The Bad Girl's To Do List

Chapter Two- Within Her Grasp

“A handjob?!” Court questioned Chloe as her brows raised and her mouth was gently parted. “Do you have any idea with who?”

Chloe did think long and hard about this. Her first candidate had been Derek as she hoped she would be able to scratch that from her list as well as get back at Drew. But she also wanted to bask in the glory of her revenge and didn’t want it to go away so easily. Plus, she wanted to be with someone she could trust. When she thought of trust and her first time doing anything remotely s****l, there was one face that popped into her mind.

“Sean? I thought you said he was like a brother?”

“I’ve always seen him as family…”

“Kinky…” Court commented as Chloe ignored this and focused on answering the question in more detail.

“But with it being my first time, I wanted to have someone I can trust...someone I know won’t pressure me or make me feel bad if I’m not good at it.”

“Well I know he won’t turn you away-”

“How can you be sure?”

“He’s a guy.” Court teased before moving from the office chair and moving towards Chloe’s closet before throwing the doors open in a dramatic fashion. “But you cannot get anybody turned on dressing like you walked out of a Hello Kitty festival.” She teased in reference to Chloe’s pink and white attire on this current day. “You have to have something in here that I can work with…” Court reassured herself before searching each item of clothing, coming upon incredibly cringe-worthy clothing for what she would usually wear. It was either complete with a skirt, glitter, or some shade of pink. “I might be able to do something with this…” She said as she pulled a dark maroon colored shirt with the saying “sarcasm is my second language” written in big white letters across the chest and abdomen.

“Put it on…” Court spoke as she waited for her sister to change as she scanned her sister’s desk before pulling the desired item in her grasp. Just as Chloe smiled as she feared her sister would have chosen an old Halloween costume and made it slutty, she was relieved to see just a plain shirt. However, Courtney wasn’t satisfied with how this look and so she used the scissors she had taken from Chloe’s desk and cut directly between her chest to show her boobs. It was done in such a way that showed just the top of her bra, that gave a sort of “sexy babysitter meets drunk sorrority girl doing the walk of shame”.

“What-”

“If you got them...flaunt them…” Courtney said as she moved back, proud of her creation before then turning to her sister’s dresser. “Now...for something more summery and not so...church girl…” She commented as she ruffled through the drawers until pulling out a pair of shorts that were more like capris. Again, unhappy with this, she took the scissors and cut them short enough to now be labeled as booty shorts. It was something she never would have worn before hand, even if paid to do so. However, Courtney still wasn’t done as she searched the bathroom located just across the hall.

“Sudden urge to shave?” Chloe asked in reference to her sister holding one of her more run down shavers.

“It’s not for me-”

“I showered this morning-”

“That’s not what I’m talking about...just sit still.” Courtney moved to her knees after placing a towel beneath her sister’s shorts to not nick her skin. By the time she was done slicing up the pants with scissors and a razor, she turned her usual pristine and pure sister into something almost polar opposite. She now had the persona of Megan Fox in Eminem and Rihanna’s “Love the way you Lie” music video-but only after Courtney pulled Chloe’s hair from its reserved braids and left it in loose waves.

“Now we’re talking…”

“I don’t know-” Before Chloe could finish her thought, Courtney slid a condom into her sister’s pocket. “Just in case-”

“Hey Court…” Chloe commented upon seeing her sister linger across the threshold of her room. “Thanks.”

Courtney gave her sister finger guns before leaving before she would have to answer to her mother about her questionable life choices. Chloe took her lead as she knew her mother would never allow her to leave the house looking as she did, and so she left soon after Courtney, having already texted Sean and telling him she was coming over. The stars seemed to align in this moment as he spoke of his parents having taken his little sister, Annie, to a movie as it was made from a favorite book of hers.

When Chloe found herself sitting in front of the house where she knew she would commit the first act upon her list, she looked at herself one final time in the mirror of her car before moving to the front door to the house she had ventured in nearly a million times. However, this time, there was much more at stake as she could lose her best friend. But she hoped things would work in her favor, but there was only one way to find out.

As the front door came open, Chloe found Sean to look to her with complete surprise before nearly choking on the piece of pizza he had in his hand. His nose had still been terribly swollen, but miraculously unbroken, with just a simple fracture. Due to this, it wasn’t in great need of anything but rest, ice, and tender love and care. The same thing that Chloe intended to give him.

“Um...Hi…”

“Can I come in?”

“Of coursh...mm-hmm-yep…” He spoke in a jumbled mess of nerves as he wasn’t quite sure what to make of this moment. He feared that it was some kind of horrible joke, but was along for the ride-whatever that would consist of. As she made her way deeper into the house, past the same rooms she came to memorize as if they were in her own home, she saw from the corner of her eye how he had quickly tossed the remainder of the pizza away from sight and returned to her. “Did you want to watch The Big Bang Theory? Play Mario Kart?” He asked in regards to the fact this is usually what they had done when she would come over-especially during the summer.

“I was actually thinking we could watch something.”

