Teacher's Dilemma Ch. 07

Anna sat on the bed next to still blind and deaf Mike. Rose left the room and called Rachael, "Yes I did it. Once I'm assigned a task, I always pull through. Now do we have a deal that I'm back at her house?"

"What deal? I never said we would have such a deal after this task. Yes, now I can say that if you're good enough, I might allow you to be her mistress occasionally. But if you hope that you'd be back on your old terms, you must be out of your mind."

Rose knew that Rachael played her again. Her anger creeped up, but she knew better. There's no point in yelling at her. She holds all the cards. "My time will come, bitch," she thought, but remained quiet.

"And clean the brother but keep him at your slave's house for another thirty minutes."

With a deep sigh, she said, "Okay, I will." And then she disconnected the call.

Rose took the camera from Anna and told her to tell him to clean himself and keep him here for another thirty minutes. Anna commanded him to remove the earphones and contacts now. She was enjoying this new power over some other person. She didn't mean to cause him any harm, unlike Rose and Rachael. It felt a little different and better being blackmailed and forced to submit than commanding someone of their free will.

They both chatted a few more minutes after he came back from the shower. He expressed his immense gratitude for giving him the best sex of his life. Anna said nothing since it would break his heart if he knew the woman, he was fucking for so long was his sister. And then there was a doorbell. She went to check and opened the door. There was a man in casual dress and two cops behind him standing at her doorstep. It frightened her. No idea what cops would be doing at her house.

The guy in the casual dress spoke. "We believe you might have Michael Clark at your home. I'm his parole officer and these gentlemen are from the police department. Is it correct?"

"Yes. But what happened?"

"We have an arrest warrant for him. Ma'am, please step aside so these gentlemen could do their duties?"

Anna moved out of their way. Soon she saw Mike cuffed and brought out by both the cops. He asked the parole officer, "But what did I do?" He replied, "You know doing drugs while on parole is illegal. Your urine test came positive for drugs. And back you go to the prison." He seemed more delighted by Mike's arrest. Moments later, Mike was gone, and it scared Anna. Things had changed drastically that they lifted their support from Mike.

***************************

London

Jason unlocked the door and walked inside the house. It's already late at night and he felt completely tired from all the work. After the last call from Steve, he had dedicated himself completely to the work. He tried his best to avoid Sam outside of work. He noticed the lights in the house were on. He swore he switched the lights off before leaving. When he reached the living room, he saw both Ray and Sam sitting comfortably on the couch.

"Hey Ray, what a pleasant surprise. What are you doing here, buddy? I have to say I missed you folks a lot, man."

They both hugged each other. Then Ray said, "Steve told me you're missing your wife. So, I said I can't bring her here, but I can show up to surprise you for the weekend. I reached here to find out you're working on a Saturday as well."

"What were you guys watching?" asked Jason.

"Oh, nothing, it's a very great documentary that I found at Sam's place and thought to watch it here while we were both waiting for you to show up," replied Ray.

Jason sat on the couch to watch the documentary and as it played, he stood up instantly and shouted at them, "What the fuck is this, Ray?"

"It's a documentary about your escapades in London, Jason. Come on, don't tell me it's not you. I can clearly see your face enjoying the hot pussy of your coworker. I was just thinking this is a documentary that Jess would definitely love. I'll show it to her when I return," said Ray in his cocky tone.

"Why would you do such a thing, Ray? We're friends. I've always looked after you buddy."

This time Ray stood up and yelled at him, "Shut the fuck up you motherfucker. You looked after me? Motherfucker. I was always part of your group so that you could show everyone how dashing, smart, and intelligent you were. You never missed a single opportunity to condescendingly humiliate me among the girls at university. You had a gorgeous girlfriend, but you still flirted with every girl I liked. You took everything that I wanted from me, even the promotion."

"This is about the promotion? I swear, I'll step down. You can take the position. I'll gladly work under you Ray."

"I'll fucking kill you, motherfucker, if you show me your pity ever again. I don't need your leftovers." Ray was furious now. Taking a few deep breaths, he tried to calm himself. He then stepped back and sat on the couch again. In a calmer tone he said, "So tell me, should I show this to Jess?"

"No, please don't. It'll break her heart. What do you want?"

