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.
The seeming leader of them replied "Well girl we can help you get home no problem, but you gotta help us out in exchange." "Haha ok that's only fair sir!" she giggled "What can I do for you." The tall on behind her took put his large hand on her ass cheek and squeezed. "Showing us the ass you got under this skirt would be a start." "What are you doing!" she said as she slapped his hand away and turned to him "I'm not doing that!" The leader reached from behind and put his hands on her tits.
"Ok then how about showing us these big white tits girl." She struggled to get away but he pulled her in closer. "No No please! I'm only in grade 10! I haven't shown anyone my boobies." The fat one came in front of her "Well there's a first time for everything hoe." He put his hands in the seam of her blouse and in one brutish pull he tore it open, popping all of the buttons.
"Daaaammnn." The said in unison as her bra incased tits bounced free. "I've never seen tits like this before, can't believe this girl's only in grade 10, fuck." Kayleigh was squirming to free herself but the man behind her was too powerful.
He had her restrained by her armpits, lifting her arms behind her head, thrusting her tits out even further. We had Kayleigh dress in a pushup black bra. Her already large tits looked amazing in this bra. "NNO NOO please no." Kayleigh bawled. "Please don't do this sirs." She started to cry like a school girl would. The men paid her no mind. The tall man in one brutish tore her bra open, causing her tits to bounce free.
"Holy fuck." He exclaimed as Kayleigh DD cup tits were bouncing everywhere as she was squirming feverishly against the man restraining her from behind. "I gotta suck on these big white titties." The tall man said as he took her tits and started shoving his face into them.
"mmm girl you're a blessing." He said before devouring her tit into his mouth while squeezing the other one. "Pleeasee stop" she bawled "That hurts." The man behind her put her down, but the tall man gripped her tight across the waist, again restraining her movement.
The leader of the men started groping her ass through her skirt. "Damn boys this white girls got an ass juicier them I've ever seen on a sister." His large brutish hand lifter her skirt up and put a hand on her bare ass cheek. In one swift move he took her G string in her hand and ripped it off.
"PLEASE no, not there. Let me go sir Ill give you anything." She cried "Nah you just gotta give me this phat white ass girl." The fat man stripped her skirt off and threw it to the side. She was now completely nude other than her knee high schoolgirl socks. "Fuck look at this bare ass." He said as he jiggled her cheek up and down with his hand. "I ain't ever seen an ass like this." The fat one said as he squeezed the other cheek. "I gotta get a taste." The leader moved aside and let his buddy get behind her.
He groped both cheeks before getting on his knees behind her. He was mesmerized by her luscious bouncing cheeks. The fat black man had never seen anything like Kayleigh's ass in his life. He was kneading each cheek like play-dough and started drooling uncontrollably. He brought his face up to her ass cheeks and sniffed "Ohh fukk this white girl's ass smells like flowers." He drooled "Then go to town bro!" The leader laughed The fat one didn't need to be told twice.
He buried his face into her juicy ass cheeks. He started licking the inside of her cheeks like a madman, slobbering drool down her thighs. Kayleigh screamed "No not there PLEASE!" "Scream all you want bitch, aint no one coming to save you here." The leader grinned "Your screaming only makes us wanna fuck you harder." It was a sight to behold.
The tall black man was still sucking away on each of her DD cup tits, while grabbing her tightly by the waist and lifting her up off her feet. She was struggling and squirming with all of her might, but to no avail. All the while she was lifted up so that her ass was face level with the fat man on his knees behind her whose tongue had found its way to her asshole. I looked to the live stream "Holy fuck this is so hot guys I think I'm gonna cum." Our client typed I typed back "You better get it back up soon bud they haven't even fucked her yet!" I had to agree with him, this was incredibly hot to watch.
I looked over at Vlad and Mr. Dudley, they were both rock hard while watching this scene. While his cronies were slobbering away at Kayleigh tits and ass, the leader reached into the dumpster beside where the scene was going on.
