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.

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

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.

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

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.

She parked her car and went inside and searched for the most isolated computer. There was one in the room’s corner which faced to the back wall of the library. “This is the safest system. If anyone had to watch, they would have to walk behind her, which is highly unlikely,” she thought.

Once the system booted up and she had inserted the disk inside. She was extremely nervous when she saw there was a video file in it. She secured the headphones and looked around to see if the coast was clear. She prayed to God that the contents were not too horrific. With some leap of courage, she opened the file to watch the video. She watched herself passed out in that ridiculous whore dress under a black woman’s arms in her own living room. She thought, “What was her name? I think it was Taylor.”

The video was clearly from the hidden spy cams installed in her house by Tyrone. She now knows that this is the continuation of the day when she passed out in her own living room after that party and couldn’t remember what happened afterwards. Jessica was about to find out. Then in the video, she heard the doorbell rang.

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

Rose went to open the door. In walked Rachael. Completely shocked, Jessica paused the video and looked at the screen in disbelief. “She played me all this time. Why would she do such a thing to me? What did I ever do to her? I’ve always been nice to her. Why? Why Rachael? Why did you do it?” Jessica kept whispering her questions at the monitor as if Rachael were in front of her.

She had tears flowing from her eyes. Mustering some more courage, she played the video further.

“Everything going as per plan?” asked Rachael to Rose while walking into the living room.

“Even better,” replied Rose enthusiastically.

Once inside, she saw Jessica passed out and casually placed on the couch by Taylor. She smiled and happily asked, “what happened here to our sweetheart whore?”

“I made her cum so hard that she passed out,” replied Taylor, proud of her achievement.

Jessica woke up a few minutes later on the couch to find her friend Rachael sitting next to her with a glass of water in her hand. Confused, she rubbed her eyes, not believing what she saw. Finally realizing that her friend sat next to her, along with all her tormentors, she instantly hid her tits and cunt with both her hands. Somehow, Rachael, seeing what a whore she had become, was more embarrassing for her.

“I came here to save you, Jess. You don’t worry, I’ll handle everything from here. Just take this pill and it’ll help you feel better. Till then, let me talk to these scumbags for doing such heinous things to you,” said Rachael, giving her a pill and the glass of water.

Jessica saw her standing up from the couch and, confused, she asked her, “but Rachael, I’m fine. What is this pill for?”

“Don’t worry, just take it. You must be traumatized by what these monsters had done to you. This will help your brain recover from the trauma,” lied Rachael. She knew there’s no way for her to know there’s no magical pill to recover from trauma. Jessica thought the reason made little sense, but there was little reason to doubt her intentions. “Why would she lie to me,” thought Jessica as she took the unknown pill and drank the full glass of water. She still felt thirsty.

Anna returned to her with that familiar a gallon of water bottle. She gave it to her and nodded to her as if telling her she needs to drink it all. She saw Rachael talking to everyone, but she couldn’t hear anything from where she sat. She drank the entire gallon of water. She no longer felt thirsty, but felt her stomach full of water. Jessica felt proud that she could easily finish that enormous bottle of water when she saw Anna returning with another bottle.

She gave her the second gallon of water. Jessica looked pleadingly at her for some help. Her stomach was already too full she won’t be able to handle this much water. Anna shook her head signaling to her it’s not a choice. Reluctantly, Jessica started drinking from that bottle.

Rachael returned and said, “I’m handling the situation. I think I will resolve things soon. Oh, since you’re already drinking a lot of water, I’d say take another of this pill. You take it and relax. Everything will be fine.”

Jessica took another of that pill and saw Rachael talking to the group again. It took her several more minutes to finish that bottle as well. What she didn’t knew was that the pill she took was used to induce short-term medical amnesia. Rachael had access to this prescription drug since she’s a licensed clinical psychiatrist. She will not remember what happens from now onwards. They waited for the drug to show its effects. The benefits of this drug, it doesn’t make you delirious or sleepy.

Rose sat next to her, gently placed one hand around her back and started playing with her nipple while other hand playing with her other nipple. Within next few minutes, it aroused Jessica again when she felt Rose’s skillful mouth on her nipples. Jessica closed her eyes and laid back on the couch. Next, she felt another mouth on the other nipple, followed by someone spreading her legs and another on her cunt.

