Quick Note: This is the start of a collection of one shots. Some I had written years ago and some new.

Disclaimer: Unluckily for me I was not the brains behind Cruel Intentions (but luckily for me neither was I for CI2 or CI3) or the characters. This is simply a one shot.

Warnings/Pairings: Sex scenes, swearing, drug use. K/S of course.


Ever since the first moment Sebastian had met Kathryn he had a strange infatuation with the beautiful brunette. They were inseparable after that first day. As they grew older their friendship started to grow and blossom until their parents announced their engagement and they both knew that they could never be more then step-siblings. But that didn't mean they couldn't imagine what it would be like. Sebastian had imagined many times before since that fated day what it would feel like to have Kathryn's mouth on his cock. He was 15 when his father married Kathryn's mother. He watched in horror as they said their vows and were officially declared man and wife and he now Kathryn's brother. Later that night feeling angry and upset he got drunk on a vintage bottle of scotch and fucked some girl he went to Summer camp with to alleviate his frustration.

That was 3 years ago. Today was a much different story.

Sebastian walked briskly up the stairs to the second floor of the Valmont townhouse and entered his bedroom only to find his step-sister perched on his mahogany writing desk downing a glass of vodka. He cocked an eyebrow at her as her eyes met his and a smile appeared on her face.

"Good afternoon brother dear." She sang.

Kathryn's legs were crossed making her tartan school skirt slide up her creamy thighs just that little bit more. He hated her school uniform, not because it was entirely hideous but because seeing her in it made him instantly think of her the ways he'd like to defile her and it wasn't often something he let himself think for the sake of his cock. Her white button down blouse was unbuttoned just that little bit more then it had been at school and he knew this was because she wanted his attention. Had she been waiting her all afternoon for him? After school he had gone to his favourite bookstore and spent an hour finding new books to read and talking to the attractive saleswoman behind the counter (getting her number and promising to call her that night).

"Sis." He replied in a sarcastic tone.

It was kind of sick and twisted they they referred to each other as brother as sister because the things they both of them were thinking in their head were certainly not sibling behaviour. In fact it was illegal and it only made it better.

"You didn't come straight home." Kathryn pouted.

He tried not to notice the way her lips did that. Her pout was a poison dart that had so often left him at her beck and call. He hated that about her. He hated that she knew she could get him like that.

"I was busy." He told her, not willing to share information.

It wasn't like he was out fucking some debutante, but he knew she would immediately think that he knew that would make her jealous. Not telling her where he was made he body swim with curiosity and jealousy and even though she'd never in a million years admit to that he just knew. Which is why he liked to be vague on details and let her assume what he was doing all this time. Most of the time she was too proud to ask him, for fear he'd think she was jealous. So most of the time she let it go and would pretend he had been at Blaine's or buying her something nice. Tonight was not one of those nights. She was curious tonight and angry that she had been sitting here for the better part of an hour waiting for him to come home so he could find her sitting here in this oh-too familiar position.

"What were you doing?" She asked, not for one moment pretending like she cared.

Sebastian shrugged his shoulders and fiddled with some books on his shelf. He didn't want to look at her because he knew if he did she'd give him some sort of look or do something that would make his cock stand at attention and he'd lose control and she'd have him only to leave him high and dry and awaiting a cold shower. He could hear her in the background tapping her fingernails on his desk which infuriated him to no end but he didn't let it show. He took a book out of his shelf and began flipping through the pages absentmindedly, not for one second planning on answering her.

"Answer me." She demanded.

He could picture the sour look on her face, not accustomed to not being answered. He was the only person to not bend at will and he didn't plan on ever being one. Yes, sometimes she got what she wanted, sometimes he did her bidding but it wasn't like he was some sad boy in love with her doing everything she asked. More often then not he would tell her no and she would leave in a huff.

"Why do you want to know?" He finally responded, placing the book back on the shelf.

"I'm curious." She quickly replied.

"Or jealous." Sebastian quipped back.

This made her blood boil. Kathryn was a jealous girl. But she didn't like to admit it. She liked to think that she was above that bullshit that no one or nothing could compare to her so how could she possibly be jealous of anyone or anything? It was true. She couldn't be compared to anything or anyone, but it didn't stop her from letting the green monster out occasionally.

"You wish loser." Kathryn spat.

"Then why do you care?" Sebastian asked, finally turning to look at her and cocking a perfectly arched eyebrow.

