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The Cruelest Game	By : dbud Category: 1 through F > Cruel Intentions Views: 4623 -:- Recommendations : 0 -:- Currently Reading : 0
Disclaimer: I make no money off this story and do not own Gossip Girl, Cruel Intentions, or Mr/Mrs Smith.

Chapter List
- 1-The Cruelest Game
- 1
Disclaimer: The following story is fiction. This is just a story.

The Cruelest Game

By Dbud

Warning: Story contains rape, snuff, and necro sex!!!!! Read at your own risk!!!!!

Starring:
Sarah Michelle Gellar as Kathryn Merteuil (Cruel Intentions)
Leighton Meester as Blair Waldorf (Gossip Girl)
Brad Pitt as John Smith (Mr. and Mrs. Smith)
And a special appearance by Blake Lively as Serena van der Woodsen (Gossip Girl)

Sitting in a limo in a dark alley, the athletic man in a grey suit looked out the window watching for anything out of the ordinary. The woman sitting next to him, and seeing his uneasiness, placed her hand on his knee.

"Relax Mr. Smith, everything is okay. You are such a nervous Nelly."

"It's just a limo isn't exactly inconspicuous. I usually try to keep a lower profile. You sure I can't talk you out of this?"

"Like I said, I insist on being there when this little bitch gets hers. This high school slut thinks she can fuck my husband and get away with it!?!? I don't think so! I want to be there when the life drains from this cunt's eyes."

The man sitting next to her took a deep breath, "Okay then. I suppose for what you're paying certain...considerations can be made for you."

Kathryn Merteuil smirked to herself. She was used to getting her way and had been raised to believe that adding zeroes to a check could solve any problem. She was a trust fund girl and socialite living in Manhattan. She spent her days fucking anyone she pleased while simultaneously screwing over those who pissed her off. She'd been doing this since high school.

Of course, eventually even she had to grow up. With no income of her own, she was blowing through her inheritance alarmingly fast. So, she had married an extremely wealthy man had begun spending his money.

"Let me go in first and take care of the cameras and any guards. I'll call you when the coast is clear."

As he began to step out of the car, Kathryn leaned in and slid her hand up his thigh, "I know I can be...ah, difficult to work for John but perhaps after we do this I can give you a bonus for your efforts."

As she spoke, Kathryn grabbed his cock and balls through the fabric of his slacks. She felt him stiffen in her hand.

"Let's, uh, get through this first and then we'll see."

She smirked at him as he slid from the limo and once he was gone poured herself a glass of champagne and leaned back. Sipping the flute, she began to think about what she was going to be doing in a few minutes but the idea of murdering her husband's mistress wasn't a frightening one for her as it would be most people. Instead, Kathryn found herself getting very turned on. She had been doing things like this, just not this extreme, for years. Toying with and destroying people's lives were a hobby for her.

She had personally seen that every person involved with getting her expelled from her prep school had been destroyed. Bankruptcy, revealing their sexual fetishes and affairs, even framing them for crimes were all the fun she had. But this, actually being present when her hired hit man, a very good looking hired hit man, wrung the life from this whore; well, she could feel her panties getting wet as she thought about it.

Putting one of her heeled feet up on the door she spread her legs wide and began to rub herself between her legs letting her fingers slip inside her pussy. Kathryn's head fell back and she closed her eyes as she began to pant and massaged the soft pink area around her pussy harder and faster.

"Oh fuck!" she moaned as she felt her orgasm welling. Just then though, as she was about to reach a climax, her cell phone beeped. Grabbing it excitedly, she answered it.

"This is John. It's clear, come on up. But come in the back entrance and use the service elevator."

"Ohhh John, I love when you say 'come in the back entrance' because I was just thinking about you doing just that."

He hung up and she smiled to herself yet again, "This is so much fun."

Lowering the partition between the passenger and driver's compartment, she spoke to the driver, "Wait here!" she said curtly. Not waiting for a response, she raised the black glass riser and stepped out, pulling her coat around her in the cold night air of New York.

She moved down the alley, jerking away when she thought her coat might have touched the corner of a dumpster, "Gross!"

Reaching the door at the end of the alley, she pushed it open and stepped through into a back hallway of the building. The sight of the security guard's body laying in a pool of blood against the far wall startled Kathryn and she nearly shrieked but managed to contain her emotion as she slipped past the body and stepped into the elevator. She didn't think much of him. The fact that his life and the life of the second guard and doorman working the late shift in the building had died for her twisted revenge did not occur nor matter to her.

Pushing the button for the penthouse, she rode the service elevator up to the top floor and stepped off. She walked through the rear entrance and entered the kitchen...

"In here," she heard John's voice and followed it through the opulent apartment until she reached the living room. She turned the corner and immediately a wide smile crossed her face as she saw the woman she wanted dead sitting on the edge of a chair. Standing in front of her, with a silenced handgun pointed at her head, was John Smith, the hit man who had left the limo a few minutes ago.

