The first time Castiel time travels is the next day (Wednesday, March 8) in the middle of work. He doesn't know how or why or where he ends up, all he knows is that he's suddenly in a large warehouse between two groups of people (who are all quite well dressed) and there are guns. Lots and lots of guns.

He's terrified and confused all at once. The men (on both sides, oh boy this is looking up) are shocked out of their minds, but immediately start firing. At the other side? At him? Oh, most definitely at him. One side is not moving, just shooting at him with an accuracy that most movie villains have yet he still gets hit—just a grazing bullet in his right shoulder, but it hurts worse than one could imagine.

Castiel is tackled to the ground from behind, as they were moving towards him (and shooting too). He lands on the ground with an oomph, his left wrist most certainly cracking as it makes contact with the concrete from holding his bleeding arm. The man above him is firm—all hard muscle and broad shoulders—and is doing an excellent job at holding him down and keeping him there. He shoots, along with the others from his side and they eventually drive the opposing team away.

When the remnants of the other side finished retreating (or were lying on the floor dead) the man above him gets off his back, grabbing his good shoulder and lifting him up too. He expects a gun at his head and a short but intense interrogation of "Who are you?" and "How did you get here" that ends in his untimely death, but he is just pushed forward and to the outside of the warehouse. He's frantically looking around, trying to get some hint as to where he is when the doors open to reveal the outside world.

Cars. Ancient carriage like cars leisurely stroll down the streets at ten miles per hour. And the men are all wearing the same type of suits the ones in the warehouse were while the women are all dressed in long, revealing dresses with fur (is that real fox fur?) scarves and high heels that look painful to look at, much less walk in. He continues to look around, trying to find a newspaper, anything that could give him a clue to where he is, but his shoved unceremoniously into one of the ancient vehicles before he can see too much.

The car ride is short (that's really all he knew, they blindfolded him in the car), and they end up somewhere that smells a lot like smoke and cigars. When the car halts, his right shoulder is grabbed and Castiel yells out in pain. Despite being blindfolded, he can tell that people are starting to panic around him now. They keep asking him questions and shouting, but now that the adrenaline has worn off and the realization that he has lost a lot of blood has worn off, he's slipping into warm, safe unconsciousness before he has even left the car.

He wakes up on a leather couch. His trench coat is draped over his shirtless chest, which is covered in bandages (it's just a shoulder wound, why are there so many bandages?). He's looking at the ceiling—it's black; kinda boring for a ceiling—and tries to sit up, but is pushed back down by a firm hand when his chest flares with pain.

He angles his head better to get a view of his mystery helper only manages to catch a glimpse of slicked back blonde hair before the man disappears from view. Knowing he can't move without a risk of popping a majority of the stitches (stitches? For a grazing bullet?), he sighs and makes do with staring at the ceiling for the time being.

"You gave the doctor's quite a scare, young man," a deep voice vibrates around the room, "Well, with three bullets in you, you gave all my men quite the scare."

His eyebrows scrunch together in confusion, "Three bullets? I'm sorry, but you must be mistaken, sir; I was only hit in the shoulder."

A loud, mirthless laugh fills the room and before Castiel can ask why he is laughing, the man responds, "I wish I had more men like you. Most of 'em get shot at and run away screaming, despite denying it later. Yet you…don't even notice getting shot three times."

"Um, thank you," Castiel responds, a blush creeping up on his cheeks. He's still very confused, though, and has to ask, "If you wouldn't mind telling me, where are we and what is the date? And, um, who are you?"

The man comes into view now—blonde hair, forest green eyes, with a wide and broad chest—and smirks, "It's December 16, 1929, and we're in Chicago. I'm Dean Wesson."

Castiel lies on the sofa, eyes wide and scared, as he takes in this new information (1929? How is that possible? What's going on?). But he recognizes Dean, despite the new outfit and different hair style, and knows that what he says must be true. He trusts Dean—maybe not this Dean, but he did save his life. He's staring at him now, his eyes boring into the impossibly green ones, and all he can manage in return is a soft, "Oh."

He laughs again and brings up a chair to sit besides Castiel on the sofa (he's straddling it like Dean does in the bar). His eyes turn serious and he knows that this next question isn't going to one that he can answer.

"So, how's a guy like you just poof into our little fight back there in the warehouse?" His eyes are still open and honest, but Castiel can see the calculating, cold part of Dean that is brutal and ready to kill him if he doesn't answer this question correctly.

Castiel beings to fidget under that dark stare, but eventually mumbles out , "I-I really don't know. One moment I was at my desk at work, the next I was being shot at. Really, I swear."

It seems that that was the right answer, as Dean's eyes grow warm again and he smiles, "Alrighty then. Let's get you fixed up and back to work then, eh?"

Castiel stays for about a month in Dean's room in whatever building he's staying in. He sleeps mostly (now that the pain has sunk in, 3 bullet wounds and a graze isn't exactly paradise) but every now and then he gets up to watch Dean do his paperwork. He learns that Dean Smith is the head of the most ruthless gang in Chicago and that everyone fears him. That is, everyone but Castiel.

He helps out Dean as mush as he can, as thanks for letting him stay while he rests and figures out what he's going to be doing with the rest of his life, now that he's stuck in the 1920s. The Great Depression hits halfway through his stay with Dean and it's horrible (and quite fascinating too, to see how the world was effected in real life).

He's mostly better when Dean gives him a couple of fake ID's and passports (along with at least ten thousand dollars). Castiel is confused at the gesture, but Dean explains that it's probably better if he leaves town for a while, to escape the Depression, and that if thought he was going to be returning to his job and home, that he's probably lost it long ago.

Castiel agrees wholeheartedly.

He's packing up the little he has (the passports, money, clothing and suits that he borrowed from Dean) when he feels a eyes watching him. He turns to see Dean, standing in the doorway to his room—it's technically Dean's but during his stay, he's confiscated it. He zips up the last of his things and turns to face him.

"So, I guess it's time," Castiel says, eyes downcast. He's doesn't want to leave his friend, but he knows it was only a matter of time before Dean made him leave.

"I wish you didn't have to go," Dean confesses, suddenly much closer to him. His arms are twitching, like he wants to hug Castiel, but is suppressing the feeling.

"I thought you wanted me to leave?" Castiel asks, confused and slightly shocked at Dean.

"I would never want you to go," Dean looks away, green eyes dark, "You're the best friend I could ever have. I just don't want to look like I'm playing favorites with someone not even part of the family."

Castiel smiles a soft smile, "It's okay. I understand. I need to go anyway."

They stand there for a moment, before Castiel is hesitantly wrapping his arms around Dean, "Thank you. For everything."

Dean is solid beneath him, but pats him on his back, "You're welcome, Cas."

Castiel looks up at Dean, suitcase and ID's in hand, and disappears.