Teacher's Dilemma Ch. 05

Soon she was back in her original position, eating the pussy in front of her while Jamie fucked her asshole from behind. By the time Jamie dumped his load deep in her bowels, Bella had three mind-blowing orgasms. Jessica had gotten much better with her oral skills, which unfortunately she won't remember once the night was over.

As people on both ends changed, Jessica felt the power of all the water she drank earlier. She felt an urgent need to pee. Jessica turned towards her master and pleadingly begged to him, "master your whore slave needs to use bathroom urgently. Please, master. Your whore will follow all commands please let your whore relieve her bladder."

Tyrone replied, "No. I'm showing you some mercy and your demands constantly keep on increasing. Now shut up and do your task."

Jessica felt dejected by the words from her master, but planned to control her bladder as long as possible. The queue of men fucking her asshole is going to make it much more difficult. But she had no choice. Rachael returned with a whiskey tumbler and handed it to Jessica. She said, "I can see your asshole leaking your master's precious cum. Scoop all that cum into this glass. Remember not to waste a single strand of cum deposited in your whorish asshole. All of it needs to go in this glass."

Embarrassed, Jessica scooped as much cum as she could from her asshole into the glass and when she felt there wasn't any more oozing out, she kept the glass away. Next woman in front of her was another black woman. She introduced herself as mistress Aliyah. Terry fucked her asshole next.

Aliyah's clit was supersensitive, and her fingers found her g-spot easily. Aliyah kept coming often. She loved the feeling. By the time Terry deposited his load, Aliyah must have had at least seven orgasms. Jessica's need to pee was increasing rapidly by the minute. She followed her orders and scooped Terry's load as well to the tumbler.

Next combination was David from behind and Anna on the front. Jessica felt jealousy when Anna sat in front of her like any other mistresses. It was difficult to please Anna, orally for her. She was the only woman who came along with David. She only had her single orgasm by the time Jessica had a load deposited in her asshole. Rose ordered her to continue with Anna until ordered otherwise.

After Jessica had deposited the new load of cum into the glass, next cock in her hole belonged to Mark. He while fucking Jessica's asshole started stimulating her clit. Jessica couldn't control this pleasure. Her bladder was also killing her, and the extra stimulation was too much. For the second time in the night, she fell on the floor, shivering from her overstimulation and hard to control orgasms.

"Please, master. It's too much for your whore. Please, she had to pee, master."

"You know the answer. It will not change because you're having difficulty controlling yourself," responded Tyrone.

Reluctantly, she stood up and got in her position. In a couple of minutes, Mark started his stimulation on her clit again. He had too much skill and exactly knew how to push her buttons beyond her control. Jessica lifted her head and begged loudly again this time she was crying like a child, "Too much... Please... Master... Ah... Ah... Ah... No... No... Please... Stop... Can't... God... Help... Help..." Then followed an ear-piercing scream from her. The control she was forcing on herself hurt her more than she ever remembered before. Her brain screamed at her to let go, but the fear told her to hold on.

Jessica surprised everyone with her resolve. Tyrone gave her some relief when he signaled for Mark to stop. Mark stopped completely and pulled his cock out of her asshole. It took her over two minutes of grunts and moans to calm down from the edge where she had reached. When in a better state, she said, "Thank you. Thank you, master. Your whore is grateful to her generous master for showing mercy on her." She was still panting profusely.

She had her eyes closed, trying to not break the rules. Then she felt the cock entering her asshole. She looked back and saw Mark was back at fucking her again. Jessica forced herself back into Anna's cunt. Mark just couldn't control his cunning desire to torture her as he brought his fingers back on her clit. He signaled Anna to hold her head in place so she couldn't beg anymore. Anna followed his command and kept Jessica's face on her cunt. Finally, as he found she could no longer talk, he increased his intensity of both his cock and fingers.

Jessica couldn't speak, but her loudest grunts told what she experienced. Mark was expert at what he was doing as he balanced her with his other hand so she couldn't escape by falling on her knees as well. Jessica did something he wasn't expecting, she clenched her asshole so fucking her faster got difficult. He smacked her cunt hard and yelled at her, "open up or you'll regret it."