The young woman was beautiful, tall, with long full dark brown hair. She had full breasts, not overly large or fake like some Park Avenue women but her best feature was by far her face. It was perfection Kathryn noted as she approached. Even though it was now twisted into a look of shock at the sight of the alumni of her prep school where she was a senior and also the wife of the man she was fucking. No, the young woman's face was beautiful, no way to deny that; large almond shaped and colored eyes, full pouty lips, high cheek bones and a perfect little nose that Kathryn was sure was the result of a plastic surgeon. From under the short skirt the woman wore came her second best feature, her long toned legs, ending in a pair of high heels that Kathryn noted were to die for.

The nineteen year old girl stood as Kathryn Merteuil approached like she was greeting an old friend for lunch.

"Blair! Blair Waldorf! How long has it been? Ages it seems like!"

Kathryn's demeanor was over the top and with more flourish than was called for. She grabbed Blair by the shoulders and leaned in, stopping when her face was a foot or so away, and kissed the air. She then repeated the motion on the other side of Blair's head.

Stepping back, the warm smile which Kathryn had mastered faking faded quickly and was replaced by a sneer as she pulled her hand back and slapped Blair hard across the cheek.

WAP!

Blair Waldorf's head snapped to the side and she staggered back as Kathryn shook her hand to help with the stinging, "You fucking little cunt!"

"Ka-kathryn, I-I don't..."

Kathryn lunged forward and grabbed Blair by the hair, jerking her head back. Under different circumstances, Blair would have fought back and she could have easily subdued the older woman. Blair was nineteen and athletic, and, while not a fighter, in good shape while Kathryn was more than ten years older and barely stood five feet two inches and if she weighed one hundred pounds it would have been a surprise. But Blair didn't fight as she did not want the man standing in the room with the gun to get involved if she could avoid it.

"DON'T!" Kathryn held her finger up in front of Blair's face and cut her off, "Don't you fucking lie to me with that mouth you had wrapped around my husband cock just this afternoon."

Blair had been about to lie, to feign not knowing what this was all about, but she tried a different tact instead, "Okay, you're right and I'm sorry."

Kathryn stepped back, staggered a bit, like she had just been slapped, "What?!?!? You-you're sorry?!?!"

"Yes, I am, it wasn't supposed to happen. I was working as an intern at your husband's company. He and my parents are friends and we met and it just happened. I understand why you'd be upset..."

"Upset? No my dear I'm not upset."

"Kathryn slipped her coat off and laid it over a chair and then sat down, crossing her legs delicately.

"John, my hand hurts from where I slapped with bitch the first time. Would you mind?"

Without a word, John slipped the handgun he held into his belt and stepped forward...

WHACK!

A hard slap across the face tossed Blair against the wall. She looked up, her formerly perfect hair now wild and covering her face just in time to see a second blow land on her other cheek. She was thrown against a large bureau and sent the pictures and china plates flying to the floor where several of them shattered.

"Whoooffff!" Blair grunted as the edge of the bureau caught her in the gut.

"N-nooo, please, no more!" she screamed as John grabbed her by the hair and spun hard tossing Blair over the desk and sending her sprawling to the floor. As Blair began to crawl away, she saw a pair of small feet in front of her standing in a pair of very expensive high heels. Looking up she saw Kathryn standing over her, sneering down at her...

"Pathetic! You live like a whore and now you're going to die like one!"

Turning to her hit man partner, "Get her up and tie her hands!"

John complied and hoisted Blair to her feet. Pushing her over the desk, he pulled her hands behind her and produced a length of plastic, a zip tie, which he used to bind her wrists behind her. Pulling the gun from his belt, he pressed it against the back of Blair's head and held her there, on the verge of tears, while the two of them waited for Kathryn to speak.

"No, that's too easy for you, too quick. I want you to suffer bitch! I want you to feel some of the humiliation I have felt knowing my husband was getting serviced by a little high school slut like you!"

John lowered the gun, not sure what Kathryn wanted.

"Rape her!"

Both John and Blair's head's snapped towards Kathryn and in unison the both said, "What?!?!?"

"You heard me," Kathryn sat down on the plush sofa, this time taking a much more relaxed posture and spreading her arms out to either side of her, obviously enjoying her game, "Rape her!"

John seemed hesitant.

"Look, you said it yourself, for what I am paying you I get special treatment. Right?"

She didn't wait for an answer, "So, do it."

Blair looked back over her shoulder and her eyes met John's. For a second, she thought he might refuse or even help her, but those hopes were quickly dashed. John set the handgun down on the desk and shoved Blair forward, pressing himself against her.

"P-lease, Kathryn, don't do this! Think about this!"

"Oh I have cunt! I've thought about this moment for a long time."

Kathryn stood and walked over to the desk, while John was opening his pants. She turned and leaned against the large wooden desk as she continued speaking, "You see I've had a lot of free time. A lot of nights alone while my husband made up some lame excuse about needing to work late."

