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.
One by one the men came to “Grandpa” and essentially agreed to the pact.
“I don’t know if my granddaughter is quite as ‘open’ as yours though pal” most of them said something to the effect of.
Grandpa laughed saying it was OK. They would do whatever it took including alcohol, relaxants, drugs, to get the girls to do what they wanted. The key thing was that everyone needed to be on the same page. Some of the poor old men looked uneasy, but as a product of the Viagra and aphrodisiacs they had consumed, and the sexy nymph prancing in front of them practically in the nude, they knew that they couldn’t say no. One by one all of them consented to essentially sacrifice their granddaughters to have a night with this unbelievably hot babe.
Grandpa gave devilish grin before ‘accidentally’ spilling more wine on Kayleigh’s bra. Wine dripped down her sleek stomach and soaked through her white thong.
“Kayls-bear, sorry dear. You better take those underwear off and let me throw them in the wash.”
Kayleigh gave a sly smirk before looking around.
“Jeez gramps are you sure? All of your friends will see me naked.”
“Oh I’m sure dear, and don’t mind them they’re just old men after all.”
You could see where the story went after this moment..
Kayleigh stripped down to the nude, and feigned to continue on with her play date with her grandpa. It wasn’t long before the men had essentially gathered around her. She innocently gave each man a few hugs and let them feel her tits and ass. Obviously there was no going back. The scene soon degenerated into the ten men taking their old but impressively hard cocks out and Kayleigh giving them all blowjobs like a professional whore. The night developed into a ten man, one babe gangbang. The senile old men fucked the young girl for hours.
Finally, when they could fuck no more, Grandpa took Kayleigh to his room where she showered herself clean. From there she made her way up to Tom’s room where she gave him the fucking of a life time. We threw in that fucking for free. After all, customer satisfaction is everything in this business.
Meanwhile the seniors were downstairs, still not quite believing what had just happened. The whole experience had put away all doubt as to what needed to happen next. They were looking pictures of one of the member’s young granddaughter, Melissa, a cute slim blonde with a banging body. Their dicks started to harden as they planned out next week’s “Gentlemen’s Club.”
…
Fantasy #3
The final day’s winner was inspired by Kayleigh’s “rape” scene at the hands of the homeless vagrants. He fantasized about young hot babes like Kayleigh forced to have sex with dirty homeless men. Of course, he never got to see it. Furthermore, he loved the idea of the young babe being essentially a fuck toy, simply to be used for sex. He really was the perfect viewer for our web page. His plan made all of our dick’s twinge.
He set up an interesting social experiment. His theory in life was that sexual urges, if strong enough, will over power all sense of morality in life. He wanted to prove this. In the middle of the night before the crack of dawn, we drove Kayleigh down to the seedy part of town under a bridge where we knew a bunch of homeless men resided. While they were sleeping, we tied Kayleigh up to a pillar under the bridge. Of course, she was completely nude. She was handcuffed and gagged. Her handcuffs were attached to a chain which was tied around a pillar which supported the bridge.
As we drove a little distance away, and we set up cameras to film the scene. On cue, Kayleigh started to moan loudly through her gag. The sun was beginning to come up. The combination of the light and the sound of Kayleigh’s moans woke them up.
“Oh shit.” One of them said as he walked over to her. The old homeless man was shocked, but couldn’t help but admire the young teens naked body as she tried to squirm free.
Kayleigh moaned loudly as the man came to her. Soon a few other men joined. All a mixture of aroused, confused and concerned. They started to whisper to each other. This really was hobo central, and soon a small crowd had gathered. A man broke the silence and walked up to Kayleigh. He looked concerned. Interestingly, he didn’t cover her up with anything. He examined her naked body, before bending down. He put his hand on her smooth tummy, before sliding the gag off of her mouth.
Kayleigh screamed “Please sir, some girls who I thought were my friends just stole all of my stuff and tied me here like this.”
