tagIllustratedJesse's Journey Down a Rabbit Hole Ch. 05

Jesse's Journey Down a Rabbit Hole Ch. 05


As I mentioned in the previous chapters, this story is a collaborative effort between me and Rebeccsm. She has provided the art, and a lot of the plot, god I love how her mind works, and me for the text. Please let us know how you feel about our efforts. Comments and votes are welcome. It is the only way we will know if you like our work.

I would like to thank everyone who read the previous chapter and we hope that this chapter is even better. This story is about an empty nest mother that discovers her submissive side and decides to pursue her desires. But as you may well know that is a slippery slope and it is easy to get in over your head. It also contains non-consensual sex and forced exhibitionism. Please if this is not what you want move on. I want to thank Arilyn99 for her efforts in editing these chapters. All persons portrayed are figments of our imaginations and are over 18 years old.

It was Monday morning and the start of a new school year. Jesse was struggling to get out of bed. Her entire body hurt as yesterday was spent catering to every whim that Master John could think of. After Master John and Master X had finished talking, Jesse and Marcus were both frightened. With Master X, they felt like they could quit if things got out of hand, but now that John was involved both knew that escape would be more difficult. The final nail in their coffin was when Master X announced that he had taken control over their finances. When Jesse asked about their children at school, Master X laughed. His next comment chilled her to her marrow. "Your money is now my money. If your kids need money, I guess you're going to have to earn it."

It seemed that John took particular pleasure in humiliating Marcus. His duties were now to clean up after every fuck. John made sure he swallowed every drop of his cum.

Jesse slowly walked to the bathroom. She looked at her husband still sleeping on the floor. She wanted to go to him and give him some relief, but her orders were clear. She was not to help him in any way. Oh he looks so uncomfortable lying there. How can he sleep with his arms pulled back and attached to his ankles? She wondered to herself.

She looked at his face crusted with dried cum. His cock was still red from John's whipping. She stepped over his body and walked through the door into their bathroom. Jesse stood in front of the mirror and cried when she saw her body. Her ass was bruised and covered in welts. Her face was covered with John's dried cum. Her tits had sucker bites all around each nipple. She slid her hand between her legs and winced when she touched her lips. Between the spankings she had received and the multiple fuckings, her pussy was very sore.

Jesse climbed into the shower and let the hot water revive her aching body. Twenty minutes later she was sitting at her vanity fixing her makeup and hair. Her orders were clear. She was to dress in a white, button up blouse, black lace, half cup bra, and a black pencil skirt that came to just above her knees. Completing the outfit was a pair of 4" stiletto heels that strapped around her ankles. The skirt and blouse were so tight they were more for going out clubbing than teaching school.

When she was finally dressed, she headed downstairs to the office. She pulled up the browser and opened her email. At the top of the list was an email from Master X. It contained her other instructions for the day.


You are to wear the clothes selected for the day. You must leave the blouse open far enough to see your bra. You will flirt with every cock you see today. I want you to edge yourself during each class for 15 minutes. You may sit at your desk, but your hand needs to be buried in your panties. You are not allowed to cum under any circumstances! During your free period, I want a picture of your tits in your classroom. It must show your tits, face and your classroom in the background.

You will make sure you expose your bra to at least one student in each class. On your way home you are to remove your skirt and toss it in the back seat. The entire way home you are to play with my cunt and you'll send me a picture. You are not allowed to put your skirt back on once you have removed it.

Master X

She closed that one and opened the second message, also from Master X


There is a bag in your car. In it are a few things you will also need today.

  1. You will take the first webcam, remove the adhesive pad cover and place it under your desk and point it at your love box. Take your phone and turn on the hotspot. I will take it from there.

  2. Insert the Ben Wa balls in your sloppy fuck hole. Whenever you are not edging, I want you to be walking around your classroom.

  3. Take the other four webcams and place them in each corner of your classroom. Make sure each of them has a clear view of the room.

  4. Take the two pieces of sandpaper and place them in your bra cups. Don't play games and don't try anything funny!

  5. After your last class, change into the outfit provided and meet John outside the school for further instructions.

I will be watching and giving additional tasks during the day. As long as you obey, your tasks will be easier. Disobey and you can expect something humiliating. Enjoy your day, slave.

Master X

Jesse read the second message and cringed. She'd tried Ben Wa balls once for Marcus when they had gone out for dinner. It took everything she had to keep from cumming just walking from the car to their table. Marcus had kept her walking all night. Jesse remembered the orgasms. She had three, one in the restaurant and two walking around downtown. How could she manage at school?

Jesse pulled into the faculty parking lot. It was early and only a couple of cars were there. She grabbed the bag and her things and walked toward the door. Just before she got there her cell phone buzzed.

Thinking it might be Master X, she sat down the bag and answered. She was glad she did, "Yes Master X, what can this slave do to please you?"

Master X loved every word. Even though he knew her spirit wasn't broken, he also knew it wouldn't be long that those same words would have a completely different meaning.

"Unbutton your blouse slut." Was all that he said and the phone went dead.