"What can you do?"

"I'll do anything you want, just keep that away from Jess."

"Okay then undress. Remove everything."

"What?"

"I will not repeat, you dumb son of a bitch. UNDRESS NOW."

The sudden aggression from his best friend shook him out of his trance. He never even thought of such a situation in his worst nightmares. He thought of going ahead with it to save his relationship with Jess. Soon he stood completely naked and ashamed in front of them.

"Come forward and kneel in front of me," ordered Ray.

Jason followed the command and knelt in front of his friend, with eyes on his boots. Ray continued, "Here's how everything's going to go. I don't have time to train a fuckhead like you, so I'll head back tomorrow morning. But Sam here is generous enough to volunteer. So, from now on She's your mistress. You will refer to her at all times as mistress. In the morning, she'll give you a set of rules that you must always abide by. Failure to do so will cause severe punishments. DO YOU UNDERSTAND."

He nodded. Ray slapped him hard across his face and said, "When I ask a question, speak up and you'll refer to me as master and yourself as slave. Now speak."

"Yes, the slave understands," a whisper came out of his mouth.

Another slap to his cheek and Ray said, "When I say speak it means loud and clear. I didn't hear that from you. Speak up."

"Yes, the slave understands, master," spoke Jason much louder.

"Okay, sweetheart, continue with the plan. I'll just sit back and relax. I want to see how our slave responds to it," said Ray to Sam.

Sam walked up to a leather bag and grabbed a few things from it. She stood in front of him and said, "Okay fuckhead, open that dumpster of a mouth, nice and wide." Jason opened his mouth, and she inserted an enormous plastic cock in his mouth. Base of the cock had a leather strap on it. Jason struggled a lot because of his gag reflex. He had taken nothing so deep in his mouth before.

"Loosen the throat muscles a bit, you dumb fucking idiot," commanded Sam. It took her over ten minutes to jam the entire thing deep into his throat. Once the cock was all the way in, she attached the leather strap behind his back.

"Now turn around and on all fours, now." Ray commanded him in a stern voice.

Jason had tears in his eyes because of the gag reflex of deep throating for the first time. He followed the instructions instantly and was on all fours on the floor. Sam walked back towards the bag as she had forgotten something. When she returned, she had attached a strap-on with an eight inches long and two-and-a-half-inch wide dildo on it. She poured a generous amount of lube on her fingers and then on his asshole.

As he felt the cold liquid, he understood what was coming. He turned, moaned, and shook his head to signal his denial. His eyes were begging Sam to not do it.

"Shut the fuck up, bitch. Yes, you're my bitch from now on. If I do anything for you, you'll take it. Never shake your head around me or else punishments won't be nice," said Sam in her dominant tone. Now he surrendered to his fate and turned his head forward. He didn't want to see the assault anymore. "Stay calm and this will be over soon," he thought.

Sam inserted her finger in his virgin asshole. Instantly, they heard a loud moan from him through the gag. For the next few minutes, she finger-fucked his asshole and continued to add another finger. By the time she had her three fingers completely inside him, he didn't feel the pain anymore and his moans had clear arousal in it.

"Check it out, fucker's pathetic tiny cock is rock hard. This fucking loser is enjoying getting fucked in the ass," claimed Ray out loud.

When Jason realized it was true, he felt disgusted from within. "How the fuck am I enjoying this assault?" he thought.

Sam applied a generous amount of lube to the dildo and prepared it for his worst nightmare. As she inserted the head of the dildo, screams muffled by the cock in his throat got much louder. Jason was in immense pain. Sam did her best to slow down and let him adapt to the size and girth. It took another ten minutes before she had the entire cock buried deep in his asshole. She waited for another couple of minutes as she heard his screams getting softer. Then began the slow rhythm.

In and out. Several minutes later, Jason felt the pre-cum leaking out of his cock. "Why the fuck am I enjoying this shit? I shouldn't enjoy it. What is going on?" Anal sex for men is a taboo subject unless you're homosexual.

As she got into a better rhythm, Sam increased the speed. Now she was fucking him hard. His screams now replaced with aroused moans. It was beyond his understanding, but he enjoyed the experience. Several minutes of intense fucking and he felt his orgasm nearing to its release. Before he could understand his own feelings, his moans intensified, and he came hard while he felt shivers down his spine. He didn't want to acknowledge it, but it was an amazing experience for him.

