-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: None for this chapter. I think even Dean mostly behaves himself. Our favorite King of the Crossroads gets some screen time (though he is less than happy about it).

-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 8

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

Dean was an idiot. He was a waste of time and space and god-damn angelic effort. He was useless, was what he was.

For the life of him, he couldn't understand why he'd been so stupid as to think it would only be one demon. As if he hadn't dealt with the bastards long enough and often enough to know that they were cruel, and rarely ever simple.

He'd let himself be lulled by the security of 2005. Two thousand and fucking five, when demon possessions weren't handed out like condoms at a college party. He should have known better. Hell was rearing for an apocalypse, and this was Azazel they were up against. Like hell he'd have sent in just one demon.

Dean resisted his dire need to hit something for the sixth time since they'd arrived at the hospital. He'd have to leave soon, if only to find a wall nurses wouldn't kick him out for punching a hole through. The hunter scrubbed a hand over his face and chanced a look down the hall.

Jess was sitting, numb and unmoving, in one of the waiting halls. Her forearm had been stitched and wrapped tightly in white, sterile gauze. Sam sat next to her, his bean stalk frame slumped. He held her hand and neither of them said a word.

Dean knew what was coming. Even in a new timeline, in a hospital he'd never been in after a fight he'd never fought first time around, he could see what was coming.

So he pushed off the wall and headed in the opposite direction.

This was going to end, Jess and her family were going to be safe, and he damn well knew what was needed to do it.

-o-o-o-

"I can't do this."

She hadn't meant to say it. Or, rather, she had meant to say it – had been meaning to say it for almost a week – but she hadn't meant to say it like that. Just blurt it out, in the middle of a silent hospital hallway, with Sam sitting next to her while they waited to find out if she still had a father.

Frank had gone into surgery the minute they'd arrived, tires screeching to a halt outside the Emergency entrance. The car they'd borrowed from those other guys was a mess of blood now. She wondered with detached concern who would clean it.

Anne was in a room of her own, sleeping off the sedation administered shortly after they arrived. She'd been hysterical, almost unable to speak. The EMTs that met them at the door said words like 'shock' and 'acute distress'. When the doctors learned it was her husband being escorted into surgery with a knife in his gut and his blood on her hands, they'd given her a sedative and decided to keep her for 24-hour observation.

They still hadn't heard anything about Frank yet.

Sam's hand tightened around hers. "I know."

She stared at the scrapes on his knuckles and the patches of gauze nurses had taped over the wounds deep enough to need cleaning. Jess tried, she really tired, to find comfort in the fingers wrapped around hers. She used to love how small her hand felt in his. How long his fingers were entwined around hers. It had been a silly thought, like a little girl daydreaming, but she'd always known the photograph of their clasped hands and a set of matching rings would be her favorite picture from their wedding day.

Sam was suddenly in front of her, crouched at eye level and holding both her hands in his. He was looking at her like she was the only light in his world; a light he'd knowingly extinguished.

"I know," he said again, and leaned forward to press his forehead to hers. Their fingers, still entangled, lay unmoving in her lap. He didn't say anything else; she didn't need him to.

They sat like that until the tears finally came and she sobbed into his chest for everything they'd lost, and what she might lose still.

-o-o-o-

Bobby left a couple hours after Dean did. He told Sam he'd be on call if they needed anything – anything at all – but this fight wasn't over yet and they'd need eyes on the books if they were going to figure out why demons were gunning for them. Sam, who had taken the conversation a few feet away from Jess to try and give her some seclusion from it all, only nodded tiredly.

The old hunter dug into his pocket and pulled out a worn, crinkled business card to hand to Sam. It was for a psychiatrist.

"She knows all about the life," Bobby mumbled with a half shrug. Sam stared at him in surprise for a moment, but he supposed there were people out there – normal people – who learned about the things that went bump in the night and decided to help others without turning into nomadic, revenge-driven hunters hell bent on a life of death and loneliness. And if there were, leave it to Bobby to know of them. "She ain't local, but least they'll have someone they can talk to."

