The Bad Girl's To Do List

Chapter One- The Origin of the List

"How about tonight?" A young man dressed in the maroon and white letterman jacket he earned from playing football the last four years asked his girlfriend as she was set upon his lap. "You always said on graduation night..." He spoke into her neck before placing a teasing kiss that sent shivers throughout her entire body. The truth of it was that she had thought about it every day for the past four years, but always held herself at such a high standard that she wanted it to be when she was engaged or married even. It was how she was raised. But he had other plans, and he had a tendency of being incredibly persuasive. She had thought about it so much to the point that she had dressed in her best lingerie sets for the past year, in case the moment would arise, but she felt as though the night was finally upon them.

"Do you want to go somewhere private?" Chloe asked upon pulling back from a set of sweet kisses as she could feel the desire and passion grow more intense with each following buss. Drew nodded as he followed Chloe into a back room of the house where the peers had gathered to celebrate graduation. There had been a Post Malone song playing within the living room which reverberated into the room they took for their personal use. From the minute the door closed, Drew had his hands upon her body, outlining every curve of her body until coming to her hips and pulling her into him. Chloe could feel a feeling of uneasiness in her stomach as she felt Drew begin to tug at her shirt before eventually lifting it into the air, revealing her white lacy bra. It had been a bra that spoke of her personality as it was both light and pure-at least in this moment.

Chloe's long dark hair cascaded down her back as she brought her fingers to Drew's shoulders to remove his jacket and then focus on his shirt. Her nerves began to grow the best of her as she felt Drew's lips trace along hers, ignoring the fear in her eyes and tremulous touch. In his own way of trying to ease her, Drew placed his kiss upon her shoulder as she covered herself nervously.

"Do you have any idea how sexy you are?" His words made her blush before her eyes connected with his.

"Really?" She asked, truly unaware of the beauty she was. Even with her Snow White appearance, complete with dark hair and fair skin, and a thin yet curvy figure, she was still oblivious to her level of attractiveness.

Drew nodded. "I love knowing I am the one that gets to bed you first..." He spoke the words so crassly to her as she cringed at them, a notion he saw, but ignored as he just wanted her. Having now felt her kisses diminish in passion, he pulled back and scanned her carefully.

"Are you having second thoughts?"

She shrugged as Drew was obviously upset, but trying to remain somewhat polite. "We've waited four years...And you've done this to me SO many times...come on...baby...we love each other...we are going to be together...so what's the problem?"

"It's different for a girl...You've had s*x before..." She spoke almost ashamed to say the words before moving to the bed, sitting in the center while she kept her breasts covered with her arms.

"I know, babe, I'm sorry..." Drew now sat beside her, wrapping one arm around her until it rested on the opposite side her waist then from where he was sitting. "It's been so hard to be around you with that little cheerleading uniform and not be able to please you like I want to. You are so damn sexy and I feel like I'm going crazy being unable to have you..."

She smiled to him kindly as she searched for words to thank him for this, but found a gentle kiss would suffice. This kiss turned into one of a deeper passion as she was laid onto her back and Drew moved to unbutton her pants. Upon doing so, there was a gentle buzz within Drew's own jeans that Chloe chuckled upon feeling upon her palm.

"It's probably Derek..." He spoke when pulling his lips from her chest. "The perv probably wants in on this..." He commented with a chuckle before resuming his task as he was now focusing on removing her bra. With the phone having been repeatedly active in his pocket, Chloe went to pull it free, to be sure it wasn't one of his parents, before seeing a text read over the home screen.

"You said you were gonna dump her and now you're gonna fk her...wtf!" The message made Chloe confused for a moment as she read it three times before sitting straight up. This forced Drew to fall to her side and look to her with a chuckle.

"Babe, I'll go easy-"

Chloe slowly nodded before looking at the message one more time, making sure she read it correctly before considering what to say.

"Did you go easy on Em?" She asked before throwing the phone onto the bed beside him. He scanned it quickly before jumping up as he saw her search for her clothes.

"It's not what you think, babe-"

"Don't call me that-"

"So we're done because of a text message?" He seemed surprised by this, as if he expected her to keep her mouth shut and head held high.

