Chapter Title: Take a Risk

Rating: Rated T but I put M due to the high percentage of smut in the future.

Pairings: Jeremy/OFC

Disclaimer: This story is based on the The Vampire Diaries tv series, with which I do not own. I do not own any characters except for the original ones of course.

Summary: How Jeremy's first day back in school went...

Warnings: Language, Drug Use and Sexual Situations. You've been warned.


It was a saturday morning in the Mccollough household and Kaitlin was spending it, laying on her back while her head hung over the edge of her bed. She had her head dangling over the edge as she played with one of her old stuff animals. Her door opened abruptly and Kaitlin saw the long and tan legs of Chloe in the middle of her room, looking down at her.

"Let me guess; you're still contemplating about your decision to put Jeremy in the friend zone?" Chloe guessed. Kaitlin lifted her right leg up and pointed at her as a yes. Chloe grabbed her foot and yanked it, causing Kaitlin to yelp and fall off the bed.

"What was that for?" Kaitlin huffed as she sat up. Chloe dropped her bag beside her along with the other shopping bags she had.

"I'm getting you out of this funk like now." Chloe declared. "It's been two weeks since you stopped things between you and Jeremy. And since then, you have been in deep depression mode. So I am changing that. We are going to the victory party Tyler is throwing at his family's lake house today." She leaned down beside Kaitlin and began to go through the bags, pulling out various pieces of clothes. Kaitlin got up and sat on her bed.

"I'm really not in the mood for celebrating Lo. Plus, I have homework and some yearbook picture editing to do tonight." Kaitlin whined. Before she could go on to her next point, a navy blue bikini was being thrown at her face and landed in her lap.

"Try this one on. The color and cut would look amazing on you." Chloe stated as she pulled out a much smaller bikini for herself. Kaitlin held it out and looked at it, smiling at the style.

"Okay, I like this bathing suit but I'm not going." Kaitlin mumbled. Chloe turned to her and crossed her arms.

"What was that? I think I heard you saying that you would love to go to the party so you could show off that hot bod of yours." Chloe said jokingly. She sat on the bed next to Kaitlin. "Kaitlin Erzsebet Mccollough, you are going to this party with me today, whether you like it or not. Plus there will be plenty of other hot guys there besides Jeremy Gilbert."

"First of all, hot bod?" Kaitlin asked. Chloe nodded eagerly. "And second of all, what did I say about using my middle name?" She groaned.

"What? It's not my fault your parents are into family cultures and stuff." Chloe mumbled. She began to take her jeans off. "Now, put that bathing suit on or else." She said seriously.

Outside the lake house, teenagers were letting off some steam by partying. Jeremy felt like one of them with a halfway empty cup of beer in hand while he stood by the lake, skimming rocks across the water.

Ever since Kaitlin had decided it would be better for them to be friends, Jeremy had felt even more confused than he was. He kept going through the memories that led up to that Friday night two weeks ago, trying to figure out what he did wrong. But everything seemed to be going perfectly when he thought back on it.

"Hey, the party's inside dude." Jeremy heard Tyler say. He turned around and saw him and Matt walking closer to him. "Don't tell me you're going back into you emo loner boy stage." Matt punched Tyler in the arm, knowing that it wouldn't do much to the hybrid. "What?"

"What he meant to say is what's going on with you Jeremy? We haven't seen you act like this since... Anna." Matt said, knowing it was a sore topic for Jeremy. Jeremy looked down at his shoes, not wanting to talk about.

"It's nothing guys. Just stress and stuff. Don't worry about me." Jeremy pleaded. Matt nodded his agreement even though he didn't agree with it. Jeremy was a little brother to him and since they both didn't have a lot of family, they needed to watch each other's back.

"You're getting something stronger than beer my friend." Tyler said as he pulled the cup from Jeremy's hand and tossed it out. Jeremy sighed and the three boys began to walk back. As they neared the lake house, a white volkswagen beetle pulled up in the driveway even though there was a strict rule not to park on the driveway.

Before Tyler could go over and intimidate the driver, Jeremy pulled him back just as Kaitlin and Chloe got out the car. His attention was mainly on Kaitlin as he noticed she had on a dress that was surely a shirt with the first four buttons open, giving the world a peek of her navy bikini that looked tempting even with the shirt on.

"You don't mind us parking here, do you?" Chloe asked Tyler confidently as she crossed her hand over her bare stomach. Chloe had decided to wear a strapless red bikini without a shirt to cover her up and a pair of shorts.

"Tyler doesn't mind at all." Matt spoke up for his friend who was giving Chloe the evil eye.