Sam had to blink back the tears that filled his eyes. Usually, he was able to keep it together better, but this really was the week from hell and he tried not to beat himself up too terribly for it. Bobby made a grunt that probably meant 'come here, son' before he enveloped the younger Winchester in a tight hug.

"Thank you, Bobby," Sam whispered and the older hunter clapped him supportively on the back like his father never did.

Bobby hopped a plane back to Whitefish a couple hours later, collected his junker and his dog, and headed back to Sioux Falls and the stacks of books waiting for him there.

-o-o-o-

Where are you?

Sam stared at the screen of his phone, awaiting Dean's reply, as he tapped his foot against the leg of the hospital chair in a move of anxiety, tiredness, worry, and guilt that perfectly summed up how he was feeling internally. Frank had gotten out of surgery an hour ago, and the doctors had thankfully reported he would make a full, but slow, recovery. Jess was in his room now with her mom.

Meanwhile, now that one crisis was partially resolved, Sam had a million more to juggle. Truth be told, over the last five days he'd felt like someone had cut both his arms off, morbidly added them to the pile of things he was supposed to balance, and then stared expectantly.

On top of his brother acting downright weird, demons apparently wanted his girlfriend dead and his head on a stick (or something equally confounding), Jess's parents had been attacked and the family was irreparably scarred for life, the five-day road trip from exhaustive hell had culminated in the realization that Sam was likely never going back to school nor marrying the girl of his dreams, and now Dean had up and left with nothing more than a worrisome text about having a plan to 'fix everything.'

He honestly wasn't sure what was holding back the panic attack and instinct to find a hole, curl into a ball and spiral into madness. Sam had a feeling that dam, whatever it was, was about to break.

Everything hurt, from his body to his soul to his mind.

There was an ache in his heart he couldn't ease up on, knowing as he'd known for days now that this was the end of the road for him and Jess. He couldn't ask her to keep living a life on the run. He couldn't ask her to face death because demons had an unexplainable hard-on for him. And he had no clue how he was going to get her or her family out of it.

He would find a way, no matter what it took. She deserved so much better than this.

But he couldn't deal with that right now. Maybe it was his brother's influence back in his life, but he packed up all the hurt and chaos that came with that knowledge and pushed it aside. Unlike his brother, he would deal with it later, but right now it was just one of the many things he had to fix, and he couldn't work on all of them at once without falling into that spiraling hole of madness he was barely keeping at bay.

So he focused on the Dean Crisis. Well, one of the Dean Crises. Actually, the least troublesome of the multiple crises his brother was currently spawning.

Driving to CO text u when I get there

Sam frowned as his phone buzzed with the reply. Why the hell was his brother halfway across the country? Not to be selfish, but he could sort of use some damn family support right now.

Gonna fix it Sammy I swear

The younger of the Winchester boys let out a frustrated sound as he stared at his phone. Nothing in that text boded well for them. Dean had a martyr complex that could rival a damn saint, only with a fraction of the likelihood of ending up in the Catholic Hall of Fame. God only knew what trouble .he was getting himself into in his effort to bear the weight of the whole damn world alone.

Sam didn't have a clue what had been going on with his brother for the last week, but it was like that weight had increased a hundred fold. Not to mention he was acting as if he'd already failed. Not that Sam knew what it was he could have possibly done, given none of this was his fault, but he knew the signs of a guilt-torn Dean. It was like the brother he had always known, only cranked up to about a thousand and minus the protective mask of crude humor, sexual prowess, and arrogance.

It was baffling, and all Sam could come up with was that Dean had seen something.

As far as the younger Winchester could hazard, Dean's visions were a lot stronger than his own. They had a clarity to them that Sam wasn't getting. His always ended in a pounding skull and a mess of blurry images and leftover emotional stimuli. Dean walked around like he knew the damn future and it didn't cost him a thing.

Well, other than the world's biggest (and heaviest) medal for martyrdom.

