Training my Sister Kayleigh Part 4

This saga is the sequel series to the “Playing Dare with Sis” series, which tells the story of how a brother coerced his sexy teen sister Kayleigh into becoming his and his friends’ sex slave. Now that the game is over, this series explores the further humiliation and abuse of Kayleigh as she becomes introduced to her new life.

DISCLAIMER #1: All sexual acts in this story occur between adults over the age of 18. In some chapters, Kayleigh is forced to role act that she is underage, however she is 18 years old.

DISCLAIMER #2: Themes of this story revolve largely around humiliation, sex slavery, and voyeurism. If you are not interested in these themes, please do not read. Of course, in real life much of what is portrayed in this story is despicable, and should not be tolerated under any circumstance. Hence, why this is a story of fantasy, and should not be taken seriously.

DISCLAIMER #3: While themes of the story certainly can be dark, I do try to keep things light with a certain “comic book” style. Again keep in mind that this is a work of fantasy and not everything will be fully realistic.

Enjoy! Please leave comments on what you want to see next as much of the following chapter is a work in progress. Cheers

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Part 4:

I had just finished cumming in my sister’s pussy from behind. It was amazing how tight and warm it felt no matter how many times I had fucked her. Vlad had fucked her asshole just a moment before. He was fast asleep. Kayleigh was tucked in tightly in between our bodies. I brought her in towards me and stroked my hand down the small of her back and gently squeezed her luscious ass.

Finally, the last night of our “predicament” had come. My parents were coming home tomorrow, and would be at Mr. Dudley’s house in the morning. I knew that I would never have the chance to sleep with my sexy young Sis again after tonight. I didn’t really care about Johnny’s rules or what the viewers wanted to see, I just wanted to soak in my sister’s nude body for as long as I could before our lives went back to normal tomorrow.

Over the past week, Johnny, Vlad and Mr. Dudley took me aside at one time or another. They all tried convincing me in their own way that we couldn’t let Kayleigh free. That with the amount of material we had of Kayleigh recorded, we could keep blackmailing her forever. Johnny showed me his calculation of how much we were earning off of Kayleigh’s webpage. He tried convincing me that if we kept her under this predicament that I would never have to work again! After I didn’t budge, he even tried cutting me a larger margin, saying that he would split the profit with me 50/50.

Although their pleas were tempting, and I would have liked nothing better than to keep Kayleigh as our personal sex slave for the rest of our lives, I simply couldn’t. Kayleigh had more than paid back her so called “debt” to Vlad and I for being such a bitch to us over high school. On top of that, Mr. Dudley and Johnny, as well as countless others had gotten a free ride (literally) at her expense.

After all, as sexy as she was, she was my sister. As much as my dick didn’t want it to, I knew that this situation had to come to an end and we had to let Kayleigh get back to her perfect life. After all, she had been the perfect sex slave. She performed all of her tasks on schedule and without question. She let us abuse her body and demean her in every way imaginable. She performed every depraved act without question. So after I let the guys know that I was going to stand by my convictions and free Kayleigh at the end of the week, Johnny tried to make the most of it financially.

He made it known on the site at the beginning of the week that we only had 4 days left with Kayleigh as our sex slave. He put a huge countdown timer on his site, and put Kayleigh’s channel on essentially full screen on the site in an attempt to direct all traffic to her channel. He wanted to drive up the bidding war on the “tasks” that viewers wanted Kayleigh to do in the few days possible.

He also let them know that on the last night, her brother (me) and Vlad would have exclusive rights of Kayleigh and wanted to be left alone with her. This was my idea, Vlad had been my main man all along, and I never would’ve had the balls to get my sister to go this far if it wasn’t for him. I wanted to finish the ordeal with him as well.

Johnny’s plan worked perfectly. After an initial stage of panic among the viewers that the object of their ultimate fantasy was going to disappear, next came a stage of mania. It seemed that the men were emptying their bank accounts to make their fantasies come true. Johnny, Vlad, Mr. Dudley and I read through the ideas in absolute amusement before picking fantasies that were both hot to us and well paying. We soon put Kayleigh to work.

