Author's Note:

This fic is M for future events. That being said, it's also a slow burn, so there'll be a hefty dose of plot in here. Enjoy!

Prologue

The Trickster scowled at the sleek black Impala as it pulled out of the parking lot. The two hunters who had originally come after him were in the front seat, and the older hunter they'd called in for help was in the back. The Trickster was arguing with himself, trying to decide why exactly he'd done what he'd done. The Trickster did not like hunters. He certainly didn't let hunters who came after him live. He especially never let them think they'd kill him so they'd leave.

What the hell was wrong with him? Surely he had a good reason for letting all three hunters escape with a sense of victory. That just did not happen. If he boiled it down to bare facts, he was left with the realization that he had just kind of liked them all. Bobby Singer was a badass, Dean Winchester had balls, and Sam Winchester was smart. Plus, both of the brothers were really hot. Maybe he'd just always had a thing for tall guys. Was he really so shallow that just liking people let them off the hook for trying to kill him?

The Trickster followed the Impala down the road invisibly, debating whether or not to just blow up the car and get it over with. At least then he could stop arguing with himself over this.

The car slowed after awhile and dropped off Bobby Singer. The Trickster studied him for a moment as the older hunter got in a rust bucket of a car, then sighed and shook his head. He respected the man, in his own way, so he could go. This time. The Trickster tried to add the addendum to the end of his free pass for the hunter, but realized he lacked conviction. He just kind of liked the guy.

His attention went back to the Impala, where Sam and Dean were bickering over a road map. For some reason, he found it almost endearing that their brotherly bickering wasn't limited to him screwing with their stuff. They could act like brats with each other without his help. Dean tore the map out of Sam's hands, muttering something about incompetent shotguns, and Sam almost fell forward trying to get it back, his hair flopping in his face.

The Trickster sighed dramatically and turned away. No, he wasn't going to kill them. Much as he might hate to admit it, he did like the boys. It might even be worth his while to keep an eye on them.

Chapter 1 - You're An Idiot

This time, The Trickster was furious. All of that planning, all of his good intentions, all of that effort, wasted! All because Sam Winchester was the most codependent human being on the face of the planet.

The Impala was pulling out of the motel parking lot - Dean hadn't gotten shot this time around - and The Trickster could see that Dean was driving, but Sam was watching him like a hawk, as if he expected his brother to spontaneously combust.

The Trickster sighed. Did Sam really believe he was that untrustworthy? Add that to the list of reasons to be irritated with the idiotic human. He decided to follow them for awhile and see if maybe his lessons had been more helpful than he realized. Maybe Sam had learned something, although he really doubted it.

In the car, Dean was squirming uncomfortably under Sam's heavy stare. "What, dude?" He finally complained, flashing his eyes to Sam with irritation.

"Nothing, keep your eyes on the road," Sam rebuked him, tension rolling off him in waves.

"Are you still stuck on the Tuesday thing?" Dean asked, narrowing his eyes.

Sam snorted low under his breath. "Yeah, you could say that." It was less the 'Tuesday thing' and more the 'six months after Dean died on Wednesday thing.' Either way, he didn't trust that The Trickster would just let them go again. Once was weird; twice was too much.

"I'm not going to crash the car, Sam. Relax." Dean shifted again, still feeling overwhelmed by the intensity of Sam's presence.

Rather than argue, Sam just sat back in the seat, breathing deeply and trying to find a way to keep his eyes on Dean without creeping his older brother out. He didn't see himself relaxing from this little adventure any time soon. He was momentarily distracted by the little ringing notification on his phone that indicated a text message. Pulling it out of his pocket, he scowled quizzically at the new contact he knew he'd never added - tr1xtr. Well, three guesses and two don't count who that was. Apparently monsters were texting him now.

tr1xtr:/ You're an idiot.

Sam Winchester:/ You're a sadist. Why are you texting me?

The Trickster smirked at the phone he'd pulled into existence, somewhat pleased that Sam was actually responding. He knew he was way too focused on the hunter, but The Trickster had never invested this much time into teaching someone a lesson, then let them walk away from it without learning something just because they begged. Sam Winchester may have had some serious puppy dog eyes, but that wasn't it. At least, not entirely.

tr1xtr:/ Because you're an idiot. Which stinks, because you're a freaking genius.

Maybe if he shot for complementary, he'd actually do okay with this. Not that he really had an endgame in mind yet. For whatever reason, he just really wanted to make sure Sam was okay after Dean was gone. There was kind of a sick and twisted path waiting for the poor kid, and The Trickster was weirdly invested in trying to steer Sam away from it. He wasn't sure why yet.

Sam Winchester:/ I'm really not sure how to take that.

"Who's texting?" Dean asked, risking a glance at Sam, who seemed to have relaxed fractionally.

"Nobody," Sam replied, his tone irritated.

"Uh-huh." Obviously it was somebody, but if Sam didn't feel like sharing, Dean wasn't going to press it. Not now at least. With the limited time he had left, he'd really rather not fight.

tr1xtr:/ Take it for what it is, kiddo. You're smart enough that you should know better.

Sam scowled at his phone, not sure where the Trickster was going with this. Why the hell was he even texting the monster back, anyway? All he was was some freak's entertainment. Despite that, Sam found himself replying anyway.

