This idea has been stuck in my head for ages but I've never had the courage to put pen to paper...so here goes! Wish me luck and enjoy! ;)

Rough idea of what Deanna (pre-crossdressing) and Cassie look like: art/Girls-Will-Be-Girls-457609374

Chapter One

It was the summer of 1959. The sizzling asphalt became viscous in the peak heat of the afternoon sun. July had passed, moving on towards high summer; sweaty faces, buzzing flies and sweltering heat became the norm. Deanna lay sprawled on the freshly cut grass of her parents' yard in her boot-cut pants and white shirt, occassionally taking a swig from her bottle of cool coca-cola. Now, this is what she called a relaxing Sunday afternoon. However, this didn't distract her from the gnawing fact that she was completely and utterly bored. There was nothing to do on days like these. Well, nothing that she enjoyed and was allowed to do. Her so-called friends were gossiping about boys and trying on each other's dresses over at Lisa's house. Well, she didn't know for sure that they were but it was a pretty good guess as it was something they did quite often.

Deanna lifted up her hand to shield her eyes from the beating sun as a shadow emerged, interrupting her thoughts as it towered over her. It was Joe Harvelle, her boyfriend. Everyone was jealous of her because of it. Joe was the school's rebellious jock. Most of the time he wore his cuffed jeans, leather jacket and greased back hairsyle. It was completely outrageous, especially because they'd recently banned denim in their high was one of the things she found attractive about him. However, because of the suffocating heat, he'd left his jacket at home, donning a white vest instead.

"The guys are gonna go play some baseball, you don't mind if I join 'em do you?" he asked, looking down at her.

"No, 'course I don't mind. Can I come?" Deanna asked, picking herself up off the ground and dusting herself off.

"Oh sure, a cheerleader would be great for team morale." he nodded, raking a hand through his dirty blonde hair.

"No, I mean to play."

Joe tilted his head to the side, a look of confusion crossing his features before he burst out in to a fit of laughter. "For a second I thought you were being serious." he answered, his smile still present.

"I wasn't joking." Deanna said, folding her arms, her brow creasing in annoyance. It wasn't like she was terrible at the game, she was actually pretty good, not that they'd seen her play. Deanna believed she'd make a great addition to the team.

"Look, we've been over this before. Sports aren't for girls...it's a guy thing. Men are physically stronger...they're made for it, that's just a fact."

"That's rubbish. I'm better than half of the the boys on your team."

"Really? Then maybe I should alert the media...?"

"Get bent." Deanna spat, surprised by what she'd just said. If anyone else had heard her swear she'd have been in big trouble. Then a thought crossed her mind, did she really care? She was fed up with being treated like a lesser being just because she had boobs. Life was totally unfair. Sometimes she wished she'd been born a boy. Things would have been so much easier and maybe she could have had the chance to enjoy her life a little more instead of feeling like a bird trapped in a cage.

"Excuse me?" Joe exclaimed, raising his eyebrows, staring at her in shock.

"You heard me. Get out of my house." Deanna growled, folding her arms across her chest, her irritation increasing by the suffocating heat of the blazing sun.

"Are you being serious? What did I say?" Joe said, looking more than a little upset.

"Hey nosebleed, did I stutter? I told you to leave." Joe took out a cigarette and lit it, inhaling the smoke then exhaling through his nose, trying to act casual about the whole thing.

"Fine but don't come crawlin' back to me when you feel like you want me back, 'cause I won't be there." he replied, shaking his head as he walked over to his sleek black motorcycle.

Once he'd left, Deanna had no idea that it was going to be the last time she'd ever see him. Yelling in frustration she stormed in to the house and ran up to her room, slamming the door. She was glad her parents weren't there at the moment, seeing her like this. They'd have probably told her it was completely 'unladylike'. Her screams soon became sobs, until finally she fell asleep in to her tear-stained pillow.

When she awoke, the sun had almost set and she could feel the cool breeze seeping through the partially open window. She sighed and rubbed her eyes which were swollen from crying. Grabbing the magazine on her bedside, she flicked through it, partially interested by what the columnists had to say. However, she soon came across a review for a new movie called 'Some Like it Hot' featuring Marilyn Monroe. She looked as beautiful as ever but what really caught her attention was the comedic pair Tony Curtis and Jack Lemmon who were dressed head to toe in female attire, makeup and everything. Could she...? Should she...? Deanna jumped out of bed and glanced at her reflection, holding up her cascading golden locks so that it appeared as if she were a boy. The sight tugged the corner of her mouth in to a small smile. "Well hello, Daddy-o." she grinned. Then opening up her stupid sewing kit that she used for her home economics class at school, she grabbed a pair of scissors. Looking down at them nervously, her hand shook slightly. If she did this, there was no turning back. She could feel her heart beat painfully in her chest from nervousness. "Oh God." she muttered. Then taking a deep breath, she began to hack away in to the girly mop of hair on her head. After tidying it up a little, the pixie cut looked half decent, it actually kind of suited her. "Not bad." Deanna grinned.

