Catching Up, Season Two
Chapter 11 – Crossroad Blues

A/N: Hey all, I was really hoping to make this a part of a much bigger upload, including five new chapters for this story but there have been a few delays and I don't want to let the completed work sit any longer. Just know that they are on the way. I love you all. Stay safe out there. And as always, ENJOY! R&R PLZ!

Dinner was a pleasant affair after which they reconvened in the living room to start again. Mary restarted the DVD and checked the episode list. "Crossroad Blues," she announced to the group. "She'll make your dreams come true for a price…your soul. Dean confronts a demon straight out of Faust who makes the young ghoul hunter a startling – and tempting – offer. Well then," she cocked an eyebrow. "This should be interesting."

"Rarely a dull moment Mrs. W," Crowley toasted the air. The show opened in a bar in Greenwood, Mississippi, August of 1938. A man was playing a beautiful jazz tune for the patrons when the sounds of growling animals and shadowy figure out the window gave him pause. He ran out of the bar and to his home, presumably to hide from this unseen creature. When his family finds him, he's muttering about dogs, black dogs, before dying and cutting to the title screen.

"Hell of a cold open," Crowley smirked.

"I can't tell if that was clever or cringeworthy," Sam made a face. "One of yours by the way?" he pointed to the screen.

"Hellhounds aren't immortal," the former King of Hell informed him. "That was probably one of my pack's grandparents."

"So hellhounds," Mary nodded. "Great. Good start. And now my son is bragging about being on an FBI watch list."

"Sorry mom. But Sam was totally jealous"

"Oh yeah, positively green with envy," Sam snorted. The boys were investigating the suspicious death of a successful architect that spoke about wild black dogs before committing suicide a few days later. They interview his business partner and they find out that the victim had become an overnight success while working at a bar ten years prior.

"Ten years," Rowena shook her head. "The perfect mix of not too short and not too long. Just far out of human comprehension that they think it's plenty of time and before they know it, it's over."

"The Goldilocks number for those in the business," Crowley sipped his scotch. "It might seem like a long turnover time but honestly ten years is nothing to the eternal."

"Does it have to be ten years?" Castiel asked.

"Nope." Sam, Dean, and Crowley said together.

"Comes down to the broker boys," the demon explained over the TV!Winchesters evidence gathering. "Some people get more, some people get less. It is possible to argue for an extension depending on how useful you can be or for a broker to decide you're making too much noise and end the deal early."

Fascinating. Wait your brother thought MySpace was a porn site? You can't see it but I'm embarrassed for him. "Oh I'm embarrassed too." In the show, the boys go to speak with Dr. Sylvia Pearlman, another overnight success, but she's gone however they do make a connection between to the architect and the doctor – Lloyd's bar. The show cut to a woman, presumably the doctor, terrified and hiding in a motel with a demon literally on her doorstep.

"That poor woman," Mary frowned.

"The price of evil love," Rowena shrugged.

Meanwhile the boys investigate Lloyd's and discover it's situated at a crossroads and all the items necessary to make a deal. "Little secret for you boys," Crowley said smugly. "You don't need any of that. Just a bit of theatrics."

"What?" chorused the room, Cas paused the show.

"It's true," Rowena concurred. "Demon deals can be anywhere anytime. You boys knew that already."

"Yeah I guess we did," Sam frowned. 'kay now I'm embarrassed for the both of you.

"So then," Dean flapped his hand at the screen. "Why?"

"A couple of reasons. Most importantly, it keeps the rest of the world less suspicious. And for those who do jump all the hoops, after they paid back their debt, I would make them my new dealers," Crowley said proudly. "Think about it, how much dark ambition must one have to do all of that to make that specific kind of deal."

"And the ones who didn't use a crossroads," Mary ventured.

Crowley smiled beatifically, "They knew what they were signing up for Mrs. Winchester – for all eternity." This was perfectly accented by Cas restarting the show where hellhounds attack the doctor, dragging her off.

The show cut back to 1930 where the famous blues player Robert Johnson made his own demon deal at the crossroads, inspiration for his work. In the present, the boys discuss him and tracking down anyone else who made a deal. TV!Dean is somewhat reluctant to help as they've brought it on themselves but TV!Sam insists. They use the pictures inside the box and find an artist George Darrow. He's using goofer dust to hold the demon and hounds at bay. He had asked for talent but not fame, none of his painting ever sold. Turned out that he was the one who initially called the demon and it stuck around for another week making deals. The doctor, the architect, and another Evan Hudson.

George turns down the boys' offer for help; he's only waiting until he completed his last painting. TV!Sam says he doesn't really want to die, George says he tired. "You would have brought him on too?" Sam asked Crowley.

"Nah, hell's only hell when you don't want to be there," Crowley said. "Once you've resigned yourself, understand why you deserve it and accept it, you don't belong there anymore. That's when Cas's squad cuts in."

"Only in rare cases is a soul like that just brought to heaven," the angel added. "Most of the time, the soul is forgiven and receives a new opportunity to live righteously on Earth."

In the show, the TV!Winchesters catch up with Evan Hudson who sold his soul to save his wife's life. Not unlike the deal John made for Dean… The boys admitted they both suspected he had done it ever since they took the case. Mary sniffled lightly, "What happens to the those who make the deal for good reasons?"

"They would serve ten Earth years in the pit and then be granted the grace of the Host," Crowley swirled his drink. "Were they anyone but John Winchester. Hell would have kept him for as long as it took."

"Which my garrison stormed it," Cas said looking directly at Dean. Mary looked between all of them but didn't comment.

Meanwhile TV!Sam is protecting Evan while TV!Dean tries convince a demon to release his contract in exchange for his own soul. The demon confirms that John made a similar deal but catches on before TV!Dean could trap her. As this is going on, hellhounds close in on Evan and TV!Sam. This is gonna be bad. "Ye of little faith," Sam muttered.

The demon taunts TV!Dean's misery over having John give his life for him. Even saying that she could have brought him back. John would lead a natural life and TV!Dean's soul would get taken after 10 years. For a moment it looks like TV!Dean is tempted by this but it's revealed he only did it to lure her in to a trap. "Satan you really had me going there," Rowena held her heart. "Dean Winchester you should take up acting."

I can see him a soap opera now. "So can I," Sam smirked running through the memory in his head. Oh wow. Onscreen, the hellhound is bearing down on TV!Sam and Evan whilst TV!Dean prepares to exorcise the demon. He begins chanting and TV!Sam and Evan trapped in the laundry room, about to be caught. Just in the nick of time, the demon agrees to the deal and voids Evan's contract in exchange for being let go. For a moment, it looks like TV!Dean was about to renege but lets the demon out. She taunts him about his dad before taking off, leaving the vessel behind. "I can't," Mary held her head.

"It's okay mom," Dean wrapped an arm around her. The boys are shaken and TV!Dean all but admits he considered taking the deal, leaving the show on a somber note.

Crowley muttered lowly, "Anyone but the Winchesters."