I kinda thought it'll be nice to have a chapter about Dean and Avery's relationship before they broke up and when they were younger in their high school life, including Avery's friendships, especially Jenny. So here it it! Hope you enjoy. Tell me what you whole chapter is all flashbacks.

Chapter Five

"We missed you last night." Jenny said to Avery as soon as the dark haired teen sat down in the chair in front of her.

"Sorry." Avery apologized halfheartedly. "Family night."

"Family night beats getting high night?" Jenny raised her perfectly shaped eyebrows. She was tapping her pencil on the desk rather rapidly, her gaze unfocused and a bit red if you looked closely.

"Oh my God you're stoned." Avery laughed quietly. Already the first day of school and her best friend was on her way to failing.

"Of course I am." Jenny hissed softly. "What do you expect?"

"Umm.." Avery pretended to ponder. "Waiting at least for me." At Jenny's confused look, she reached into her bag and got out the thermal cup-filled with bourbon.

"Oh, Aves." Jenny sighed mockingly. "You naughty, naughty girl." She laughed when Avery took a small sip from the cup, her face normal as if she was drinking coffee, though she could see the slight choking she held back from her throat.

"You don't get to talk about naughty." Avery took another sip. "I heard about you and Matt." Jenny opened her mouth to speak. "And Finn and-"

"Alright. I get it." Jenny said. "But they weren't at the same time." Avery hummed in response, clearly unconvinced.

"Guys!" Angela, one of their friends waved before sitting in the chair next to Avery. "Did you hear?"

"Hear what?" Avery exchanged a glance with Jenny.

"There's a new guy." Angela informed them excitedly.

Avery groaned, dropping her head to her desk. "This is just like every teen movie ever made."

"New guy-" Jenny continued for her. "plus girl. Fall in love-"

"-beat the impossible-"

"And live happily ever after."

Angela huffed, brushing her short flaming red hair out of her face. She was probably on of the prettiest girls in their class. Emerald green eyes and full pink lips and her pale face covered with adorable freckles, she was quite tall as well, gave boys a run for their money. She only dated jocks.

And the, Jenny, with her shoulder-length curly blonde hair and light green eyes, and a personality that attracted boys from two towns over. From what Avey gathered the years they had been friend, the blonde prefered bad boys; who eventually break her heart.

Avery always felt plain and average in their presence. Her awkward hair, dark brown that reached just past her chin. Her eyes were hazel-and from what her mother says; with flecks of gold. Average height, average personality, average everything.

They had a fourth friend: Lori. Lory was the closest to Angela, both of them practically had the same taste in everything, including guys. She was late today, the girls guessed it was because of her current boyfriend, Lance-who didn't by any chance meet her friends' approval.

"You're so bitter." Angela said. "You're never going to find a guy with that attitude."

"Well, the. I guess it's a good thing I'm not looking for one." Avery smiled fakely at her friend. Their conversation stopped when Lori entered the classroom, followed by Lance, both of them laughing.

"Great." Jenny rolled her eyes. "Here comes the best friend stealer." She said as Lori sat in her usual chair next to Jenny, Lance automatically sitting in front of her.

"Hey guys." Lori smiled brightly.

"Lori." Avery greeted, being the only one mature in the group. "Why're so late?"

Lori smiled guiltily and glanced at Lance. "We got carried away." She admitted.

"Okay!" Jenny suddenly burst. "Ew." She looked absolutely disgusted, she leaned and grabbed Avery' thermal cup out of her hand and took a large sip, gulping the liquid down.

"Is that…?" Angela pointed at the cup, Avery nodded in reply. Angela grinned and reached down to her own bag and got out a Starbucks plastic mug, fully covered with a black straw.

"What do you got?" Angela asked.

"I snatched a bourbon bottle from my dad last night." Avery whispered so other students wouldn't hear.

"You're so lucky." Lori told her. "I tried to get to the liquor cabinet a few days ago and my mom caught me."

"What did she do?" Jenny questioned.

"Nothing." Lori answered. "I told her I was getting it for dad. Didn't even think twice about letting me go." Her parents were well on their way to divorce, fighting all the time. She mostly stayed at the other girls' houses.

"They're still doing that?" Angela said. Lori nodded, her happy facade cracking a bit but went right up when Angela offered her her cup.

"This year is already up for a bad start." Jenny declared just as the teacher entered the room, a stern expression on his face.

"Okay. Okay." Jenny breathed in front of the mirror in the girls' bathroom. "Okay." She applied her dark lipstick. "Okay."

"What the hell is wrong with her?" Avery asked as came out of the bathroom stall.

"She's working up courage to talk to the new guy." Lori informed her as she adjusted her black hair.

"Never thought I'll see the day when Jenny Forbes turns shy." Angela mocked from her place besides Avery, she too reapplying her makeup.

"He's cute." Jenny explained simply.

