Teacher's Dilemma Ch. 08

She felt a hand on her shoulder, and it startled her. The hand helped her lie down on the desk with the support of her elbows. Jessica hoped this was Rick or Jamie and not some random guy from university, but the whore didn't give a shit. She only needs her pleasure. Then she felt a massive rubber cock pushed deep in her throat, she struggled with her gag reflex at the sudden intrusion but couldn't do anything with the mouth lock in place. After assaulting her mouth and throat for some time, the mouthlock was removed from her jaw. Rick close by her then said "your throat will get used more than that at the club bitch, so you better get used to it"

The massive rubber cock that had assaulted her throat was now pushed deep in her soaking wet cunt in a single thrust. Jessica gasped and said, "thank you, master."

"Don't you dare cum without permission whore." She heard Rick's voice now from the corner of the room.

"Who's this man? I hope he's Jamie, please," thought Jessica but was instantly interrupted by the whore, "shut up. I don't care who's fucking my cunt. I love it."

"Yes, master. Your whore will not cum," replied Jessica.

Then began the rhythmic penetration of the massive rubber cock going in and out. The whore within her couldn't control now and yelled out loud with no fear of the crowd gathering outside her office, "Ah... Ah... Ah... so good... feels so good... I'm going to... cum... soon... yes... oh... yes.... Stop... please master, stop... whore will cum.... Stop, please..." and then suddenly the cock left her cunt, leaving the feeling of emptiness and even more heightened arousal.

They gave her a rest for a few minutes and then it started again. They brought her to an extreme edge of orgasm and then stopped. Now there was no Jessica left. It was a hundred percent whore. And she needs to cum desperately. After five iterations of that torturous denial, the whore gave up and begged, "please master. Let your whore cum. Your whore will do anything her master desires. Please let the whore cum master. Please, no more. She can't handle this anymore. The whore begs you master. Let her cum. Please."

She kept on with her begging and then heard the command, "stop with the begging now." Her submissive side kicked in and she stopped speaking. "I want you to remove those contacts from your eyes now," commanded Rick.

Jessica sat up on her knees and removed the zero vision contacts. The moment she removed the contacts and adjusted her eyes to the light in the room, she saw Jamie recording everything with his infamous camera and Rick sitting in the room's corner, along with Steve. She turned to the side and saw Ray holding the dildo with a suction cup in his hand. When she saw Ray, Jessica came back up. "He's responsible for everything and now he enjoys my suffering," she thought in her absolute anger. But didn't dare to say anything.

Ray ordered her to sit a few inches back on the desk. She followed and moved backwards on the desk. Right in front of her, he placed the dildo with its suction cup set on the desk. Rick brought a pile of documents and set them in front of her on the desk.

"You're going to ride that cock with your hands locked behind your head. As you're on the absolute edge, you'll beg us to allow you off the big fake cock. Once we allow you to get off it, you'll instantly grab this pen and sign one document. As the document is signed, you'll ride the cock again. Once all documents are signed, we may allow you to cum. Otherwise you cannot cum. Is that understood?" ordered Ray.

"What are these documents? I haven't even read them. I should ask them what they are," thought Jessica, but as usual the whore picked her thought and yelled at her, "how many times should I tell you to shut the fuck up. You will sign every document on the desk. I don't care if the documents grant all your assets to them, you will sign the documents. Is that understood, cunt?" Jessica again gave up and agreed to Ray's terms.

She rode the fake cock, and her soaking wet cunt took it all in one smooth motion. Her frustration and arousal were so high that she couldn't control the nasty talk any longer. "Ah... Oh... my god... whore loves it... master your whore loves it... your whore deserves everything that her master gives her... The whore needs to be humiliated by her master and his friends. The whore needs to be fucked by everyone. Her master and all his friends must degrade her if they desire. Ah... fuck... master, the whore is about to cum... may the whore sign?"

Her body started shaking and shivering because of the extreme control she had to put to control her orgasm. "Sign whore," ordered Ray. She instantly hopped off the cock and looked at the document. It had a lot of words written on top of it, but she wasn't in any condition to read them. She just held the pen and signed on it.

