Work Header

The Sum Of My Regrets

Chapter Text



Dean’s standing in the middle of an odd pentagram while Rowena chants witchy gibberish. He can feel the power buzzing in the air around him. The hair on his forearms stands up and a shiver runs down his spine.

Sam, on the other side of the room and past the dark red demarkation lines, holds a golden bowl with assorted herbs and bones and whatnot, his face a careful mask that betrays how much he disagrees with Dean’s decision. Cas stands back, eyes fixated on Dean, and he looks guilty as hell.

He better, Dean thinks, but his heart isn’t in it. Or rather, it’s in it a little bit too much.

Cas is fiddling with his hands and his mouth works like he desperately wants to say something, but Dean shakes his head, and Cas’ lips vanish in a tight line. They’ve been over this, and Dean won’t back down.

After everything Cas has done for them he wants to give something back. His heart hurts when he thinks about the angel beating himself up about the death of an innocent. Listening to Ishim judging Cas for his decisions had reminded Dean all to clearly of everything Cas has lost. Yes, Sam and him have told him over and over that he’s family. Maybe it’s time to make true on that assertion and follow it up with action, even if it’s the dumb kind of action Winchesters use to show each other their... affection.

Dean tears his gaze away from Cas and meets his brothers’ eyes. Sam’s voice is rough when he says “take care”, and flicks a match into the bowl. The contents light up in a blue flame. It jumps to the sigils Sam drew onto the floor with Dean’s blood, and licks up his body. Rowena is still chanting. The spell pushes against his ribs, sucks the air right out of his lungs, and Dean wants to scream when the pressure builds.

The expression of disapproval and concern on Sam’s face morphs into panic and he turns to Rowena.

The room goes black. Dean doesn’t feel his knees hitting the floor.




He comes to with the smells of bleeding grass and moist earth filling his nose. Eyes adjusting, he focuses on a daisy right in front of him. He knows the spell worked because a) he’s outside and b) it’s spring instead of fall and so sunny his eyes fill with tears.

His hands fly to the bag he’s carrying – angel blade, some old dollar bills, a map and the penchant that hopefully will bring him back to his own time; if his plan works out.

Plan might be a little bit of an euphemism, though. He’d gone into this on half-formed strategies, cobbled together over a bottle of whiskey and seasoned with a good dose of thick-headed determination. Well, it’s more than he has most days when he rushes into action, so it’ll have to suffice.

Standing up, he dusts off his pants and sets off west where he can see a road in the distance.

Cas had come to him the evening after Lily Sunder had killed Ishim. He had stood in Dean’s room, fists clenched at his side, so hard four white points marked his knuckles. He hadn’t said a word for so long that Dean had grown restless. When he finally spoke, his voice had been thin and off.

“I let that child die,” he had said, and Dean hadn’t asked what he meant. He had gone over and tugged Cas’ reluctant, stiff body in a hug and he had held on until the tension slowly bled out of his best friend. He hadn’t told Cas that it wasn’t his fault, that he didn’t know and that he could have done nothing, because he hated it whenever people tried to placate him with bullshit like that. Because it didn’t change the fact that Cas felt responsible. Do you think I deserve to die?, Cas had asked in the church and Dean’s stomach still heaves at the memory.

Cas had trotted off to bed after a while, but Dean had lain awake for hours, before he had gone over to the library.

And that’s how he ended up here, clad in a Victorian costume that had cost more than the expensive ingredients for the spell, but less than Rowena’s help. He inhales the crisp spring air and relishes the sun warming his back.

Birds are singing all around him. With a start he realizes why they are so loud - because everything else is so quiet. He can’t remember the last time he didn’t hear any modern sounds at all. Even behind the thick walls of the bunker there’s the constant wheezing of the old vents, the labored huffs of the fridge and low hum of the laptops. The deep rumble of his baby and the backdrop of news and soap in the diners are so much a part of his life that he doesn’t pay attention to it anymore. It’s only now, with the absence, that he’s aware of that baseline of sound.

Before the nausea about the sheer stupidity of his plan can bubble up, he turns his face to the sun and promises himself to make the best of it. He’s gonna rescue a child and he’s gonna give Cas some peace of mind and keep him safe and then he will return home and have some awesome stories to tell about his trip to the past. When he finally reaches the road and turns left on instinct, there’s a new purpose in his stride and a small smile forms on his lips.




Orono, Maine dates back to 1774 when the first European settlers chose the area between Penobscot and Stillwater River to put down roots. They gave their town the name of Chief Joseph Orono of the Penobscot tribe that had welcomed the new Americans and had paid a high price for it. By 1900, about three thousand people called Orono their home, and the most remarkable thing about it is the University of Maine, founded in 1862 and specialized in engineering and agricultural science.

That’s about all Dean knows about the town he’s (hopefully) headed into. The reality of it sinks in only when he passes the town sign and looks up the main street. No cars in sight. No traffic lights or phones or modern clothes. Only a few people are milling around, women in the trademark silhouettes of Victorian fashion. Small hats sit on meticulously arranged hair, almost playful and in stark contrast to the serene morals of the time.

The men wear loser fits in subdued colors, but they seem to pay equal attention to their appearance. Dean stands and stares for a few minutes. He’s always loved to immerse himself in history, and at times he’s had to work hard to hold up the façade of grumpy reluctance when he and Sam had to dive into archives for a case. To be in the middle of it, without the immediate danger they had faced in Sunrise, Wyoming, – without having to fight a freaking phoenix – has him giddy with anticipation.

He tugs his bag higher on his shoulder, tips his hat to a mother with three children in tow who cross the street in front of him, and sets out to find Lily Sunder.