She didn't reply. She knew she had lost that one. It wasn't that she didn't know Sebastian was fucking every girl she knew. It wasn't that she wanted him to fuck her (okay so it was a little). She just hated the fact that any other girl could steal his attention from her even just for one hour. She knew of course that he was truly devoted to her, that given the chance he would bend her over and fuck her brains out and never look at another woman. But she couldn't let that happen so she watched on as he flirted with other girls and took them to dinner and fucked them. Yes, it made he insanely jealous.

Kathryn jumped off Sebastian's mahogany desk and sauntered over to him. The slight sway in her hips making her school skirt sway back and forth. She stopped a couple of inches short of Sebastian, her mouth a breath away. There was an intensely fierce look in both of their eyes, the tension in the air was thick. He wanted to pick her up and slam her against a wall and delve his dick so far inside her she'd scream for days and she wanted to push him down on the bed and ride his cock until he was so sore he'd never fuck again. They didn't show it.

"I'm going to a party later on, you want to come?" She questioned, her hand fiddling with his shirt collar.

Sebastian pondered the question for a moment. It was a Thursday night and although it wasn't strange for Sebastian to go out during the week he had a huge test tomorrow that he didn't want to be hungover for. But he wanted her to think he just didn't care for it. So he turned his nose up at the idea and shook his head.

"No thanks. I have things to do." He told her, their bodies still close.

"Like what? Writing in your queer journal?" She said.

His lips turned into a smirk. Queer as his journal may be, what Kathryn didn't know was it was more like a book about her. Every secret she had told him, every encounter they had shared was documented in their. His deepest, darkest thoughts about her and her horrid ways. The book proclaimed she was a slut, a cokewhore, bulimic and a bitch but it also told how he was in love with her. If she ever got her hands on it, he would die of embarrassment and then she'd bring him back from the dead only to murder him herself for writing such hateful things about her even if they were true.

"It's none of your business." He said back.

Kathryn tried not to care. She tried to act like she could live without him. So she shrugged her shoulders and she turned on her heel and went back to his desk where she proceeded to bend over and seemingly write a note on a piece of stray paper on his desk. He watched as her skirt lifted up high enough, revealing her white lace panties. He felt himself grow hard and started picturing bending her over that desk and slamming into her repeatedly. They were dangerous thoughts and they only led to rejection by her and him jerking himself off. So he swallowed the images of Kathryn and averted his eyes.

"I wrote the address down for you, just in case. Maybe I'll see you there." She purred.

"Doubtful." He called back as she exited the room.

A few hours later Sebastian found himself staring at the piece of paper. It was late, around 11pm. He had sat here thinking about what she was doing all night. He knew for a fact that by now she'd probably be as high as a kite thanks to her nose candy and probably flirting with some jock. He hated that thought, that a fumbling football player would get to paw at her and he couldn't even kiss her. He tried to close his eyes and let sleep overcome him but he found himself not able to sleep. He contemplated popping a sleeping pill but before he knew it he was dressed and out the door getting into his jag and driving to the destination of the party. He cursed at his weakness, he knew she would find this a victory. He would just tell her he was horny and that he wanted to take home a slut to bed.

When he arrived music was blasting from the house and there were several drunk teenagers on the front lawn. He didn't recognise any of them but then again he had never really taken notice. Sebastian ventured inside the building, working his way through crowds of drunk and oversexed teenagers. It wasn't long before he ran into someone he knew. Blaine Tuttle was the openly gay student at Manchester. Most of the students who were secretly gay were too scared to 'come out' for fear of their trust funds being cut off. Blaine however didn't care. He had been dealing drugs since he was 13 and he was fucking good at it. He had made more money doing that in the five years he had been dealing for then his entire trust fund held. Of course it was a risky venture and there were always cons to the pros but most of the time it was a good way to get fast cash.

"Sebastian!" Blaine slurred, throwing his arms around him.

Sebastian was a little bit of a homophobe. Blaine was a good friend and he genuinely liked the guy but the gay thing freaked him out. He was always wondering whether Blaine was just looking at him or he was picturing him naked which turned Sebastian off a lot and often made him blurt out homophobic jokes. Truth be told even though Sebastian was an attractive man Blaine wasn't really interested. Sure, if the opportunity arose he wouldn't say no but he wasn't about to chase Sebastian and convince him to turn gay. No, Sebastian was just conceited enough to think so.

"Tuttle. Hey." Sebastian said back, yelling over the music.

"I didn't think you were coming. Kathryn said you weren't. She said you were too busy slitting your wrists or something bitchy like that…" Blaine laughed, knowing that Kathryn had been sarcastic when she had told him that.

He rolled his eyes at the statement. Of course she would say that. Because it was totally out of the question that he might just want to spend one thursday night at home preparing for a test he had the next day. Actually it was a bit ridiculous. Kathryn was usually the one worried about grades, Sebastian was usually the one 'winging it'.

