Teacher's Dilemma Ch. 01

She told him that there's nothing to help right now, he can enjoy some news and she'll let him know when dinner's ready. Not that she didn't need help, she just needed some time to think of an excuse to be out for the entire Saturday and Sunday, since she didn't know what would be happening.

Finally at dinner, she said, "hey hon, I forgot to tell you some of our college professors have planned a camping trip tomorrow morning. We're planning on some astrophotography, maybe late at night or early morning Sunday. I have planned to visit Mike directly from there and probably be back Sunday night."

She was nervous about his counter questioning, but he just didn't think of anything about it and told her to have fun on her trip. Now her last hope of not pulling through with this deed vanished. She had to go through with it.

Her alarm woke her up at 6:30 on Saturday morning. Reluctantly got up and went to the bathroom for her daily routine. Soon she's done with shower and applying the moisturizer and regular make up. She had kept her slut makeup in her purse to be applied in the hotel restroom.

She didn't wear a bra under her regular shirt since, after changing into her slut dress, she won't be needing a bra, anyway. Thong looked very weird to her since she's not used to wearing one. She put jeans on made sure she looked presentable.

Once sure everything was with her, she put on a regular sneaker shoe on and told Jason that she was leaving and went on to her car. It was already 8 when she left the house, because she knew she wanted to make a stop at Starbucks to gather her thoughts and think through her plans.

It was 9 when she parked outside the hotel and gave her keys to the valet as she grabbed her large red purse, which now had her dress for the rest of the day. Before leaving the car, she switched her shoes and was now wearing the slut heels.

Now in the hotel lobby, she directly rushed to the restroom and went to a large stall, which was empty. Once in there, she changed her clothes and was now wearing the very slutty red tube top dress without the bra. The dress was so tight on her body that it highlighted her large 36D breasts well.

She never realized how big her breasts can appear until she wore this dress and looked in the restroom's mirror. Anyone who would put enough focus on her breasts would see those significantly larger nipples through the dress.

She tried to adjust the length of the dress, but there's so much she could do without exposing her tits to the world. Hence, she agreed that this should be the right look for the task.

Now she started with her heavy makeup, which she had seen in the same porn movie from where she picked the dress. She now had almost same darkest shade of red lipstick, which was also shining. She now had a heavy makeup on her face. Anyone seeing her would not have to even guess what her profession was. She was a whore for anyone who would see her in this attire.

Jessica had put everything remaining in her purse, including the old clothes. She took a few deep breaths and tried to rehearse what she was going to say once she meets whoever was in that room.

As she was leaving the restroom, the door opened, and a woman walked in, in her 50s and if you would like to judge her, she was rich as fuck. She looked at Jessica from up to down saying nothing she went to the stall but made sure from her expressions to translate that she knew a whore when she sees one.

As she left the restroom and walked towards the elevator, it appeared as if all eyes on the floor were on her. She was now excessively self-conscious. Once in elevator she pressed 21 and tried to ignore all the eyes she had on her.

Somehow, her face was also turning into the color of the dress. She couldn't remember being more embarrassed in her life. Once she reached at the desired floor, she looked at her watch and saw time to time was 9:45. She still had 15 minutes and didn't know if there would be a punishment for being early, but she didn't want to take the chance.

She found the room and waited outside for few minutes until it was exactly 10 and she took a deep breath and swiped the key card to open the door. In she went to the world of unknown. There was no going back now. She had to go through with the plan.

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As she walked into the room, it was a penthouse. She was walking nervously as well as cautiously until a loud voice behind her startled her. "What the fuck, who are you, lady? And how the fuck did you enter inside the room? Drop your bag and turn around with hands above your head unless you want to be dropped dead right here."

She dropped her purse instantly without thinking because of the panic and sudden rush of adrenaline, because of the fear of death. She turned around and saw a large black man pointing the gun at her. She felt extremely scared. This was not the situation she had prepared for and thought that they'll shoot her dead here for trespassing.

