-Summary: It's the end of the world and they've got one last card to play. Castiel sends Dean back: back before everything. Now he has time to stop what's coming, but no friggin' clue how to do it. Time travel should really come with a manual. TIMELINE AU

-Chapter Warnings: Dean's still swearing. It's likely safe to say he'll be swearing for the rest of the foreseeable (and unforeseeable) future. Oh, and Jess is a pretty cool chick.

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The Road So Far (this Time Around)

Chapter 3

-o-o-o-o-o-o-o-o-o-o-o-o-o-o-o-o-o-o-o-

With an unceremonious shove, Dean ripped the hood off of Brady as the demon stumbled into the devils trap. It wasn't so much a hood as it was an old white t-shirt he'd ripped up and tied back together. He'd drawn the devils trap with a sharpie while waiting at the bar. Yeah, yeah, it wasn't as nifty looking as the one Crowley had bagged him with, looking like a burlap sack he found in a re-enactment of Children of the Corn, but his version was improvised. Which made it even more badass, in his opinion.

Brady managed to stay on his feet, letting out a low chuckle with his back to the two brothers. He titled his head to the sky and laughed. "Oh Dean," he turned around with a smile, "you're a lot smarter than we thought. When did that happen?"

"Bite me."

Sammy was watching him again, switching between him and his former best friend. The look in his eye was suspicious, but not of what Dean might be. He'd proven himself human enough for the hunter. No, Sam was sure his brother knew more than he was saying, and he'd get it out of him one way or another.

Damn it, why couldn't he have just stayed out of it.

Because he's a Winchester.

Another memory surfaced, of a week spent in a suit and tie, starving on rabbit food smoothies and hunting a crazy ass ghost of a long dead boss with one, Sam Wesson.

'Hunting is in your blood. It's what you are.'

Friggin' Zachariah. And friggin' Time. Well screw them both. Sam wasn't going to be a hunter, if it killed Dean.

"You know, you're real lucky, Sammy." Brady was talking again, this time smiling gently – kindly – at the younger of the two. The demon turned to Dean, tilting his head mockingly. "Maybe luckier than even your brother realizes. He spared you quite the nasty shock."

"What are you talking about?" Sam turned to his brother. "Dean, what's he mean?"

The older Winchester considered shutting the demon up: exorcising him before he could no doubt taunt and stab at his brother over what he had been about to do. But Sam wouldn't just let this go. It was cruel to let his little brother hear the truth from a demon, but maybe it would be better coming from something he could take his anger out on.

"I'm talking about that fine piece of ass you have waiting for you back at home."

Sam straightened, shoulders going rigid. His hands fisted involuntarily, shaking with fear and anger equally.

Brady showed his pearly whites. "And how I was going to pin her to the ceiling and burn her to a crisp."

The younger hunter when white. Brady laughed.

"That's right, Sammy-Boy. Just like mommy dearest."

Sam opened his mouth, but nothing came out. He looked desperately to Dean, searching for the voice of reason that said none of this was real. One look at his older brother and his world came crashing down.

"This- This is-"

Brady tilted his head back and howled with laughter. "Surprise! I'm the monster that killed your whore mother!"

"No, he isn't," Dean said at the same time.

The silence in the clearing would have been damn near comical if it was any other situation. Two sets of wide eyes turned to Dean, asking for answers he wasn't going to give either of them.

Brady was the first to recover. His eyes were narrow slits as he stared down the man who all their sources had said was the hothead of the two. The one who would react the most to everything he was saying.

"You think I didn't pin the bitch to the ceiling, Dean? You think I didn't gut Mommy Winchester right above little Sammy's crib? I watched her burn and I'm gonna do the same thing to Jess-"

Dean took a menacing step forward, cocking the shotgun. His hand twitched to wrap around an angel blade and kill this son of a bitch.

"The thing that killed our mom had yellow eyes. You gonna pull out those pale babies? Or are you gonna shut the hell up, cuz I know you don't got shit to show."

Brady's mouth slowly shut, a glare settling over his features. His eyes remained human, and Dean took it for the win it was.

He was beyond ready to waste this son of a bitch before he could run his mouth any more, but he needed to let it play out. No way Sam would ever let it go if he didn't learn all he could now. The only chance Dean had of getting his brother to drop this whole thing was if he felt it was over. Closure and all that crap.

"You're right," Brady's voice brought Dean back around.

The man was shrugging his shoulders, but his eyes had a glint of new strategy in them. Guess he was of the brainy persuasion of demon rather than the brawn. Probably had to be at least halfway intelligent to land an espionage gig watching over the future vessel of Lucifer himself.

Dean tightened his grip on his gun.

"I'm not the one who put the hit out on your mommy. Or Jess. But I'm still the one who's gonna light her up."

