-Chapter Warnings: The boys are summoning demons, Bobby is being awesome, and Lucifer is having tea.

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The Road So Far (this Time Around)

Season 1: Chapter 4

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Sam was left speechless as Dean walked past him to the center of the intersection. His brother set down the cigar box and began painting the same large, five-pointed star and symbols as he had only hours ago in the woods outside Palo Alto.

"We're- We're going to what?" Sam followed, grabbing him by the arm and hauling him up when he didn't answer. "What the hell, Dean?"

"You know another way to prove it to her, Sammy?" He gestured to the car, where Jess was slowly, warily climbing out. "A crossroads demon is the easiest to summon."

And possibly the stupidest, but you couldn't win 'em all, right?

Jess came to the edge of the nearest star point, staring down at it worriedly. Absently, she crossed her arms, rubbing her bare skin and trying to ignore the way her hands shook. If anyone asked, she would have said it was because of the cold.

Sam went through several different responses, throwing them all out when he couldn't seem to form the words correctly. Finally, he threw his arms out to his sides. "Are you insane?"

His brother didn't bother answering him. He just kept painting. Sam ran his free hand through his hair, tugging at the roots fiercely. Here they were, out in the middle of nowhere, about to summon a demon to show his girlfriend – the woman he wanted to marry – that monsters were real. How had this gone downhill so fast?

"How do you even know how to summon one, man?"

Dean finally stopped what he was doing and straightened up with a look that said he was approaching his own limit of crap he could handle in one day. "Come off it, Sammy- Sam. You were gone for four years. Well, I learned shit too. Now will you paint the damn circle?"

The younger Winchester dropped his gaze. His brother bent back over, finishing off the tail end of a symbol. Sam glanced at Jess, who was staring at him, pleading with him to see how crazy this was. He looked away. She hesitantly retreated to the car.

Maybe this was the easiest way to prove they weren't crazy. But he'd wanted to keep all of this from her, and now he was going to put her right in front of it. Put a demon in front of her. A being of pure evil – a thing that had vowed to kill her – and they were going to summon one. Just to prove a point. This was crazy.

Sam glanced at his brother. Dean was right: he had been gone for four years. And he'd gotten rusty. His best friend had been possessed right under his nose, and he hadn't noticed. Hadn't even suspected. And what Brady had said. Sam took a shaky breath.

The way he had described it…

It was just like his dreams. Just like them. He'd been having those dreams for days. Dreams of Jess, on the ceiling. Of… Of exactly what Brady had described. Said he would do to her. And he'd ignored them. If it wasn't for Dean, he would have let his best friend murder the love of his life.

He felt sick.

Not just rusty. Downright pathetic. Dad would beat the crap out of him if he could see him now.

But Dean… Dean knew what he was doing. Clearly, he and dad had been dealing with demons lately. He knew what was going on. He knew what to do.

Sam repeated it to himself like a mantra as he bent down and started to draw a circle to complete the pentagram.

When they finished the devils trap, Sam grabbed the holy water and his wallet out of the car, glancing hesitantly at Jess. She'd dug a jacket out of her hastily packed go-bag and wrapped herself in it like a security blanket. Right now, the car and that jacket were her comfort zone. They were the only sense of safety, however false, that she had out there in the middle of nowhere, watching her boyfriend and his brother paint occult symbols in the dirt.

Dean was digging a hole in the center of the pentagram when Sam jogged back over to him. He held out the cigar box, lifting the lid for Sam to slide his California issued license into. The older hunter shut the box pretty quickly, but not before his brother caught sight of dirt, some small dried flowers, and what he was pretty sure was an animal bone.

Wonderful. At least Jess hadn't seen the contents. That wouldn't freak her out at all.

Dean placed the box into the small hole and quickly covered it back up, burying any evidence that it was there.

"Okay," he muttered, retreating out of the circle with Sam. The two brothers walked back over to the Impala, where Dean dug into his front pocket and pulled out two necklaces. Small, coin-like charms dangled from the black cord.

"Put these on." He handed one to each of them. Sam did so immediately, without question, while Jess ran her thumb over the little sun symbol raised out of cheap metal. It looked like some two-cent Hollywood prop or costume jewelry you might find at a street fair.

No way was she feeding Dean's delusions.

"Jess." Sam nudged gently, taking the charm from her and sliding it over her head. "Trust me, okay?"

She really, really wanted to. But she wasn't crazy.

Dean was watching the center of the intersection with a hard, waiting stare. Sam adopted a similar stance and Jess, with no other option and an increasing sense of dread, turned her gaze to it as well.