Sam was stubbornly ignoring the twinge of jealousy that niggled the darkest parts of his brain anytime he thought of the differences in their new psychic abilities. That was a mini-crisis he would happily lock in a closet and never address again.

Hows Frank?

He sighed, compartmentalized once more, and texted his brother back.

Okay. Out of surgery. Why Colorado?

Sam waited impatiently for his brother to text him back. His foot resumed its tapping against the cheap metal of the chair.

Driving text u later

He had to work really, really hard not to throw the phone at the wall opposite him. Award-worthy hard. His brother was an asshole. Still, Sam could picture the damn grin he had on his face in the front seat of the Impala, glancing at the screen of his phone every couple of minutes, awaiting Sam's bitchface reply.

Despite everything, he figured some things never did change.

The younger Winchester took a deep breath, chose to find solace in that small thing, and texted back exactly what he knew his brother was expecting.

Jerk.

Bitch

The speed of his reply only confirmed that Dean had already had the damn thing typed out in expectation of sending. His brother was an asshole. But, one of the things that came with martyrdom was affection, apparently.

Sam closed his phone and decided that crisis, while confusing and probably going to bite him in the ass in the very near future, could be downgraded to orange. He had more pressing red alerts to deal with now.

-o-o-o-

They tried to talk once more, the first night after Jess's dad pulled through surgery. They sat in their borrowed car outside the Moore family home (the blood mysteriously gone from the backseat, but Jess didn't ask and suspected Bobby had something to do with it). Sam drove Anne and Jess back once visiting hours ended. Her mom quietly got out of the car and headed inside, hesitating only for a moment at the door.

Jess looked desperately like she wanted to follow, to support her poor mother who was struggling with the aftermath of trauma, but she stayed where she was. Bobby had already been back earlier in the afternoon while Sam stayed at the hospital, to try and mop up the water and clean the blood off the living room floor. Sam joined him as soon as Frank was declared stable, and helped the older hunter finish the cleanup and secure the house from future attacks. Both men were adamant with Mrs. Moore that no demons were ever getting into that house again.

The water damage was going to need some addressing, but that was hardly her primary concern. She insisted she wanted to go home rather than a hotel.

"I never wanted this to happen," Sam whispered in the silence of the car. He looked at Jess, all the pain and anguish that he'd brought her summed up in the guilt on his face.

She leaned forward, cutting him off before he could stumble through the speech he'd rehearsed a million times since the hallway. Gentle hands cupped either side of his neck and she kissed him across the face. Soft, desperate, sad lips pressed to his own and to his cheek, and his forehead, and his nose.

Jess was crying by the time she pulled away, thumbs stroking across Sam's skin. "I know, Sam. Of course, I know."

He was crying too and he buried his head into her neck.

-o-o-o-

Two days later, Frank was declared fit enough for release and Sam was waiting with Jess at the hospital to drive him back home. She was helping him out of bed and into a wheelchair with the assistance of a nurse when Dean finally showed back up.

He hadn't texted much over the last forty eight hours, obstinately refusing to answer any of Sam's questions.

"Sorry I was gone so long, man," Dean immediately said upon spotting Sam and jogging down the hallway towards Frank's room. He had a rectangular, wooden carrier box in his hands and he looked like shit.

Sam was still pissed, but seeing the dark bags under his brother's eyes, the stress lines pulling his skin tight and the couple days of growth on his chin, he was a little less pissed. He'd done the math; to drive to Colorado and end up back in Boston with the Impala meant Dean had flown to Montana first. Which meant he'd not only gotten on a plane, alone and most likely beating his terrified self up, but then spent almost forty five hours straight driving all over the country.

He looked it, too.

"We're gonna keep her safe. We'll make it right." Dean handed over the box with a firm nod and an air that went past determined and straight into desperation and guilt. Sam added it to the list of things to address when they got around to that whole 'this isn't your fault' and 'oh, by the way, what the hell is going on with you?' talk.

He lifted the lid with no small amount of curiosity at what had driven his brother across the continent. Propped within was an old style revolver. Like, Old West, Cowboys and Indians era revolver alongside five numbered, silver bullets.