The man examined her with a quizzical look on his face “Hmm, which girls, and why? What were you doing with them?” The crowd started to advance further.
“They’re my new friends from school, or at least I thought.” She said as she started to cry “My parents agreed to let me sleep over at the one girls house. The four of us were walking to her house, and out of nowhere they stole my new Guess purse, new shoes and they beat me up. They took all of the new clothes I was wearing that I just got for my sixteenth birthday, and they tied me up here.”
The man’s hand started to creep up her tummy, until the backside of his hand touched the underside of her DD cup breast.
“So you’re parents think you’re at your friend’s house for the whole weekend?” he asked gently
“Yes sir, so if you let me go right now, I can call the cops and they can drive me back to my house and can go after those stealing bitched.”
The man all but ignored her.
“So no one knows that you’re hear other than those girls?” He started to grin
The men around her started to creep in closer. It was obvious that there looks of concern was starting to be overtaken completely by looks of lust. They realized that this was going to be the perfect crime.
“N-no I guess not.. what are you guys doing with my breasts?” she said as she felt his hand start to squeeze her left tit. Another foreign hand reached groped her other breast. Another stroked her smoother stomach while another started rubbing her teen pussy.
“No-No Please don’t! What are you doing!” she screamed. The man put her gag back on, reducing her cries to muffles.
Again, you know what came next. The scene soon deteriorated into a gangbang. Kayleigh’s ass and pussy were used over and over again. Soon her gag was released and she was forced to service countless men with all three holes. Just when it seemed like the first wave of vagrants couldn’t go any longer another wave would come and fill her holes up with cum.
After countless hours the group of men seemed to tire out and dozed off at one point or another. When Kayleigh saw that many of the men had taken a break and momentarily left or had dozed off. And the only men still awake were weak, feeble or drugged out. She knew that this was her chance to escape. She took off the handcuffs, which were unlocked the entire time, and made a run for it to our car 30 yards away. By the time the vagrants that were robust enough to catch her had realized that she had left, we had already started to drive off.
I guess our viewer was right; men are certainly capable of thinking with their hearts, as long as their dicks aren’t hard.
…
As I dozed off to sleep thinking about these memories, I brought Kayleigh again close into my body, her breasts were pressing against my chest. I waved my hands through her hair. I knew that there were only a few hours that I could have my sister’s smooth sexy naked body close to mine like this.
As I fell asleep, I heard the front door open and some footsteps come in. It sounded like multiple people. I heard Mr. Dudley’s loud laugh, and a voice that sounded like Johnny’s. I figured that they must be having their own fun in some way, as I told them that I wanted this night alone with Kayleigh. I dozed off to sleep.
The next day I started to pack my stuff as I knew my Mom would be coming to pick us up soon. It turned out that my Dad was going to spend some extended time with my grandma, who was ill. But my Mom decided that she needed to come home to look after us. After all, they didn’t want us to be too much of a bother to Mr. Dudley.
Mr. Dudley and Vlad were getting some last minute fun with Kayleigh in. I just told them that they had to make sure that she was clean, presentable and of course fully clothed by the time my Mom came. My Mom gave me a text saying that she was about 30 minutes away. I screamed out to the guys that they needed to get Kayleigh’s ass down here. Within a couple minutes, surprisingly, Kayleigh came downstairs.
She looked almost as though nothing had ever happened. She had a pink preppy polo on. Her bust was visible, but after all she always had big boobs. It wasn’t unheard of for a teen girl’s breasts to increase a cup size, I’m sure my mom wouldn’t notice. Sure her ass had undergone a bit of a butt lift and yet still managed to have a bit more of a jiggle to it thanks to the combination of hormonal injections and Johnny’s rigorous exercise program. And sure her thin waist had become even thinner. Maybe Kayleigh could just tell my Mom that she had been working out really hard. I’m sure she would buy that.