“Sure! What were you thinking? Something scary? Something funny?” He asked upon moving to his knees and to the small storage beneath the television where all of their movies were located. “Maybe-”

“Something romantic?” Her tone seemed to change from her usual comfortable nature to a more Marilyn Monroe seductive voice. This made him focus on her as he looked to her while freezing momentarily. Without even being close to him, Chloe could see his heart racing due to the spot in his neck that showed the beat of his heart. At first, she was afraid she was making a great mistake, before finding him to smirk to her.

“I think that’s the first time you suggested something like that…” He spoke as he wanted to make sure he was reading the situation correctly. “Did you have one in mind?”

“I’m sure we can find something…” She spoke as she patted the seat beside her as he pulled the Roku remote towards him and took the seat beside her. Able to smell the almost overpowering scent of vanilla and lavendar she seemed to douse herself in before leaving the house, he found himself even more drawn to her than usual. His eyes constantly moved to her knee, desperate to climb higher, but scared of being seen as something other than a good guy. He would then move back to the movies in front of them, but neither had been focusing on the titles listed in front of them.

“Did you want to watch this?” He asked without even looking at the screen and looking at her breasts from the corner of his eye, trying to be subtle about it, but failing. As he went to speak again, Chloe set her hand on his shoulder and pulled him towards her to gain his full attention. Without a word, she slid her hand over his lap to feel his phallus ready for pleasure beneath her touch. He shifted when feeling her graze him and terrified to question in fear that she would cease her actions.

“Is this okay?” She asked sheepishly as he couldn’t bring himself to look at her. Instead, he rested his head on the back of the couch and closed his eyes as he felt her rub over his member while remaining over his pants. As he began to seemingly move with her, his hands gripped the fabric of the couch as he felt pain omit through his lower waist as the fabric restrained him from being free.

“Are you okay?”

“It just...hurts a bit.”

Feeling somehow confident in this s****l moment, Chloe moved her fingers to the button of his jeans as his eyes followed her. She slowly unlatched the button to then carefully move his zipper down, careful to not catch any part of his manhood onto the downward motion. When he was fully exposed, she found herself surprised at his size as she knew only of sculptures from museums and erotic paintings from class but found him to exceed them greatly. She looked at it before taking it in her hand, finding him to gasp to the feeling of her flesh touching against his. It had been a moment that seemed frozen in time for them both as neither could believe what was happening-more Sean than Chloe in this exact moment. He watched as she began to move her hand up and down his shaft, feeling his body twitch to her gathering, before she would quicken her pulling as she could feel a light amount of substance ooze from the tip of his member. At first, she was curious to the act before finding that it allowed her the lubrication needed to make it more pleasurable for him.

She then brought the back of her thumb to scrape some of the excess onto his shaft and give him the feeling of wet pleasure, the kind that made him begin to moan and grip the couch beside him, nearly tearing the fabric from its resting position.

“Clo-” He spoke her name in a hushed voice as she found herself turned on by his raspy voice caused by her motions. She smiled to this as she could feel herself become damp at the sight of his facing meeting with the pleasure of her touch. She then quickened her hold, making it seem similar to that of being inside of her, without the complete warmth of her womanhood wrapping around him. For the past decade and a half, every single s****l thought that Sean had of his best friend and crush, came to fruition as he thought of every single scenario-never imagining this. His hips began to move along with her as he tensed seemingly impossibly so, growing harder until grabbing onto her hand.

“I’m gonna-”

“I want you to.” She said in a low voice as Sean kept his hand on hers until feeling her continue to slide him in and out of her grasp. She then noticed the reaction when touching the head of his member and continued to do this, to see him smirk and jolt with pleasure. “s**t…” He said beneath his breath as he felt himself climb closer and closer to an orgasm that he never thought would be shared in the presence of Chloe. Again, not wanting to question it, he stayed along for the ride. “God dammit!” He said beneath a quick breath that startled her just as he launched forward into her hand, releasing what he tried so hard to keep within, to not scare her away. But before a word could be spoken or a look exchanged, the door of the house came open and the entire family entered the home to find their son, and brother, upon the couch. He had been sitting with a blanket over his lap, although it had been ninety plus degrees outside.

Chloe had been able to run into the nearby bathroom and wrap herself in a cute sweater she left from the last time and was able to emerge appear like the wholesome girl they always knew she was. This was something that made her feel like herself, but in a way that made it somehow better. She felt as if she had stolen something and gotten away with it, but the high she had been given was something she had never experienced before. But it was the type of moment that made her illuminate almost as if the act had been done to her.

“I’ll see you, Sean-” Chloe spoke before giving hugs to his family and getting into her car and heading back to her own house, remembering the feeling of his come upon her fingers. While she was in the bathroom, she found herself in a daze of tapping her fingers together, almost as if she had placed glue. But she had to dispose of this evidence quickly and had done so by the way of the faucet and warm water complete with soap. However, the thought and feeling of his excess rested on her mind and the tips of her fingers as she made her way back to her room to mark this from her list with a big read marker, before then adding “Get pleased by Sean”. She immediately began to conjure scenarios in which this could happen , such as sneaking in his room or going to the park where everyone does to makeout during the weekends and summer nights. She felt as though an entire part of the world had opened up just for her, and this wasn’t even the beginning…