-Chapter Warnings: Dean's still swearing, Sam's making extra bitchfaces, and Brody is a douchebag with perfect hair.

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The Road So Far (this Time Around)

Season 1: Chapter 2

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It was well after the sun came up that Sam stumbled out of his bedroom to find his brother chilling on the sofa with his laptop open, typing away. He was wearing a fresh shirt and had made himself right at home, apparently. Which was…odd, Sam thought. Pretty domestic for his very nomadic older brother.

"Hope you don't mind," Dean answered his questioning glance at the laptop offhandedly and hardly apologetic.

"Dude, you better not be watching porn."

His older brother smirked and winked at him. Sam made a disgusted noise but was grinning as he ventured into the kitchen for some orange juice. He'd forgotten what being around his brother was like. He didn't realize how much he had missed him these last four years.

"Hey, uh, so," Dean cleared his throat from the living room, which meant he had done something Sam wasn't gonna like. "This guy kept trying to message you like an hour ago."

Sam ducked his head back into the living room. "Guy?"

If Dean hadn't been so focused on lying convincingly, he might have cracked a pretty good joke on that one. Sam was so easy; ten years hadn't changed that. As it was, he just nodded and pointed to the computer in his lap. "Brad or something?"

"Brady?"

"Yeah!" Dean said with maybe a little too much enthusiasm. Because trying to find that asshole through the school website had been a bitch without knowing his actual name. "Uh, I mean yeah. So I answered."

Sam automatically groaned.

"Hey, in my defense," he raised his hands, "you're the one who left your laptop out."

"It wasn't out, it was in my bag," the giant answered without missing a beat, pointing to the go-bag still sitting on the chair and looking more than a bit rummaged through. "And it's password protected, Dean."

The older hunger gave his most winning smile. He may not know computers, but he knew Sammy.

"Ugh, whatever." His moose of a brother rolled his eyes and retreated back into the kitchen. "How badly did you traumatize him?"

Dean balked. "I did not traumatize him. Guy called me out pretty quickly, actually."

Which had all been part of Dean's plan. Well, the part about messaging the guy hadn't exactly been one of the steps, but the rest totally was. He'd still been trying to figure out the asshat's name when a chat popped up in the bottom right corner of the screen from one, SexyStanfordDr1084.

Ass. Hole.

Not one to pass up the opportunity (and feeling pretty certain it was Brady on the other line, considering his first line was 'You back in town, bro?' Bro? Really? It was 2005, for fuck's sake), Dean had set about making a poor imitation of Sam. Brady had called him on it pretty quickly, and he'd revealed himself as Sammy's older brother, in town visiting and concerned for his widdle brother's virtue while all alone in the big scary world of frats and co-eds.

The demonic scumbag had eaten it up, no doubt chomping at the bit (and foaming at the mouth) for an opportunity to get close to Dean Winchester. Even pre-seals, he was pretty sure the troops down south were talking about the war to come. Especially the guy tasked as his brother's keeper. Azazel would have given him the basics, at least.

"Of course he did," Sam was saying in response to Brady's so called 'intelligence' at noticing it wasn't the high IQ future-lawyer Winchester he'd been talking to. Yeah. Real genius, that one. "He's pre-med, Dean. He's not an idiot."

It took all of the older Winchester's willpower not to respond with something that would most likely get him into trouble.

"Bitch." Well, maybe just a little bit of trouble.

"Jerk."

Sam walked back in with a glass of orange juice and a cup of coffee. He set the latter on the low table in front of Dean, next to the abandoned laptop. "So?"

"So I'm meeting him for a beer."

Sam pulled Bitchface #4 ("Stay out of my stuff, Dean!")

"Dude."

"What?" Dean had the decency to at least act insulted. "I can't get to know your friends?"

Sam leveled a serious look at him, eyes narrowed and suspicion fully bared. "Is that what you're doing?"

Dean scoffed. "I'm just checking up on my baby brother. Making sure you haven't gotten yourself into trouble in the scary world of higher education."

Sam actually had gotten into trouble, sarcasm aside. Though with the plot those bastards downstairs were cooking up, it wasn't exactly Sammy's fault he hadn't caught on. Even the most seasoned hunter wouldn't have seen it coming. Dean certainly hadn't.

