Training my Sister Kayleigh Part 5

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

Part 5

I continued to grope my sister’s sexy ass as she slept. I smiled as I recalled the second winner of our sex fantasy extravaganza this week.

…

Fantasy #2

On the second night, the owner of a small retirement home was the lucky winner. We’ll call him Tom. You see, not only did Tom get into his business because it was extremely profitable, but it truly because this sick pervert had a fetish involving old people. His fantasy involved seeing old men having sex with young women. He loved watching “old/young” porn on porn sites, but soon enough watching videos wasn’t enough, he wanted to see the real thing. He had cameras installed in every room of his retirement home. He would often fantasize that when his patrons’ attractive grand-daughters came over, that he would be able to record them having sex with their decrepit grandfathers.

Of course, since the whole world wasn’t as twisted as he was, he never got to see this happen. So he came up with a way to enact his wildest fantasy, with our help of course. Tom wanted to see Kayleigh have sex with the seniors in his home, and then in turn enact a diabolical plan to keep his fantasies satisfied for years down the road.

We got Kayleigh to dress as a schoolgirl again, using a similar outfit to the “rape scene” with the vagrants the few days before. She looked fantastic. Her DD cup breasts were lifted up with a silk white push up bra into the perfect position, not that the young girl’s tits needed a lift. She had a plaid skirt on which wrapped tightly around her juicy ass. She had plenty of thigh showing. Like the day before, she had knee high white socks on.

Tom let one of the old pervs he was tight with in on the plan. He was to act as if Kayleigh was his granddaughter and was keeping him company, and they were going to hang out in the common waiting area. Kayleigh was to act like an innocent school girl.

Tom arranged it so that the 10 seniors who he knew had sexy granddaughters would all be invited to hang out in the common room with Kayleigh and her “grandpa”. The rest of the seniors were sent away on a bowling trip for the night.

Kayleigh arrived, and the minute she walked through the door, all eyes were on her. These were mostly innocent old men, but they couldn’t help but notice how sexy this young visitor was. They commented to “Grandpa” that they had no idea he had such a beautiful granddaughter. Grandpa beamed as the lecherous pervert pulled Kayleigh in as his granddaughter, giving her a tight hug and letting his hand make its way to her bum.

Just then Tom came through, greeted his seniors and gave them some ice cream for dessert. Little did they know that the ice cream was laced with both Viagra and an aphrodisiac (supplied by Johnny of course). He wanted these old men as horny as possible. Grandpa smiled as he quickly wolfed down the ice cream and gave Tom a wink.

Tom’s eyes lingered on Kayleigh. Even though he had seen every inch of her beautiful nude body in high definition online, she looked infinitely more stunning in person. He knew that after his plan was enacted, he was going to take this young slut to his room and fuck the shit out of her.

After the men ate their ice cream, Kayleigh went to work. She was all over “Grandpa.” Nothing obviously sexual, but she was definitely touchy with him. To add to that, she made sure to drop plenty of things so that she could bend over and show her thong clad ass to the old men around the room. She even unbuttoned her blouse down a couple buttons so that her cleavage was showing to every man that would care to look.

It wasn’t long before the men started whispering openly to each other about how sexy Kayleigh was. Grandpa went to work. He started approaching the men with a deal, of course all according to Tom’s plan. His offer was that he would coerce his “granddaughter” to be gang banged with each man in the room, but only if the men would do the same with their granddaughters down the line. They would make a gentlemen’s club with each one having to offer up his sexy granddaughter to join.

A few of the men took one look at Kayleigh, took another look at their now throbbing cocks, and obliged without another thought. Most of the men said they couldn’t. Grandpa knew what he had to do. He feigned spilling wine over Kayleigh’s blouse and skirt. Playing innocent, Kayleigh quickly took her blouse and skirt, off leaving herself in nothing but her silk white push-up bra and matching silk white thong. She continued to act non-chalant and playful as she hugged her “Grandpa” repeatedly. She went around to each of the men that hadn’t agreed to the deal and offered to fill up their drinks, and chatted with them playfully. She ended each conversation with a lingering hug, practically pressing her DD cup breasts into the seniors’ chests and encouraging their hands to touch her practically nude ass.