She turned and took Blair's chin in her hands, "But we both know exactly what he was working on, don't we?"

Blair flinched as she felt John's hands on her thighs as he pulled up her dress, revealing her perfectly shaped rear. Kathryn looked over Blair's shoulder and, seeing John's cock and the size of it, inhaled deeply and smiled.

"Oh my! You are in for a treat! That thing puts my husband tiny pecker to shame."

"You don't even love him!!!" Blair yelled at her.

Kathryn, seemingly enraged, jerked Blair's head by the hair and screamed back into her face, "THAT'S NOT THE FUCKING POINT! I will not have some little slut like you embarrass me like this!"

John prepared to enter the teenage girl who was quivering and obviously terrified when...

"Wait!"

Kathryn stepped around and John turned to face her, his cock jutting out between them. She looked down, eyeing his manhood and with a smirk, "I think I should give you that bonus we spoke of now."

Before he could utter a word, Kathryn dropped to her knees and took his length inside her mouth, swallowing his cock. Grabbing him by the belt, she pulled him towards her, forcing the entire length of his erection into her throat until her bottom lip was firmly planted against his balls. Kathryn gripped the leather of his belt tightly and even if John had wanted to break free, he was pretty sure he wouldn't have been able to. His head fell back as he felt her tongue working the underside of his shaft while she sucked hard on the rest.

John's wife, Jane, was one of the best cocksuckers he had ever known. That was half the reason he married a ball busting bitch like her. But Kathryn, all five feet of her, could definitely give even his wife a run for the money.

A few minutes passed as Kathryn worked John's cock hard wet before she finally stood, drool dripping from her chin and lips and panting from not being able to breathe, "I'd love to finish you off properly Mr. Smith, but I think we need to remain focused on the task at hand."

"Oh, ah, yeah, of course."

John had been so lost in the pleasure of Kathryn's mouth on him he had forgotten Blair standing only a foot or so away. The look on Blair's face told him that she too had hoped they had forgotten about her and somehow that she had gotten a reprieve. John forced her over the desk, bending her forward, "Pl-please don't..."

But before she could finish John entered her pussy from behind her, letting his cock slide inside. Blair stiffened but John held her down as he raped her. Blair Waldorf was certainly not a virgin, far from it, but being violated like this was nearly more than she could handle and the screams he let loose told both John and Kathryn that she was close to breaking.

"GGGYYYYAAAAHHHHHH!!!" she cried out loudly as John began thrusting hard in and out of her pussy.

Blair suffering was interrupted though by another sound, the sounds Kathryn was making. Blair looked up and saw her climbing onto the edge of the desk all the while, with her right hand, rubbing her cunt vigorously. Kathryn climbed onto the desk and was on her knees in from of Blair and with her free hand took Blair by the hair and held her head so she could look down into her face as she masturbated herself to orgasm with the other.

"God! You are beautiful! I can understand why my husband wanted to fuck you!"

Kathryn's head fell back and she began to make deep and loud panting noises. At the same time, John's was grunting behind Blair as he too reached climax. Both of them, the socialite and her assassin, came at the same time; John's filled Blair's pussy with his seed while Kathryn's pussy juices began to flow over her hand and dripped onto the desk.

"Ah, ah, ah, oh fuck!" Kathryn was panting as John collapsed onto the desk over Blair.

"Th-that was incredible!" she told Blair smiling down at her, "My god! I haven't come like that in years; certainly not since being married."

Kathryn swung her legs off the desk and stood shakily still recovering from her orgasm. Turning back to Blair though, "Let's get this over with. This bitch has lived long enough."

A look of panic crossed the younger woman's face. With her hands still tied, she was helpless to fight back. Her mind raced, looking for anyway out of this...

"Look..."she stopped not knowing what to call the man who was about to end her life.

"John," he told her.

"Look John. I-I don't know how much she is paying you but I can double it. I swear! My family has money, just tell me how much!"

"You are pathetic you know that you little fucking whore! First you fuck my husband and now you try to beg and buy your way out of getting what you deserve. PLEASE!"

"I'm sorry Blair but I'm a professional. Once I take a job I finish it and I can't be bought off. Just smart business."

"See there you cunt! Now fucking kill her! And make it hurt! I want to hear this little bitch scream some before she dies!"

John rolled his eyes but he had a job to do. Leaning down he lifted Blair by the hair and tossed her roughly into the sofa.

Kathryn was standing behind him and watching with the most evil look of glee on her face, "How are you going to do it? Not the gun right? That's way too quick."

John reached into his pocket.

"The knife? Gut the bitch, is that it?"

"Actually I was thinking how about a good strangling," John told her as he pulled a length of cord with two wooden handles mounted on each end from his jacket pocket. "You said you wanted her so suffer right?"

"Oh yes! Strangle the bitch! I wanna see the eyes bulge out of her head as she fights to breathe!"

