-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: Bloody Mary in her Bloody Mirror Time! Crowley's back for a bit, Alistair makes a surprise appearance (it's not as exciting as it sounds), and a certain demon joins the playing field.

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

The Road So Far (this Time Around)

Chapter 10

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

Dean remembered Bloody Mary. He remembered most of the Urban Legend cases pretty well. One, because they weren't your run of the mill case and they always made for good stories later. And B, they were more often than not a bitch to figure out.

The key to this Mary had been a mirror. He remembered Sammy had summoned her because of some big secret that got Jess killed (and yeah, looking back now, it was obviously the visions he'd been having) and she'd come after him from the mirror she died in front of or something.

Problem number one: Dean knew that secret now. So she wasn't going after Sam. Which kind of messed up the whole 'step ahead of the rest' thing he had been rocking on their other hunts. In theory, being from the future should be damn awesome when it came to hunting. It should make him the most badass hunter around.

Problem number two: It wasn't and it didn't because he wasn't alone.

He had to walk on eggshells about everything around Sammy, and everyone else for that matter. Dean couldn't just go to Mr. Yamashiro's antique shop (he'd yellow-paged it as soon as they got to town) and cut the bitch down. He wouldn't be able to explain how he knew where to go with no research or what the bitch was without digging. So he lied, and he bluffed, and he led their witnesses as much as he could as fast as he could without his brother realizing he already knew the information he was trying to get out of them.

Their other hunts so far had been easier to fake his way around. Half the time they had to wait for specific timing anyway to even use his fancy future knowledge mojo. But this one, he knew where the damn mirror was and how to gank the ghost before she killed any more innocents.

But he couldn't go to it.

For the whole damn case he found himself cursing Cas's name again and again. Twenty-four hours earlier, and he wouldn't have to beat around a thousand bushes. He knew, now, that it wouldn't have truly mattered. Nothing he could have done would have kept Sammy out of the hunting life, twenty-four hours or whole months. But damn it, sometimes he needed to think he could have. That Sam would be at law school with Jess and Dean could go waste this bitch without jumping through hoops, lying to his little brother left and right, and claiming psychic dreams when that didn't cover it all.

As if having psychic dreams wasn't already the biggest damn lie.

His whole life was becoming a never-ending web of deception. Dean knew – knew too well – where that led. It led to a prophet and a kid and a friend, dead in the bunker with his eyes burned out of his head.

God knew (and Hell and the Pagans, and everyone else in the friggin' cosmos) that he couldn't keep this up forever. Not without making all the same mistakes he'd come back to fix.

"So you think she's killing people who summon her with a secret?"

They were in the Impala, driving to Estate Antiques in Toledo while Charlie Patterson sat at home with all of the mirrors in her room covered. Dean had remembered too late who the other victims were, and they'd lost her friend, Jill, to the pissed off ghost. Now Charlie was next on the list. If he didn't have to play a thousand questions right now, he could have saved the bitch prom queen, and the terrified teen holed up in her house wouldn't have PTSD for the rest of her life.

He seriously wanted to punch something. Luckily, they were on their way to a store with a lot of shiny, breakable objects.

"Not just any secret: one where someone got killed." Dean pulled onto the street the shop was located on. Yep, this looked familiar.

Sam gazed blankly out the window as his thoughts inevitably turned to the dreams he'd been having before this all started. The ones he'd ignored that had almost gotten Jess killed. Because of his brother she was still alive, at home in Boston recovering with her parents from an ordeal he was sure the family would never fully get over.

"So what secret aren't you telling me that got someone killed?" Dean pulled into the parking lot outside the store and got out of the car without answering. Sam followed, leaning over the top of the car to watch his brother who was watching the building. "Come on, Dean. I know you're going to summon her; it's written all over your face."

"We should check for an alarm." The older hunter was frowning up at the sign above the store. "I got a bad feeling about an alarm in there."

Annoyed, Sam moved around the car to stop his brother before he could advance on the antiques shop. "Seriously, man. When are you going to tell me what's going on?"

Dean finally looked at him and grinned that cocky, broken smile that was always his tell when he had a lie he couldn't hide but would die before he gave up. "Wouldn't be much of a secret if I told you."

