Summary: Set in 1920s America. Sam doesn't want to be a cop, despite his dad's wishes, and he ends up stumbling into the life of a man named Crowley McLeod. He joins the mob, and has never found himself more fascinated than anything else in his life.
Word Count: 1519
Characters: Crowley, Sam Winchester, Linda Tran, Kevin Tran, Anna
Pairings: Crowley/Sam, Anna/Ruby
Tags: Mob AU, mentions of sex, mentions of daddy kink
Moving from Crowley’s speakeasy where the bar was smoky and crowded with people to the open air was refreshing, and Sam followed after the mob boss as quickly as he could. Despite Sam’s longer legs, Crowley’s gait was speedy, and Sam had to make an effort to keep up.
The bell chimed as Crowley pushed the door to the tailor’s open, removing his hat and blowing smoke out of the side of his mouth, keeping the grip on his cigarette with tightly pursed lips on the other side. “After you.” He said lightly, holding out a hand as indication for Sam to go, and Sam moved inside. The tailor front didn’t seem anything special, and he looked around for assistance before looking to the second bell on the desk.
The bell at the door tinkled again, and Sam jolted as Anna stepped inside. She’d put on lipstick, the bright red standing out compared to the pale her lips had been a few hours earlier, but it was smudged slightly. “You’ve been necking with that girl of Lucifer’s again, Ruby is-” Crowley started, but Anna held up a hand for him to stop.
“We don’t talk shop, boss, leave it out.” Crowley curled his lip, but he made no further comment as Anna turned to keep an eye on the door. Sam wasn’t sure what it was that made her such an invaluable bodyguard in Crowley’s eyes - while she was on the force, she didn’t seem all that much of a physical threat, and he saw no gun on her.
Crowley moved forwards and slammed his hand down on the bell, the ring of it resounding in the small, wood-panelled room. “Coming!” The voice was a young man’s, and Sam blinked at the dark haired tailor who came from the backroom. He stopped short when he saw Crowley, who beamed at the smaller man, but before Crowley could say a word the tailor yelled, “Mom! It’s the Scot!” Crowley made an expression of mock offence, but the boy’s remained stony.
The woman who followed out raised her eyebrows at Crowley, looking from him to Sam. “Kevin, go set up. We want a good suit, best quality, tie and all. Be ready to take measurements for shoes as well.” Kevin went from the room obediently, and the woman stepped out from behind the counter to take a closer look at Sam.
“Hallo, Linda.” Crowley purred.
“You’re paying me a lot for this.”
“Always, my dear, always.”
“You guys are friends?” Sam asked skeptically, and Crowley nodded as Linda shook her head.
“Sam, meet Linda Tran. The skittish creature in the back is her son, Kevin.”
“Mrs Tran.” Sam greeted softly with a quiet nod.
“He’s respectful, at least.” Linda murmured under her breath, looking at Sam up and down. “I can work with this. Are you ready to be fitted, kid?”
“Yes, Ma’am.” Linda nodded, and then indicated for him and for Crowley to follow her into the other room, where Kevin had laid out a measuring tape on the side. Linda moved forwards, beginning to use the measure and read out numbers to Kevin, who noted them down.
Sam looked at himself in the mirror as she worked, glancing to Crowley in the background of his reflection. Crowley was watching intently, lips pursed as he concentrated. He met Sam’s eyes in the reflection in the mirror, and Sam offered his new boss a tiny smile. It wasn’t forced, but it was nervous all the same, and Crowley’s lip quirked.
“How long will the suits take, Linda?”
“Two days, tops.” Sam swallowed as he considered what this meant. It was just a few suits, right? Sugar daddy. That’s what Alastair had called Crowley earlier, had said he was Sam’s sugar daddy but dear God, it was worse than that, so much worse than that. He’d said at the beginning he didn’t want to kill anyone, but could he kill anyone? Would he, if Crowley asked?