Sam lowered the lid with a quick glance around the hallway, before leveling his brother with a raised brow. "A gun?"

"Not just any gun, Sammy," Dean said with a smirk that didn't reach his eyes. He tilted his head in half a nod as he corrected, "Sam."

The younger Winchester eyed his brother and tried to decide if 'he's completely lost it' was umbrella enough to encompass everything that was currently going on.

-o-o-o-

That night, Sam said goodbye to the Moores once they got Frank settled in the house. Anne had gone to town calling floor specialists and her contractor (yes, apparently he was on speed dial in her cell). The new floors were coming in next week, and the current ones had been treated temporarily to stem off further damage. All the susceptible furniture was sent out or cleaned in house. The place was half chaos, half terrifying efficiency and spoke to the frantic, desperate fear lying just underneath the surface.

When he had both of them before him, Anne in a nervous fidget as she cleaned things here and there and Frank sitting tired in a dining room chair, he apologized. There weren't words in the English language to make up for the last seventy-two hours, but he tried. He tried to tell them all of this was because of him, that he'd put them, their daughter, in terrible danger and he'd never meant to. That he loved her, and had so badly wanted to love them too.

Frank grabbed him before he got more than a sentence and a half out and pulled him into a fierce hug, despite Anne shrieking to be careful with his stitches. The older man didn't say a word, just held firm to the Winchester's back. Sam was crying again by the time he pulled away and he wiped at his face as he tried not to break down in front of this family that had faced so much because of him.

Anne placed a gentle hand on his forearm. She hadn't spoken much to him since that night, and he understood why. He could see it in her eyes. Anne Moore was not a cruel woman, but she didn't want him near her family. It hurt to see it, to know it. She tried her best to mask it, intrinsically not wanting to blame her own fear and pain on the young man before her, but she couldn't hide it all. Sam didn't hold it against her.

He'd put her family in danger and would continue to do so if he stayed.

So he told them both that he and his brother had a plan, and that if all went well it was the last they'd see of him. Jess squeezed his hand, her face a brittle mask. Anne started crying silently, but nodded at his words. Frank held out his hand, the kind of serious glint in his eye that meant there weren't words that could be spoken.

Sam walked out of the Moore house with the weight of the world buried in a black hole in his chest that hurt worse than any wound he'd ever gotten hunting. He had really wanted to be a part of their family. More than he'd ever wanted anything.

Dean was waiting for him in the Impala.

-o-o-o-

They were, once more, headed to a crossroads. Jess insisted once more that she come with (Sam hadn't argued very hard: she needed to see this through as much as any of them) and directed them to a slightly less populated area to the north that had a couple dirt roads and fields that might culminate in a crossroad.

Sam went for the spray can in the trunk, but Dean shook his head.

"No trap this time." Knowing that would surely start an argument, he cut it off at the head. "We already ganked one of his demons. He isn't gonna be stupid enough to show up in the center of the crossroads."

"Who?"

But Dean didn't answer, instead getting out the necessary items for summoning a deal demon. He finished off the crossroads box with his ID and a small scrap of paper with something written on it that Sam didn't catch before closing the lid tight and heading to the center of the roads.

Jess waited by the car once more as the boys buried their second cigar box that week.

The wait was quiet and tense, but lacked the same suspense present during their last summoning. Jess, who rightly should have still been freaking out even seven days later, was calm and quiet. Numb.

Dean was a solid rock with the reassuring weight of the colt in his hand. Sam was less sure, but held a stiff, defensive stance of his own. He was ready to take on whatever came at them, fidgeting nervously at the lack of trap.

"You've got some set of balls on you, Winchester. I'll give you that."

The three humans spun at the new voice, an English drawl that was simultaneously lazy and dangerous. To the right of the Impala stood a short, portly man in an expensive suit and crimson tie. His hands were tucked in his pants pockets and he had an incredibly bored expression on his face that masked the indignation and surprise beneath.

Jess immediately moved away from the demon, though he hadn't appeared near enough to her to be a threat. At least, not a physical one. Still, she moved quickly behind the two hunters, much to Sam's relief.