Her cunt had become supersensitive from all events of the night and the smack felt hundred times worse than it should have under normal circumstances. She instantly relaxed her asshole with absolute fear. The constant strength she had to muster for this extended period to control her orgasm along with the lack of oxygen, she passed out again. This was the first time she passed out without having her orgasm. She passed out because she controlled more than she could handle.

Tyrone walked up to Mark and said, "don't push her too far where no one else can enjoy her. You know the plan, so don't deviate from it. I won't tell you again. Fuck her asshole and leave that sensitive cunt alone till I give the permission."

"Sorry, boss. I couldn't control myself, won't happen again," replied Mark.

Jessica woke up feeling exhausted already. She looked at Mark, still rock hard, which meant it wasn't too long that she had been out. He helped her up and forced her back into her earlier position. She turned her head back and begged, "Not the cunt master. Please, it's too sensitive." Without responding her he inserted his cock all the way in her asshole in a single thrust. Jessica licked and fingered Anna's cunt again. All three of them were back in the rhythm.

Anna came first, followed by Mark. Relieved after feeling Mark's cum in her asshole, Jessica took a deep sigh for not breaking the rules. She deposited Mark's cum into the glass. Then she realized that controlling her bladder would be more difficult than controlling her orgasm now.

David followed next, and Anna was still in the chair. By now, Anna's cunt was also hypersensitive because of multiple orgasms. Like Jessica, Anna also didn't have a choice to leave the chair until Rose gives her permission to leave. Thirty minutes later when David deposited his load inside Jessica, Anna have had countless orgasms. Jessica now felt jealous of Anna, but she didn't know that by now it had exhausted Anna. She also wanted to get out of this situation as much as Jessica.

Reggie fucked her next, but she had figured out a way to control herself while transferring all her frustrations to Anna. It was Anna now who could no longer control her orgasms, which appeared every few minutes. Both were hypersensitive to touch on their cunt, but Jessica also had another problem. Her desperate need to pee.

Only man in the house who hadn't fucked her so far was Tyrone. This brought a realization to her. He had shown no interest in fucking her so far. She thought to herself, what's the purpose of all this if he doesn't want to fuck her? Why doesn't he want to fuck her? She thought maybe if she could please him, she might get the permission to pee.

Jessica crawled her way towards her master and offered him, "Master, your whore had pleased every man in this house apart from her own master. May this whore have the privilege to please her generous master in any way he wishes?"

At that same moment, she heard the doorbell. Tyrone replied, "not all men yet. Crawl your way back and open the door. Invite our new guests inside with passionate kisses."

Disappointed at her small window to get the permission, she crawled her way back to the door. She stood up and opened the door wide open to a complete shock. Before she realized anything, her instant reactions took over, and she closed the door back again. Jessica could not believe that Steve, Ray, and Nia were standing outside her house. She cannot go ahead with this degradation. These are the people who are close to Jason. This is too close. Her brain yelled at her to run inside her bedroom and shut the door till everyone leaves her house. But she knew doing that would have much more serious repercussions.

Tyrone shouted at her, "what the fuck do you think you're doing? Open the door and invite our guests inside."

She wanted to do it, but her hands would not move at all. Jessica couldn't muster enough courage to face them in such a degrading situation. This will break her spirit. She had adjusted to fucking strangers and acquaintances, but friends were off-limits so far. How could she cheat on Jason with his friends and work colleagues? That is just too much.

"I will count till ten and if you don't open the door and invite our guests inside by then, we'll go out and knock some doors," threatened Tyrone.

After hearing the threat, she realized there was a much worse thing at stake. Even before he could start the counting, she gave up and opened the door. She had her head bowed down, staring at the floor. Jessica couldn't muster enough courage to look into the eyes of her friends while in such a degrading whore attire.

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All three walked in and Nia gave her a passionate kiss on her lips while her fingers playing with her clit. Both Steve and Ray repeated same gesture. Ray lifted her chin and, while looking into her eyes, said, "I knew since our college days that you'd make a perfect whore. Finally, your dream became a reality. There's no way that miserable and tiny cock could satisfy your whore cunt."