"Oh guys, I heard Cindy in French earlier." Angela said. "It was absolutely hilarious. She kept going like 'he's so hot he's not even real!'."

"The fuck?" Jenny mumbled. "She has a boyfriend."

"No, she doesn't." Avery entered the conversation, she hesitated at the attention of the three girls on her. "I saw them fight earlier." She said. "Then I saw Cindy making out with Jamie."

"Moving on already?" Jenny said.

"Look who's talking." Angela put everything back in her bag, she slung it over her shoulder. "I can't make lunch today. Gotta make up for English quiz."

"See ya." The girls mumbled goodbyes. They all eventually spilled out of the bathroom one by one. Lori, with the excuse of the meeting up with Lance, Jenny went to the library where she head from one of the girls in the hallway the new guy was studying.

"Seriously, guys?" Avery asked out loud. She was the only one left in their group. She made her way alone to the cafeteria. Mentally debating who to sit with, there was the guys they hung out with, but she never went to them without Jenny or anyone else. By the time she reached to doors, she had decided to take the food and eat in her car.

She bumped into someone, slamming her forehead against a hard surface. "I am so sorry." She apologized softly without looking up. "I wasn't-"

"It's fine." She tilted her head up to meet unfamiliar brown eyes. "I was the one absorbed in this." He pointed to the book he had in his hands.

"A tale of Two Cities." Avery read the title aloud. "A Charles Dickens fan?"

"It's my favourite." The guy said. "You?"

"Oliver Twist." She answered. "We don't get a lot of Dickens fans around here."

"And why is that?" He asked.

"Because it's a not a required reading." Avery said.

"Well, I think everyone should at least read one Dickens story in their lives." He said. "I'm Dean by the way."

"Avery." She smiled shyly.

"Oh." Avery walked between the library shelves. "This." She pointed at a book. "And this." Another book. "And this. Definitely this."

"You're almost as obsessed as I." Dean commented, stopping briefly to read to the titles of the books she pointed out.

"Ha." She said mocked. "That's impossible. You should see my room." Her cheeks turned red when she realized what she said.

"You should see mine." Dean took a step closer to her, a grin on his face. It faltered when she laughed. "That came out totally wrong."

"Yeah." He agreed before clearing his throat. "What about this one?" He reached over her to one of the higher shelves and got a book out.

"The Death of Virgil." Avery said. "No, I haven't."

"Trust me." Dean handed her the book. "It's worth it."

"I'll make you a deal." She said. "If I read this, you're going to have to read a book I recommend."

"Hit me with your best shot." The school bell rang, making Avery quicken her thought for a book.

"Oh!" She snapped her fingers. "I have the perfect one. Changed my life." She hurried between the aisles searching for it.

"Almost every reader said that about every book they read." Dean's voice came from behind her.

"It's true." She leaned forwards on her toes to reach it, she gave it to him, a satisfied grin on her face. "Red Badge of Courage." She announced. He examined the cover for a few moments before holding his hand for her to shake.

"I'll get back to you in a couple days." He said. "You finish my book and I'll finish yours. Deal?"

She glanced at the awaiting hand, and almost shyly, shook it. "Deal."

"This has got to be like the most stressful day of this year." Jenny groaned, taking a large gulp from the whiskey bottle she stole from her house.

"We've only been in school for a week." Avery took the bottle from her hands to sipped from it. "What can you possibly complain about?"

"Boys." Jenny said in a 'duh' tone. "Someday." She snatched the alcohol back. "Someday, young, little Avery-" She rolled her eyes at that. "You'll find your guy and know what the rest of the world is experiencing."

"Yeah." Angela slurred a bit, "You don't you have a boyfriend. Everyone-" She pointed at the general area around her. "Has one."

"I don't." Kyle, one of the guys raised his hand up.

"Kyle." Jenny spat out the name. "God, I fucking hate Kyle. Why are we talking about him?"

"He's sitting-" Avery was cut off by Jenny.

"We're talking about you." She poked her hard in her stomach. Avery turned around and mouthed 'sorry' to Kyle, who shrugged and mouthed back 'it's okay. I hate her too.'. She refrained from smiling at that. Jenny and Kyle were so much alike, and he was about the only guy she hasn't hooked up with in their group, when she had said that, Jenny had said 'yet.' Taking the rejection as a challenge.

"Am I at the wrong place?" A voice asked. Avery looked up to see-to her surprise: Dean.

"Dean." She said. "Don't tell me you joined the 'bad crowd.'"

"I didn't know you're a part of it." Dean slowly stepped in the large room. They were a their standard hangout place, an abandoned house not far from school. The small house was trashed with their junk and empty liquor bottles lying on the ground.

"So what?" Avery stood up, feeling liquid courage run through her veins.

"I like a girl who can handle her liquor." Dean said.