"No..." Drew seemed relieved by this as he went to touch her before she held her hand out in front of her, keeping him at a literal arm's distance. "We're done because you can't keep it in your pants." And with this, Chloe moved quickly from the back room where Drew had been calling her name in repetition before she made it to the front of the house. Unfortunate for Chloe in this moment, she had been driven to this house by Drew who she now had no interest in speaking to for the potential time of the rest of her life. Luckily, however, her best friend, although usually not an attendee of a party such as this, just happened to be there on that night.

"You okay Clo?" His kind voice set her pain at ease as she moved to him and wrapped herself within his embrace.

"Did you know?" She asked upon speaking against his shoulder as he stood somewhat tall over her, but perfect enough to hold her so she felt safe.

"About what?" He questioned upon hearing her sniffle.

"Drew and Em..." The names stung her lips as she thought she would spend the rest of her life with Drew and she considered Em to be one of her best friends, if not her best friend. Due to the look upon Sean's face, she knew that it was a not-so secret that she seemed to be the last one to know about. "How long?"

Sean shrugged.

"Please...just tell me..." She now pulled further back from Sean as she wasn't sure how she would react upon hearing his answer.

"Chloe-"

"I know it's serious when you use my full name."

"It's really not my place to tell you..."

"I am NOT talking to him."

"I get that...how about I just take you home and we can talk about it tomorrow?"

Chloe nodded as she followed Sean to his beat up solid black truck with spots of rusting that was courtesy of living in a state that supplied salt upon the roads. However, the sight of this car had been a sort of therapy for Chloe. Sean and her had spent countless hours within the battered seats of that automobile while discussing every single problem they shared in their adolescence. This consisted of conversations in regards to their future colleges, getting dates for dances, and even weekly talks on their favorite television show; The Big Bang Theory. But this specific moment had been one more tender as it was one in which she had been soaked in her own tears with her makeup having been smeared across her usually perfectly applied face.

"I'm not sure how Petunia will feel about having another woman in the car after so long..." Chloe smirked at this as he had allowed her to name his car, as she thought of the most feminine name she could to give. Sean was such a good sport about it, however, that he never made a fuss over it. "You'll just have to make sure she doesn't hear you talk about other cars...especially other trucks..." Sean spoke as he pulled the door open, as he had done every single time he drove Chloe somewhere. He had done this out of the plain fact that he was raised a gentleman.

"My mom is talking about going to the cabin before I go off to college-" As Sean began to try to distract Chloe, she found that this had the opposite effect for what it was intended to do. Instead of thinking of fond memories at the Sheridan cabin, she thought of Drew embracing Em in the way that she thought he had only done so with her. The thoughts and visualization stung her eyes and mind as she found Sean to reach over to her, having stopped at an old fashioned diner.

"Maxine's?" She asked upon seeing the neon sign illuminate the late night sky.

"It seems to me like you can go for one of their strawberry swirl shakes-"

"With extra drizzle and whipped cream." She finished her order with a smile before they both made their way into the diner, finding a nervous young man-who had worked their no more than week as he moved to them quickly for their order. Very rapidly, a woman appearing in curly dark brown hair and a uniform fitting for the theme of the restaurant moved to them.

"I got them, Joe, do you two want your usual?"

Both Sean and Chloe nodded as they made their way to the bar, in their designated spot, before waiting for their orders to be brought to them. As Sean scanned Chloe's expression, looking for any sign of happiness in her obvious disdain, he moved to the jukebox in the far corner and put in a song that he knew would make her smirk. Within a matter of seconds, the classic Elvis Presley song faded and changed into another vinyl of the song chosen by Sean. With its first beats being played, "White Sports Coat" by Marty Robbins played. Chloe's eyes lit up when hearing the tune as she saw Sean move in a vintage rhythm fitting for the 1950s.

"You know what's coming..." Sean spoke as he extended his hand, just as the waitress placed her drink upon the counter.

"Here?' She asked with wide eyes as he nodded, using every finger but his thumb to motion her towards him. As they locked hands, they began to perform their dance that they had made when they were between diapers and High School Musical ages. It began with a hand jive that turned into a close dance where the two would pull apart then come in close twice before he would then dip her. It was a cute moment shared between them two, the waitress who knew their orders by heart, and that of a small handful of late night snackers who came in to either sober up or come down from a high.