"Actually I do." Tyler stated. Chloe huffed. She held out her keys in front of her.

"Matt, do you mind parking my car somewhere else for me?" Chloe asked as she batted her eyelashes. Matt sighed before taking her keys out of her hand.

"Sure Chloe." Matt said. Chloe gave him a genuine smile. He got into her car and backed out the driveway. Chloe turned around and gave Tyler a smirk that spelled victory over her face. She headed into the house, leaving Tyler, Jeremy and Kaitlin in the driveway.

"Let me go make sure the house is still intact." Tyler said before walking off. Kaitlin was just about to follow how when Jeremy spoke up.

"How have you been?" Jeremy asked, hoping things would be okay between her. She turned back to him.

"Good. Things are going great." Kaitlin said. She found it confusing that all of the sudden Jeremy wanted to speak to her, even though he avoided her when she tried to be friendly with him for the past two weeks.

"That's... great. Listen, can we..." Jeremy said before Kaitlin interrupted him.

"You want to talk to me after two weeks of me trying to make things normal between us." Kaitlin declared, a bit upset. Jeremy took in what she said and felt like he was being lectured after getting in trouble. "I should go find Chloe. I'll see you around Jeremy." Before he could get in a final word, Kaitlin walked away.

Kaitlin entered the house and made her way into the kitchen, finding Chloe hanging with a few kids from school. Her friend had grabbed some plastic cups and began pouring a clear liquid into them.

"We're doing shots of tequila! Want in?" Chloe asked as she held out one for Kaitlin. Kaitlin looked at the cup, tempted to do it but she knew how she would get when drinking. She was a hot mess that couldn't be controlled.

"I can't It's too early and I haven't said hi to people I like and don't like." Kaitlin explained.

"It's a party. A celebration party to be exact. You don't drink now, you don't celebrate later. Okay?" Chloe stated as she shook the cup in front of her. Kaitlin eyed it before looking back up at Chloe.

"Fine. One shot and then I go." Kaitlin set her bag down on the counter before grabbing the cup. Chloe handed her a slice of lime and shook some salt on each other their hands. "Bottoms up." Kaitlin said before she licked the salt off her hand. She quickly downed her shot and stuck the lime wedge in her hand. The burn of the tequila was soon balanced out with the sore taste of the citrus fruit.

"Let's go again." Chloe yelled, already feeling the effects of the liquor in her system. Kaitlin rolled her eyes, knowing that she would be coaxed into taking another shot.

After six rounds of shots, Kaitlin decided she needed a break. She walked out onto the deck on the second floor and leaned against the railing, feeling a bit light headed. She looked down and saw Jeremy talking to some friends, smiling and looking happy. Kaitlin sighed, watching him. She liked seeing him like that. She knew he had been through alot with losing his parents and having his aunt Jenna and Mr. Saltzman mysteriously resigning at the school. All he wanted was someone to be by his side. But with all the drama and rumors, Kaitlin wasn't sure if she would be strong enough to deal with of all it.

"Enjoying the view?" Elena asked. Kaitlin turned to her side and saw her standing by her side

"I'm just resting." Kaitlin lied. Elena turned to her.

"You're a very bad liar." Elena said with her head tilted to the side. "You're afraid of him, aren't you?"

"I'm not afraid of... Jeremy." Kaitlin admitted. "I'm afraid of the baggage that comes with him. I think I won't be strong enough to deal with the drama."

"When you care about someone, you shouldn't worry about their past or who people think they are. Just how you feel about them." Elena explained. "I wish things were simple and normal like you and Jeremy could be." Kaitlin looked at Elena confused, seeing her in deep thought. "Just give my brother a chance." Elena said before walking away, leaving Kaitlin to her thoughts.

The sun had set and the dark seemed to engulf the lake house. The many different fires that people has set up along the lake illuminated the area, giving small beach a nice glow in the dark. Jeremy was sitting on one of the logs, messing with a fire that was blaring. He felt the warmth from the fire and the liquor he had consumed. He was currently nursing a red cup with ice and bourbon. Before that, Jeremy had consumed at least three beers, not wanting to over do it. Luckily he was going to be staying at Tyler's over night so he didn't need to drive home.

"Want to light up?" Jeremy heard Matt ask as he walked over with Chloe attached at his hip. Ever since Matt and Chloe started drinking, they had been attached at the hip. And wherever Chloe went, Kaitlin followed. She was trailing behind them, stumbling a bit.

Kaitlin plopped down beside Jeremy on the log, not caring if Jeremy objected to it. Not like he would.

