Dean came to first, his head feeling unusually heavy and had an uneasy feeling. He could not recall falling asleep or even ever being in this room. He attempted to lift his head to his eyes, but found himself unable to as he was restrained in a heavy wooden chair.

Dean's head shot up as he swept his vivid green eyes around the bare white room. A heavy feeling of dread filled his empty stomach as he desperately searched for his little brother. "Sam?" he called out uncertainly. His efforts were rewarded with an irritated groan from behind him to the left.

"What Dean?" Sam responded groggily, the affects of whatever drug had been used on them had not worn off yet.

"Do you have any idea where we are?" His question was met with silence.

"What the hell?" the younger brother exclaimed as he became more aware of his surroundings. The silence hung heavily in the room for a few moments.

"Maybe we should call Cas?" Dean suggested, they tried to summon the angel.

"I'm behind you" the angel's monotone broke the silence. The brother's craned their necks around to see an unimpressed angel standing in a ring of holy fire. "Why are we here?" the angel questioned, apparently he didn't enjoy being stuck in one place for so long.

"You Flyboy, are here because these two are unable to follow simple instructions," a strong, feminine voice echoed in the room. Their heads snapped to the front where a woman had just entered, dressed in a short black dress and kitten heels. "I'd have released you by now, had I not found some very interesting items in your possession."

"I am an angel of the Lord, those are weapons of heaven, they are incredibly dangerous, it is imperative that you return them at once," the angel spoke up. Dean assumed that the angel's loud mouth had just screwed them all.

"That I am aware of Castillo, however I do not wish to return them just yet. You will get your toys back soon enough." She broke the staring contest with Cas and placed her gaze on Sam.

"I'm sorry for the inconvenience, Sam Winchester, it appears that your brother shares trust issues with your father."

Sam wondered what Dean might have done to land them in this disadvantageous position.

Three hours earlier…

The Winchesters were in a bar, they were waiting for a contact found in their father's journal. The letter had no name, just a phone number and very explicit instructions. If they ever needed anything, they were to text their location to what they discovered to be an untraceable cell number. The letter indicated that whomever this unknown contact was that they were held in very high regard of the late John Winchester.

Sam was standing leaning against the wall near the bathroom, Dean was hustling pool across the room. Their contact was over twenty minutes late and no one had entered the bar in the last forty five minutes.

A young woman with dark curls brushed her fingers gingerly over Sam's lower abdomen as she glided past him towards the bathroom. His muscles clenched at the light contact as he looked after her. The woman was quickly forgotten when a tall, unshaven man entered the bar.

Sam made eye contact with Dean and strode over to the bar. Dean sunk the eight ball with ease and pocketed the bills that were on the side of the table, and moved across the room to join his brother.

Sam felt the sharp poke of plastic into his thigh as she sat on the bar stool. Pulling it out, his eyes searched the crowded room for the dark haired woman; not finding her, he examined the plastic key card to one Holiday Inn.

It was a full hour after their contact had been expected to meet them. Dean had long since grown impatient, "He's not gonna show, let's go back to the motel, we can try again later."

As they were leaving the bar, Sam showed Dean the key card. Dean immediately demanded to know if it was from their contact or an overly forward woman. Sam honestly had no idea, so they drove to the hotel.

Dean offered to wait outside just in case it was from a drunken woman. The lights on the automated lock shone green as he was granted access. Sam hesitantly opened the door, there was not a soul in his direct view of the suite.

"You've kept me waiting a while Sam," the man jumped at the voice that came from the direction of the bathroom. The young woman from the bar emerged, clad in only a towel, with another on her hair. "Where's Dean?"she asked. The older brother poked his head around the corner. He let out a long, low whistle. "Are you gonna come in, or stand at the door all day?" She questioned, grabbing more clothes, she reentered the bathroom.

Dean entered the suite, shutting the door behind him. He shot Sam a curious look, which was answered with a shrug. The bathroom door opened, and she joined them in the kitchen of her suite. "Drink?" She offered them a bottle of whiskey. They accepted, and she poured two glasses.

"So what can I help you boys with?" she leaned onto the island in the small kitchen. The brothers looked at each other, she was definitely not what they were expecting.

"How about you tell us about yourself first sweetheart?"Dean suggested, attempting a charming smile. The woman snorted, covering her mouth with a perfectly manicured hand. Their vision was starting to get foggy.

Her eyes sparkled with amusement as she returned their gazes. "Usually a hunter checks before accepting a drink from a stranger."

What do you think? First story I've written in years, please review. This will loosely follow the story line. I'm not sure who my OC will end up with, Sam or Castiel. Not Dean, Lisa may turn up in a few chapters. More will come soon. You will learn more about this OC in the next chapter.

-Sassy