-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

-Quick Reminder: For anyone who hasn't read the prologue to this in a while, I wrote it as an AU to the Season 11 ending, where Amara was losing the fight but pretty much everyone was already dead. It comes up in this chapter, hence the reminder, so no one is confused when Dean says it.

-Chapter Warnings: More talking! Time to catch Bobby up on everything that's coming. Well, everything accept maybe that selling his soul bit. Okay, and the releasing Lucifer part. And probably the losing Sam to the cage bit...Maybe he'll just tell Bobby the next five years are super peachy. Everything's fine, nothing to see there.

-Actual Chapter Warning: It's been eons since I mentioned in a warning that this story is Slash (Destiel). As you may have noticed, it's just about the slowest burn ever. And even when we do get there, I'm not much of a romance writer. I like a good romance subplot, but I'm action first and foremost. So it'll always be a nice added bit, but never the main focus. Anyhoo, we FINALLY have our first teeny tiny itsy bitsy mention of pre-slash destiel. Lol. Figured I'd be super cautious and warn you all about it anyway.

-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 23

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

"So…"

The two sat awkwardly as Bobby tapped the pen against the legal pad and Dean stared at his beer as if everything could be blamed on the poor bottle of suds.

"Angels?"

God, Dean did not want to have this conversation. No matter how well Bobby was handling it, talking about what was coming meant dredging up so many bad memories. Memories that the hunter now felt he was pretty much damned to relive. Dean glanced up and, with a monumental effort of sucking it up, straightened from his abysmal slouch in the chair. "Yeah. Angels."

"Let me guess. Cass?"

The hunter raised his eyebrows, but didn't look too surprised.

"Sam had me looking into him," Bobby explained with a shrug. Which, yeah, Dean had sort of figured. "Can't say I'd have ever gotten to angels on nothing more to go on than black hair and blue eyes."

Dean practically choked, coughing around the mouthful of beer as he hacked at his chest. "What? H-how?"

Bobby looked torn between answering and making sure the kid wasn't about to swallow his own esophagus, giving him plenty of time to realize the answer on his own. Missouri Mosley. She was the only one who could have glimpsed Cas from his head. Damn that woman. But of course, it was probably his genius little brother who'd put it together, asked the right questions, and refused to let it drop without answers.

"That kid," he muttered, ever amazed by his brother's tenacity.

"Tell me about it," Bobby chucked out in agreement. "So, this 'Cass'…He one of the good guys?"

"Uh….yeah." Dean cleared his throat, pulling his thoughts away from his brother. "Castiel, holy tax accountant of the Lord. He might have started on the wrong side of things but…yeah, he's one of the good guys."

"Tax accountant?" It was Bobby's turn to stare at him with raised eyebrows.

Dean let out a laugh, taking a swig from his beer. "He was a total nerd angel."

The older hunter didn't miss the bitterness that filled that chuckle, or the way that despite the evident pain in his boy's face, Dean was still smiling almost nostalgically at the thought of this Castiel. It was damn weird to see the boy who followed in his father's black and white footsteps get that kind of look on his face talking about something very much not human.

"'Was'?"

The smile on his face dropped pretty quickly, and Bobby almost felt bad about it. There was something about this Dean, this kid from the future, that made the older hunter wonder just how often he got to smile in his world.

"Yeah." Dean's eyes strayed down to the bottle in his hands and stayed there, though it was obvious from the pained glaze in them that he was seeing anything but Bobby Singer's kitchen. "He was hurt pretty bad when he sent me back. I don't think- I don't know if he made it."

It was the truth, too. Every time Cas popped up in his dreams, at the lake or pulling him out to save Bobby, Dean was sure. He was sure that at least some part of the angel had made it back in time with him. But there was no consistency – the guy didn't come when Dean called for him, begged for him. The hunter went to sleep praying to dream and usually got nothing. He more often showed back up when Dean or Sammy or Bobby were in danger, but even that was inconsistent. The guy just seemed to pop up randomly.

If that jackass was pulling another 'stay away to protect you/lead a normal life/it's not my place' crap move, Dean was going to have serious words when he finally caught the bastard.

"You got something making you think he did?" Dean glanced back at Bobby, distracted by his own thoughts. The confusion on his face was must have been clear enough for the old hunter to add, "You said you weren't sure. Could he have made the jump with you? Not that I know how time travel works but…did you need a co-pilot?"

