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Training my Sister Kayleigh Part 2

2022-10-20 00:51:05

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. There were tons of accompanying footage of hours of group sex with her, starting with the feigned group of dare that we played to kick it all off.

Next was the text and accompanying full video clips and pictures of the aftermath of each one of the boys “fantasy” one-on-one sessions with Kayleigh. Next we detailed how we dressed up Kayleigh to be Vlad’s father’s “surprise date”. Accompanying the night were clips of his gradual advances, and the full video of when Mr. Dudley fucked her for the first time, and then when we had group sex with her later that night.

The story then accelerated to Mr. Dudley finding out from us what the truth was, and then authoritatively laying down the ground rules for our developing sex slave.

Next I detailed our exploits at Johnny’s, and the rationale of each one of his “treatments”. There were video clips of her getting a dose of the “RelaXXXall”, an injection of the “Sex Slave Cocktail” in her butt cheek, getting her official slut collar, and getting her first dose of “Slut Candy”.

Next were the high quality video clips of her getting fucked like the whore she was by the four of us, all while being leashed to a pole in the store like a dog. Since this was her first time on the “Slut Candy”, a synthetic MDMA analogue which made sexual stimulation unbearably pleasurable for her, this was the first time that Kayleigh squirted with her orgasms. This made for amazing video clips.

The story ended with a picture of her collapsed on the floor of Johnny’s store, lying in a puddle of her own cum and sweat. Her face and breasts were covered with dry jizz stains, her torso and face was flushed and drenched in sweat. She had a thick metal studded black leather collar strapped tight around her neck, attached to a heave linked metal chain. Best of all was that although her eyes were closed, she had this faint smile on her face, looking like she was in a happy dream like state.

The caption under the picture read

“So there it is boys and girls. That’s how this wholesome teen with everything in the world going for her became the cum slut that you see before you. Click here to follow her every move live, interact with her and her masters, and even get the chance to have your this sexy teen slave act out your deepest sexual fantasy!”

The story read like a short novel. There were thousands of pictures and videos. The four of us literally worked day and night to get the site operational within a couple of days. Reading through it though, it was well worth it. It was a masterpiece.

Anyone that read through the whole thing would surely give up a small fortune for the opportunity that we were offering.

Once the user clicked on the next link. He would be presented with several payment options.

1. For a limited one camera view of “Kayleigh’s room.” Where she slept, ate, and mostly where we fucked her, the user would pay the lowest fee.

2. For a full camera view of her room, where the user could toggle between different cameras depending on what they wanted to see, the price would be a little bit higher.

3. For the full access view of the entire house (aside from a room and a bathroom we had set aside for ourselves), and the opportunity to follow Kayleigh wherever she went through wearable camera’s and microphones, the users would have to pay a premium price

Number 3 was by far the most popular. Like I said, anyone that made it this far in the story was in too deep to turn back. They viewed this as a voyeur opportunity of a lifetime. Johnny informed us yesterday that we had already almost made back the cost of the equipment and supplies. Almost all of his sites patrons had been drawn to the story and made it through. Most of them went on to buy a subion.

Johnny kept 60% of the proceeds and he gave Mr. Dudley and I the residual 40%. The money was nice, but it wasn’t the reason I was doing this. Sharing these exploits online, and having thousands of eyes stalking Kayleigh’s every move, getting their rocks off to her sexual exploits was unbelievably stimulating for me. I was practically living out my biggest voyeur fantasy.

There were pay as you go options for requests that our premium customers could make. This would be transmitted to us through a live chat. We always had the option of whether we would make Kayleigh do the act or not. But usually we liked to give the customer a good show.

Things had changed quite a bit since a week ago at Johnny’s shop. My sister Kayleigh had turned into our obedient sex slave sinking further into depravity with each passing day. I’m not sure if it was because she had mentally checked out, because of the effect of the medications she had gotten, or if she had simply begun to accept that this was her life, for now at least.

Another development was the effect that the ultra-addictive “Slut Candy” had on my sister. When she was on it, getting touched intimately was so intensely pleasurable for her. That sensation was 100 times more pleasurable than anything else she had experienced in her life prior. The pill would last 3-4 hours, and all Kayleigh wanted to do during this time was fuck. She would quite frankly turn ravenous for any kind of sexual contact, and would orgasm countless times. It was honestly incredibly sexy to see her like this.

Vlad asked Johnny once if we should try it. He urged us not to, he said that the chemical properties were so addictive that we could become dependent on it after one use, and we would essentially be bound to trying to get that high again. I’m thinking that this had already happened to my sister.

