[a/n]: time to get the story rollin'!

[summary]: "You're rich, right? I bet you five hundred dollars that you won't sleep with Jace Herondale before the end of Semester One." / Because when Clary Fray agreed to this bet, she had no idea just how much trouble she'd bring to her life. AU.


Cruel Intentions
"One of the cruelest things you could do to another person is pretend you care about them more than you really do."
-Douglas Coupland


[resident bad girl]

.

Clary Fray sighed, completed annoyed with the fact that she was wasting time in detention when she should have been at Jonathan's house, finally finding out what he'd been secretly planning for the last weeks of summer. Instead, Mr. Mac decided that since Clary wouldn't remove the unlit cigarette from her mouth during his Algebra class that he just had to assign her detention.

Thanks, Mr. Mac.

Clary wasn't the only one in detention that Tuesday afternoon. In fact, a few of the people Clary associated were in the room. Isabelle Lightwood, too classy to be called a slut but too flirty to be called loyal, was in a desk on the other side of the room. Her head was tilted back and her eyes were closed, her hands folded neatly in her lap while her legs were propped on top of the desk, crossed at the ankle. Clary's guess was she was in detention for too much PDA during school hours. Typical Isabelle behavior.

Simon Lewis, which wasn't too common but not unheard of, was also in detention, sitting a couple seats to the right of Isabelle and three seats to the left of Clary. He kept rolling his chocolate brown eyes and glancing at his expensive Rolex for the time ('pretty little rich boy' was how Clary liked to refer to him, even though they're friends). His long legs were kicked out on either sides of his desk, lain out to their full extension. He was probably in detention for arguing back with a teacher, something he did on occasion to 'spice things up'. Somewhat typical for him; Jace probably put him up to it.

The final person Clary associated with was her best friend, Alec Lightwood. He was sitting to Clary's right, discreetly texting someone on his phone. Probably one of his many sex escapees. Although Alec was gay, Clary knew he had a tendency to swing straight just for the fun of it. His dark black, almost blue, hair was falling into his electric blue eyes as he typed away on his phone. Once upon a (long) time, Clary thought he was hot. Then she learned he was gay and trained herself to only exchange light flirty banter with him from time to time. Anything farther then that was nothing short of incest, as she thought of Alec as her brother.

He was in detention for taking back to Mrs. Robinson during Civics, and Clary knew this because she was in the class when it happened. If she hadn't already had detention under her belt due to Mr. Mac, Mrs. Robinson wouldn't have hesitated to give Clary a detention because she'd immediately started laughing during their exchange.

"Mr. Lightwood," the detention teacher, Miss Jones, spoke, interrupting the peaceful silence. Isabelle opened one eye, Simon looked up from his watch, and Clary glanced to her right. He was just typing away on his phone like Miss Jones hadn't said a word.

"Mr. Lightwood!" she said again, her voice booming with annoyance. Alec looked up, raising his eyebrow.

"Can I help you?" he spoke, his cool and collected voice implying that he didn't really care that he was breaking one of the rules of detention: absolutely no cell phones.

"Put it away," Miss Jones snapped, glaring at the senior. With a roll of his eyes and a huff of air, Alec shoved his phone into the pocket of his jeans. He slid down in his seat with a sullen expression, and Clary had to hold back laughter. She snickered slightly, and Alec shot her a scowl.

On occasion, detention wasn't that bad, and this was one of those 'not bad' times. Clary would still rather be talking to Jonathan over this, obviously that didn't change. When Miss Jones finally released the students from the classroom (five minutes early, thank God!), Clary was the first one of the room, Alec right behind her, muttering something about Miss Jones needing to get laid.

"You'd volunteer, wouldn't you?" Clary said, with a smirk. Alec shoved her, although a smile was creeping onto his face. They both walked out of the school and towards the parking lot, where Clary had her car parked. It was a black 2016 Jeep wrangler, Clary's most prized possession (after her reputation at school, that is). She climbed into the drivers' seat and lit a cigarette while Alec slid into the passenger seat and presumed texting on his phone again. Clary was convinced he was the most gossipy person at school.

"Who are you texting so much?" Clary ask, taking a drag and backing out of the parking lot. "Please tell me you aren't getting your gossip from Maureen Brown. Even I know that's bullshit."

Alec scoffed. "Believe me Fray, I don't get my gossip from her. But guess what?" Without waiting for Clary to answer, he plowed on. "They're going to be a new teacher tomorrow, Mr. Bane. I heard he's hot, sexy, and single. Boy, I hope he's gay."

Clary raised an eyebrow. "Even if he's not gay, you could turn him."

Alec smirked, voluntarily putting his phone away for the first time all day. "True!" Alec looked out the window before asking his question. "Where are we going?"

"Jonathan's. He's been secretly planning something for weeks and today he's finally telling me what he's been planning."

"Oh Lord here we go," Alec deadpanned. "Nothing good ever comes from Jonathan and his schemes. Need I remind you the last time he gave us something to do? Jace was suspended for a month, Simon was facing expulsion and if it wasn't for Daddy Lewis paying enough money for the school to add four more wings, he would be gone, Isabelle was almost arrested, and you got a restraining order against Seelie."

Clary laughed at the memory. As a result of Jonathan getting bored junior year, he decided to start a drug dealing business in the basement of the school. Clary was all up for it; the more drugs, the better. Isabelle joined just because she had nothing better to do, and the golden boys of the school wanted to help out because they didn't want to be called goody two-shoes by Jonathan.

