Teacher's Dilemma Ch. 08

"Oh, fuck man. She's good. Oh... I'm going to cum soon, man. She's amazing. Wow!" He couldn't believe his luck at this point.

Jessica heard the words and felt much happier because after he deposited his load she could cum as well. Hence, to intensify his experience, she talked nastily, as it helps to increase arousal in men. "Oh... Oh... my god... you're so big... yes fuck this whores cunt... yes right there... deeper... oh fuck you'll make me cum... fuck me... fuck me... fuck me..." She repeated her words several times directly looking into the camera.

This brought him over the edge, and he deposited his load deep inside her cunt with a loud grunt. She desperately needed to cum, so she increased her intensity on her clit. As she was about to cum, she saw another car passing them. It was an old woman driving the car, and she looked directly at Jessica and rolled her window down and yelled out, "whore! Get a fucking room to earn money from your nasty cunt don't ruin our neighborhood."

Before she could pass them, Jessica gave up and gushed the massive amount of liquid lava out of her cunt. The pleasure and humiliation were too much for her and her growls were much louder, easily heard several meters away from the truck. In her absolute lust, she looked directly into the eyes of the old lady while continuing with her orgasm. The woman felt embarrassed and put her foot on gas and passed them.

It took Jessica a few minutes to calm down from her extreme orgasm. She was still sitting on the truck bed when Rick returned and said, "let's go whore. We're running late. Your guests must be waiting for you." Jessica stepped out of the truck and sat again in the sports car. As he started the car, a voice from behind came, "I'll call you once she's back from her exciting weekend. Let's arrange something soon."

"Sure. Call me and I can arrange everything for you and your friends," replied Rick and with that, they left. Jessica felt like a cheap whore for fucking a stranger outside while a woman yelled at her. "How much more would they humiliate and degrade me? How am I supposed to live my life like this? Would this torment ever end? Do I even have any hope of surviving this? Now I miss Tyrone. He made me do fucked up things, but he took care of me as well. These people don't care if my life is ruined completely." She couldn't control her terrible train of thoughts.

Both remained quiet for the rest of the trip. Rick was excited as he was considering all the money he can earn on the side from her. And then he stopped his car outside a massive farmhouse. There was no other house close to it. Massive fields of farmland surrounded it. Jessica had a bad feeling in her gut. "What would they do to me? Why do I have this bad feeling about today? I've done so many terrible things so far, but somehow this feels like it would be much worse," thought Jessica.

"Remove your hair extensions and place them in the glove box," ordered Rick as he got out of the car. Jessica followed the instructions. He was searching for something inside the trunk. Soon he returned and said, "wonderful. Now let's put this collar on you." It was a black leather dog collar. He quickly attached the collar around her neck and tightened it to make it much more uncomfortable for her.

Next, he attached a black colored leash to the ring in front of her collar. He gave a couple of hard tugs just for fun. "Looks really nice on you, whore. Now get out of the car and on all fours like the nice little bitch you are." Jessica followed the instructions and crawled behind Rick as he kept pulling the leash harder on her to increase her speed.

A few feet away from her, she saw an old man waiting for her. The guy must be in his mid-sixties. At 5'8" and a massive beer belly, he was a typical old white guy. "Remember, he's the judge and your master for the weekend. Don't disappoint me, whore. Do whatever he and all his friend's command you. If I hear any complaints about your misconduct, you'll regret it for an awfully long time." Jessica looked up towards her master and nervously nodded to confirm her compliance.

"Here you go sir," said Rick while handing the leash to the judge.

The old man took the leash and said, "I appreciate your timely delivery of my pet."

Rick nodded and looked down at Jessica and said, "be a nice and obedient pet for your new master, whore." And with that, he turned and left towards the car. Jessica almost wanted to cry. She had an extraordinarily strong and unwanted feeling lurking within her tummy. "This will not be the same. Something is not right here, and I feel like it's going to be much more difficult for me than I'd ever felt before," she thought.

The judge pulled the leash and turned to enter inside the house and said, "come on in, pet. Let's have some fun. This will be a weekend you'll never forget."

