Teacher's Dilemma Ch. 07

Special thanks to "Ellie aka Worthless Whore" for volunteering with the editing of this chapter. She has done a magnificent job at fixing my most common errors. Hope you all will enjoy her work on it as well.

Author's Note: Please read this series sequentially to get a better understanding. This story is eventually going to take a dark path and will not follow any traditional non-con templates that most stories do. If you're expecting a traditional non-con story through and through, it will disappoint you at some point. If you want better character development and unexpected plot twists, you'll be in for a treat. If you choose to follow this series and still get offended, I gave you a fair warning. That being said, let's continue.

Special Notes: I have intentionally dropped clues at each chapter. People paying attention might guess what could happen next.

Chapter's Notes: Giving no spoilers, dark content starts in this chapter. If you're offended easily, please look for another story.

* * * * *

Several Years Ago

Devin was driving his car when he got a call. He picked it up and said, "Hey Jimmy, how's it going?"

"I'm always great, man. Ben called me yesterday and told me you're still struggling with those nightmares?"

He didn't like to talk about that topic with people, as he felt like it brought his weaker side out, especially in front of his friends. Ben was the only person who could fetch things out of Devin and now he regretted telling him about it. With a deep sigh, he replied, "I should have not told anything to that fucker. I knew you guys would use him to get things out of me, but I still fall for that trap every time."

"Man, there's nothing wrong with it, okay. Everyone from the team has nightmares, you're not alone in it, dude. It's normal, especially after the kind of shit they made us do up there."

"Not you though."

"I'm a unique case. You know you can't compare how you feel about things because I don't feel anything emotionally. Honestly, you are a lucky man. I have this hollowness within me. I want to feel something. Whether it's love, hate, shame, regret, or fear. It's not as easy for me as you think. If I could trade places with you, I'd do that in a heartbeat."

Devin knew that Jimmy was right. Somehow, his macho-man image in his brain couldn't function that well when he's vulnerable. He softly replied, "I know man, you're right."

"So, is it true that you're finally agreed to visit a therapist?"

"Yeah. Ben wouldn't give up and said the therapist he had at his home helped him a lot and I should try it."

"That's splendid news. Everyone is visiting psychiatrists in their own cities, and I've heard positive outcomes. I'm glad you also decided in favor of it. I'm sure it'll help you a lot. Now that we're officially not working in the army anymore, there's a lot of time. Who're you visiting?"

"Forgot the name, but Colonel Sanders vouched for this person and said I'll get the right help needed. Just wait a minute, let me find a parking spot," said Devin and parked his car.

"Okay buddy, you talk to that doctor. If the Colonel has recommended the doctor for sure it would be great. Once you're out, call me. I'd like to know what happened."

Devin disconnected the call and went inside the building. The receptionist told him to wait for a few minutes. He sat in the waiting area for five minutes when she said, "Sir you can go in now. Second room on the left."

He walked as per the directions and opened the door and heard a female voice, "Come on in. How're you doing today?"

"Not bad. I'm Devin."

"Yeah, I know from your file. I'm Rachael," and they shook hands. She continued, "Take a seat and relax. We have a lot to talk about."

c

Friday, four days after Jessica's encounter with Rachael

Mike walked through the grocery store stocking all the frozen food he stocked for his home. He only ate proper meals on Sundays when Jessica would visit him. Not paying attention and when his back touched someone else, he turned and involuntarily said, "I'm extremely sorry. I wasn't paying attention." After looking at the beautiful Asian woman, he had an instant infatuation with her. Mike always had a fantasy for Asian women.

She responded, "Oh no, you're alright. I was the one walking without looking forward. I'm sorry."

"It's fine. I guess we're both at fault here. I'm Mike," he tried to introduce himself, hoping for a longer conversation with this beautiful woman.

"Hi. I'm Anna."

There was an awkward silence for a few seconds, as Mike didn't know what to say after the introduction. He had not dated any girl in years and lacked the confidence to communicate with her. He thought, "Say something you idiot. You look like a creep now, say something. Don't blow this chance."

As his mind was racing through a lot of questions, she started the conversation again, "So do you live nearby?"