He proceeded to the door, pulling out his lock picks and Sam followed after in a huff.

A few minutes later and Sammy was calling out that the alarm system was down (Ha! He was totally right. The cops had shown up the first time around. Score one for future Dean!) and the two got to work on finding the ghost's stupid mirror in a shop full of stupid mirrors. It wasn't quite the needle in the needle stack Dean grumbled it was, but it still took a fair bit of time to spot the one that matched the newspaper clipping on Mary Worthington's tragic death.

"Dean, over here." The older hunter joined his brother, who stood in front of a mirror that perfectly matched the one from the photo, right down to the whole creep vibe.

"Yep, that's it." He pocketed the clipping and held out his hand for the crowbar.

The beanstalk of a man passed it over reluctantly. "You sure about this?"

Dean raised an eyebrow. "What, you got someone killed recently I don't know about?"

Hurt and indignation fought for control over his brother's face, before he settled on the one that was far easier to express. "And you have?"

'Not yet.' Inner Dean muttered deep within his own mind. Aloud, he rebuked more caustically than necessary and rolled his eyes. "Secret, Sam. It won't be much of one if you keep asking."

Dean started the summoning before Sam could rebuke. He spoke the first two names steadily, but paused before the final call to cast a final 'here goes' look at Sam. His brother rolled his shoulders and raised the flashlight across the dusty surface of the mirror. "Bloody Mary."

The two stood in silence, one with crowbar raised and ready for a homerun swing, the other an unwavering light on the reflective surface, just waiting for the ghost of Mary Worthington to show herself.

There was the inhale to his left, slow and shaky and screaming creepy ghost woman. Dean spun, but it was only his own reflection watching him in the many mirrors that surrounded the two hunters.

"Dean!"

"I know, I know, stay on her friggin' mirror." Another breath sounded and he swore he could feel that one on his skin. He spun again, crowbar kept tight to his body so he didn't swing the thing into Sam. Still, only their own reflections stared back.

"Where is she?" Sam's eyes darted to the other mirrors, snapping back to Mary's when he saw movement out of the corner of his eye. But there was nothing there. "Dean, do you see her?"

The older Winchester didn't answer, and Sam cast a worried look his way. His brother wasn't moving, standing stalk still in front of a mirror, staring at himself like it was the very ghost they were hunting.

"Dean?"

"No. I won't," he whispered, breathe catching even as he did and that was all Sam needed to round on the mirror his brother was standing on front of and smash it to pieces with a couple hard blows with the butt of the flashlight. Dean broke out of his trance and stumbled back.

"Shit, Sam, the mirror!"

"She wasn't in it!"

Dean turned to find the source reflection but drew up short at the sight of himself ten years from now. No. Not ten years. More like eight and an apocalypse later. So much more like 2014 Dean, who was cold and hard and bitter and sent his best friend and his crew to their death for a god damn distraction. A Dean who had lost his brother to the Devil.

Green eyes stared at him with such hatred, such disappointment that it took his breath away and sent pain shooting through his head like a physical blow.

"You're going to get them all killed."

"Shut your mouth."

"You're nothing but a screw up, Dean. You and me? We only know how to make things worse. The whole world's gonna burn, and this time it'll be all your fault."

"Shut up, you son of a bitch! I'm not you!" He charged the mirror with the crowbar and, in a show of excessive force, sent the frame tumbling backwards to crash into another mirror, cracking that one on the floor.

"Dean!"

"Find her, Sam!" He stumbled with a gasp, putting a hand to the side of his head. God, he had a killer headache. He heard his brother smash a mirror, and then another, calling out to Mary, daring her to go into the one they needed. But Dean couldn't focus. His head felt like it was swimming in a damn punch bowl. He fell to his knees and the crowbar clattered to the ground.

He clutched at his chest. His heart was racing like a friggin' freight train. Pain laced through him on every slamming beat and he felt something warm and thick sliding down his cheek. Shit.

"You're going to hell, Dean." The hunter's breath hitched and his head shot up, pain arcing across the inside of his skull to shoot down his spine. His reflection towered over him, staring down on him in disregard.

