Teacher's Dilemma Ch. 01

"This whore is going to cum all over your cock and will keep on fucking. I love it and I am... Oh... Oh... and... I am... oh my god, I am coming...", and with her body shaking she squirted second time in the day and the pressure was so strong that it flew a few feet further and dropped at the edge of the bed.

This view mesmerized Reggie. He had never met a squirter before and specially not one with such tremendous amount of gush. Jessica herself didn't know that she was a squirter. She thought first time was different, but second time means she was a squirter.

She has had orgasms with Jason, but they have never been to where she would squirt. As she calmed down, Reggie's indications were clear ride on. So, she did. The task was straightforward: keep on riding till Mark comes.

It was getting difficult now she was running out of her dirty talks she couldn't come up with new things, so she kept on repeating things she had already said. She had to hold her tits with both hands as she was feeling pain because of the enormous size which was juggling up and down with all her motions.

She didn't have any quad strength left anymore and after her third massive squirting orgasm she found her cunt overtly sensitive and no more physical strength left. So, Reggie said, "If you gave up and can't bring Mark to his well-deserved orgasm then I would suggest get up and keep on walking back to your home."

This was what brought her back to reality, what was at stake, Michael's life. Hence, with a newfound strength, she continued fucking him and tightened her cunt muscles around his cock. This brought immense pleasure to Mark, but on the flip side, it brought her back to the peak of her fourth big O.

If she came again, she did not know if she could continue, so the idea was to keep the constant speed with the same rhythm and tightness in the muscles. She was struggling to hold off her orgasm, but she was getting the feeling that Mark was also trying to hold off his as well.

Now it was just the game of who gives up first. Mark tried his best but eventually gave up and she milked his cum with continuing to go up and down. Within next few seconds, she had milked every single sperm that he could have ejaculated but she kept up and down for the next few strokes before she rose and there it was the fourth giant squirt out of her cunt which looked like it would never end.

But over the next few seconds, as it subsided, she could no longer hold herself and fell on top of Mark. Fortunately, this time she was awake, but she could clearly see stars on the roof of the room. Mark lifted her and kept her aside as both were heavily panting.

They told her to take a shower and get back they'll order lunch till then. She took a long hot shower then dried herself, applied the regular moisturizer and her slut makeup pack which they had placed there, and she applied it again.

She came out naked, as she did not know whether she should wear the robe. When she reached the living room, there was a waiter setting up their food. When he saw her, she got self-conscious but kept calm.

Reggie spoke to the waiter, "you know my man, she's a married slut. Her pathetic husband had a micro-penis and couldn't satisfy her needs, so she fucks whoever she finds. Jess, tell the guy about your hubby."

Things were getting out of hands now, but she kept going, "yeah he has a micro-penis like even smaller than Reggie's middle finger and to make things worse he comes in less than a minute," she lied.

"I tell you what Jess, why don't you give this lovely man a nice blowjob, swallow his entire cum like a cum guzzler you are and then we all can start with the lunch."

With no choice left, she went down and started unbuckling his trousers. Within minutes, his hard cock sprang free, which was the size of Jason, so when she started sucking him off, it wasn't too difficult, and she could take his entire cock in her throat.

With the skilled use of her tongue, the waiter came hard shortly, and Jessica focused hard to swallow his entire load. Jessica had always enjoyed giving blowjobs to Jason, so over years she had become quite skillful in that regard. The only problem was the four black guys in the room. Their cocks were ridiculously huge, and she had no experience with those sizes. The waiter left shortly, thanking all the guys.

Not much happened during lunch they all ate in a relative silence. She enjoyed this silence and was hoping for things to just end like this. After lunch, they gave her another gallon of water to finish, which now was even harder to pull off with a tummy full of food. But somehow, she did it. They watched TV for the next hour for the food to settle down. No one wants to throw up by trying something stupid instantly after a heavy lunch.