Overall though, Kayleigh looked fine. Looking at her, who would’ve guessed that she had been our personal sex slave for the past two weeks. That she had been subjected to constant humiliation and demeaning to the level of a house pet. She looked like the golden teen girl that was ready to go back to her life and have the world be her oyster. She almost had that look of arrogance start to return. As if all she needed was to have her slave collar off, be fully clothed in her expensive garments, and be mentally preparing to go home.
Just then the doorbell rang. I thought my mom had come early. I opened the door, I was greeted to the hideous visage of Johnny.
“Hey my boy, just wanted to say bye to the girl here.” He walked to Kayleigh. He didn’t give her a hug, he didn’t grope her. He just stuck his hand out.
Reluctantly, Kayleigh shook it.
“Thank you for your services, dear.” Just as he was about to turn away he looked back at her though “Just so you know though, the experience doesn’t have to end here.” He said with a hint of a grin starting to form.
I was expecting Kayleigh to start laughing, or even slap him for his audacity. I looked on quizzically though. She shockingly said nothing. She had a bit of a confused look on her face.
“BOYS. Get up here.”
I heard footsteps coming up from the basement. The door opened, and to my shock, the three black homeless men walked into the living room. They were completely naked. Their huge dicks were out and erect. They were practically pulsating.
Kayleigh looked down at their pulsating dicks and her eyes widened.
I quickly shut the door, this was the last thing I wanted my Mom walking in on!
I turned and looked at the scene behind me. Vlad and Mr. Dudley were now beside Johnny, smiling. It’s like they were all in on a plan behind my back.
Johnny went on to explain.
“You’re brother has freed you Kayleigh. It’s your choice now. You can go back to your normal life, it’s as easy as turning around, walking outside the door and waiting for your Mom to come pick you up and take you home.” He said as he pointed to the door
“OR. Choose to stay, and embrace your life as a sex slave forever. Embrace that after your experiences here you will NEVER feel the same rush ever again. You will NEVER truly be sexually satisfied after the highs you felt here. Embrace that there is no going back”
I couldn’t believe it. I expected Kayleigh to make a run for the door, leaving this madness behind. Instead she was breathing heavily, as if rooted in a deep internal struggle. She looked at Johnny, then me, then at the black pulsating cocks in front of her.
“Embrace that you are our sex slave for life. As a celebration, I have given these three gentlemen extra strength Viagra, and enough aphrodisiac to last a day.”
He pulled a bottle out of his trench coat “And for you girl, this shipment of ‘Slut Candy XR’ just came in. Twice the intensity, lasting for a full 24 hours.” He shook the pill bottle while grinning.
Kayleigh looked at me, before gulping, almost as if saying goodbye. She knew what she had to do, she knew that there was no going back to normal life now.
She peeled off her pink polo. And swiftly took off her white bra. She stepped out of her jeans, and tossed aside her pink thong. She got onto her knees, fully nude.
“Good slut.” Johnny said as he tied the thick black leather collar around her neck. “Now beg for you treat.”
“Please Master Johnny, I’ve been a good slut. Please give me my ‘Slut Candy.’”
“Yes you have.” He smiled as he threw the pill on the ground in front of her. She gobbled it up
He tugged on her leash and led her upstairs, with her crawling on her hands and knees.
“Let’s get you to your cage slut, wouldn’t want your Mother hearing the sounds of her only daughter moaning like a whore.” He laughed out loud.
The black men and Mr. Dudley followed her upstairs.
Vlad turned to me “Dude this is awesome! I can’t believe she’s gonna be our slave forever now.”
I replied confused “I guess so. And hey if my sister is happy living this way, that’s all I can ask for right. Go ahead and get your ass up there bud, enjoy.”
“Thanks man! As soon as your mom leaves get your ass back here. It’s gonna be weird doing this without you.”
“I’ll try my best bud.” I smiled
Vlad quickly ran upstairs.
