Author's Note: Greetings everyone! It's been awhile since I've posted anything up and this story has been floating around in my head for awhile, especially after my interest in the show has heightened. Anyways, hope you all like it and bear with me since this book in particular is like a giant filler if that makes sense. It's also (to the best of my ability) written in 3rd POV. Hope it's enjoyed and look out for an update next week. Please don't forget to rate/review and all that jazz, ta-ta for now! =)

Disclaimer: I don't own anything related to the show Supernatural, just the story I came up with and the OCs.

Chapter 1

Sam and Dean Winchester were currently driving down a long stretch of road in the backwoods of Virginia after having just destroyed a den of vampires. The sun was setting, signaling the end of the day, and both men were dead tired. They were a few miles outside of Charlottesville waiting for the next hotel to appear and by the next morning, they'll be gone, onto the next case while they awaited any alerts from their father, John Winchester.

A steady silence took over the inside of the '67 Black Impala as Dean drove and Sam searched through news articles, looking for anything supernatural or out of the ordinary. Various buildings and shopping centers popped up beyond the horizon the further they drove and a sign advertising a college basketball game at the nearby university that week flashed behind them.

While Sam was more than willing to crash and sleep for the night, Dean on the other hand was itching for a drink having not had a taste of liquor in a few weeks. He hoped that along with a hotel there was a decent bar nearby.

"Up in Baltimore, there seems to be a string of disappearances from a handful of counties. All of them teenagers, but no other distinct patterns have been linked. A couple are from foster homes, another from a respected neighborhood-" Sam went on.

"Teenagers run away all the time, you did," Dean interrupted cheekily, glancing at his brother who rolled his eyes in response.

"Five in the last month alone Dean and they had promising paths ahead of them. What would make them run away?" Sam asked.

"Well, what made you run away Sammy?" Dean countered.

Sam sighed, "it's along the way, could it really hurt to check?" Sam asked softly as Dean turned into a parking lot. Letting the engine run, Dean smirked when his eyes spied neon lights on the other side of the parking lot, hypnotizing him.

"Let me have a drink tonight and we can check out whatever place you want tomorrow Sammy," Dean grinned. Sam followed his gaze and shook his head.

"Gimme a card so I can check in then," Sam said with his hand outstretched not in the mood for a drink. Dean grinned and tossed a random card before shutting off the Impala. Getting out, Dean headed towards the direction of the bar.

"Dean!"

"Yeah?"

"Keys too," Sam stated with his hand open.

"Seriously?" Dean huffed and Sam just gave him a look that said it was non negotiable. With an exaggerated sigh, Dean pitched his keys, and turned away without another word.

A bold neon red sign that read 'Vertigo' loomed ahead. Loud music boomed from the place and groups of people scattered about. The bar itself was a hole in the wall, but at least it was spacious.

On the right side of the entrance, bar tables and stools were set around a raised stage and a small dance floor. To the left side was a blocked off room that marked a smoking section. Near the middle, three pool tables were placed, all taken, while a long bar stood against the back end of the wall where Dean pushed to first.

Flagging down a bartender, Dean placed a well deserved drink order. "Shot of Jack and a pint of whatever you have on tap," the bartender nodded and took a few moments with the order. Dean slapped a twenty on the counter just as the drinks were placed before him. Dean downed the shot and winced, letting out a breath. Before he could order a second shot, commotion at the nearest pool table made him turn.

Roughly ten people crowded around the table nearest to Dean, shouting and cheering. Craning his neck as the crowd cleared, Dean's jaw dropped. A very shapely female leaned halfway across the table to shoot. She was wearing black PVC pants that clung to her like a second skin and outlined a very full backside. A form fitting black tank top peeked beneath a long sleeved flannel that was tied around her waist.

Dean gulped as she turned and he got a glimpse of her face. Her face was heart shaped with an angled chin and a rounded nose. Freckles dotted her face and highlighted her high cheekbones. On the right side of her face, however, a thin angled white scar trailed from just under her eyelid to the corner of her mouth

But even something as minor as a scar didn't distract from her immense beauty. Her long copper hair blocked the other half of her face as she took the last shot, but Dean could make out a smirk on her plump red lips and fire in her dark eyes.

A loud roar of voices erupted around the table, breaking Dean from his heavy observation. The female smiled as she went around the table collecting bills from others, some either happy or angered by her win. A few slapped their bills on table and shuffled away as she collected her winnings.

Grinning widely, she faced a final patron, hand outstretched. The burly man standing across from her however didn't seem too eager on giving up the wages. He crossed his arms, shaking his head at her, not budging.

The female rolled her eyes, "c'mon Joe, you know the rules, don't be a sore los-"

"No! Every game, you win! Whether its billiards or darts, whatever it is, you magically win it!" The man growled, leaning in to grab her. "If I didn't know any better, I'd say you were a no good dirty cheater,"

The woman glanced down at his hand on her arm then back at his face, no smile was left on her face. "Joe, remove your arm. Now." She said in a low tone.

He scoffed at her, "or what?!" He spat. Dean was close to stepping in, but before he could, the woman took control of the situation. She cracked her neck then grabbed his arm and spun him before slamming his body to the table. Twisting the same arm behind his back, she had him pinned.

He squealed and squirmed in her hold as she moved to whisper in his ear. He went still before letting him free and then stepped away. He swallowed as he dug into his pockets. After emptying wadded bills onto the table did the man turn away and exit the bar without another word. Breathing deeply, she counted the wadded bills along with the others.

Looking around at the remaining patrons, her smirk was back as she raised her arms. "Drinks on me!" She announced happily as they each murmured amongst themselves before going back to their own business. Shaking her head, she headed to the bar while he continued to shamelessly stare her down. He was becoming more and more impressed by this mystery woman with each passing moment.