His eyes were pitch black.

"You're going to hell, again. And this is what you're going to become."

Blood soaked fingers dragged his sleeve up, leaving red streaks across his skin like a sick finger painting: a trail that led straight to the mark of Cain. It burned hot and angry on his forearm.

"N-No…" Dean couldn't look. He dropped his head and watched blood drip to the floor beneath him. Crap, this was so not going to plan.

Sam's flashlight went through the mirror, shattering Demon Dean and raining shards of glass on the collapsed hunter. The flashlight hit the ground with a clatter and the younger Winchester left it, abandoned, to grab Dean beneath his arms. He hauled him back and away from the mirrors as glass clinked and cracked in their wake.

When they were a couple feet to safety, the sasquatch bent down and hauled his brother up with an arm wrapped over his shoulder. He didn't make it a yard before he heard glass crunch behind them. The hunter glanced back over his shoulder, body tense and spine rigid.

Mary Worthington was climbing out of her mirror like something out of a nightmare. Only much, much worse because this was very real.

"Shit!" Sam muttered, dropping his brother on the ground with a grunt as he dove for the abandoned crowbar. If nothing else, it had iron in it.

His hand had just wrapped around cold metal when he felt it. The blood rushing to his brain, the pain filling his head like a cup soon to overflow. Sam tried to keep his grip on the weapon, tried to raise it to the ghost straightening up and stalking towards him and his brother. He could feel the blood leaking from his eyes, could feel it filling his nose and throat.

"S-Sammy," he turned, but it felt like it took a lifetime. His brother was staring at him from eyes squinting past blood and pain. He was trying to point at something. "Mir-mirror. Use a mirror."

Sam turned back to the ghost, feet dragging across the glass-scattered floor. She had a jagged piece in hand, clenched around a bloody fist and poised to kill. He looked to his left, where an intact mirror was lying on its side. With a deep breath, he grabbed at the thing and struggled to hold it up, praying to God that they could turn her vengeful justice on herself.

Because if not, they were screwed.

Mary choked on her own screams and cries of sin, clawing at her face to hide from whatever it was she saw in the mirror's surface. She writhed and bent in on herself, folding into impossible tightness before she collapsed into nothing more than a pile of blood.

The pain immediately drained from his head and Sam fell to the ground. He wrapped his hand around the crowbar once more and proceeded to smash the mirror to pieces.

Dean stumbled to his feet and made his way to Mary Worthington's mirror. He kicked it hard, nearly losing his balance. The mirror fell to the ground, cracks spiraling through it and breaking the smooth surface.

"Bitch," he muttered as he turned around to look at his brother. He slid to his knees, wincing at the glass biting into his legs.

Sam huffed out a laugh, sitting back on his heels and looking at the destroyed shop around them. "This has to be at least a century of bad luck."

"Just what we need." Dean laughed, stopping to spit out a mouthful of blood, but laughing all the same.

That was, until they heard the sirens in the distance.

"Shit," the older of the two muttered, pushing himself up again and grabbing his brother to help him stand. "Someone must have heard the showdown."

"We weren't exactly subtle," Sam chuckled back, grabbing the crowbar and the flashlight as they raced out of the store. They had to take anything that might have their prints. But damn, was bending over a bad idea in his current state.

"You know how to smash a mirror quietly and didn't tell me?"

He grinned at his brother as they hobbled as quickly as two people covered in blood and nearly dying of an aneurysm could. Neither should probably be driving, but it wasn't like they had much of a choice. Dean put the Impala into drive and the two hauled ass away from Estate Antiques before the cops showed up.

-o-o-o-

They were pulling off the main highway and into the hotel they were camped at for the night when Sam started the conversation he knew his brother would fight tooth and nail to avoid. The older hunter turned to him expectantly as he put the car in park. There was still a streak of dried blood across his left cheek and the corner of his eye, despite his best attempts to wipe at his face with the sleeve of his jacket.

"Dean, who is it you think you got killed?"