We used it as a treat for her. To earn a pill of “Slut Candy” at the end of the day, Kayleigh had to do all of her tasks perfectly. If she missed one blowjob, didn’t fuck us with the enthusiasm we wanted, or even failed to keep the house clean or cook, she wouldn’t get any “Slut Candy”. In addition to this, to promote customer satisfaction, any request that we picked for her to do, Kayleigh would have to do impeccably.

Using this as a treat to positively condition her was Johnny’s idea. It worked like a charm. The first night that we withheld the drug from her she looked visibly distraught. I’m sure that if she was allowed to she would have screamed at us for it. The next day she fucked us so good to earn the drug at the end of the day. Since then she’s essentially been trying to outdo her sexual performance from the previous day. Johnny assured us that this was the best way to train our slut. Johnny gave us plenty of advice on how to best handle Kayleigh, as he had much more experience in matters like this.

He had her sleep in the utility room in Mr. Dudley’s house. It was a room in between Vlad and Mr. Dudley’s room. She slept fully naked, of course. She slept on a thin mattress, she wasn’t allowed to have covers. There was a heavy link chain that wrapped around the cylindrical water heater and connected to her black leather doggie collar. The chain had about 5 feet of slack.

Personally I liked when Kayleigh was snuggled up in between Vlad and I, but Johnny insisted that the customers like the idea of the girl being chained up in a separate room like a dog. Also they didn’t want to look at two dudes all night, they were only here for Kayleigh after all. We would come and go to fuck her as we pleased though. Some people like midnight snacks, we were usually more in the mood for a midnight fuck of my sex slave sister.

There were several high definition motion detecting cameras directed at Kayleigh in her room. They tracked her every move. The users could toggle in between screens depending on what they wanted to see. There was studio quality lighting and backdrop that had been set up in the small room, as this is where Kayleigh spent the majority of her time.

Johnny told us how different people had different fetishes. Some wanted unspeakably dark things to be done to Kayleigh, others just wanted to watch her sleep. He said we would uncover these fetishes as the clients become more comfortable and interactive with us.

At 4:30 am every day Johnny would come into the house to get his time in with Kayleigh before he went to work. Not only did he want to make sure his number one asset was being taken care of, but he also wanted to mix in pleasure. He would let himself into her room and have his way with her. Sometimes I would be awake at the time and would watch on the live stream.

Like at the shop, he continued to be obsessed with her luscious ass. Hell, I couldn’t blame him. He would spend most of his foreplay around her asshole. Putting his fingers and eventually tongue into her anus. He would sometimes fuck her pussy, but mostly preferred anal, usually finishing deep inside her rectum.

When he was done he would tend to business. He would bring in a doggie bowl filled with her food for the day. The dog style wet food looked like a steaming pile of shit. It was dark brown, and had the texture of a thick smoothie, with clumps of solid pieces. It was a mixture of what Johnny thought was the optimum feed for a sex slave. It tasted terrible, but was high in protein with various kinds of ground up meat, fiber with ground up vegetables, and unsaturated fat with olive oils, chocolate greek yogurt and peanut butter. He was convinced that this calorie dense feed was the best formula to make sure a slut stays in peak physique.

In it he would mix in essential vitamins, her daily dose of “RelaXXXall” and a few crushed laxatives. He explained the latter part later.

He would instruct her to get on all fours and wait for her food like a pet. Of course she hated the food at first. But she soon realized this was all she was going to get, other than loads of cum of course. Even with the appetite suppressing effect of the metabolism booster he injected in her 7 days ago, the poor girl would still be starving by the time he put the bowl down.

“Slut do you want your food?”

“Yes Master Johnny.” She nodded hungrily

“What do you say then?” He cooed

“I’m a good slut Master Johnny, and I want my slut chow.”

“That’s a good girl.” He cooed

He put the bowl down in front of her. She hungrily started feasting.

Johnny knew that the clients loved seeing this part. This stunning babe literally looked like she was eating dog shit out of a doggie bowl, all while leashed like a pet. It was utterly demeaning. While Kayleigh couldn’t help but feel embarrassed, her stomach was gnawing away at her in hunger.

She wasn’t allowed to use her hands at all, she had to eat with her mouth alone. Invariably she would get the feed all over her nose and cheeks. The feed would drip down her chest onto her tits. The clients usually liked it more the messier she got during feeds.

She licked the bowl clean. Her face around her lips, nose and chest were all dirty.

She looked disappointed. Her diet had been pretty much cut in half since Johnny took over. To add to that the metabolism booster had increased her daily calorie burn. Kayleigh felt like she was wasting away. She almost always felt hungry.