His brother, however, didn't know any of that and currently looked seconds away from an explosion. "Dean, none of my friends are-" he cast a glance to the bedroom door, where faint sounds of running water could heard, "-monsters! They're just normal college kids living normal lives!"

The words made Dean's stomach twist. If only.

"Then there's nothing to bitch about," he said instead, putting on his best 'I'm older and that's that' face. "Just two dudes grabbing a beer."

"Fine," his brother snapped. "But Dean, I swear if you-"

"Relax, Samantha. It's just a beer and some friendly, normal conversation."

Sam still looked ready to punch him.

"So." He stood up with a grin. "We grabbing breakfast, or what?"

-0-0-0

Sam hadn't been wrong. It was hard not to like Jess. She was beautiful, glowing with love for his brother, witty and smart, and had a biting tongue that gave back as good as she got. Dean liked her already, and they'd only just had breakfast.

Dean hadn't been wrong either. She was way out of Sam's league. It was ridiculously obvious how head over heels the kid was for her. Dean wasn't sure if he was closer to tearing up or throwing up.

Of course, since Winchesters did neither, he was perfectly fine.

Brunch that morning was possibly the most surreal experience of Dean's life, which was saying something. Seeing his brother happy, in love, and perfectly normal only sharpened his conviction to change what was coming. His brother deserved this. And it didn't take much to see Jess deserved life.

By the end of the meal, Dean had every confidence that he could do this, for them. He was going to change the future.

-0-0-0-

Sam tried to invite himself to the Dean-Meets-Brady shindig no less than three times. It got to the point where Dean finally told him to go get his own friend. Sam made the ultimate bitchface at that and Jess dragged him off to go lick his wounds in the safety of their very demon-proofed apartment.

When Brady showed up at the off-campus bar, Dean was already waiting for him against the trunk of the Impala. He hadn't (wouldn't? How did tenses even work when you were from the future?) changed much in ten years, and Dean instantly recognized him with his douchebag hair and rows of perfect punch-worthy teeth.

The guy gave an award-winning smile (seriously, how much would it throw off his plan if he just socked the asshole in the mouth right now?) and stuck his hand out as he approached. Dean shook it with a grin of his own.

It was only too easy in the end. He'd forgotten how simple hunting had been when the demons still underestimated the Winchester boys. Okay, they'd never really stopped underestimating them, but this was a whole other level of naïve.

He pulled out two beers from a cooler in the back seat, popped their tops, and handed one to Brady with a line about always having a few on hand for the road.

"Thought you wouldn't mind a freebie."

The demon grinned like an idiot (which he was) and clinked the neck of his bottle to Dean's. Then it was as simple as sitting back and waiting for the smoke and sizzling flesh, burned by a mouthful of holy watered-down beer. Getting him into the devil-trap-lined trunk was as easy as pop, shove, slam.

Now he was driving out of Palo Alto and towards the hills that lined the west side of the peninsula. There were a ton of state parks and preservations that way that would guarantee an empty stretch of woods where he could interrogate and exorcise the son-of-a-bitch without risk. He'd been able to scope it all out using Sammy's laptop that morning. He'd settled on the ridgeline when he realized he wouldn't have time to sneak out and prep a devil's trap even if he did find a good abandoned building for it. Sam had been pretty insistent they spend the day touring Stanford and the surrounding area.

He had ignored the twist in his gut all day as Sam proudly showed off his perfectly normal life while Dean walked beside him, planning how to kill his brother's best friend.

Popping the trunk revealed a red-faced, spitting Brady. The demon surged forward, arms outstretched for Dean's throat. The devils trap caught him before he ever got close and threw him back into the trunk.

"Sit tight, princess. It'll be your turn in just a second."

He was reaching into the trunk for the spray paint (carefully avoiding the still violent demon) when a set of headlights rounded the dirt road and lit up the wooded sanctuary he'd chosen for the exorcism.

Swearing, he slammed the trunk (feeling just a little satisfied when he heard the metal connect with the demon's skull on its way down) and turned, hiding the shotgun and holy water behind him in a single motion. The car coming down the path careened to a stop a good ten feet away from the Impala. Dean swore even louder when the door swung open and Sam of all people climbed out, gun of his own aimed at Dean.

