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400 Years of Training

Summary:

Sam ends up deep in the pit after Cold Oak, and that far down, time runs a lot quicker than on the surface.

First part of a multi-part AU that will reflect the major canonical plot lines, but with some significant deviations. Later parts will be higher rated and relationships will develop (just as a pre-emptive warning).

Chapter 1: Paperwork

Chapter Text

3 days.  3 days was how long it took for Dean Winchester to conclude that life without his brother was unbearable.  3 days was how long it took for Dean Winchester to decide that he would give anything to see his brother again. 3 days was how long it took for Dean Winchester to find his way to a crossroads and prepare to offer his soul for his brother’s life.

Stamping the last of the dirt back into the hole in the centre of the crossroads, Dean looked left and right expectantly. He tried to give the demon time, but without his little brother in his life, his already limited patience was all but non-existent.

“Oh come on already. Show your face, you bitch!” he screamed in anger.

“Hey! Would it kill ya to be nice? I’m not even supposed to be here, just doing a favour for a friend!” came a voice from behind him, causing the hunter to spin to face the demon.

“Friends? I didn’t think your kind knew the meaning of the word!” he spat out venomously before taking in the demon’s appearance. Based on his knowledge of crossroads demons, he was expecting some form of temptress, what was standing in front of him looked more like an overworked college student, papers spilling from his hands and all.

Scrambling to pick up the dropped papers from the floor, the demon seemed flustered and Dean swore that it almost looked embarrassed.

“Well, not really a friend, more an acquaintance,” it mumbled, seemingly to itself, as it reached for the last few scraps of notepaper, “or neighbour. Damn Crowley, he just had to go and organise a crossroads strike, I mean it’s not like anything will change.”

Dean coughed impatiently, eager to get about the business of negotiating his soul.

The demon returned to his feet, but kept biting his lip and avoided eye contact, clearly nervous and unsure how to proceed. Dean hoped he could use this to his advantage, use the demon’s inexperience to give him more time. He let out a light chuckle when he realised that a story about a clueless demon would be just the thing that would make Sam smile when – when, not if – when he got him back.

“You gonna do that whole red eye flashing thing on me? Make you look all scary and make me thing you’re some kinda badass?”

The demon raised his head slightly, still muttering about Crowley and how he hadn’t been trained for this,

“Sorry, not one of my skills – I’m not exactly a crossroads demon so don’t get the red eyes. But in case you want reassurances –“ the demon let his eyes flash to white, the sign of ultimate demonic power, before continuing, “Technically, I outrank them, but I’m new to the whole fire and brimstone thing, so doing anything that put someone in my debt is ace. Unfortunately, it’s still got to be done by their rules.  I sort out the paperwork and send it downstairs, then I get to crack out the whole mojo thing and you get whatever your heart desires. Speaking of which, what deal are you offering?”

Dean gave a slight sigh – bureaucracy, there are always goddamn bureaucracy, even in the pit it would seem – before replying,

“I’m offering up my soul - there are hundreds of demons who'd love to get their hands on it. And your friend could be the one holding it. All you got to do is bring my brother Sam back. And give me twenty years. I know it’s usually ten, but with the amount of demons that want it, I think twenty is the steal of the century.”

The demon nodded thoughtfully, before shuffling through his papers,

“Resurrection? That’s easily do-able, just got to find the paperwork.”

He pulled out one of the pages, quickly scanned it and attached it to a clipboard before pulling out a pen.

“It’s a pretty standard contract, just got to make the necessary adjustments and fill in the names and then seal the deal.”

Dean raised an eyebrow, he was sure enough of his sexuality that he wasn’t totally creeped out by the prospect of kissing a guy, but based on the last crossroads deal he made, these demons didn’t seem satisfied with just a quick peek on the check.

“Right, so it’s 20 years and you want to resurrect your brother Sam. I just need your name then we’ll get the show on the road.”

“It’s Dean.”

The demon looked up sharply, making eye contact for the first time, before asking,

“Sam and Dean. Sam and Dean Winchester?”

Dean nodded, and gave a cocky grin,

“I’d be surprised if you hadn’t heard of me.”

The demon tilted his head to the side slightly and stared at Dean,

“What date is it? What year?”

Dean was somewhat surprised by this question as he couldn’t see the connection to the remainder of the conversation, but was fast losing patience – Sam wasn’t getting any less dead,

“It’s 2007, May 7th 2007, now are you going to do this or not?”

The demon ignored him and had gone back to muttering to itself,

“Three days? No-no-no - Impossible - It’s been centuries! It can’t be him. Can it? Is it him?”

The demon returned his attention to Dean,

“Is it you?”

Dean looked puzzled,

“Yeah, I guess.”

This seemed to confuse the demon further,

“Say something that only you would know.”

Dean gave the demon a weird look – did this guy know he was sounding a bit psycho? – before replying,

“Look man, can we just skip all this bullshit philosophy crap? I just wanna get Sammy back.”

This got the ghost of a smile out of the demon,

“It is you.”