Reaching down, John began to wrap the cord around Blair's throat. Considering her predicament, she was taking it well.

"P-p-please. Isn't there anything I can do?"

She looked up with pleading eyes.

"I-I don't want to die."

"Then you shouldn't have fucked my husband you fucking whore!" was Kathryn's response, "Now let's get this over with."

"Please John, listen to me. I-I have m-money..."

"JESUS! Not this shit again. He already told you bitch, you can't buy your way out of this."

"No, not to buy my life. I want to hire you John."

"What?" John asked as he stepped back, pulling the garrote from Blair's neck. Even Kathryn seemed surprised by what Blair had said.

"I know I am going to die but I want to hire you. You're a hit man right? So, why can't I hire you? Right now?"

"Oh, no," Kathryn waved her finger in front of her like she was scolding a child, "I see what your trying to do. No way! I hired him, he's my assassin."

"HEY!" John snapped loudly at his employer, "You don't own me. I work for whoever I want."

Turning back to Blair, "What are you offering exactly?"

"I-I'll pay whatever she did. Just give me an account number and let me use my computer over there and I'll transfer the money right now...out of my trust fund. You can watch me do it. I want to hire you to kill the woman who killed me. I want you to kill Kathryn."

John stood for a second thinking...

"You can't be serious about this..."

"SHUT UP!" John yelled at her, "I need to think about this. I mean, technically I would still be carrying out the original job so there wouldn't be anything unprofessional about this."

"Nothing unprofessional?!?!? Are you fucking kidding me!?!?!? I hired you to kill her not to turn around and accept her offer to kill me! Isn't that sort of implied, that you won't kill the person who hires you? And what about confidentiality? She wouldn't even know who I was if..."

John cut her off, "If you hadn't tagged along to watch; which I told you was a bad idea. I didn’t tell her who hired me; you did by being here to gloat."

Kathryn had begun to creep towards the exit of the room when John, seeing this, moved towards her. She ran, turning on her spike heels and moving towards the hall. John caught her easily and took her by the hair and slammed his fist into the petite woman's gut. Doubling over and retching, Kathryn dropped to her knees unable to catch her breath.

Pushing her down, John forced Kathryn flat onto her stomach and straddled her rear as he pulled her arms behind her. Within seconds he had slipped a zip tie around her wrists and pulled them tight as well as another around her ankles, binding her legs as well. Standing, he left her hog tied on the floor and moved back towards Blair.

Producing a knife, Blair gasped as he reached for her. She closed her eyes, ready for her life to end, but instead she felt him turn her and cut her hands free. Opening her eyes, she saw him produce a handgun and flick it towards the desk and the computer on top.

"Move," he said curtly and she did.

Sitting behind the desk, she turned it on as he wrote a long number onto a pad of paper, "Here's the account number."

A few passwords later, she was ready to make the transfer, "How much?"

"A quarter million," he responded. In any other circumstance she would have thought he was joking given the amount of money. But she knew this was serious business. Hitting a few keys strokes and then waiting for the progress bar to reach '100%'...

"Done. You have your money John."

She stood facing him, "So..."

"So," he responded back not sure what else to say given the awkwardness of the situation, "Why don't you go back to the couch?"

She nodded and walked around the desk. John watched her but he knew she wouldn't run. In some way, he admired this young woman. She sat back down and presented her hands in front of her, wrists together, for him. He slipped a new zip tie over them and secured it. Kneeling down, he did the same to her feet and Blair found herself in the same situation as Kathryn, still heaving for breath on the floor.

"Pu-leeze," Kathryn said weakly as John approached and stood over her.

Blair began to laugh. And not a weak laugh but a full and deep laugh, "Are you seriously going to beg? After all the speeches and insults? After what you did to me!?!? REALLY?!?!"

John turned to her, "Any particular way you want this done?"

"I think strangling sounded good."

John pulled the garrote from his pocket and knelt down, "But..." Blair stopped him, "I paid the same amount so I get the same thing right?"

John didn't seem to realize what she meant but the look on Kathryn's face told Blair that she knew exactly what was coming.

"Rape her first," Blair said this so matter of fact that John was shocked.

"Oh, yeah, of course."

"And..." Blair paused as if thinking about the words, "Put in her ass!"

Kathryn's head snapped around as she gave Blair a long dirty look. Tears began to roll down Kathryn's face as she felt him moving over top of her, opening his pants.

Kathryn felt him take the edges of her dress and with a hard yank, split it up the back and tear it open, "OH GOD NO!" she blurted out, not able to help herself.

Her rear was exposed and John yanked her thong down her legs with a hard pull as he positioned himself behind her. She felt the heat of his manhood between her ass cheeks as he readied himself to enter her.

"YOU CAN'T DO THIS!!! I HIRED YOU YOU ASSHOLE!!!!"