"Sammy, what the hell-"

"Let him go." The gun was perfectly level and Dean made a face at it.

There was suddenly banging on the trunk, frantic and desperate. "Sam? Sam, help! Please, he's crazy!"

"Shut it!" Dean barked over his shoulder. His shotgun remained on the trunk behind him, not that he'd ever pull it on his brother.

Sam tightened his hand around the grip of his handgun, heedless of being the only one aiming his weapon in this showdown. "Let him out," he repeated and Dean could tell he was seriously considering shooting him.

Oh, come on! This guy could not be that good a friend.

"I don't know what you are," Sam continued, raising his arms and setting his face in determination and anger, "but let Brady go."

"Sammy," Dean groaned, throwing his arms out to the sides, "You don't tell the monster you don't know what it is! You might has well wave around a neon sign screaming 'I don't know how to kill you!'"

Sam frowned at him, but the gun didn't waiver. His determination did, though: Dean could see it in his eyes. Sam wasn't a hundred percent sure Dean wasn't Dean. Even with his last comment, the kid was still sharp enough to know his brother wasn't the same guy he had been two days ago.

"Open the trunk. Now."

Dean leveled his brother with a sober, if slightly annoyed look. Reaching behind him, he turned the key and the trunk opened with a click. Brady pushed it the rest of the way open, sitting up with crocodile tears and a fantastic look of panic.

Fucking demons.

"S-Sam, please. Please, your brother's crazy!"

There was blood pouring down the side of his face, courtesy of the underside of the trunk shutting on his stupidly perfect hair. Unfortunately, it added to the damsel in distress act he had going on. His hands were raised in a half placating, half begging pose, pleading to the younger brother to save him as he blinked blood out of his wide, traumatized eyes.

"Please," Dean scoffed, rolling his eyes at the drama act. "Sammy, he's a demon."

Sam jerked in surprise. His eyes narrowed, looking quickly between his (possibly fake) brother and his (now possibly possessed) best friend. The gun stayed trained on Dean, but the intent to actually use it seemed further off now.

"A- a what?" the faker stuttered in shock, looking between the two hunters. "I'm not a- are you insane?"

Dean's eyes never left his brother as he dumped the canister of holy water over his shoulder.

Sam went a few dozen shades whiter as Brady screamed and hissed and smoked, clawing at his steaming face. He bared his teeth at Dean, hissing like a wild animal. Sam's gun arm waivered, lowering almost to his waist before retraining it on the writhing demon.

"Dean?" he asked, voice weak and unsettled, begging for answers to his life being turned completely upside down. Dean stepped away from the trunk, coming closer to his brother. He kept the shotgun down and broadcasted his movements clearly, in case Sam still had any doubt as to what he was.

"Sorry, man. I didn't want you to know."

Sam screwed up his face in a tight, squinted look of hurt that Dean knew well. It was the expression Sammy wore each and every time he felt betrayed by his brother. "What?"

The words were breathless, and Dean battled with his instinct to look away.

"Is this why you came here?" Sam asked. His gun remained trained on Brady, but the anger was directed at his brother now. "The hunt in Jericho – Dad missing? Was that all just some excuse to get me out of Stanford so you could kill my possessed best friend without having to tell me? What the hell, Dean!"

"That's not-" Dean cut off, shaking his head angrily. "Dad is missing, but that has nothing to do with this! I didn't know in advance, okay? I just found out!"

Sam's anger drained away from him as he stared at his brother. He lowered the gun, knowing it wouldn't work for a demonic possession anyway. "How? How did you-"

Dean shrugged. "I gave him a beer laced with holy water. It's, uh, a trick I learned from dad. Wasn't expecting anything to come of it – I was just running all the normal tests."

Brady suddenly laughed, pulling their attention back to him. He was sitting, shoulders slumped, face red and splotchy from the water, ruse abandoned. "Bullshit. You were ready for me. I don't know how you knew, but you knew."

Dean narrowed his eyes at the demon. "Shut it."

Sam looked to his brother, full blown puppy dog eyes begging him to make the world make sense again. At least, that's what the big brother in Dean saw whenever Sammy stared at him like that.

"Later, Sammy."