"This isn't the place to look for girls." She slid past him and took one of the many bottle, without looking at the label, she drank from it. Tequila, she grimaced as it burned her throat as she swallowed.

"Good. 'cause I'm not looking for one." He grinned and held a hand out. Avery tilted her head to the side, the alcohol delaying her reaction as she realised he wanted the bottle, she wanted it to him, watching his reaction closely as he drank it like water.

"Is she okay?" He pointed Jenny, who was sitting up against the wall, her arm at an awkward angle as she leaned her head on it.

"She's fine." Avery waved him off and took back the bottle to take her seat on the floor again. He sat down on the opposite side of her, the wall weren't far from each other, so with his long legs, he easily reached her wall while sitting up.

"I didn't know you drank." She said as she watched take a pack of cigarettes out of his pocket. "And smoked. Anything else you do?"

He got out a lighter and brought the cigarette to his lips, lightning it up and taking a long drag from it. "A lot of things."

Dean opened the door for Avery as they entered the school, their hands intertwined.

"Are you sure about this?" Dean murmured softly in her ear. "We could longer if you're not comfortable."

"I'm positive." Avery squeezed his hand. They headed to his locker first since it was the nearest, people stared as they walked together; the newest couple in school.

"This is so weird." She commented as he got his books out. "I never had so much attention on me before."

"Why is that?" He asked, closing his locker and taking her hand again.

"You know the other girls I hang out with; Jenny, Lori and Angela."

"Wait, Angela is the.." He tried to remember. "The annoying one."

Avery chuckled and nodded. "Yeah, and Lori is the one with the black hair-"

"And that guy breathing down her neck." Dean continued for her.

"He's almost as overprotective as you." She teased, she hid her yelp when he suddenly threw his arm around her shoulder and pressed a kiss to her forehead.

"I like to take care of you." He said, she looked to the ground, hiding her blush. "Hey." Dean muttered. "You don't have to be shy around me."

"Who says it's just you?" Avery questioned.

Dean shrugged. "I've only been in this school for a month. I haven't picked up on everything." She hummed, knowing he was observant even if he didn't mean to, he spent two weeks around her and managed to know things not even Jenny knew about.

"You think I'm lying." He said. They stopped in front of her locker, noticing Jenny on the other side of the hallway, chatting with Lori.

"No." Avery denied, getting out her Chemistry textbook and her backpack. "I'm just thinking you're not telling the whole truth." He raised his eyebrows in questioning. "One week .One week and that's all it took you to know almost everything about me."

"Well, there's something you didn't pay attention to." He took the books from her. "It's you I noticed, not anyone else."

"I'd say creepy, but it's sweet." She said. The bell rung, signaling they had to part for their classes since they were different grades.

"See ya at lunch?" Avery asked.

"What's your schedule?" Dean said, she opened her locker wider to show the piece of paper taped to it. "I have free period in the same time you have P.E."

"Great." She leaned forwards on her toes to peck him. "Then we'll both skip."

"What is this I hear about you and Dean?" Jenny demanded as soon as Avery sat in their shared desk at Chemistry.

"What's what?" Avery said. Jenny rolled her eyes heavily and gestured impatiently. "We're dating."

"Seriously?" Jenny's eyebrows raised to her hairline. "Since when?"

"About a ten days or so." Avery admitted sheepishly.

"And you didn't tell me?" Jenny questioned.

"Jen." Avery sighed, hiding her smile, these last days had been the happiest in a while. "He's my first boyfriend and I'm really nerv-"

"Say no more." Jenny stopped her from talking. "I get it." She said dramatically.

"You do?" Avery said, feeling skeptical.

"I went through the same thing with my first boyfriend."

"Jenny, that was like the fifth grade or so." Avery said.

"The seventh." Jenny corrected her. "Anyways-" She suddenly smirked widely. "I want to know all the dirty details."

"Nothing happened yet." Avery said. She stopped talking when the teacher entered the classroom, though Jenny didn't seem to care as she continued.

"Well, good luck with him." Jenny said. "You two seem perfect for each other."

Avery and Dean lounged in her bedroom. The house was completely empty of its members except her. They had gone out of town for some reason she didn't even bother listening to as she instantly used the excuse of it being her senior year and that she needed to study. Her parents, happy to see her work hard for school, left her behind.

"What the hell does this even mean?" Avery frowned. She was working on math, her worst subject followed by science.

"Show me." Dean got up from the chair she kept beside her window and climbed in the bed, shifting himself so he was behind her. He grabbed the notebook and looked over the problem. "I remember this."

"Really?" She asked, thinking that she was finally getting a chance to understand it.

"Yeah," He nodded, before throwing the paper aside, "I flunked that part in the test." Avery groaned, throwing her head back to Dean's chest. His arms came around her waist, pulling her so she was sitting between his legs. He pressed a feather-like kiss to her shoulder, smirking at the shiver that ran through her. "Maybe you should take a break."