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Fantasy #1

The first day’s winner had a personal vendetta he wanted Kayleigh to help him take care of. He was a bitter young man. We’ll call him Tyler. The nerdy type that barely saw the light of day and instead preferred to stay on his PC all day on various internet forums and of course, Johnny’s voyeur site where he feverishly followed each of Kayleigh’s exploits. He had never seen a girl so sexy, and so obedient.

The only one that came close to as sexy as Kayleigh was was the one that had been the object of his desires for his entire adolescent life.. His mom. You see, while he was a grown man, in his 20’s. He still lived in his parent’s basement. This allowed him to save up all of his meager income from working at a video game store to allow him to pay for Kayleigh’s services.

His mom was in her early 40’s. Despite her age, she was a beautiful woman. She had B cup breasts, a trim waist with a bit of love handles, and a huge 40-inch ass that he wished he could dive into face first. On top of this all, she was an angel of a woman. She loved him with all of her heart, giving him hugs and kisses every day. She was adamant that ‘her baby’ could live at home for as long as she wanted. She was a stay at home mom who, despite her wholesome heart, was completely naïve with the IQ of a dodo-bird. And you see, despite her undying love for her son, Tyler had twisted desires.

Tyler had long set up spy cameras in his parent’s bedroom, and his mom’s bathroom. He jacked off daily to her naked showers, and even to her having sex with his dad. He’d imagine that he was the one fucking her mercilessly. Soon, simply watching his naked mom didn’t interest him anymore, he knew he had to have her. His mind was corrupted by stories on the dark web, including my own with my sister. He was convinced that he was going to make his hot mom his sex slave. She was definitely stupid and naïve enough to fall into his trap.

There was only one problem, his asshole of a dad. For as long as he could remember, his dad, with his ‘jock’ like persona would make fun of him. Of how he was a virgin, of how he lived at home, of how he spent all of his time on the internet. Despite being an asshole, his dad was smart. He was the breadwinner of the family, and he kept a close eye on his wife. He knew she was hot, and while she would never be the type to cheat, he wasn’t the trusting type. Tyler knew that he couldn’t try anything with his mom as long as his dad was in the picture. This is where Kayleigh came in.

We almost laughed reading his request. This guy was crazy! But so crazy we thought that it just might work.

Tyler arranged so that his dad was home alone on a Friday night. His mom was having a girl’s night at her friend’s house. He was in the basement as usual, awaiting to see how his plan unfolded. He knew that his dad would barely even notice his presence, as his basement was well secluded.

Just then, the doorbell rang. His dad went to answer the door, his jaw almost fell open. Kayleigh, dressed in a thin cotton ‘V-neck’ and tight “TNA” pink yoga pants was at the door. She explained that she was a high-school student looking to earn some extra cash to save up for driving lessons. She was going door-to-door to do some maid work in hopes of earning some money.

The man gulped, paused, and eventually invited her in without even asking her how much she charged. He couldn’t help but admire the young teen’s body. She clearly wasn’t wearing a bra. Her nipples were visible through her thin white shirt. He had never seen a rack like this in his life. Her waist was impossibly skinny, and tits were massive. Despite their DD cup size, they stood perfectly pert in position, almost like they were being pulled up by invisible string. While he loved his wife, he dreamed that she would have breasts like this. Kayleigh’s V neck plunged down revealing a generous amount of her cleavage.

After they agreed on a meager 10 bucks for 2 hours of cleaning, Kayleigh got to work. She walked to the sink. The man watched in awe as her ass jiggled in her tight yoga pants with each step. She started to wash the dishes. The man sat at his dining table, pretending to read the paper while he stole looks at this young vixen.

Kayleigh soon ‘accidentally’ sprayed herself with a jet of water. She turned to him, with her white shirt now completely see-through. His jaw dropped at the site of her breasts as thin shirt clung to them completely.

“Sorry sir, I made a bit of a mess.” She giggled

“Oh it’s ok.” He said, before summoning up some courage. “You know though, feel free to take your shirt off, I don’t mind.”

