So this is my first Supernatural Fic set in the 1940's, chock full of monsters, blood and guys, romance, strife and all other sorts of goodies. This chapters song is "Sing Sing Sing" By Benny Goodman. So sit back and enjoy this Mobster Destiel Fic from me to you! I do not own Supernatural or it's characters, however I do own this fic!

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The shot of Old Fitzgerald Bourbon Whisky went down his throat like a flame, engulfing his mouth and tongue- hot and scalding with a bitter tinge to it towards the end. It did just the trick to shake the hunter up enough to gather his wits about him as he swallowed the amber colored liquid.

Well, whatever wits he had left in his already muddled up head.

The night hadn't gone well for the older Winchester. No, not in the slightest.

What should have been a routine kill for a haunt in an old textile factory, quickly grew into what Dean could only describe to be a frantic fight for his life. Who knew Ghosts could be such a pain in his ass?

The gig Bobby rung him up about this morning sounded nothing more than a spirit lingering around some run down old factory. Nothing too out of the ordinary, just a few hours of research at the library that he had his kid brother Sam do for him - seeing as how Dean really had no contentment to sit himself down in one of those dusty libraries and read till his eyes grew cross eyed.

It was a little after the clock in his house blared Twelve O'clock that he got the call back from Sammy that there was a suicide back in the twenties of one Elizabeth Goodritch. She had apparently stabbed herself with her sewing scissors in her throat - nice and bloody and gruesome. Just the way Dean liked it. Nothing a good ol' routine salt and burn tactic couldn't solve.

Oh damn was he ever wrong.

Turns out the Dame was never buried but cremated instead into a pound of ash - the nice and furious Ghosts usually are, Dean had come to realize early in life.

That being the case, Dean had decided to go all in, guns ablazin' to take care of this twisted broad before she slit some other poor helpless construction workers throat in the dead of night. Rushing into things usually worked for Dean, it meant he lacked emotion - and in a job like this, sentiment can get you buried six feet under. If you're lucky.

However, two sawed off shotguns, a whole dozen rock salt rounds under his coat, two silver knives in sheaths down the small of his back - and all of them lost except for a few capsules of rock salt - not enough to throw at a Demon to make the damn thing flinch.

To say the least, it had gone horribly wrong fast.

Elizabeth Goodrich must have been one uptight bitch in life, because she was a major psychopath in death. She came at Dean with nails raised, eyes sunken in and menacing looking - oh, and a big ol' pair of cloth cutting scissors in her hands too, you know, the ones she used to kill herself with all those years.

Anyway, what should have been an hour job turned out to be three and it left Dean pretty low on the fun meter, hence the drained hunters visit to one of the only hunter friendly bars in town, the Road House.

It was a nice place - not exactly the Ritz, but the live band was good on Fridays and Saturdays, the whisky flowed from the bottle easily, and there was always a nice Dame or two at the bar for Dean to get his eye fill. But not tonight. No, tonight he felt like getting piss drunk till he passed out. Screw conciseness, that's what he always said.

Taking another tentative sip of his bourbon he ran his tongue on his pearly whites and sucked the inside of his cheek. Damn the whisky here is strong, he thought with a pleasing smile. The better to uplift this rotten mood.

He had been waiting here for a little over twenty minutes, soaking up the smell of cigars and cigarettes, of giggles from pretty women with rosy cheeks and curly hair, and listening to the clatter of chips and the fanning of decks of cards on stiff tables. It was music to his ears. No screaming, no crying, no blood, no gunpowder blastin' and not a single supernatural son of a bitch in sight. Oh boy did he love the Road House.

However, he wasn't just lounging around here for kicks. No, Bobby had sent a telegram to the Road House while Dean was out dealing with Miss Bitchy-Undead. Bobby knew Dean like the back of his hand, figuring that after the oldest Winchester sent the ghost to rest, he'd be off to the bar to cool down.

The message that Dean received in chicken scratch sloping writing from Mr. Singer was straightforward enough, exactly like Bobby. "Got that Job for ya' that I've been telling you about. Meet me at the Road House at Five and don't be late, Idjit." The wryly older hunter sure did love to ruffle Deans feathers, not like he minded too much. Bobby was like a father to him ever since his own dad passed away, he could call Dean Idjit all he liked - Dean would never tire of it.

His fingers began to crease the little folded paper in two, nice lines forming along it's edge. The note was simple enough to jog Deans memory back from a week or two, about a certain conversation he had had with Bobby over a flask and two glasses of chilled ice.

It was a job, but not like anything Dean had ever handled or taken before in his long years as a hunter. It wasn't a raid, wasn't a hit and run, wasn't a rescue mission or a drugs bust on a house full of Demons - it was, well, to put it simply. Baby-sitting.