He brought out some frayed but thick rope from the dumpster. He then brought out a thin mattress. Apparently these guys were using this dumpster as their bedroom! He threw the mattress on the gravel alley. The mattress was tattered and torn. It had yellowish stains all over it. He tied the thick rope around a bar on the top of the dumpster and then closed it so the rope was dangling down and touching the ground.
He barked at his cronies to take their mouths off her and turn her with her back to him and yank her hands behind her back. The man took the rope and skillfully tied it tightly around her wrists, binding her hands uselessly behind her. She cried out again, practically bawling like a little girl. He pulled his trackpants down, he wasn't wearing any underwear.
The three of us all looked at each other in dismay. This man's dick was unlike anything we had ever seen. It was as thick as a coke can, and was at least 10 inches long. The girth of it made even Mr. Dudley's dick look modest. "N-N-O NO PLEASE NO SIR." Kayleigh bawled in horror.
"Shut up bitch you gon' take this dick." He turned her around and pushed her cheek against the cold steel of the dumpster while keeping the other hand around her hips.
She was bent over at a 45-degree angle with her cheek against the dumpster and her ass facing her molester.
He gave her ass a big smack and squeezed. "I might've let you go if you didn't have an ass like this." He said as he squeezed her cheek roughly "you know me and my boys can't resist this booty girl." Tears were running down her face freely.
After a few more seconds groping her ass he split her ass cheeks apart and brought his comically large member to her pussy. Just putting the tip in caused Kayleigh to gasp. "Oooh fuck this teenage pussy is so tight boys." Kayleigh cried out loud in pain as he further advanced his dick into her tight pussy. He gave her a sharp slap on her ass. "Haha it's only half way in girl." I couldn't help but snap several pictures.
The scene was incredible. Kayleigh was bent over with a big black cock in her pussy from behind, all while roped up by her hands to a dumpster. This caused her DD cup tits dangle down deliciously from her chest. The effect of gravity made them look enormous, especially in comparison to her impossibly thin waist. I envisioned this picture as being the thumbnail for this scene on the website. Kayleigh moaned excruciatingly as he fully advanced his hard dick into her.
As he started to thrust her large breasts swayed slowly back and forth. "Damn look at those titties rock." The fat one said "Oh fuck boys she feels so good." He said as his thrusting began to intensify "I've never fucked a pussy this tight. And her phat ass feels so good." The other two got their dicks out too. The tall one's was skinny but must've been almost 12 inches long! The fat one's was probably around 7 inches long but was as thick as a water bottle.
All the while Kayleigh was wailing away as the leading man was pounding away at her at full force now. She had never felt a dick like this, it was like her pussy was getting hit with a sledgehammer.
She couldn't believe how deep it was hitting. She felt like it was smashing her cervix with every blow, trying its best to blast through it. It was excruciating but at the same time was stimulating her the way she's never been before.
Unbelievably it felt like it was almost getting bigger inside of her! "OHH FUCKK here it comes bitch." He screamed His cock started to jerk inside of her, and unloaded a huge load of cum, filling her vagina up. "She's all yours boys." He said as he turned to his kronies "Noo NOOoo please no more I feel like my insides are torn!" she cried "hehe we're just getting started bitch." The tall one said. He took the place of the other man and inserted his long dick into her vagina. Impossibly she felt that this dick was slamming her cervix even harder.
She moaned loudly. The fat one stuck his dick in front of her and started slapping her pretty face with it. "Suck this white bitch." She did as she was told and put the fat black cock in her mouth.
Her lips could barely fit around the thick cock. She instinctively started to do what she did best and started sucking the cock like a pro. "Damn for a school girl you pretty dirty bitch." He laughed. His short stature allowed for him to easily reach under her and grab her big tits. He squeezed Kayleigh's still tender breasts causing her to moan in pain.
Soon Kayleigh felt his dick start to spasm in her mouth. He took her by the hair and took his dick out of her mouth and put it inches from her face. He started to moan before unloading seemingly cups of cum onto Kayleigh's pretty face.