He considers anal sex for straight men a taboo subject, hence he never thought he could enjoy it. A few minutes later when Sam had cleared everything away, Jason was again knelt in front of Ray. He continued, "You enjoyed it, didn't you, fucking dumbhead?"

Jason, still having the giant cock deep in his throat, nodded with extreme shame on his face. He couldn't accept that he enjoyed that experience. Ray continued, "I'm going to leave here tomorrow morning. You'll sleep right here on the floor. Sam will give you an extensive list of rules tomorrow. Remember it and don't break any rules."

Jason nodded his head, affirming that he understood everything. Jason continued, "Okay since you know what's next, good night dumb fuck."

Both Ray and Sam left for the bedroom while Jason tried sleeping on the floor. Entire night he could hear the loud moans from the bedroom. "You are a fucking asshole, Ray. You made her fuck me up the ass and now you're fucking her in my bed. I'll figure out a way to get back at you. I swear, I will." He kept thinking about how to get his revenge on Ray and soon dozed off to sleep.

***************************

Jessica parked her car in her garage and walked out. Her waiting routine was the same as before. She removed all her clothes, and her belongings went inside the metal box. The door opened in a few seconds. She felt glad that she didn't have to stay outside for much longer. She walked into her living room and her world collapsed as she saw Rachael sitting in the middle of her couch and both Jamie and Rick sitting on other sofa chairs. It didn't work. Everything she had done was in vain. Tyrone might have had a deal with her, but now she's out here hanging alone.

"Come here, my silly whore slave. Kneel before your mistress. Come on, faster than that," said Rachael when she saw Jessica walking extremely slowly towards her. Finally, she reached in front of her and instantly knelt like a docile pet.

"You really did try a stupid thing. And I must tell you that for every action there is an equal and opposite reaction and in this case it's a reaction you won't like. Sometimes innocent people get the blunt of those reactions. What were you thinking, whore?" asked Rachael in a very condescending tone.

Jessica did not know what to say and how to beg for forgiveness. She clearly overestimated her move. The back of her head was yelling at her to believe a stranger that there's an easier way to resolve the issue. "That unknown text message ruined my life even further. I do not know what she's going to do to me," thought Jessica. But dejected, she bowed her head and said meekly, "Your whore apologizes to her mistress. The whore made a stupid mistake and regrets it. She thought if she could help her master, she'd get on good terms with him, and he would make her life a little easier. Clearly, it was a massive mistake on the whore's side. Whore's really, really sorry mistress. Please forgive her." Jessica felt the immense fear of the unknown punishment that Rachael might give her.

"Your one stupid mistake has caused so much chaos around the whore. There's no way I can just forgive you for what you tried to do. I have to show you what happens when the dumb whore attempts to use her own head," said Rachael in a stern but calm tone.

She signaled Jamie to follow through with their plan, which she'd already explained to both brothers. Jamie walked up to her and grabbing her arm he said, "Stand up whore. Let's see what you have to say once you're in your right position." Next thing she knew, he had her on the floor, lying on her back. He attached soft leather cuffs to her ankles and wrists. Then came the spreader bar. He had her legs bent towards her belly and spread extremely wide and attached the spreader bar to keep them bound in place. Her legs were painfully wide.

Rick joined in to help his brother. They both helped her turn to face the floor. Then she felt a painful tug on her hair and Rick attached a big black leather collar to her neck. As usual, the collar was excessively tight, causing difficulty in breathing properly. Jamie helped her sit on the floor, which was uncomfortable considering the weird bondage position she had. Rick tightly bounds multiple layers of ropes around her tits. The ropes went above and underneath her tits, causing them to swell and started to redden. The ropes caused her extreme pain and discomfort. Then he attached a giant stainless-steel hook through the ropes on her back.

Similarly, they bound a bunch of ropes around her lower abdomen, causing even more discomfort. Another hook went on the ropes attached to her lower back. They both then lifted her in the air, facing the floor while Rachael attached both hooks, which on the other end had closable rings, to the chains attached to the ceiling. This time, Rachael pulled her hair up and attached another chain to the back of her collar. They forced her to face her tormentors while suspending several feet above the floor.