Jesse stood there a few moments before she looked to see if anyone was around. As she was doing that, her hands were already opening the last few buttons on her blouse. The breeze opened the blouse completely. Her tits, still encased in the black half cup bra were on display for the entire world to see. Jesse groaned as a spasm of pleasure pulsed out from her core to her extremities. That was followed by a wave of humiliation almost sweeping her off her feet.

In her mind, all she could think of was one of her hard limits on her paperwork which was no nudity at school. One of her first tasks was to walk through school with her blouse open and her hands full. There would be no way to cover her tits before she got to her classroom. She looked to see if anyone was pulling into the parking lot, took a deep breath and walked into the building. As soon as the door closed, Jesse's body started to tremble. Her hands were having trouble holding onto the bags and briefcase. Her blouse was completely open and her nipples were on display for anyone to see.

Knowing if she stayed where she was she would certainly be caught, Jesse walked quickly down the hall. She couldn't go any faster as running in heels was impossible. At the end of the hall on the left was the main office. She had to stop by there and sign her timesheet. Jesse slid down the hall hugging the wall. When she got close to the office, she peeked around the corner. She breathed a sigh of relief when she saw that the lights were off. Jesse dashed the last few feet to the office door and stepped inside. As soon as she did, the lights came on lighting up the entire office like a stage.

Jesse yelped as her body froze thinking someone had caught her. She turned towards the door, but no one was there. Then she remembered that last year some of the rooms had been equipped with motion switches on the lights. She relaxed and hurried over to the timesheets. Just as she signed in, a voice came from behind her.

"Jesse, you're here early. Normally I'm the only one here at this time."
Jesse recognized the voice immediately. It was Janice Wilson, the Vice-Principal. She and Jesse had been up for the position and Jesse thought that Janice had slutted her way into the job. To say they didn't get along would have been an understatement. Jesse had her back to her nemesis and knew she hadn't seen her bra yet.

"Good Morning Janice. I didn't hear you come in."

"Oh I've been here for over an hour. I was in my office. If there's no movement, the lights go off. It startled me when they came on. As I said, no one is usually here at this time."

Janice watched as Jesse tried to keep from showing her tits, but it was already too late. Janice saw how she was dressed as soon as the lights had come on. She purposely waited before she revealed her presence to Jesse. At first she was going to bust her and get her fired. Coming to school with her tits out was certainly against the school moral behavior clause, but before she spoke, an idea popped into her head. She might just be able to use this. She pulled out her phone and started to video the obviously nervous teacher.

Janice waited to see what Mrs Grabas would do. When she didn't move to leave the room, Janice upped the pressure and walked over to stand next to the shaking teacher. Jesse noticed her movement, and turned in the opposite direction. She was now facing away from the door and toward a short hallway leading to Janice and Principal Owens offices. She was trapped and her body was betraying her as her dripping pussy pulsed again.

Jesse felt rather than heard Janice move closer to her and she moved further down the hall. She was now fully into the hall and Janice had her trapped. She brought her hands up to try and button her blouse when Janice grabbed her shoulders and spun her around. Jesse was so surprised that her arms, bags and everything else went flying. Janice's eyes were wide as saucers when she saw Jesse's breasts bouncing out of her bra and proudly on display.

Jesse was frozen in place. The look on Janice's face scared her and she knew she was about to be fired.

"Please Mrs Grabas, explain to me, why on earth you are walking around school with your breasts hanging out?" Janice demanded of the frightened Jesse.

"Please Janice! It was just a bet I made with Marcus. No one was supposed to be here. Please don't be rash. No one saw me." Jesse tried to explain.

"Oh, but you're wrong! I saw you and I took a video of you as well. I'm sure Principal Owens would love to see his star teacher half naked in the office." Janice replied with malice in her voice.

"Oh God Janice! Please don't, please! It would ruin my career. I'm begging you; have mercy! It was just a stupid bet." Jesse pleaded.

Janice watched as the slut squirmed and begged not to be turned in. "And tell me why I shouldn't turn you in? You were absolutely brutal trying to get this job, and you have fought against me on every issue. Have you shown me any mercy, slut?" Janice inquired.

"I'm sorry Janice. You're right I was... I am a bitch. Please! Let me make it up to you?" Jesse begged her.

"Make it up to me? Just what could, or should I say, what will you do to make it up to me?" Janice asked, toying with Jesse like a cat with its prey.

"Anything Janice, just name it! Do you want money? I can take on extra projects around school. I'll do detention duty. Just let me know what you want!" Jesse replied quickly, seeing a glimmer of hope.

"Into my office, now," Janice ordered as she pushed Jesse down the hall. As soon as they were both inside the office, Janice shut the door, gave Jesse an evil look and said, "STRIP," demandingly.

Jesse stood and looked at the Vice Principal standing in front of her with her arms crossed and a smug smirk on her face. She knew if she didn't comply her career in teaching would be over. She dropped her blouse on the floor, followed by her bra.

Janice simply flicked her fingernails, and Jesse knew what she wanted. Soon, Jesse was standing naked in front of the vice-principal.

