Training my Sister Kayleigh Part 2

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 2

It had been a week since we had visited Johnny’s Spy Store for the first time, and what a week it’s been. A lot had changed.

Johnny helped us install all of the high tech surveillance equipment in Mr. Dudley’s house. The deep web page that was dedicated to tracking our exploits with my sister Kayleigh was set up the following day, thanks to a lot of hard work from Johnny and I. This was my holy grail, I wanted to make sure this page was a masterpiece.

To describe an idea of the user experience of what we had created:

As the users loaded Johnny’s dark web site main page filled with all of the different categories of hidden cameras and voyeurism, there were banner like ad’s on each side of the main page with pictures of Kayleigh.

They were wholesome pictures, the one on the right was her yearbook picture. The one on the left was a picture of her in a dress at a school dance. She looked gorgeous of course, but wholesome.

After several seconds the pictures would change. One picture changed to one that was of her sucking a dick in front of her (mine) while having another (Vlad’s) in her hands. The other was one of her getting railed from behind by Mr. Dudley, with her cum stained face up close to the camera.

The caption on each picture read “Click here to see this hot teen get tricked into becoming a sex slave by her brother! Follow her every move! XXX”

No matter what link the user clicked on, these banners stayed on the web page. Johnny knew that this was going to be the centerpiece of his website, and he wanted to divert as much traffic to it as he could.

When the user clicked the link, the web page changed to one dedicated to our story. The main feature on this page was a slide show of pictures of Kayleigh. It started with the one of her in Johnny’s shop, chained on a leash, collapsed on the ground with jizz all over her face and tits. It cycled through automatically to pictures of her licking cum off of her tits, getting fucked up the ass, pussy and mouth at the same time at Johnny’s shop, licking cum off the floor at Mr. Dudley’s, and having an orgy at my house with my friends.

The faces of all people other than Kayleigh were blurred completely. Johnny had a face recognition feature on his software which by default blurred out all faces other than the girl he wanted to focus on, for obvious reasons.

As the user scrolled below the story started. It read

“Gather around boys and girls, here follows the real life story of how a brother turned his young sexy teen sister Kayleigh, the Straight-A student and high school cheerleader, into his personal sex slave.

Read the full illustrated story with 1000+ real pictures and video clips here!”



The user would click the link and then be prompted to pay up. Johnny took various cryptocurrencies as payment, as they were harder to trace then cash. The user would have to pay a significantly higher price to continue, compared to the other “stories” Johnny had on his website. Johnny was confident that the story was so appealing, and that Kayleigh was so sexy that the pervs that frequent his site would pay anything to continue.

After they paid, they would be redirected to the next page filled with the story.

This part was where I put in the most amount of work. I titled the story “Playing Dare with Sis” and broke it up into various four parts.

It started off the introduction of who Kayleigh was. I included pictures of her post puberty, playing volleyball, soccer, at high school dances, and cheerleader competitions, with friends. I painted her life as next to perfect, because it was. But I made sure to emphasize how much of a bitch she turned into in high school, and how she would bully her brother and his friends mercilessly. Even though the readers don’t know who I am, I wanted them to know that I had motive for what I’m putting my sister through, that I’m not completely evil.

I progressed the story to the plan that Vlad and I concocted on a whim just 10 days ago. I posted about how the game began, as just a silly game of dare, with $100 on the line. I even posted a silly video of her doing jumping jacks as a dare. Her tits still were tantalizingly bouncing up and down, but fully clothed.

The story progressed to the part where Vlad and I got her to strip to her underwear. She did so willingly of course, as it wasn’t full nudity and was allowed as per the rules. Next was the famous picture that started it all.

In full frame in the center of the text now was the picture of Kayleigh bent over on all fours, in her thin white bra and thong, soaking wet from the shower we made her take. As the user swiped through the picture sequence he would see how it progressed to Vlad and I posing to make it look like she was about to get double teamed by us.

From here the story progressed and Kayleigh completely lost control. Next came the part where we got her topless for the first time. This was accompanied by a picture, Kayleigh’s first picture with her big tits out. You could see the fear in her eyes, there was a tear rolling down her cheek.

Next was a video clip of Vlad taking off her thong with his mouth. Next were a set of pictures showing my fully naked sister for the first time, in all of her glory.

Then came full detail of our sexual exploits that night. First a full video of when she gave me a lap dance ending in a blow job. This was the first time that she gave her brother a blow job. The nude lap dance served to highlight her perfect body in action.

The picture sequence ended with a picture of her face and breasts covered in cum. Next I detailed how we forced her into having sex with us. It started with me of course, being the brother. There was an accompanying full video clip of me fucking her and jizzing again on her tits. I remember vividly the look of sadness in her eyes as we recorded her licking the jizz off her big tits. The scene essentially repeated itself moments later, this time with Vlad.

The story then accelerated through the events of the following day, involving group sex with all of my friend group who she bullied in high school.