"Yeah. Sure. Do you have a joint?" Jeremy asked as he rubbed his forehead. Chloe was leaning her head on Matt's shoulder.

"Yes. It's in my truck. You want to go get it?" Matt slurred a bit. Jeremy nodded. Kaitlin was messing with the fire, throwing bits of a twig into it.

"I don't want any." Chloe mumbled.

"Good to know because Jeremy and I weren't planning on sharing." Matt teased. Kaitlin huffed and shook her head.

"I want some." Kaitlin spoke up. Jeremy turned to look at her, surprised. "I'll go with you to get it." Jeremy gave he a lazy smile. He got up and looked at Matt.

"Keys?" Jeremy asked. Chloe sat up and dug in his pants, trying to make a show for Matt. She pulled them out and threw them at Jeremy, not taking her eyes off of Matt. He chuckled causing her to giggle. Kaitlin rolled her eyes at their behavior. Jeremy turned to Kaitlin, holding out his hand for her. Kaitlin took his hand and stumbled a bit as she got up. They began to walk away from the fires.

Jeremy and Kaitlin soon found themselves between rows of different cars. For the past few minutes, they were silent as they walked towards where Matt parked his car.

Kaitlin shivered, feeling stupid for agreeing with Chloe to wear a shirt as a dress. She was still wet from swimming earlier that night. Jeremy heard her exhale, her teeth chattering.

"Are you cold?" Jeremy asked. Kaitlin shook her head, not wanting to be a bother. Jeremy began to pull his hoodie off, giving Kaitlin a peek of the tan flesh and little hairs that led down into his shorts. She gasped, feeling herself blush. Jeremy handed her the sweater and Kaitlin proceeded to pull it on.

"Thank you." Kaitlin said softly. They continued walking in silence until they reached Matt's car. Jeremy went over to the door and opened it, climbing in. Kaitlin leaned against another car, waiting on Jeremy to find it. He looked through the glove department in the car.

"You okay out there?" Jeremy yelled, asking Kaitlin. He shuffled through some cds and found the bag sticking out between two.

"Yes, I'm okay." Kaitlin said as Jeremy began to get out of the car. They were close to touching due to the lack of space between the cars. So that's why Kaitlin moved a little closer to him, wanting to feel his chest brushing against hers. "It's a long walk back, you know. I honestly think Matt and Chloe have long forgotten about smoking. They're probably making out by now." She admitted. "How about we stay here and smoke it?"

Jeremy was seriously considering staying at the car with Kaitlin, especially with how close they were to each other.

"That sounds good. Hop in the cab of the truck." Jeremy spoke. Kaitlin gave him a mischievous smile before she began to climb into the cab. She slipped as she tried to find a grip for her foot but Jeremy put his hand on her back, helping get her into the cab. Once she was in, Jeremy got into the cab, causing it to squeak loudly. Kaitlin let out a giggle. "What?" Jeremy asked.

"You're big. The car didn't make any noise when I got into." Kaitlin chuckled. Jeremy swatted her thigh playfully.

"I am not fat." Jeremy laughed. She poked a finger into his stomach. Jeremy swatted at it again, causing Kaitlin to giggle. He moved beside her and leaned against the side of the car. He opened the bag and pulled out the joint. He dug through his pocket and found a lighter.

Kaitlin watched as Jeremy stuck the joint in his mouth and lit it up. He inhaled and took the joint out of his mouth, letting the smoke out of his lungs. He held it out for Kaitlin and she took it, her fingers brushing against his. She held it up to her lips and took a deep drag of it. She held in the smoke before letting it out as she began to cough.

"You okay?" Jeremy asked as he pat her back, helping her get the smoke out. Kaitlin coughed more, feeling embarrassed. She had smoked weed only once in her life and she hated it. But she wanted to let go and relax a bit more.

"I suck at smoking weed." Kaitlin laughed as she let her head lay back on the glass of the car. She banged her head against, letting out a yelp of pain. Jeremy couldn't help but laugh along with her. He took the joint out her hand.

"I'm going to blow you a shotgun." Jeremy said to her. He took a deep drag and held it in before tilting her face and bringing it closer. He blew the smoke out and watched as Kaitlin inhaled it. A moan rumbled from her and he couldn't help but find it incredibly sexy. She was breathing in what he had just inhaled into himself.

Plus Jeremy hadn't done that with anyone since he had dated Vicki. He pushed back those thoughts and looked down, feeling Kaitlin's nose brushed against his. Jeremy looked up and his brown eyes met her blue ones. He was so tempted to lean in and kiss those dark pink lips of hers. Jeremy lifted his hand to her cheek and rubbed the skin softly, helping her relax more. He leaned in to place one on her lips and he met her cheek.