Jessica's vision got blurry because of the extreme need and frustration. She had signed six documents so far and there were still a bunch left. Some documents were application forms with her photo on them, but she couldn't read what they were. Her entire body was hypersensitive. Every thirty seconds she would reach to the edge and then sign another document. Each cycle of control was getting harder.

After countless documents were signed, she saw Rick picking the pile up and sat back at the corner. Jessica continued riding the cock. Within a few seconds she was back on the edge and begged her master again, "please master my you whore cum now? She hopes her generous master would allow her to cum. Please. Whore is dying to cum master."

"Rub your clit now, whore, and cum, but don't stop rubbing that clit until I tell you, "Ordered Ray.

This was the command whore was dying to listen and didn't waste any time and started rubbing her clit. In a couple of seconds, a massive fountain of ejaculation squirted out of her cunt. Her rubbing the clit prolonged the sensation and the orgasm. It was days of arousal and frustration that suddenly got permission to be released. Her screams and moans echoed across the floor. She no longer cared who would hear them. The pleasure was genuine, and it was too much.

Rick realized what was about to happen and rushed towards the desk to catch her. Jessica passed out. It was pure ecstasy.

Steve took all the documents with him and told Rick to take care of her. "I'll handle everything from the documents side. Everything will stand legally as we'll have rock solid witnesses verifying that she signed all documents understanding everything. You just make sure she's there at the judge's farmhouse at 6:30PM Friday," said Steve.

"Yes, she'll be there. I'll make sure of it," replied Rick.

Rick picked up the naked body of Jessica like a baby and took her to the car. They drove her back to her house. If only she knew what was coming her way this weekend. A twisted, fucked up, sadistic judge and his friends will enjoy her for the entire weekend for something she would never agree to. Looking at things, her misery had no end.

* * * * *

Friday

Jessica finished her day and was extremely horny because of the constant stimulation through her piercings plus the gel from hell. That morning she came with Rick as he told her she wouldn't need her stuff for the weekend. He wouldn't allow her to carry her phone, watch, or her purse. He had ordered her to be outside in her usual parking spot and wait for him by 5:15pm. She had struggled a lot in the past few days as the whore was more prominent, almost all the time now.

She rushed out, trying not to be late and earn a punishment from her master. These days she was on her best behavior. Jessica stood at her spot and waited for her master. The only problem was she didn't know the time. "My life's so dependent on these gadgets that it's not possible to survive without them," she thought. Then, to her surprise, a red colored Aston Martin Vanquish convertible stopped in front of her. Rick was the driver. "How the hell did he get his hands on such a car?" thought Jessica.

Rick rolled the window down and said, "come on whore, I don't have all day," signaling her to get inside the car. Jessica followed the instructions and got in. "Perks of having rich friends. They let you drive their cars," said Rick in his excitement. It was Steve's car. Jessica remained silent and looked forward, and off they went to a weekend of misery for her.

When they entered the freeway, Rick tested the speed and went over 120 MPH. He was extremely excited and thought it was a once in a lifetime opportunity for him to drive such a car. He turned towards Jessica and said, "whore, both feet wide apart and on the dashboard now." The whore within Jessica got excited again and thought, "my master will play with me now. He'll let me cum." And with that, both her legs were on the dashboard, as ordered by her master.

"Now masturbate, whore. Show your master how much you want to cum for him," said Rick.

She followed the command, and her right hand pulled the hem of her skirt up and in went the fingers. In her desperation, she had three fingers inside her cunt and her thumb rubbing her clit. She had been horny the entire day, and it took little time for her to reach the edge. "Master, may your humble whore cum?" asked Jessica.

"Why would I allow a whore the privilege to cum? What have you done today that your master should give you such a privilege?" said Rick with a smirk on his face.

Jessica knew this was another twisted game and she'll have to take part in it, but the whore was more excited now. "Master, your whore has not done anything today to earn the privilege, but she's willing to follow any command her master gives. She'll earn the privilege to cum, master." Jessica replied, more eager to play the game than she should. "This whore is ruining everything for me," thought Jessica.