Looking over to Blair one last time as if to ask, 'are you sure?' John could tell that Blair wasn't going to change her mind. Taking a large handful of Kathryn's long straight blonde hair in one hand and guiding his cock between her buttocks with the other, he adjusted himself for a few seconds before a hard thrust shoved most of his cock deep into Kathryn's rectum.

"AHHHHHH FFFUUUUCCCCCKKKKK!!!" Kathryn screamed her ass rape began in earnest.

John kept pulling back hard on Kathryn's hair as he forced his weight down onto her, driving his erection deeper inside her asshole. Once he got it all into her tight rear, he began to thrust hard and forcefully.

"NNNNOOOOOOO!" Kathryn let out another long guttural scream.

After a few seconds, John let go of her hair and took Kathryn by the hips, lifting them and forcing her into a kneeling position but with her face planted into the carpet. Using his hands to anchor her buttocks before him, he began to thrust hard and fast, driving his full length in and out of her asshole.

"GOD NO! PLEASE STOP!" Kathryn cried out between sobs as tears ran down her face.

"BLAIR! PLEASE! TELL HIM TO STOP!"

Neither John nor Blair said anything as he kept pounding her asshole though. As far as they were both concerned, Kathryn was getting exactly what she deserved. Given the situation, Kathryn was a bit lucky as John felt his climax welling fairly quickly. He began to grunt as he had when he had raped Blair. Kathryn buried her face in the plush carpet as she felt his hot and wet cum fill her asshole.

He let her slid off his organ as he knelt over her panting and wiping the sweat off his forehead with his sleeve. Zipping up, he produced the garrote once again and wrapped it around Kathryn's tiny throat.

"Please no! Look Blair, we can just call this whole thing off!" Kathryn pleaded, the stains of her mascara running down her cheeks. Both women looked to John but Blair knew the truth. He wasn't going to be dissuaded.

"No, I don't think so Kathryn. This is the game you wanted to play, so let's finish it."

Blair and john traded glances and he pulled the ends of the garrote tight. Kathryn immediately began to struggle but both her hands and feet bound she was helpless. John lowered himself and sat down on the small of her back, pinning her. Wrapping the garrote tightly in his fists he pulled hard on both ends.

Kathryn's face was twisted into a horrified expression as if she now truly understood she was going to die. Her eyes began to bulge and her mouth was wide trying to get any air but unable to inhale even a single molecule. Her body began to jerk and she was slamming her heeled feet into the carpet as if trying to wriggle free.

John turned to Blair, "It won't be long now," he told her as if trying to comfort her.

Blair couldn't help but watch even though she knew this would be her own fate in a few short minutes. John yanked back on the cord, pulling Kathryn's head back and stretching out her neck. She was in her death throes now, even Blair, who had never seen anyone die much less a murder, could tell that. Kathryn's face was a deep red and her tongue was protruding, hanging from the corner of her mouth. Her entire body was shaking violently while her fingers clawed at the air and every muscle in her body tensed.

It was not a pleasant death to watch or to experience.

The jerking of Kathryn's body began to subside replaced by involuntary shudders. John kept up the pressure on the garrote but lowered her head and upper body to the floor, letting her lie face down on the carpet. Another minute passed and John slipped the cord from her neck. Reaching down, he pressed his fingers against her neck.

"Is she..."

John nodded but then he reached down and took a handful of Kathryn's hair and lifted her head. Seeming to cradle her head in his arms, John turned and spoke to Blair, "Just to make sure though..."

And with that, John twisted hard and the room was filled with a muffled 'KRAK!' sound as he snapped her neck violently. Blair flinched as she saw Kathryn go limp and John released her. Blair stared as Kathryn fell to the floor, her body twisted and her head at an unnatural angle and her large wide eyes staring off into the distance.

John stood and turned toward Blair who was fighting back tears.

"You're a very brave girl," he told her as he sat down on the sofa next to her. Reaching up he brushed the hair from her face, "And very beautiful."

"Pl-please, I don't want to beg, but is there any way..."

His expression told her it was useless.

"You can keep the money and...Maybe I can," she glanced down at his groin, "I could do something else for you."

He knew what she meant. John Smith had lost could of the number of desperate women he had been serviced by in a bid to earn their lives back. Normally, letting this pretty teenage girl fuck his brains out to try and buy her life before he ended it anyway would have been fun. But now, after what had occurred this night, he felt he owed her more than that. He placed his hand on her face...

"Sorry. I can't."

She lowered her head and nodded weakly as if to say she understood. He produced the garrote and she pulled away slightly.

"C-can I have a moment?"

He nodded and she fell against him. He was surprised since he was the man who was going to murder her. But in an effort to ease her fears John wrapped his arms around her and held her while she cried silently against him. After a few minutes, she pulled back.

"Ready?" he asked. It was a dumb question but she nodded as if she was in fact ready. He slipped his leg around her and sat down on the couch behind Blair letting her sit on the front edge before him. He wrapped the cord around her neck several times, "Just relax. It's easier if you don't fight."