Raking her hand through her hair to muss it up a little, Deanna pulled open her wardrobe and collected up all the preppy skirts and dresses... which to be honest was nearly her whole wardrobe. She then dumped it all in to a garbage bag so that she could sell them in bulk.

When Deanna came back in the evening, she'd spent the money she'd earnt from the clothes to buy a pair of cheap jeans and pants, two men's tops, a jacket, underwear, a pair of shoes and shades to name a few. She knocked on the front door and it was her little brother Sam who'd opened the door. "Deanna?!" he exclaimed in shock. "I'm telling Mom!"

"That's my name, don't wear it out." she muttered under her breath, rolling her eyes as she took a step inside. Her brother could be so annoying sometimes.

"Mom! Mom! You have to see this!" Sammy yelled, running in to the kitchen.

A few seconds later, Mary was pulled from out of the kitchen to see what all the commotion was about. "Oh Gosh." she exclaimed, staring at Deanna in shock. Once the surprise wore off, her mother commented, "It's actually quite sweet, darling. Very modern. The style reminds me of Audrey Hepburn."

"Really? You think so?" Deanna replied, a small smile playing on her lips. Her mother had always been kind like that. Then a thought occured to her. "Remember when I argued with you yesterday? I'm sorry...I think I've actually come around to the idea. I think it'll be good for me to have some change." she explained, tucking her hands in to her pockets. "Oh, wonderful! I knew you would. Staying at your Uncle Bobby's place really isn't that bad and the high school there has a great education system. It'll be a great experience for you and your brother...not to mention, it'll give us the space to let your grandfather stay here."

First day at the new high school (Senior year)

"Hurry, Deanna! We're gonna be late!" Sam yelled from the bottom of the stairs. Deanna was always the late one. Not because she took long showers or anything but because she didn't wake up until past the last minute. It really annoyed Sam because he hated being late. iEspecially/i on the first day of school.

"I told you to call me Dean, now!" Deanna yelled from the top of the stairs. She was having trouble hiding her...boobs. She hadn't really thought about it until now but she had to make it look like she was flat chested (which was going to be quite hard as she had a large pair of...yeah okay). Eventually she found some bandages in Bobby's emergency first aid kit and wrapped them around herself and fortunately, it did just the trick.

"This is so crazy. People are gonna find out." Sam called, genuinely embarrassed by the whole ordeal. If his classmates found out about his sister, he wouldn't live to see the next day. He was surprised Bobby was fine with the whole thing, to be honest. He'd said if that's what Deanna wanted to do then who was he to stop her? They didn't tell their parents though. They thought it would be best to keep it quiet.

After another three minutes and 42 seconds (Yes, Sam counted!), Dean made her...his way downstairs. "How do I look?" he said, waggling his eyebrows. He was wearing the classic greaser look, shades included.

"Stupid." Sam retorted, sticking his tongue out, not wanting to admit that he looked pretty badass.

"What would I do without my little brother?" Dean joked, giving him a noogie, causing him to yelp.

"Stop! And I'm not that little."

"I disagree. 14 is basically still a baby." Dean teased, offering him a big grin. "Right. First day of school, let's get this show on the road."

They stepped out in to the crisp September air, feeling the last of the summer sun brush against their skin. Dean was still excited beyond belief that Bobby was letting him drive his 59' Chevy Impala. It was the newest model and boy was it a beast. He had no doubt they'd be jealous of it at their new high school. However, he was still nervous about taking it for a spin as he wouldn't be able to pay for the repairs and Bobby would never forgive him. Opening the door to the driver's side, he climbed in and waited for Sammy to get in before they began their 5 minute drive.

Dean pulled in to the student's parking lot and parked, double checking his appearance in the reflection of his shades before sliding them back on. By the time he had clambered out of the car, Sam had already gone to the otherside of the school, worried he was going to be late. Sometimes Dean wondered if they were even related they were so different. Smiling to himself, he slammed the door shut and trudged in to school, watching for people's reactions. As he walked through the front door, it was then that his nervousness hit full force. What if people knew straight away that he was a girl? What if he was expelled for students accusing him of being queer? He ignored his increased, painful heart rate and the sweat that had accumulated on the back of his neck and focussed his attention on finding the main reception.

