Teacher's Dilemma

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:

From this chapter onwards, some people might feel the story is diverting in multiple directions. But readers who have patience will find out eventually that everything is planned and will link to a single thread.

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

Chapter Notes:

This chapter continues from the party events of chapter 03 after Jessica passed out. If you have not read that chapter or don't remember it that well, please read it again. Here I have assumed readers remember all events of that party till she passed out.

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FEW YEARS EARLIER

Jessica shouted from her bedroom while getting ready for the party, "how come you never invited me to any of your work parties before? It's been years since we're together and you never invited to any of your parties."

"Most of the parties don't allow spouses, and some of them are not appropriate for spouses. So, I thought you'd not feel comfortable to join me in those parties," said Jason.

"I'll not feel comfortable. Are those work parties or orgies?"

Jason laughed and said, "You're getting naughty already. I'd recommend wait till we're back."

She walked out to the living room after she felt confident that the makeup was good for the party. Jason felt an instant turn on after looking at how sexy his wife looked in the dress he chose for her. He asked her to turn around once for him and when she did in a very sexy way; he didn't want to leave the house anymore, just bang his wife right now. Controlling himself, he said, "You look hot."

Jessica was wearing his favorite red backless bodycon halter neck dress that went just a few inches below her cunt. It was shortest dress she owned, and the backless part of the dress was till her ass crack. On her tits it was a deep V, exposing and elaborating her cleavage. She couldn't wear a bra under this dress and Jason begged her to not wear panties as well, which she finally agreed. She was also wearing a matching red four inches heels which were the highest she owned. She'd only wore this dress once on Jason's birthday when they went clubbing.

"I look ridiculously slutty in this dress. I don't think I should wear this around your work colleagues, especially when I'm meeting them for the first time."

"You look absolutely wonderful, hon. I'm considering skipping the party and just fuck you right here, right now in the living room. But then we're already running late."

"I'm trusting you on this one, Jason. Don't make me a laughingstock of the party, otherwise I won't go with you to any other party in the future."

"Are you fucking kidding me? What man in his right mind laugh at you in this dress? You'd be everyone's dream woman for the party, but they all got to suck it up because you'll leave with me at the end of everything."

"You sure about that?" teased Jessica.

"Oh, sassy, huh? Don't you dare cheat on me with your slutty ass look." he walked up to her and kissed close to her lips, not trying to ruin her lipstick.

"That's the problem. I don't want to be slutty for your work party. It's just too inappropriate."

"It's fine. There will be a lot of women at the party, even sluttier than you. Don't worry and just own it confidently. Let me order an Uber."

"Why Uber? We can drive there."

"No. We're both going to drink a lot and I don't want any of us driving back in that condition. I want you to be too horny the entire night. When we return, I want to fuck my slut crazy."

Jessica blushed at the last comment from her loving husband. She didn't realize that she was getting wetter by the minute as her husband talked nastier to her. But she didn't want him to get that idea and said, "I don't know what has gotten into you tonight? But for your own good, I hope I enjoy that party, otherwise you're going to be wanking off for days."

On their way to the party, Jason kept his hands around her neck and occasionally sliding it down to stimulate her nipples and other hand roaming around the inside of her inner thighs. He won't let her close her legs together. He would constantly tell her all the nasty things he would do to her once they would be back from the party. Jessica was on the edge of her sexual arousal by the time the Uber driver stopped outside a giant mansion.

Both got out of the cab and walked towards the main entrance of the mansion. Jessica felt dirty now because she knew her cunt was soaking wet already. She thought anyone could smell her arousal from a distance but was just a fear in head. It flabbergasted Jessica when they entered inside the mansion. The size and scale of the party was massive. It was like a giant gala dinner party.

When she looked around, every woman she saw wore expensive, exquisite, and elegant dresses. She felt extremely uncomfortable wearing such a short and slutty (nay whorish) dress. Jessica grabbed her husband's arm and hissed in his ears, "you fucking asshole, what did you do? I'm leaving right now and forget about getting anything from me for months, at least not until I recover from this embarrassment."