He directed his last words at Sam, who looked like he was half a step away from throwing himself into the devils trap and beating Brady with his bare hands. Dean reached out and gripped his shoulder. Sam flinched, but didn't pull away.

Dean turned to the demon. "Maybe that was the plan, but not anymore. You're going right back to Hell."

The answering grin would have put Hannibal Lecter to shame.

"You think this ends with me, Dean-O? Oh, no. My boss isn't going to stop. Go ahead, send me back. It won't save her, and it won't save you." He turned his burning eyes to Sam. "My kind is never going to stop. Jess is going to burn. She'll be dead by the end of the weak and it's going to be all your fault, Sammy!"

Dean grabbed his brother as he let out an animalistic roar and charged the circle. He threw him back, yelling to back off – that playing to his game wouldn't do anything but give him the satisfaction. Not to mention possibly break the trap and set him free.

Sam stalked off, fuming. He paced back and forth by the impala, fighting to cool off and clearly losing if the menacing glares he sent their way every thirty seconds were any indication.

Dean looked back at Brady. The demon just stood, smirking like the fucking asshole he was. The hunter looked away, focusing his anger and frustration at an object he was less likely to pummel into the ground.

Son of a bitch. Son of a bitch!

He honestly hadn't thought it. Kill Brady, save Jess. That had been the equation and this was his solution. Simple, two step problem. Only Azazel had ordered Jess killed to get Sam back into hunting. He wouldn't stop until his 'favorite' had the motivation needed to follow a road of blood and death. Right now, Jess was still their best bet at getting Sam on the path to become a cold, revenge-filled hunter.

She would never be safe unless he took that road.

Why hadn't he realized it? Why had he thought anything would be this damn simple? It was the voice in the back of his head that did it, that pushed him over the edge. It whispered, 'Well, at least you won't be alone anymore. Sammy'll be right back by your side. Straight to the end of the world.'

It was the last straw on his already precariously balanced emotional state.

Dean let out a primal scream and slammed the butt of his shotgun into the nearest tree. He did it again and again and again, but nothing got better.

"Dean! Dean, stop!" A giant's hand gripped the barrel of the gun: another pressed against his chest. His brother's face swam into view, concerned and angry and still so fucking devastated.

Dean shoved away from him, giving up the shotgun to his brother's tense grip and raising his hands in a show of calm. "Okay," he muttered. "Okay."

He gave himself a second. Told himself to get it back under control. He could lose it later, right now they had a job to do. Dean straightened his jacket and stalked back towards the grinning son of a bitch. Sam followed.

"Get whatever you want out of him." He stopped at the edge of the circle, leveling the demon with his most intimidating glare. It was a look shaped in the depths of Hell. It made even demons take a step back. "We're sending this son of a bitch back where he came from."

Sam spared a second to watch his brother, a dark man he wasn't entirely sure he recognized, before focusing his attention solely on the thing sitting in his best friend's body.

Brady didn't say much. At least nothing of consequence. He spouted shit about having plans for Sammy, that he was their favorite, that Jess would never be safe again. He never shut up, actually, but he didn't say anything either.

Dean kept half an ear out for lies, setting them straight when he could without giving too much away. There were surprisingly few.

He doubted the low-level minion even knew the real play at this point. Nothing came up alluding to Lucifer or Lilith. Brady kept Azazel's name to himself, always calling him Boss, and anything else he knew of any importance was danced around with the dexterity of an experienced liar.

Dean knew he could have gotten it out of him. Even without Ruby's knife or an angel blade, he could have made the demon sing. He had a weapon time couldn't take away from him. But he was pretty sure he should keep that whole 'I can torture information out of just about anyone or thing' to himself this time around.

Sam was already looking at him like he was considering having him institutionalized. No need to give the kid more fuel.

Eventually, frustrated, Sam called it. His shoulders were tense, his hands still fisted and shaking, but his face was stone when he started for the car to get his laptop and search for an exorcism. Dean couldn't help it. He stopped his brother with a pat to the chest, winked at the giant, and started reciting the Latin he knew by heart.

The shock on Sam's face was totally worth it.

The demon inhabiting Brady went kicking and screaming, but eventually collapsed in a choking, hacking explosion of black smoke. The plume was dragged into the ground and sent, presumably, back to the pits of Hell.

Good fucking riddance.

The kid that was actually Brady was, shockingly, still alive. With a few broken fingers, a bit of skull trauma, and probably screwed in the head seven ways from Sunday, but alive.

"We should get him to a hospital," Sam said quietly, carrying the unconscious body back to the Impala.

Dean just nodded, not asking what story they were going to give. He knew this couldn't be one of their drop and runs, like they usually did with civilians. This was Sam's friend. He listened with half an ear as Sam told the ER nurses of Brady's past drug abuse, of how he found him half alive on campus, suspecting a relapse and maybe a mugging gone bad. He waited until his brother sunk into the hard, plastic chairs in the waiting room to say anything at all.