Turning the TV off, Reggie got up and told Jessica to get ready for her next task. Now suddenly she felt an urgent need to pee, so she asked permission to use the restroom. Which was, of course, denied. Reggie told her she can use the restroom only after successfully completing the next task.

With little options, she got up and tried to control her bladder. Reggie explained the next task which was for her to crawl up to Terry this time in same bed, same situation, but difference being she'll offer her asshole to him.

At least they gave her a tube of lube for this task. This brought shock to her as she had never had anal before, but she knew there was no point in complaining to them. This time the level was up as they told her she can cum as much as she wants but she cannot pee without permission.

Now she crawled up to Terry and said similar things to him as well. After the boxers were off and his cock was fully erect by some first jerking and sucking. It relieved her that the size of his cock was smaller around 8 inches, but girth was around 4 inches, which was going to be a problem.

She poured more than a generous amount of lube on his cock and applied more than enough on her asshole and as a warmup she tried inserting her fingers which initially was a problem but then with help of all the lube, she could enter three fingers and spread them as well.

After a while of being satisfied, she climbed on and faced Reggie. After long and heavy breathing and a lot of strength, the head was in. Which was the most troublesome part. Over next few minutes, she tried to adapt to the girth of his cock and then started the rhythm. Few more minutes and she was all the way in. She took few more breaths, but her bladder was killing her.

With a lot of focus and supporting both her tits with her hands, she started the ride. As the orgasm started building a few minutes later, she had forgotten about the need to pee. Entire time riding Terry she was talking all nasty things about her and her husband.

It was when her orgasm reached the peak; she realized it would be extremely difficult to cum and not pee. So, she tried holding off on her orgasm for as long as she could but suddenly it was just out of her control, and she came hard so hard that her body wouldn't stop shaking and her ass still filled deep from the cock and spray of fluid gushing out of her cunt.

She somehow, she did an excellent job holding the pee in but as she thought her orgasm is over, and she had controlled her bladder and then it happened. Her bladder just gave up. Terry's cock all the way up her ass when she started peeing on top of him.

It all was just too much for her and she just gave up. It was then that all her emotional resolve was over, and she started crying loudly out of embarrassment and trying to be tough throughout the day when she was most vulnerable.

Reggie waited for her to calm down and when a few minutes later she was no longer crying he said, "I am not a cruel person, since you have been a good sport so far, I'll let this transgression slide with a punishment pending. You'll get that tomorrow for now continue riding his cock like your life depends on it."

When she heard tomorrow is when she realized she would not meet her brother but would have to stay here all night long. Hence, she continued riding Terry. 10 minutes later she was sweating like she just came out of a shower; her quads were shaking from the workout she was getting.

She had one more massive squirting orgasm, and when she was about to give up and thought she didn't have enough strength left in her is when she felt something, Terry was about to cum. This gave her some extra adrenaline rush to push faster for a few more strokes.

Twenty fast and deep strokes later, Terry dumped all his loads in her asshole. After he came, she climbed off him and fell next to him. There was no more physical strength left in her to fuck anyone, not at least without some rest.

Terry took her to the bathroom, and they both took a nice, long shower. This gave her some of her energy back. By the time they got back out in the same bedroom, room service had cleaned everything and looked like nothing nasty had happened in that room. Reggie gave her a bottle of Gatorade to drink and regain some of her energy.

After a few more minutes of rest, it was David's turn, and he also wanted to fuck her asshole. Good thing was he will do the work. David fucked her asshole for what looked like a little over 30 minutes, doggy style. David exhausted her as he was also about 10 inches long and 3 inches girth.

She had four more massive earth-shattering squirting orgasms while David fucked her. She had never thought that it was possible to have so many orgasms in a single day.

They again gave her some rest, and the Reggie fucked her crazy. He was just a little over 11 inches or a foot long with same 3 inches girth. She did not know that Reggie had taken Viagra before he started his share of fuck.

