Training my Sister Kayleigh Part 3

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

…

Mr. Dudley, Vlad and I were driving Kayleigh to the center of the seedy part of down around Johnny’s Spy Store. Kayleigh was seated in between Vlad and I in the back seat. My hand was stroking her thigh up to the hem of her charcoal schoolgirl skirt.

We dressed Kayleigh up as a school girl at the request of one of our online viewers. He had a rather interesting, and very high paying fantasy that he wanted Kayleigh to enact. He explained to us how he had a rape fetish. To make it even darker, he fantasized about watching a hot young school girl getting raped by vulgar homeless men. When he got introduced to Kayleigh and her story, he quickly realized that this hot young babe, and the predicament that we had her in would allow for his fantasy to be fulfilled.

We corresponded with him, after all, we were in the business of making voyeur fantasies come true. After collaborating with him, we came up with the plan. We dressed Kayleigh up as a young school girl. We had her tie her hair up in pigtails, and dressed her in a tight fitting white blouse and a plaid pattern charcoal skirt which ended several inches above her knees. She had on knee high white socks and black sneakers. We had taken off her slave collar just for this mission. We equipped her with a “Hello Kitty” backpack filled with a few light books.

One of us could’ve simply dressed up as a stranger and pretended to “rape” Kayleigh, but this didn’t seem good enough. This customer was paying a lot of money to see his ‘fantasy’ come true, so we wanted to treat him right. Also, we wanted to have a bit of fun ourselves.

We instructed Kayleigh to act especially innocent and bubbly, to reinforce her youth. She was to act lost on her way home from a school she had just started. We instructed her to walk up and down the alleys, we knew there were plenty of homeless vagrants in this part of town. We knew that sooner or later on of these vagrants would be too tempted to care about any legal ramifications, and would do the deed.

To record the deed for our loyal viewer, Johnny equipped Kayleigh with a Christian cross necklace that had a video and audio recorder. She also had a piece of silver clip-on belly button jewelry that had another video recorder. To add to that, we would trail her in our car and record the scene with a high quality video camera. We were close enough to Johnny’s shop that we could actually live stream the scene using his Wi-Fi. Johnny also came out to meet us. He had a rifle with him, just in case anyone decided to hurt Kayleigh too much. We had to protect our property, of course.

We let Kayleigh out of the car. I admired the swell of her tits, straining the buttons of the tight silk white blouse. She hesitated and she whimpered in fear. We had never asked her to do anything like this before.

“You better do a good acting job slut. No “Slut Candy” for you tonight unless the client is 100% satisfied.”

This threat gave her some resolve. She put on a brave face and ventured into an alley. I was salivating looking at her ass sway with each step she took.

I couldn’t lie, I was excited to see this as well. I was sure some homeless slob was going to have the time of his life raping my sexy sister.

“Holy shit I can’t believe this is happening, you guys are awesome!” The viewer exclaimed.

Kayleigh ran into an old man sitting beside a dumpster. She cheerily asked him for directions getting to a street a few blocks away, explaining that she had just moved here and wasn’t used to the town. The man looked her up and down, and had a quizzical look on his face. I imagine he had never seen a girl this sexy in this area ever. He looked like he was battling with himself for a split second, before forcing himself to look away from her and simply pointing her in the right direction.

Kayleigh skipped away and went down the next alley. A homeless woman practically grabbed her and interrogated her on what she was doing in a place like this. She scolded her and told her to leave and get home immediately. She warned that there were bad men around these parts. I chuckled as she also scolded her for wearing such a short school girl skirt. She sent Kayleigh on her way.

Then Kayleigh tried the alley on the other side of Johnny’s store. She skipped down the alley.

“Damnnn girl, you lost?” a man hollered at her.

He was a large black man, he walked over to her, imposing his large stature over her.

“Check this out boys.”

Just as he said that two other black men, one about 6’6”, the other was short but much fatter. They were in their 40’s, all had toques and tattered clothes and stained shirts. They had straggly beards. They were certainly homeless. The three of them made a circle around Kayleigh. They all were large men, and essentially towered over her.

“What can we do for you girl?” the tall one asked

‘”Mm I know what I wanna do to her.” The fat one said

We positioned ourselves across the street and zoomed the camera in. My heart was racing, I couldn’t imagine what Kayleigh was feeling like right now.

Kayleigh giggled “Hi guys. I’m a new student at the private school a few blocks away, I just moved into town and got lost on the way home.”

“Damn look at those titties.” One said, essentially not caring what Kayleigh had just said.