"Crowley," Dean greeted, and Sam looked at him like he really had lost it. "We want to talk with the yellow eyed demon."

"Oh, do you now?" The Brit's eyebrows rose in amusement. He looked like he couldn't decide if he wanted to humor the hunter or snap his neck. "Well summon him then, you bloody gnats."

"Yeah, we summoned you."

"I noticed." The demon's voice was dry and his left eye twitched as he looked to the side. He shoved his hands in his suit pockets and Sam got the distinct impression he was trying not to clench his fists. Instead, he let out a dramatic sigh. "Very well. What are you offering in exchange?"

"Oh, you're doing this one for free." Dean lifted his gun, his aim true. "We'll wait."

Crowley's bored expression turned ugly as he took in the gun and immediately recognized it for the Colt. Bollocks. "Any particular reason I shouldn't kill you and the happy couple? Take the shiny toy gun for myself?"

Dean shrugged a shoulder. "You can try, but I'm a quick shot. And I've heard demons have this nasty habit of saving their own skin."

The king of the crossroads regarded the hunter with true, though carefully hidden, bafflement. He'd heard from his own girl that Dean was up on the take in ways they'd never predicted. Azazel had said the same of his brat, but it wasn't like Crowley really believed them. The older Winchester was a mook. An angelic condom mook maybe, but still a mook.

Besides, demons lied. They lied most often when it was their hide on the rack.

But this, this was irreparable proof staring him down the barrel of a limited edition, supernatural-deluxe, Texas Patterson 1836. This was new.

And where the hell had they gotten that bloody gun?

"Hm," he hummed as he exuded nonchalance and a proper air of kingliness. Rolling on the balls of his feet, he considered the hunter's proposition as one would select a fine steak from a butcher. Took his time in doing so, too, just to see Dean's itchy-trigger finger.

The shaking leaf of a thing behind the two men caught his eye and the corner of his mouth quirked upward. "Are you sure you want ole' Yellow Eyes here? Seems to me you haven't thought this through, boys."

Sam's glare turned hostile as he stepped fully in front of Jess. The hammer of the Colt cocked back under his brother's thumb.

"Alright, alright," Crowely conceded, raising his hands placating. "No need to get violent, gentlemen. I'll fetch your Mommy Killer."

If they hadn't had a history – wouldn't have a history – Dean might have shot him.

He lowered the gun as the demon disappeared in the blink of an eye. Turning to Jess, Sam placed both of his hands on her shoulders to reassure himself of her presence as much as comfort her. She was biting her lip and refusing to look at where the demon had been, but otherwise stood strong within her lover's arms. Dean turned away to give them a moment.

Crowley popped back into existence in the center of the crossroads without so much as a confetti bomb. By his side was Azazel, wrapped in the body that Dean would kill him in.

But not tonight.

"You know what this is?" He held up the revolver and pale, yellow eyes trained on it with a look of distaste. Dean took it as the affirmation it was, then tossed the gun to Sam.

Jess screamed as he pressed the muzzle flush to his temple.

"You want me?" Sam asked, eyes never leaving the demon who had killed his mother, who had planned to kill his girlfriend. The creature that had ruined his life twice over. "Then Jess is out. Her parents, her extended family, anyone who so much as knows her name. They're untouchable."

The demon tilted his head, eyes glinting as he evaluated the situation before him with as much curiosity as caution.

Dean held Jess back with an arm, keeping his eyes trained on the two demons. There were so many ways this could go south, and he was going against every protective instinct carved into him over the years by handing his brother that gun.

Because damn if they didn't both want to put a bullet between Azazel's eyes. Dean knew everything he had done, everything he would do. Sam knew enough to want him just as dead. They couldn't, no matter how much they wanted to. No matter how justified they'd be. Tonight had to be about the Moore family; they had to procure their safety. If the brothers killed the bastard now, they'd have an army of demons out for revenge in the worst ways possible. Jess's family wouldn't make it through the week.