Jessica completely forgot where she was and enjoyed the feeling. It was so good. She needed more. Everyone could clearly see that she had forgotten about the rules and would not hold back her orgasm. With her eyes closed, she moaned and gasped loudly with incoherent words as she felt those wonderful fingers inside her most sensitive parts of her soaking wet cunt, “Oh… Oh… Ah… Fuck… So… Good… Yes… Please… Don’t… Stop… Please… Oh… Yes… Right… There… Harder… Oh… My… Fuck… I’m… Going… To… Yes…”

Right on when she was going to cum, she heard the voice of her master whispering in her ear from behind the couch, “if you wish to volunteer to fuck every man in your neighborhood, you can cum. If you want to keep the secret, don’t break any rules for the rest of the night. You’ve already broken one. Don’t doubt me, I’ll make you knock on each door naked and offer your cunt till everyone knows what a dirty whore you are.”

Scared, Jessica opened her eyes instantly and turned towards her master, begging for mercy from her eyes. There was a desperate need to cum in her eyes. But her master looked into those begging, deep blue eyes with a big smirk and said, “what’s it going to be?”

“Your whore will not cum, master. She’ll wait for her master’s permission like an honest whore should.” Jessica had tears in her eyes and her entire body felt the tremors of her desperate resolve to hold an impossible orgasm. She turned her gaze away from her master to find that Rose was sucking her left nipple and occasionally biting on it, creating an amazing combination of pain and pleasure. She looked down to find Anna using her skillful mouth and fingers in her cunt. “She’s so amazing. She’s so good. Wow, fuck, please stop or I’ll have to fuck my entire neighborhood. Please,” she thought in her head.

To deviate from this unbelievably amazing feeling, she turned right when she felt a bite on her right nipple. Jessica couldn’t hold her tears anymore after finding that the third mouth sucking and biting her right nipple was Rachael’s. After a few more minutes, when Jessica thought she couldn’t control any longer, she heard her master’s void. “Okay, that’s enough. I think she’s warmed up for the night.”

To her surprise, all three mouths left her three most sensitive body parts. But Rachael stood and sat on her lap, and gave her a deep and passionate kiss. Before Jessica could realize what was happening, both their tongues exploring each other’s mouth. This was one of the best kisses she has ever received from anyone, including her husband. Rachael was bi-sexual and an amazing kisser. Everyone who had the pleasure of being sexually intimate with her knew this about her. One of her exes would enjoy her kisses more than the actual sex with her.

Lost in the kiss, Jessica again forgot where she was and who she was kissing. She only wanted to enjoy the incredible feeling of this kiss. Without her realization, Jessica’s hands went on the back of Rachael’s head as she enjoyed the kiss. Few minutes later when Rachael removed her lips, Jessica felt disappointment.

“You were absolutely right, Tyrone. She’s a born whore. I doubted you, but this one just need a little warmup and she can fuck a train without questions,” said Rachael, without breaking the eye contact with Jessica, “aren’t you a dirty whore? I’ll make sure you’ll get what you deserve for the rest of your life. Now tell me what you deserve?”

“Why? Why’re you doing this to me? What have I ever done to you?”

Rachael gave a hard smack on each of her tits, right on her nipples, and said, “when I ask a question, just answer the question like a true whore should. A question can ‘t answer another question, can it? Now answer your mistress.”

“A whore like this deserves everything that her master and mistress decide. This whore shouldn’t hope for anything more than her generous masters and mistresses grant to her.” Jessica felt an urgent sense to disappear permanently from the face of this planet. Rachael didn’t allow her to break the eye contact during her humiliating revelation.

“That is correct,” she said and gave a quick, hard pinch on both her nipples together. Jessica screamed loudly but said nothing. Rachael stood up and walked to join others.

“You’ll not be eligible to cum until you have orally satisfied every woman in this party. Once each woman gives a nod of satisfaction from your performance, will I consider your request for an orgasm. No matter what happens, if you break this rule, you will fuck your entire neighborhood. And for the rest of the party, you’re free to talk as much as you want, but every word leaving your mouth needs to be nasty.”

Nervously, she looked at the other end of the living room. Taylor had already removed all her clothes and sat on a comfortable recliner sofa chair. She commanded Jessica, “come on whore, come here and pay your dues. I already gave you orgasms that you didn’t deserve. Now it’s your turn to return the favor.”