When a woman in red appeared out of nowhere, Jess reeled. Sam was immediately there, in front of her, shielding her, wrapping his presence around her like a blanket without ever touching her. She gripped his arm and knew she was leaving bruises with her fingertips.

Her brain short-circuited. The woman – a brunette with perfectly curled hair, done up to the nines in a deep red cocktail dress that fit all her curves sinfully well – must have come out of the fields. Only, it wasn't like they were surrounded by fucking corn. It was all low-laying crop that someone her size, petite as she was, would have had to lie down in. And neither her dress nor her smooth, dark skin had a fleck of dirt present.

Jess couldn't look away. She'd blinked once and the woman had appeared. What would happen if she did it again? Her grip tightened around Sam's bicep and he reached back with his other hand to grip hers. She clung to it and every reassuring squeeze he sent her way like a lifeline.

Was she losing it? Had they somehow drugged her and this was all a hallucination? Sam wouldn't do that to her. Hypnosis, maybe? That would explain the woman coming out of nowhere. Maybe Dean did it with the coin necklace. Like those old time cartoons, swinging pendulum crap and all that.

Yeah, that's a lot closer to the 'sane' end of the spectrum than a demon. Let's go with that.

The woman in the red dress made a 'tsk' sound with her tongue, grinning like the cat that caught the canary. She clasped her hands in front of her, swaying sensually and oozing sex appeal. "Sam Winchester."

The woman's eyes were locked on her boyfriend and Jess finally had to look away or risk insanity. Her eyes. Her eyes were glowing red. Hypnosis didn't include hallucination.

If this was some sort of bad trip, she wanted it to end right now.

The woman walked towards them. Jess whimpered and Sam stepped fully in front of her.

Dean cocked his shotgun and the woman suddenly stopped, red eyes widening. "What the hell is this?"

Jess, unable to ignore this horrible delusion, looked back up. The woman was frowning at her feet, set right at the edge of the circle of paint. Her red gaze suddenly vanished, leaving dark brown pupils glaring at the trio with a murderous intent Jess had never seen in another human being. She didn't move any closer.

"Insurance." It was Dean who answered, unfazed. He took a step forward and threw something at the woman in red. She screamed as steam rose from her skin and she stumbled back, away from the spray of water.

Jess looked down at the metal canister in Dean's hand. Sam held an identical container.

The woman hissed and bared her teeth like a wild animal. Her skin was red and blisters were forming, as if the water had been boiling. Jess looked at the uncapped canister again. No steam rose from the metal opening. She looked back at the poor woman's ruined face and shuddered at the inhuman rage there.

Demon was sounding more and more probable.

"You summoned me!" she screeched, fisting her hands at her sides and stomping a high-heeled foot. Jess wondered if they'd broken some unspoken rule about summoning things. It certainly sounded like they had.

"Yup," Dean answered. He gave a grin that had no humor in it, and Jess wondered what had happened to the man who had obnoxiously commented on her smurf sleepwear. "And now we're gonna send you back to hell."

He began to speak, the words foreign but vaguely familiar. Jess's mind involuntarily supplied scenes from all those horror movies about possession and hauntings and demons that she'd watched as a teen. She'd loved them – loved scaring herself and curling up next to a friend or a boy or burrowing under blankets to peak through slatted fingers. She hadn't seen one in a while now – not since she'd met a boy who hated Halloween and monster movies with the kind of humorless self-deprecation of one who'd been personally offended by it.

She could kind of understand why now.

The woman screamed and wreathed and clutched at her choking throat. She fell to her knees, heaving up black, billowing smoke that defied gravity. It moved – slithered – as if alive. It writhed and wretched as it soaked into the ground. Soon enough, there was nothing left but the unmoving body of a woman in the center of a crossroads and a pagan circle.

Jess was trembling by the time Sam turned around and gathered her into his arms.

-o-o-o-

Overall, Dean thought Sam's girlfriend handled it like a champ. There was some shaking, and some denial, and she was probably a couple shades whiter than was healthy. But there was no screaming or wailing, no tears, and no running for her life or calling the cops. After dropping the still alive woman off at the farmhouse (and luckily Jess was too out of it to complain about the game of ding-dong-ditch-the-unconscious-woman-on-your-porch), she sat silently in the backseat as they continued on towards Bobby.

At least the woman had lived. Dean didn't really want to find out how well Jess took burying a body in the middle of nowhere on top of everything else.