For his part, Crowley looked astounded as he glanced between the two parties like a tennis match. It was a damn beautiful sight to be sure and one Dean might have enjoyed in a less dire moment. He'd sure treasure it the next time he had to deal with the smarmy bastard.

Azazel was far more composed, and exuded danger. If he was relying on appearance alone, Dean might be worried he wouldn't take the bait. Those pale yellow irises were daring Sam to pull the trigger, just to see if he would. It was only because the older Winchester knew the end goal that they could even pull this off. Hell needed Sammy alive, but Dean knew he wouldn't hesitate to pull that trigger if it meant saving Jess.

And Azazel knew it to.

Sam's hand was steady even has his legs shook, standing for the first time in front of the thing that he and his brother and his dad had spent the last twenty-two years hunting down. Sam's whole life, summed up in a middle-aged man with yellow eyes standing in the center of a crossroads. "There's no bringing me back from this. So she's out and I keep breathing."

The demon watched for another moment, testing the younger hunter's conviction, before settling back on his heels in a suddenly relaxed stance that gave away how tense he'd actually been. A smile broke across his face, splitting his skin into something foul and wicked. "Alright. She's out."

Sam's finger tightened on the trigger and the demon sighed dramatically.

"And her family too. Don't get your panties in a twist, tiger," he condescended, raising his hands in a mockery of defeat. They quickly shifted to far more dominant position, pointing at the boy with a grand sweep. "But you've got to keep hunting."

Sam's brow furled. The last thing he expected a demon to want was another hunter in the world. Azazel smiled brightly, teeth glinting in the moonlight.

"It's what you were made for, Sammy-boy. Bred for, really."

Beside him, he missed Dean's eyes narrowing. But the demons didn't.

"Fine." Sam lowered the gun, but did not release the hammer. "I want your word."

Azazel raised a brow mockingly at the boy, but Sam Winchester wasn't looking at him. He was looking at Crowley.

The King of the Crossroads was well and truly stumped by the scene unfolding before him. The two dimwitted brothers apparently not only had a significant clue to Samuel's role in future events, but also knew Crowley by name, and had a hell of a pair of balls between them to ask for the demon who'd orchestrated all of this to begin with.

And yes, Crowley was fucking pissed he was being used as a god damn messenger, thank you for asking. He was the King of the Crossroads, god damn it. Some respect would be appreciated.

Now, now, he was staring at Sam Winchester like the moose of a human being (and sweet Jesus what were they feeding that kid?!) had gone and grown two heads.

No. No, that wasn't it. Crowley had seen a human with two heads before. This was far more ludicrous than a genetic freak of nature.

This was bloody insanity.

"What?" he asked, perfectly calm and rather polite given the situation, and not in a shrieking sort of manner at all. Not at all. That would not be very kingly. He raised his hands, quite content to be the messenger. "I've got nothing to do with this."

"You're a crossroads demon, aren't you?"

Crowley bristled at the common label slung about like a meager insult. As if he was just some two-bit salesman. He was the bloody king and he'd earned that title!

Sam's trigger-happy hand twitched on the Colt and Crowley simmered down with a growl and a damn unhappy grimace. The moose didn't let up but he did continue, "You make deals, so officiate this one. I want your word as King of the Crossroads. Jess if off limits, or both our lives are forfeit."

Crowley was speaking before the younger of the two insane hunters even finished speaking. "No bloody way-"

"Deal."

All parties turned to Azazel, who smiled sweetly at them.

"No deal!" Crowley growled back, fisting his hands at his sides as he regarded the demon, now both offended and appalled. The fucking bugger had a lot of nerve. "It's not your bloody life they're asking for. You can bargain with your own damned soul."

"Too late." Sam finally lowered the blasted gun to his side with a grim smile that looked more like death than an expression of victory.

Crowley sneered at all of them, the bastards. With a mumbled 'bollocks' and a hastily written contract that he all but chucked at Sam Winchester's soul, he whisked himself away back to his fortress and his 30 year old Craig. He was owed a good long sulk and perhaps a temper tantrum.