Rachael then went on to open the blinds and the sliding doors of her house to allow anyone looking through their backyard to watch her torment. "See now we're good. You can scream as much as you like now. Fun times," said Rachael. Jamie attached different types of clips to her nipple, clit, and pussy lips piercings.

She pulled out a small remote from her pocket and pressed a button, which sent an extremely painful electric charge through all her piercings to her most sensitive body parts. Jessica bit her lower lip harder than she intended to suppress her screams. After a few seconds, she stopped it and said, "These are fun ones. They don't send the arousing sensations you're so accustomed to, but they send painful electricity."

Rick pulled a chair for Rachael like a loyal servant, and she sat right in front of Jessica handing there. "So, where should we begin? Oh yes, the dumb whore thought she outsmarted me by recording our conversation. If I must accept the truth, it hurts me to find that I didn't see it coming, but again, in the back of my mind, I didn't give a shit. Tyrone was important for the mission to set up things and build a team that can work collectively to reach an end goal. Now that's done. So, I can find people to manage and handle the operation well enough. In fact, Ray had volunteered to take Ty's place."

She looked in Jessica's eyes to assert her dominance on her and continued, "I know he's not as intelligent and technical as Ty, but there's a bunch of intelligent folks already in the team. The hard work is already done. So now Ray can manage the team to continue our mission further. Plus, he has extra incentive to leave his current job. He can't stand to work under Jason anymore."

To Jessica's surprise, Rachael pressed the button again, but with her hands hidden behind the chair. The sudden, unexpected, and painful electric charge brought a loud scream from her mouth. She couldn't process it by biting her lips to suppress the scream. When everything stopped, Jessica instantly looked out as if people had gathered around her backyard.

"If you think with Ty out of picture, you'd have a better life I'd say you're even more of a fucking stupid whore than I thought. That stupid son of a bitch wouldn't let you go. I had to handle his tantrums just because he was Devin's brother. Now that he's out of sight, the coast is clear. I can do whatever I want to you. No one's going to stop me. That's why..." she pressed the button again in between her sentences but Jessica had prepped herself for sudden pain, so she suppressed her scream successfully this time.

The pain stopped, and she felt something curved, not too thick, enter inside her cunt. It was a g-spot vibrator. Ergonomically manufactured to supply the highest level of stimulation directly on the g-spot. A massive butt-plug inserted deep in her asshole followed this. Then intense vibrations began in both her holes. This time, Jessica had to suppress her powerful urge to moan loudly in pleasure.

"This is a punishment whore, and you remember the rules around punishments. So, follow the rules." Jessica struggled hard to control her hard-hitting orgasm. Her body shivered and shook from this intense control. Then she felt a hard strike on her ass from a soft leather whip. She couldn't see who was punishing her ass cheeks, but it wasn't the only strike. She got fifteen hard strikes on her ass before everything stopped. Both pleasure and pain, and before she could recover, Rachael pressed the button again. They repeated this extreme cycle of pain and pleasure several times. Jessica's mind struggled to control everything now.

She had tears in her eyes; she didn't know how to suppress her screams anymore. It was beyond insanity now. One moment she's moaning, desperate to cum, and another moment struggling to not scream out loud.

During this rest period, Rachael continued, "So, now things have to change again. As much as I want to become your primary owner, I don't have time for a worthless cunt. I have a business to run, lectures to teach and patients to treat. You are such a dumb and worthless whore that you couldn't survive on your own. So, these two lovely gentlemen have given such generosity upon you and offered to train your worthless holes properly, as they should be."

"They'll both be your primary owners all the time. And if you fuck up again or try some stupid heroic shit, I'll show you I can make your life even more miserable than it already is going to get!. Believe me, things can get even worse from here. Oh yeah, I forgot to mention, you'll soon be joining the club. Steve is working overtime to schedule all your wealthy and powerful clients at the club. Those guys are super busy, so getting hold of everyone together in one place is not a simple task. Once he has the time scheduled, you'll do your debut. Earlier, in your smartness, you discarded your only shield. Now no one can stop your entry to the club."