Teacher's Dilemma

Author's Note: If you're searching stories in this category, then you know what's coming, but if you're offended by such stories, I'd say skip this story since it has blackmail and non-consensual sex. This is a fictional story so trying to find reality in it would be like trying to find logic in Fast and Furious series.

I've already given a fair warning here. Constructive criticism will always be welcome so that I get to improve my writing.

EDITED VERSION: Fixed some of the annoying grammar issues.

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Main Characters:

Jessica Peterson: Jessica (32) is an assistant professor at a prestigious university & teaches physics. Married to Jason (9 years), love of her life since when she was a teenager. Michael is her twin brother.

Physical Attributes: White woman with blonde hair that goes well below her shoulders. She's tall, 5'11", keeps her fitness but has real nice curves just in right places. Bra size - 36D.

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Tyrone Williams: Tyrone (21) ex-student at the same university. Expelled after an incident reported officially by Jessica. Highly intelligent, technology innovations being his strength. He still holds a grudge against Jessica. He is the brother of the biggest criminal gang in the city. His brother forced him to work full time with him after his expulsion from the university.

Physical Attributes: Black man, handsome and loves to remain well dressed. Height 6'2", loves to be in shape, keeps lean muscle body.

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Jason Peterson: Jessica's husband (38) is Vice President of marketing in a cyber security company, DarkWeb. He gets to travel a lot because of his work.

Physical Attributes: He's a redhead white man, just a little taller than Jessica at 6'. Fairly good looking for an average person.

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Michael Clark: Michael (32) is Jessica's twin brother. Had criminal history throughout his teenage. When arrested by FBI on an attempted murder case, agreed upon a plea deal and helped them arrest the entire Latino gang (only rival gang to Tyrone's at the time). In return got reduced sentence in minimum security prison, currently on parole.

Physical Attributes: White man with blonde hairs, dangerously skinny with height 6'2".

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These are the main characters you need to know; I will explain other side characters as they come and go in the stories.

This story starts slowly and could escalate quickly. Overall length could be long for some people's taste.

The whole idea of this version of the story is to provide an emotional journey along with the character's development. I have tried and will continue to try having characters that have shades of right and wrong in them.

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It was a pleasant Sunday morning, not so cold for November. Jessica was driving to meet with her brother, which was her weekly routine since he was on parole. She wanted to make sure he's on the right track and didn't end up in prison again.

Every Sunday, she used to spend the entire day with him, having all 3 meals with him and long chats, which was mentally relaxing for both. Since it was an hour of drive to her brother's place, her mind raced back to the time when her mother divorced their father because of his abusive behavior.

Their father was an alcoholic and, when drunk, would lash out at his family. Michael used to always save his sister and mother from him and always end up getting beaten by him. Later he would joke, I'm fine being the punching bag if he doesn't lay a hand on you two.

Their mother was stuck with him because she was a homemaker and relied on him for the finances. But when they were 16, one incident left Michael in ICU, which was a wake-up call for her and she left with her children and divorced him. Out of fear, she pursued no legal case against him.

With no finances and family struggling, Michael entered the world of crime, and soon became a henchman for Latino gang, only few non-latinos could rise in ranks. He made sure there was food on the table and Jessica gets to continue her education.

She remembered once when he said to her, "Hey Jess, remember this family relies on you, not me. Make sure you study hard and make something of yourself. You are the one who will take us out of this shit. I'll try to survive to make sure I see you successful."

That memory brought tears in her eyes, because throughout their entire life he made sure that nothing happens to her, and she always felt like she never could return the favor.

Before she could pull herself out of memory lane, she had arrived at her destination. She parked in front of an ancient building where he lived, a smallest studio. Michael refused any financial help from her. He felt like it's his responsibility to be the protector, not the other way around.

She composed herself and left out of her car to meet her brother.

She knocked on the door. When he opened, it just brought back a sense of how much he was struggling in his life. He was a complete mess and so was the small studio in a building which could crumble into pieces with a minor earthquake.

As she entered inside and went to the small area reserved for the kitchen with the food, she had brought with her and said, "Michael you need to do some cleaning around this place, you can't just live in a mess like this".

He just smiled and said, "I have a sister to help me once a week. Why would I do the cleaning then?"

She just ignored that statement and cleaned the apartment as much as she could before heating the food in microwave and served it for both. As they were eating the breakfast and chatting about their week as usual, Michael said, "Hey Jess, I always get so sad that mom never get to see what a wonderful life you have made for yourself".

Now he was serious and continued, "she suffered her entire life and before you could even graduate, cancer took her from us. But I know she's looking down from somewhere so proud of you."

She knew he was holding on to his tears and knew that he always wanted to be this alpha-male in front of her and throughout her life she had never seen him cry. At least she doesn't remember it.

It was when he said, "Sometimes I feel like I have completed my purpose in this world. I just don't know what to do anymore. You don't need me, sis, I just don't understand what to..." and he couldn't hold anymore and started crying.

It was like the floodgates were now open. All those years of suffering were now flowing with his tears. Jessica couldn't hold her tears as well and both cried for what seemed forever.