This mammoth of the fuck session went a little over an hour and a half. He fucked all 3 of her holes during this session. She had over fifteen orgasms just during Reggie. She was just too tired to even move. They told her to suck him off.

The glorious news for her was that she was by the end able to deep throat 10 inches from his giant cock. When Reggie got off her, she was just a dead meat now. They knew she was done for the day there was no way for her to continue, no matter what the stakes are.

They had fucked her beyond her limits, or let's just say beyond anyone's limits. Terry was the one who was now feeling bad for her because he knew she had no choice, and she was trying all that she can. He fed her dinner while she was lying on that same bed gave her some more Gatorade.

After they took her to the restroom where she did her business. By the time it was 8:30, she was just gone, never slept this deep in her life.

Reggie called Tyrone and updated about the entire situation. Tyrone was not happy that they gave her so much rest and the guys were giving her too much liberty. But after Reggie explained to him that this is not the first time that Tyrone will get to control her as his toy.

Any toy is only good if it's not broken. If overused the toy will just break it and then it's no good. The choice was his if he wanted her to be dominated only for this weekend or long term. Tyrone understood the point and gave Reggie the full command to do as he wishes with her for the rest of the Sunday if she's sent back around 10pm.

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Jessica opened her eyes and looked at the clock on the bedside table and saw it was already 7:30 in the morning, which was an awfully long sleep she has got. All the guys let her rest so they could enjoy her better on Sunday.

As she sat up, and realized that all the muscles in her body were very sore from the heavy workout she had received yesterday. She was still completely naked and saw Terry walking up to her with a glass of water and gave two pills along with it.

She looked at him questioning with her eyes what they were for, but all she got was not to worry, it's so she feels better. After taking the pills and finishing the entire glass of water, she was told to get her daily morning routine finished and be out all dolled-up by 8:15.

She went to the bathroom and went on with her routine. She could not think straight anymore. When she was back in the bedroom with same make up as before and still completely naked and saw the clock and it was 8:10 already.

Reggie called her to the living room and there was breakfast already setup. They had their breakfast in relative silence and when she ate everything again, they gave a gallon of water to her to finish. Hydration is necessary, as told to her by Reggie.

It pleasantly surprised her at how she was being treating this morning by them and after breakfast all of them watched some TV till 9:30, which was to let to food settle in. It was then they told her that the day must begin.

By the time they reached back to the bedroom, Jessica realized her muscles were no longer sore, and felt like she had some extra energy. Must be the effects of those mysterious pills, she thought. All four of them had taken blue pills after the breakfast, which she knew was not a good sign for her.

Reggie has given her a professional-looking suit with some fake glasses, and she was told to put her blonde hair in a ponytail. When finished with the dress, it was completely like she was playing a role in a porn movie.

They already instructed her what exactly she had to do once she returns to the living room of the penthouse. She took few deep breaths and convinced herself that she could do it, since she had already done too much. She figured these guys want to do a role play this morning.

Per the instructions, she left the penthouse, waited outside for a few seconds, and then knocked back at the door. Mark opened the door and asked her to come in. Once she was back in the living room, Reggie asked, "who are you, girl? What do want from us?"

"Well, my name is Jessica Peterson and I teach physics at the university, but the thing is as well I pretend to be from the outside, from inside I am a complete whore."

"If you guys can pay me $500 each, I promise you I'll give you time of your life", she just couldn't understand why these guys would consistently insist on mentioning her full name and where she works every time like they're meeting for the first time.

"If you're a whore, why are you dressed so eloquently?"

"Well, I am coming directly from work. Sometimes I get too horny at work, and I know I won't get anything at home since my husband has zero ability to satisfy my sexual desires. Do we have a deal?"

Reggie pretended to think for some time and then said, "Okay. You have a deal; we'll even pay you in advance, but remember whore, if you accept the money from us you have to do whatever is needed to satisfy all of us."

She nodded. They completed the deal. All four of them took out $500 each from their wallets and gave it to her and told her to count the money and acknowledge that you have received $2000 to fuck four guys till the time they're thoroughly done with you.