Sam tried to climb into the back seat with her, probably intent to comfort her with his puppy-dog eyes and Sasquatch hugs. But she shook her head and closed the car door. His brother wrestled the hurt look quickly off his face and climbed into the front seat. Dean didn't say a word.

An hour into the drive, Jess released a shaky breath (the first sound she'd made since, well, let's call it the incident) and asked, "That….wasn't a bad acid trip or something. Was it."

It hadn't been a question, but Sam quietly answered anyway, "No. It wasn't."

She took in a deep breath. Dean met her eyes briefly in the rear view mirror. They steeled as she let the air slowly back out through pursed lips. "Okay."

"Okay?" he asked, arching an eyebrow at her.

She nodded and turned away, looking out the window. "Okay."

"Huh." Dean glanced at Sam, who gave a helpless little shrug before turning partially around in his seat to look at her. Dean looked over at the movement and frowned. "Damn it, Sammy. Seatbelt."

His brother ignored him. "Are you okay?"

Jess met his eyes, and he could see she was still shaken (who wouldn't be) but she gave a pretty firm nod. When she spoke, her voice was quiet but steady. "Put your seatbelt on."

He stared at her for a minute longer before he shared a small, sad smile. He settled back in his seat and did as she asked.

-o-o-o-

Two hours out of Sioux Falls, the sun started to rise once more and Dean decided it was safe to call Bobby to give him some heads up they were coming.

"This better be life or death, otherwise yer dead."

Well. Sort of safe.

The gruff voice was so familiar and so damn missed that Dean choked on his own breath, and then his lungs and his tongue and his throat, just for good measure. Tears welled in his eyes before he could stop them and he valiantly blinked them out of existence.

"Uh," Dean cleared his throat and tried to chuckle, but that, too, got caught. He pushed through it anyway, sort of sobbing out a humorless laugh. Awesome start. "Heya, Bobby."

There was a pause at the other end of the line. Dean wasn't that surprised about it, given the last time he'd seen Bobby in this timeline, but it still hurt like hell. The kid in him wanted to scream at his dead father figure (Not dead, Dean. Not yet. No, not ever) to say something. To prove he was still there and this wasn't all some cruel dream of a lonely, broken man.

"Dean?" He could hear Bobby's bed creak as the man sat up. "Dean Winchester. What the hell, boy."

"Sorry," he choked out and fought back a second wave of waterworks. Damn it, no chick-flick moments. "I know it's early."

"Yer damn right it's early. What the hell you calling me for at-" there was a pause and more creaking- "seven in the friggin' morning? Whatever this is couldn't wait?"

"Not unless you want houseguests still in your PJs," he joked back, and that's right – joking made this easier. Made him smile, because it was so damn good to hear Bobby's gruff voice again. Now all he was missing was the trademark 'idjit.'

"What? Yer coming here?" Bobby was up now and Dean heard him grabbing the shotgun he kept at the foot of the nightstand. "Something on yer tail?"

"Maybe, Bobby. We need you to prep the panic room."

There was silence on the other line and Dean could picture the old man blinking, stunned, before staring down at his phone like it was the offender.

Finally there was a grunt. "How you know about that?"

"Please, I've been all over your house. Like you could keep something that cool a secret." Dean looked out the driver window, pulling a grimace and hoping like hell the man would take the lie.

The silence was suspicious. The "uh-huh" even more so. But Bobby didn't press him; just asked when they'd be getting there and who all was 'they.' The surprise at Sam being one of the incoming party was only outdone by the presence of his civilian girlfriend.

"Damn, son. What kinda crap did you step in?"

The older Winchester swallowed the lump in his throat by pure force of will. "Oh, you know me, Bobby. Only the best kind."

There was a huff on the other line. "Idjit."

There it was. Dean grinned like it was Christmas and if he was blinking back tears again, everyone could shut the hell up. "See you in two hours, Bobby."

The line disconnecting was his only reply, and it made him grin wider.

-o-o-o-

Jess looked up at the old junkyard house as she closed the door to the Impala. Not that there was much to look at. The brothers were really going all out with this whole 'let's make sure very place we go could double as the set of a horror movie.' At least they'd arrived in daylight.

"So. Who is this guy again?" She glanced to her right, where a giant Rottweiler was chilling on the hood of a blue pick-up turned tow-truck that had seen better days. The dog turned sad, droopy eyes towards them, heaved a sigh, and went back to napping in the sun. Hell of a guard dog, that one, she thought.

Dean was grabbing duffel bags out of the trunk, tossing her and Sam's stuff to his brother. It was the younger of the two who answered, interrupted the first time around with an 'oof' as he caught his go-bag, thrown unnecessarily hard by his dick brother.