Kayleigh giggled “OK, but just so you know, that’ll cost you $5 extra.”

WHAT? Did he hear this girl right. She had a payment plan to clean houses with her top off.

“Umm, excuse me? You mean other men have been paying you to clean their house topless?”

“Yeah, almost everyone. I’ve been making a lot of money!” she beamed

OK well, if everyone was doing it, it couldn’t be some government trap like you see on the shows, he thought to himself.

He reached into his wallet and handed her a 5.

She took it from him and swiftly took her shirt off, revealing her DD cup tits to him in all of their glory. He was in awe. He had never seen a pair of tits like this, even in the movies. Now, he was a faithful man, but he reasoned with himself that it wasn’t like he was gonna fuck this young girl. He was just having some fun.

She smiled as she started cleaning the dining room table. Her big bare boobs swaying with each movement. He made no attempts in hiding where he was looking.

She piped up.

“You know, you can feel them for another $5”

Soon in exchanged for another small bill, he had his hands on the sexiest tits he had ever seen. He even started licking them. Kayleigh let him have his fun. He had her young tits in his mouth. His hands instinctively made their way to her ass and squeezed. He was rock hard and was throwing caution to the wind. He started to peel her pants down when she stopped him.

“Sir just so you know, The pants are $5 and the panties are $7. But if you want both off I’ll give you a deal for $10.” She winked

The man almost laughed. She could’ve charged thousands and he would’ve paid for this babe. He put another $10 on the table. She instantly stepped out of her pants and panties, standing before him completely nude.

She knew her mission. “Sir, I think I should clean your bedroom next.”

The man gulped. Was she really going to do this. Was he going to cheat on his wife with a young schoolgirl. Almost as if she sensed his inner struggle, Kayleigh brought her body close to his, pressing her breasts into his chest. She pulled both of his hands to her bare ass, he instinctively squeezed.

This pushed him over the edge. He picked the girl up and started walking up the stairs to his bedroom.

“Sir so it’s $5 for a blowjob, $10 for sex, $10 for anal sex. Or we can do all three for $20.”

She had $20 thrown at her before she could even get the word out.

“Just so you know sir, I’m sixteen years old.” She said loudly in an innocent voice “but I won’t tell if you don’t” she whispered

This was enough for him. He went to town on the girl, breaking his wedding vows. He enjoyed every single hole the girl had to offer for hours.

Finally, around 9pm her phone went off. She answered, it was Mr. Dudley telling her they had more than enough footage.

“Yes Daddy, I’m just at Steph’s house. I’ll be home soon I know 9:30 is my curfew.”

The man had instant regret over his deeds. Not only did he cheat on his lovely wife, but he did so with a young girl. These last words that she said hammered it home.

She got up nude before him and said loudly “So sir, that’ll be $5 for showing you my boobs, another $5 for letting you touch them, $10 for showing you my ass and pussy, and $20 for letting you put your penis in my pussy, mouth and ass.. so $30 altogether?” she feigned ignorance

The man felt a knot in his stomach. He handed her $500 “Buy whatever driver lessons you want. Just promise you won’t tell anyone ok.”

“It’s our secret sir.” She pretended to zip her lips and skipped downstairs.

Meanwhile, Tyler was overjoyed. He had more than enough material to blackmail his dad. He was going act anonymously to get him to leave his mom and leave the house, with the tapes as blackmail. If he didn’t comply, he would simply send the tapes to the police and have him in jail. He knew that his mom would be devastated, and that he would start by comforting her. He knew that with his dad out of the way, and his mom putting her trust fully in him, that she would be easy to manipulate into becoming his sex slave.

He heard his basement door open. A naked Kayleigh walked in and sat on his lap. Kayleigh proceeded to walk the poor boy through having sex, and ultimately helped him lose his virginity. She let him have a go a couple more times before getting dressed and getting back into our car. We had decided to throw this fucking in for free, for exclusive live access to his developments with his mom down the road. Johnny felt that it would be a ‘hit series’ on his website.

To Be Continued in Part 5

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