"Yes. Yes, I live... Um... I live..." he started stammering since his mind raced through the possibility of bringing her to his apartment. "The moment she sees my apartment, she'll run away. What should I do? I can't bring her to my place. It's a train wreck," he again had negative thoughts.

"I'm sorry I didn't want to breach your privacy. I should go now."

"No. No. It's fine. I live close by. Just a short walking distance from here," he instantly regretted saying that as he panicked when he heard she could leave.

"Oh, that's great. I rarely come to this part of the town, but it's a nice store," she lied. In an ideal situation, she'd buy nothing in this neighborhood. She continued, "We should have a coffee or something if you don't mind. I'm sorry if I'm pushing you to agree to something that you don't want."

"No. It's fine. In fact, I was thinking the same." In his excitement, he didn't think it to be weird that a strange woman asked him out with no knowledge about him. He didn't think that women would never ask guys out in grocery stores.

They both went to a small local coffee shop that was near the grocery store. Anna had the perfect practice to seduce men. She remembered what Rose told her earlier, "I don't know how you're going to do it, but I want you to fuck him in his own apartment. I won't accept failure." Mike and Anna chatted for over an hour in the coffee shop, and he felt much more confident now. He had been out of the game for too long and lacked confidence around women.

After a while Anna went for the kill shot and said in her well trained seductive soft voice, "It's been a while since we're just chatting here. Why don't we walk to your place and continue our conversation?"

This had the desired effect on Mike as he replied, "Yes, I was thinking the same." As they stood up, he realized he had been saying yes to everything. She had complete control over him. While walking towards his studio, he felt nervous because his house wasn't the ideal place to bring any girl, especially if you intended to impress her. He finally confessed before they reached the apartment.

He cleared his throat and nervously said, "I meant to tell you something. Um... I had a past and had been in prison for a few years. Currently, I'm on parole and my financial situation is not that great. My apartment..." before he could finish his sentence, Anna pulled him towards her and kissed him passionately on his lips. Few minutes later, she removed her mouth and said, "What do you think, I'm a gold digger?" He felt like he was blowing away his only chance by being stupid and to save the situation continued, "No, I was just..." Anna placed her index finger on his lips and said, "Shhhh... You're talking too much let's just go to your apartment first."

They both reached his messy apartment, and he removed all the dirty clothes from his bed and threw them on top of an empty chair. There was no other place to sit in his house than the bed. Anna felt like this was a place she would never go willingly. But today she didn't have a choice. She had to fuck him.

As Mike turned towards her, she instantly jumped on him and they kissed passionately. Things soon escalated fast, and both were soon naked. His cock was already rock hard. She knelt and licked his shaft like a popsicle. Mike gasped, as he hadn't had sex in a long time. His life hasn't been on track. She sucked his cock and with her skillful mouth took his entire seven inches long cock deep in her throat.

"Oh, my god. You're so... good... I'm going..." said Mike and couldn't speak anymore. He was already going to cum in her throat. Anna felt it, removed her mouth, and stood up. She didn't know if he could fuck her if he came in her throat and it would cause punishment for her.

"Not just yet. You haven't even fucked me. You want to fuck, right?" whispered Anna in the sexiest voice he had ever heard from a woman. Mike couldn't say anything. He just nodded. Anna hopped on top of him and in one thrust, took his cock all the way in, cowgirl style. As she rode him, she started making fake pleasure noises and dirty words like a true paid whore, "Oh, yes. Fuck me. Yes... just like that... oh you're so big... so good..."

Mike felt extremely turned on. It was like the best sexual dream becoming a reality for him. His lack of sex in a long time and all the events caused him to ejaculate his load prematurely. After depositing the entire load inside her, he felt terrible for not lasting longer. As his cock became flaccid, he said with regret, "I'm extremely sorry. I haven't had a girl in a long time. I'll do better next time."

She kissed him again and then whispered in his ear, "Oh darling, don't you worry. You were wonderful. I loved every second." She hopped off him and went to the bathroom to clean. Even Mike could sense that she was clearly lying. There's no way she could have enjoyed it. But he didn't want to probe any further. He knew the chances were that he wouldn't get to see her again after that performance.

