nightlost answered: dean’s the son of wealthy mob boss john, and cas is the awkward waiter/server who spills wine down his newest suit
see look Sara I spoil you
Dean looked up slowly from his pants, lips pursing together in annoyance. The suit wasn’t new, it wasn’t his favorite, but the liquid seeping into his shirt and pants was not going to come out. It wasn’t a comfortable sensation.
His father paused in his conversation a table away, looking at Dean carefully. Dean merely rolled his eyes before looking up at the server, already deciding that it wasn’t that big of a deal. He’d just see about a getting little bit of a more personal payment from-
Hello, Dean thought, his annoyance ebbing away. Wide blue, mortified eyes looked from the spreading stain on his abdomen before darting quickly up to Dean’s face. The waiter flushed crimson and began to stutter out an apology, but stopped abruptly as Dean stood.
His hands straightened the waiter’s lapels, smoothing them out before one hand firmly gripped the smaller man’s shoulder. The corner of Dean’s lips curled upwards into a smirk as he watched the waiter’s wide eyes flick down from Dean’s stern gaze to his plump lips.
“C’mon,” Dean said, his eyes glancing around at their company. The waiter seemed mortified but obliged, looking down at his feet as Dean escorted him out from the restaurant and into one of the offices in the back. Dean pushed the waiter into the room in front of him, closing the door before sauntering to stand in front of the smaller man, who was clutching his tray tightly to his chest.
“What’s your name?” Dean asked, stepping far too close into the other man’s personal space. The waiter didn’t move away, eyes flicking down to Dean’s lips several times before resting on his eyes.
“C-Castiel,” the man stuttered out.
“Well, Castiel,” Dean muttered, his arm snaking around the smaller man’s waist. He pulled Castiel in tight, the tray and the waiter’s arms pinned between their chests. Dean’s other hand cupped the man’s jaw, his thumb tracing over Castiel’s lips as a blush began to burn across his cheeks. “You’re going to help me clean up.”