"Where is she?" Sebastian yelled.

"Kathryn? Uhm. I think she's upstairs…with a guy." Blaine revealed.

It stung a little to know that but Sebastian tried not to show it although Blaine knew better. He nodded in Blaine's direction and made the ascent up the stairs pushing past couples making out and dry humping on the stairs. It thought it absolutely disgusting that they couldn't control themselves. When he reached upstairs he had no clue which bedroom. He took a guess and figured the last one would be the most likely as Kathryn would not want some random drunk person stumbling in and ruining her sex. He contemplated knocking on the door but thought better she would probably just yell 'fuck off' anyway. He turned the doorknob and cracked the door and found Kathryn on her knees sucking off some loser he had never seen before. His blood boiled and he was immediately jealous. Before he knew it he had burst into the room.

"My, my what do we have here?" He said, a malicious grin on his face.

Kathryn's attention and instantly moved from the loser's cock to Sebastian.

"Sebastian what the fuck are you doing here?" She asked, wiping her mouth with the back of her hand.

Sebastian didn't both responding. Instead he walked over to the half naked loser and forced him on his feet by his shirt collar. With a stern unnerving look Sebastian pretended to be the big brother he was so not.

"That's my fucking sister you know?" He said.

"I-I didn't know man. She wanted it. She asked me if she could…" The guy stumbled, clearly intimidated.

"I don't care. Get the fuck out. If I so much as see you near her again I'll kill you." Sebastian warned.

With that the guy left, trying to pull his pants up along the way. Sebastian locked the door behind him and then turned his attention to his somewhat annoyed step-sister. Kathryn was sitting on the edge of the bed looking more then a little pissed off at him. He didn't care.

"What the fuck? Like seriously, Sebastian? Do I walk in on you fucking some dead pan slut and threaten to kill her?" Kathryn angrily spat.

"You have on several occasions." Sebastian replied.

Thinking about it Kathryn did recall doing so a couple of times. But it didn't matter, the fact was she wasn't going to let him ruin her fun or her night. She was high and horny and wanted to fuck. If that guy was too scared to now she would just find some other loser to get her off. Sebastian didn't scare her and she was sure he would give up after awhile.

"You're an asshole. Now if you'll excuse me I'm going to find someone to satisfy me." She purred, licking her lips.

As she got up off the bed and started to make her way to the door Sebastian pulled her down on to the bed and pinned her beneath him. She hated when he did this. He was of course stronger then her so she could never over power him and he knew it. She didn't bother to struggle or whine as she knew it would do her no good.

"You're not going anywhere." He told her.

"Why not?" She breathed, feeling the warmth of his skin on hers.

"Because you're high. I've told you a million times to cut that shit out. So when you're a little more sober I'll take you home but for now you are going to sit in this room with me." He instructed her, his arms either side of her tiny body.

Kathryn didn't know whether it was the drugs or not but something inside of her burned so intensely for Sebastian. He looked delectable in his black button down shirt and black pants, like her little devil Sebastian. His hair looked like he hadn't bothered and he smelled like he had recently had a shower. She wanted to kiss him so bad that for a few seconds she actually thought about doing it before her brain took over and she remember who she was thinking about and what could happen to her if someone caught her kissing her step-brother.

Slowly Sebastian moved away from her. He sat against the big billowy pillows at the head of the bed and eventually she joined him. They were silent but it wasn't uncomfortable or awkward. In fact it was a silence they often relished.

"Well if you're not going to let me find someone to satisfy me I guess I'll just have to do it myself." She said all of a sudden so matter of factly that Sebastian was actually shocked when her hand delved between her dressed and she started to touch herself.

"Jesus Christ Kathryn." Sebastian half whispered-half groaned.

His pants grew tighter the moment her hand had moved south. He didn't need much encouragement from her to get hard. Sometimes all it took was a glance his way and his cock was as hard as steel. She disregarded his comment and continued palming her cunt. She moaned and mewed in pleasure beside him, all the while Sebastian trying to hard not to plummet inside of her.

"Stop that. Now." He ordered.

"Mmm. But it feels so good." She purred.

"Kathryn seriously you don't know…Jesus. I can't…" Sebastian half protested.

On one hand he wanted to watch her little fingers delve into her tight cunt and watch her face as she orgasmed. On the other hand he knew it was torture. This would get him so hard he would need to jerk himself off and he would have to do that in front of Kathryn. Not that it was really a problem.

"Oh Sebastian." She moaned, that caught Sebastian off guard.

"Don't do that." He growled.

"Why?" She whispered back, eyes hooded and soft.

"You know why." He replied.