Jessica followed her new master like a bitch in heat, but she was extremely nervous from inside. The judge shouted, "come on boys out here, we have our toy ready for the weekend. Let's play some games." She felt like an object and not like a human. He took one knee and patted the back of her head like a real pet and whispered in her ears, "you know, pet, most of the folks are my childhood friends. In life, we've had too much sex and kinky stuff, included. Sex doesn't excite us anymore. We now need a toy to play with and today it is you."

His creepy way of talking scared Jessica beyond her imagination. "What are they going to do to me if not sex?" she thought. She remembered the words once told to her by Mike when they were much younger, "death is not scary Jess but the fear of death is terrifying."

She turned towards the voices and found a bunch of old guys walking towards her. Most of them were in their fifties and some in their sixties. There was one naked young black man following them. He had a black leather slave collar that had the words "Club Property" inscribed on it. As he got closer, she realized he must be in his twenties and had a massive cock still semi-erect.

The Judge yanked her leash hard to bring her focus back to him and said, "I see the massive cock of another slave mesmerizes the pet. You'll get it when we decide. Your Mistress Rachael inducted this one to the club. Let's have some introductions so you remember who's who." Forcing her head to turn slightly right by yanking the leash, he continued, "that is your master Jake and that's master Paul. Moving to the next person, that's your master Ryan, then next to him, master Kevin, followed by master Garth," said the judge, introducing his friends.

Jessica turned back to the black guy and heard from behind, "and this man who you can't take your eyes off is club's property and his name is slave James. And you'll refer to me as master Kurt. Now, did you remember the names of each master so far?" Jessica closed her eyes to remember everyone's names and then nodded. "Look at each of your masters and greet them with their names," ordered Kurt. Jessica turned and greeted every person in the room with master followed by their names, including James.

"James here is not your master, he's just another slave like you. You'll refer to him with only his name. Do you understand?"

"Yes, master."

"Now, pet, we'll show you the playroom. But there's one condition," he turned towards James and said, "what are you looking at, slave, come here fast."

"Yes master," came the reply from him and he rushed in front of Jessica.

"Now grab this leash tightly and do not let it go unless I command you to." He turned back to Jessica and continued, "Give this man a nice blowjob till his cock is rock hard. Continue now."

Jessica crawled forward and tried to grab his cock when she heard, "no hands allowed whore." She brought her hands down and began sucking his cock. It took her skilled mouth only a few minutes to bring that massive cock to its full glory. "It must be at least twelve inches, if not longer. Oh, how much I'll enjoy fucking him," thought the whore within Jessica.

"Now that we have his cock nice and big, let's move along. Challenge for you pet is that you will crawl your way following James without letting go of his cock from your mouth. If that cock slips out, we'll castigate you. Keep your eyes up and locked to James while you crawl your way towards your den." And with that command, all her masters turned and started walking towards her next destination.

James yanked the leash to remind her she needs to move now. He started taking steps backwards while holding her leash. Jessica began crawling and focused on his eyes while continuing to suck his cock while on the move. It was one of the most erotic sequences one could imagine. It was a massive farmhouse and took several minutes for them to join the group. Jessica was really enjoying the taste, size, and erotic moment of this hunk. She gave everything she got to this magnificent cock.

"Now in you go pet," said the judge as he was holding a wooden door up that was a hidden entrance. There were stairs going down below to an unknown basement. The floor camouflaged the door when closed. Whatever her destination was, it was underground.

James carefully started descending downstairs. It was not an effortless task to move backwards like he was, while Jessica wouldn't let the cock leave her mouth. It was like her life depended on that cock. It took them a few more minutes of careful walking to reach the basement with no incident. Once they reached their destination, Jessica began deep throating his cock hard. She thought her task was to fetch the delicious cum out of his cock. But soon everyone joined them, and they shut the door above.

"You all can see how horny this bitch is. We'll all bring some of that heat down this weekend," exclaimed the judge. "Now let go of his cock pet. That's not your toy. You are our toy."

