tagIllustratedJesse's Journey Down a Rabbit Hole Ch. 06

Jesse's Journey Down a Rabbit Hole Ch. 06


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.

Jesse walked out the main door of the school. Master John was waiting for her in the drive. He was dressed like a slob. He was wearing an ugly Hawaiian shirt and shorts. His fat belly was straining the buttons on his shirt. Jesse had changed to a matching skirt and top. The skirt didn't even come to mid-thigh and the top was very tight and open to below her tits. With every step her tits were threatening to pop out at any moment. John gave her with a leering smile. Jesse felt so humiliated that everyone in school would see her getting into his car dressed like a whore.

Jesse tried not to look at anyone but her Master. He opened the door and ordered, "Take off the skirt; I want to see your sloppy pussy, slave."

Jesse cringed, but did as he ordered, praying no one was watching.

John walked around the car and got in. He started it, smiled, and commanded, "Slut, pull out those puppies, I want your tits out in the open."

Jesse pulled the top open and exposed her tits. The seat belt went between her tits and only brought attention to her bare chest.

"I can't wait to get you some respectable clothes to fit your new slut self." John said as he leered at her exposed tits. It took them almost 20 minutes to get to the specialty boutique that carried the club wear that John wanted for the slave. When they pulled into the parking lot John smiled and said, "Now that we are here and I can enjoy it, get up on your knees and suck my cock while showing everyone your ass." A tear ran down her cheek but she did as ordered.

Jesse's body was shaking she was so excited. Sucking Master John's cock was repulsive, she hated doing it. She hated him and being forced into sucking his cock in a car was completely demeaning. But Jesse was more aroused at that moment than at any other time in her life. Her cunt was exploding with her fluids. Her nipples were hurting they were so hard. She had an orgasm when he spewed his seed down her throat, despite her best efforts to maintain control.

John sat there watching the slave tremble as her orgasm pulsed through her body. He waited till she started to come around and handed Jesse her skirt. "Get dressed and let's go. I want to introduce you to someone."

Jesse slipped the skirt up her legs and put her tits back into her top. John got out first and opened the door for Jesse. She stood on shaking legs and held his hand. She was still a bit dazed from the massive climax.

Jesse's head cleared rapidly as they walked down street. She felt and looked like a hooker, and being led by Master John only made it worse. They walked about a block when out of an alley stepped a thin black man. Jesse was about to ignore the man when she heard John speak.

"Hey J-man, what's up."

"Fat John, right on time my man."

"So J-man, this is the slut I told you about. She's going to need some money soon and I'm thinking you can help."

"Sure Fat John, that's some fine pussy, I think we can work something out."

"Great, we're on the way to update her wardrobe, wanna come along?"

"Don't mind if I do. We can get to know each other." J-Man said as he leered at Jesse.

Jesse was now frightened at the conversation. She never signed up for prostitution. She started to pull away but John squeezed her hand tightly and glared back over his shoulder. She knew that even if she were able to break away, She had nowhere to go? She didn't have any money or ID. Jesse wasn't even sure where she was. She decided to wait until she was sure she could get home. The three continued down the street until they came up to a brightly lit boutique: BARE NECESSITIES. Jesse cringed thinking about what was going to happen.

They entered the store and were greeted by a pretty young redhead. She was chewing her gum and looked at Jesse like she was beneath her.

"My name is Mandy. What can I do for you Sir?" She asked politely.

"We have an appointment for a new wardrobe for my slut here." John said proudly.

Mandy looked at Jesse and snickered, "I think we can dress her like the slut she is. Follow me Sir."

Jesse was blushing down to her toes. She wanted to scream out that she was a respected teacher, but how would she explain her current dress or Master John. The humiliation was overwhelming and absolute. She dropped her head and closed her eyes, her body pulsing with arousal.

Mandy led them down a short hall to a dressing area. She looked and smiled, "Okay slut strip, let's see what we have to work with." Mandy looked at John and asked, "Kind of old isn't she? I mean she hasn't dried up or anything has she?"

Jesse almost died on the spot; Mandy's words cut her to the bone. She couldn't even look the young woman in the eyes. She could only follow orders and stripped in the middle of the room. By the time she was down to her panties, Mandy handed her some clothes and pointed towards an open changing room. Jesse slipped on the dress and slid the stockings up her legs. The outfit consisted of a red lace sleeveless dress that had fine netting above her tits. The straps formed a collar around her neck. It was so short that the tops of her red heart stockings could be seen. It was actually very pretty if Jesse was going out clubbing. But she knew that wasn't where she would have to wear it.

