A/N: Hey guys! This fic was inspired by a video edit I did for my gayfandoms Instagram account, and a follower asked me to actaully write the AU, so here it is! It's still a working progress, and the first Supernatural fic I've uploaded, so please review! Thanks, hope y'all enjoy!

"So it's settled. No ones signing any papers until I get down there on Wednesday. No no, you've been very helpful. Alright, have a good weekend. Yeah, you too."

Dean Winchester hung up the phone and threw it back down on his desk, letting out a sigh as he ran a weary hand over his face. Working overtime to sort out his Boss' mess was not what he had planned to be doing on a Friday night, but there he was. For the second time that week he'd had to cancel his dinner plans with Lisa, and boy had he gotten an earful. She was sick of it, he was sick of it, but there was nothing he could do, he'd pleaded with her on the phone. He'd make it up to her, take her out at the weekend, buy her something nice. The only response he'd gotten was the click at the end of the line as she hung up.

Dean sat back down at his desk and began sorting through the numerous files piled skyscraper high, putting his girlfriend out of his mind. He glanced wistfully at the clock. One more hour...

Outside, thunder clapped, so loud it must have been right over the building. It didn't scare Dean, who was used to it by now. As his phone started ringing for the fourth time that hour, he stared out of the window. Rain was pounding down on the New York streets, a cold and bitter wind whipping through the city. He reached for the receiver, counting his lucky stars he wasn't caught out in the storm.

Meanwhile, tucked into the doorway of an old music shop, Castiel settled down for the night. As another flash of lightening illuminated the sky, he pulled up the hood of his sodden jacket, wiggled his numb toes around in his disintegrating sneakers, and leaned back into the doorframe, closing his eyes. By now he was used to the numbing cold, the stench of mouldy clothes, the hard concrete mattress. He was also used to the painful growls that his stomach emitted, just to remind him that he hadn't eaten that day.

Castiel sighed, giving his toes another squeeze as the next thunderclap sounded. It would be a while before he could sleep tonight, with the bitter breeze biting at him and the rain soaking into his shoes. What he wouldn't give for a blanket right now...

Of course, that was his own fault. He'd had a blanket, bought cheap at a thrift store with change he'd saved for over two months. It was a dark blue cotton one, long enough to wrap himself in and keep him a little warmer. God, he'd cherished that blanket. You needed one, living on the streets of New York in miserable October.

But of course he didn't have it for long. A week, that's all. He was looking for a place to settle down for the night, somewhere quiet and sheltered from the looming black clouds, when he'd seen her. A young girl, no older than twenty, with greasy ginger hair and dirty finger nails. He hadn't hesitated in handing over his one possession, insisting she keep it. The homeless girl had resisted, hesitated, and nodded a thank you before curling underneath the material, shrinking away from him. And so he'd walked on.

Which is why Castiel found himself without a blanket, huddled in a shop doorway, on the same night that Dean Winchester decided to get some pie before going home.

"Hey excuse me? Sir?"

Cas jumped, falling from the doorframe and struggling to stand and face whoever thought he was a sir. Dean Winchester stood in front of him, raindrops glistening in his hair and soaked shirt clinging to his skin. Cas took one look at him, and groaned internally. Great.

Dean cleared his throat. "I, er, I just wanted to ask if there was anything I could do for you, man, it ain't pleasant out here."

Cas' cheeks burned red and he cleared his throat, pulling his jacket tighter around him. "Thank you, but no. I'm pretty used to it all by now anyway."

Cas turned to settle down again but Dean didn't go away. He was looking at Cas with a pained expression, shifting his weight from one foot to another anxiously. He didn't appear to be leaving. Cas stated at him in confusion, until Dean finally broke the silence.

"You like pie?"

Cas frowned, unfamiliar with the icebreaker. "Um...yes?"

Dean nodded, seeming to make up his mind. "I'm gonna get you some pie."

At that, he turned and walked hurriedly away from Cas, who watched him go in disbelief. Out of all the strangers who could've found him stinking up an alleyway, it had to be multimillionaire Dean Winchester.

Ten minutes later, the man himself jogged back into the alley, carrying two wrapped pies and a grin on his face. "Cashier gave me one for free when I told her it was for you - c'mon, we'll eat in the car."

"Th-the car?" Cas frowned, not moving from his seat, smelling the pie and hearing his stomach cry out again.

Dean shrugged. "I'm not gonna buy you pie and then make you eat it out here. C'mon, I'm parked two blocks away."

"Look, Mr. Winchester-"

"You know who I am?"

Oh, Cas knew who he was alright. He'd seen the man's face on the billboards, been enticed by his smile in the papers, watched his interviews from crappy TVs in crappier bars. Who didn't know who Dean was, the man who had saved a billion dollar company from collapse at a mere twenty two years of age. When offered the position of CEO, he'd turned it down, settling for Manager of the Financial Department, where he'd stayed happily for the last five years. He was a mystery wrapped in an enigma, he was charismatic and charming, he was intelligent, witty, and shockingly attractive. Often seen on the front of the New York Times with his younger, and no less attractive brother Sam, who ran another successful business in the area, his face was a stranger to no one. Cas had found himself thumbing through papers on a Saturday morning, searching for Dean's smile, Dean's eyes twinkling back at him. As far as celebrity crushes go, Cas had a pretty big one.

Blushing, Cas nodded. "I've seen you in the paper a few times."

Dean smiled humbly and leaned forward. "Then it's not like I'm a creepy stranger trying to lure you to my van, I mean we're practically besties," he joked, and Cas couldn't help but grin.

Dean placed a hand on Cas' shoulder and pulled him gently to his feet. "C'mon. You don't deserve to be sitting out here alone on a night like this."