"I can't believe you remember that..." Chloe commented upon taking her seat and bringing the shake to her lips. Sean found himself to fixate on her lips momentarily before focusing on the vanilla shake brought to him. Just as a smile focused on Chloe's face, the chime of the door coming open drew both of their attention as it was revealed to be Drew. He seemed truly distraught as he searched the diner until seeing the couple at the bar.

"Can we talk?" He asked as Sean clenched his fists and Chloe gripped her glass tightly in her grasp, not caring for the stinging cold of the ice cream.

"No." She spoke as she turned back to the diner sign and acted as if she hadn't read it a million times.

"Do you want to go?" Sean questioned upon seeing her grow understandably uncomfortable. He then moved to place money on the counter to pay for their usual orders and prepared to pull his keys out to leave.

"We shouldn't have to leave because trash walked in..." Chloe spoke to Sean as she acted as if Drew hadn't been in her vicinity. But this would be hard as he took the open seat beside her.

"Eventually you'll have to talk to me...you know it will drive you nuts-"

"No. What drives me nuts is knowing that you slept with Em. I can live with never speaking to you again or looking at you. Come on, Sean." She instructed as she led herself to the door with Sean following quickly behind. However, as Chloe felt she was breaking from the moment, she found Sean to follow after her.

"Please, just let me say my side of things..."

"I don't need to hear your side!" She argued back.

"Don't you want to know what really happened?"

"No. I don't want specifics. I don't want to talk to you. And I don't want to see you!"

As Drew went to speak, Sean stepped in front of him, moving his hand to his chest. Although Drew was more muscular than Sean, and intimidating, Sean was going to protect his best friend at all costs.

"Just give her some space-"

"Butt out of this Sheridan!"

"Come on...give her time to cool off."

"Chloe-"

"Just let her-"

"Don't tell me how to handle my girlfriend."

"Ex girlfriend!" Chloe corrected as she had her arms now crossed in front of her.

As Drew went to grab Chloe, Sean moved in front of him, making this impossible. "Give her some-" Before Sean could finish his sentence, a fast hit came to his face as Drew had punched him and knocked him back. Immediately, Sean cupped his hand over his nose and blood began to emerge from the bottom of his hand and leak over his lips. Chloe's mouth dropped open as she then moved to Drew, hitting onto his chest hard enough to leave bruises before he caught her arms, laughing at her attempt.

"I'm actually glad it happened this way...I was trying to be a good guy, but there is no nice way to say that your girlfriend is boring! Even if we were to actually have s*x, I bet even a fork in a toaster would have more of a kick in it than you!"

"I'm so glad I never slept with you!"

"You're the only one! I've had so many and you had no idea...but everyone else does-" Drew commented as he casted a look to Sean.

"He didn't tell you? Shocking, since you are supposed to be "best friends"-" Drew placed physical air quotes around these words, before continuing. "And he saw me with at least three other girls-"

"I didn't want to hurt her!" Sean said while still clutching his nose. "Some of us HAVE morals!" He challenged before Drew pulled himself towards his sports car placed a few spots down from the truck.

"I can't believe I spent four years of my life with someone like you-"

"Ditto!" She shouted before moving into the car, focusing on Sean before he set the keys in the ignition.

"Are you okay?" She asked upon seeing his shirt now become stained with his blood.

"It's funny, mom thought that I would always break my nose in baseball-I showed her." He tried to laugh before wincing at the pain.

"Why don't you let me drive?"

"And a chance of you wrecking my pristine automobile? I don't think so." He teased in an attempt to lighten the mood before driving in the direction of her house. As they pulled up to the middle class home that appeared nearly identical to the houses surrounding it, aside form a few lawn decorations and the number on the house, Sean paused.

"I hope you know I wanted to tell you...I just didn't think I could break your heart like that." He spoke to her as she looked to him with disappointment in the situation.

"I wish I would have known...I almost slept with him..."

The words stung Sean as he had a visual of this, knowing she deserved better-knowing HE could treat her better.

"Thank you. For tonight. Despite Drew...it was actually alright."