"Hey Earl! Can I get a whiskey sour shot please?" She called out. Her voice was rugged yet gentle compared to harsh tones moments ago. And Dean wanted to hear more. Clearing his throat, Dean was ready to lay on his charm. "Unless you plan on buying me a drink or challenging me to a game, hold those words." She stated, shooting Dean down.

Dean's jaw dropped as she downed her shot (without a chaser or a hint of discomfort) and turned to face him. Now he could see her eyes. They were almond shaped and chocolate brown, bright and alive. She quirked an eyebrow at his expression, waiting. Dean cleared his throat again, standing at full height. But when he opened his mouth, nothing came out.

"Cat got your tongue honey," she smirked.

Regaining his composure, Dean scoffed. "You were quick to shoot me down weren't you sweetheart?"

Her smirk deepened, "so you weren't planning on laying down a cheap pickup line about how you should bed me?"

Dean scoffed and chuckled, "Of course not!" He sputtered, taking a long sip of his beer.

Leaning in, so close that she could take in his musky scent and Dean in turn got a closer look at the beauty before him, she spoke ever so softly, "then what were you gonna ask me?"

Dean gulped then glanced over at one of the pool tables. "I wanted to show you a thing or two on how to play a real game of pool,"

Now nose to nose, she giggled in response, and stepped away. Dean let out a deep breath and watched as she set up the table for another game.

"Rack 'em up then pretty boy." She grinned, passing him the triangle wood piece. Dean shook his head and finished his drink before grabbing a pool cue, feeling anxious about the game.

"So, you think I'm pretty huh?" Dean winked. She rolled her eyes in response as he finished up racking the balls. "My name is Dean," he said as he thrust out his hand.

She glanced at his open palm and returned the gesture, "Nicole," she replied simply.

Dean half grinned, "Finally, a name to match the face!" He exclaimed. Dean attempted to pull away, but Nicole chose to hold on.

"Wait a sec cowboy, we need to settle on a wager first." Nicole stated. Dean nodded and gestured for her to continue. "I usually charge a hundred a game but for you…" she paused, giving him a once over, "you look like a real challenge. So…how about one fifty?" She questioned. Dean guffawed. 'This chick was as bad as him!' Dean thought to himself, but grinned nonetheless.

"You bet me more cause I'm a challenge?" He asked in a flirty tone, pulling her towards him. She almost gasped at the change of pace. "Is that really fair sweetheart?" He asked with a raised brow.

Nicole was messing with his head, playing into his ego which was apart of her technique aside from her skill. She knew he had one…all guys like him had one. She knew when he first entered the bar, especially when she felt his eyes on her. He was a drifter and assumed that she was a tease that was willing to give into his every whim. But like the others, he was sorely mistaken, and she couldn't wait to knock him down a few pegs.

"Take it as a compliment, pretty boy," she smirked as she pushed him away, taking note that he was fairly muscular. Nicole shook her head and stuck her hand out once more. It wasn't time to get distracted, it was time to win another game. "Do we have a wager then, Dean?" she asked, rolling his name off her tongue.

Dean pursed his lips thinking he had a decent chance. "Deal. You can break since you seem pretty handy when it comes to busting some balls," he half grinned.

Nicole sighed, "yeah, never heard that one before…" Nicole rolled her eyes as she veered forward with the cue poised and ready to break. She looked up at Dean across the table through her dark lashes and pulled the cue away slightly then struck hard.

The colorful balls scattered around the table and half of them went in the pockets. Dean's jaw went slack for the second time that evening. Nicole smiled as she gazed at Dean's expression. She sighed happily, 'it never gets old' Nicole thought to herself.

"I call solids," she moved around the table, ready to take her next shot. Only a few solids were left on the table after she broke and she had a plan laid out.

"7-ball, side pocket."

"2-ball, corner pocket."

"6-ball, side pocket."

She shouted each of her moves and executed them perfectly. Dean stood stock still, shocked that she played so well. He didn't even get a chance to try and Nicole was already set to deliver the end shot.

"Well, I'm screwed…" Dean grumbled.

"Not quite," she replied, figuring how to deliver the final blow. The eight ball was located in between a pair of stripes near the center of the table while her cue ball was near the opposite side.

Looking at the table, Dean felt hopeful as she pondered her next move, biting her bottom lip. He inadvertently licked his own as his mind drifted away from the current game. Instead, he allowed himself to picture Nicole bent over that very table for unrated reasons.

Back at her side, Nicole smiled and got into position. "8-ball corner pocket…" she stated, gesturing to the one closest to her.

Dean came down from his x-rated thoughts curious as to how she could pull it off. Taking aim, she shot her cue with enough force to hit one of his stripes which then collided with another. The second ball clacked against the 8-ball with enough force to hit the side of the table and trail slowly into its assigned corner pocket.

"Ok, now you've been properly screwed," she said with a smile. Dean scoffed thinking of a better way to screw. She moved around to his side of the table feeling smug as he began to pout. "And here I thought it would be a challenge," she said with a click of her tongue. "Pity."

"Double or nothing." Dean stated firmly. Nicole's smug look fell as she shook her head.

"Awe, don't be a spoil sport! We shook fair and-"

Dean interrupted her as he pulled out five hundred dollar bills and slapped them on the table between them. Nicole's eyes lit up and she shivered in excitement.

"Five hundred dollars, one more game. You in sweetheart?" He asked, voice gruff, and eyes serious. They locked in on her mischievous ones. Eyes that never backed down from a challenge.

"I'm in." She smiled not realizing then that that was the first of many challenges and the first of even greater adventures.