Sam's grip on the Colt tightened when the Yellow Eyed Demon did not leave as well.

He was watching Sam with a gleam in his eye that might have once been pride on the face he wore, but now just looked like malicious delight.

"You know," he began, and though he never moved from the center of the crossroads, it damn well felt like he was circling, "things are turning out far more interesting than we predicted."

His pale irises shifted to look at Dean and Jess. "I wonder why that is."

Then he was gone.

Sam all but collapsed, bending over to brace his hands on his knees as he let out a shaky breath and took in a gulp of air that nearly had him choking. Dean couldn't have stopped Jess from going to his side if he had tried, and he didn't. Sam straightened to scoop her into his arms and press his face into her hair and breathe in the familiar, comforting scent. She was chastising him as much as she was kissing him, and he tried to reassure her with a shaky voice that he was in no way suicidal.

Over her shoulder, he handed his brother back the Colt. The relief of its weight gone from his hand made his stomach clench.

He would have done it. Dean had been sure he wouldn't have to, but that wasn't the point. Despite the comforting words he mumbled into Jess's ear, he would have done it. He was ready to do it. His legs felt like jelly beneath him and he cursed his own fear. He was a hunter, damn it. Death was part of the gig.

Within his arms, Jess turned her head to glare at Dean, who was tucking the Colt into the back of his jeans. "This had better work."

The older hunter stared at her in surprise for a moment, unsure if the venom was coming from the fact that he'd put Sammy in danger with his plan or that he'd put them all in danger by dragging his brother back into hunting in the first place. Or altering the timeline and dragging her family into it instead. There were just so many options to choose from.

"Trust me," he tried to instill as much confidence and assuredness as he could into his words, to promise that her family would be safe from now on. That she would be safe. "Crowley will do whatever it takes to save his own skin."

-o-o-o-

Sam didn't talk on the drive back from dropping Jess off at the Moore home. He didn't say a word as they pulled into the dingy one-star motel parking lot, tiredly grabbed their bags and headed inside. He sat on the edge of the thin mattress on its squeaky frame, his back to the room and the world.

Dean watched from the doorway as his little brother tried to hold it together, staring at the wall. But his shoulders began to shake and his head ended up in his hands.

Dean Winchester had never been good with feelings. At damn near forty years old, he still had no idea what to do with a distraught, hurting Sam.

He could see the same shades of sadness in his brother that had been there once before. This time around, instead of the anger and self-loathing and guilt, there was only sadness. It wasn't great – could hardly even be called an improvement because he had still lost Jess – but Dean knew that it was better.

She would live a full and happy life, even if Sam couldn't be in it. And that difference mattered.

His little brother was still walking the path of a hunter, so in a lot of ways nothing had changed. The apocalypse was still set for a five year swing. But Dean was determined not to let that make this small triumph mean less. Because his brother wasn't suffering the same loss and he wasn't sinking into the cold-edged revenge that would define the rest of his life.

A life of pain and hurting that ended in a graveyard and puddle of blood. If things were going to change, Dean Winchester was going to have to do some changing of his own.

So he walked over to the side of Sam's bed and sat down beside him. He might not have any idea what to say, but for once in his life he was going to figure it out.

"I wanted to marry her."

He looked at his brother's hands, and white-knuckled around a ring box, and his heart broke a little on his brother's behalf. He ached for the kid. Dean raised his hand to settle on his brother's shoulder, hesitating and not having a clue what he was doing, but clasping Sam's shoulder all the same. He could feel the tremors just beneath the skin, and gave a reassuring squeeze, hoping he wasn't making it worse.

"It probably doesn't help – Hell, I know it doesn't help. But I think she wanted that too."

His younger brother laughed, the mirthless sound breaking down into a sob that he tried to fight, but lost. He was crying, and damn it all, Dean didn't have a way to fix this. He had always been better at messing these sorts of things up than fixing them.

But he stayed. Sam cried and Dean stayed, and if Time was an oracle you could talk to, she'd have said the future was a little less dark.