Sean nodded before feeling Chloe lean to him and place a soft kiss on his cheek. He was thankful for the darkness in the car so he could conceal his blush but he turned to her, finding her still close to his face. He found himself desperate to show his feelings for her, but knew it was not the time as he didn't want to be a rebound if she would even reciprocate his feelings.

"I'll see you later Sean."

"Goodnight Clo..." He then waited for her to get into her house before driving away as she made her way up to her room. When throwing herself onto the bed, she went to turn and change into her pajamas before seeing a female figure taking occupancy on her office chair located diagonal from her bed.

"Don't stop on my watch." Her sister teased as she moved at her side, seeing how she had been crying before doing the dutiful sister act and pulling her into a hug. "Are you okay?"

As Chloe began to nod, this turned into an opposite motion of her head moving back and forth to show "no". She began to cry once more, this time in the arms of her sister, Courtney-whom was every part of Chloe she was afraid to be. Courtney was the girl who dressed in clothes two sizes two small, or with enough cleavage to make even a homosexual man look twice.

"Is it that asshole, Andrew?"

Chloe gave a disapproving look that emerged from the side of her eye before sitting up fully on the bed.

"He has been cheating on me...our entire relationship...I almost had s*x with him, Court!"

"Almost as in you didn't, right?"

Chloe nodded.

"Good! Your first time should be with someone who cares about you...someone who won't push you...guilt you..."

"YOU are giving me relationship advice?"

"I may have a bit of a reputation...but I know what I'm talking about...I'm just REALLY bad at following my own advice."

"I won't argue there."

Court playfully pushed her sister before moving to the other side of the room and rummaging through her sister's desk drawers.

"So how did you find out about his infidelity?"

"He told me I was boring...that I would be horrible to have s*x with...and that he's slept with "So many girls"..."

"Disgusting.." Court said with an obvious shudder as if a ghost had gone through her body. But as Court found this humorous, she looked to her sister to see the pain still self evident upon her face.

"You aren't actually mourning his ass are you?"

"No...I mean...a little...I was ready to do it...I just...couldn't...maybe if I would have then he would still want me-"

"Even if you were the loosest girl in that school, he is still NOT the person you should be with."

"I was kind of hoping that before I went off to college that I would...Just to know what it was like, you know?"

"I get it...You know...you can..."

"I'm not going to see some random guy JUST to lose my virginity-"

"I wasn't going to suggest that..." Court said as she moved to the desk drawer nearest to her and pulled out a piece of paper with the top labeled "To-Do" in a pretty light pink decorated with flowers as a border.

"What are you doing?"

"I am making you a to-do list for the summer." Upon the first line had been "Get laid" written in Court's sloppy handwriting.

"Classy..." She commented before rolling her eyes.

"Would you rather I put make love?" Court teased. "You said you wanted to before college, just do it, then. It can be anyone...guys are really good about not wanting a relationship after sex...even before. You can pick anyone...even that nerd friend of yours-"

"Sean?!"

"He has the potential..."

"He's like a brother to me!"

"Okay, not Sean then...how about the asshole's best friend?"

"Derek?"

"Sure...sleeping with him would piss Andrew off and give you your first time."

"I don't know..."

"Here..." Court turned away for a short amount of time before turning to her sister and handing her a list with four more items written on it.

"Have oral...Try BDSM...Try role playing...and a threesome?!" Chloe looked to her sister with disbelief. "Are you serious?"

"It's like a bucket list...A fuc-"

"I get it it!" Chloe interrupted before her sister could say the words.

"How about it? For the summer? Give yourself a list of things you want to do. Sexually."

"Don't you have to HAVE s*x first to have a list? I'm not exactly a secret w***e or anything....the only thing I know about s*x is the scientific names and locations..and that lingerie is what you wear."

"Okay...so I have an idea..." Court took the list once more, this time adding three more items.

"Watch porn. Go to a s*x club. Try Cyber sex." Having red these, although a blush was still prominent, Chloe seemed more open to these.

"Maybe if I try to ease into it-"

"So you'll do it?!" Court seemed too excited for her sister's s****l exploration.

"I'll try..."

And with that, the origin of the list was born…