Teacher's Dilemma Ch. 01

With impressive control, which she didn't know existed, she continued, "I opened the lube bottle and dropped a generous amount of it on his asshole, and inserted my middle finger. He was squeaking before I had two knuckled in so I shouted at him, shut up you fucking bitch you can't fuck and you can't take the fucking, what the hell are you good at you looser."

Through her profuse panting, she said, "he instantly came back to original position and restrained himself from making any noise. Within a few minutes, my middle finger was completely in and now I added one more finger. This brought a loud grunt from him but he didn't dare to move at all."

This was getting much more difficult now for her. "Before I knew I had three fingers completely inside of his asshole. Now was the time to drop the hammer. I took the fingers out and tried inserting the huge rubber cock in his asshole."

Her cunt muscles were doing heavy workout, "I had to add more lube since it wouldn't go in. It took like forever to get the head of the cock past his asshole. Now his grunts were getting much louder. I knew he was in pain but that looser didn't dare to complain because he knew what I would do, would be much worse if he opened his pathetic mouth to say a single thing."

"It was not long that more than half the cock was in, but now things were getting slower. His asshole won't accept it anymore. So, I had to slow down and try deeper thrusts with some more additional lube. Few more minutes longer and the entire thing was in."

"His grunts were now beyond control, but it was time for my pleasure, so I started the longer and deeper thrusts. The friction inside the strap-on worked its magic on my clit. I was so aroused that I didn't give a shit how much it hurt him and now I started faster and deeper."

"Once I went ahead with the fucking, I heard the fucker moan along with me. I couldn't control myself and yelled at him, see you fucking idiot, how simple it is to please someone with focus and compassion. Few minutes later I felt my orgasm building, and I increased my speed."

"What I found out was that fucking looser of a husband was aroused again, which was shocking for me. Aroused from getting fucked up by his ass. By the time I reached by orgasm he again couldn't hold on to it and came again hard."

"I was so much angry and frustrated that this idiot came again while I am still trying. His body was completely shaken, but I kept ongoing I didn't give a shit about him anymore, I just wanted my orgasm. And when I came, it was earth shattering."

"It was a buildup from months, possibly years, and all frustrations, now released. That was the day I realized this is what I need and only a real man can give it to me. My husband just doesn't have enough dick to satisfy me or any woman."

She was sweating profusely now and hoped that this was enough degradation for her husband, so she begged again, "I hope the story was good enough for all of you. Please let cum now, I beg you please."

Reggie was smiling now, since he knew he had her where he wanted. "What do you think guys was the story good enough?"

"I don't know man, I felt like the story was a little rushed, don't you think so Terry?" said Mark.

Terry instantly chimed in, "yeah I felt like there were lots of loopholes in the story, like details were missing I would say. Not good enough for me."

Jessica's face was completely flushed now she knew she can't continue like this any longer so before the voting could continue, she responded in shaky voice and out of breath now, "I am extremely sorry guys if I missed any details, but I can't hold on anymore, please I beg you let me cum. I'll do whatever you demand, just please let me cum. Please."

It was hard to be she didn't dare to slow down the speed or pressure of her fingers.

"Okay. Look directly into my eyes and make me believe you deserve to cum. Why should we allow a slut like you the privilege to cum?" said Reggie.

Jessica's brain was no longer working properly it screamed that it's not possible to delay even a second, but she forced herself somehow to hold a little longer, she can't allow them to throw her out, not after all this.

"This slut knows that privilege to cum is earned by a lot of demanding work, but she begs all of you to just allow this slut to cum just this once and this slut promises all of you she'll go above and beyond from now on till she's allowed to leave this place."

With unbelievable resolve she continued, "she will show all of you that there is no other slut in this entire world like her if she's just given the permission this once."

She did not know what else she could say about whatever came to her mind; she said it out loud, hoping for the best outcome.

Reggie got what he needed and said, "If we break our rules and give you the early privilege of coming before you had serviced any of us, the stakes and demands will be exponentially higher for the entire time you're here. Are you accepting the terms?"