He finally found it and offered a small smile to the old lady behind the desk. "Name?" she said, adjusting the antique glasses at the end of her hooked nose.

"Dean Winchester." he answered without hesitation which was when a girl roughly his age tiptoed in to the room, looking all shy and timid. She had shoulder-length black hair with bangs, startling blue eyes and a pair of cute glasses settled on her button nose. Her attire was nothing out of the ordinary, a knee-length cream plaid skirt, a navy shirt and headband. She looked like your typical straight A student.

"Okie dokie. You're gonna have to take those shades off when you're in the school building though, son."

"No problem." Dean replied, taking them off obediently, hanging them on the collar of his shirt, revealing his warm and inviting green eyes.

"And here's your timetable and locker number. Now you best hurry or you'll miss your first lesson...which is Spanish." the woman said, adjusting her glasses for yet another time.

Damn. Dean was terrible at Spanish. He'd never really paid any attention in his past school because the teacher was just SO boring. He'd even fallen asleep one time and was sent home for it. Looking back at it though, it was kind of funny. "Thanks, m'am." he said, taking the items. Glancing at the clock on the wall, Dean turned to leave, not giving a second glance to the quiet girl in the corner who was hugging her textbooks close to her chest, waiting to receive her new timetable next.

Spanish class

Dean quickly serveyed the room and saw that there were three seats left. Two at the back and one at the front. He elected to sit at the desk by the window in the back row. Much to his surprise, the girl from the main office took the seat beside him. He hadn't thought he was going to see much of her. "Hey." he whispered, offering her a small, welcoming smile.

The girl turned to face him, a look of confusion crossing her features like she was surprised that he was talking to her. "-Hello?" she replied timidly.

"Name's Dean." he added.

"Cassie."

"Nice name, suits you."

"You think so?" she said, tilting her head to the head slightly. This new guy was strange. Greaser guys, or the 'cool' kids never really gave her much notice. She'd just come to school everyday, participate in the lessons and leave, not really talking to anyone. They always thought of her as a geek because of her passion for learning and reading. Maybe he was only talking to her because he hadn't figured out what she was yet. Cassie placed her textbook, notepad and pencil on the desk just as the spanish teacher glided in. She was a curvy hispanic lady who appeared to be in her mid-thirties. A wolf whistle was heard from the middle row which earned a couple of giggles from the class.

"Settle down, class." the teacher ordered as she turned around to write down her name on the chalk board. "Me llamo Señora Cruz...and as today is the first class, you're going to do some easy speaking practice with the classmate beside you. Okay, let's go." she instructed, taking a seat as the class began to talk with each other. Cassie glanced at Dean who sighed as the announcement was made.

"Let's get this over with." Dean said, turning his chair to face her. "Just so you know I can't speak Spanish to save my life."

"Está bien. Te puedo ayudar."

"I have no idea what you just said."

Cas laughed a little and shook her head. "Alright, how about we start simple. ¿Cómo te llamas?"

"Dean?" he answered, his expression doubtful.

"That's right." she grinned, adjusting her glasses. "Now you try."

"¿Cómo te llamas?"

Cas cringed at the pronounciation but didn't mention it. "Me llamo Cassie."

"Do people call you Cas for short?"

"No."

"Can I?"

"I guess."

"Cool."

"Right, let us try something harder..."

"You mean above pre-school level?" Dean grinned.

Cas giggled. "Maybe...I wouldn't want to challenge you."

"Ohh!" he said, feigning a look of hurt. "How could you?" he joked.

"¿Cuántos años tienes?"

"Sí, porfavor?"

"Close." Cas grinned.

"Really?!"

"No."

"Oh." Dean pouted.

"I asked you how old you were."

"Ah...soy ochenta."

"You are the number eighty?"

"Oops." Dean cringed.

"I think you mean 'Yo tengo dieciocho años."

"Prob'ly. It's no use...my spanish vocabularly is very limited. I know fiesta and siesta."

"Because those two things are very important."

"Exactly! Someone who understands me."

Cas smiled softly, her eyes locking on to his. She swallowed nervously and said "You know...if you ever need a tutor or anything...I'd be glad to help. It would also help me with my revision."

Dean raised an eyebrow and pondered for a moment. "Sure, I'm up for that. I wouldn't want to have to repeat the year." he replied, eyes locking on to hers.

Cas quickly averted her gaze, her face flushing slightly as she gave him a small shy nod. "Great."

To becontinued...