Sam Winchester:/ I'll bite. Know better about what?

The Trickster rolled his eyes. Maybe Sam was a little dim after all. Had he learned nothing? Actually, that was a good question.

tr1xtr:/ What, didn't I teach you anything?

Sam Winchester:/ Nothing I didn't already know. You're an asshole and I'm going to be miserable if I can't save Dean.

The Trickster groaned and almost threw the phone away. Sam Winchester really was an idiot.

tr1xtr:/ Not if. He's going to die, and you're going to spiral unless you get over this codependency thing now.

Sam Winchester:/ Why do you even care?

That was the real question. Sam stared at his phone, waiting for the reply. Really, why did the Trickster even care about how Sam responded to Dean's death? Why had he let them go the first time they met? Why was he letting them go this time? Why was he freaking texting Sam to try and get his point across?

tr1xtr:/ Not sure.

Right, because that was an answer. Sam decided that was enough texting for now and put the phone back in his pocket.

"You all right?" Dean asked, taking his eyes off the highway again.

Sam shifted awkwardly and sighed, feeling drained. "Yeah, I'm fine," he muttered.

Dean knew that wasn't true, but wasn't sure what exactly he could do about it. Sam hadn't told him everything, he was sure of that, but he did know that somehow Sam had managed to live through one hundred consecutive days of Dean dying, and hadn't been able to stop it. Dean knew that if their roles had been reversed, he would be a wreck right now. The fact that Sam wasn't curled up in the fetal position sobbing was impressive as far as Dean was concerned.

Aware that Dean was still giving him a concerned look, Sam sighed again and sat up straighter in the seat. "Seriously, Dean, I'm fine. I'm just tired, I guess."

"Well, rest easy," Dean told him. "Today's Wednesday, and tomorrow's Thursday."

"That'd be nice," Sam replied wryly, running a hand through his hair absentmindedly.

Cycling through options of 'nice things to do for Sam,' Dean settled for offering, "You want to pick the music?"

Sam eyed him skeptically, then shrugged. "Anything but Asia. Or Huey Lewis."

"What've you got against Huey Lewis?" Dean asked, bewildered. The band had been on their radio this morning, if he was remembering that right, but he didn't understand why Sam had a problem with that. Asia he understood perfectly, and he would find a way to make sure Sam never had to hear the song again if he could help it. He understood bad memories and triggers.

"Just, no Huey Lewis, Dean," was all Sam said.

"All right, whatever you say." Dean reached into a door pocket and rustled around for a moment, coming back up with an Alice Cooper cassette. "This good?" He held it up for approval.

Sam wrinkled his nose, but let a small smile cross his face and he nodded. "Yeah, that's fine."

Dean popped the tape into the player, setting the volume at a reasonable level. He was completely aware that he was treading on eggshells around Sam, but he figured that his little brother needed a little TLC at the moment. They could get back to normal soon, but for now it was time to be careful.

The Trickster continued watching, not really sure why he was still following the Impala. He was very curious about the fact that Sam hadn't told Dean that he'd already had six months without him. Presumably Sam didn't want Dean to worry about him more than he already was, which was pretty self-sacrificing and well within the range of normal for Winchesters, at least from what the Trickster had observed.

Sam looked like he was trying to get a nap, zoning out as best as he could from the rock music. Dean was singing along, badly, and casting concerned looks sideways at Sam every few minutes, as though not sure what to do about his brother.

In some ways, the Trickster could feel a little bit guilty. Not that he wasn't totally and justifiably in the right here, but he may have been a bit overzealous in his attempts to play teacher. Then again, he'd never tried to teach someone a lesson for their own benefit before. It was usually a pretty formulaic job, being a trickster. Identify a jerk, figure out if said jerk needs to pay for his crimes through humiliation or death, then mete out an appropriately creative punishment. It wasn't hard. Sam, on the other hand, wasn't a jerk. He had a lot going for him, and the Trickster was forced to admit that he liked the guy. The Trickster didn't try to teach lessons to people he liked, because that was cruel. Maybe that was his problem. He'd applied a system designed for jerks to the one human he actually thought was all right. No wonder Sam was bitter. Well, the hunter would have to suck it up. The Trickster wasn't giving up on this without a fight. One way or another, Sam was going to see that he was headed down a path of destruction, and the Trickster would get him to course correct. He might have to find more friendly ways of helping though, or nothing would ever happen.

tr1xtr:/ Just so you know, I'm not giving up. I promise not to kill Dean again. Or you, for that matter.

Satisfied, the Trickster drifted after the Impala lazily, waiting for a response.

Sam felt his phone buzz again in his pocket, but he ignored it. The Trickster could wait. Sam was still trying to decide if he could let himself believe Dean wasn't going to die today. It was too much to have to deal with a texting trickster too.

The Trickster watched as Sam ignored his phone, but didn't dwell too much on it. It made sense that Sam would need some time. The Trickster had time. Dean didn't, which could be a problem, but ultimately, the Trickster's focus was Sam. Dean was a goner, but he might still have a chance to save Sam.

If only he could figure out why the hell he cared in the first place.