Mandy looked at the slut standing in the open dressing booth and giggled. "Well it's okay, but I think we have something much better. Take it off slut."

J-Man walked up to Jesse as she stripped off the lacy dress. "I like her with or without the dress. That's one fine piece of ass." All three of them laughed as Jesse blushed again.

Over the next hour, Mandy had Jesse try on several outfits, each a little sluttier than the last. Some even came with accessories.

Finally Mandy had Jesse put on a black leather bikini. It had chain covering that draped over her tits, and a collar that had a belt which went down her back. Mandy had Jesse reach behind her and grab each elbow. She took the belt to bind her hands. When she pulled the humiliated slave out of the dressing booth, she turned the slave around and let the two sleazy men inspect her red ass from her earlier spanking. Both men caressed her ass before Mandy turned Jesse around.

When Jesse was facing Mandy, she gasped when Mandy showed her the accessories that came with the outfit.

Jesse gasp wasn't from fear, but from arousal. The thoughts of being gagged and plugged in the store only fed her humiliation and drove her arousal higher. Finally Master John was happy with the selections and called an end to the show. Jesse was now wearing a blue tunic dress that covered nothing. They paid for the purchases and walked out the door.

Jesse was very quiet all the way back to her car. Master John had her strip off the barely-there dress and ride naked. Jesse was so wound up she was trembling. The clothes Master John picked out were worse than slut wear. There was no way she could wear any of them in public. Just the thought made her dripping cunt gush. When they got to her car, Master John tossed her the clothes she had worn to school. "Put these on slut, you know how to drive home." he growled. He waited for Jesse to dress and kicked her out of the car. Jesse rushed to her car and jumped in. She sat there for a minute and watched as Master John drove away. It had been a very long day. Her body was hotter than it had ever been before. She hated Master John, but what he did to her drove her to new heights. She put the key in the ignition and started the car. Just before she put it in drive, she remembered Master X's instructions. She looked around the deserted parking lot and saw no one. Relieved, she unfastened her skirt and pulled it down her legs. Now sitting in the car almost half naked, she placed her phone on the dash, pointed it at her body and pulled up the camera app. Knowing what Master X wanted, she put the car in gear, dropped her hand to her dripping cunt, and started to stroke her clit. By the time she got to the freeway, she was once again on the cusp of a massive climax. She reached up and took the first picture.

The ride home was very difficult. Jesse had trouble concentrating on the traffic, which was now bumper to bumper. She did as ordered, and played with her clit the entire way home. By the time she arrived, the only thing on her mind was to get fucked. She didn't care by who or what, she just needed to get laid. Jesse opened the door, jumped out and ran in the house.

Unbeknownst to her, her neighbor was watching her too.

Jesse dashed in the door trying to keep out of sight of her neighbors. She rushed upstairs and fell on her bed. She was crying hysterically as it finally hit her. Neither Master X nor Master John cared for her. She was nothing more than a slave to be used. It didn't matter that she was a teacher. Her and Marcus' lives were in their hands, and it seemed that they were trying to destroy them.

It was only a minute or so before Master John showed up at her bedroom door. "Get up slut, it's time to exercise. Get dressed and downstairs in 5 minutes." He turned and walked down the hall. Just before he got to the steps, he turned his head and yelled, "And don't ever close a door again. You will always leave the doors open. You are not allowed to have any privacy."

Jesse had jumped when Master John barged in. She was trying to stop crying, but the feeling of being helpless was all encompassing. Now it was worse because it was mixed with a feeling of hopelessness too. She opened her dresser, pulled out her tiny exercise outfit and put it on.

Jesse walked downstairs right on time. Master John chuckled at how her outfit hugged every curve. "You're going to be very popular in the neighborhood from now on. Now come over here and suck my cock. Today you're going to run with cum on your face.

Jesse's head dropped but she slid down to her knees and swallowed her Master's cock. She worked her mouth up and down the shaft lavishing her tongue up and down the large cock. In spite of her state of mind, sucking his cock actually helped. It was as if it was a pacifier and calmed her mind and body. Because Master John had cum twice already today, it took Jesse almost 20 minutes before he finally shot his load all over her face.

"Now you look like a slut. Remember, you warm up by doing each exercise for 5 minutes. Then it's a 2 mile run and I better not hear of you trying to cover up or wiping your face off. Now get started, slave."