She counted the money and said, "Looks like everything is in order. I have received $2000 from four guys to fuck me all they want."

She put the money inside her suit jacket pocket and got a nod from Reggie, suggesting it's time to begin. She did the same thing again, started dancing, pretending like there was some sexy music playing. This time she took her time around 15 minutes in her striptease and threw each article of clothing towards the guys.

Once she was now completely naked, she walked up to Terry first and said let's see what you've got here. By the time she helped him get naked, his cock was already rock hard. She guessed the Viagra has worked its magic already.

For next few minutes, she spent time in getting used to that huge and thick cock in her mouth. With some extra pressure on the back of her head by Terry, her lips were now at the base of his cock and nose pressed on his pubes.

He kept her head pressed deep for a few seconds and as she was running out of air that he let her move up. He now just was laying back on the couch with eyes closed and focused on the wonderful deep throat blowjob he was receiving.

Jessica was so focused on using her throat muscles and her tongue on the blowjob that she didn't realize someone had spread her legs real wide. Soon she felt the cool lube been poured generously in her asshole. And in the next few minutes there was a huge dick ball deep inside her asshole. Another guy sat next to her body.

She was so focused on providing the best blowjob possible and trying to enjoy the wonderful anal that she didn't notice when that guy placed his hand in between and inserted two curled fingers inside her extremely wet cunt while rubbing her enormous clit at the same time. She was too full now, with fingers touching the most sensitive part of every insertion.

She remembered the instructions that if she does whatever is told; she has the free pass to cum as much as she can. She came hard on the fingers, squirting lots and lots of fluid out of her cunt while grunting loudly since Terry had put all the pressure on the back of her head to make sure her nose was blocked.

Unable to breathe at all made the orgasm extremely intense, her entire body was desperately shaking violently now both because of the intensity of her orgasm and the lack of oxygen in her body. As she thought she would just pass out, he pulled her head up, and she was gasping for all the air she could take to recover while looking up directly into his eyes.

It was all so intense that she had lost every other thought or worry in her life and was completely lost in the most extreme lust she felt right now. Her body was still shaking, and fluid was still squirting out of her cunt when she yelled out loud, "oh my god! Fuck me harder put that big hard black cock in my cunt. Please fuck that whore cunt of mine. I need one more cock in me. Fuck me."

She was lifted by the hands behind her with the cock still buried balls deep up inside her asshole. They carried her to the center of the living room, where they have now placed a huge mattress. The guy behind her just laid back on his back with her on top.

It was Mark's turn now as he took a place in front of her with his rock-hard cock pointing at her cunt opening. As she looked further, she could see both Terry and David jerking off hard while looking at her, which made Reggie balls deep up her asshole. Within the next few minutes, Mark was also balls-deep in the cunt and the pressure she felt was immense.

All three of them got into a perfect rhythm and the speed which was increased even further. She was no longer in control of her body or mind. This time she was genuinely shouting nasty things which she meant for real, "Fuck me harder you motherfuckers! Harder... more... Oh fuck yeah right there, keep going deeper and harder. Oh, my god! I am going..." she came real hard again, squirting her fluids all over Mark's cock and it became more intense since he never pulled out or slowed down.

She was on cloud nine. This went on for a long while and she must have had at least six or seven extremely giant orgasms before both guys switched, and now David and Terry were fucking her. All four of them kept on switching and there were cocks in both her holes the entire time.

She had lost count of how much she came now; her holes were in constant stimulation. And then when it looked like forever that she was sitting kneeling at the center of the mattress and all four guys came on her body. They covered her in jizz all over her face even some were on her eyes, lips, chin and dropping, with already a lot on her tits.

Reggie demanded her to sexually rub all the jizz across her body. She did as commanded, rubbing it sensually as if it was some sexy moisturizer and kept ongoing on her tits as well to make special mention of pinching her nipples.