This man must be at least 6'5" and excessively muscular, in his 40s. He had shaved his head completely.

"Answer me, you fucking whore. How the fuck did you enter this room?"

"I... Tyrone gave me the key, and he told me I'll get what I need right here."

"And what the fuck do you need."

"I... I... needed some fantastic fucking from a real man." She thought she was being as sexy as the girl in the porn saying same dialogue, but she just appeared as if a news broadcaster was reading the lines from a teleprompter.

"There's no one in this room who needs a whore, we're all happily married men," the guy said, showing the ring on his hand.

"No sir, you're thinking it all wrong. I'm not a whore, I'm also a married woman, just the difference is I'm not happily married. I mean, now and then I need simply good fucking to satisfy my cravings and that is why Tyrone sent me here." this time she appeared less nervous but still was really afraid while trying to convince him.

The guy put the gun back in the pocket of the large robe he was wearing and yelled, "hey guys, everyone come out there's a really interesting situation going on here and I need your help to decide."

Now Jessica was mortified and did not know what to do as she saw 3 more giant black guys coming out of the bedrooms in the penthouse. As they saw her and looked up and down, scanning her body like an x-ray machine.

All of them went to the living room of the penthouse and sat on the couch as she was standing in front of them. One guy had a MacBook Pro in his hands and was wearing AirPods like he just was in a meeting.

The same guy said, "If you say what you want, and it's true. Then we'll need to know that you're a genuine person and not some whore that Tyrone hired to get the deal done."

He continued, "I would ask you a few questions, Terry over there," pointing towards the guy with the laptop, "will search for all answers you give. If any answer is incorrect, then we'll assume you're some hired whore and we will throw you out of this room and we'll also alert the police because we don't want to get in trouble under prostitution laws of this state. Nod if you understand what I said."

Fear took over Jessica because she knew they would ask more personal questions now and she would have no choice but to answer honestly. So she nodded.

"What is your full name? If you're not a whore, what do you do for work?"

"My name is Jessica Peterson, and I am an assistant professor at the university, and I teach physics."

She saw Terry typing something on the laptop for a few minutes and then he nodded, as if he had verified this information.

"What is your husband's full name and what does he do for work?"

This terrified her completely, telling her info was one thing but exposing her husband like this was extremely uncomfortable for her but there was no choice she had to pull through, "His name is Jason Peterson and he's Vice President marketing at DarkWeb which is a cyber security company."

Again, after some typing, Terry gave a nod.

"Okay, so your info checks out. But that's not it. I want you to repeat this same information again. After that, explain what you want from us. And remember, if it's not sexy and convincing enough, you're done. If we're not convinced of your details or your desire, you're out of here."

Now this was getting very weird and something she had not prepared for at all. What should she do just leave from here and pretend this never happened, but what about her brother? After thinking a while, she knew she had to go ahead with this, but what should she say to convince them? Then she realized one thing every man is conscious about, the dick size. And she knew exactly what to say.

She looked up at them directly into the eyes of the guy who was in charge and said as seductively as possible for her, "My name is Jessica Peterson and I teach physics at the university. My husband, Jason Peterson, is a Vice President of marketing at DarkWeb, which is a cyber security company. We're married for almost 9 years."

Taking a deep breath with fake sexual moan and showing her wedding ring, "but the problem is that I am never satisfied sexually with him. He has a very tiny dick and ends up coming in less than 2 minutes," which was a total lie.

But she kept ongoing, "that is why when I met my ex-student Tyrone and confided in him, I am sexually frustrated with my husband and just once I need a fucking of the lifetime from a real man just to get my frustrations down."

Turning her head while looking towards others as well, she continued, "he gave me the key to this room and told me I will find some real men here who would show me what real fucking looks like."

She showed as if this was the truth, but inside she just wanted to run to the nearby window and jump down for what she had just said. She could not believe that she had just humiliated the love of her life in front of these strangers.