I checked the stream on my mobile phone. It was like it was a national holiday the way the voyeurs on the chat were celebrating.
“OMG I was so nervous.”
“Johnny you bastard I knew you’d come through.”
“They really had me going! But once a slave, always a slave!”
There were endless comments to that effect. I walked outside the door and on to the side walk. I knew that the slut candy would start to kick in soon, and that Kayleigh would start moaning loudly any second. I wanted my Mom to be as far away from the house as possible when the action started.
Soon I saw a familiar white BMW roll up. My Mom got out of the car and greeted me with a smile. Her blonde hair waving in the wind. It was hot Summer day, and my Mom was dressed accordingly. She had light breezy pink Summer dress on, which was sleeveless over one shoulder. I could tell she had developed a bit of a sun kissed tan.
I gave her a big hug. I got a bit of a jolt to my loins as her large breasts pressed against my chest. She obviously wasn’t wearing a bra.
“I missed you so much dear.” She cooed
I hugged her closely. I instinctively grabbed her by her narrow waist and brought her in. My hand slid to rest on her generous waist. I had the undeniable urge to grab her meaty ass.
‘What was I thinking.’ I thought to myself ‘Damn, this is my mom. These last two weeks had really hypersexualized me.’ I let go before I went too far.
My Mom bent over to pick up my bag. I couldn’t help notice her generous cleavage as her tits were practically hanging freely. The transitioned tan line between her sun kissed shoulder and her pale white tits became evident.
I forced myself to look away ‘Fuck dude you can’t be serious’ I angrily thought to myself. I watched her open the trunk, her dress rode up exposing her delicious thighs.
“Ugh this trunk is a mess, hold on babe I have to clean this up.” She said as she bent over at her waist and started moving some equipment around the trunk. I reluctantly positioned myself behind her.
I moaned in weakness as I saw the hem of her frilly dress slid up her backside, giving me a peak at the bottoms of her deliciously meaty ass cheeks.
“Fuck.” I whispered as I saw a small white thong sink desperately into her ass cheeks.
The size of her ass cheeks made Kayleigh’s look modest. I had the overwhelming sensation to lift her dress up, get on my knees and put my face in her ass cheeks right now.
I slapped myself in the face before turning around. I felt like I needed to take a walk and clear my head.
“All done dear come on in, let go home.” She said as she got up and walked to the door “Where’s Kayls by the way?”
“Oh Mom didn’t you know, she has that Volleyball camp this month, she’s away.” I impressed myself with my ability to think on the spot. I prayed hoping she’d buy it.
She flashed me a sexy- I mean motherly smile
“Oh yeah, silly me, guess it’s just gonna be you and me kiddo.” She said before climbing into the car.
Relieved, I took a seat beside her. I quickly checked my phone.
The live stream was incredibly active. Many were still buzzing about Kayleigh’s decision. Some were busy ‘fapping’ to the scene I imagine was starting upstairs. But most were saying something along the lines of.
“Uhh WHO is that and when am I gonna get to see her naked”
“I didn’t know Kayleigh’s mom was Lindsey Pelas <3”
“Holy Fuck I see where Kayleigh gets get looks from.. and her ass”
“Bro you HAVE to fuck her.”
“I’ll give you everything in my bank account to see you turn your Mom into your sex slave” Said one man. This comment was ‘liked’ over and over and over until it rose to the top of the chat
“What are you looking at honey?” My Mom looked at me sweetly
I quickly turned my phone to lock “Oh nothing mom, just some friends.”
The combination of my Mom, and seeing the viewers’ reaction to my Mom was turning me on beyond belief. I looked at my Mom’s smooth golden legs and made my way up to her breasts and then her heavenly face.
I was rock hard at this point. Like Kayleigh, in that moment, I embraced who I had become. There was no going back to a normal life now. I suppressed my conscious and smiled before opening my mouth
“Mom, how about we play a game tonight?”
The End