Jessica's eyes were moist again. Ray lusted over her ever since he was Jason's roommate during college days. He was still a bachelor. And never found the right woman for his kinks. When Steve found out about his kinks, he invited him to join his exclusive club. Ray was the one to tell Steve about Jessica and convinced him she would be the best performer for their club. Jessica was the first woman who he couldn't tame on his own, which increased his frustration and want for her.

Steve sat down on a chair and ordered Jessica to sit on his lap, facing everyone else. Jessica followed his order with both her legs spread on either side of his legs. She leaned her back on his chest. His chin rested on her shoulder, with him breathing softly in her ear. He whispered, "Now stay calm and answer all questions by Ray. Your answers will determine what we'll do to you next. If we're not happy with your answers, you might suffer a lot worse than you could imagine."

Jessica nodded, signifying that she understands. Steve brought his hand around her and started pinching her nipples along with the other hand, gently playing with her clit. Her clit was by now hypersensitive, but he didn't care about it.

Ray got the signal from Steve and asked his first question. "I heard that your hubby, Jason, has a tiny penis. Is that true? Tell us more about how he is in bed?"

Jessica saw he was recording a video on his phone. Everyone gathered around to witness her humiliation. The video showed both her and Steve's face perfectly. Aroused and frustrated from the past couple of hours. Her brain couldn't make coherent thoughts. She needed to get over with all this, and the only way for her would be to do as they please.

"Yes, he has a tiniest penis you could ever imagine. I can't even feel when he's completely inside me and he also suffers from premature ejaculation. Most time he's done in four to five thrusts. It is very frustrating for me. That's why I had to look elsewhere for my physical needs," lied Jessica in hopes of them to stop their torment.

Jessica had already said these humiliating lies about the love of her life before, but it felt much more miserable from within saying it again. Why? She thought it's possible because earlier she said those words in front of strangers and she didn't know they were recording. This time she's in front of people who know Jason very well and she knows they're recording. But something she felt guilty about was the increase of arousal. Just saying those words brought a surge of arousal within her. Plus, Steve's fingers weren't helping the cause.

Nia walked up to her and attached a leash on the metal ring of her collar. The ring was in front of her collar, vertically in between words "PROFESSOR" and "WHORE". From her moist eyes, she looked in shock towards Nia. There was a huge fog of desperate lust in her eyes. She couldn't think straight anymore. They had prolonged her denial, and she was getting excessively desperate now.

"Always say yes to all the questions," whispered Steve in her ear.

"Does Jason know his wife cheats on him while he's away from home?" asked Ray.

"Yes. I mean, he must know by now. His... Oh... Fuck..." she couldn't speak anymore because of her extreme edging. She was again struggling to control herself.

"Continue," whispered Steve.

"Oh, someone please fuck me. I desperately need to cum. Please."

"Answer the questions first, then maybe we will fuck your whore cunt," said Ray from behind the phone's camera.

"I haven't told him specifically, but I assume he would definitely know that his wife is cheating. There's no way he thinks I'm satisfied with his pathetic cock," said Jessica in between her heavy breaths.

"Would you take any cock in your cunt to satisfy your needs?" asked Ray.

"Yes. I will take any cock in any hole to satisfy my needs." Her desperation was clearer by each second now.

"How many strangers have you fucked so far behind his back?"

"I honestly don't know. It's too many. Please, I'm... Ah... Ah..." Steve had inserted three fingers while rubbing her clit and his fingers hit her g-spot perfectly. "Oh... Please... I need... cum... pee... fuck... pee... cum..." Her brain couldn't decide what she needed more, to pee or cum.

"What do you want?" asked Ray.

"I need... to pee and cum. Please, help me."

"Choose one."

"No. Please, I can't... I... fuck me... Oh... can't please..."

"I can't allow both. Choose one."

"Ah... Ah... I can't... Please..."

"What do you think, Steve? Should we allow her both?"

"Not without something in return. What can you do for us in return, whore?" asked Steve.

"Anything. Please, I'll do anything."

"Okay, let's see then. You'll crawl like a bitch in heat with your leash in Nia's hand to your neighbor's house and pee on his porch. You will then ring the doorbell and crawl your way back to your own house. This is the only way we'll allow you to pee or cum tonight. We'll be generous and allow you to choose the house." Steve enjoyed giving such humiliating and risky task to her.

