This is a Winchester-centric telling of this tale, which I wrote ages ago, obviously. Doesn't need to be read first to catch the gist of this one.
"You like this, don't you," Dean said.
They were sitting in the bushes on the side of a long, straight backroad in Tennessee in late October. It was clear and a little breezy, and they were waiting to see what happened by. It was one of those times when no one had died or gone missing recently; there was just a legend kicking up again, someone gossiping at a truck stop about Jack and his lantern being seen again. It was long since dark and not too cold, and a deadfall made reasonable furniture once Dean had reconciled himself to the fact that there would be a permanent bark pattern on his ass.
Not a single car had come by, and they'd been out there forever.
Sam knew way too much about old legends sometimes and told Dean every little bit about them without looking anything up. He'd always done that. It was nice having a walking encyclopedia, but when he got to one he favored, he never shut up about it. The whole Jack O' Lantern thing came from a traditional 18th century Irish Halloween tale where a man named Jack beats the devil but ends up cursed to walk the earth until Judgment Day, carrying a coal from the fires of Hell to light his way.
Yeah, whatever, a guy and a pumpkin. Dean knew another tale about a guy and a pumpkin but it was the guy who was a little lit and the pumpkin didn't even get dinner first.
Sam didn't bother to turn his head. "Not really."
"Yes you do," Dean said "Perverts love sitting in bushes, waiting to see something."
"Are we ever gonna have a conversation in this lifetime where you aren't busting my chops for something?" Sam said.
Dean watched Sam's eyes dart toward him and away in the moonlight, face dappled with leaves. He patted Sam's shoulder. "I'm sorry about your unrealistic expectations."
Sam sighed. "Me too. You just want this one to be real, don't you."
Dean kept looking at him. "It's probably not the original Jack," he said. "Would be cool, though."
"Legends get started for a reason," Sam said. "Be nice to see one that doesn't need to be killed off."
They were silent for several minutes. Then Dean said, "I'm gonna look around."
Sam watched him hop the ditch and stand in the road facing eastbound. After a moment, he followed. When he hit pavement, though, he checked the opposite direction, then used the back of one hand to slap Dean's shoulder. "Dean."
Dean turned to follow his gaze.
Right on the center line about forty yards down the road was a lit Jack o' lantern. The traditional three triangles and a crooked smile glowed yellow-orange on the asphalt without flickering.
"What the blue hell," Dean said.
They both had their guns out without even remembering that they'd reached for them, the motion too automatic for their brains to bothering recording. Any other time it would have seemed ridiculous, guns vs. a pumpkin, but being who they were gave them license to consider anything dangerous.
They stood and listened, guns held down along thighs, hearing nothing but the last of the year's leaves rattling in the breeze. It was easily just kids pulling an annual prank, or someone laying homage to a legend, or random weirdness. No way anyone had known they were there. They'd been too quiet.
They approached warily, keeping to their side of the road, Sam two steps behind Dean and to his right. There was no feeling of being watched, not sound of footsteps crashing away into the dark.
They stood on either side of the pumpkin, the glow lighting their faces from beneath. Dean nudged it with one foot. It rocked a little, but the light didn't change. The top was intact, including the stem, showing no cut marks. The pumpkin had probably been hollowed from the bottom. When Sam leaned over to look closer at the face, he realized he couldn't tell what it was lit with. There was no center point.
Uneasy, he straightened and looked up the road again. "We should just go back, see if anything else shows up," he said. When he got no answer, no christ Sam you're not afraid of a squash, are you? , he turned back to glance at Dean.
Dean and the pumpkin were gone.
"Dean," he said, turning a full circle. "Aw, damn. Dean!"
He couldn't stop staring at the light.
He had no idea why he'd picked the pumpkin up - it went against all common sense. It had wanted him to, and that was enough reason not to do anything but open fire on it.
Calling for Sam had done no good. He knew immediately that he was the one missing, not Sam, and knew he was no longer on the same road even though nothing about the way it looked had changed. He couldn't leave the spot he was in, though, because it was right where he'd been standing with Sam in the real world. He'd figured that much out, and so would Sam, and they'd break it somehow.
If only he could stop staring at the damn glow . It was so many yellows and reds and oranges, colors he didn't remember ever seeing before, colors that never shifted or blended. The gourd wasn't cold, didn't feel natural, but he knew it as a real pumpkin and not some toy. It had been grown somewhere . The shell was solid, the weight of it exactly what he'd expected for a pumpkin of that size.