Dean swallowed, dropping his eyes again. God, he didn't want to have this conversation! His first thought was Cas would have made the jump if he could have; he wouldn't have left him alone in this. But…was that even right?

They hadn't exactly been on great terms before the end, and Cas had picked up that nasty martyr complex from the Winchester boys pretty damn quickly. Stay behind, hold them off. He'd been doing that well before two human hunters tried to teach him humanity and royally screwed it up several times over.

Back in that graveyard, he had been hurt bad – how bad, Dean couldn't be sure – but he'd seen the look in his eye, known that final good luck that was really goodbye. It was entirely possible Cas just didn't have the juice to do more than send him back. His grace shredded, possibly on lockdown from Lucifer, all but a step away from mortal before it all started….

The last time he'd been that weak, sending Dean and Sam back had been ugly and left him laid up for days. To be truthful, Dean had been working pretty hard avoiding thinking about it. About what that same act would cost the angel when you added 'fatal wound' to the equation.

He cleared his throat. "I've been seeing him. In, uh…in dreams."

"Yer psychic dreams?"

Dean pinned Bobby with a look that said don't push it. The old man new damn well those dreams had been a cover the entire time, if that sarcastic comment was anything to go by. Not that Dean could blame him, given how much lying he'd been doing to his family lately.

"Sam's dreams a lie too?"

"No, he's really having visions. Azazel's causing them." Dean scrubbed at his face and ended up burying his head in his hand, propped up on the kitchen table. How the hell was he going to explain all of this? There was just too much.

"One step at a time, son. Go back to yer angel."

"He's not my angel," the elder Winchester quipped back. "Why does everyone always call him that?"

Bobby wisely declined to answer, though the smile on the kid's face the first time he brought him up and the devastation he carried all over him when talking about his death seemed pretty damn conclusive to him and, he suspected, everyone else.

Dean Winchester, closet gay for an Angel of the Lord. Well alright then.

"He used to show up in my dreams when he needed to talk. Or if he couldn't find me." Dean said it like he knew how crazy it sounded, how crazy all of this sounded. Bobby tried really hard not to react with the appropriate level of crazy that this all really, really was.

"Right." Okay, so there was at least some judgement there, despite his best attempts. When Dean leveled a look at him, he cleared his throat and moved on. "What makes you think it ain't him, then?"

"Because I'm pretty sure he's dead," the man from the future answered bitterly. "Time travel…he did it once before, when he was weak. Bobby, it almost killed him. He was spitting up blood for days."

Dean shook his head at the memory of the angel popping back into existence hours after he should have, spouting red and genuine surprise to still be alive. "Besides, it's not…it's not the Cas I know. It's like…a memory of him."

At his friend's confused look, he clarified, "He was always awkward as hell with pop culture, references, stuff like that. You know, basically humanity. But he was getting there. Even started binging Netflix."

Bobby frowned. "What's Netflix?"

Dean stared at him for only a moment. "Son of a bitch." He pointed his beer bottle at the confused hunter. "The past sucks, you know that?"

When Bobby gave him the stink eye at his unhelpfulness, he settled down and continued, "Point is, that Cas isn't the one showing up in my dreams."

"Who else could it be, then?"

Bobby wasn't trying to cause trouble, Dean knew that, but the question still rankled him. It wasn't anyone. It was his own mind, supplying his lonely, broken self with his best friend. But that….that wasn't right either. Because his own mind couldn't kick him out of his own subconscious when Dream Root had him securely under. It couldn't warn him of impending attacks, either, which Cas had done more than once now. Meg showing up early, that possessed Jehovah's Witness back when they still had Jess with them. He'd woken up shortly before each of them had made an appearance, immediately after a push from the dream angel.

Dean's instincts were good, but they weren't that good. Which left a very different version of Castiel as the only possibility. Not that that made much sense either.

"He still exists in this timeline, probably up in Heaven right now. But that Cas doesn't have a clue who I am yet." Dean met Bobby's gaze, the clear confusion in his own eyes hoping someone, anyone, could make sense of all this. "We don't meet for another two, three years. He's definitely not dream-hopping through my noggin."

"But you're seeing him."

"Yeah, but I just told you, it can't be him,"

"Unless he took that DeLorean ride with you." Bobby shrugged. "Maybe some parts got left behind."

Dean didn't answer, staring at the table top. Obviously, the thought had occurred to him enough to break down and pray, to plead for him to answer, to be alive and here, however weak or broken.

Cursed or not.