"Sam, we gotta go."

The kid looked up at him with those puppy dog eyes and Dean hated himself a little more. "What?" He looked around at the other friends and family in states of distress, all waiting to hear about a loved one. "We can't just leave."

Yeah, it would be suspicious as hell, not that that's what Sam meant. But they didn't have the time or luxury to stick around.

"Sam."

His brother met his gaze again and swallowed as the reality of what had happened set it.

"I…We can't stay here, can we?"

Dean knew he wasn't talking about the hospital. He shook his head. "That demon will have gotten word to Yellow Eyes by now. Or will soon."

Sam was up in the blink of an eye. "Jess."

Dean put a comforting hand to his brother's chest. "Is in a demon proofed house at the moment. I, uh, made some additions."

Sam looked relieved, but only so much. She may have been safe, but it was momentary. They would still have to leave. He didn't know where they would go. Where could they run to that demons couldn't follow? His mind flew through every place and dozens of plans, but he didn't have the answers, and that scared him to his core.

The two waited until the nurses at the front desk were looking away, and then took off. Dean kept it under the speed limit, but just barely as they headed back to the apartment.

Sam sat in the front seat of the Impala and tried to figure out what the hell he would tell Jess to convince her to leave town with them without freaking her completely out. He wasn't coming up with much, and panic was twisting his chest into knots.

As they hit a red light that Dean was sorely tempted to run, Sam quietly said, "She's never going to be safe, Dean. We can't- we can't run forever."

Dean rapped his knuckles on the steering wheel impatiently. "We'll take her to Bobby's. She'll be safe in the panic room. And we'll go from there."

Sam's brow furled and he finally looked at his brother. "Bobby has a panic room?"

God damn crap on a cracker. Dean ran a hand down his face. He was going to make a list of what they did and didn't know in 2005. First thing, soon as they were at Bobby's. That's what he was gonna do. Make a god damn list.

Instead, he forced a smirk onto his face and answered cockily, "Yeah, Sammy, Bobby has a panic room. See what happens when you run off to get an education? You miss learning the good stuff."

"Jerk," Sam said on impulse, rolling his eyes. "And it's Sam."

"Right. Sam." Dean nodded. The light turned green and he hit the gas. "Bitch."

-o-o-o-

Jess took it pretty well. At least, as well as a civilian with no clue as to what was going on could take her boyfriend coming home in a half panic, packing their bags, and insisting they had to leave. The usual questions came up: Does this have something to do with your father? Your brother? Sam, what is going on? What aren't you telling me?

For Sam's part, it was clear he didn't know what to tell her, so he didn't tell her anything. He said they were in danger, that they needed to leave, and he'd explain on the way.

All in all, they were in and out in under forty-five minutes. Dean kept guard at the front door ("Is that- is that a shotgun? Sam, why does your brother have a gun!") and escorted the two with their bags back to the Impala. Nothing came out of the shadows after them. He kept a careful eye on the rear view mirror for the first three hours of their drive.

Either Azazel had gotten slow, or he was waiting this out to see what Sam's play would be.

The younger Winchester sat in the front seat, a flask of holy water in the side door and a sawed-off under his feet. Despite the urge to keep it in his lap, ready at a moment's notice, there was no need to freak Jess out more by calling attention to it.

Jess was in the backseat, body language screaming 'freaked out' but facial expression surprisingly controlled. Her eyes kept darting between her boyfriend, his legs that were stretched out over a gun (yes, she had noticed that little fun fact, thank you very much), and his brother.

She knew Sam had issues with his family, especially the family business. She had always thought he had a controlling father, possibly abusive, who couldn't let his son live his own life. Privately, she'd been proud of him for getting away from that, even if she hadn't known him back when he'd made that choice. Now, staring at the duel hardened expressions of both brothers and the freaking guns within reach of both, she was wondering just how off base she'd been.

Sam had come home in a surprisingly somber variety of panic and Dean had been on them the entire time like a professional bodyguard.

Just what the hell was his family business?

"Sam," she began softly, worriedly. She glanced at Dean – the wild card in all of this. "I think you need to explain everything to me. Right now."

Her boyfriend looked over his shoulder at her. He looked wrecked. She knew this man – she loved this man. And whatever was happening was hurting him. But telling her was hurting him more.

"Jess, I- I can't," he said, keeping her gaze. His brown eyes were wide, begging her to believe him. To forgive him.

"Sam."

Dean's voice called both their attentions. There was a silent conversation there Jess didn't understand, try as she might. But Sam obviously spoke the language.