Dean Winchester stared at his brother, honestly debating what to say. He knew what he had to say, but it wasn't what he wanted to say. He wanted to tell him the truth. Or at least, he didn't want to lie to him again. Didn't want to cause that look in his eyes when he thought his big brother didn't trust him.

But he didn't have much of a choice and it looked like time was damn determined to repeat itself in some ways no matter what he did. It friggin' sucked.

"No can do, Sammy." He gave a weak-ass smile. The one that said he knew what his brother wanted, but couldn't give it to him. "If I told you, then I'd have to kill you."

Sam looked pissed at him making light of it, but it was a misdirect that would keep him from digging deeper, at least for now. He certainly adopted that expression that said he knew Dean didn't trust him. But he didn't say much, just settled back with a full grown man's pout and indignantly insisted, "It's Sam."

"Course it is."

-o-o-o-

The masses of Hell would be muttering and whispering for weeks. Something was up. Something was coming. Two meetings by the powerhouses of Hell in less than a week, and not one of them had tried to kill the others. It was unprecedented.

And none of the three aforementioned leaders of the Underworld were happy about it.

"He knew my name. They summoned me by my bloody name!" Crowley was spewing in his anger, red faced and hair out of place from constant tugging. He had been pissed as soon as he and the barmy yellow eyed bastard returned to Hell.

Azazel, far more calm and composed, had suggested an emergency meeting with Lilith. She brought along her top torturer, much to the displeasure of everyone involved.

"And then, to top it off, this bastard agrees to my head on the chopping block!" The King of the Crossroads thumbed at his companion, as if the motion itself could somehow stab Azazel through the heart and rip his life force out to roast on a spit.

He was just a little displeased by current events.

"Quit your whining, Crowley." Alastair looked at the other man with great displeasure and more than a little disdain. The day to day dealings of Hell and Earth were below him. He had humans to be breaking; his talents were far more needed elsewhere.

The crossroads demon sputtered and the purpling of his face promised both retribution and possible self-asphyxiation. Whichever one happened first. "Whining? 'Whining,' he says!"

"Enough." The gathered men turned their attention at the powerful command coming from such a small body. Lilith regarded them all like idiot children she hardly had the time to discipline. "Clearly, Dean Winchester is getting information from someone."

"There's been no movement at the gate." Azazel was as calm and indifferent as always. Perhaps that was why their Father had picked him to start everything. "It's not Heaven."

"Then a pagan," Lilith supplied, looking less than pleased. While it was a far better situation than the cloud-hoppers, she hated dealing with those primitives. "We anticipated the lesser deities taking offence at us ending the world."

She said it so casually. Crowley might have found entertainment in that, if he wasn't still boiling over (and rightly so, might he add). Of course, the best part was that she was missing the most likely category of saboteur to their little party. The category he, himself fit into when he wasn't busy playing his part as an officer in the Apocalypse Club.

"Or a demon." Alistair seemed unaffected by the treason he so easily suggested and Crowley resisted glaring daggers in his general direction. "A traitor would benefit greatly from the power struggle a coup would cause if Lucifer fails to rise."

The little girl and current Queen of Hell balked. "A coup? You're suggesting some demon thinks hunters can stop us? Let alone kill…who? Me? Azazel? You? Don't make me laugh, Alistair."

Crowley had to use all his not insignificant self-control to ignore the way she casually passed him over on that list. Oh, he could not wait for the day the Winchesters put this bitch's head on a spike. He might even offer his services. Perhaps he could suggest a few targets for that new gun of theirs.

Hell's top torturer just shrugged. He could care less what happened. Whether Lucifer rose or not, he would get to continue his work and that's all that mattered to him. "You've underestimated the Righteous Man once before, look where that got you."

Lilith seethed through gritted teeth and small fists. She spun on Azazel, who regarded her with little change in expression. "Pull your girl off of John Winchester. Get someone else to track him down. I want her saddled up to Dean and finding out who or what the hell is helping him."

The yellow eyed demon shrugged in acquiescence. His eldest was the best of his children, and Dean was a serious demotion for her skills. But arguing with Lucifer's First was useless when she was like this.