Jessica was too far gone to think straight there was no way to hold on any longer and hence she said frantically, "yes I accept all your terms and conditions. I will do whatever the demands, in fact I promise to go beyond the demands for the entire time I am here. Please give this slut the permission to cum."

Reggie said, "Good. Now look directly into the wall behind me as if I am standing there, increase the speed and curl your fingers I want you to stimulate your g-spot every single time your fingers go in, and I want your thumb to increase the pressure further."

He continued, "Looking in the wall behind me, in desperate and sexy voice repeat exact words - I Jessica Peterson a physics professor at the university am a really dirty fucking whore who needs big black cocks from strangers deep in all my holes before I can cum."

They told her to repeat this statement with all sincerity 10 times and only after 10th time they will allow her to cum.

Jessica got her instructions, but she did not know how to go any faster with her fingers. She could somehow spread her legs, which gave an amazing view of her cunt to all four sitting in front of her, but also gave her even better access.

This helped her to increase the speed even more with curling her finger she found her g-spot which sent electric shocks in her body and with more pressure on her clit, repeating the statement 10 times seemed like impossible, but she went ahead looked directly at the wall as if staring at some invisible man's eyes and repeated the most degrading statement about her.

10th time it was like someone has opened floodgates and as she came her entire body was shaking violently and first time in her life, she squirted massive amount of fluids.

She knew some women were squirters, but never thought she was one. It was like she had drank a gallon water and was holding for a long time but now peeing. For 10-15 seconds that her fluids kept on coming out now, her mind was worried if this was possible or was she just peeing on the floor? After the entire fluid was out, she just collapsed on the floor and passed out.

Reggie instantly called Tyrone, "boss are you seeing this? You got yourself a gold mine. Girl's a squirter they're rare to find these days."

Tyrone replied, "yeah I saw that and I'm as shocked as you are. Don't forget you tasks, I want you guys to fuck the shit out of this one. As much as you can, no holes left. Let her go after 10pm Sunday, not a minute before. And remember if your dick can get hard it needs to be in one of her holes."

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Jessica was having a terrible nightmare. She is telling extremely humiliating stories about the love of her life, Jason, and that too in front of complete strangers. She just wants to wake up and crawl up in his arms and cry and ask for his forgiveness.

How could she even think about such things even in her dreams? Suddenly, she felt Jason's hands pressing her tits and pinching lightly on her extremely hard and larger than normal nipples. Her perky pink nipples, when fully erect, could go a little over an inch tall.

It felt so good. She was getting aroused then there were his fingers entering her cunt while rubbing on her clit. It was heaven, but suddenly she realized there were two hands on her tits and one on her cunt. There was someone else, why would Jason bring someone else with him and suddenly out of shock she opened her eyes and saw that she was in the middle of a gigantic bed and one side of her was Mark and other side was Terry both kneading her tits and occasionally pinching her huge and now erect nipples.

Looking down, she saw David had her both legs spread and had his two digits inside her completely and then came his warm mouth as he started sucking on that large and erect clit. As he did that, both Mark and Terry followed the lead and started sucking on her tits and biting on her nipples.

Before she could process what was happening. Her orgasm was already on her peak, and everything instantly flashed back none of it was a nightmare, it was all a reality.

Suddenly, someone lifted her head and placed a large pillow under her head. Now she can clearly see David working her cunt along with a large, comfortable chair behind him. She turned around to see Reggie standing there with a large bottle of water and said, "you are quite a squirter, huh. You've lost a lot of fluids, so let the boys continue with their job and grab this bottle with both your hands."

He continued, "your task is to put that straw in your mouth and no matter what, your mouth will not leave this straw until this entire bottle is empty. Now it's up to you if you finish it in two minutes or take two days. But straw remains in your mouth till there's water in this bottle."

