Disclaimer: I do not own Durarara! or any of the Characters. All rights go the the original authors and creators.

This story will be loosely based on the movie, Cruel Intentions. (I don't own any rights to the movie either!) If you've seen it, you'll get some of the references. If you haven't, the movie is basically about a pair of bored, spoiled step siblings who take pride in making others miserable. They plan to deflower the new headmaster's daughter when she moves in with their Aunt during the summer.

Some characters may be just a bit OOC to fit in with the story.

Enjoy~

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Chapter One

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"Orihara-san."

...

"Orihara-saaan!"

...

"Izaya!"

The teacher snapped and sent her chalk flying at the 16 year old, striking him in the forehead.

"Hai~" Yawned the raven haired boy.

He gazed up at his sensei, his crimson-brown eyes still half lidded from his nap.

"So sorry to wake you, but you're wanted in the principal's office." The teacher called over her shoulder as she scribbled onto the chalkboard.

"Tch.. Third time this week. That's gotta be a record.." She muttered to herself.

The class whispered among each other as he stood from his desk and stretched his limbs. A few girls giggled and his male classmates glared at him as he cooly passed through the aisle, hands stuffed into his pockets and his usual smirk on his face.

He hummed to himself as he trotted through the halls of his domain, Raijin Academy.

Izaya knew every student; popular, unpopular and anything inbetween; and they certainly knew him as well.

Orihara Izaya had a reputation for being a troublemaker at every school he had been to, this one was no different.

Several teachers scoffed and closed their classroom doors and he skipped past, waving into the doorway at a few female students. He laughed to himself at how uncomfortable he could make the adults here.

Izaya stopped at the door of the principal's office to fix his uniform as he peered into the small window. A young brunette woman was seated at her desk, furiously scribbling onto a clipboard and shuffling through stacks of paper.

"Heh.. Namieee~ I'm back. Did you miss me?"

He smoothed out his hair and stepped inside.

"Good morning!"

Izaya smiled brightly as he leaned onto her desk and poked the Maneki Neko figurine placed at the corner. "How is everything going today, Yagiri-San?"

"Orihara-san. What a surprise." The stoic secretary muttered without glancing up.

"You know where to go, have a seat over there and wait for the Principal to call you into his office."

She pointed with her pen and continued to flip through her files.

"Hai, hai!~" He chirped and plopped onto the blue plastic chair. Namie continued on with her paperwork, giving Izaya empty responses to his ridiculous questions.

He kicked out his legs and sighed as he stared around the room.

"Well this is never any fun." He pouted, folding his arms as he slumped back in his seat.

Just then, the Principal's door came flying open.

"That's bullshit!"

Izaya perked up in his chair as he realized who the voice belonged to. Shizu-Chan!

"Heiwajima-san, please! C-calm down!" The principal sputtered out with his hands raised.

"Those jerks can provoke me to the near point of insanity, and you're saying I'm just supposed to sit there with my tail between my legs!? You know these kids just want a show from me, like I'm a freakin' Circus act!"

"Let's see how long we can piss of Shizuo before he grabs something heavy and flings it at someone's head!"

"I-I'm very sorry Heiwajima-san, but you know the school policy on violence! I'm going to have to give you detention for the rest of this week!" The man explained, taking a step back from the fuming teenager.

"Tch! This school is fucked!" He growled and kicked over the trash bin with his foot.

Izaya grinned widely at what he was hearing. Raijin's Bleached Blonde Beast was at it again.

"Orihara-san, I'll be seeing you in here now." The principal called as he gathered the trash that had spilled out from the toppled over bin.

He jumped up from his seat and made his way towards the door. The blonde stepped out of the doorway, his face was beat read with anger.

"Th' hell are you looking at! Ah?" He shouted as he stormed passed Izaya, slamming the door on the way out.

Izaya looked over his shoulder and chuckled to himself.

Poor little Shizu-chan, you're never gonna have any friends with that attitude.

Placing the trash bin beside his desk, the principal took his seat folding his hands atop the glossy wooden frame.

"Ahem.. I-I'm sure you can guess why you're here, Orihara-san. I need you to learn.. Y-you've got to give these bad habits of yours a rest, son. You're a bright young man with everything ahead of you. Yet you surround yourself with trouble, day in and day out.. Don't you have any clear set goals for your future?"

Izaya's smile faded and he shrugged his shoulders with a sigh.