Shit, shit, he’d just joined the fucking mob. That was what this meant, getting a suit and getting all the other employees to be friendly with him and lying to his dad and to Dean about what he was doing for a living, and shit, shit, he might have to kill someone.
Sam thought about the way Crowley had fucked him last night, how good he’d felt, how much he’d needed that attention, how much he wanted more. Sam bit at his lip, worrying the skin as he stared at his reflection in the mirror. Was he capable of murder? Wasn’t he allowing people to die, to be hurt, just by being part of the whole thing?
Linda snapped the tape measure away, and Sam jolted in surprise. “You alright, Sam?”
“Yes, Ma’am.” Sam said in a little voice, and Linda looked at him with some concern, sharing a glance with her son. “Just feeling a bit peaky.” She and Kevin both nodded, and Kevin left the room with the notebook in his hand, ready to get working.
Crowley handed Linda a few dozen banknotes, and Sam swallowed, considering where that money had come from, and then something in him steeled. He’d seen his dad with piles of banknotes before, from the police fund, from their home safe, from all sorts of places - and yet his dad had never gotten jackshit done. Sam knew that some of that money went into real things, real important things, but most of it didn’t.
“You feeling alright, kid?” Crowley asked as Anna stepped aside, allowing them to step into the street.
“I’m fine.” Sam decided after a moment of pause, lips pressing together, his back straightening. “I feel great, actually. Thank you for the suit.” And Sam paused, and he thought about how Crowley had told him not to call him sir, about how Crowley insisted none of his important employees called him sir and how only his lackeys did. “Sir.” He added, and Crowley and Anna both raised their eyebrows at him.
“What did I tell you about calling me-”
“I want to call you sir. Better ring to it than Daddy.” Sam interrupted his boss, and his blood ran cold as he considered the potential risk of doing so, but Crowley laughed - laughed.
“Sir’s a good deal preferable to Daddy.” Crowley purred, and he stepped closer. Once they were inside the speakeasy, Crowley reached up and grabbed at Sam’s hair, pulling him down and into a quick kiss, biting and nipping at his lips until Sam was breathing heavily, eyes wide as Crowley let him go.
“Get upstairs and bend yourself over my desk.” Crowley murmured in his ear, and Sam took in a slow breath before nodding obediently.
“Yes, sir.” Crowley was grinning as he watched Sam move away.
The trousers were the perfect length, the shirt was simultaneously snugly fitting and loose enough to be comfortable, and Sam had never felt so right in a suit before. He put the tie around his neck and tied it in a neat knot, tightening it up to his neck before fastening the tie pin Crowley had given him into place.
The waistcoat next, and Sam fiddled the with the fastenings on his cuffs before he buttoned it up, and then it was the jacket. Sam swallowed as he examined his reflection in the mirror. The shoes fit him perfectly, it all did. Sam hadn’t asked how much the suits had cost, but he didn’t think he needed to, now - the quality spoke enough that Sam knew he would probably feel embarrassed to know how much Crowley had spent.
Crowley met his reflection in the mirror again, and Sam gave a small nod. The boss took a few steps forwards, laying his hand possessively on Sam’s lower back as he looked at the both of them in the mirror. “I think that suits you quite perfectly. Did I tell you the Trans were artists of their trade?”
Sam chuckled a little, despite remaining a little nervous. “You didn’t, but I’ve noticed.”
“Are you quite sure about all this, Sam?” Crowley asked, and Sam knew in an instant he didn’t mean the suit.
“Never been surer of anything in my life.” Crowley grinned, and the expression was predatory, possessive, excited, all of those things at once. Sam grinned, and he noted the similarities between his expression and Crowley’s, but shoved them to the back of his mind for the time being.
“What a pretty, perfect little corruption this has been.” Crowley purred, and Sam nodded. “Now, come, moose, we’ve a bill to pay.” Crowley moved away, and for a moment, Sam stared at himself in the mirror. He grinned at his reflection, and winked at himself before he turned on his heel.
Perfect corruption was definitely right in Sam’s book.