This was money well spent," thought the driver. She followed him to another side of the bar, where there was a pool table. He ordered her to climb on the pool table and squat with legs wide open, granting full view to her soaking wet cunt. Reluctantly, she did as per her order. She was too desperate now.

The owner had his phone pointing right at her, recording her every move. "Open the lips with your finger so the camera gets a better view of your goods," said the bar owner. She used her index and middle finger to open her cunt lips. "And now you may pee," said the owner. Upon hearing the words, she let all her inhibitions out came the warm fluids on top of the pool table. She closed her eyes and imagined herself sitting in her bathroom and not in front of a bunch of strangers.

The owner captured every moment of her moan of relief. The pool table was completely wet from her piss, and it ruined the table. But it was too old, and his customers never really played the game. The money he would earn from the perverts that show up in his bar from the video and the promises of whores would be significantly more than the cost of this pool table.

When she finished peeing on the table, she opened her eyes and waited for her next instructions. "Now one last job. Masturbate for the camera and after you cum, you're free to go," said the owner.

Jessica just wanted to leave this awful place as soon as possible. She closed her eyes and began rubbing her clit. She was already hyper aroused, and it didn't take long for her to reach the edge of the orgasm. But something happened in her head. She controlled her orgasm. This was extremely weird. She had the permission to cum, but still her brain controlled the orgasm for the longest time possible. Controlling her orgasms had become her natural behavior now. She couldn't enjoy the orgasms if it came without a struggle. Finally, when she could no longer control, out came the liquid lava from her cunt onto the table, adding more fluids to it.

Her massive, squirting orgasm mesmerized everyone in the bar, including Phil. People rarely get to witness such an event. This was a gorgeous find for everyone. Few minutes later she stood naked outside the bar waiting for her master to unlock the car's door. The owner shook his hand and said, "she was way better than I ever imagined. If you wish to earn a lot more money, then we can make her a regular at the bar. I can give a monthly salary if she can perform every Saturday night. Think about it."

This was a great proposal for him. Who doesn't like extra cash? "I'll think about it and maybe we can negotiate," said Rick and turned towards the car.

Before leaving, he said to Phil, "what do you think about her now, Phil?"

"I'm absolutely disgusted by her. I couldn't believe that I ever considered her to be my peer. She was born to be a street whore, and that's where she belongs," replied Phil.

"Well, we'll see about that, Phil. Maybe that's her future, but for now she'll work at the university." And with that statement, he sat in the driver's seat and Jessica sat on the passenger side. Phil's last statement shattered Jessica's heart in several pieces. "Maybe he's right. I might just belong on the streets as a full-time whore. No professor ever behaves like me. I'm a worthless whore," she thought as tears started flowing freely again.

"You were wonderful back at the bar. So as a reward, you have my word no one will trouble you tonight and tomorrow. You can rest and recover completely. Sunday is a different story, though. There's something big planned for you on Sunday and I can't waive that off."

Jessica had mixed feelings about his statement. She'll get some rest, but then there's a fear of what's next for her on Sunday. Things keep getting worse for her each time they have some surprise for her. But then she can't worry about something she had no control over. So, she said meekly to him, "thank you, master." Rest of the ride back to home went uneventfully.

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Ray's Office (4^th February, Monday)

Claire walked up to the reception and asked, "I want to meet Ray. If you could help me talk to him, that'd be wonderful."

Woman behind the desk said, "Do you have a meeting setup with him?"

"No. But it's a five-minute thing. I'm sure he won't mind," replied Claire.

"That's not how it works, though."

"If you can, call him and say that Claire is waiting for him. It's urgent and concerns Jessica."

"Who's Jessica?"

"I'm not at liberty to say anything to you. But he knows both of us. If he denies, I'll leave. I promise."

She did as asked and then responded to her, "okay, follow me and I'll show you to his office."

Claire entered inside his office and saw Ray seated in his chair. Once she closed the door, he said, "I'm listening. And this better be worth my time."

"I'm here to give you an update and an offer. If you think it's worth your time, let me know otherwise I'll show myself out," she said in a confident voice. Claire had been a confident woman all her life. And she always knew how to climb the ladder of power upwards.

"Go on."

"I'll be honest with you first. You've made a mistake making Rick and Jamie full-time masters of Jess. They don't know what they're doing and often have a short-term tunnel vision. Take an example of Rick. He gets her ownership and makes money from her. It puts her in unnecessary danger and puts your long-term plans for her in jeopardy."

Before she could continue any further, he said in shock, "what? He's doing what now?"

"Yes, you heard it right. Even after he had the simple order from Rachael to give her rest till Sunday's event and then more rest till her club debut, he turned her into a common whore so he could earn some quick cash." She saw a sudden anger building inside him. "It's working," she thought.

"Fucking stupid asshole. If I want her to be a common whore, I won't need those two losers. There's a lot riding on her. To give her ample rest between her degradation was part of the grand plan. We don't want to push our toy to the breaking point," he said, clearly angry by now. He took a few deep breaths to calm himself down and said, "what's your proposal then? Make you take their position? How are you any different from them?"