"Honest to god, I would never do this to you if I wasn't told that dress code for women was slutty themed. I am really sorry, but I would definitely kill Ray," said Jason, feeling embarrassed himself. Raymond Wilson was his roommate during his college days. DarkWeb hired both after they graduated in their MBA. Both never changed their jobs because they got substantial money, perks, and promotions. Only when executive positions were open, Jason got the promotion ahead of Ray. So, Ray now reports to Jason.

Jessica turned towards the door to leave the party. As she was leaving, a good-looking man in his 50s shouted, "There's our man, Jason. Where do you think you're going? Leaving the party so soon?"

"I'm afraid I'll have to leave early, Steve. My wife is feeling sick and will have to go back home so she can have some rest," lied Jason.

"Nonsense." Steve turned towards Jessica and said, "So you're Jessica, right? I've heard a great deal about you. You look, wow. You look amazing." He grabbed her hand and, in a smooth motion, gave her a friendly hug.

"Thank you," was all she could say nervously.

Steve Jacobs (54) was the CEO and founder of DarkWeb. He has a dashing personality for his age. At 6'2", he had an athletic physique because of his interests in sports and marathons. If anyone had to describe him in two words, it would be, "Charming Caucasian". He grabbed Jessica's hand and directed both inside the party hall.

"If I may have everyone's attention, please. Most people who work at DarkWeb would already know Jason. He's our rockstar. But I would like to introduce his lovely wife here, Jessica," he announced, as if introducing some celebrity. "I would hope all of you will shower her with your love, as you do with Jason. I'm so shocked that over so many years this is the first time we're meeting her."

He kept on praising her like she was the most beautiful woman he had ever seen in his life. But for Jessica, she was throwing daggers from her eyes towards Jason. Not only she was the only slut in the party, but now she was the center of attention as well. She was far beyond embarrassed now. She vowed to never come back to any of his corporate parties ever again.

Jason did not know how to defuse this situation. Steve would not shut up and he would not let go of her hand. It was like he was a kid and had received the most prized possession he ever wanted. He had always admired Steve and couldn't muster enough courage to rescue his own wife from this public embarrassment.

He then saw Steve's wife walking towards them with a glass of red wine in her hand. Nia Wilson (46) was a gorgeous black woman. She was one of the most famous criminal attorneys in the state. They both married 22 years ago and had two kids, a son, and a daughter.

Once Nia reached to them, she said, "come on Steve. Can't you see you're embarrassing the young woman here. Let her go," she took hold of Jessica and said to her, "I'm sorry. He didn't mean to embarrass you. He's just a sweetheart and usually gets really excited when he meets new people."

"It's alright," said Jessica meekly. What Jessica didn't realize was that she was even more aroused than when she arrived at the party. This perceived public humiliation in her head had brought immense wetness to her cunt.

"Wow, you look gorgeous. Now I know why Jason here doesn't look at any other woman. There's no one as beautiful as you are. I'm amazed. And this dress is so wonderful. It's meant for you. I wish I could pull off such a dress. I would wear it. I'm old now, so I don't even try it anymore."

Jessica blushed to an even deeper shade of red, if that was possible. But she said to Nia, "no what are you talking about? You're much fitter than I am."

"Oh, shut up. I'm not the one giving a raise to your husband, so there's no benefit in praising me unnecessarily," said Nia in a teasing tone.

"No, I'm telling the truth. You can ask Jason if you like."

Nia turned to Jason, waiting for a response. Jason was too angry at Ray for making a fool of his wife in such a massive party that he wasn't even paying attention to what both women were talking about. He looked at Jessica guessingly, hoping for a hint.

Nia instantly used this opportunity and said back to Jessica, "don't you dare feed him words. He's trying to be polite, but he can't lie as well." Jessica thought this party couldn't get more awkward. Why would Jason not take the cue and help her out in a situation like this?