When she returned, she had her clothes on. Mike was standing, still naked, with his flaccid cock. Anna walked up to him and gave him another kiss. As they broke the kiss, Mike saw the ring on her finger. "Why didn't I see it earlier? Oh, I was so fucking turned on with the idea of this girl that I didn't look for anything other than her face. She's so fucking hot," he thought. He couldn't control himself from asking, "You're married?"

Anna replied without hesitation, "Yes, darling. Is that an issue with you?"

"No. Not for me. But what about your husband?"

"Oh, he doesn't need to know." Anna continued by getting closer to him and again with her sexiest voice whispered in his ear, "I like to be a whore frequently to satisfy my cravings with a hunk like you." She grabbed his flaccid cock and continued to whisper, "I hope I was good enough for a repeat?"

Mike swallowed his saliva nervously. He hadn't been extremely good with women and had never been with a woman so confident and sexy. Completely under her control, he said, "Yes, of course. Whenever you want, just call me."

For the first time in her life, Anna was controlling the situation, and it felt fantastic. In the same voice she whispered, "Then give me your number. I'll definitely call you for, let's say, for some more exotic experience." They both exchanged numbers, and she left his apartment. While driving back, she felt weirdly great with her own seduction skills. "I'm great at this shit," she thought.

* * * * *

Thursday, three days after Jessica's encounter with Rachael

Rachael sat in her office while working at her computer. She heard a knock on the door and said, "Come in." She looked up and saw Tyrone walking in her office. His unannounced visit surprised her. He had never shown up to her office before, especially after his expulsion from the university.

"Tyrone, what a surprise. Take a seat. How may I help you today?" said Rachael.

Tyrone sat in front of her and said, "Well I found out that you've been plotting a lot of things recently. I thought we both should discuss it face to face."

"I don't think I follow you."

He said nothing, just pulled the mini-recorder out of his pocket and started playing the recording. He had removed the irrelevant conversations from it and just kept the juicy pieces only. The facial expressions of Rachael told him everything. She had utter shock on her face. First time in all her planning, she let her guard down around Jessica and it turned out to be a disaster.

When the recording ended, Tyrone continued, "Do you have anything to add?"

She sighed after realizing there's no point in lying from here. Jessica had outplayed her this time. She replied, "If it's any consolation, I didn't want to do it. Devin was desperate for your help, and you wouldn't listen. He asked for help, and I had to help him."

"And that's supposed to make me feel better?"

"No. It's the truth. You asked for it and I told you. Now you can handle it or not, it's up to you. I mean, don't get any wrong ideas, you're nothing without your brother. If you want to fight him, you can. But I wouldn't bet on you."

Her audacity to still be cocky around him snapped something inside him and instantly jumped on her desk and grabbed the collar of her blouse and pulled her face near his. His anger came through his words, "You're a fucking bitch. And I'm going to make you, my bitch. You think when I tell Devin that the only way, I will work with him from now on is if I take you down. What would he say?"

His anger didn't faze her a bit. She took a deep breath and said, "First leave my blouse and take your seat," while continuing to stare directly into his eyes. He released her collar and took his seat back. "Why is she not scared?" thought Tyrone.

There was silence for the next few seconds, and then she stood up from her seat. While walking towards him, she said, "You want to run to your brother and snitch about what I did to you, go ahead. Go run. Shoo." Tyrone couldn't say a word at her condescending and overconfident tone. "Why is she not scared of Devin?" he thought.

When she didn't get any response from him, she continued, "You want the actual truth? Can you handle the truth? You can't handle it? You've been in a shell for far too long because of your brother. If you knew who you were yelling at, you'd be shitting in your diaper by now. You think I fear your brother? Go run to him. Beg for help. Let me know what happens next."

She stumped Tyrone. When he said nothing, she continued, "Now I'll Tell you the truth. I made the decision that you needed to be a full-time part of the group and I made the plan.

Devin knew everything, and I told him what the plan was. He agreed it was the best way forward. Now why would I do that? The answer to that question lies within another question. Let me ask you that question. WHO DO YOU THINK RUNS SHIT IN THE GANG?"