Jessica walked up to her and kneeled in front of her wide-open legs. As she was approaching her mistress’ cunt, she heard from her master, “I have heard nothing from you yet, whore. It’s a privilege for any slave whore to provide pleasure to her owners. To earn this privilege, a whore must beg for it. Convince your mistress that you need to do it. It’s the only purpose of your life.”

She cringed from within and thought, “it’s not enough for them to degrade my body they have to degrade my soul as well.” But she knew she had no choice so continued by saying, “please mistress, may your whore slave have the privilege to eat her mistress’ lovely pussy until her mistress has her orgasm? Please, mistress. Your whore will do anything her mistress asks her to do if she gets this privilege. Your whore slave begs her mistress. Please.”

“Yes, you may. But remember, you better do it like your life is inside this pussy. Suck your life out,” said Taylor.

Jessica had no experience with supplying oral satisfaction to women, but she needed to learn on the go. She gave a good long lick to Taylor’s pussy. Then she opened her pussy lips and started licking inside. After a couple of minutes, when she did not give any sort of stimulation to Taylor, she yelled, “what the fuck are you doing? Are you trying to give pleasure or are you trying to frustrate me? This is a worthless fucking whore. First time I met a whore who can’t even eat a pussy.”

Jessica was so much ashamed of herself now that she started crying while continuing to lick Taylor’s pussy as best as she could. Taylor grabbed an enormous bunch of blond hair and pulled her head up and looking directly into her eyes she said, “use your tongue you fucking dumb whore. Find the clit, lick it, suck it. Use your fingers. Do something other than irritating me, you fuckhead.”

Scared but determined to improve, Jessica went down for the second time. This time, she explored Taylor’s pussy in much more detail. She started rubbing her clit. When she found it to be working, she licked it and then started sucking it like her life depended on it. When she inserted her two fingers and curled them inside like she enjoys masturbating herself. This time, it worked wonders on Taylor.

“Fuck yes. That’s what I was talking about. Yes, right there. Faster with the fingers. Oh, my god. Oh yes. Perfect. Don’t you dare stop. Oh, my god. Faster. Harder. Yes. Oh… I’m… Cum…” Taylor’s voice stopped mid-word as she came hard on Jessica’s mouth.

Jessica waited, kneeling in her place for Taylor to calm down from her orgasm. When she saw her much calmer, she said, “How did your slave performed mistress?”

“You learned faster, but since you irritated me first, go again.”

This time, without hesitation, Jessica went down again with increased vigor. Taylor reached in heaven from the get-go. “Oh… Fuck… She’s good… Wow… Oh the tongue… Yes… Fuck…” Taylor repeated the words in a loop with her eyes closed and her hands on the back of Jessica’s head, pressing it down. This time, she came even harder than before. Now satisfied with the slave, Taylor got up from the chair and patted Jessica’s head like a pet.

Another naked white girl took her place, the girl with Rick. She introduced herself. “I’m your mistress, Karen. Now professor whore, let’s see what you got.” Jessica thought that she might have seen her somewhere before but couldn’t recognize. As she was about to go down on this brunette, she felt a hard smack on her ass. With a shriek, she turned to look and found Rick behind her.

“Now a whore can’t leave all the men hanging with blue balls while she satisfies women, can she? Stand up,” commanded Rick, following another hard smack on her other ass cheek.

Jessica stood up. Rick said, “Legs wide open, knees absolutely straight, bend over and focus on satisfying your mistress. I’ll take care of the rest.” She instantly followed the instructions with no hesitation. As she ate the second pussy of the night, she felt the head of the first cock of the night entering her cunt. Karen closed her eyes, laid back comfortably on the chair while putting pressure on the back of Jessica’s head with her hands.

Rick got into a pleasant rhythm. Claire couldn’t resist anymore and walked up to this erotic sequence. She placed her hands between Jessica’s legs from under and started rubbing her clit while Rick increased his speed. Rick started smacking her ass cheeks hard with each thrust.

This was too much for her and she couldn’t pull her head up to beg them to stop because it was getting impossible for her to control her orgasm. Only way for her to beg was if Karen had her first. She increased the intensity with both her tongue and fingers on Karen’s pussy.