Once they were normal, she said, "Don't you dare say that again. I need you more than ever. I can't imagine my life without you, Mike. Whatever thoughts are going on in your head, remember if you do anything stupid, I will follow you wherever you are, instantly. I can't let you go, and you can't leave me all alone, not after all we've been through."

She knew Mike was going through severe depression and needed professional help. She just didn't know how to bring it to him without offending him. But it was now or never a situation, so she said, "Mike, I think you need help. I mean professional help. Please, for once listen to me and see this..."

Before she could finish her sentence, he yelled at her, "so I open up in front of you and you think I'm some sort of nut case"? Before she could respond, there was this extreme anger in his eyes, but there was something else as well, disappointment.

She was the only person in his life who thinks he's not mentally stable, which somehow meant for him that if he agrees he needs help from a shrink, she will no longer have any respect for him.

In this anger, he jumped from his seat and went to the door, opened it, and yelled at her, "Jess please leave before I do something stupid that I'll regret rest of my remaining days".

She wanted to say something to him, but when she looked into his eyes and realized that saying anything would make things even worse, so she left.

Once in her car, she couldn't hold her tears and cried again for what seemed like forever. Only worries she had was what if she left here and Michael did something stupid, something she just didn't want to bring to her mind as well.

She did not know what to do, hence she thought to talk to one of the clinical psychiatrists at her university, her good friend Rachel. She would recommend her something beneficial on how to approach this delicate situation.

Resigned to the fate, she drove back to her home but somehow her mind was in such an emotional roller coaster that she needed some break before she goes back home to her husband's questions about why she's back early. So, she planned to stop at the Starbucks on her way and gather her thoughts.

She parked outside a bigger Starbucks, which had open seating area, which was perfect since she can pick a spot away from the crowd to think straight, alone without having prying eyes if she ends up crying again. She ordered a Frappuccino and found a perfect spot of which was at the corner and would be out of view from people unless someone specifically looks for her.

While sipping the frozen drink, she was trying to calm herself down and didn't even notice that someone had taken a seat opposite to her. She looked up and saw a black guy sitting and thought she knew him but somehow couldn't remember, at least not till he said, "How's everything Miss Peterson"?

She thought, "Tyrone? What's he doing here and how did he know where exactly I was?"

Before she could say anything, he answered her questions as if reading her mind, "Don't bother answering, since you're thinking about how I found you? I just followed you from your home all the way here. I was trying to find you alone to talk and was pleasantly surprised when you left earlier than usual and stopped at Starbucks."

She thought, "Why was he following me? Earlier than usual? How long has he been following me?" But this won't help. She needs to be strong in front of him, so she said firmly, "What do want Tyrone and why are you following me?"

"Straight to the point I like it," said Tyrone with a smirk, "Well you know Jess, I always wanted to do something in academia and help the world with my knowledge but it's difficult to do when your brother is a gang leader and wants your help to expand it."

Looking directly into her moist deep blue eyes, he continued, "I tried everything to keep him at a distance, by doing what he wanted so that he'll leave me alone and let me continue my studies."

Grabbing her drink and taking a sip from it, he said, "until you decided they should expel me, and for what? For teaching that whore a lesson, who couldn't shut her mouth about my brother because she fell in love with him?"

He paused a few seconds to let things sink in and then continued, "you know something, I didn't want to do it, but I didn't have a choice, you see when my brother asks you to do something it's never a request. But instead of trying to understand my situation, you had to get me expelled."

She could see anger rising, remembering the past. "YOU KILLED MY DREAM. I knew I had to get back at you. I could have done anything to you or your family, but that's shortsightedness and you know me I don't make any major decisions out of anger. Patience is key until I got the idea and boy what an Idea I got."

With all that she had faced today she was just not in the mood with all these riddles, so she said, "I am not in the mood for your stupid stories and what happened to you was because of the decisions you made, it had nothing to do with me. What did you think that there won't be any consequences of what you do?"

"Funny, I was just looking for the right word, CONSEQUENCES. What did you thought Jess, there won't be any consequences for what you did?"

"Don't waste my time Tyrone, I have been through enough for the day so get to the point."

"See, Michael is still on parole, and you know who is the parole officer? Let me answer that to you, Luis Sanchez. His earnings took a massive hit when your brother was a snitch, because he was under Latino payroll and since they're now gone, my brother doesn't give a shit about him."

Now in a much calmer voice, he continued, "so if Luis finds anything against your brother, he will not hesitate a second and put him back in prison. I would say he would even make sure your brother ends up in same prison cells as the Latino gang members are. How long do you think your brother will survive?"

She was in complete panic mode, which could be clearly visible on her face. There was no doubt he wouldn't survive a day. But pretending to be strong, she replied, "but my brother did nothing illegal since he's out."

He pulled out something from the pocket of his jacket which looked like photos and threw them on the table in front of her. "Consumption of hard drugs while in parole is completely illegal and would be a perfect way back to prison".

She looked at the photos it looked like a montage of photos from different days, which meant that he was back on drugs again. He completely defeated her now, and she did not know what to do anymore. This day couldn't get any worse, she thought, but struggled to form any sort of words to respond and just kept on looking at the photos.