Jessica stopped sucking and reluctantly let him slip his cock out of her mouth. She sat kneeling on the floor and now looked around the room. Her heart came out of her mouth. This was in a dungeon with so many torture devices she couldn't even imagine. Kurt had intentionally designed this room to be old and dirty. It could intimidate any toy he brings down here for his pleasure. The magic worked on Jessica as well. She no longer felt horny, but only had the feeling of absolute fear. "What would they do to me here?" she thought.

"Stand, pet," commanded the judge.

Jessica followed the instructions and stood waiting for her torment to begin. He grabbed the leash and pulled her towards a massive wooden cross. With the help of James and other guys, the judge tied her to the cross. She was spread-eagle and a few inches above the floor. The fear of the unknown was absolute in her head. Then she saw the judge had something in his hand but couldn't understand what it was. With a swift motion, he inserted something curved up into her cunt. It must be around 6-7 inches long but had a curve to it.

"Hold it in while I place the lock on all the piercings of your cunt," commanded the judge. She tried her best to keep the unknown object inside her cunt. Soon, the judge had two metal rods passing through the piercings and placed it into a tight lock through a big clip. This made sure she had no ability to open her cunt lips and release the object locked inside.

"What's inside your cunt pet is a changed version of a g-spot stimulator. It's ergonomically designed to provide extreme sensations directly to the g-spot. Both pain and pleasure. The custom material that we used for your piercings was a test set for you and it became successful. We did another version of it on one more slave and it's just awesome. Best part is we get to develop more gadgets that work in sync with the material you already have. Like this," he said, showing her some ridiculously small metal clips.

He attached those clips to each of her nipple piercing and her clit piercing. Once satisfied, he said, "these things are ten times more intense than those nano chips that you've become so used to. The best part is that they're highly configurable as well. They designed these per our specifications for this weekend. Let's see how you feel the pleasure first." He pressed a button, and everything came to life at the same time.

The sensations within Jessica reached beyond anything she had experienced before. This was multiple times more intense than those nano chips and she had always struggled with them. In less than thirty seconds, she was moaning louder, and her orgasm neared its edge and then everything stopped. She opened her eyes and looked at her tormentor with pleading eyes.

"See? Isn't this better than the version one chips? How was it, pet? Did you enjoy the clips and the sensations from inside your cunt?" asked the judge.

Clearing her throat she answered, "thank you master for considering your pet worthy enough to experiment these wonder machines on her. Yes, master is right. These are several times better than those nano chips."

"Let's check the other side of it then, pet." And with that, he pressed another button, and everything sprang back to life, but this time it was an agonizing pain for Jessica. Her screams echoed through the soundproof dungeon. The G-spot stimulator which helped her provide an absolute pleasure became the most painful device with just a click. The clip on the clit piercing enhanced the pain to an unbearable level. When legal companies manufacture such devices, they try to limit the pain level, but the judge had no such limitations.

A few years ago, Kurt had a major stroke which damaged a few nerves causing permanent erectile dysfunction. He had an excessively active sex life for his age before the stroke, but afterwards, the disappointment was huge. Rachael was looking for vulnerable people for club members and found one in him. The club was a fabulous idea by Rachael. As with the gang, she needed someone else to become the face, hence came her sister's husband, Steve. It wasn't difficult for her to manipulate Steve into accepting the opportunity. She was the master planner behind everything, but if legal things went sideways, she could easily cut corners from everyone. The club provides another way to blackmail powerful people into doing things she wanted.

Kurt, over the first few months after joining the club, felt frustrated watching everything but not being able to take part. This made him extremely bitter and eventually a sadistic motherfucker, as claimed by Rachael. Now he enjoyed inflicting pain on the slaves from the club. It helped him transfer his frustrations to them. Since his friends were not powerful enough to get an invitation from the club, he showed them what perks he enjoys at the club. When he realized that his help was necessary for their plan to move forward, he placed his foot down and demanded Jessica for the weekend. Eventually, both Rachael and Steve agreed, but only on one condition, he could not inflict any permanent damage on her, especially this close to her debut at the club.