"Yes, that was going to be my proposal, but not that simple though. I would suggest that you also move into her house. We can throw those idiot brothers out and we both control her. I know you don't have enough time to manage her mundane life. I'll take charge of that, but you can make major decisions and plans for her. I'll simply follow your plan. In return I want to be her primary mistress."

"And what do I get?"

"You get me. I'll be your girlfriend. I promise to fulfil all your wildest fantasies from your girlfriend."

Now this made him think. Claire was a young and gorgeous woman. Having her as a girlfriend would be a dream come true. "Think again. Are you sure? Can you keep up with your promise?"

"Yes, I'm 100% sure. I'll bring all your fantasies to reality. I just need your support in controlling Jessica."

"And why is Jessica so important to you? You barely know her. Why are you willing to put yourself in such a predicament for her?"

"It's all about power. I want absolute control over her and with Rick around, that can't happen. I'm not sure why, though. She's too addictive. I never had such a feeling about anyone before. There's this urge to become her mistress. I can't control this urge."

There's something different about Jessica. It looks like everyone had a powerful urge to control her. Claire reminds me of Steve. He also behaved similarly when he couldn't control her initially, thought Ray. "It won't be absolute control, though, and you won't ever be her primary owner. That spot has already been taken. But you can control her daily if it doesn't spoil our long-term plan for her. That's the best deal you'll ever get. Take it or leave it," he said.

"I accept the deal."

"Not so fast. First, let me check the goodies. Remove all your clothes. Crawl here and give me your best possible blowjob. If I like it, I'll accept the deal, otherwise forget it," said Ray. It was a power move to show her who's in charge here.

She didn't hesitate for a second and was soon under his table, completely naked. Claire was a skilled cocksucker, and it was clear with Ray's response. He couldn't control his moans. After a few minutes, he deposited his load deep in her belly. She swallowed every drop like it was the most delicious meal she's ever had.

Once dressed, she said, "so? Do we have a deal?"

"Yes, we have a deal. You're my girlfriend from now onwards. And if you're my girlfriend, you can be Jessica's mistress. The moment I breakup with you, you're out of her life as well. So better keep your boyfriend happy."

"Oh, I intend to keep my boyfriend happy forever. You do not know how wild your girlfriend can get. Bring your worst and I'll make them my best." And with that, she left his office. She was so excited now, like a kid got her birthday wish. "Now we'll see who's in charge, Rick," she thought.

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1^st February (Friday Night)

Rick parked the car in her garage, and both entered the house. Jamie and Claire were already waiting for them in the living room. Rick knew he had some explaining to do. "It would be best if Jessica is not around while they have some serious discussion," he thought. "Take a nice long shower. Get cleaned up," he ordered her. Jessica thanked him and left for the bathroom to get all traces of her filth washed away.

Once she left, Jaimie said, "you better have some explanation for your behavior. I'm not her Rick. You can't just ignore me."

"Come on Jamie. I never ignored you. You're my brother. Why would I ignore you? I was busy and couldn't look at my phone."

"Yeah, and I'm also your brother, so I know you too well. I know when you're busy and when you're ignoring me. And where were you so busy?"

"You would be so glad when I'll tell you where I was so busy. I was earning a lot of money for both of us. In a matter of a few hours, I made two and a half grands, Jamie," said Rick, excited and hoping this will make his brother happy as well.

"What the fuck did you do? You are a fucking moron. Rachael specifically said to give her ample amount of rest and you whored her out for some cash. You know that money isn't worth losing your life, right?"

"Come on, Jaimie. Stop being a pussy. Sometimes we need to take risks in life for some excitement. Otherwise, we'll regret the opportunities forever. I even had an offer for some steady monthly income here. We can really have some fun. Why do you have to ruin everything?"

"I have to ruin everything? You're the one who's jeopardizing everything just for small cash."

Claire chimed in to stop the escalating fight, "hey guys, whatever happened let's forget it and move on. There's no point arguing about something that has already happened and we can't change it. I propose once she returns from the shower. We all have some fun with her and forget this tension."

"No, that won't work. She really worked hard earning the extra cash for us and as a reward, I promised her she'll get full rest tonight and an entire day tomorrow," replied Rick.

"You promised her? You discussed nothing with us before making such a promise to her," said Claire in her frustration now. She was excessively excited to play with her toy tonight, and Rick's promise ruined everything for her.

"I don't need to discuss anything with you, Claire. Don't overestimate your worth here. You're here because Jaime asked me. Otherwise, I won't allow you anywhere near my whore," responded Rick in an angry voice.

Claire looked at Jaimie for support, but he would argue with Rick until he wasn't angry. Over years he had learned his lesson about not pushing Rick when he's angry. When she got no support from him, she said out loud, "you're going to let him talk to me like that, Jaimie?"