Disclaimer: I own neither Supernatural nor anything vaguely related to it. They're Kripke's characters, they just follow me around.
The Winchester brothers have spent the majority of their lives in cheap motels, greasy spoons, and the darkest back roads America has to offer. Throughout these twenty-plus years, Dean has come to feel at home in such places, blending in wherever they happened to stop as though he were just another local. Waitresses never gave him a second glance (unless that was his goal) and store owners never watched him a little more carefully to make sure the out-of-towner didn't steal anything. And although the brothers avoided any and all law-enforcement like the plague unless interaction was absolutely necessary, local officers usually gave Dean a short nod in passing, if they didn't ignore him entirely. Sam knew it had something to do with the infamous "Dean charm," that air of confidence that has gotten them out of—and into—more messes than Sam would like to remember. Dad had been the same way, able to fit in anywhere and talk his way out of any situation, no matter how screwed to hell they probably were at the time.
But Sam? Sam was the one who usually got the second glances from waitresses that just shouted What're you doing around here, kid? Sam was the one who got watched when he ran into quik-marts to pay for gas or pick up some food. Sam was the one who got stopped by the cops for a license and registration check when Dean made him do the footwork on a job. Sam may as well have worn a sign saying, I'm up to no good! Ask me why!
Sure, he had the "puppy dog eyes," as Dean had labeled them, but that particular skill only came in handy when they had to get information out of a distressed witness or grieving relative, not when they needed to persuade a security guard to leave his post or convince a doctor to hand over sealed medical records. No, for those situations, it was all about Dean taking the lead with his fake badges, cheap suit and "You'd better not question my authority" smirk while Sam nodded intently beside him, taking cues like the good little actor he'd become.
Sam figured it was hereditary. Dean took after Dad with his endless supply of confidence and "Screw you" attitude, and Sam was probably more like Mom than he'd ever know, because he was pretty sure Dean wasn't going to feel like caring and sharing any time soon. It wasn't that Sam hadn't tried finding out more about what Mom was like, it was just that, whenever he did ask, Dean would usually give him a look and make a subject change before the conversation even got off the ground.
Essentially, Sam was the black sheep in a family of black sheep.
And it was precisely that reason that he loved working these kinds of jobs.
A local college had a string of unexplained illnesses and deaths linked to one of the dorm rooms. The thing was that the room had a bloody history—guy slit his wrists after finding his long-time girlfriend cheating on him in his room with another guy. First it went that any girl who stayed there would get sick after moving in and end up on life-support before a month was up. The last victim was a guy in ICU, breaking the all-girl pattern. They'd heard about it in passing and it sounded right up their alley.
It had taken a little convincing, but Dean had eventually agreed that the best way to work this one was from the inside, which meant that they had become transfer students to Lake Hills College. This also meant that Sam would be in his element for once and Dean would be relying on him to get by unnoticed.
Sam couldn't help but grin for the thousandth time as the brothers carried their duffels up the front steps of the infamous Benet Hall, the dormitory they'd been assigned to for the next semester.
