Fandom: Supernatural
Square Filled: Humiliation 
Pairing: Dean/Jimmy 
Rating: Explicit
Additional Warnings: Dubious Consent, Extremely Dubious Consent, Dead Dove: Do Not Eat, Serial Killer AU, Explicit Sexual Content, Verbal Abuse, Physical Abuse, Humiliation Kink, Humiliation, Bad BDSM Etiquette, Rough Oral Sex
Square suggestion by @sauvage-loup

Read on Ao3 or Below the Cut 

“You never follow directions,” Dean grumbled, shoving Jimmy into the motel room.

Jimmy tripped over the metal lip of the door, barely catching himself. Dean stomped in behind him, Sam and Cas following.

“I’m sorry -”

“Oh, you’re sorry,” Dean huffed, “well that makes everything alright then.”

Jimmy dared not roll his eyes. He wasn’t stupid enough to believe Dean actually meant that, especially when he was in a foul mood.

“You never think!” Dean snapped, throwing his duffle bag onto the floor. “Pathetic,” he growled, “all you have to do is what I tell you. But no. You get brilliant ideas and we almost wind up with witnesses. Real good work tonight, genius.”

Jimmy froze, only a foot or so into the room. He glanced toward Cas, who was making a very pointed effort of pretending like he wasn’t paying attention by staring at his phone.

“I – I,” the words refused to come. His heartbeat picked up and for the first time in a long time, he was actually scared of Dean. Usually, Sam was the more intimidating of the two brothers, but Dean definitely gave him a run for his money. Especially with the sharp jut of his jaw and the way his fists clenched.

Dean shook his head. “What do we do with him, Sammy?” He asked.

Sam’s eyes fell on Jimmy, giving him the once-over before he shrugged his shoulders. “What do you want to do?”

Jimmy gulped. There was a non zero chance Dean could kill him, or beat the hell out of him. They were murderers, after all. But he’d hoped Cas would step in before it got too far. Maybe he’d let Dean kick the shit out of him, but he wasn’t going to let Dean kill him. Not when they both knew Jimmy was really the only person who could put up with Cas.

Dean shoved Jimmy backward, knocking him off his feet. He hit the floor a little too hard, feeling it in his bones. His hand came down hard across Jimmy’s left cheek, stinging enough to make him feel like his eye might pop.

“Your mouth gets you in trouble,” Dean said, unbuttoning his pants, “let’s see if it can get you out of it.”

Jimmy glanced towards Sam and his brother, who were moving around behind Dean, acting as if nothing unusual was going on.

“You’re embarrassed?” Dean asked, his voice still carrying a hard edge. “Really? After all the shit you’ve pulled? Performance anxiety?”

Jimmy shook his head quickly, pulling his eyes back to Dean.

“Pathetic,” Dean growled. He shoved his pants and underwear down his legs, revealing his half-hard cock.

Jimmy barely resisted the urge to lick his lips. Dean had a nice cock, his anger notwithstanding.

Dean snorted, shaking his head, hopefully in amusement, as he gave himself a few firm strokes. “You’re a thirsty little bitch aren’t you?”

Jimmy gulped.

“Well? You gonna answer him?” Sam’s voice carried over from across the room. Jimmy peeked around Dean’s legs to look at Sam. He was sitting at the tiny wooden table in the corner, staring at Jimmy over the open lid of his laptop. “He asked you a question.”

“Don’t you have anything better to do?” Jimmy snarked.

“No, not really,” Sam said.

Dean then grabbed Jimmy’s ear, his blunt nails digging into the cartilage just enough to make Jimmy wince. “Don’t you talk to him like that,” he said, “you’re on thin fucking ice as it is.”

“Sorry,” Jimmy hissed.

“Well, answer the question,” Sam said again.

“Y-yes,” Jimmy stuttered.

“Yes, what?” Sam asked.

“Yes, sir. I’m a thirsty bitch, sir,” Jimmy said.

“That’s better,” Dean said. “See, all you gotta do is listen and do what we tell you.” His grip on Jimmy’s ear vanished, his fingers trailing through Jimmy’s hair instead.

Jimmy’s stomach was in free-fall mode. He was no stranger to the way Dean’s moods could turn on a dime, though the scolding was new. He wanted to end this as quickly as possible, to keep Dean happy and make the slight tremble in his limbs go away. Jimmy licked his lips, trying to keep his gaze focused on Dean’s face, hoping for something kinder in his expression and finding nothing.