"He's… like our uncle. Sort of."

"He's a hunter. One of the best," Dean cut to the chase, shutting the trunk. He gave her a cheeky smile. "Dad used to dump us here as kids when we were too young to fight."

Sam leveled an annoyed look at him, but there was something else in there too: remnants of that stare he'd been giving him since Dean had woken up ten years in the past.

"What? I thought we agreed no pulling punches with her."

"No, you agreed. There are other ways to say it without making us sound like…like-"

"Like we had a crap father who raised us as soldiers?"

Yup. There was that look again.

Jess came between them, a hand on either of their shoulders. "Still right here, you know." She patted each of them twice before pushing through the brothers and marching up to Bobby's porch. She shouldered her bag and knocked on the screen door.

Dean raised his eyebrows before turning to his brother. Sam looked equal parts constipated and head over heels in love. Dean smirked. "I like her."

It turned out the old hunter could be surprisingly charming when he wanted to be (when Ellen immediately came to mind, Dean dropped the thought faster than you can say parental sex, because ew.) By the time the brothers carried their stuff into the house, double checked the wards, salt lines, and devils traps (God, did Dean love the paranoid old hunter), Bobby had Jess more at ease in his stuffy, dusty, book-lined house than she had been with either of the Winchesters since this whole thing started.

Sam tried not to let that hurt, and Dean tried not to laugh at his brother's award-winning impersonation of a kicked puppy.

They settled in the kitchen, Bobby leaning against the doorframe and the two brothers taking seats at the rickety table next to Jess. She was drinking a beer and digging into a freshly popped bag of popcorn.

"It's nine in the morning, Jess."

"I'm sorry, did you just have your entire world, belief system, and sanity brought into question overnight?"

Sam gave her such a hurt look that she stood up, got a second beer, popped the top on the edge of the counter, and handed it over. Sam accepted it with sagging shoulders. She offered him the open popcorn bag.

Dean was in fucking love. His brother needed to marry this girl yesterday.

While the sasquatch munched on some kernels and Dean was digging himself a handful as well, Bobby watched the surreal scene with a mixture of sympathy and exasperation. "If y'all are done gettin' comfy?"

Dean tried to talk through his mouth full of popcorn. Jess made a disgusted sound and Sam elbowed him in the arm. He had the decency to look guilty, close his mouth and resume chewing. Sam took over.

"Thanks for having us, Bobby."

"You wanna give me a little more info on why ya needed me to? Or what's chasing you boys?"

"Boy and girl, actually," Dean corrected as he swallowed heavily, stealing a swig of Sam's beer to wash down the ridiculously sized mouthful. He nodded his head at his annoyed brother and repulsed girlfriend. "Don't think the demons care much about me."

The silent 'yet' was not so silent, even to an audience that had no idea what was coming.

"Demons?" Bobby had straightened, pushing off the doorframe. "You got demons on yer tail? As in more than one?"

He looked between the two brothers, both of whom seemed sheepishly unable to make eye contact. Sam was wrecked, which Bobby supposed was on point. As far as he'd known, the kid had run away to college and gotten out of the life. If that had changed before all this, he would have heard about it. Which meant whatever shit they were knee-deep in had found him at school.

Dean avoided his gaze for completely different reasons. The old man knew him almost as well as Sammy did. And that didn't bode well for pulling off his whole 'nothing about me is different, nope, I'm not from the future or anything' gig. He'd pretty much blown it by hugging the man too long and too tightly when they'd first entered the house. And he definitely hadn't fled immediately afterward to hide the friggin' waterworks.

Were there allergies in November? There must be. No other reason his eyes kept watering all the damn time.

Bobby's eyes narrowed at them. "Alright. Spill it. Now."

They did. Dean let his brother do most of the talking. Sam seemed a lot less likely to accidentally slip up with information he wasn't supposed to know because he wasn't from the friggin' future. Dean considered that pretty solid reasoning to stay out of the story as much as possible. He added bits here and there, mostly so Bobby wouldn't get suspicious at his silence. Though, from the occasional looks he was getting, it wasn't working.

"Then we headed here," Sam concluded, looking over at Jess, who was hearing some of this for the first time. Her eyes were wide and she'd certainly had an interruption or two of her own when she'd learned that Brady had been a demon. Oh, yeah, and that they'd left him alone at the hospital recovering from two years of bodily possession.