The moonlight was gone, and the light in his hands was the only light anywhere.
He couldn't put it down. He'd tried, and it just wouldn't go.
"It's yours, you know," a soft mid-tenor male voice said just behind him.
When Dean turned, it felt like the air was full of spider webbing, the snapping of a million small threads.
The figure didn't reflect the light in Dean's hands, so Dean couldn't quite see him. It seemed that if he concentrated hard enough, the components would solidify into a face. The face was there, the form was solid, but his eyes weren't picking it up. The pumpkin had offered alternate shades of light that he could already identify, but the figure wasn't offering the same.
"You wouldn't have been able to touch it if it wasn't for you," the figure said.
"Who are you and where the hell is this?" Dean said. He was able to get one hand off the pumpkin long enough to discover he was unarmed.
"It's your last road, Dean," the figure said, and what confused Dean the most was the combination of menace and kindness that could be infused in one simple phrase.
"Great," Dean said. "Riddles, I can deal with those. Where's Sam, then?"
"On the other side of the road," the figure said. "But you already knew that. Your brother's got his hands pressed right against the asphalt, trying to figure out how this all works. The two of you are overlapping each other, and if you listen, I'll bet you can tell."
Dean swallowed hard and looked down at the road. No point shouting at the guy; he already knew it wouldn't get him anywhere. This was not the devil, and he was not Jack.
"He can call you all he wants," the figure said. "Sam's never going where you're going, Dean, even if he tries."
"What the hell's that supposed to mean?" Dean snapped. He was frantically trying to remember the rest of the details about the legend. Put a key in his pocket while eating an apple? No, that couldn't be right.
Heaven turned him away and hell wouldn't take him .
"C'mon," he said. "This is...this's crap."
"Your time's all borrowed," the figure said. "Take your turn."
For just a moment, Dean was so tired. It seemed reasonable just to walk away with the light, walk the road and keep walking, stop overlapping Sam.
"I don't know who or what you are," he said finally, "...but you're messing with the wrong guy this time. I'm not buying any of this. Put me back where I was before I kick your invisible ass."
The laughter was not human. "It's all your choice, Dean," the figure said. "Walk with me awhile longer. You've already been doing it for years."
Dean did turn and walk away then, so he didn't have to try and look at it or hear its voice
He felt an immediate sense of loss when he left Sam's spot on the road, and he realized it had been telling the truth at least that far. He didn't want it standing close to Sam, one step off reality or not.
It fell right into step beside him.
"So what do you want?" Dean said. If he kept it talking, it's say something it didn't mean to eventually; all these high and mighty badass wannabe demigods and demons loved to talk it up.
"Already got it," it said. "You're so well suited for walking between, Dean. Just do it for as long as you can, until you wind down. I'll be here."
Dean turned to tell it what it could go do , but it was gone. The suggestion of it was gone.
He stood, alone with the light that was not, knowing it wouldn't last forever even if it was made of stuff that never quite went out.
He returned to the spot he and Sam had last been in and struggled to put the pumpkin down again. He knew that wouldn't reverse it; it was no more a pumpkin than the road was a real road. It was the only action he could try to take.
It just wouldn't go.
He just wouldn't go.
He sat down where he was with the pumpkin in his lap. Walking would do no good. There was no end. There was no Emerald City, no goal, no final payoff or finish line. There was no point where he'd be able to say he'd gone as far as he could, he was done, he could lay it all down and call it good.
Sort of like the life he was already living.
"Not really," Sam said.
Dean turned his head. There were sitting on the deadfall in the bushes, waiting for Jack, having the same conversation. He spent a moment getting his bearings. He wasn't going to ask Sam if anything had happened. There was no point.
Sam looked at him. "Aren't you gonna say anything about how perverts like me enjoy sitting in the bushes?" Sam said.
Dean reached out and rested a hand on the back of Sam's head, pushing his fingers into Sam's hair. Sam froze and looked at him with open concern.
"I don't always have to bust your chops, right?" Dean said. Then he brought a rough hand down on Sam's knee and rose. "Let's get the hell out of here."
Sam watched him go in confusion. He waited until Dean reached the road, arms spread in impatience before he followed. Dean shoved Sam in front of him, pushing hm back toward where they'd left the car. He hazarded a glance over his shoulder.
The pumpkin, lit with something he understood better than he wanted to, sat on the center line.
He walked away and took his own road.