It was less than forty-five seconds and Jessica started crying profusely and felt a sore throat from such loud screams. She had experienced pain before and grown used to finding pleasure in pain, but this was something different. This felt like plain torture, nothing pleasurable about it. Her arousal was long gone, and she felt nothing but extreme pain.

He then pressed the button again to turn everything off and said, "wow this works even better than I thought." Kurt discussed these new gadgets with everyone like a kid showing off his favorite toy to his friends. It took several minutes for Jessica to calm down from that severe pain.

"What do you think about that pet? What would you like next, pain or pleasure?" asked Kurt, with a huge smirk on his face.

"No more pain master, please, your pet begs you. She'll do exactly what her master's demands. Please, no more pain." Jessica begged as best as she could, almost crying again at the mention of the potential pain again.

"Okay, now that you understand what your punishment would be if you break even the smallest rule while you're my property. Let's discuss some ground rules. You CANNOT cum under any circumstance without my and only my explicit permission. Do you understand, pet?" said Kurt in a stern voice.

"Yes, master. Your pet understands she cannot cum under any circumstance without her master's explicit permission," replied Jessica as seriously as she could under the circumstances.

"You will do exactly as we command you to do with no question or hesitation. If you say even a word or hesitate for a microsecond, we'll consider it a violation of house rules. Each violation will add ten seconds to your punishment. First punishment starts at thirty seconds. But if you directly refuse or break any rule, we'll consider it a crime. Each crime adds two minutes to your next punishment. And the punishment timer would be cumulative, so you do not want to commit multiple violations or crimes. Do you understand everything, pet?"

"Yes, master. Your pet understands all the house rules," replied Jessica. But internally she thought to never commit a crime while in this house. The near forty-five seconds torture told her she won't survive the two minute one.

"Guys, now our pet understands us. Let's begin the show. Grab whatever you like from the shelves." With that, he pressed the button again and all the pleasure sensations returned. When everyone returned, each had different pain inflicting instruments.

She looked down to see Jake was holding a wooden paddle that had rubber padding with a rough surface. Paul had a whip. Ryan held a cane, and Kevin had a riding crop. Jessica turned slightly to find Garth with a flogger and Kurt with a leather paddle. She closed her eyes for two reasons. One, she had again reached to the edge of her orgasm and was already struggling for control. And two, she didn't want to see her torment.

Every inch of her body was vulnerable to their attack, and she could not defend herself. She got louder with her moans every second. These new gadgets were the improved version of earlier ones and gave increased intense pleasure and pain to the most sensitive parts of her body. Just when she felt lost in the pure lust and pleasure, she felt a sharp tinge of pain when the first strike of the whip hit her below her tits.

The sudden strike took her by surprise, even though she knew it was coming. She gasped for air and couldn't find her voice to scream. Before she could adapt, a hard hit by the flogger hit directly into her cunt. This time she found her voice and screamed because at this point every part of her cunt was excessively sensitive and that hit hurt her more than she ever imagined.

The next few minutes, each man took turns hitting her with the objects in their hand. Her screams got softer as she started to manage the pain. It was then the pain started intensifying her pleasure further. Now her screams came mixed with much louder moans. She had strips and marks of their attack across her bound body. Initially, it felt exceedingly difficult to manage the pain, but now it enhanced her arousal even further.

"Oh... Oh... Oh... my god... master please may your pet cum? Please master, your pet is desperate. Oh... Oh..." she kept begging her new master for permission to cum, which she didn't get. Each strike and every second of artificial stimulation became unbearable for her. Her body was shaking and shivering now because of the intense orgasm control she had been put through.

Completely mesmerized by her performance and unbelievable control, Kurt stopped and try something different. "Okay guys, I think that's a good enough warm up for our pet. We should try something different now."

Hearing his command, everyone stopped along with the excessively pleasurable gadgets. Jessica started breathing intensely to calm herself down from this edge. A few minutes later, they helped her down. She was told to kneel and spread her legs wide open with hands locked behind her head. Jessica followed the instructions without hesitation.