"Now if you're thinking, how could he even have money to buy the drugs then let me help you with it, I told my guys to provide it for free to him. Sure, they kept recording his activities, so I have videos of the pictures that you're seeing. His drug test will come up soon anytime, so he'll be caught," he said coldly.

"Please don't take your anger on him. He had done nothing to you take it on me. Please help him, he can't go back to prison, please," she begged him, crying for help.

"Well, you took the only thing I wanted in my life from me. I took the only person you wanted to save from you. I guess we're even now."

"No. Please don't do this. If anything happened to him because of something I did, I could never forgive myself."

"Perfect. That's what I wanted, you to suffer for the rest of your days like I am."

"Can I do anything to change your mind, please? I'll do anything to save Mike, he's in a terrible place. He had suffered his entire life; I just can't be the reason for his end. Please have some mercy on me, if not me, then on him."

He just looked in her eyes directly, enjoying her tears and said nothing for what seemed like forever but was few seconds. Then he said, "Okay then listen to me carefully you bitch and don't interrupt and remember all details. I won't repeat anything.

The sudden change surprised her, but kept listening. "Take this hotel key, it's for The Sheraton downtown room 2134. You are in this room coming Saturday morning sharp at 10," as he slides the room key in front of her.

Then, looking into her eyes, he said, "I don't care what you tell your husband, but you'd be gone for an entire day and possibly the next day. Now about what you're supposed to do when you're there. Well, make sure whoever is in that room, you fuck them and when I say fuck them, I mean give them the best fuck of their entire life."

He noticed a sudden fear in her face but kept ongoing, "if even one person leaves without fucking you, your brother is in prison. So, what you do and how you fuck everyone in that room is not my concern, but remember one thing: I will know if that doesn't happen."

Taking another sip of her coffee, he continued, "also do whatever they say, while you're in that room remember NO is not a word that you have in your dictionary. At any instance, anyone asks you to do something, and you say no, our deal is off and your brother, well you know."

With that, he got up and left without giving her chance to respond or even negotiate with him any further because that was the plan. He wanted to put an extremely hard character in front of her and staying there might have created some issues if she begs with her crying ass eyes.

She looked at the hotel key and realized what had just happened and what she'll have to do to save Mike. Could she do it? Anyone in the room means there will be multiple people in the room. Can she cheat on her husband? He was her childhood sweetheart.

She had never in her entire life slept with anyone but him. She loved him very much, but refusing to do it means letting her brother die intentionally. He had saved her throughout her life and it's her chance to return the favor. Specially since he was in this situation because of what she did.

This was a huge dilemma for her. She waited for 45 more minutes just thinking through and hoping she could decide, but whatever circumstance she thinks of ends up being a bad idea.

What if after she's done with this, and he still ends up in prison? Finally, she picked up the hotel key and put it in her purse. The idea was to keep it and think through the entire week she'll be able to come up with a better solution. She left back for her home.

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Before she could decide, it was already Friday, and she was driving back towards her home and do not know what she would do. She thought of worst-case scenario, if she went through with it and her husband finds out, a divorce but on the flip side dead brother.

At that moment, she thought she can live with a divorce and stay alone her entire life as a punishment for her transgressions, but she can't live being the reason for the death of her brother. She would make sure everyone in that room will end up fucking her no matter what she had to do it to achieve this task.

She made a stop at a gas station to refill and think how she'll do it, since she had no experience in this field.

While refilling the gas, she realized she needs to take the role of a slut from some porn movie to achieve the massive task. She needs to go shop for it now, since she had no dress that could suite the role.

She drove towards a shopping mall to buy the right dress. After about 2 hours of shopping around in the mall, she had bought a tube top dress with darkest shade of red with a glistening shine on it. The dress was so short that it barely covered her ass. Also bought a Victoria Secrets thong of same color as the dress along with 6 inches heels with straps, again same matching color.

She was extremely nervous about the dress and how could she leave the house wearing that dress, her husband will instantly start asking questions since that is way out of normal behavior for her.

Finally, she decided that she'll leave the house in normal clothes and once in the hotel will change clothes in the hotel's restroom and then go to that insidious room. She hid the slut attire in the trunk of her car to avoid questioning from her husband.

Now there was only one thing left for her to finish the slut persona. She went to the bathroom and prepared a nice bubble bath. Laying down and thinking about how she would approach this task next morning. This is her first time cheating on her husband and that too with potentially multiple people.

Past few days have been so emotionally exhausting for her she just fell sleep in the bathtub. When she woke up, she did not know how long she had slept, but remembered the last task. She took the shaving razor and cream and started shaving her entire body. At last, she reached the spot she had never shaved her vagina. She had always kept it trimmed but never shaved it.

Taking a deep breath, she started shaving and within a few minutes there were no hairs left in her entire body below the neck; she had even shaved her asshole. She got up and took a quick shower to get rid of all the remaining soap on her body.

Once out, she dried herself and applied moisturizer on her entire body and wore a robe. She was preparing for the dinner when her husband came down to the kitchen and asked, "hey honey, need help? What can I do"?