Kaitlin had felt Jeremy's lips on her cheek and instantly regretted looking down. She felt him move away, giving her some room. Jeremy felt hurt that she rejected him. He lifted the joint up to his mouth and took a drag before he felt Kaitlin's lips attached at his neck. She began to suck softly, causing him to shiver under her touch. Jeremy's eyes closed and Kaitlin sucked a little harder, wanting a bruise to form. He led his hand trail up her back and let his fingers get lost on her light brown tresses.

Kaitlin bit lightly into his neck, feeling Jeremy shudder. He took his hand that was free and began to trail it up the back of her bare thigh. It was Kaitlin's turn to shiver then. He chuckled and continued to trail his hands until her got to her butt, feeling them in his hands. He began to massage them, pulling Kaitlin closer to him.

Kaitlin pulled back from kissing Jeremy's neck and pulled off his hoodie. She threw it behind her and let her hands roam over his shoulders. Jeremy took his hand out of her hair and let it join his other hand on her behind. She sat down on Jeremy's lap more and felt his length pressing between her thighs.

"Jeremy..." Kaitlin moaned as she ground her hips against the apparent bulge. Upon hearing his name fall from his lips, Jeremy needed to make her feel good. He moved her from his lap and laid her back on the bed of the truck. Jeremy kissed down her neck and the valley between her breast.

"So beautiful..." Jeremy whispered as he trailed kisses down her stomach. He situated himself between her thighs and started to lick around her navel. He pulled back and looked up at her. "Do you want to..."

"Yes." Kaitlin breathed. Jeremy leaned back on his knees and pulled her bathing suit bikini off, getting a good view of what was underneath.

Kaitlin let out shallow breaths, feeling Jeremy look her over. She wasn't a virgin but she was nervous having Jeremy see her most intimate spots. He leaned down as he rubbed her thighs, trying to get her more relaxed. He leaned down and took the first swipe of her clit with his tongue.

"Oh..." Kaitlin breathed when she felt the electric tingles erupt through her body. Jeremy licked another stripe before pulling back to insert his middle finger inside of her. He found her clit again with his mouth and began to suck it softly while he tapped his middle finger inside of her, finding her g-spot.

Whimpers and shallow breaths erupted from Kaitlin's body as Jeremy led her to her release. She grasped his head, running her fingers through his hair.

Jeremy looked up, noticing the way Kaitlin was reacting to him giving her oral sex. He was use to hearing loud moans of sweet pleasure due to him having been with Anna and Vicki. He had never went far with Bonnie so he didn't know if she made noises when she engaged in sexual acts. But Kaitlin was definitely different. She let out low whimpers and murmurs. He had to listen carefully to her just incase she objected to anything he did. But so far, she didn't, only letting out 'yes' and 'oh'.

Jeremy speed up the taps of his fingers, feeling her inner walls contract around his digits. His lips closed tightly around her little clit, making vibrations. A hard yank from her fingers signaled him that she had reached her end.

Kaitlin swore she could die just from the release Jeremy had gave her. She felt his fingers continue to move inside of her quickly, prolong her release. She just kept coming, feeling one orgasm after the other as Jeremy kept licking it up, causing more sensations to run through her. She clamped her thighs around his head, trying to get him to stop his movements. Her body shook as she calmed down from it.

Finally, Jeremy unlocked her wobbly legs from around his head and got up, pulling his fingers out from her. Kaitlin grabbed his hand that was previously inside of her and proceeded to lick lazily at the fluids that coated her fingers. Jeremy just looked on with a slightly hanging jaw. Vicki and Anna definitely had never done that.

Before Kaitlin even had the chance to dive her hand into Jeremy shorts, a light was being flashed into Jeremy's eyes. She quickly scrambled for her shirt to cover up her naked bottom half.

"Sheriff Forbes?" Jeremy asked as he saw her outline in the dark of the night.

"Jeremy... I'm going to need you and your sister to come down to the precinct. It's... about Alaric." Sheriff Forbes said.


Author's Note: So I decided to give you guys that little smutty treat since you guys have been so amazing and patient with me. I've gotten over 510 hits on this story and it keeps getting better everytime I check to see who has been reading. I would really love if you guys to time out though to review and tell me whether you hate or love this story. So what do you think of Chloe? Does she mean well or is she a bitch? What do you think of the little hook up between Jeremy and Kaitlin? What is going on with Alaric? R&R