Janice waited for a minute before she pointed toward the floor. Jesse was overwhelmed by her emotions, her brain just barely functioning. She dropped to her knees and stared at the floor as soon as she was able to figure out what Janice wanted.

"So Jesse, now that you are where you should be, on your knees before your better, please tell me, what you will do to make your behavior up to me?" Janice asked.

Jesse knew that her options were very limited. She was naked in her rival's office, and Janice had a video of her tits exposed in school. If she looked in the bags and discovered Master X's toys for her use, she might well end up in jail, if not prison!

"Please Janice! I will do whatever you wish, just don't have me fired." Jesse said, in a voice just barely above a whisper.

Janice was beyond excited! Her arch rival was surrendering to her! Having her naked and groveling before her was just a bonus.

"Okay slut, here is what I want you to do. Usually no one shows up for another half hour. So if you're good, your secret is safe with me, so long as you are obedient! Now gather your clothes and bags. I want you to walk to your room naked except for your shoes. I want you to walk, not run, and I'm going to take a video of you as you walk down the halls. When you get to your room, you will drop your bags and play with your dripping cunt outside of your door." Janice ordered the subservient Jesse.

Jesse inhaled sharply knowing that, as bad as the video of her exposed tits was, this would be much worse! Unfortunately, her options were quite limited. She looked up at the now dominant Vice Principal and nodded. Janice smiled and watched as Jesse gathered her clothes and put them in one of her bags. She slowly stood and walked out of the office and into the main hall. All the while Janice was taking a video of Jesse's naked body: Sometimes as she was walking towards her and other times from behind. All the while Jesse's was slipping deeper into subspace and with each step, her submission became more complete.

Jesse arrived at her classroom door and glanced at Janice standing behind her with her phone pointed toward her. She dropped her bags by the door, and leaned against the lockers that lined the hall. Her hand slipped between her legs and her fingers found her sensitive clitoris. Jesse's gasp echoed in the hall as she stimulated herself. As her fingers slipped between her labia and as her thumb stroked her clit, Jesse's other hand grabbed one of her breasts and pinched its nipple. She kept on pinching the nipple harder until a moan escaped her lips. Then both hands began working together to release the orgasm that was about to consume her.

Janice watched as Jesse, completely unaware of her surroundings, started to climax. As her body stiffened and began to explode, Janice called out, "STOP SLUT!"

Jesse stopped, looking at her tormentor. "Please Janice! I need to cum, bad!" she whined.

"Not right now you don't,slut! I am in charge and from now on, you do as I say! Now, get in your room and get dressed, slut!" Janice commanded, as she turned and walked back down the hall.

Jesse quickly grabbed her bags and hurried into her classroom. Once inside, she collapsed on the floor and cried. Just two weeks ago this would never have happened. Now both she and her husband were on the path to sexual slavery and Jesse knew it. The fear of their impending slavery only served to heighten her arousal.

Jesse also knew her time before classes began was limited, so she grabbed her clothes and started to take care of the tasks enumerated by Master X in his email to her this morning. She took the Ben-Wa balls and shoved them deep inside her vagina. She then slid her panties up her legs, effectively sealing them in. Jesse slipped on her skirt and blouse, makings sure that the blouse showed her bra. Jesse looked at the time and realized that she still had lots of time before her first class.

Grabbing the first webcam, she dropped to her knees and stuck the camera to the modesty panel on the front of the desk, pointing the camera directly between her legs. She turned on her phone's hotspot and grabbed the remaining cameras, installing them around the room. By the time she got back to her desk, her cunt was already dripping again.

Shit! I only walked from one end of the room to the other and I'm already on the verge of another orgasm! God! I hope it's not just from the Ben-Wa balls! If I get this aroused from one trip around the room, I won't last through the second period without cumming!

She sat at her desk and tried to calm her body down before classes started.

John watched as Jesse left for school. He smiled when he saw the outfit she was wearing. It was acceptable for school, but just barely. John and Master X had worked out a deal that Master X would control Jesse at work and outside of school, while John controlled her when she was at home. Together they worked out a plan to keep both Jesse and Marcus constantly aroused and humiliated.

Master X loved the idea of the poker game and making Marcus lose his wife to John and his friends. It was John who had decided that Marcus would clean out his wife each time she was fucked. John's goal was to make him a cock sucking ass slut.

Now that Jesse was gone, John headed across the street and into his slave's house. He climbed up the stairs, and stood over Marcus, who was still hogtied on the floor. He knelt down and smacked his ass hard. Marcus groaned as the pain from his ass being smacked only made his arms and legs hurt more.

Marcus looked up at John with tears in his eyes and asked: "Please Master, may I go to the bathroom?" John laughed at his misery and pulled his arms back a little further causing Marcus to squeal in pain.

"Are you going to be a good slave, Marcus?" John demanded.

"Oh yes master! I will do whatever you command, just please release me." Marcus begged, whining a little.

"That takes in a lot of territory; whatever I command. Are you sure, slut?" John asked, playing with Marcus a little.

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