"Dean, no." He shook his head and leaned towards his brother, lowering his voice as if she wasn't less than a foot away and hearing every word. "Are you kidding me? Family rule number one: we do what we do and we shut up about it!"

Oh yeah. This was boding so well.

"What are you going to do?" Dean asked mockingly. "You going to lock her in the panic room without an explanation? Sammy, it's in the basement. It looks like a friggin' war bunker out of a horror movie. She's going to think we're serial killers."

And there it was. She had been trying really, really hard to stay away from that particular train of thought. Not that Dean, with his scary glares, militaristic guarding, and fucking shotgun, had been much help in that department.

"I am right here, you know!" she practically yelled. And if her voice went a few octaves higher than she intended and possibly edged towards the screechy levels of hysteria, well, they could both just fuck off about it.

"Jess." He was looking at her again, puppy eyes ranked up to full blown ten.

"A demon's coming for you."

"Dean!"

"It's after you to get to Sam."

"Excuse me?"

Her boyfriend looked ready to punch his brother, who gave him a quick 'tough luck' glare. "You can't hide it forever, Sam. Eventually you get to the point where the 'truth is out there' spiel is the only option left."

Sam gritted his teeth. "We weren't there yet."

The leather of the steering wheel creaked under Dean's knuckles. He didn't look at his brother again, instead checking the rearview mirror before re-focusing on the road. "Yeah, well, we will be soon enough."

Sam glanced in the side mirror, but didn't see anything behind them. Not even distant headlights of another car on the road. His finger itched for the shotgun on the floor, but he resisted. It would do more harm than good.

"Somebody want to fill me in?" Jess was practically shaking in the back seat, but it wasn't from fear. "A demon? Please tell me that's some screwed up metaphor for something."

Sam let out a heartbreaking sigh and rubbed his forehead. "It isn't." He said it with so much defeat in his voice, Jess had half a mind to believe him on the spot.

"Okay," she worked through slowly, trying to reason out how else the word 'demon' could apply. "Is this, like- Is this some sort of….criminal? Like a hitman? Sam, is your family- are you part of the mafia?"

She'd heard of stranger things, and 'the Demon' was something she could see the mob naming one of their boogiemen. Of course, she wasn't well-read on the subject outside of the occasional movie night, so 1950's New York was pretty much all that came to mind. Try as she might, Jess couldn't picture Sam coming from that sort of environment.

Maybe an ex-con? Or a serial killer. Maybe Sam's family had been put into Witness Protection. His mom had died when he was a baby. Maybe she'd been murdered and his dad and brother had testified? It would explain the current situation, but not so much his hatred of the family business.

A bark of laughter from Dean and a silencing glare from Sam ended her wild speculation.

"We're not in the mafia, Jess."

"We're hunters." Her boyfriend looked once more ready to strangle his brother, who shrugged. "We chase down supernatural badasses that kill humans."

Silence reigned in the Impala. Jess was staring at Dean. Dean was staring at the open road. Sam was trying to disappear into his seat. She had no idea how to respond.

"Sam?" The whisper was quiet. Questioning. Praying. He flinched, but ultimately gave a defeated sigh.

"It's true."

"But…" She gripped the back of his seat. "That- That stuff isn't real. Sam, you have to know that stuff isn't real."

Suddenly the conversation they'd had a few nights ago about Halloween took on an entirely new perspective.

Sam sunk into his seat and closed his eyes. He wondered miserably if this was the last time he'd talk to Jess as the man she loved, and not the psychotic mental patient with severe psychosis who she had run away from, screaming.

"Sam, you got your ID on you?"

The question, such a non-sequitur to the current tension in the car, startled him out of his misery. "What?"

"An ID. Do you have one on you?"

Sam crinkled his nose in confusion. Dean would have called him out on the bitchface in any other situation. "Yeah. Why?"

The impala jerked to the left as Dean hit the brakes, pulling off the highway to make a sharp turn down a dirt side road. Sam grabbed at the dash to steady himself. Behind him, Jess's fingers dug into the edges of his seat.

"Dean?"

His brother didn't answer, just continued down the dirt road through fields and farmland. They passed a picturesque farmhouse, white curtains framing every window, backlit with warm yellow light. They drove for another ten minutes, with Jess in the backseat praying she wasn't about to find out her boyfriend was a reluctant serial killer, egged on by the anti-religious delusions of his brother. Or any variation of that nightmare.

Dean stopped the car as they came to an intersection of another road. He climbed out and headed for the trunk. Jess didn't dare leave the safety of the backseat. Sam tried to send her a reassuring look (it really didn't work) before climbing out of the Impala after his brother.

"Dean, what are we doing here?"

He caught the spray paint when it was thrown at him. Dean shut the trunk, shaking a can of his own as he rounded the back of the car. In his other hand was a cigar box.

"We're gonna summon a crossroads demon."