Someone placed a giant bottle on her chest between both heads and straw in her mouth, he said, "rule for you to cum is same for the rest of your stay and since you've already had your exception there won't be any more for the rest of your stay. I suggest you quickly learn to build some extreme resilience because things are going to get more extreme by the passing hour. We don't want you begging us for exceptions every time you can't control your libido."

Both mouths were now sucking and biting on her sensitive nipples even more vigorously. She started sucking on the straw, as she felt thirsty. Only problem was the bottle placed on her was a gallon of water. She has never in her life drank a gallon of water at once.

As David increased his suction power and started biting her clit now and then with his three fingers curling in and out, touching the most sensitive spot. Second orgasm for the day was now seconds away, and she looked at the bottle which was less than half finished.

She looked pleadingly towards Reggie, who now sat on the chair right in front of her. He looked in her eyes and shook his head furiously, as if saying, don't you dare even think about it? She knew she can't even ask about it without finishing the water.

Taking the challenge and she started sucking on the straw as if her life depended on it. She made the plan only way to finish the water is to keep on drinking it till it's finished, otherwise her mind will send her instructions that she's full.

So, she did as plan and the amount of mental strength and focus needed to achieve the task diverted her attention from the ever-forming orgasm as well. She felt good, she can finish this task.

But as Reggie saw that water was now suddenly less than a quarter left, he said, "now boys, is that All You've Got. Increase the level. This is no fun she's about to finish the water. Now would it be any good if three guys all together get defeated by one girl all alone?"

This motivation changed the dynamics again since all three guys increased their passion by like ten folds. Her orgasm now yelling in her head for a release, and she knew there was not enough strength in her head to hold off any longer, which caused her to lose her focus on drinking the water.

She closed her eyes tightly, trying her best to hold off if possible. Her body started shaking and an exceptionally soft voice somewhere in the back of her head was saying, "you idiot, there's only one way to finish the water."

And against all odds, she started drinking the water from the straw even much faster than she thought was possible. She felt her stomach hurting from being full of water, but she didn't give up. And in no time, there was no more water coming from the straw and as she looked down at the bottle, she had finished the water. Her mouth left the straw and instantly begged, "Please, may I cum, please."

She really impressed Reggie with her resolve, but he would not make things easier for her as he said, "Since all the boys are busy and cannot provide you with the permission. I will start a countdown from 10 down to 0, after which I will give you my decision if and only if the decision is cum, will you cum. Nod if you understand." Jessica nodded frantically.

Reggie said, "boys now for next 10 seconds I want you to take her to the pro shop. Let's begin now". With that, the stimulations in her most sensitive parts were so high that to hold off for a single second was a mammoth of a task.

She was told to not close her eyes and look directly into Reggie's eyes as he started counting. "Ten. Nine. Eight. Seven", by now her body was shaking so much that Reggie thought there's no way she's going to control till zero, "Six. Five. Four".

Now this was interesting her body had given up long ago, but somehow her strong-willed brain was holding off on her orgasm. She had to be the most strong-willed woman he had ever seen, "Three. Two. One. Zero. And boys STOP."

Jessica couldn't believe her ears as per the command all hands and mouths just left. Mark and Terry pinned her down by putting pressure on her shoulders, and David did the same by putting pressure on her inner thighs.

Her body was shaking as she looked into Reggie's eyes, begging as he coldly replied, "I have not given you permission to cum. Decide your priorities what do you want more cum or stay here for the rest of the remaining time."

She wanted to stay, but controlling was no longer possible for her. Reggie looked at her cunt lips, which were trying to open, but she had put immense strength in her muscles to hold off.

Focusing on her physics research that was going on with some of her PHD students but could not focus or make any coherent thoughts around it, but what it helped with was calming her down. It took extreme mental strength on her part and a couple of minutes before she was now down from her peak and could think about not so important work stuff.

Reggie had a shocked look on his face. This has never happened to him, ever. No girl has ever defeated him in this task. "Challenge accepted" he thought to himself.