"Well, sure. I have dreams and goals just like anyone else. But I know someone like me could never truly fit in with the rest of society. I've always been the black sheep in my family. My mother and father moved away from me to avoid dealing with such a troublesome child. I'm nothing more than a doomed soul, plagued for failure and misfortune for the rest of my worthless life."

The principal wore a pained expression. "Wait just a moment.. I-I've got something I want to give to you."

Izaya watched as the man pulled something from his desk drawer and walked over to him. A book was placed into his lap.

He raised a brow at the cover. The title read, Be Your Best You by Sanji Takada. It was rather dated. Like it had been published in the 80s. He flipped it over. A picture of a man in a yellow turtleneck was flashing a bright smile with his thumb raised in the air.

Izaya choked back a laugh, forcing an impressed look. "Sugoi.. You wrote this, Pricipal Takada?"

He gave a curt grin with a nod.

"Believe it or not, I was a motivational speaker back in my years. This was my most famous piece of work ever released. I do hope it can help you find yourself, your potential and who you truly want to be."

Izaya stood with his head down, sniffling. "I don't know how to thank you.."

"Just think of it as a gift." He explained pulling a few tissues from his desk. A small picture sat beside it of young girl.

He took the tissues and wiped his nose. "The girl on your desk. She's really beautiful."

"My daughter." He smiled.

Izaya looked on in amazement. "Wow.. If only I could have a girl like her at my side."

Principal Takada frowned and pushed the frame behind him. "Sorry to say.. but she's out of your league, young man."

He showed him to the door. "Now I want you to do well to keep yourself out of trouble, you hear me?

"Hai, I understand.. It was nice talking with you. Thank you very much for the book, Sir."

Izaya shut the door behind him and Principal Takada took a seat at his computer. The phone on his desk rang, and he paged it in.

"What is it Namie?"

"Your daughter, sir."

"Can't it wait?"

"I'm afraid not."

"Hah.. Very well."

He pushed the button to answer the line. "Hello?"

Sobbing was coming from the other end.

"Sniff.. Sniff.. oh.. Daddy! It's horrible! Just horrible!"

"Sweetheart, calm down. What is the matter?"

"There's...sniff, sniff.. pictures!"

"Pictures..? What do you mean?"

"He said that he loved me..! Sniff.. and now there's.. awful pictures of me on the internet!"

He gasped and gripped the phone.. "You have go to be kidding me! How could you be so careless!"

"Sniff.. Sniff.. I was so stupid!"

He tried to coax her into relaxing enough to tell him the link to the website. He typed in the address and dropped the receiver to the floor.

In the center of the screen was his daughter posed more provocatively than he ever needed to see.

Underneath in red flashing text read: Be your best you.

He jumped from his desk and sprinted out into the Secretariat's office.

"Izaaaaaayaaaaa! You get your worthless ass back here right now!" He shouted, slamming his fist on the glass. Several staff members rushed to his side to hold him back and get him to explained what happened.

Izaya peered from the stairwell up into the window and gave the principal a wave before waltzing back to class.

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"Detention, again.. Man this stinks!" Izaya sighed, crumpling the blue slip of paper into a ball and punting in down the hall with his foot.

Shinra Kishitani walked alongside him, clutching his books to his chest. "Well you did kind of go a bit overboard this time.."

"So I posted a few photos on the Dollars website of the Principal's daughter.. Big whoop! Maybe she shouldn't have been practically begging me to meet her in the girl's locker room if she had a boyfriend. Not that I cared. I had my bit of fun."

He giggled and Shinra closed his eyes in disapproval.

He sighed and hung his head. "And yet.. I've grown beyond bored with these air headed bimbos at Raijin! It's way too easy.. and it's always the same!"

"Blah blah.. Izaya, you're so cool! Izaya, you're so hot!"

"Blah blah.. Izaya broke my heart.. Blah!"

"Theres gotta be some excitement left in this dull excuse for a high school!" He whined and threw his arms out as the pair stopped at the lockers that lined the halls.

"Look Izaya, we've been friends since elementary. I know you've got your reputation to uphold or whatever.. but why don't you just give this whole thing a rest.." He said, pushing up his glasses.

"Becauseeee Shinra, I don't plan to live an ordinary boring life like you and the rest of you humans! I want to get as much out of it as I can. I want to try everything it has to offer, starting with its degenerate pleasures." He smiled and loaded his books into his locker.

"Besides, the reactions and facial expressions I get out of my schemes are the most fulfilling! You should really try it sometime. It's like nothing else in this world!"