Her waist, which was slender to begin with, now had almost no fat. Her rib outlines were becoming increasingly visible seemingly by the day. Despite this, the hormone injection that Johnny gave her ensured that her breasts swelled, almost like a pregnant woman’s would. They were almost up half a cup size despite her fat loss, and this was causing them to be exquisitely tender. Her body, sexy to begin with, was now resembling more and more like a pin-up model from every man’s wet dream.

Her ass, arguably her greatest asset, was also becoming rounder but yet even perkier. After her feeds, Johnny would lead her through an hour exercise session. Mostly focused on squats, jumping jacks, and planks. He wanted to make sure that her ass became even perkier, and that the rest of her physique stayed perfect.

Next is where the laxatives came into play. You see, Johnny explained to us that although some of his clients turn the camera off for this part, a large part of his clientele actually likes seeing the slave poop and pee! Some liked how it completely dehumanizes and humiliates the slave to be pooping in a corner like a dog wood. It gave the viewer so much power over the subject. Others just had a scat fetish, and liked watching poop come out of the anus, especially when it came out of an ass as perfect as Kayleigh’s. I won’t lie, I even became especially aroused by watching my sister poop. It was a testament to how utterly demeaned she was.

I’ll spare the details, but essentially Johnny gave her a laxative with her feed to ensure that she would have a big bowel movement before he leaves. She would poop in the corner of her room. There were cameras set up in all different positions so that the viewer could have whatever view they wanted. She would poop on a brown paper bag. When she was done, Johnny would roll up the paper bag and take it with him. He told us that people that were obsessed with Kayleigh and scat fetish actually pay big money to have Kayleigh’s big shits sent to them by courier! I could only imagine what they would do with it.

That part was a little bit weird if you ask me, but hey whatever people are into I guess.

Kayleigh was quite a dirty girl after she had eaten, exercised and pooped. So she needed to be washed.

Everything from here on out would be outside of Kayleigh’s room. So only the “premium clients” could watch.

She wasn’t allowed to wash herself either. Johnny would bring her outside in the back yard by her leash and have her kneel on the yard. He would get the hose out and start spraying her with cold water. She would shudder every time in shock. He pressure-washed the food off of her face and chest, before washing the sweat off of her body. Next she would present her ass to him so he could wash her ass cheeks clean. He would split her ass cheeks open to make sure the anus was clean.

Clients loved watching this part too, it was so humiliating for Kayleigh. Of course, there were cameras set up in the back yard to view this. He sprinkled some detergent on her which began to form soap suds with the water. He rubbed her down, always spending a particular amount of time on her large breasts and ass, making sure it was clean.

He blasted her with water again to get the soap suds off. Once she was clean, he dried her off. He would then put moisturizer on every inch of her skin, and then a layer of sunblock. He wanted to ensure her skin would stay looking young and taut, protected from the harmful effects of the sun. Finally, he sprayed her with perfume, giving her extra sprays around her asshole and pussy. He tugged at her leash and she followed him back inside. Once inside he took her leash off, leaving the collar on.

Depending on how much time he had before his shop opened he would either have sex with her again, or just give her ass a few gropes.

He decided he was running a bit late so he gave her prized ass a quick massage and a few smacks before leaving

“I’ll see you tomorrow slut, best behave today.”

“Yes Master Johnny.” She yelped obediently

It was around 7:30am usually when Johnny left. On most days the rest of us would still be asleep.

This was when Kayleigh’s work would start.

As Mr. Dudley instructed, she would wake all of us up with a pleasant surprise. As her brother, I got serviced first.

She scampered up the stairs and crept into Vlad and my room. She knew what I liked.

I had fallen asleep. I smelled the sweet smell of perfume. Perfume, and Kayleigh’s delicious asshole. I felt her luscious soft ass cheeks on my face. Her cheeks were so soft and smooth. Johnny’s skin care routine was really working. I moaned as I woke up. Having these beautiful ass cheeks sitting on my face was the best sight to wake up to.

Soon I felt her soft lips on my dick and the sounds of slurping. Kayleigh’s blowjobs were the most heavenly thing on earth. She really was a pro. She knew what I liked. She twerked her ass on my face while licking the tip of my dick with her tongue.

I heard the robotic whirring of the cameras following her move. It still felt weird to me that every time I was having sex with her it was being recorded. But I comforted myself knowing that my face was blurred out. And even then, no one was watching me, all eyes were on Kayleigh.

Kayleigh sensed I was close. She pressed her ass cheeks deep onto my face, causing my nose to abut her asshole. Simultaneously she deep throated my cock. I soon came deep inside her mouth, she swallowed every drop until my cock went limp. Part of me thought that maybe she was so hungry that she was actually eating our cum to fill up. The thought of that turned me on. She was literally a cum hungry slut.