"Damn I never jizzed on white bitch's face before." He laughed The leader reader told the tall man to stop fucking her for a moment.
He untied the knot at the dumpster, leaving Kayleigh handcuffed by the rope but momentarily free. She decided to try and make a run for it. She tried to bolt down the alley, but could barely make it a few feet before the leader grabbed her by the waist.
The brutish man carried her over his shoulder before throwing her onto the stained mattress on the street. "Nooo please let me go!" she begged "oh baby we are just getting started." He seethed The tall man lied down on the mattress. "Ride this tall dick bitch." He commanded. Kayleigh reluctantly climbed on top of him and moaned in pain as she felt the entirety of the cock inside of her.
She didn't have her hands to use so to have any leverage to fuck the cock she had to essentially collapse on to the tall man's chest. Her big tits squished against his chest.
The fat man got behind her and again started to become almost fixated with her ass as it jiggled while she rode him. It wasn't long before the site of Kayleigh's voluptuous ass cheeks got the man hard again. Meanwhile the leader felt like he needed his dick sucked. Kayleigh didn't have the leverage to try and raise herself to the level of his dick. So he grabbed for by her pigtails and pulled her up by the hair.
"OWWW" She screamed. As her mouth was open screaming, he stuffed his big cock in effectively shutting her up. Kayleigh couldn't believe it, she felt like the entire weight of her upper body was supported by his big, thick dick. She started to cautiously suck his dick.
She was worried that if the dick slipped out of her mouth she would lose support and slam down on the man below her.
Meanwhile, the fat man behind her was fully erect. He was fixated on her ass as it was riding up and down his friend's dick. Like a zombie he walked towards her ass and started to squeeze each glorious cheek. He forced her pelvis down on his friend's dick and held it there. He split her ass cheeks apart until her delicious ass hole gaped open. Without any regard for Kayleigh's poor anus he forcefully shoved his thick dick in. "OWWWWW" Kayleigh screamed as she let go of the man's dick in her mouth and collapsed onto the man below her.
She had never had a dick even close to the size of this man's in her ass before. The man in front of her again pulled her up by her hair. "Bitch did I say you could stop sucking my dick?" he screamed at her She sucked up her pain and returned to sucking off the large dick in front of her.
The man below her slapped her hard on the ass "Bitch this dick isn't gonna fuck itself." The tall man below her screamed She started to slowly start writhing on his dick again.
The man behind her started to fuck her faster as her ass started to slowly become a bit more accepting of it. Kayleigh felt like she was being torn apart internally with the two dicks in her pussy and ass. All the poor girl could do though was focus on the monstrous dick in front of her. "Fuck this school girl is a cock sucking pro." The man in front of her said. Without much warning he pulled her head by the hair, too his dick out and came on her face with just as much cum as the other man.
"Damn bro you right, jizzing on a pretty white face like this feels so good." The man below her said "Damn I wanna try, bitch suck my dick." He took his dick out of her pussy and slid upwards. He forced her mouth onto her cock.
Kayleigh gagged on the sheer length of his cock. She had never had a cock this long in her before she felt like it was almost at her stomach! Soon she felt the snake like cock withdraw as she knew what was coming next. She closed her eyes and felt a hose of warm white cum on her face. She felt like she was drowning in cum. She felt the cum drip down her chin onto her chest and breasts.
Meanwhile the fat man behind her was going to town on her asshole. He had each ass cheek in a death grip, using his grip as leverage so he could fuck her asshole harder.
Kayleigh had never felt this much pain before. She was literally in too much pain to scream. She had to make it stop. "Please fuck my tits instead, you'll love them!" She begged He stopped in his tracks.
"damn bitch that's not a bad idea." Kayleigh sighed relief as he withdrew his fat cock from her anus. It felt like she was taking the biggest poop of her life! He flipped her around and stuck his cock in between her soft luscious breasts. He squished her tits around his cock. "Damn girl you were right." He moaned. Soon he too came all over her big tits and chest. Kayleigh looked like she had taken a bath in cum. I made sure to take plenty of pictures. I felt like we could put these pictures on the main site of her page.