Silence reigned in the clearing, as if the stupid crickets wanted to hear what happened next. Dean's finger twitched against the shotgun's trigger.

"It's Sam," the younger Winchester corrected calmly and Dean could see the change take over his brother. The way he tensed his forehead, smoothing away any wrinkles on his brow, screaming 'I know when you're lying to me.' The setof his shoulders that vowed, 'We're not done talking about this.' The tick in his jaw when he was pissed as hell, but firmly resolved.

His little brother had just fallen into hunter mode, something that hadn't happened the first time around until after Jess's death.

Somehow, it felt like failure to Dean: a sucker punch to the gut. He didn't know why – Jess was still alive, and he was still hell bent on keeping it that way. But it felt like he was already behind the curve, too far to catch up. Like Sammy had already set his mind to hunting, just like the first time after finding his girlfriend roasted on the ceiling.

Which was ridiculous, because none of it had happened yet – they were stopping it from happening – and all Sam had done was pull a face. Nothing had changed. They'd still kill Brady, Jess would be safe and Sam could go back to apple pie.

So Dean nodded his head, conceded to 'Sam' over 'Sammy' and in doing so apparently agreed that they'd talk about it later. A promise he would deal with equally later.

Sam turned back to Brady, all business now. Whatever he'd needed to do to tuck away the shock and betrayal, he'd done it. "How long?"

"Oh, I'm sorry, are you taking to me now?" Brady asked, revealing a mouth full of bloody teeth as he smiled. "I hadn't realized the Lifetime moment had ended."

Sam didn't even blink. Brady sighed dramatically, "Come on, Sammy-boy. You already know the answer. Think really hard."

The younger hunter's jaw clenched, the veins popping with the harsh treatment. "Sophomore year, Thanksgiving break."

Brady broke out in the widest smile yet. "Ah, the booze, bitches, and drugs. Those were the good days. Remember how much time you spent trying to get me back on the right track?" The demon laughed, a gurgling sound that must have hurt like hell with his ruined throat. "You were such a good friend, Sam."

"Why?" he ground out, fist clenching, gun hand shaking. "That was two years ago! What the hell is your end game?"

Before Brady could answer, Sam stiffened and lost any color he'd regained. His breath when he finally released it shook. "Jess."

"Ding ding ding!"

Sam glanced at Dean briefly, his voice devastatingly quite when he talked. "He introduced me to Jess. A-after….After sophomore year." His hands were shaking at his sides. "Is….Is she? She's not. She can't be."

Brady's grin grew feral as he finished Sam's train of thought. "Of course she is-"

"She's not."

Both men looked at Dean, who'd answered so matter-of-factly you'd think they'd been talking about stock market stats. He glared at the demon briefly before nodding to his brother reassuringly. "I checked. She's human."

Which was a total lie, and now Dean was sort of wondering if he should check, but was pretty sure he didn't need to. First of all, she'd be stuck on a devil-trapped rug back in the apartment right now (which, while amusing to picture, would likely not have gone unnoticed by the two hunters currently staying with her). Second, there was no way Future-Brady would have let that opportunity for back-stabbing bragging pass. He would have rubbed it in Sam's face that he'd fallen for a demon (again). That she'd been one the whole time. That she'd never actually loved him.

No, he was just feeding off what Sam had given him.

The demon was watching Dean with narrowed, curious eyes. He met the stare head on. Sam was still reeling with relief that his girlfriend wasn't a lying denizen of Hell.

"Why would you introduce me to her?" he asked quietly at first, voice confused, before he rounded angrily on the demon. Sam wasn't stupid. On the contrary, Dean always thought he was a minor genius, especially when it came to Sherlocking the truth out of situations. He'd make a hell of a lawyer. "Why do any of this? What the hell are you playing at?"

Brady laughed, looking between the brothers. "So you don't know? You're out favorite, Sammy-boy. We've got big plans for you."

"Not anymore, you don't." Dean emptied the rest of the canteen over Brady's head and slammed the trunk shut amid the sound of sizzling skin and screaming. A sickening crack filled the air and the trunk bounced back open after failing to click shut. Brady was howling as he pulled four crooked, limp fingers against his chest.

"Dean!" Sam barked, taking a step towards them. "He's still in there! It's still Brady's body."