“Oh… Fuck… Yes… I’m… Oh… You have no… idea… what… you’re doing… harder… yes… oh… I’m…” and with that Karen came hard on her mouth. She was still on cloud nine and wanted to prolong that feeling. She yelled out loud in her euphoria, “I want another. Carry on. Keep fucking me with that mouth. It feels so good.”

With no choice, Jessica continued. Her brain was screaming at her, “There’s no time. You cannot control any longer. They will punish you, but it’s not possible any longer. Cum now.” Against all the loud screams inside her head, Jessica did the impossible and kept her under control. She cannot follow through with the punishment to fuck all men in the neighborhood. She reminded her to do whatever needed to control her orgasm.

Karen came hard again under the newfound rhythm by Jessica. She was taking her frustration out on the pussy in front of her. This feeling was so good that Karen wanted even more. She wouldn’t let go of her head. In next few minutes, she had two more mind-blowing orgasms when she could take no more.

As now Jessica could speak, she said under heavy breaths, “please master. Please let your whore cum. Please. Your whore can’t control anymore. Please.”

Both Rick and Claire were vicious to her. Her entire body was rigid and shaking with the tremors of her “impossible resolve”. Tyrone replied to her begging, “let’s knock at some doors.” Jessica got her answer. She closed her eyes and started breathing heavily when the next girl was in front of her, the Latino woman.

“I’m Isabella. But you can call me mistress Bella. Let’s see what’s all the fuss about you.”

Jessica knew that eating the next pussy meant she wouldn’t be able to breathe properly to control her mammoth orgasm. But she had no choice. She started with no buildup. She now just wanted to be done with it. Bella didn’t have time to adjust to the feeling. It was instant, like Jessica was against a clock. In a way, she was.

She felt the cock in her cunt leave, and she thanked God for it. But the next was even more difficult as she felt a cold liquid applied to her asshole generously. She knew what’s next. Rick ravaged her asshole with one thrust and his entire shaft disappeared. He fucked her asshole hard, much harder. Claire added her two fingers in Jessica’s cunt while still rubbing the clit with her strong vigor.

Jessica’s knees gave up and she couldn’t keep her balance anymore. She fell on the floor. Rick’s cock and Clair’s fingers popped out of her holes. She wasn’t even eating the pussy in front of her. It was impossible to focus on anything anymore.

Jessica was in the fetus position, shivering like naked in Siberia. Impressive part was she had still controlled her orgasm. She hadn’t had her cum yet. But controlling longer was not possible. She begged, “please master. No more. Please, your whore begs you. Please have some mercy on your whore. Please… Please…” she kept repeating her begging words, unable to control her shivering.

Tyrone knew she’s done. It’s neither physically nor mentally possible to control the orgasm anymore. He gave a signal to Claire to leave her. Claire left her licking her soaking wet fingers. Jessica’s performance highly amazed and aroused her.

Rick was so close to his own orgasm that as she fell, he continued jerking. This would be impossible blue balls if Tyrone would say no to him as well. Before anyone could say anything, Rick came hard, dropping loads of cum on her tits. Jessica had rolled on her back trying to breathe heavily and control herself. She opened her eyes to see Rick standing on top of her with his legs on either side of her. Final few globs of his load landed right on her chin and lips. She didn’t know what to do anymore, so just laid there on the floor hoping for some mercy from her master.

This time Rachael walked up to her and said, “there are lots of people to satisfy whore. If you’ll give up now, then there’s no point. Eat that pussy in front of you. There’ll be a cock in one of your whole. I’ll give you freedom to choose which hole you want. And no, you cannot cum.”

Jessica looked into her friend’s eyes pleadingly, hoping for her to rescue. When she didn’t find any hope for help from her, she whispered shyly, “asshole.”

“What? I didn’t hear what you said, whore. Speak loudly and clearly. Beg these gentlemen to fuck your choice of hole.”

She didn’t expect her own friend to be this ruthless to her. Jessica had tears flowing from her eyes now, but she sat up. She wiped tears from her eyes and said, “This worthless whore begs all her masters to fuck her hungry asshole while she pleasures her mistresses.” Jessica felt her cunt was too sensitive at this point.

“Now, since that’s resolved, don’t waste that precious cum of your gracious master. Rub it nicely on your tits and clean your face and swallow it like a good hungry and horny whore should do,” commanded Rachael. Jessica submissively followed her command with no hesitation.