Jessica knew this was not the end of it and this was going to get worse and didn't have enough confidence left in herself to pull through the entire time. She did not know that Reggie had changed the game now in his head.

He knew her mental strength was difficult to break, it's her physical strength he'll target next. He told her to stand in front of him. He said, "I am impressed with your resolve, so now the next task is for you to seductively walk up to Mark, beg him to let you fuck him."

She knew this would be a task but wasn't sure so soon, "make it sexy enough for him to agree. Once you get the permission, gently remove his boxers all the way out. Then give a nice blowjob till he's completely hard, then turn around and face me, look directly into my eyes as you ride him reverse cowgirl."

"Remember, this is completely your job he will not move a muscle. But since you're doing so much work, you get a pass to cum as many times as you can only catch is you have to take Mark all the way in and with each thrust you must rise till the head of his cock and go all the way down. If you can't do this, you can't cum."

"Oh yeah, I totally forgot one thing. All the while you have to talk dirty to us, explain all your feelings and tell us in graphic details about how Mark's fucking is so much better than the one given by your pathetic husband. Now go."

This somehow sounded much worse than what she had done so far. But since there was no choice left, she turned around and saw Mark was lying in the center of the bed with his arms locked behind the back of his head as if relaxing on a beach.

She seductively climbed onto the bed and crawled up to him and begged to him, "May this slut have the privilege to fuck you, my good sir. Slut promises you won't have to move a muscle she'll do everything as it's her need that your massive cock is going to fulfill," she did not know where that came from but that was the best she could think of.

She completely surprised Mark. He never imagined that she could say such a thing and all he could say was, "Sure whore. Ride along."

Jessica gently removed the boxers and threw it aside in the room's corner. As she saw his cock, it shocked her. It must have been around six and a half inches with no erection, which was Jason's size with a full erection. As she started jerking him and sucking the giant cock, it grew bigger and bigger and by the time it was in its full glory it must have been over ten inches with at least two and a half to three inches in diameter.

Now she knew the problem, how was she supposed to take it all in, but she can't do anything without trying. She turned to look Reggie in his eyes and positioned herself for reverse cowgirl, positioned his cock at the entrance of her cunt. She slowly started going down even with her completely wet cunt and all the saliva on his cock it was still exceedingly difficult to focus and get at least the head in. To make matters worse, she got a nod from Reggie expecting her to describe her experience as she's going down.

She knew there's no arguing, so she continued with exaggerated versions of her feelings. She felt like she was a professional porn star fucking for a movie. So, she continued, "Ah! This is the cock I have been waiting for my entire life. Such a massive cock it feels like it will rip my pussy apart."

With Reggie's disappointed look, she knew the verbiage was not dirty enough for his taste, so she changed it, "Oh my god! It's so big it's going to rip this slut's cunt in half. This is such a wonderful feeling. My Jason's micro-penis is not even the size of your middle finger Reggie," obvious exaggeration but Reggie wouldn't mind it for sure.

"Ah! Ah! Ah!" By this time, she was more than halfway down because of more than enough lubrication but now it seems like it can't go any further, but she was determined to complete all her tasks, "This is so amazing. I feel so wonderful oh Mark, where have you been my entire life. I wasted so much of my life fucking Jason, where I could have been your whore my entire life. I mean, this cunt is made for big black cocks like yours."

She was going all the way up till over 8 inches down. "Ah! If you promise this whore to fuck her cunt regularly, she will be your whore for life. Oh my god!", and she was now all the way down and it hurt her this has been beyond her limits.

She took few deep breaths to adjust the size and width but the moment she saw Reggie making hand gestures telling her to continue with her feast. She went up all the way till she felt the head of his cock and then to its base.

For almost next 5-6 thrusts she didn't talk at all as she was focusing on the rhythm and with the amount of stimulations she had received before and everything that has happened today the giant pending orgasm was back at its peak and she was glad she could have it without permission but suddenly remembered the other rule of the task, so she continued, "Oh my god! Oh, my god! I can't believe I am taking all of your giant cock."