Rick pressed the button to roll the windows down. Jessica looked outside nervously, realizing what her master might order her to do. "If you want to cum, then one article of your dress needs to go. Remove it and throw it out. You won't need it again," said Rick.

Jessica looked at him in complete shock. She struggled to fight with the whore, but as usual, the whore won. With one swift motion, she removed her turtleneck, navy blue top and threw it out on the freeway with no concern about her nakedness. He wouldn't allow her to wear any underwear today. Which meant she only had one more article to lose. Her black skirt. She continued her fingering and waited for the permission to cum.

Few minutes later she struggled to control her orgasm as she hadn't got permission yet. She shivered because of her extreme orgasm control and begged again, "master please may your whore cum now?"

"Throw your skirt out as well and then I'll consider it," said Rick, without even looking at her.

Jessica tried fighting the whore again to not lose her last piece of dignity but failed. Soon she was back again, fingering her soaking wet cunt, desperate for an orgasm. The whore got even more turned on, realizing that she's completely naked and masturbating in public view. "Master, your whore begs you. Please grant her permission to cum," she said. The desperation in her voice was clearly audible.

Rick exited the freeway and soon joined a smaller road towards a rural town. He was now driving at a slower speed. He looked in the rearview mirror that a Ford pickup truck was behind them and was looking to pass them.

"You have no more clothes to lose, so let's play a game. I'll ask you a few questions and if I feel your answers are honest, I'll let you cum, otherwise you won't get permission from me."

"Yes, master. Anything my master needs, whore will not hesitate."

Rick slowed down further and gave way to the truck behind him, but before the truck could pass, he pressed the button to remove the roof. Jessica turned her head to her right to see a truck now matching their much slower speed. The driver, a man in his forties, was directly looking down at her. There was a clear lust in his eyes, and he wasn't in a hurry anymore. This mortified her, but she didn't dare to hide herself. She turned towards her master now, trying to ignore the truck.

Rick started off with simple questions for her. All the answers revolved around her confirming absolute submission and her whoredom. By now she had grown used to the nasty talk, so it didn't bother her that much. But then began the uncomfortable and personal questions.

"Whore, I know about your brother and your pathetic husband, but I do not know about your other relatives. Who else do you have in your family?"

Jessica crept back up after listening to this question, and whore failed to push her down. This was an extremely sensitive subject for Jessica. She turned and looked at Rick, fearing if she honestly responded to these questions, how he would use them later to ruin her life even further.

"Master, your whore does not have any other family members in her life," she thought it was true enough for him and hoped he wouldn't probe any further.

"What does that mean, whore? They're dead?"

"Yes, master. Your whore's mother died of cancer a few years before she graduated from uni."

"What about the father? He's also dead?"

Jessica paused for the longest time. She couldn't muster enough courage to answer that question. She hated her father from every fiber in her body.

"Answer the question, whore," yelled Rick.

Jessica panicked and said, "no master."

"Then where's your father, whore?"

"Your whore doesn't know about his whereabouts, master."

"Why is that?"

"Your whore hasn't talked or met her father since she was 16."

Now he was more interested in the conversation. "Have I found another goldmine here?" he thought. "Why? What happened, whore?"

She took a couple of deep breaths and said, "your whore's father was very abusive and one time he put Mike in ICU after which her mother divorced him. Since the divorce, your whore hasn't heard from her father, master." In this last part of the confession, she felt extreme mental pain. The trauma of her past came back. She no longer felt aroused. Her past kept flashing in front of her eyes. Rick also realized that he had hit an extremely sensitive spot in her brain. He had to bring the whore back, otherwise it would be a terrible weekend for the judge.

"I didn't tell you to stop fingering. Continue whore, and rub that clit faster," said Rick.

Jessica began rubbing her clit, fingering her cunt, and pinching her nipples all at the same time. It took her a few minutes, and the whore was back up. The horniness and the desire to cum helped her forget about the conversations a few minutes ago. "Please master, may your whore cum now?" asked Jessica.

"Does the whore really want to cum?" asked Rick.

"Yes, master the whore's desperate."