"Looks like you were searching for some big black cocks, huh? Well, you will get some only if we have one understanding."

Now relaxed, he laid back on the couch, "till the time you are here you will do exactly what we say without question or hesitation, and you'll leave this room only when we give you permission to leave that means when we're completely done and remember it could be awhile so know before you agree."

He could clearly see the change of expressions on her face. "At any point in time we hear you say no for any reason we'll throw you out of this room no matter what you're wearing or let's just say not wearing. If you agree with all conditions, then repeat them in exact tone as you expressed you desire before otherwise you can leave now."

She knew now it was too late to just leave, so to get it over with, she said in the same seductive tone, "I really need those big black cocks in me. I will do exactly whatever you guys tell me to do with no question or hesitation and will only leave this room once you guys are thoroughly done with me and command me to leave."

Somehow the voice sounded alien to her but kept ongoing, "if I say no or show any kind of hesitation with any demand, I agree to leave this room completely naked to go home."

Now she was numb to her feelings. This was too much for her. Only goal for her now was to do whatever was requested and once done to get the hell out of here and hope that she's done with Tyrone for good.

Somewhere within her head, she knew this was not the end, but just the beginning of his demands from her. He won't just let her go with this one thing. But that was for later.

"Okay then, let us introduce ourselves to you then. My name is Reggie, that is Mark and that is David. You already know Terry," said Reggie, introducing everyone.

"Now you need to dance for us and strip one article at a time and imagine in your head as if you're a stripper in a strip club and a sexy song is on. Take your time no need to rush the stripping we want to enjoy the dance we have all day for the action. While you're dancing, explain to us your sexually frustrating encounters with your husband and how you want that to be fixed by us."

She instantly cringed at the last part of the demand but knew better to say anything or even show hesitation at the very beginning of the day. She was never an excellent dancer, but she started moving her ass while bringing her hands up and playing with her blond hairs beginning her sexy dance without music.

It was weird, but she thought of a sexy song in her head and tried to get some sort of rhythm. Now she had to make up sexual stories with her husband to show him as a complete loser, so these guys get a turn on when she'll praise them.

So, she began by saying, "One-night you guys, I was so horny that I swear I could have fucked anything living or dead and my pathetic husband came to the bedroom, and I immediately jumped on him," she said while trying to dance with some sort of seduction.

"And he said honey, you're so horny today I'll give you some real dick. I knew what to expect from my years of marriage, but I was so horny that I wanted it to be real." now she was getting in some sort of rhythm.

"I told him, Jason, I just want you to last long enough so that I can have at least one orgasm with your fucking, then you can come. And he said, don't you worry, you'll not have just one but multiple orgasms today."

As she said that, she started rolling her tight tube top dress down. It was now below her boobs and her entire large 36D boobs were out in the free world for all 4 black guys to see.

The tube top dress was just around her flat abdomen, and she stopped it there and continued with her so-called dance, "I was so horny that within few seconds we were both naked and I was on top of him. His pathetic small penis was completely inside me, but I didn't feel a thing. But since I was so horny that I kept moving up and down fucking myself and thought about getting the orgasm I so desperately needed."

Now while dancing she started pressing her tits seductively as if giving an offering to these men and continued, "but I think it was less than a minute or maybe a few seconds more than a minute and I knew he was about to come."

She was breathing a little heavier now but continued, "I increased the speed in desperate attempt and yelled at him don't you dare cum before me you pathetic bastard, but it was all for nothing," she acted well enough to make it believable.

"He just came right then when I was about the reach of my peak. But the orgasm was still far enough. I yelled at him in frustration and ran to the bathroom and while looking at the mirror started fingering myself to orgasm, which was becoming the usual routine."

She knew this was not true. Their sex life was not extraordinary, but she has had orgasms with Jason occasionally. He was not amazing, but he was also not pathetic like she had to tell so that these guys could get a turn on, and they could end up feeling great about themselves.

