A/N: DISCLAIMER: I do not own Supernatural, or any of the characters. All credit goes to Kripke and the amazing talent behind the show. Written as a request from mandancie. Hope you enjoy!
Roy sat nervously in the booth, nursing a cup of coffee (which had, no doubt, been sitting in its pot for hours, considering the fact that it tasted like shit, but hell, it was hot and wet, as his Momma used to say). He'd been sitting in the diner for what seemed like hours, ordering cup after cup of the liquid sludge and ignoring the glare from the server, who was no doubt waiting impatiently for him to get his ass out of the diner, or at least order something worth more than a buck seventy-five. Hell, he wanted to get out of the joint. If the food was anything like the coffee, after all, it wouldn't be worth five two goddamned cents let alone two fucking dollars. But he had a job to do. Walt had seen to it that Roy finishes what they had started.
It was supposed to have been over by now. He and Walt had killed the Winchesters, gunned them down in their motel beds. Well, Walt had. The other hunter had not only emptied his shotgun into little Sammy's chest, but big brother Dean's too. Roy had never wanted to see Dean die. It was Sam who had kick started the apocalypse when he had broken that final seal, not Dean. The older Winchester had done nothing to deserve being murdered in his damn bed. And to top it off, he knew damn well that once other hunters knew that Dean Winchester had been killed in cold blood, others, especially that old coot Bobby Singer, would come a'runnin'. Something that Roy wanted to avoid like the fucking plague.
But Walt had insisted that he shoot Dean too. After all, he had just witnessed the death of his beloved Sammy, and in such a horrible way. He knew that if the hunters had left the elder brother alive, they would regret it for the rest of their lives. And he was right, Roy knew that. There was no way in hell that he would have liked spending the rest of his miserable excuse of a life hiding from the man who had sworn to protect his little brother at all costs. But he couldn't do it. He just couldn't pull that trigger. And Walt, impatient with his partner's hesitation, had solved that problem mighty quickly.
But, by some miraculous reason, the Winchesters had been resurrected, brought back from the dead for what seemed like the hundredth time. At first, he and Walt had been not only confused, but scared shitless at this startling revelation. Something incredibly powerful must have done the deed, brought life back into their lungs; the work no less than a mighty demon, one perhaps as powerful as Lilith herself had been, if not more. It didn't take the two men to realize that the Winchesters had yet another powerful ally on their side: angels. Angels, for god's sake! A bit of research revealed the celestial being to be one Castiel, one who ultimately became quite fond of the brothers (Dean, in particular). In short, to try to kill the Winchesters would prove to be a useless endeavor. Why bother trying to take down someone when a goddamned angel would be able to bring them back with the touch of a finger?
But further research concluded that the brother's feathery friend was out of commission, presumed dead. In other words, the perfect opportunity for him and Walt to finish what they had started.
After what seems like hours, Roy hit the jackpot. The familiar coal black Impala parks practically in front of the window where the hunter is just finishing up his latest cup, and the men of the hour wearily climb out. The brothers looked exhausted, but Roy noticed that Sam, especially, looked like hell frozen over. Roy watched from the corner of his eye as the two men walked right past his booth, not even noticing as he quickly reached for a menu and pretended to look through it. When he felt that his cover has not been broken, he tossed the laminated booklet aside and watched as the brothers picked up their own copy and scanned through, Dean surprisingly not bothering to flirt with the hot server who took their order. Roy pulled out his cell phone, eyes darting around him nervously despite the fact that there was technically nothing odd about a man placing a call in a public establishment.
"Yeah?" Walt's voice was gruff on the other end of the line.
"Found them. Eating supper at Frank's Diner in Milwaukee."
"Good. Don't let them out of your goddamned sight."
"Yessir." Roy pressed end on his phone and tossed it on the table. When the same pretty girl who served the Winchesters came back with the coffee pot, he declined and ordered a Bud. He slowly sipped his beer, and had ordered another, by the time the brothers finally signaled for their check and grabbed their coats. Not about to let the Winchesters slip away again, Roy signaled for his own, tossed a handful of crumpled bills on the table, and followed the brothers out the front door, ensuring to stay a few paces behind, so as not to draw suspicion. Ducking behind the shadows, Roy climbed into his rusty pick-up, waited until the Impala disappeared around the bend, and gunned his own.
He had work to do.