"What can the whore do for such a privilege?"

"Anything her master wants," replied Jessica.

Rick increases the speed a bit, and they pulled over on the side. Moments later, the truck also stopped behind them. Rick got out of the car and said, "don't stop rubbing that clit and do not cum without permission. Till then I'll talk to this amiable gentleman," and with that, Rick left her. Jessica had a fear of what he might make her do but the desperation to cum was way too strong for her. She continued with her fingers.

Jessica struggled to control her orgasm with her eyes still closed and fingers working hard on that clit. She opened her eyes and turned when the passenger side door opened. It was the truck driver standing with the door open and said, "get out whore. Your master wants me to have a closer look at his whore."

She stopped rubbing her clit and got out of the car. As she stood in front of this stranger, he said, "I never said you could stop playing with your clit. Continue and spread those legs so I can enjoy the view." She followed his instructions and started working hard on her clit while pinching her pierced nipple with her other hand.

He enjoyed the view, especially the exotic tattoos and piercings on her body. "Turn around," he commanded her. She followed the instructions instantly without stopping her assault on the nipple and clit.

"Wow! You were right. She really is a crazy whore. So, what's the deal here? I need to know exactly what I'm getting into before we even begin," truck driver asked Rick.

"It's simple. She's my whore. If you like what you see and want to try a sample right now, it's free. And if you like her services, you can contact me, and we can arrange something more exotic. She's a party whore, so you can tag along as many friends with you as you want. Based on your particular needs, we can negotiate a price," replied Rick.

"So, what you're saying is if I fuck her right now, I don't have to pay anything?" he asked again to confirm what he heard.

"That's right. I'll consider this session as marketing the whore. I'm sure you'll enjoy her and then I expect you to bring more clients for her. It's a word-of-mouth advert."

"I can promise you to bring way more clients for her, but then I need her free access to life," he tried negotiating.

"Free for life doesn't sound too amazing. You know that this whore is classes above any you'll find in the market, especially for your budget. Which means finding clients for her is not a tough job. But since you're bringing new customers, I can offer you a 25% discount, just for you, every time you bring new clients for her," said Rick in a firm tone.

He looked at her and saw a woman clearly out of his league. This made him realize Rick was telling the truth. There's no shortage of clients for this woman. "Deal," he said.

"Okay, whore follow this gentleman and show him the time of his life," said Rick loudly and then reaching close to her he whispered, "and if he's not satisfied with your performance today, I'll make your life even more miserable than before. And yes, you can't cum before he does."

During the entire negotiation among the two men, Jessica felt less than human. She felt like an object being traded. Dejected, she followed the stranger to his truck. He ordered her to climb on the bed of his truck and followed her.

"Both hands on the roof for balance, bend your back and spread your legs," ordered the truck driver. Jessica assumed the position with no hesitation. "Hey, I think you can help with a better promotion for this whore," he said while pulling his phone out and continued, "take this and record everything so I can show my friends what they're missing." He threw his phone and Rick caught it.

The man dropped his denim jeans and underwear down to his ankles and entered his cock, balls deep in her cunt in a single thrust. He started fucking her hard. "Play with your clit whore while I fuck you," commanded the man. Jessica complied as she neared her orgasm again.

"She can do exotic positions as well. The ones that you see in porn. Come on, whore, show the man some enthusiasm and do one of your exotic positions," said Rick from behind the camera of the phone, recording everything in high-definition video.

Completely embarrassed now, Jessica turned to the man and explained her position to him. He got excited listening to her next position. He had never fucked a woman with such agility. She turned to her with her left hand still on the roof for balance, but now she had twisted her body facing the camera. Her left leg on the truck's bed, with no bend on her knee and her right leg stretched upwards to form a perfect 180 degrees split, balanced on his left shoulder as he wrapped his left arm around the leg to lock the position.

In this position, her entire vulnerable body was visible to the camera, recording everything. The truck driver started fucking her again in this exotic position while she continued to rub her clit using her other hand. Her moans now turned into grunts. She squeezed her cunt muscles to tighten everything, bringing him closer to orgasm, faster than he expected.