Jessica couldn't believe her own ears. This couldn't be the task, it's too risky. Her neighbor can catch her in the act, and it'll destroy her reputation. But her body's need overpowered her logical thinking. She could not control any longer. Now the thought process was to remember which neighbor doesn't have security cameras securing their house. She needs to choose a house where she'll not be recorded. She remembered; Manson's family house didn't have a security system because Charlie Manson is too paranoid that if he had cameras in his house NSA will spy on him.

Only problem, his house was five houses away and across the road. That's too much crawling in such a vulnerable and humiliating attire. But it's the risk she'll have to take. Plus, it was past midnight by now and she knew most of her neighbors would be asleep by now. She decided and told them she'll crawl her way to Manson's house.

Rachael walked up to her and gave her knee pads. She said, "put them on my pet. I wouldn't want to see my pet hurt doing her task."

Jessica looked at her and felt anger, disgust, and betrayal inside but outside she said, "Thank you, mistress." After wearing the knee pads, Jessica was now on all fours. Nia grabbed the leash and yanked it so she could follow her. As they reached the front door of her house and about to leave, she heard Steve's voice, "wait a minute."

He came to them and pushed a giant dildo into her asshole. She screamed loudly because of the sudden unexpected invasion, but then adapted to the size. With the press of a button, the dildo inside her asshole started vibrating ferociously. Jessica gasped, audible to everyone. It would be extremely difficult to crawl to Manson's house with this much arousal. The vibrations were so intense that she felt she would cum and pee any second. And then they left the house.

Now the video switched to the phone's camera view, which she assumed was Ray's phone. In the video, she realized that the dildo in her asshole was a dog's tail. She was their bitch at this moment. Rachael smacked her ass hard and yelled at her, "raise that ass higher." Jessica instantly raised her ass higher while continuing her crawl of shame. She looked around to see if anyone heard Rachael and was now looking at her disgraceful ordeal. When she saw no one, she took a deep sigh or relief and continued to follow Nia. Jessica had already told the exact directions to the destination.

Jessica's heart rate was rising by the second. The risk of being found by her neighbors and the shame that would follow afterwards increased her arousal even further. The vibrating dildo already brought her to the edge. She was controlling. In her head she kept repeating, "Few more steps and you can have your relief. You have done it so far, just a few more steps. Hold on."

Finally, the moment arrived. Jessica was now sitting on her knees, hands locked behind her back and legs spread wide open. She was on the porch of Manson's house, few feet away from the front-door. This was the moment, and the dildo in her asshole was sending exceptional pleasure sensations to her entire body.

"What do you have to say, whore?" said Ray in a loud voice.

Fear struck Jessica, asked, "May your dirty whore slave have the permission of her generous master to pee on the porch of her own neighbor's house? Please, master Ray. Your whore will serve in whichever way her master deems fit. Please let your nasty whore pee."

"Start rubbing your clit right now," commanded Ray. Jessica instantly followed the command. "Harder like your permission depends on it." Reluctantly, Jessica obliged with the command. It made it much harder to control now. She couldn't control her grunts anymore. They got much louder.

"What do you want more? Pee or cum?" asked Ray.

"Both. Master, your nasty whore desperately needs both. Please. Ah... impossible... it's imp... now... please.... Oh..."

"Pee now, whore. Fingers working the clit."

Jessica yelped loudly as her bladder released the warm liquid out. It took her over a minute of high-pressure release to discard all the piss out of her system. Her desperate need to cum instantly replaced the relief she felt afterwards. "Thank you, master. Please, may your whore cum now? Please master, let her cum now."

She kept waiting for the permission which didn't came for the next few minutes and her edging had reached beyond her limits now. As she thought there's no conceivable way to control any longer, she heard the words, "cum now whore." With a loud grunt, she came hard. When Ray saw the amount of ejaculation sprayed out of her cunt, he thought she was peeing again. It was a ridiculous amount of fluids released from her hole.

Few minutes later she was still panting profusely. She felt a whole new euphoria and was ecstatic. Jessica released an unbelievable amount of frustration out of her cunt. She felt fabulous. She couldn't admit it to herself. As she came down from her euphoria, she heard the next command from Rachael, "suck those nasty fingers clean."