Shirna inwardly shivered at his strange friend's disturbing hobbies and closed his locker. "I don't think I'll ever truly understand you.."

The two walked to the lunch room and stood in line to grab some food items from the cart.

"Look out everyone! Heiwajima's got a lunch tray in his hands, do you think he'd break it over someone's head if they looked at him funny?" A kid seated a table jeered.

Several kids laughed and others averted their eyes from his gaze in fear of the boy's words being true.

"Hey, you guys knock it off! You already saw what he did to Hajime last week." Yelled the transfer student, Tom Tanaka. "He's still recovering from his dislocated shoulder in the hospital!"

He turned to Shizuo and patted his shoulder. "I'm really sorry about those guys, Shizuo. I'll make sure they leave you alone."

The blonde grumbled to himself and grabbed a few cartons of milk from the cart before sulking away to a lonely table near the window.

Izaya and Shinra exchanged glances before carrying their lunch to their table.

"Hi Celty." Shinra blushed as he pulled out his chair and took a seat next to the object of his affection.

The black hood of her jacket hid her features as she tapped her fingers on her cellphone.

[Hello Shinra. Izaya.]

Izaya chipperly greeted the shy female and plopped down to enjoy his food.

"Can you believe Izaya's got detention again!" Shinra mused.

[What for this time?]

"Exposing the Student Council President for the promiscuous bird she really was." He chuckled.

Celty shook her head in shame.

[And who calls girls 'birds'..? We're not in London, Shinra]

"Well I can't help it that these girls practically throw themselves at me. Seduction is like a game of chess, you make all the right moves and you're exactly where you want to be. But it's no fun if your opponent is basically handing over the pieces!" Izaya whined as he peeled his banana.

"It completely erases the thrill of the challenge.."

Shinra chuckled to himself. "You know what would be a challenge.." His words trailed off as his eyes glanced over to Shizuo's table.

Izaya snorted, almost choking on his water. "Shizu-chan..? You're kidding, right?"

Shinra smirked and took a bite of his sandwich. "What? You said you were bored of these Raijin girls, and I know you're no stranger to fooling with the opposite gender. So why not him? If you want a challenge, there you go."

Izaya tapped his chin as he gazed over at the blonde outcast.

"He doesn't interact well with others. And he's as shy as a five year old when it comes to girls. Dominating Raijin Academy's Bleach Blonde Beast would be my greatest victory." He proclaimed with his hand on his chest in an act of self righteous admiration.

"Pffft! Ha ha ha! Like you even could! It was just a hypothetical suggestion." Shinra laughed as he poked his straw into his juice pouch. "There's no way you could actually do it!"

Izaya's smirk faded. "And why couldn't I?"

Shinra caught his breath after taking a long swig of his drink. "Because it'd be impossible!"

"Nothing is impossible, Shinra. Not for me." He replied with a grin. "I could work at it as long as it takes."

"Really?"

"Really. I'd say that I could have Shizu-chan head over heels for me me in just three weeks." He declared confidently, holding up three fingers.

"Three weeks? You've got to be joking. There's only two months left before the school year ends! I doubt you could even do it by then!" Shinra argued.

Izaya folded his arms and smirked widely. "You really underestimate me, Shinra. I had the Student Council President on her back in only three hours."

"So you really think you can take his virginity before summer vacation? You must have a death wish!" Shinra whistled.

Izaya smirked, his crimson eyes glinting with determination. "Care to wager on that?"

Celty slumped back in her seat and pulled her hood down even further as the two bantered on with their idiotic conversation.

"Then let's seeee. If I win.. you have to finish all my homework and study guides for the rest of the year. And that new laptop of yours, it's mine." Izaya said flashing Shinra a sly smile.

Shinra flinched. "The rest of the year? And you're talking a brand new HD laptop with a dual core processor and 4 Gigabytes of RAM!"

Izaya yawned. "That all sounds extremely interesting, so are you in?"

Shinra chewed his bottom lip as he thought. "Fine. And if I win.. you're going to have to get a picture of the school secretary's underwear!"

Izaya stopped smiling and grunted. "Do you have any idea how much trouble that could get me in?"

"Not to mention, Namie is freakin' scary when she wants to be." He whispered, picturing the ice cold woman's gaze as she beat him to a pulp.

He pushed up his glasses and smirked as he stuck out his hand. So are you in?~" he said, mimicking his tone.

Orihara Izaya was never the type to let someone show him up. And now was no different. Izaya smiled, and grabbed Shinra's hand.

"You've got yourself a deal, sweetheart."