Now, Mr. Singer hadn't actually called it baby-sitting, instead he had very persistently described the job at hand as needing Dean to be a Body-Guard and Teacher to a new pupil. To which Dean snorted, called Bullshit, and became increasingly on edge about even accepting the task. It just felt too out of ordinary of his nicely straight forward career which entailed of shooting the bad guy, burning the body and receiving the doe at the end of the week to pay the pills. Simple, Easy, and fun as hell - just like Dean liked it. Baby-sitting some Bunny-Boy from the sticks however, did not sound fun, not one bit.

But apparently three weeks ago Bobby had got a telegraph from some kid in Louisiana wanting to join their little rouge gang of hunters headed by Mr. Singer. According to the older Hunter, the kid had potential. He was pretty young, healthy, strong, and had some God damn impressive reflexes that made him into a true warrior - a weapon was the word Bobby used, which irked Dean to no end.

In the telegram that the kid sent Bobby he explained his situation clearly and precisely. He no longer wished to live under his Fathers roof with his brothers and sisters who were not the nicest people in the world. He wanted to live on his own a bit and 'see all the wonders of creation' or some other bullshit yuppy crap like that.

To Dean it just sounded like the guy had daddy issues or something - wanting to fly the nest and explore the town, city, the whole world. Sounded like a sap with a few screws loose to Dean.

But what really bothered Dean, what really got under his skin was the fact that the guy wanted to try his hand at becoming a hunter. And that just didn't sit right with Dean. Folks don't want to be a hunter - they just become one. You see something horrible like a lady being dragged under a sewer grate screaming for help, have something horrible happen to you like losing your daughter to a shifter who couldn't stave off his appetite, or have your arm bitten off by a ghoul before someone shoots the fucker dead - and you just become one. You pick up the sawed off shot gun, shoot the mothers head off and move onto the next one. That was the life of a Hunter, that was the life of Dean Winchester, and he sure as hell didn't pick it.

Dean sighed through gritted teeth and ran his hand over his hair, ruffling it's shortness some but not by much, the grease in his cropped locks keeping it nice and slick.

He flicked his fingers over the tightly folded telegram again, running his sea-glass colored eyes over the pen ink that clotted slightly from Bobby's haste to write it.

Honestly, the job didn't sound so appealing to the young hunter. Dean's plate was already filled the brim and heaping with guts and severed body parts and everything else nasty and vile imaginable. He didn't think he had the time to teach a Green-Horn all the ropes. Demons had been getting into the drug business, and the number of Cross-Road workers had doubled. The Shifters were acting up along the west of the city and the pack has just been growing like a weed, not to mention all the un-dug bodies lately that were suspected to be the activity of ghouls. There just wasn't enough time.

It wasn't training the guy that was the problem - Dean knew how to mould a good fighter, a good shooter outta' anyone. He had helped his younger brother Sammy through this line of work, had seen him come out scratched and battered, but alive just the same, and stronger than ever. He'd helped Chuck get through his anxiety and taught him how to knife a beastie in the throat. He had showed Jo how to draw devils traps on ceilings where the demons were less likely to look. Dean knew how to take care of people better than he knew how to take care of himself. He was good at teaching when the people wanted to learn - but that didn't mean he wanted to take on some fresh doe-eyed pup who thought the job was glamorous.

Being wrist deep in decaying bodies and slathered in flaking blood and other sticky stuff was not glamorous.

However, Bobby said the guy's father was willing to dish out the cash to pay for his sons availability to go into training and to work for "Team Free Will" as their group of Hunters became known as in the area.

Now Dean was no money grubber, but cash for weapons in this day and age while the good ol' yanks were fighting the Germans was scarce and hard to come by without the Chopper Squad confiscating the dough or asking questions. Connections were thin and hard to come by already. Their little group of hunters needed more money to buy salt rounds, machine guns, books on information, and just to be clear - silver bullets did not come cheap.

Plus another benefiting factor of taking the new guy in was that Dean could use the money from his added paycheck to buy some parts to fix up his baby - a 1940 Black Cadillac Imperial. His damn near pride and joy.

Deans smile suddenly turned grim as he huffed in gruff aggravation.

Well. It seemed that Dean Winchester was a slave to money, besides the fact that he didn't think he had it in him to tell Bobby no.

After raking his short nails over his still dusty and sweaty face Dean slammed the empty shot glass down onto the bar counter, the glasses rim coming back sticky and salty from the bars unclean surface. Dean winced and decided he should probably switch from whisky to beer for the night, lest he wanted to get picked up by the Chopper Squad for milling the streets all drunk and disorderly. And as much as slurring his words and blacking out in the middle of the street actually sounded appealing - he had to go to work tomorrow bright and early to train the new Rich-Kid. Plus, Bobby didn't seem like the kind of Boss who would be all too thrilled to have one of his hunters smell like Bourbon and throw-up. No, Dean wouldn't want a repeat of that again.

So, being the classy gentlemen that he was, he, slammed his hand on the bar table, trying to act more cheery than he felt and called out to the Bartender, Ellen whose ability to sell Dean liquor at this moment made her his new best friend.

"Hey Ellen." Dean grins slow and lazy, his eyes shining and watery as he gestures to the tiny little shot glass on the bar table, still wet with whisky clinging along it's edges. Nice and amber looking in the smoky light of the bar.