He had little doubt his daughter would wheedle her way past the obvious holes in the hunter's defenses in less than a week. Finding someone else to get to John would be a challenge, though. He was a resourceful human, capable of giving even Hell's best the slip. If she was having trouble finding him, it was unlikely any of his other children would fare better.

As the meeting broke up, Azazel pondered an option he had not previously considered. He hadn't needed to. But it looked like their timetable was speeding up, and that would require more…aggressive planning.

Perhaps it was time to take a page out of Dean Winchester's book. There were more than a couple pagans and monsters with skill sets far more suited to tracking than a demon's.

-o-o-o-

Over the next couple of weeks, the brother's fell into an easy routine. Find a hunt, kill the monster, rinse and repeat. Sometimes rinse really, really, really well. God, Dean had not needed to relive the bug curse ever, ever again.

He'd been worried at the beginning – damn near gave himself a panic attack actually – about not following their steps exactly as they had the first time. What if they missed hunts where they had saved people? What happened to those souls this time around? And how screwed up could he make the timeline before he started seeing consequences? What was one life, versus stopping the apocalypse?

The nightmares generated from those questions alone were enough to keep Dean up most nights.

It happened on occasion. Of course it happened. The older hunter couldn't remember every hunt they'd been on, try as he might, and some he could remember the monster or a memorable moment, but not enough of the important details to track the case down. Especially when, more often than not, he couldn't recall when or where it would happen.

They'd roamed the country last time, checking news articles and obituaries and making their way hunt to hunt. There was no way to say which newspapers they'd picked up, which town they were in when they found their next case. He tried to go by instinct, but in reality it was a fucking guessing game and there was nothing he could do when he got it wrong.

The lack of déjà vu was always his first clue.

It sucked how badly he hoped for it now, how he started the mantra in his head when they entered whatever nameless town was in need of saving. A silent, repeated prayer, begging for the trippy sense of familiarity to start any second now. Because going without it meant they'd done something different this time around. It meant innocent people they were supposed to save were going to die instead.

It was another drop in the cup of changing the future and Dean wasn't sure how full that cup was, or how much it could hold from the start.

The older hunter never knew what monster they had missed or where he'd messed up (had he skipped a local newspaper? Decided to turn left on the highway when last time he went right? Had he distracted Sam with some inane joke right at the moment the kid would have found the hunt?) He lived in complete paranoia the first week after the Wendigo as they looked for their next gig. Eventually Sam threatened a mutiny over driving rights and a trip straight to Bobby's for a break and possibly a head check if his brother didn't calm the hell down and relax.

Luckily, Sam seemed to think it was the whole 'demons want my little brother on a silver platter' anomaly causing the odd behavior.

So Dean caved and forced himself to let whatever would happen, happen.

Besides, if Time wanted so badly to walk the same road, then it could deal with the cleanup whenever Dean fucked up.

Right?

-o-o-o-

He knew the second she kissed him that she wasn't human.

She was gorgeous. Never-ending curves and full breasts, everything just barely contained in the sinfully tight jean skirt and cut off top that perfectly fit the dive bar they were in. She even had the cowboy boots that screamed 'kinky.' Sex was clearly on the menu tonight, and up until she'd locked lips with him, Dean had considered ordering the full course meal.

He'd never kissed a demon hiding behind the face of a human before: only the crossroads demon, and he'd known what he was getting himself into with that one. The background taste of sulfur in this demon's mouth was unmistakable, though, and stomach-turning. How the hell Ruby talked her way into his brother's bed tasting like that, he'd never know.

They managed to play it cool. He signaled to Sam that something was up in the same line he used to invite the woman back to his place. Sammy rolled his eyes appropriately and didn't bother watching them leave with her draped over his brother like silk. They made their way out of the bar and started the block and a half walk back to the motel. He stalled for time using every other walled-surface as an excuse for heavy groping, selling it hard.

Next gas station they stopped at, he was buying out their supply of mouthwash and toothpaste.

Sam was already in the room when they stumbled in. She was stripping Dean of his jacket when he stepped out from behind the door, a bottle of holy water in one hand and the Key of Solomon in the other.