It just looked so demeaning and hot. Everyone paused as sirens started to blare in the background. "Oh fuck someone called the pigs!" One of them cried "It must've been that bitch in the alley next to us. She's always been too soft for these streets." The leader said "Leave this bitch here. We gotta run!" the short one exclaimed Before they could bolt, Johnny got out of the car and ran to them. "Hold on boys.
Bring her in here quickly." He said as he ran to his shop. "Bring the rope and mattress too otherwise they'll find the evidence." The men looked confused but knew that the man was right. They picked up Kayleigh and the incriminating evidence and rushed into Johnny's shop.
Johnny locked the store door and closed the blinds once Kayleigh and the vagrants were inside. We drove off down the street and watched as a police car came minutes later. The cops did a slow drive down each alley, before simply driving away. I took the moment to look down at the stream and chat.
"Holy fuck guys I've never cum that many times in my life. That was the best rape scene I've ever seen. God bless you guys, I'm going to tip you handsomely." I replied "Cheers! Glad we could keep you satisfied. We'll be sending you the edited video soon for your re-viewing pleasure." … Inside the shop, the men looked befuddled at Johnny.
Johnny welcomed them in to take a seat. As he did so go he grabbed Kayleigh by the rope and tied her to a pole in his shop. The men looked in awe as Kayleigh gave no resistance at all. He continued as he locked a black leather collar around her slender neck and connected the chain from the same pole to the collar.
"Sit girl." He commanded. She quickly took a seat on her allocated mat. Her eyes lit up as he brought a bottle of "Slut Candy" to her. "You've been a good girl Kayleigh, you've been a really good girl." He cooed "You made daddy so much money today." Kayleigh kept her eyes fixated on the pill as he took it out of the bottle. "You deserve this girl." He said as he held the pill in his palm in front of her. She hungrily lapped it up. The black men looked at each other and then looked at Johnny.
"Man what the FUCK is going on here." They said, almost in unison Johnny reached into his drug cabinet and withdrew some run of the mill extra strength Viagra, as well as capsules filled with herbs from Africa containing a powerful aphrodisiac. He walked around and gave each man one of each pill.
"Boys you can either sit here and listen to this old man explain a long winded story, or you can take these pills and fuck this hot young slut until your dicks get sore." The men looked at each other, shrugged and downed the pills. Moments later they looked at Kayleigh and barely recognized the innocent schoolgirl that they were forcing themselves on just a few minutes before.
She had made her way in between them and was on all fours, flushed and panting heavily. She was wiggling her ass at the short fat man. She took a hand and split her ass cheek out so that her asshole was staring at him.
She winked her asshole at him, essentially inviting his thick dick into her ass. She licked her lips as she stared at the tall man's cock. She took it in her mouth and engulfed it in its entirety, she moaned as she felt the length of it travel through her lips. The leader man took the image in before sliding under her and letting her ride his cock like cowgirl. Johnny smiled as he set up his cameras to film the scene.
Afterwards he went to the back and started to work on uploading the previous scenes on his website. He fell asleep and would wake up periodically to the sounds of loud moaning and fucking. Hours later he woke up and was greeted to silence. He checked the store and laughed at the scene.
The black men had left the store. Kayleigh was still leashed to the pole. But she had broken free of her rope tie around her hand. She was collapsed at the center of the floor. She had that familiar dream like smile on her cum covered face. She had a thick layer of dried cum on her face and tits. She had streaks of cum on her stomach and all around her vagina. Cum still seemed to be oozing out of her asshole.
Kayleigh looked like she was having the best dream of her life. Every now and then she would subconsciously lick some cum off her lips and swallow it. Johnny called us and we drove over to pick up our pet. It was night time, so Mr. Dudley picked her up put her naked body in the trunk of his car.
She barely even woke up throughout the whole experience. We drove her home, gave her a kiss on the head each and put her in her cage in the utility closet where she belonged.