For a week it was successful, but then Seelie, the queen bee of the school, found out about it. One day, she followed Jace down to the basement, and she totally busted them. She had it all on camera, and no way was Clary letting her get away with proof. As Seelie was leaving with the video, Clary tackled her to the floor, knocking the camera away from the girl. However, Principle Meyers was coming down the stairs because he'd heard the racket, and he saw the scene. It didn't look good.

Isabelle was smoking cocaine off a spoon, Jace was counting the money, and Simon was high off marijuana. Clary got off of Seelie, and that's when everyone was dragged into the principle's office. Coincidentally, Jonathan was let off the hook because he wasn't there at the time of the bust and no one had the balls or the care to rat him out. Afterwards, it was really funny to joke about.

Clary shrugged, parking her car in Jonathan's driveway. "Nothing can be as worse as that; and besides, the restraining order was probably the best thing that happened during all of that."

Clary and Alec walked to Jonathan's front door, and Clary pulled the key that matched his lock out of her boot. She, along with Isabelle and Jonathon, had locks to everyone's houses; 'everyone' being Jace, Simon, Alec, and each other. Clary unlocked the door with ease, and they were in.

They found Jonathan sitting by his lonesome in the dining room, drinking alcohol from a glass cup, an expression on his face that oozed bored and 'too-cool-for-you'. Clary and Alec walked into the dining room and slid into opposing seats, as if they owned the house.

"Hey, Morgenstern," Clary greeted, coolly. "So what have you been planning for almost a month?"

.

[the mastermind behind it all]

.

Jonathan Morgenstern smirked, a devious smile lighting up his features. He was probably one of the hottest guys in school, if not the hottest guy. He had shaggy white hair that constantly fell into his almost black eyes. He had dark eyelashes framing his eyes, and freckles dotting his nose. He had a chiseled facial structure and big red lips that were on a different girl each week.

Jonathan's eyes grazed over Clary, from her curly red hair to her bright green eyes to her pale pink lips and her small, curvy body. There was a time where Jonathan had a considerably large crush on the girl. What could he say, she was hot. She wore skimpy clothing that when on her, didn't look slutty whatsoever. She wore thick combat boots that she considered her 'soul-stomping-shoes', and the way she sounded when she talked dirty...it was all so hot and so irresistible.

Least to say, Jonathan settled for a friendly crush on the girl, except a day didn't go by when he didn't think of slamming Clary against a wall and kissing her until she moaned for him to do more to her.

He pushed that thought away, then looked at the redhead. "Welcome, Fray, Lightwood. I see you both are interested in my little deal?"

Alec snorted. Although all six of the seniors had weird friendships and relationships with each other, Alec and Jonathan didn't get along that well. Alec thought Jonathan was a selfish bastard who got everyone in trouble just for the sake of his fun, and Jonathan though Alec was an uptight perfectionist who needed to loosen the hell up and live a little.

"I'll go wait in the car," Alec said, walking towards the front door. "It was nice seeing you, Johnny, but I'd rather be anywhere but here." With that, he slammed the door behind him.

"He needs someone to pull that stick out of his ass," Jonathan mumbled, taking a swig.

"Shut it, J," Clary defended, folding her arms. Jonathan sighed; he couldn't say anything bad about Alec without Clary wanting to beat him.

"Anyways, so I've thought of something that could make our final year in high school interesting." Jonathan smirked. "You up for a little dare, Fray?"

Clary's smirk matched Jonathan's. "When am I not, Morgenstern?"

"Touche, Fray, touche." Jonathan downed the rest of his drink, then reached into his pocket and grabbed hold of the cash he'd placed in there. He dropped the roll of twenty-five clean, crisp twenty dollar bills, altogether equaling five hundred dollars.

Clary raised an eyebrow, albeit she had an idea where this was going.

"You're rich, right? I bet you five hundred dollars that you won't sleep with Jace Herondale before the end of Semester One," Jonathan said, leaning forward on the table, his elbows on the wooden top and his eyes flashing with mischief.

Jonathan knew Clary wouldn't argue. After all, she'd had sex with every guy in the school (including Alec, but that was before he realized he was gay, or at least that's what they'd both said), except for Jace, and Jonathan knew Clary would love to get her hands on that boy. Jonathan could see it in her eyes; it killed her that they haven't had sex.

Clary nodded her head, but she had a similar idea to Jonathan's. "Deal. Me, Jace, by the end of the semester. But you, my darling, are going to do the deed too." She dropped five one hundred dollar bills on the table, all clean and crisp. "Sex with Isabelle by the end of the semester."

"And if I don't?"

"You're my little bitch for Semester Two. You do everything I tell you to do, even if that involves skinny a sheep and wearing it's skin like clothes." Clary smirked, leaning back in her seat. "You're free Semester Three, but you can't get revenge on me for anything I made you do."

"And if you don't?"

"Same deal."

"And if we both do it?"

Clary shrugged, a smirk toying at her lips. "Then you could say we're both pretty good at this game."

Jonathan stood up, and Clary did too. They met in the middle of the room, both of them already planning how they were going to achieve their dares. Each semester was three months long; Semester One going until the end of November, Semester Two picking up and going on until the end of February, and the final semester going to the end of the year.

Clary stuck her hand out, licking her slightly dry lips. "Do we have a deal, Morgenstern?"

Jonathan held her hand, shaking it determinedly. "We have a deal, Fray."


[a/n]: i know the pairings in this are a little weird, try not to think incest when you read clary/jonathan, because they're not related in this fic. the lightwoods and jace don't live together, jace and simon are roommates in their own apartment. alec and isabelle are siblings and they are friends, but they aren't supersupersuper tight.
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