Before she even knew it, he had pulled the garrote tight just as he had Kathryn. Blair suddenly found herself trying to breathe but unable to get any air into her lungs. Almost immediately, an intense burning in her chest swelled. She tried to take his advice and just let it happen but her body began to react to its impending death without conscious thought.

Blair began to thrash. Stronger than Kathryn, she was able to fight much harder although with little hope of avoiding the same fate. Like Kathryn, Blair's hands and feet were bound and so she could show her unwillingness to meet her end but not stop it.

John braced himself with his foot against the coffee table and leaned back, letting Blair jerk and move about on top of him.

"You are strong Blair," he told her with a tone of respect in his voice. This girl was a fighter.

She had already lasted longer than Kathryn and Blair was still thrashing wildly when John jerked her backwards and up onto the sofa. They were both lying on the cushions, she on her back and he on his side beside her. He slid his legs between her, intertwining them to try to keep her from kicking. He also, rolled onto her somewhat, using his weight to pin her as he tightened his grip on the cord.

John and Blair's faces were only inches apart as he stared into her eyes which were wide and filled with terror. Her face was turning red, as Kathryn's had and her mouth was agape in a vain attempt to get any air. She wasn't so much fighting as jerking and convulsing. He could tell that her death was not far off.

"Soon baby," he told her gently, "It won't be long now. I know, I know it hurts. But it will all be over soon."

Leaning down, John kissed Blair deeply as a violent tremor shot through her body. Her back arched and he tightened his grip with his legs to make sure she didn't get away. He did this not to be cruel but to end her without any more suffering. If she managed to wiggle out even slightly and get a mouthful of air, the entire process could be delayed for several more minutes. And she had suffered enough he thought.

She began to bounce up and down on the sofa, her hips slamming over and over into the cushions.

"I know you don't appreciate it, but it's a beautiful death," he whispered into her ear hoping she could still process the words.

Blair made a gurgling noise and she turned her face away from him, staring off into space as her face was twisted into a horrible visage of her former beauty; eyes bulging, skin a deep red, lips snarling and nostrils flaring. It was the face of a violent death.

Finally, and mercifully, she went still. Her body relaxed and stopped moving except for small jerks and shudders. John was panting and glad she had met her end. He also couldn't help but notice that his cock was rock hard. His crotch had been pressed against Blair's thigh as she had fought and struggled for life and the motion combined with his excitement and her beauty had gotten him hard a third time for the night.

He sat, Blair's long beautiful legs stretched out in his lap. Without thinking he caressed them, running his hand up and under her skirt. He couldn't believe what he was thinking about doing but then he thought, "Why not?" he muttered to himself.

"No one will know."

Looking around as if he was making sure the coast was clear, John flipped out a knife and cut the bindings from Blair's hands and feet. Her arms dropped to her sides and the one on the outer edge of the sofa fell limply to the floor. Taking her ankles he spread her legs wide revealing her sex to him. Her left leg he pressed back against the back of the couch while he quickly fumbled with his pants. It was as if he wanted to get this over with before he got caught.

Slipping his pants down to his thighs, he lowered himself, letting his cock slip inside Blair's still warm pussy. Hooking her right leg on his shoulder, he began thrusting deeply. John closed his eyes letting the pleasure of the moment wash over him. He had never enjoyed a woman like this. The sensations were incredible.

John had always considered himself a good lover and he took pride in the violent orgasms he gave his wife and the other women he fucked. But as enjoyable as those encounters were, this was different. Here there was no thought of her pleasure or what she was feeling. She didn't feel anything. It was a moment of pure selfishness where he could simply enjoy her body.

Leaning down he tore open the light silk of her top and began to suckle her left nipple as he kept riding her without mercy. Pushing her leg back, he pinned her ankle to the sofa next to her ear. Normally, he would have worried that he was hurting her, but that wasn't necessary now.

He watched as her breasts bounced rhythmically back and forth, slapping together in time with his thrusts. And when he felt his orgasm building, John didn't hold back. He began to slam his hips into her body as hard as he could with no thought of hurting her. He began to scream at the top of his lungs, enjoying everything about the moment until he could speak no more and his entire mind was filled with the inescapable pleasure of his orgasm.

He collapsed on top of Blair whose expression did not change one bit. He was heaving and panting and moaning into her ear as spurt after spurt of his cum filled her again. Gripping her hair, he curled his fingers into it and pulled so hard that, if she had been able to feel any pain, Blair would have screamed. But as it was, she simply lay under him.

Finally, he slid off Blair nit sure how long he had been on top of her. He stood and pulled his pants up when his cell phone rang and he answered it. It could only be one person.

"Hey baby," he called his wife.

"John, is everything okay?"

"Um, ah, yeah, "he fell back onto the couch still trying to recover, "Fine why?"

"I just hadn't heard from you. And you sound funny. You sure everything is alright?"

