Chapter Text
Day 36.
And Dean was getting tired. Same old salad order from the place Sam went too, thirty-six times over in this stupid loop. Until he noticed the one change. The guy who ordered croutons with his salad hadn’t ordered this time, Maybe this was that fucking trickster, and he could finally catch the jackass.
They knew how to kill him, nonetheless, but he got up, muttering to Sam something about going to the bathroom, before walking that direction and following the guy as he left.
He walked down an alleyway with the guy, discreetly in step behind him and shoving him against the wall, pinning him there and looking at him with almost a deathly glare.
“I know it’s you, you son of a bitch.” Dean practically growled under his breath, narrowing his eyes at the guy just as he changed back to his normal form right under him.
“You’re right. You caught me, was it ordering no croutons? I hate those things.” The Trickster said, almost annoyed about the fact he had to be ordering croutons every single loop, it had been 36 times of eating croutons.
“Why’re you doing this?” Dean asked, finally stepping back and away from the Trickster. It’s not like he could fight him off, he wasn’t prepared in the slightest for that right now. No wooden stick, nothing..
“Because I like watching you slowly but surely descend into some type of madness, Dean-o. It’s really entertaining to watch.” The Trickster said, grinning as he stretched a little, popping his back slightly, and looking at Dean..
“And I can say, it’s going pretty well so far if I say so myself.” The Trickster said, still grinning at Dean as he looked like he was processing it.
“So you’re saying that you.. Are doing this purely for your entertainment? God you are a sick and twisted bastard, you know that?” Dean said, voice low, angry. This was tearing him apart from the inside fucking out. And he couldn’t do anything about it unless he caught this guy again and had that wooden stake with him this time.
“Oh yeah, I know. I’m very aware.” The Trickster said, before disappearing, leaving Dean alone in that alleyway to deal with the whole flood of emotions he had right now. It had been 36 loops, 36 days, 36 Thursdays. It was driving him crazy.
He let out a frustrated grunt and hit the concrete wall with his fist. Before he heard the sound of a gunshot, people were screaming and then the whole loop reset again.
Day 37.
Nothing felt like it really mattered anymore to Dean. Why get out of bed when his little brother was just going to keep dying, again, and again, and again. Over, and over. Last time it almost worked, he had stayed under the covers, in bed, not acknowledging Sam until 11pm when he had to really go use the bathroom but..
He wasn’t sure if it’d work if he tried it again.
“You finally up, Dean?” Sam said, the disapproving tone evident in his voice. Maybe The Trickster changed something, because it sounded more real. Or maybe he was trying to convince himself it sounded more real so it seemed more fake.
“No. Go do your shit alone today, okay? I want to sleep in.” Dean said, even if it was a little harsh he didn’t care anymore. He had spent 37 loops trying to convince himself everything was fake when he could feel it all under his fingertips.
“Come on, not even for salad?” Sam teased, knowing Dean hated salad. “No, not even for salad. Go buy your own.” Dean said, getting under the covers and turning to face away from Sam, and facing away from the door.
Dean was getting tired of doing this again and again. He just needed it to stop, something to confirm that all of this was real. He didn’t know what was even real or what was fake. The birds chirping outside of the motel could be the tricksters doing for all he knew. The cars driving by, the honking of their horns.
He was starting to notice those small details less and less, he didn’t need to pay attention to them. He didn’t need to catch the coffee that almost fell every time he went to that stupid salad place with Sam, that after he got back and explained the situation to Sam, was never going to go again. No way in hell they were ever going to go to that salad place.
He just wanted to get out of Sturbridge Massachusetts, but it was impossible too. He had tried that on Day 17 and had only gotten across the state border before the loop reset again and he had woken up in bed.
He fell back asleep in bed after Sam left, the silence of the motel was louder than the slam of the door closing ever would be. He woke up a good couple hours later, frantically knocking on the front door. He contemplated opening it, before deciding to just open it.
Bobby?-
The loop reset.
Day 38
He woke up in bed again. How the hell did Bobby get there, one? Two, the loop had reset quick after he saw Bobby, which meant that maybe Bobby wasn’t meant to be there. That Bobby had found a way in, to try and get him out. Maybe, just maybe Bobby had been real.
“You finally up, Dean?” Sam said, the disapproving tone still there. It didn’t seem as pronounced as it had in the last loop, but it had definitely been there.
~~~~~~~~~~~~
Bobby had known that Dean was stuck somewhere. Bobby didn’t know where exactly yet, but he was trying to find his way in. He only had limited knowledge though, and didn’t know everything. But when he had finally done some spell he found, and it got him to a motel in Massachusetts.
He had knocked on the door that he assumed Sam and Dean's room was in, knocking almost frantically. The door opened, revealing Dean standing there clad in a pair of sweatpants and a grey T-shirt.
But before he could say anything, it all went dark, and he woke back up at his desk in his house.
What the fuck had Dean gotten himself into?