But he'd gone down that road before, lost the angel so many times and hoped so often he'd be back. He knew what false hope got him, and this time he didn't have Sam to talk him off the ledge of utter reckless stupidity he ran along anytime he lost the two important people he had left. So he was trying really hard not to hope at all.

"What's he saying in these dreams of yers?"

Thankful for the change of subject, however minor, Dean replied, "That I'm changing too much."

Bobby frowned and glanced down at the still blank legal pad sitting in front of him. "What have you changed?"

"Jess is alive." Dean's voice broke halfway through, but he cleared his throat and the two hunters did as all manly men do: they pretended it hadn't happened. Instead, Bobby met his emotional gaze with surprise and so many questions. "Brady killed her that night in Stanford, on Azazel's orders. Burned her on the ceiling, like…like mom."

"Jesus," Bobby breathed out, glancing back down at the paper. His eyes snapped back to the kid. "Sam?"

"Got back into hunting purely on revenge." Dean shook his head. "He was just as bad as dad…angry, reckless….He never saw what was coming. None of us did."

God, Bobby didn't want to know. He really, really didn't want to ask. But if the dread pooling in his stomach was any indication, it was worse for the kid sitting across from him. "And what's coming?"

"The apocalypse."

-o-o-o-

Bobby cleared his throat, chugged half the fresh beer Dean had pulled from the fridge in the silence that had followed that bombshell, then cleared his throat again. "So…the end of the world. Right. That why yer angel sent you back?"

Dean actually laughed, causing the older hunter's eyebrows to climb right into his receding hairline. "No," he answered with a jaded grin. "Not even close. We beat the apocalypse, and the angels that tried to restart it, and the mother of monsters that came afterwards, and Abbadon, and every other piece of crap life tried to throw at us."

The hunter realized his chest was tight, almost to the point of pain, and he was having trouble taking deep breaths, possibly because he hadn't actually taken one throughout the building rant and accompanying anxiety it came with. God, they were going to have to face that all again. His hand ached where it sat on his thigh in a tightly clenched fist. It took a moment, but he released the tension with a shaky breath. There was so much crap coming, so much he had to stop, and he couldn't even fix the friggin' apocalypse.

Bobby was staring at him again with wide eyes, probably having gotten about a quarter of that vitriol. This was going about as well as he figured it would.

"Alright…" he took a deep breath and let it out slowly. What would future Sam do? He was the one good with words. "Let's….let's start from the beginning."

-o-o-o-

The beginning was actually the end in this case.

"So, this darkness, God's sister…that's why yer angel sent you back?"

Dean scrubbed at his face. He'd given the old hunter a monumentally minimalistic rundown of Amara breaking free of her binds – conveniently leaving out what exactly her prison had been or just who released it and how – and finishing with him and Sam and Cas taking her on alongside God.

He left the whole Lucifer bit out, too. They so weren't ready for that.

"He's not my angel. But, yeah. Don't- Don't worry about it, it's not going to happen this time." Bobby raised a brow and Dean couldn't quite look him in the eye at the utter lack of belief there. He tried not to take it personally. Bobby was practical, and always operated with a backup plan. Dean was more of a….edge of the seat, seat of his pants, plans are for sissies kind of hunter. At least, when he didn't have a plan or a brother to make up a plan, that's how he rolled.

And right now, he didn't have crap amounting to anything close to a plan.

"It's not," he reiterated with some stress on the negative. "But if things go that way – and that's a long way off – I'll tell you everything. I swear."

The old hunter didn't look impressed, but he didn't press it. He was starting to get the feeling that if they covered everything in detail, they'd never get it all down.

"So this darkness was about to win-"

"No, she was gonna lose." Dean could still feel her pain just under his skin. Her anger and, worse, regret. She'd only wanted a family. The love of the those who were supposed to love you. Yeah, she hadn't gone about it the best way, but Dean could relate only too well. "It didn't matter – it was already too late. Sam was gone. Cas was as good as dead. He used the last of what he had to send me back, I think. I don't even know if he meant to go this far."

Because time travel wasn't easy on a drained, hurting angel. Who knew what Cas's intentions had been. To send him back further, before any of it so he could stop all of it, or to drop him exactly where he had. Cas had always known more about the connections of events and the flow of time better than any of them.

Dean had four trips under his belt and still no friggin' clue about that crap, so who was to say Cas hadn't meant to come back with him too. Sure as hell would have been easier if he had.