"Shit." She didn't even try to deny it as Dean took three hasty steps out of the devil's trap spray-painted into the crappy carpet. Yeah, their fake credit card was definitely getting charged for that one come morning.

He wiped his mouth on the back of his hand but it did little to chase away the foul taste still clinging on his tongue. The bitch crossed her arms, borrowed face full of disbelief, anger, and amusement all wrapped up in a smirk that was eerily familiar to Dean. He didn't recognize the woman playing host, and it was kind of hard to tell demons apart by facial expressions alone. They pretty much all had the same basic personality, bought on discount at 'Evil Villains and Cliché Monsters Co.', just ratcheted up to different levels.

Sam started the exorcism and the woman sneered.

"How'd you know?" She directed her question at the older Winchester with a hint of a smirk. The demon was clearly pissed, but in a calm sort of way that screamed 'cat' in the canary-who's-about-to-get-eaten scenario. Which put Dean on edge, considering he and his brother were definitely supposed to be the cats here.

He got the uncomfortable feeling that he had, in fact, met this demon before.

"You taste like sulfur, bitch."

She laughed, even as she choked on her own black essence.

-o-o-o-

"Why would demons still be after us?" Sam let out a frustrated noise as they packed up and hit the road, not daring to stay overnight in a town where demons had found them. Dean climbed into the driver's seat, wondering if he still remembered the ingredients for those Hex bags Ruby always gave them. With the bunker proofed seven ways to Sunday, it had been a while since he made one. "I thought we had a deal. I'm hunting!"

The older brother just shrugged, less surprised and far less concerned about Hell being on their six. It was kind of expected, actually. "Deal didn't say anything about them leaving us alone. Just Jess. Besides, whatever Yellow Eyes wants you for is big. I'm not surprised they're keeping an eye on us."

Sam looked less than happy at that.

-o-o-o-

It was in Indiana they caught trail of a skinwalker, or what they thought was a skinwalker. Dean wasn't sure as nothing memorable was coming up about this hunt. They'd have to see what John's journal said, since he was pretty rusty on the monsters.

"Wait," Sam pulled up short on their way back to the Impala. Surprise was written all over his face. "You have Dad's journal?"

"Yeah, it's-" Dean stopped. Because it wasn't in the trunk. He'd done inventory back in Stanford and again before they left Boston for the wendigo hunt. Its absence hadn't occurred to him then but it sure as hell did now. He thumped his fist on the roof of the impala and resisted the urge to swear like a sailor.

Dad's journal was in a box in the evidence locker of the Jericho Police Department.

Son of a bitch!

-o-o-o-

"This is a terrible idea."

"For the thousandth time. Shut. Up."

Dean stretched his arms up as far as he could, flashlight held between his teeth, as he worked the edge of a knife under the sill of a second story window of the JPD.

Okay, so this was a terrible idea. Breaking into a police station was easy pickings for Ten-Years-From-Now Sam. But Fresh-Out-Of-College Sam lacked the confidence and still held enough sanity to realize breaking into a building full of cops was a really terrible idea. Which made him a horrible breaking-and-entering partner.

Technically, Sam wasn't breaking in. Dean was. His gargantuan brother was just acting as support. Six and a half feet of it.

"Are you sure this is how we did it in your dream, Dean?" the whiney moose whined, wincing as Dean purposefully dug his heel into his giant shoulders.

"Just shut up and lift, Sammy. I've almost got it."

"It's Sam."

Dean was gonna kill him. Right after he covered his loud mouth in duct tape.

"Right. Sam. Short for Sam-fucking-amantha. The whiniest bitch in all of-" The latch lifted with a click and Dean broke out in a grin. "Aha! Got it!"

He hoisted himself up, reveling in his young, strong muscles. Dude, growing old sucked. He wiggled his way through the narrow window.

Sam breathed a sigh of relief as his brother's feet finally left his sore shoulders. He was going to have bruises. He watched Dean pass through the window, shoulders then torso and hips. Suddenly, he disappeared altogether with a crash and a muffled yelp from the other side of the wall.

"…Dean?"

A hand waved floppily at him through the window. He heard another crash and several expletives as Dean made his way out of the supply room.

This was a terrible idea.