Soon she was back in her original position, eating the pussy in front of her while Jamie fucked her asshole from behind. By the time Jamie dumped his load deep in her bowels, Bella had three mind-blowing orgasms. Jessica had gotten much better with her oral skills, which unfortunately she won’t remember once the night was over.

As people on both ends changed, Jessica felt the power of all the water she drank earlier. She felt an urgent need to pee. Jessica turned towards her master and pleadingly begged to him, “master your whore slave needs to use bathroom urgently. Please, master. Your whore will follow all commands please let your whore relieve her bladder.”

Tyrone replied, “No. I’m showing you some mercy and your demands constantly keep on increasing. Now shut up and do your task.”

Jessica felt dejected by the words from her master, but planned to control her bladder as long as possible. The queue of men fucking her asshole is going to make it much more difficult. But she had no choice. Rachael returned with a whiskey tumbler and handed it to Jessica. She said, “I can see your asshole leaking your master’s precious cum. Scoop all that cum into this glass. Remember not to waste a single strand of cum deposited in your whorish asshole. All of it needs to go in this glass.”

Embarrassed, Jessica scooped as much cum as she could from her asshole into the glass and when she felt there wasn’t any more oozing out, she kept the glass away. Next woman in front of her was another black woman. She introduced herself as mistress Aliyah. Terry fucked her asshole next.

Aliyah’s clit was supersensitive, and her fingers found her g-spot easily. Aliyah kept coming often. She loved the feeling. By the time Terry deposited his load, Aliyah must have had at least seven orgasms. Jessica’s need to pee was increasing rapidly by the minute. She followed her orders and scooped Terry’s load as well to the tumbler.

Next combination was David from behind and Anna on the front. Jessica felt jealousy when Anna sat in front of her like any other mistresses. It was difficult to please Anna, orally for her. She was the only woman who came along with David. She only had her single orgasm by the time Jessica had a load deposited in her asshole. Rose ordered her to continue with Anna until ordered otherwise.

After Jessica had deposited the new load of cum into the glass, next cock in her hole belonged to Mark. He while fucking Jessica’s asshole started stimulating her clit. Jessica couldn’t control this pleasure. Her bladder was also killing her, and the extra stimulation was too much. For the second time in the night, she fell on the floor, shivering from her overstimulation and hard to control orgasms.

“Please, master. It’s too much for your whore. Please, she had to pee, master.”

“You know the answer. It will not change because you’re having difficulty controlling yourself,” responded Tyrone.

Reluctantly, she stood up and got in her position. In a couple of minutes, Mark started his stimulation on her clit again. He had too much skill and exactly knew how to push her buttons beyond her control. Jessica lifted her head and begged loudly again this time she was crying like a child, “Too much… Please… Master… Ah… Ah… Ah… No… No… Please… Stop… Can’t… God… Help… Help…” Then followed an ear-piercing scream from her. The control she was forcing on herself hurt her more than she ever remembered before. Her brain screamed at her to let go, but the fear told her to hold on.

Jessica surprised everyone with her resolve. Tyrone gave her some relief when he signaled for Mark to stop. Mark stopped completely and pulled his cock out of her asshole. It took her over two minutes of grunts and moans to calm down from the edge where she had reached. When in a better state, she said, “Thank you. Thank you, master. Your whore is grateful to her generous master for showing mercy on her.” She was still panting profusely.

She had her eyes closed, trying to not break the rules. Then she felt the cock entering her asshole. She looked back and saw Mark was back at fucking her again. Jessica forced herself back into Anna’s cunt. Mark just couldn’t control his cunning desire to torture her as he brought his fingers back on her clit. He signaled Anna to hold her head in place so she couldn’t beg anymore. Anna followed his command and kept Jessica’s face on her cunt. Finally, as he found she could no longer talk, he increased his intensity of both his cock and fingers.

Jessica couldn’t speak, but her loudest grunts told what she experienced. Mark was expert at what he was doing as he balanced her with his other hand so she couldn’t escape by falling on her knees as well. Jessica did something he wasn’t expecting, she clenched her asshole so fucking her faster got difficult. He smacked her cunt hard and yelled at her, “open up or you’ll regret it.”