"And that's ten years from now?"

"Closer to eleven," he answered easily, rubbing a hand through his short hair. He blew out a breath, covered it with a swig of beer, and tried to keep going. "The next, uh…the next five years are what we have to stop, though. The rest of it…. We'll deal with it when we get there."

Again, Bobby didn't look convinced, but didn't push either. He settled back in his chair. "Right. So. The apocalypse?"

-o-o-o-

"Should we go check on them or something? They're too quiet." Dean was standing at the back door, trying to spot his father and brother. They'd heard some yelling, as expected, but then nothing had followed it. No angry Samsqatch stomps, no furious venting from John. Dean was starting to worry they'd actually murdered each other.

"Leave them be and stop puttin' this off." Bobby gave him the stink eye, calling him out on exactly what he was doing. "The apocalypse."

Dean sighed and sat back down.

-o-o-o-

"Azazel wants Sam for what?"

Dean stood up and got them another round of beers. Bobby chugged half his in a single go.

-o-o-o-

"So…uh…Lucifer."

"Yeah, Lucifer." Dean muttered, looking down at the tabletop beneath his rough fingertips. He pushed back in his chair, leaning on the back two legs as he raised his gaze to the ceiling. "It's not just him, though. Angels want the showdown too. They aren't going to do dick to stop it."

"Showdown?" Bobby was staring at him. He was getting the feeling that expression was going to be the new norm for a while.

"Michael and Lucifer. Heaven, Hell; the ultimate Deathmatch. Winner takes the planet. Or whatever's left of it."

"…Shit."

"Yeah. I haven't gotten to the best part. Angel's need vessels, like I said. For Lucifer, that's Sam."

"Right, that's why the yellow eyed- why Azazel is prepping him with demon blood." Across from him, Bobby's brow furled. "Who ends up taking Michael to the prom, then?"

Dean just stared at him until the old man got it. It wasn't a pretty reaction when he did.

-o-o-o-

"Back up, boy, you're going too fast." The old hunter grumbled as he scribbled an endless vitriol of death and pain and pure ugliness on his legal pad. They were already several pages deep, about equal to the rounds of beer they'd both had. It helped take the edge of the crazy. Not to mention the insurmountable.

Dean scrubbed at his scalp. "Back up to where, Bobby?"

"The seals. You said there are a butt-ton of them-"

"Six hundred and sixty-six."

"-but you skipped over what that first one was. It has to be popped first, like you said, right? So….we stop that one from breaking, we're scott free, ain't we?"

Dean chewed on his lip, a pretty damn foreign act for him, born out of the very rare, white-knuckled grip his brain was trying to have on his tongue right now. God, why did they have to have this conversation! He blew out a breath.

"Yeah…about that."

-o-o-o-

"You did WHAT?!"

"He was dead, Bobby! I had to save him!"

"People DIE, boy. It's what HAPPENS."

"Not Sammy. I won't let it."

The room fell silent. Bobby, red faced, stared at the obstinate man in front of him. Dean's fists were clenched around a bottle, eyes threatening the older hunter to push this.

"Balls." Bobby sat back, the wind in his sails depleting with the look in his son's eyes. "You're gonna do it again."

He shook his head when Dean couldn't meet his eye.

"I'm going to stop it," the young man confessed quietly, but with the kind of determination only a Winchester was capable of.

"You gotta let him go, son," Bobby whispered automatically and green eyes glanced briefly up to his. "If it comes to that, if we can't stop it…. Sam wouldn't want you to start the end of the world. To go to hell. Not for him."

"I know," was the only reply he got, muttered almost blankly from a boy who couldn't look him in the eye as he said it. "I know, Bobby."

-o-o-o-

Dean was able to remember a handful of the seals Hell had broken, as most of the battles for those had been fought between angels and demons. Of course, they hadn't learned until later that most of it as a show, with Heaven putting up a good act but purposefully throwing in the towel where it was needed.

Not that it mattered, he'd insisted to the older hunter as Bobby furiously scribbled down what he could from Dean's story. There were so many seals that anything they did to protect them would be futile. Hell would just go after the other seals, even if they were the harder ones to break. And a handful of humans couldn't protect all six hundred of them without Heaven's help, which they weren't going to get.

"All the more reason not to let that first one break, boy," Bobby muttered with a purposeful look in the kid's direction. Dean didn't bother answering.