“mm thanks Kayls.” I moaned as I drifted back to sleep.

“My pleasure Master Brother.”

She moved to Vlad. He preferred sex in the morning. Of course, the fat ass wanted sex only if it involved no effort from him.

She sucked him off to get him hard. And then she got on top of him and rode him. She bent over to put her boobs in his mouth.

“mm” he moaned as he started to wake. Her big breasts were gently swaying in his face.

Vlad was always more of a boob man. He loved the effect that the estrogen/progesterone shot had on her tits. They looked engorged. They looked almost like a size DD now. Not that we would really know her bra size, since we never let Kayleigh cover them up with one!

He started suckling on her nipple like a baby as she rode him. She smothered his face with her breast meat. He started to moan more intensely. Kayleigh rhythmically rode him faster as she sensed he was close.

Quickly She got off and stuck her mouth over his cock in time to catch his load. She deep-throated his cock until it went limp, milking every last drop of cum that she could. Vlad started snoring instantly.

Kayleigh rolled her eyes before standing up and going to Mr. Dudley’s room.

Mr. Dudley had his own personal morning ritual. He wanted service from every single hole, no matter how long it took. Kayleigh would bring him a Viagra, and feed it to him while he’s sleeping.

She would start with a straight forward blow job. His hands reached down to her soft tits and squeezed. The closer he came to coming, the harder his grip on her tits would become. Often he would pinch her nipples. This would normally cause her to squeal in pain. But ever since the injection her tits were so sore that this was excruciating. Of course she couldn’t tell him to stop.

She sucked him off fast and thankfully got him to cum, causing him to release his death grip on her tits. She swallowed the cum down.

Her job with Mr. Dudley was only part way done at this point. She knew that she had to keep sucking him until he got hard again.

She spent 10 minutes sucking his limp dick before it started to show signs of life. After a few more minutes it was erect again. She started riding the dick reverse cowgirl style.

She knew that Mr. Dudley liked watching her ass shake as she rode him. After seemingly 30 minutes of consecutive riding, she felt his dick start to twitch.

Again she got off and swiftly caught the load in her mouth. There wasn’t as much jizz this time, but still half a mouthful.

She knew what she had to do next. She started sucking away again. Her jaw would start to become sore at this point. After making him cum twice, she needed to suck him off in various ways for about half an hour before he became hard again, in part due to the Viagra.

This time she knew that he wanted her asshole. No matter how many times he had fucked her up the ass, she could never get used to it. His dick was so thick and long, it hurt so much.

Gingerly she sat on his cock, trying to allow for her sphincter to relax. She gently was making her way down before Mr. Dudley unexpectedly made a powerful thrust upward, sliding his entire dick into her anus. She screamed in pain “Owww”

Mr. Dudley roared in laughter.

I looked down at the chat. Some of the guys hated the way he treated her, many loved it. The comments were filled with “HAHA Take that slut!” or “You show her pal!” with the occasional “What an asshole.” or “You should be my slave Kayleigh I’d never treat you like that.”

Kayleigh found her poise and started to move up and down his thick cock. After a while the pain seemed to abate. It never went away completely, but it got a bit easier to tolerate. After about 15 minutes of riding him she knew it was time. She took his load in her mouth for the third time, like she does every morning.

Kayleigh got up without saying a word, and as per Mr. Dudley’s agreement, started to make breakfast while us guys got ready to start the day.

I looked down, one of the comments made me laugh.

“What a life. The sluts given out Five blowjobs, 2 anal fuckings, 2 vaginal fuckings and a workout all before the rest of these slobs have even gotten out of bed, that’s one industrious whore!”

The comment was ‘liked’ several times over.

Kayleigh had made us a king’s breakfast. She had made eggs, hashbrowns and sausage with pancakes. We hungrily started to eat.

Kayleigh wasn’t allowed to have any of course, her AM meal was all she got. We put water in her doggie bowl and that was about all she got. She went upstairs and started lapping up the water like a dog, while we ate our breakfast.

“Don’t tell her this but this shit actually tastes pretty good.” Mr. Dudley laughed

“Amen pops.” Vlad chimed

Now that we had fucked and eaten like kings, came the next part of our day.

We scrolled through the ‘suggestions’ on the live stream. Each premium member could suggest one request a day, and would put a price on it. Vlad, Mr. Dudley and I would vote on the one that we thought would be a good one.

Our eyes lit up as we looked at the screen and then at each other.

“That seems like a fun idea.” I said.