Jason realized that he might have missed an important conversation, so he said, "I'm extremely sorry, ladies. I was lost in my own thoughts and couldn't listen to your conversation."

Nia laughed and said, "it's nothing. I was teasing your gorgeous wife. Why are you guys not drinking anything? Come on with me. Let's get that fixed right now."

Neither Nia nor Steve would listen to them about their lame excuses to leave the party. Soon after a few drinks, Jessica felt relaxed. They kept talking and drinks kept flowing. Ray also joined them later. By now, Jason didn't have enough sense left in him to confront him anymore. Both Jessica and Jason didn't realize that they were both drinking at the fastest rate at the entire table. Nia would not let their glass empty. And if they try to slow down, Steve will constantly remind them how slow they're drinking. An hour later, they were the most drunk couple at the party.

Even after the dinner, alcohol kept coming. Both were not in their full senses anymore. Then Ray recommended, "why don't you guys hit the dance floor. The DJ is playing some romantic songs." Steve agreed to the suggestion and forced both Jason and Jessica to join them.

With no more inhibitions left in them, they joined. For next few songs, both couples danced on the romantic songs played. Then Nia walked up to the couple and said assertively, "would you mind dancing with me, Jason? You've danced with your gorgeous wife forever."

Jason looked at his wife for any cue. Even in his intoxicated state, he didn't want to hurt their relationship. Nia had already conditioned Jessica with constant praises by her she couldn't refuse and gave a nod to her husband.

As she took his hand and teasingly said, "I can see who's the man of the house." Jason blushed but did not respond to the comment. His subconscious mind was telling him to not make any inappropriate comment to the boss' wife. Soon, they both started dancing.

Few minutes later, Steve walked up to Jessica and offered his hand for dance and said, "May I?" Since she was standing ideal on the side of the dance floor watching all other couples dancing, she couldn't make any excuse to refuse and joined him at the dance floor.

They both danced well for the first couple of songs. Once Jessica was comfortable dancing with Steve, he started making his advances. Occasionally brushing his hands on her tits with focus on the rock-hard nipples clearly protruding under the slutty dress. His chin resting on her left shoulder, and he was sexually breathing in her ear. She wanted to say something but couldn't.

First, she was highly intoxicated, so her sense of refusal was not working that well. Second, she was excessively horny by now. All she had in her mind was sex. In next few minutes, he got bolder. His hands were clearly and blatantly massaging her tits and occasionally pinching her nipples. She was so horny that she closed her eyes and completely forgot that she was not dancing with Jason, but with his boss.

Another few minutes later, his one hand constantly massaged her tit and played with her nipples and his other hand went downwards. He grabbed her ass and then brought them to the front. Rubbing them inside her thighs and drifting them upwards. When he noticed her opening her legs for better access, he realized he had her completely under his control. His hand reached for the soaking wet cunt. "Jackpot," he thought.

He rubbed her cunt for a few seconds and then, with a swift motion, inserted two fingers up her cunt. She gasped, but then eventually moaned softly. She did not care where she was all she cared was her orgasm. She was so close. Just a few more seconds and she would cum right on the dance floor with people surrounding her from all sides. Then she heard a soft erotic voice, "you like that?" She opened her eyes with the realization of what she was doing and where she was along with who she was with. She's openly cheating on her husband with him dancing next to her.

Before she could respond, he continued, "I know you love it. When I saw you, I knew you were the one. Ray had his doubts, but now it's all clear. You know, I own an exclusive and extremely secretive club where people would love you. You would need some changes, but they love to own whores like you. Oh, man, you're a masterpiece. Jason is wasting you, but don't worry, I know how to get your full potential out of you."