Her cunt had become supersensitive from all events of the night and the smack felt hundred times worse than it should have under normal circumstances. She instantly relaxed her asshole with absolute fear. The constant strength she had to muster for this extended period to control her orgasm along with the lack of oxygen, she passed out again. This was the first time she passed out without having her orgasm. She passed out because she controlled more than she could handle.

Tyrone walked up to Mark and said, “don’t push her too far where no one else can enjoy her. You know the plan, so don’t deviate from it. I won’t tell you again. Fuck her asshole and leave that sensitive cunt alone till I give the permission.”

“Sorry, boss. I couldn’t control myself, won’t happen again,” replied Mark.

Jessica woke up feeling exhausted already. She looked at Mark, still rock hard, which meant it wasn’t too long that she had been out. He helped her up and forced her back into her earlier position. She turned her head back and begged, “Not the cunt master. Please, it’s too sensitive.” Without responding her he inserted his cock all the way in her asshole in a single thrust. Jessica licked and fingered Anna’s cunt again. All three of them were back in the rhythm.

Anna came first, followed by Mark. Relieved after feeling Mark’s cum in her asshole, Jessica took a deep sigh for not breaking the rules. She deposited Mark’s cum into the glass. Then she realized that controlling her bladder would be more difficult than controlling her orgasm now.

David followed next, and Anna was still in the chair. By now, Anna’s cunt was also hypersensitive because of multiple orgasms. Like Jessica, Anna also didn’t have a choice to leave the chair until Rose gives her permission to leave. Thirty minutes later when David deposited his load inside Jessica, Anna have had countless orgasms. Jessica now felt jealous of Anna, but she didn’t know that by now it had exhausted Anna. She also wanted to get out of this situation as much as Jessica.

Reggie fucked her next, but she had figured out a way to control herself while transferring all her frustrations to Anna. It was Anna now who could no longer control her orgasms, which appeared every few minutes. Both were hypersensitive to touch on their cunt, but Jessica also had another problem. Her desperate need to pee.

Only man in the house who hadn’t fucked her so far was Tyrone. This brought a realization to her. He had shown no interest in fucking her so far. She thought to herself, what’s the purpose of all this if he doesn’t want to fuck her? Why doesn’t he want to fuck her? She thought maybe if she could please him, she might get the permission to pee.

Jessica crawled her way towards her master and offered him, “Master, your whore had pleased every man in this house apart from her own master. May this whore have the privilege to please her generous master in any way he wishes?”

At that same moment, she heard the doorbell. Tyrone replied, “not all men yet. Crawl your way back and open the door. Invite our new guests inside with passionate kisses.”

Disappointed at her small window to get the permission, she crawled her way back to the door. She stood up and opened the door wide open to a complete shock. Before she realized anything, her instant reactions took over, and she closed the door back again. Jessica could not believe that Steve, Ray, and Nia were standing outside her house. She cannot go ahead with this degradation. These are the people who are close to Jason. This is too close. Her brain yelled at her to run inside her bedroom and shut the door till everyone leaves her house. But she knew doing that would have much more serious repercussions.

Tyrone shouted at her, “what the fuck do you think you’re doing? Open the door and invite our guests inside.”

She wanted to do it, but her hands would not move at all. Jessica couldn’t muster enough courage to face them in such a degrading situation. This will break her spirit. She had adjusted to fucking strangers and acquaintances, but friends were off-limits so far. How could she cheat on Jason with his friends and work colleagues? That is just too much.

“I will count till ten and if you don’t open the door and invite our guests inside by then, we’ll go out and knock some doors,” threatened Tyrone.

After hearing the threat, she realized there was a much worse thing at stake. Even before he could start the counting, she gave up and opened the door. She had her head bowed down, staring at the floor. Jessica couldn’t muster enough courage to look into the eyes of her friends while in such a degrading whore attire.

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

All three walked in and Nia gave her a passionate kiss on her lips while her fingers playing with her clit. Both Steve and Ray repeated same gesture. Ray lifted her chin and, while looking into her eyes, said, “I knew since our college days that you’d make a perfect whore. Finally, your dream became a reality. There’s no way that miserable and tiny cock could satisfy your whore cunt.”