"Yeah babe, just fine. But you will never believe the night I've had. This is one for the memoirs. I'll tell you all about it when I get home."

"Okay then, I love you."

"I love you too babe."

He hung up and made the decision that while he would tell his wife about the unexpected double kill he would leave out the part about the rapes and after murder sex. No need to put up with three days of the silent treatment if he didn't have too.

He stood, stretching and yawning deeply. He still had work to do as he looked down on the two women. With his DNA inside both of them he would need to make sure they were never found. Stepping to the other end of the couch, he lifted Blair by the hair and sat down letting her head rest in his lap. While he was sure she was dead...

"Better safe than sorry," he muttered as he cradled her head in his arms. Setting himself, he gave her a hard jerk and heard the familiar 'SNAP!' as her neck broke. Blair rolled off his lap to landed face down on the floor with a 'THUD!'

Standing for a moment, he came up with a plan to help lighten his work as he frankly wasn't in the mood for several hours of digging. Walking out to the elevators he pressed the button and was surprised when the doors opened after only a few seconds. He was further surprised when a pretty blonde girl about the same age as Blair was standing on the car. She seemed startled to see a man she did not recognize there as well.

"Oh, uh, hi," she said to him.

John was used to having to improvise in his line of work, "Can I help you? Which penthouse are you going to?"

He took on the tone of someone who worked for the building or perhaps a security guard. He was hoping that she would be not going to the Waldorf's penthouse as there were two apartments on the floor. But since she had seen his face already John knew that even if she gave the right answer what needed to be done.

"Oh, ah, I'm Serena. I'm a friend of Blair's. We have finals next week and are having a study session tonight."

As Serena waited for John to step out of her way to let her pass she barely had time to register that he had produced a handgun from under his coat and held it to her head. Pulling the trigger...'Krak!' There was a sharp echoing retort as the silenced gun fired.

Serena's head snapped back as the small bullet hit her just about her right eyebrow. The bullet never exited but ricocheted several time off the inside of her skull tearing several paths through her brain and destroying it. She never even felt the impact or heard the shot.

Serena van der Woodsen, also a senior at the same prep school as Blair and Kathryn had attended, stood for a second, stiff with a dull expression on her face before she collapsed into a twisted heap; her arms and legs wrapped around each other on the floor of the elevator.

John sighed deeply, "Great, just great. Another body. That's all I need."

A few minutes later, John Smith approached the passenger side of the limo and, moving quickly, sipped inside before the driver, a fat greasy Italian guy, had a chance to even realize he was there. By the time he did, he also saw the gun which John had pointed at him.

"What's your name?"

"T-tony."

"Well Tony, I got good news and I got bad news."

"Wh-what's the good news?"

"The good news Tony is that you don't have to go into work tomorrow. But the bad news, is I have to decide if you're going to go anywhere tomorrow. If you catch my meaning?"

Tony didn't seem all that bright, probably the reason Kathryn had hired him. He didn't seem to be piecing it all together.

"Where's Mrs. Merteuil? Is she okay?"

"No Tony, she's not okay. In fact she's far from okay. She's dead and I killed her. After I raped her."

"Y-you ra-raped and killed Miss Kathryn?"

John nodded. He was about to put a bullet in fat Tony's head when the large man began to laugh almost uncontrollably.

"You killed that little bitch!?!??! Oh my god! That's great! I hated that little cunt!"

"Well I am glad you are so happy to hear about her demise but back to our little problem."

Tony held up his hands, "Look man, I got no beef with you. She didn't pay me shit and she treated me like shit. As far as I'm concerned she got what she deserved. I won't tell nobody nuthin'. I swear."

John sat back and thought for a few seconds. Turning back to Tony, "How would you like to make twenty grand?"

Tony's face lit up.

About a half hour later, John stood at the rear of the limo. The trunk was open and inside were the three bodies of Kathryn, Blair and Serena, all tossed in, their arms and legs intertwined. John paused and looked down at Serena and he felt his cock stiffen. She was beautiful, maybe even more so that Blair. After the fun he had with her, he couldn't help but think about having his way with the pretty blonde. Just then though...

"You, ah, you okay there Mr. Smith?"

"Uh yeah Tony."

The driver had climbed out of the car and stepped around the back. John slammed the trunk down sealing in the three bodies.

"You sure you understand what to do right?"

"Yeah don't you worry Mr. Smith. I got it all down pat."

John waited as if he needed more reassurance.

"I'm gonna take the limo to the address you gave me," he patted his front pocket where he had the slip of paper. And I give the car to a guy named Yuri and I tell him it's from you and it's a special delivery. Then I walk home. Man, easiest twenty grand I ever made."

John doubted he had ever earned twenty grand in his life but let it pass as Tony, a wide grin on his face, held up the envelope filled with cash John had given him.

"Good job Tony. And you drive the speed limit and you never say a word about me or what happened here. Right?"

"Awww, no way Mr. Smith. You can count on me."

"I know I can."