"Tell me." She breathed in his ear as she rubbed her clit.

Sebastian's breath hitched. "Because I can't contain myself. If you don't stop I'm going to get you on all fours and fuck you as hard as I want and you won't be able to stop me."

Kathryn moaned at the thought. "Sebastian." She was teasing him now.

"Stop." He said.

"Fuck. Sebastian. Yes. Oh. I'm gonna cum, Seb. You want me to cum?" She asked, doe eyed and lust filled.

"That's it." Sebastian said.

It was it. Sebastian and Kathryn and both lost their control. He ripped her panties right off her and dove his head between her legs. He had never tasted her pussy before and oh my God was it amazing. He licked at her and lapped up her juices willingly while Kathryn writhed and panted and pulsed beneath him. She was flailing around and he was having a hard time trying to keep her still. As his tongue dove into the hole she screamed out in pleasure grasping at strands of his hair and the duvet cover. He had never heard a more sexy sound then Kathryn screaming out because of pleasure he was inflicting on her. He knew she was close he didn't need to ask her be told. So he moved his mouth North and began nipping at her clit and encapsulated it inside his mouth feverishly sucking on it until she was cussing and screaming his name. She came violently beneath him several seconds later.

"Shit." She breathed.

"Fuck you taste good." He told her, licking his lips.

Eyes closed she smiled. Her body felt warm and tingly. It might have been the cocaine or it might have been Sebastian. Whatever it was it was fucking amazing and she didn't want it to end, ever.

"My turn." She smirked, opening her eyes.

Sebastian watched in shock as the girl of his dreams purred like a pussy cat and pushed him onto his back. All the years he had wanted her, all the years he had pictured her pretty little mouth sucking his cock. His dreams were about to come true. Kathryn snaked her way to pants and unbuckled them quickly releasing his cock from the confines of his pants and underwear. It sprung to life, harder then he thought he had ever seen it. She licked her lips in satisfaction. It wasn't the first time she had seen his cock before, hell she had seen it more times then she could count but it was certainly the first time she had been mere inches away from sucking it.

"Don't be a fucking tease." Sebastian warned watching as she hovered above his cock.

He knew her and he knew that she liked nothing more then to be a cock tease. But he was sure if she didn't hurry up and wrap her mouth around his dick he would shove it down her throat and not be sorry. She smiled up at him and in one foul swoop enveloped all nine inches of him. Sebastian's body didn't know how to react. He gasped and groaned at the intense and sudden feeling of warmth, gripping the sheets beneath him. He wasn't surprised she could take all of him but he was surprised she'd do it so soon.

"Yes. Fuck. Yes baby, suck my dick. Oh you're so good at that." He moaned, grabbing fistfuls of her hair.

Kathryn didn't need to be told how good she was. She had been sucking dick since she was 14 years old, which seemed kind of slutty but she didn't care. In fact she was sort of proud at how good she was, most men begged her for more. She grabbed the base of Sebastian's dick and started pumping it while sucking on the head, she had never sucked him off before but she was pretty sure she knew what he'd want. Sebastian wanted so bad not to let her think she was amazing but now that her mouth was around him he couldn't help but let it all out. She was fucking incredible and there was no way in hell he'd be able to contain himself while she was blowing him.

"Shit. You're amazing, fucking amazing. Oh. Like that, yes." Sebastian moaned as Kathryn started to lick and suck his balls.

Usually he didn't like girls doing that to him. Ever since that one time when he had a girl bite down a little to hard (which caused inexplicable pain for days) he was always very cautious. But Kathryn, hell Kathryn could have kicked him in the balls and he's sure he would have enjoyed it.

"You like my mouth on your dick Valmont?" Kathryn spoke, momentarily releasing his dick from the mouth.

"Don't stop." He growled angrily.

He could feel his release coming on. He could feel that familiar feeling burning inside of him and he wanted nothing more then to shoot his load down Kathryn's throat. Sebastian grabbed the back of her head by her hair and forced her down on his cock. She showed no resistance what so ever, gobbling his entire length. He pumped into her mouth fiercely several more times before he thrusted once more, releasing himself down her throat. If she was shocked, she didn't show it. She swallowed it up and licked her lips and present him with a wicked smile.

"Yummy." She purred in his ear.

Sliding her body up his Sebastian grew instantly hard. It didn't take much for Kathryn to get him all hot and bothered. She licked and kissed his neck and his chest as her crotch rubbed on his. Sebastian's own hands wandered endlessly up and down her now naked body (when did that happen? He thought to himself) feeling every bit of skin he could. She was soft and silky like one of her expensive night gowns. She rubbed herself against him painfully slowly, teasing him with her wet pussy. He was done being teased.