Jessica’s eyes were moist again. Ray lusted over her ever since he was Jason’s roommate during college days. He was still a bachelor. And never found the right woman for his kinks. When Steve found out about his kinks, he invited him to join his exclusive club. Ray was the one to tell Steve about Jessica and convinced him she would be the best performer for their club. Jessica was the first woman who he couldn’t tame on his own, which increased his frustration and want for her.

Steve sat down on a chair and ordered Jessica to sit on his lap, facing everyone else. Jessica followed his order with both her legs spread on either side of his legs. She leaned her back on his chest. His chin rested on her shoulder, with him breathing softly in her ear. He whispered, “Now stay calm and answer all questions by Ray. Your answers will determine what we’ll do to you next. If we’re not happy with your answers, you might suffer a lot worse than you could imagine.”

Jessica nodded, signifying that she understands. Steve brought his hand around her and started pinching her nipples along with the other hand, gently playing with her clit. Her clit was by now hypersensitive, but he didn’t care about it.

Ray got the signal from Steve and asked his first question. “I heard that your hubby, Jason, has a tiny penis. Is that true? Tell us more about how he is in bed?”

Jessica saw he was recording a video on his phone. Everyone gathered around to witness her humiliation. The video showed both her and Steve’s face perfectly. Aroused and frustrated from the past couple of hours. Her brain couldn’t make coherent thoughts. She needed to get over with all this, and the only way for her would be to do as they please.

“Yes, he has a tiniest penis you could ever imagine. I can’t even feel when he’s completely inside me and he also suffers from premature ejaculation. Most time he’s done in four to five thrusts. It is very frustrating for me. That’s why I had to look elsewhere for my physical needs,” lied Jessica in hopes of them to stop their torment.

Jessica had already said these humiliating lies about the love of her life before, but it felt much more miserable from within saying it again. Why? She thought it’s possible because earlier she said those words in front of strangers and she didn’t know they were recording. This time she’s in front of people who know Jason very well and she knows they’re recording. But something she felt guilty about was the increase of arousal. Just saying those words brought a surge of arousal within her. Plus, Steve’s fingers weren’t helping the cause.

Nia walked up to her and attached a leash on the metal ring of her collar. The ring was in front of her collar, vertically in between words “PROFESSOR” and “WHORE”. From her moist eyes, she looked in shock towards Nia. There was a huge fog of desperate lust in her eyes. She couldn’t think straight anymore. They had prolonged her denial, and she was getting excessively desperate now.

“Always say yes to all the questions,” whispered Steve in her ear.

“Does Jason know his wife cheats on him while he’s away from home?” asked Ray.

“Yes. I mean, he must know by now. His… Oh… Fuck…” she couldn’t speak anymore because of her extreme edging. She was again struggling to control herself.

“Continue,” whispered Steve.

“Oh, someone please fuck me. I desperately need to cum. Please.”

“Answer the questions first, then maybe we will fuck your whore cunt,” said Ray from behind the phone’s camera.

“I haven’t told him specifically, but I assume he would definitely know that his wife is cheating. There’s no way he thinks I’m satisfied with his pathetic cock,” said Jessica in between her heavy breaths.

“Would you take any cock in your cunt to satisfy your needs?” asked Ray.

“Yes. I will take any cock in any hole to satisfy my needs.” Her desperation was clearer by each second now.

“How many strangers have you fucked so far behind his back?”

“I honestly don’t know. It’s too many. Please, I’m… Ah… Ah…” Steve had inserted three fingers while rubbing her clit and his fingers hit her g-spot perfectly. “Oh… Please… I need… cum… pee… fuck… pee… cum…” Her brain couldn’t decide what she needed more, to pee or cum.

“What do you want?” asked Ray.

“I need… to pee and cum. Please, help me.”

“Choose one.”

“No. Please, I can’t… I… fuck me… Oh… can’t please…”

“I can’t allow both. Choose one.”

“Ah… Ah… I can’t… Please…”

“What do you think, Steve? Should we allow her both?”

“Not without something in return. What can you do for us in return, whore?” asked Steve.

“Anything. Please, I’ll do anything.”

“Okay, let’s see then. You’ll crawl like a bitch in heat with your leash in Nia’s hand to your neighbor’s house and pee on his porch. You will then ring the doorbell and crawl your way back to your own house. This is the only way we’ll allow you to pee or cum tonight. We’ll be generous and allow you to choose the house.” Steve enjoyed giving such humiliating and risky task to her.