Now she reached over and clasped Sam's hand, giving him a shaky smile. She was trying, despite all of it. Sam wanted to give that hand a grateful, loving, needy kiss, but decided to wait till they were alone. Dean had been waggling eyebrows like clockwork every hour since this all started. He really didn't need more fuel.

Bobby's eyes predictably turned to the older Winchester now that Sam had finished the story, including their little the-truth-is-out-there-and-we-can-prove-it stunt. Dean flinched instinctually.

"You summoned a crossroads demon?" The outrage in that sentence was worse than a disappointed parent and the kid shied away. "What were you thinking?"

He shrugged, standing up in a defensive push and heading for the fridge to get away from the man he considered more of a father than his own. A man who had, until yesterday, been dead, and was now ramping up for a lecture. It was too much to face without getting both choked up and pissed off and damn it, he was not going to fucking cry in Bobby's kitchen and blow this whole thing before he had fixed any of it.

Grabbing a beer, he spent a ridiculously long minute opening it, wasted a few more seconds taking an extended gulp, then finally turned around to face the music. "We had to prove it to her somehow."

"And summoning a demon was the first thing that came to mind, huh?" Bobby looked at the young hunter incredulously. Something wasn't adding up and he was determined to figure out what that was. "Why don't you just invite the damn devil over for tea next time!"

The bottle of beer shattered in Dean's hand, spilling foam and alcohol across the kitchen floor.

"Dean!" Sam was up and at his brother's side in seconds. He swiped a kitchen towel and pressed it into Dean's bleeding hand. The older of the two was ashen white. Bobby didn't miss the shaking in his hands as his brother cleared his palm of glass chunks and Jess fetched paper towels off the counter.

The injured hunter came back from whatever had gripped him, noticing the minor cuts as if for the first time.

"Shit! Sorry. I….Shit," Dean was rambling as he waved his brother off and grabbed the towel for himself, wrapping his hand. Bobby's eyes narrowed at the delay, which seemed dangerously like shock.

Something was up. Bobby had never seen Dean so jittery – so pent up. Boy was wound tighter than a mousetrap, and seemed just as ready to snap on a hair-pin trigger. And breaking a bottle with his bare hand? Bobby's eyes involuntarily glanced at the two remaining drinks on the table. That was one hell of a grip. Or one hell of a jerk reaction.

The question was, what had set it off?

Sam crouched on the ground, helping Jess clean up the spilt liquid and glass with paper towels and what kitchen cloths they had at hand. Dean backed out of the way, still a few shades paler than he should be. He rubbed at his chest with his uninjured hand, watching his brother clean up his most recent shit-show.

"You alright, son?" Bobby asked softly, treading carefully. He had no idea what had triggered him, but Dean was definitely not firing on all cylinders.

The older Winchester gave an absent nod. "Fine. Sorry. I-" He shook his head to clear it. "I haven't slept much the last couple days. I'm just on edge."

It wasn't a lie. He was on day three of no sleep, and while he'd gone on less for longer and in an older body to boot, it wasn't like he'd been in a stable place to begin with these last few days.

Adding Bobby to the mix had been rough enough. Now he couldn't shake the image of Cas's face, horridly contorted by Lucifer's smiling malice. The fucker would probably love a damn tea party.

He wanted to throw up.

Bobby nodded in understanding, but still watched the hunter cautiously. Dean helped finish cleaning up the beer and Sam suggested maybe they call it for now. His brother obviously needed some sleep, and he was fairly certain he owed Jess some alone time and no shortage of overdue answers.

Their host gruffly agreed, saying the panic room was prepped and the couple could have their talk down there. His house was warded seven ways to Sunday, but that was still the safest place they could be.

The two headed downstairs with their bags. Dean collapsed on the achingly familiar couch in the study, towel still wrapped around his hand. Internally, he weighed the option of the bedroom upstairs with its sagging twin mattresses and privacy versus the couch that still bore sharpie stains from one of their stayovers during Sammy's Picasso phase. Ultimately, he chose the couch. He'd deal with the backlash of waking up screaming from a nightmare if it meant he'd be ready to fight should demons figure out where they were.

He chose to ignore the other reason: not wanting to let Bobby out of his sight just yet. He was too tired to beat back the deep ache at the thought of leaving the old hunter, even if it was just to head upstairs.

Bobby settled at his desk with a stack of books on demons. Dean pretended he didn't feel the hunter's eyes on him every few minutes and instead focused on slowing his breathing. The scent of old spice and the turning of worn pages was a painfully missed lullaby. He prayed to absolutely no one he believed in that he wouldn't dream and fell asleep with his hand spread over his heart.