Oh. Right. Oops?

The hunter grimaced, shutting the trunk a tad more gently this time. In his defense, Future-Brady had been long dead by the time they ganked the son of a bitch (and even if he hadn't been, killing the man after a decade of possession was a freaking mercy). Besides, he hadn't meant to close the trunk on his fingers. But he wasn't going to lose any sleep over it, either.

Dean bent down, scooping up the can of spray paint he'd dropped at the start of all this. As he straightened, Sam blocked him with his arm outstretched to the side. The older hunter quirked an eyebrow in question.

His younger brother held out a sliver knife that looked way too familiar. Dean reached for his hip where he kept his blade, only to find it missing. Sammy was still holding it out to him, a challenging look in his eye. Dean glanced down at the kid's gun, thankfully pointed at the ground, but with a firm finger resting on the trigger.

"Shouldn't have called you rusty," he quipped with a grin as he grabbed the knife. He rolled up one sleeve and pressed the blade to his arm, drawing a faint red line that swelled with blood. The drops of water on his shirt and skin, collateral from Brady's squirming, sealed the deal on him not being a demon. That and the silver were probably enough reassurance for his brother.

Sam relaxed fractionally, grip loosening on the gun. "Dean, what is going on? And no more lies. He said you knew what he was – that you were ready for him. How? And what did he mean, they've got plans for me?"

Dean pressed the can of spray paint into his brother's chest to avoid answering any of those questions that he really didn't have answers to. Damn it, this was supposed to be simple. Kill Brady, save Jess, keep Sam out of it.

Why the hell did Sam have to follow him?

Because life's a bitch, that's why.

Of course it wouldn't just be easy. Why had he thought it would be? He was a Winchester. They didn't get easy.

"Look, we'll get answers, okay? But we still need to exorcise the son of a bitch, and we're not doing it in the friggin' Impala. So go paint a devils trap and let's get this done."

Sam looked ready to argue, but Dean leveled a serious stare. "Go. I'll explain later, alright?"

"Dean-" his brother's voice was a warning. He wouldn't take being put off again.

"I will, okay? Go!"

Sam gave a grim nod, but still didn't move. Dean watched him expectantly, finally raising his hands in a clear 'What now?' gesture. His brother's brow furled in that way that said he didn't understand something, but didn't want to admit it. Which was kind of fair in this situation, considering there was a metric shit ton he didn't know and Dean was kind of turning his life on end.

Finally, Sam mumbled, "What's a devils trap?"

Son of a bitch. Seriously. How the hell had they lived long enough to make it to the end of the world?

Dean swiped the spray paint out of his brother's hand. He pointed at the ground with his free hand. "Stay."

He moved a good ten feet from the car to where the pine needles and loose dirt gave way to harder packed ground. Crouching, he began the large circle and five point star. Sam stayed by the trunk as instructed (and not pouting at all about it), but craned his neck to try and catch the lines his brother was painting over the ground.

By the time he finished, Sam was standing next to the outer edge, memorizing the ancient symbols with the same fire in his eyes he got when handed a new puzzle.

"Dude." Dean threw his hands out as he straightened and caught sight of his brother. He gestured emphatically at the abandoned car.

Sam just shrugged and Dean dropped his arms, glaring. His brother's eyes were already back on the trap. "Does this really work?"

"What do you think's keeping him in the trunk?"

The younger hunter's eyes doubled in size. "You spray painted the Impala?"

Dean pulled a bitchface of his own. Of course Sam would be incredulous this time. Little shit had been the one to blemish Baby's gorgeous finish first time around without so much as blinking. Nobody put Baby in a devil-trapped corner but Dean. "It's in the trunk, first of all. And second, it's an addition. It makes her even more badass."

Sam looked skeptical, shaking his head as they made their way back towards the car. "If it's painted on the trunk, how are we going to get him to that one?" he asked, nodding back the way they came. There was at least a ten foot difference, and the placement of trees limited their ability to back the Impala up to it. He may not be very familiar with demonic possession, but he was fairly sure the thing in Brady wouldn't need half that distance to overpower them.

"Just wait." Dean grinned. One advantage to being from the future was he knew all the cool tricks. And this time he didn't have to own up to learning most of them from fucking Crowley.