You shove the perpetrator into the wall roughly cuffing his hands. This was Dean Winchester, he had an impressive record on his hands. Destruction of private property, grave robbing, multiple fraudulent identifications, fake credit cards, shoplifting, drinking and driving, possible counts of homicide—the works.

He grunts as his face is pressed into the rough brick wall. It’s a shame his pretty face’ll end up in a mugshot.

“Woah, awful friendly back there, officer.” He might as well smooth-jackass his way through this until Sam can swoop in and bail him out. No biggie. He wouldn’t be a Winchester if he wasn’t arrested on multiple occasions. He feels you tighten the cuffs. “Y’know usually I’d take you out for dinner first, but -agh-“ His voice cuts off into a strained chuckle, a bit pained by the metal currently digging into his wrists.

Maybe he oughta settle down and shut up.

Mm. Nah.

His leather jacket creases where his muscles are forced back by the metal cuffs, before you can even think about letting him in the back of your cruiser you have to do a shakedown. You start to pat him down for lockpicks or weapons—you feel yourself hesitate—You can’t help it. Usually the guys you arrest are jackass slum bags. He’s an attractive jackass. And observant one apparently.

“Don’t be shy.”