Tyrone swallowed, realizing what she implied with the last question. She continued again, "Let me answer that question for you. I. AM. THE. REAL. BOSS. OF. THIS. GANG." She stopped for a few seconds to let this information sink in then said, "When Devin returned from the army he was in a seriously dark place. I took him out of that place. It was then we both laid the plan for this gang. The plan was for him to be the face and pretend boss while I'll run everything from the backend. I'm the brains and he's the muscle. I give the orders and he will blindly follow them."

By now, he had lost every hope of any revenge on her. Rachael continued, "I planned everything. How to take down the Latinos? How to establish our ground and fear among the people? It was an unbelievably detailed and futuristic plan. I needed it to expand nationwide. For that, I needed you. Your excellent knowledge and zeal towards the technology was all I needed. But no matter how smart you are, it's not possible to create grand scale technology infrastructure overnight. And I didn't have all the time for it. Here comes Steve into the plan."

She was still in her anger mode and continued, "I had to make a deal with Steve no matter what he needed. I couldn't offer him money. He already has more than he needs. The only thing he couldn't get was Jessica. I used my sister to increase his urge towards Jessica so that she became an uncontrollable urge for him. To the point where he couldn't resist not having her any longer. Then he agreed to the deal with me. The entire baseline tech infrastructure you're using right now belongs to DarkWeb. He approved an illegal tech research farm just for us."

"And he did all this just to get Jessica for his club. Don't worry, he'll make every penny back from her and more. He has his own kinks and gets a lot of favors from many people who are secret members of his club and are extremely influential worldwide. But then you wanted to ruin everything. You wouldn't let Steve have her for the club. Your need to be her primary owner and inability to leave control of her caused so many problems for me. If you were anybody else and not Devin's brother, you would have disappeared by now, but I had to work through the plan. I kept Steve at bay for as long as I could, but then, after investing so much money, he wouldn't listen to me anymore. I had to invite him to that party so that I could buy some time."

She took a few deep breaths and continued, now a lot calmer, "Now you have to realize Tyrone, she needs to join the club, there's no choice in the matter. I can't save her, and neither can you. It's for the greater good. You can't save her anymore. And anyway, you've done so much to her I don't understand why you need to be her angel suddenly?"

Tyrone responded after a long while, "She's my responsibility. I can do whatever I want for her. But I can't let anyone else own her."

"So, it's an ego thing? You don't have enough power over Steve. I'm going to give her to him, and the club, and you won't get me in my way this time. You and your brother both are emotional wrecks. He slept with her and promised a lot of shit to her. I had to plan accordingly so that he doesn't get any closer to her, otherwise he would have ruined everything."

Something snapped within Tyrone now, and he stood up and left for the door. As he held the doorknob, he turned and said, "I don't have enough power over Steve because you and Devin took his side. Let's have it then. I'm done with both you and Devin. I will not give my Jessica to him. You, my brother, and his friends on one side and I alone on the other. Let's see who wins this war. It took you years to reach here. I promise you right here, I'll crumble everything in the next two months. Let the battle begin."

He opened the door and was about to leave when she said, "You're being stupid here Tyrone. You know there's no way you can beat us and if you try, we won't forgive you this time." He said nothing and left her office.

In recent days, her plan has been falling apart. The sudden anger creeped up again, and she threw the coffee mug at the wall, and it broke in multiple fragments as she yelled, "You are a fucking whore. I let my guard down one time and you fucked up everything. Once I handle this fucking idiot, I'll show you what I'm going to do to you."

As she cleaned the mess around her office, there was another knock on the door. She said, "Wait a minute." Once she sat in her chair, she said, "Come in." To another surprise, in came the last person she could have thought of, Rose. "Fuck me, what does she want now," she thought.

Rose sat in the chair opposite to her and said, "I'll get straight to the point. This is the last thing I want to do, but I can't handle it anymore. When you did what you did, I wanted to take my revenge on you. But now I have realized that there's no way I can do anything to you. I give up. I don't know what I ever did to you, but I need to get back to being Jessica's mistress. I'm here to make my peace with you and I'm asking you what I can do to get things to be normal between us?"