Sebastian grabbed her by the waist and sat them both up, Kathryn now sitting in his lap. He had a beautiful view of her perky little breasts from this angle which he cupped in each hand and began massaging. Kathryn threw her head back and pursed her lips. She kept grinding against him, desperate for any kind of friction.

"Mmm. Seb." She whispered.

He sucked a nipple into his mouth and listened as she gasped. There wasn't a more beautiful sound then that of Kathryn's pleasure filled gasps.

"You gonna ride me baby?" Sebastian asked, cupping her face in his hands.

"Mhmm." Kathryn responded.

Sebastian took hold of his cock and watched in great anticipation as Kathryn slowly lowered herself down on to him. He wanted to relish that first moment he entered her before. Sebastian had fucked his fair share of girls, seasoned whores and virgins alike and although Kathryn could probably be put into the former category she felt like the latter. She was as tight as any virgin he had fucked before. She began slowly moving her body with his, working the rest of his cock inside her. He was big, she had had bigger but he was a good size. It hurt a little but she kind of liked the pain he was causing.

This had been the most tender they had been with each other during this encounter. They stared into each other's eyes as she rode him, both trying to savour every last moment.

"So tight." Sebastian groaned as she clenched around him.

"You like it Seb?" She replied.

Kathryn began moving on him like no other girl had. At first it was slow and methodical but soon became more rushed and rough. Sebastian liked it. The faster she went the better it felt. He had been fucked by a lot of women, some much more experienced then Kathryn but none had been this good. Maybe it was because this was Kathryn or maybe it was just that she really was that good. He didn't know. Sebastian's lips brushed her neck, smelling her sweet scent. Every time Kathryn's movements got particularly rough and good he would bite down on her eliciting a high pitched moan from Kathryn.

Sebastian grabbed her hips and started to help her grind against him. Fuck he was close. He desperately wanted to hold off and fuck her for days, he knew that this would probably be the only time he would get the chance to be inside her. But he couldn't hold off, not for much longer. The feeling of her clamped around him, hearing her scream and cuss and whisper his name, it was all too much it was driving him insane. So he snaked his hand between them and placed a thumb on her clit, rubbing it and pinching it. Kathryn writhed against him.

"Jesus Christ! Fuck. Yeah. I'm going to cum." She screamed.

"Do it baby. Cum all over my cock." Sebastian said back.

With those final words her body quaked upon release, her walls clamping tightly around him which lead to his own climax. It felt amazing to cum inside Kathryn. She slowed her movements down until she completely stopped and slumped on top of him, his semi-hard dick still inside her.

"I can't believe we just did that." She whispered into his sweaty chest.

"Me either. That was…fuck there aren't even words to describe it." Sebastian replied, hands combing through her messy locks.

Just as he was starting to close his eyes and relax Kathryn pulled away and got off him. He looked at her dumfounded and watched as she gathered her clothes and began re-dressing.

"What are you doing?" He asked, propping himself up on his elbows.

"Leaving." She said.

"Wait. I'll take you home." Sebastian offered, starting to get up.

Kathryn turned around. Gone was the woman he had just had sex with, returned was Kathryn the bitch.

"Don't bother. This never happened. In fact if you so much as hint at this…this mistake I'll cut your dick off. Please no I'm not joking." She spat, her voice laced with venom.

He had no clue why she had suddenly turned her attitude around.

"What the fuck?" He asked, getting up.

"Stop. Right there. This," Kathryn began gesturing between them, "can't happen again nor did it ever happen. You're my brother Sebastian and this is illegal. If people found out…I'd be ruined in this town and the whole of fucking America. So what just happened was nothing."

"Step-brother."

"What?"

"We're not legally related."

Kathryn rolled her eyes. "Goodbye Sebastian."

Sebastian watched her leave. Of course this is what she'd do. What'd he expect? She would confess her undying love for him and they'd run away and live happily ever after. No, of course not. He just didn't expect this.


Author's Note: So it has certainly been awhile. I mean if you read my other stories you'll see that I recently updated 'A Kathryn Tale'. I'm still currently working on the next chapter (hit a road block) and was searching through my hard drive and found a bunch of one shots I had written many years ago. I want to post them (and possibly write some new ones) but I don't want to fill up the CI sections with a bunch of my stories. So I'm going to compile them here. I'll post them probably once a week. Hopefully you enjoyed this and are looking forward to reading some more.

Also if you're into one shots go check out 'Cruel Love Anthology' by Caroline Spencer if you haven't already. Her one shots are AMAZING and her writing is fantastic.

Drop a review and let me know what you thought.