Hey guys, so this is twenty chapter fic I wrote for a friend of mine. Right now it's a teen rating, but depending if I have the energy to had a few things later the rating may change ( ;) ) Until then I hope you enjoy it! I'll try and post a chapter every week, but don't hold me to it. I get lazy, and or busy. Also! It may become part of a series I've been thinking of, but not sure if I'm going to do yet. So... that is pending. Thank you for reading, and I hope you enjoy!
Please review what you think. Thank you all again for reading 3
*Disclaimer* I own nothing but the story line.

Dean propped his feet up on his desk. His hat covering his eyes as he crossed his arms. It was just another dull day in the town of Sioux Falls. His latest captive was sitting in the cell in front of him. He was brooding over being caught… Again.

It was about the twentieth time he'd been in there. The boy was a classic pickpocket in town, though not a very good one. He was beloved sure, but very troublesome. Dean had been trying to make him go straight since the beginning. He'd given up years ago though. It wasn't worth the effort anymore.

Dean blinked his eyes closed as the young man yelled at him from his cell. He resisted the urge to yawn; this was the same every time. Honestly, he thought the boy would be a better thief by now. No bite though. He was still as crappy as when he first caught him.

"Again?" His deputy groaned as he came in.

The sheriff looked up; lifting his hat with a shrug "The kid was caught tryna steal from ol'Singer."

Sam sat down across from Dean, eyebrows raised in surprise. "The boy's gotten stupid." He noted with a sharp laugh. "Bobby would never let of his stock go missing. What'd he try to steal anyway?"

Dean shrugged "Some tool I think."

"Idiot." Sam laughed again.

"And he's right here!" Ben called from the cell "It can't be nice to insult a man who's standin a foot away!"

The tall deputy glared over at the cell "Maybe if you learned a lesson every once and awhile, you wouldn't be in this situation son!"

Ben sat on the edge of the small cot. He didn't say anything else, admitting defeat. He knew he'd be out later that day. Lisa would come by, muttering apology after apology and paying for whatever it was he took and what his bail was. Lucky for the boy he came from a rich family. One of the richest families in town in fact! After the first time Lisa had come down here, with her father no less, they'd been trying to marry Dean into the family. She was a pretty enough girl, and they'd had a one night stand years back. It had happened just after her father had started coming around trying to gain a son in law. To this day, Dean wasn't sure how it had happened. Some drunken night no doubt. Either way, it had been great and all but he had never seen himself as the settling down type. He was a man of his job. He couldn't have attachments.

Dean smiled to himself, as boring as Sioux Falls was; this was an excitement he could always count on. The troublesome Benjamin.

The town had been here for years. Always bringing in different characters. It was a huge trade town. Meaning, of course, that it wasn't just innocent trades men who blew through. There were bandits and other gangs. There was one in particular Dean had been searching for, for years. They were a crafty crew, he gave them that much. They knew how to stay hidden; he only knew the basic place where they may be.

Dean had become Sheriff after his father died ten years back. His mother had died when he was very young and so Dean had very little memories of her, besides of course what his father had told him. What he'd told him and his little brother Sam, his deputy. The two of them had gone into the family business together. Sam would take over when he died, or retired. He hoped for the latter personally.

As much as he loved the job, there were some days where he wished it were different. When he had failed to save someone, or he had to let a criminal go because he had a good lawyer. It was incredibly frustrating and Dean wished it could be easy. Black and white. No grey areas. His dad always told him it was black and white. There was no leeway with the law. Dean did his best to live that way, there were just some things that he couldn't see as simply right and wrong. Reality didn't work that way.

"Dean?" Sam said, dragging him from his thoughts.

The sheriff glanced up at his brother. The deputy was motioning with his eyes at his feet on the desk. Dean slowly lowered his feet with a cheeky smile "What can I do for you Sammy?"

"Have you finished the paperwork for Ben's release?" His brother asked "You know Lisa's going to want a quick release once she's paid."

Dean groaned inwardly "Almost. I thought I'd take a lil' nap first." He hadn't been sleeping well lately. Bad dreams plagued his sleep every night. Dreams from back when… Well he didn't like to think about it much. Even Sammy didn't know about them. Dean intended to keep it that way too.

Sam rolled his eyes "Better get it done now. Lisa will be here any minute now." The deputy glanced at Ben again before walking toward the door "I'm going to check on Bobby." With a last pointed look he left the small station.

"Ya know… I should make you stay here longer this time." Dean told Ben "Maybe then you'd learn not to steal. A few nights here, living like a common criminal."

Ben's face contorted in fear. He began spewing apologies, swearing on his life he'd be good. The boy knew that if he stayed here more than a day on a thieving charge there'd be no hope. He'd go to the county prison on the next train out of here.

A satisfied smile passed over Dean's lips. Yes he'd be good this time. Dean would ship him off next time. After all, Dean couldn't keep him out of trouble forever. Ben had a lot of growing to do. His mom worked hard to keep him in line. It must be hard without his father around anymore.

Mr. Braeden had died three years after Ben had been born; a freak accident in the mill. He'd been surveying his employees when a saw had been set a speed much too high. He'd been caught in the pathway. The guy never had a chance. The town had mourned for months; the man had been much loved. He'd given jobs to those who needed them and was fair to all he needed him. He never forced someone to work overtime, understood when they needed to be with their families. One of the best bosses out there. It only went to show that bad things happen to good people.

Settling to work on the papers he kept a careful eye on the boy while he did. If Lisa wasn't here in a few hours she would certainly be there early tomorrow. Sam, as usual, was right too. When she was here she would want to pay and get out of there as fast as she could. Dean got the sense she was somewhat embarrassed by how much Ben was in here. She loved the kid of course, but he understood where she was coming from. Dean hadn't been the best son at times when he was little.

He worked silently, filling out form after form. A half hour after he started, a cry went up from outside. People screaming as a man shouted. The shout was closely followed by the sound of the loud bang of a gunshot.

Dean's eyes snapped up and he stood hastily. He rushed out into the open, ignoring Ben's rapid fire questions. Dean burst through the door of the sheriff's office to the see the scene outside.

Outside he found a crowd of people standing over a dead body, but at a great distance. The gunman was still standing over his victim. A pleased expression on his face, the gun still pointed downward at its target. Dean felt a sick feeling twist in his gut at the happy upward tilt on the criminal's lips.

The man had black hair that was being ruffled by the soft wind that was blowing through town. He was tall with what Den guessed heavy set muscles. He wore a long black coat that swirled around him. Even if Dean couldn't see the gun clearly he knew what it would look like. The gun would have intricate black wings on the side, flaring out near the handle. Because of this, he also knew the name of the gunman.

Castiel.

Part of the gang Dean had been after for years. The Garrison. The most wanted gang of criminals in the whole of America. There were posters all throughout the tiny towns across the country with his face, and the faces of the other members, on it.

"Grab him!" Dean yelled.

He wouldn't escape this time.