Without waiting for her to respond, he crashed his lips to her fiercely, his hands cupping her chin and deepening the kiss. Avery held back a moan when he parted her lips to enter his tongue. She broke the kiss to straddle him, sitting in a position they never tried. She tried to slam her lips against his again but he pulled away.

"It's okay." She murmured softly, running her hands lightly over his chest. "I'm ready."

"Are you sure?" He gulped. It was obvious he was resisting to comply with her and flip them over. "I don't want to pressure you. I can wait-"

She kissed him, cutting him off. He apparently lost whatever was holding him back and flipped them over so she was under. He softened the kiss, his lips pulls were slow and passionate. Avery's hands reached to tug his shirt, trying to get it off. Dean chuckled, pulling away to throw it back into the room, he connected their lips together at the same time as he took off her own shirt. Her hands shuffled to unbuckle his belt and pants, kicking them off his feet.

Avery wiggled out of her shorts, there was one moment when they both pulled away and sat up, panting heavily and staring at each other. He was only in his boxers and she was in her underwear set. Plain cotton, pale pink. She blushed when some clearness came back to her head. She tried to pick up the quilt to cover herself, only to be stopped by Dean's hands clamping around hers.

"Don't." He said. His voice was deeper and huskier than she had ever heard. "Don't hide from me." He let of her hands, she kept them at her sides this time. Her face blushed brighter when he sat up on his knees, his eyes observing her. Insecurities ran through her head.

"God, you're beautiful." Dean muttered, he leaned to kiss her again, his hands lifting her up a little to unclasp her bra. She closed her eyes when he stopped kissing her lips and moved to trail kisses down her neck until he reached her stomach. He didn't rush, none of his actions were urgent. He took his time laying sweet kisses all over her body, not leaving a spot untouched.

"We can still stop." He whispered against her skin, stopping just above her panties, his eyes connected with hers to show the genuine emotion in them.

"No." Avery said. "Go on." He kept his eyes connected with hers as he smoothly slid down the only piece of fabric on her body. His eyes questioning. He pulled back to lift the covers over the both of them.

"If it's too much, or anything. Tell me to stop, and I'll stop." She closed her eyes, anticipating the pain she knew was bound to come.

"I wanna try something." Dean murmured. "To help you a bit." And with that, he lowered his head between her legs. She breathed sharply when he laid a kiss softly down there before his lips met her foldes and began licking slowly and gently. She moaned at the new and strange sensation, he took that a sign to keep going as he sped up a little, his tongue entering her.

Avery had experienced anything like this, sure she had gotten a bit curious but never really did something. She was half sure she would grow up to be the single old lady who raised cats alone. Jenny was always the one to get the guys, Lori probably had the sweetest boyfriend that ever existed and Angela was content with casual flings.

"How does that feel?" Dean whispered, sending vibration all through her body.

"G-good." She breathed. "Dean, I-" She felt a pressure rise up but stopped when he pulled away. He was breathing heavily almost as much as she. She heard him clumsily reach down for his fallen pants and a faint crackle of foil as he put on the condom. She closed her eyes as he pressed a kiss to her lips, then forehead before positioning himself at her entrance. She gasped, making him still.

"Go on." Avery turned her head to the side to bit into the pillow to muffle her gasps as pain shot right through her. He went in all the way, clearly holding back as his body was shaking, including his hands as he cupped her face and kissed her deeply, trying to distract her from the pain.

"It's okay now." She said quietly when she felt a shift and pleasure flooded in her body. Dean buried his head in her hair and thrust deeper. She held onto his shoulders as he sped up and went much faster and harder. He wanted to last longer than her, his movements turned sloppy as her world exploded, he shuddered right after her, breathing heavily.

He pulled away, she watched him as he went into the connected bathroom of her bedroom to get rid of the condom and went back to her.

"Did I hurt?" Dean said as he picked his clothes again.

"No." Avery said, she pulled the covers over her chest to hide herself. "You were perfect."

"So it was good." She could see his smirk in the faint light, he leaned forwards to connect his lips with hers gently. She nodded after he broke away from her to hand her back her underwear, climbing into the bed again, he wouldn't have gotten up if it wasn't for the fact he knew she was shy about her body and physical contact.

"But seriously." He pulled her to his chest to lay her head on his bare skin since he hadn't searched for his shirt. "If you feel any-"

"Dean, I'm fine." She traced a circle on his skin. "It felt good."

"One time thing or good enough to do it again sometime?" He asked.

"Definitely again." She said. "Maybe even very soon." She pressed a kiss to his neck.

"Let's wait a few days." He said. "How long until your family comes back?"

"Monday." She grinned, it was Friday, they had all weekend to themselves.

"Perfect." Dean lowered his head to kiss her.