As the limo pulled down the alley and turned onto the main street John pulled a cell phone from his pocket and dialed. After a few beeps...

"Yeah hey Yuri, it's me John...Yeah, she's fine and still as hot as ever. Look, I'm sending someone over and I need your help with a job that got a bit out of hand...Great great, glad to hear it, I can always count on you. His name is Tony and he's driving a limo with three packages in the trunk...Yeah, you got it, I need you to make the whole thing disappear...Yeah even Tony. He's got twenty grand on him, is that enough?...You're the best Yuri. Give my best to the missus."

He hung up and walked out to the street to hail a cab.

The End.

Epilogue...

Kathryn Merteuil's eyes flickered open. Her head was pounding like she had the worst hangover of her life and she assumed that she was simply waking up from a night of sex and wild parting. And normally, that would be the situation. But as she climbed to her feet, she realized almost immediately that something wasn't quite right.

She was standing in a hallway. She had been lying on the floor. Looking around she didn't recognize where she was. A friend's house perhaps?

Turning she saw a large mirror mounted on the wall and was shocked to see that she was totally naked although still made up as if for a night out. Her hair and make-up were done and she wore jewelry and spiked heel but nothing else. While she was certainly no prude and had been too many parties where this would have been the dress code she didn't know what was going on.

Just then she heard a voice coming from a door down the hall. It sounded familiar but she couldn't place it. She walked towards the door and the sounds, "Hello? Is anyone there? I'm afraid I'm lost. Can you help me?"

She entered the room. It was well appointed and richly furnished but she still did not recognize it. She walked inside, looking for the person she had heard speaking.

Just as she was thinking no one was there and she about to leave, she heard the voice again, this time though from right behind her.

"Well hello sis."

Kathryn spun and nearly screamed out in shock as she saw her step brother, Sebastian standing before her.

"How've you been?"

Before she could react, he wrapped his arms around her and gave her a big hug.

"Se-seb-Sebastian? Oh my god? But..."

"I know, I died almost fifteen years ago."

Kathryn was in total shock, "This must be a dream, no, a nightmare. Or I'm on drugs, yeah that's it. I took some ecstasy and I'm hallucinating."

Sebastian stepped a few feet away and began to unbutton his shirt as he spoke, "I know I know and normally any of those explanations could be true but just not in this case."

"I-I don't understand."

Sebastian continued to get undressed. He had peeled his shirt off and was now unbuckling his pants.

"Wh-what are you doing Sebastian? Where are we? Please what's going on?" Kathryn was nearly in a panic as she spoke and watched her brother strip completely naked.

"What's going on? Well, I'm collecting on our bet."

He grabbed Kathryn by the hair and forced her over the arm of a large leather chair. Her ass sticking up in the air.

"What?!?! What bet?!?!?"

"You remember sis? The one we made before I died! The one where I get to put it wherever I want."

She looked back over her shoulder at Sebastian who was stroking his cock and eyeing her tight little ass.

"WHAT!?!?! You can't be serious? After fifteen years that bet still isn't..."

She stopped talking as if something occurred to her, "Wait, did you say you died?"

He nodded as he stepped up behind her. She ignored the fact that she felt the tip of his cock between her ass cheeks as she tried to digest the situation.

"But if you're dead than that means..."

"Yep, you're dead to sis. It'll all come back. Takes a few hours for you to remember usually. And as for where we are, I think you can figure that out too if you try."

"B-but why do you get to do this to me?"

"Oh, they just said I could have first crack at you before they take you."

"They? Who do you..."

Just then Kathryn looked up and was struck by what she saw. The room she had been in was gone. Instead, while the chair remained, the rest had disappeared and she was now in a large cavern, larger than anything she had ever seen. Standing about fifty feet away watching her and her brother were several hundred, perhaps even several thousand, creatures. They were unlike anything Kathryn had ever seen.

Each stood nearly ten feet tall. Their skin was a mixture of black and dark red and grey colors and smooth, like a snakes'. Their bodies were well muscled thick six pack abs and thick thing and powerful arms. Their hands ended in large claws and their feet weren't really feet but instead hooves. Their heads were definitely not human. They sported long backward curving horns and snouts and a maw filled with rows of jagged teeth.

Kathryn whimpered as she stared at them and their most terrifying feature. Each of the creatures had jutting from between their legs the most enormous cocks she had ever seen. Each was more than two feet long and the thickness of a Louisville Slugger. The tips dripped with fluid that sizzled when it struck the stone floor.

"oh god!", she muttered.

"I'm afraid not sis."

Kathryn barely even registered the sensation of having her brother push his cock deep into her asshole.

As he began to ream her rear hard, " Not even close Kathryn. Oh, and by the way..."

She looked back at him as he ass fucked her. He was smiling as he looked down at her.

"They get to put it wherever they want too."

The end.
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The Cruelest Game

Disclaimer: The following story is fiction. This is just a story.

The Cruelest Game