As she was sliding the dress below her ass Reggie nodded his head as if to say continue with the stories, so she made up another story on the fly, "one time on the night of my birthday he asked me what I want tonight. I told him; I just want an orgasm with you, Jason, nothing more. Can you do that for me? He said yes definitely."

Now her dress was off, and she threw it towards Reggie as he took the dress and started sniffing it. She was now dancing just in her thongs and heels and continued, "again we were naked in few minutes, and he started humping me missionary style and before I knew what happened that pathetic bastard came in me. So much for the birthday gift, I had to follow my same routine and finger myself to come."

She had her thumbs around the thong and rolled it down. As the thong was off, she threw it towards Mark. He did the same sniff test as Reggie and exclaimed, "this bitch is horny as fuck".

After hearing this, she brought her fingers to her pussy and found it to be extremely wet. She was getting horny making fake stories about her loving husband and stripping in front of strangers. She instantly felt a rush of guilt in her body, but kept on continuing the dance.

As she was about to remove the heels Reggie said, "leave the heels, they're fine. Continue your dance and show us how you finger yourself to cum. Just remember when you're about to cum you have to ask us permission."

With the most arrogant smirk he said, "only after all 4 of us have given you the permission, can you cum. Stop, slow down or cum without permission and your naked ass is out of here. Understood."

She nodded and Reggie continued, "and we want that rigorous and desperate to cum fingering, not that slow passive one. Reminding you again so it's absolutely clear, don't cum without explicit permission from all four of us and don't you dare slow down the speed without explicit permission from all four of us."

And with the continuation with his smirk, he said, "we will grant permission only if all four of us feel that the story you tell while rigorous fingering about your pathetic husband is good enough. Now start."

Extremely aroused by now, Jessica did not know why this was happening to her. She was telling stories about her husband that were not true, extremely degrading, and she had to up the ante with these stories.

She had no time to process things as she spread her legs a bit more to gain easy access to her pussy. With her middle and ring finger now completely inside her pussy and her thumb rubbing her clit with all the physical strength she had, which made her orgasm buildup much faster than she expected.

The story was the worst part. How could she make it much worse than before and suddenly a scene from movie Deadpool came flashing in front of her eyes and she knew where to turn her story as she continued running out of breath and the next story would be a step up?

"One time I remember it was women's day and same as always, that pathetic looser came much before I could feel anything. This time I got much more angry than frustrated. So, I got up and from one of my bedside drawers I grabbed a strap-on, put it on," her mind was screaming at her not to do it.

"This one had a friction that was set directly on my clit, and I attached an 8-inch enormous dildo to it. I grabbed a KY lube, and I yelled at him if you don't want you naked ass out of here, you better be on all fours NOW without wasting anytime."

She continued while trying the breath properly, "I will show you pathetic fucker how real men fuck their women. He got so scared that he was...", and she felt lost somehow the speed of her fingering and the visuals of imaginative story had turned her on beyond the limits she knew.

She was about to cum, and she had never had such an aroused feeling before in her life. From her trembling voice and desperate attempt, she begged, "I am about to cum guys, may I please cum".

Without even looking or asking anyone, Reggie replied, "Absolutely not. Keep up with the same fingering you did not yet complete your story. We'll have the voting only after you complete your story. Don't cut out on details. If we felt like details were missing, you might have to start over with another story."

Jessica was desperate to cum now and knew she can't hold on to it much longer. She started taking deep breaths trying to calm herself down, but it was not much effective since the fingers were ravaging her pussy along with the extreme pressure by her thumb on her now huge and erect clit was making things even worse to hold on to the orgasm.

Only way out was the story, so she continued, "He got so scared that before I knew he was on all fours. As I climbed up, he begged me not to do it. I swear I'll try harder next time. But I was so furious that I yelled at him, shut the fuck up you weak ass bitch and let me show what a real man is supposed to do."