They were just getting through an abridged version of the year after Dean had been pulled from Hell by Castiel, culminating in that horrid night in the church, chasing after his blood-addicted brother, when they heard Sam and John coming back towards the house. Dean's mouth snapped shut tighter than a virgin's legs at an orgy and Bobby spared him a warning look. They were not done talking about this. Not only did the boy have a hell of a story to finish, the old hunter knew he'd left some serious details out, if the guilt-ridden gaze avoiding him several times throughout the hour-long, heavily-truncated tale was anything to go by.

Bobby tucked the legal pad off to the side, hidden beside the multiple landlines labeled for various agencies. The back door opened seconds later.

"Hey," Sam greeted as he came back in, a rare smile on his face after a conversation with his father. Even John seemed somewhat at ease as he came into the kitchen behind his youngest. Sam eyed the kitchen table, littered with a dozen beer bottles. "Uh…little early, guys, don't you think?"

Dean snorted, then wrapped his hand over his mouth and stared moodily down at the table. His brother gave him a weird look – something between concern and the infamous bitchface – before looking at Bobby for a hint. The old hunter just shrugged.

"Been a long week."

Sam huffed in complete disbelief, but the issue was dropped for the time being. Unfortunately, all that left was the silence in the room quickly escalating in tension. Dean refused to look at his father, Bobby was staring up at the corner of the ceiling as if the cobwebs up there were the most interesting thing he'd seen in a couple years, and Sam was caught between confusion and loss.

He really wasn't used to being the one in these situations. Sam figured he might just owe Dean an apology for all the times he had to play mediator in the family.

"Look, Dean, I'm….I'm sorry." John cleared his throat as he addressed his oldest, avoiding looking at the kid as much as the kid was avoiding looking at him. "I…I shouldn't have demanded the gun, or shut you boys out. I just…"

John cast his eyes upward, as if praying for strength from a God he didn't believe in and would probably try to kill if he ever met. Dean would probably put his money on John Winchester, knowing Chuck as he did.

"You're my children, and this demon is a bad son of a bitch. I can't make the same moves if I'm worried about keeping you safe."

Dean's grip on the beer in his hand, empty now, tightened as he listened to the words he'd heard before. The same comment – reconciliation, really – that had happened between their small, broken family all of forty-eight hours before it got even more broken. John had said the same words not two days before he made that deal and died.

Damn it, don't let it be now. Not now. It was too soon, he should have months left.

"I don't expect to make it out of this in one piece," John was saying, shaking his head as he looked at an increasingly distressed Sam. "Your mother's death almost killed me. I can't lose you boys too."

The man from the future stood from the table quickly enough and with enough force to send it skidding a half foot back, rattling the empty bottles and knocking several of them over. Bobby caught one before it could roll of the table and shatter on the floor.

"And what about what we lose, huh? You're going to throw yourself in front of this, but it's gonna be me and Sam who bury you!"

Again, Sammy stared at his brother, knowing Dean wasn't talking in hypotheticals. The man standing in front of him had buried their father. Knowing their line of work, he'd probably burned him, actually. Sam ducked his head, unable to look into those angry eyes furiously blinking away tears. They shouldn't being having this conversation with Dean half drunk.

"What do you want me to say, son?" John shrugged his arms helplessly. "Killing this thing comes before everything. Before you, me, Sammy. Everything."

Dean's jaw creaked under the pressure of his anger.

"Dad," Sam cut in quietly, turning his pleading gaze to his father. "I don't want to watch you burn."

The sudden drop of color from John's face was testament to the effect his youngest son's words had on him.

"I wasn't old enough for mom…" Sam glanced at his brother, who was looking away now, trying to contain the anger and grief that had him seeing red. The youngest Winchester turned back to his father. "Don't make us bury, too."

Bobby watched the three Winchesters cautiously. His thoughts were right with Sam's, despite having actual confirmation from the kid across from him that John's days were numbered. But he knew the man, almost as well as his sons did, and he didn't see the hunter giving this up for anything.

"Three Winchesters are better than one," Sam insisted. "We need to do this together."

John finally dropped the tension in his shoulders, his body sagging with the weight of the last twenty two years. He was so damn tired, and just wanted this over.

"Okay," he whispered, closing his eyes. "Okay, together."

At the table, Dean let out a silent breath, the rage filling the lines of his body fading slowly, as if he didn't trust the sudden truce. He spared his father a cursory glance, and the older hunter nodded firmly at him. Dean didn't say anything, but he returned the gesture with only a slight hesitation.