Jesse stood and walked out the front door. She stepped off the porch and stood in the front yard. She looked up and down the street hoping her neighbors weren't out. Seeing no one, she started with stretching for the required 5 minutes. Then it was touching her toes for 5 minutes. By the time she finished with that she was covered with perspiration. The next warm up was putting her hands behind her head and doing deep knee bends.

By the time she finished warming up, she was covered in sweat and her Master's cum. She looked around and started to run.

When Jesse finished her run, Master John's seed had mixed with her sweat, slid down her face and now covered her tits. It made a sticky mess and made her feel even more like a slut. She turned down her street and saw her creepy neighbor standing on his porch. Jesse didn't even know his name. All she knew was that he was disgusting and leered at her every time he saw her. Jesse jogged down the street until she got to her front yard. She knew her instructions, but she wished that her neighbor wasn't out watching her. Any thought about not doing as she was told never entered her mind. She started her cool down routine. Unbeknownst to her, the disgusting neighbor walked up behind her.

Jesse didn't know how close he was until she stood after stretching her back. She turned and he was only a couple of feet behind her, staring at her ass. She reacted before she thought and smacked him on his right cheek.

She blew up and yelled at him, "What the fuck are you looking at, you creep? Go away and quit gawking at me."

It was the first time in a long time she had stood up to a man, any man. As soon as she said it she looked at her house, praying that Master John or Master X hadn't seen her outburst. The last thing she wanted was for them to use her neighbor to humiliate her. She turned, walked up the driveway and into the house.

Marcus was just inside the door when she walked in. He smiled at her as she stripped off her running shorts and top. She was naked, covered in cum and sweat. Marcus gave her a hug, whispering in her ear, "We need to do something about next week when the kids come home. We can't let them see us like this. I can't be wearing your panties and stockings around the house when they are here."

Jesse nodded and answered, "Let me take a shower, and we can talk to Master X. I'm sure we can work something out."

Marcus nodded, kissed her cheek and walked into the family room. What they didn't know was that Master X had heard the entire conversation. He smiled and waited for them to contact him, all the while wondering how much he could get for two days of freedom.

It took Jesse about 20 minutes to finish her shower. She walked out of the bathroom, and Marcus was sitting on the bed. He looked at his wife. He loved her so much, but since Master X had entered their lives everything had changed. Their neighbor John, with Master X's help, was now dominating both of them. Marcus had to wear Jesse's panties and stocking at all times around the house, and John was making his life miserable. Marcus had never sucked a cock before, and since their involvement with Master X, he had sucked John's cock a few times.

Jesse looked around and asked, "Where's Master John?"

"Do you have to call him Master John? I know he's working with Master X, but Master John?" Marcus asked.

"That is what I was told to call him. Is he still here?" Jesse asked again.

"No he had something to do with his wife. Why?" Marcus replied.

"Now would be a good time to talk to Master X about the kids' visit." Jesse said.

"I agree and I would like to get John pulled back a bit. I mean he had you walking around almost naked earlier." Marcus said, his anger rising.

The two of them walked into the office and turned off the screen saver. Sitting at his desk was Master X, his face in shadows as usual. Both Jesse and Marcus knelt down and waited until their Master acknowledged them.

"Okay slaves, out with it. Why are you disturbing me?" He growled.

Jesse was the first to speak, "Please Master X, we have a request. Our kids are coming home from college for a visit next weekend. We are asking that you give us a weekend off. We can't let them know of our lifestyle."

Master X almost laughed at her. "Slave I told you the rules. 30 days of absolute submission and complete obedience. If you fail, I'm gone and everything I've collected will be released to the world."

"Oh God, no! Please Master X don't do that! We've been good and have been obedient. It's just our kids won't understand. We're new to this and haven't discussed our slavery with them. Please Master X?" Jesse was begging now.

Master X knew it was just a matter of time before the two slaves would surrender everything to him, including their kids, but he loved to string it out and make them suffer.

"What do you say Marcus? You haven't said a word. Is this what you want also?"

"Yes Master X, I can't let my kids see me dressed like this." Marcus pleaded.

"Okay slaves, I'll give you your weekend off, but it will cost you. This is not negotiable; you either accept these terms or your kids are going to be very surprised. Do you agree?"

Jesse nodded, and Marcus looked at the shadow on the monitor, "I want to know the terms before I agree."

"Here are the terms:

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