The woman, age showing slightly on her face underneath the pastel powder of her cheeks, looks to the young hunter on his stool, her eyes narrowing slightly, hand making its home on her hip.

"What can I do for ya' Dean?" Her voice is a bit throaty and tired from answering previous hunters questions and giving out information all day but her voice makes Dean smile, as Ellen reminds him of his own Momma' who died way back when he was just a little brat. Two parents down and buried six feet under, sounded more and more like a Hunters life than Dean cared for at times.

"Can I trade in my glass - I wanna' get some beer in my gut while the night's still young." Dean gave her that shit-eating grin that he was all too fond of keeping on his lips while he gestured to the outside, the spring weather casting it's last warm tendrils of light into the sunset as the outside oil lamps were lit to give the street some more light.

Ellen looked to Dean with her own little huffing smirk, her fingers still as she paused from wiping a wine glass clean till it shown bright and clear.

"Sorry big boy, one more drop of liquor for you and I think you'll be pushing up daisies on the side of the road." Her eyes smiled as she placed the wine glass underside up on the shelf, the tinkering sounding like little glass bells amidst the somewhat loud clamor of the other patrons who were slugging down their own drinks.

Somewhere off to the side where the bar's record player sat prettily on a little cheery oak table, Jo, Ellens daughter, was fiddling with the needle on the contraption, trying to find the right song for the evening to lighten the mood. Every Hunter needed some soothing tunes to block our the hideous things they've seen earlier in the day.

"Awww, you're no fun." Dean pouted like a regular charmer.

"Never said I was." Ellen never wavered, catching on to the act quicker than wildfire.

All of the sudden a great blaring was heard from the crackly old record player to the side, the music coming out sweet and twang-y through the air. Benny Goodman's "Sing Sing Sing" trumpeted outward, sounding oh-so good to the ears, getting the body jumping and swaying - too bad Dean's blood was sluggish in his veins at the moment and his bow-legs too damn tired to even pick themselves up from the bar stool to shake 'em out.

However that wasn't the only sound that he Winchesters ears picked up at that moment.

A few bars into the song where the drums began to beat furiously and the patrons began to waggle their fingers and holler, the Road House's wooden door made a creaking sound, the bells above the opening crinkling to notify that another customer had made their way into the hustle and bustle.

It was then that Dean's ears pick up the gruff voice of Bobby above the grainy music. His voice was nice and assured, somewhat giddy even. If giddy could ever be a word used to describe Bobby Singer.

"You'll like 'em. He's not too gifted in the smarts department but he ain't no goon. He'll take care a' ya'." Dean heard his boss speak behind from where Dean was sitting. The Winchester only needed a few seconds to understand that Bobby was more than likely talking about him. Deans eyes squinted in quiet agitation at the insult that was directed towards him, knowing Bobby was only kidding about Deans intelligence…At least he hoped so. So then who was the other person Bobby was talking to?

"That is good to hear. I am sure I am in capable hands." Came the reply in a voice so damn smoky and gravelly Dean suspected it had to of come from a smoker. The voice sounded like smooth velvet that had been charred by flame and gasoline, then stepped and smudged into the gravel fifty times. It was an interesting voice to say the least and it left Deans arms all tingly and fidgeting.

Taking the opportune moment to turn himself from his bar stool to face his boss and his new companion with a wink and a wise crack about the old man and his own intelligence, Dean turned to see a sight he really did not know what to think of.

What was once a prepared glare for Bobby turned into a wide open mouth in the shape of an 'o', and eyes even wider to match. For, standing right before the bow legged green eyed hunter, was a stranger more beautiful than any dame or doll yet more rough around the edges than any sober man.

Tucked in nicely into a suit that screamed tailored, was a slender man a little bit older than Dean. Gruff chin in need of a shave and thin shaped lips made up the mans face as well as amazingly blue eyes that nearly shocked Dean off his seat. This man was gorgeous….

Dean was suddenly and a bit annoyingly brought back down to earth from his insistent staring of the blue eyed pale man before him by Bobby.

Clearing his throat, the universal signal for, Pick your Jaw up from the floor boy, we got work to do, Bobby sent a silent signal for Dean to listen and listen good lest he wanted graveyard duty tomorrow night.

"Hey Bobby… Whose you're friend?" Dean swallowed softly, his throat feeling like he swallowed a fist full of sand. Dear God those eyes, cornflower blue and crystal clear, as if Dean could just swim in those beauties…

Bobby could only roll his eyes at the younger hunter before he jutted a thumb at the tall, taller than Dean, man standing patiently next to him.

"Dean Winchester, meet Castiel Novak, You're new assignment and partner."

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Hey Guys, so this is my first Supernatural AU Fic and I want to make sure I'm doing it right. Also I'm trying hard to make everything accurate, however this fic is historically accurate to the last detail! So, tell me what you guys think? Is it worthy of the Supernatural Fandom?