He had increased his fingering and was rubbing her clit as well. It divided her brain into two parts. One wanted to desperately cum right here, right now, and another wanted to run away from here as early as possible. As she was about to cum, she forced herself to control. If she came, it means whatever he was saying was true. She's a whore who belonged to his exclusive club and not to Jason. If she loves Jason, she had to show him that even in her intoxicated state, she won't surrender to him.

"Please stop. Let me go, please," she said, but her voice didn't have the confidence in it she hoped for.

"Are you sure?" he said while he kept on with his fingering.

"Yes, I am sure. Please don't do it. Stop, please."

He noticed her body shaking and shivering because of her intense control over her orgasm. "There's no need to rush, otherwise he wouldn't get anything out of it," he thought but said to her, "only on one condition. If I take my fingers out, you'll have to suck my fingers clean right here and right now."

Jessica tried to look through her peripheral and realized that Jason was busy dancing with Nia and was not focusing on them. "This is the time," she thought but said, "yes I promise, please take it out now."

Steve took his fingers out and instantly pushed them into her mouth forcefully. She sucked them clean as fast as she could. Then he gave a quick but passionate kiss on her lips and said, "we'll discuss it maybe later sometime."

Jessica took few deep breaths to calm herself down before going back to Jason. They both talked to Steve and Nia for a few more minutes. Jessica was not much interested in the conversation, but didn't want to give anything away. She thought it would break Jason's heart if he found out what his loving wife did with his boss. She would avoid both Steve and Nia once they're back at home. Jason doesn't need to know about this at all if she still is faithful to him.

Once back in Uber, Jason was horny as hell. He started with his kisses, which Jessica couldn't focus on initially as her thoughts kept going to what Steve said to her. But eventually she gave in to her arousal in the cab. They both made out in the back seat of the cab like some new teenage lovers. By the time they reached back home, both had nothing but sex in their minds. That night's sex was mind-blowing for both. After years, Jason fucked her three times in a single night.

Since that party night, Jason kept involving her in more family events with Steve, Nia, and Ray. They all got close to each other, but Jessica kept her distance as well. She would not drink over one or two glasses when around them. She tried to be a good friend to them while keeping herself safe from Steve.

After a few more months, Steve was more frustrated than ever. He couldn't tame Jessica. Nia walked up to him. "You give up now? Or still want to try some more?"

"Okay, I give up. You do your thing," said Steve in his frustration.

"Remember, it'll take time, but results are definite. My sister never fails with her plans. This is a big favor that she's doing for us. You would have to do what she wanted first though."

"You're the first wife, who is a lawyer and still wouldn't give a second thought to screw over her husband in favor of her sister. Only if I have control over my urges. Fuck. Okay, I'll do it. But remember, if afterwards I go down everyone goes down."

"Don't worry. You won't go down. The best lawyer is your wife and partner in crime," she said, winking at him.

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PRESENT DAY

Jessica sat at the Starbucks, contemplating how to watch the contents of this mysterious disk. She can't trust any of her personal or work devices. Tyrone might have compromised all of them. She waited there for another 45 minutes with no idea how she can watch it without her master's knowledge. Her next thought was to ask for help. It's possible that this mysterious angel might help her with this issue.

She grabbed that flip phone again and sent a text:

They compromised all my devices. I don't know how I can watch it without them finding it out. Can you please help me get a clean device temporarily?

She waited for the next few minutes with no response from her mysterious helper. Then she got a text back:

I will not help you with every straightforward thing. I can't physically help you. I can only guide you to help yourself. If you're not up to the task, then please leave the phone and forget about everything.

Jessica now felt like she was blowing away her only chance at redemption here by acting silly. Of course, she'll have to figure things out herself. She sent another text apologizing:

I'm sorry. I'll figure something out.

She again got the text back, repeating those same words as before:

Don't give up. I got your back.

Back again to the square one. How to watch the contents of this disk? Then she realized that city library has some shared computers. It's risky, but mostly not compromised by Tyrone. She drove out of Starbucks and on her way bought some cheap headphones. It's highly unlikely that anything inside this disk would be proper for a public place.