Jessica couldn’t believe her own ears. This couldn’t be the task, it’s too risky. Her neighbor can catch her in the act, and it’ll destroy her reputation. But her body’s need overpowered her logical thinking. She could not control any longer. Now the thought process was to remember which neighbor doesn’t have security cameras securing their house. She needs to choose a house where she’ll not be recorded. She remembered; Manson’s family house didn’t have a security system because Charlie Manson is too paranoid that if he had cameras in his house NSA will spy on him.

Only problem, his house was five houses away and across the road. That’s too much crawling in such a vulnerable and humiliating attire. But it’s the risk she’ll have to take. Plus, it was past midnight by now and she knew most of her neighbors would be asleep by now. She decided and told them she’ll crawl her way to Manson’s house.

Rachael walked up to her and gave her knee pads. She said, “put them on my pet. I wouldn’t want to see my pet hurt doing her task.”

Jessica looked at her and felt anger, disgust, and betrayal inside but outside she said, “Thank you, mistress.” After wearing the knee pads, Jessica was now on all fours. Nia grabbed the leash and yanked it so she could follow her. As they reached the front door of her house and about to leave, she heard Steve’s voice, “wait a minute.”

He came to them and pushed a giant dildo into her asshole. She screamed loudly because of the sudden unexpected invasion, but then adapted to the size. With the press of a button, the dildo inside her asshole started vibrating ferociously. Jessica gasped, audible to everyone. It would be extremely difficult to crawl to Manson’s house with this much arousal. The vibrations were so intense that she felt she would cum and pee any second. And then they left the house.

Now the video switched to the phone’s camera view, which she assumed was Ray’s phone. In the video, she realized that the dildo in her asshole was a dog’s tail. She was their bitch at this moment. Rachael smacked her ass hard and yelled at her, “raise that ass higher.” Jessica instantly raised her ass higher while continuing her crawl of shame. She looked around to see if anyone heard Rachael and was now looking at her disgraceful ordeal. When she saw no one, she took a deep sigh or relief and continued to follow Nia. Jessica had already told the exact directions to the destination.

Jessica’s heart rate was rising by the second. The risk of being found by her neighbors and the shame that would follow afterwards increased her arousal even further. The vibrating dildo already brought her to the edge. She was controlling. In her head she kept repeating, “Few more steps and you can have your relief. You have done it so far, just a few more steps. Hold on.”

Finally, the moment arrived. Jessica was now sitting on her knees, hands locked behind her back and legs spread wide open. She was on the porch of Manson’s house, few feet away from the front-door. This was the moment, and the dildo in her asshole was sending exceptional pleasure sensations to her entire body.

“What do you have to say, whore?” said Ray in a loud voice.

Fear struck Jessica, asked, “May your dirty whore slave have the permission of her generous master to pee on the porch of her own neighbor’s house? Please, master Ray. Your whore will serve in whichever way her master deems fit. Please let your nasty whore pee.”

“Start rubbing your clit right now,” commanded Ray. Jessica instantly followed the command. “Harder like your permission depends on it.” Reluctantly, Jessica obliged with the command. It made it much harder to control now. She couldn’t control her grunts anymore. They got much louder.

“What do you want more? Pee or cum?” asked Ray.

“Both. Master, your nasty whore desperately needs both. Please. Ah… impossible… it’s imp… now… please…. Oh…”

“Pee now, whore. Fingers working the clit.”

Jessica yelped loudly as her bladder released the warm liquid out. It took her over a minute of high-pressure release to discard all the piss out of her system. Her desperate need to cum instantly replaced the relief she felt afterwards. “Thank you, master. Please, may your whore cum now? Please master, let her cum now.”

She kept waiting for the permission which didn’t came for the next few minutes and her edging had reached beyond her limits now. As she thought there’s no conceivable way to control any longer, she heard the words, “cum now whore.” With a loud grunt, she came hard. When Ray saw the amount of ejaculation sprayed out of her cunt, he thought she was peeing again. It was a ridiculous amount of fluids released from her hole.

Few minutes later she was still panting profusely. She felt a whole new euphoria and was ecstatic. Jessica released an unbelievable amount of frustration out of her cunt. She felt fabulous. She couldn’t admit it to herself. As she came down from her euphoria, she heard the next command from Rachael, “suck those nasty fingers clean.”