“Open,” Dean said, “if you’re half as good at sucking cock as you are fucking everything up this should be easy for you.”

Jimmy opened his mouth but still wasn’t prepared for Dean to shove his cock in. He gagged when the head rammed against the back of his throat throwing his hands out to push Dean’s thighs away from him. Dean, however, pulled Jimmy’s hair, forcing him to remain where he was.

“Stop it,” Dean snapped. He slapped Jimmy’s hands away. “Keep your fucking hands to yourself.”

Jimmy stopped, letting his hands rest on his knees. Dean’s cock was still in his mouth, not far enough to choke him, but far enough that he was already starting to drool. And, to Jimmy’s horror, he realized he was getting hard. He shifted on the floor, trying to find a comfortable position that didn’t put too much strain on his dick.

“Look at you, making a mess already,” Dean said, “you like this don’t you?”

Jimmy gulped, trying and failing to keep his eyes on Dean’s face. It was too embarrassing to hold eye contact.

“You do! Little freak,” Dean laughed, dragging Jimmy by the hair almost all the way off his cock, then pushing him forward, showing him the pace he wanted.

Jimmy wanted to gulp, to swallow the spit and shame gathering in his mouth, but Dean wasn’t allowing it. He hedged a glance over to his brother, whose face was completely impassive.

Dean let go of his head, allowing Jimmy to bob and suck at the pace he’d already set. Dean’s hands traveled up his own body, lifting his shirt to pinch and twist at his own nipples. He groaned, hips bucking sharply, forcing a painful gag from Jimmy’s throat. “Tell me, Jimbo, is it the audience or is it the degradation?” Dean asked, “‘cause if it’s the audience I might just drag you out into the parking lot for the whole motel to see. I’m sure they’d love to see what a desperate little whore you can be. Hell, maybe I’ll let Sam have a turn, too. Or anyone who pays enough.”

Jimmy grunted, unsure of how to respond. He’d never been a fan of exhibitionism, even with as often as he found himself in scandalous positions in public. It didn’t do anything for him. The idea of being passed around, however, of being at the mercy of whoever Dean deemed worthy enough, now that was unfortunately thrilling. He squirmed, his pants much too tight for his shameful erection.

“What do you think, Cas? Fitting punishment isn’t it? He almost gave us witnesses so now everyone gets to witness what a slut he is?” Dean asked.

Cas hummed. “It could work. It’d be a decent way to make money, too.”

Dean snorted. “Yeah, considering he can’t hustle pool for shit.”

Jimmy closed his eyes and redoubled his efforts on Dean’s cock. Perhaps if he got Dean off soon enough they’d stop talking and he could will his erection away quicker. It was a challenge, not only with Dean’s silky cock in his mouth and musky scent of sweat and blood that hadn’t completely washed off but with the things they were saying, too. It was one thing to be turned on by fear; that was a phenomenon Jimmy knew all too well. It was another to be so turned on by the sheer idea of being used; of being treated like he was nothing more than an object to get off with.

“Bet you’d like that, wouldn’t you? God knows who’s come in your hair, some stranger’s cock in your mouth. That’s the most useful thing you’d ever do, you know that?” Dean’s voice was huskier, his head tipping back as he spoke. “That’s what your good for.”

Jimmy groaned, his hips bucking against his will.

Dean snorted. “That’s it. I know you like it. Of course, you do, slut.”

Jimmy tried to swallow a moan, but it out anyway, along with a lot of drool.

“Touch yourself,” Dean panted, “stroke yourself through your jeans.”

Reluctantly, Jimmy placed his palm over his cock, rubbing in time with his bobbing. It was maddeningly good, and almost enough.

“Knew you were a freak, Jim,” Dean said, taking hold of Jimmy’s hair and guiding him faster and harder, making him sputter and spit. “Next time. I’ll. Let you… Uhnnng…” Dean didn’t finish his sentence. Instead, he started babbling, alternating between swears and degradations, pulling Jimmy’s hair so much his skull ached. It all made Jimmy stroke himself faster, harder, begging himself to both come and not come at the same time. Dean was right, he was a freak, forever every sick thing he did inside and outside of the bedroom. And he loved every minute of it.

Jimmy’s orgasm took him by surprise. He gasped, stilling around Dean’s cock as he came in his pants. He hadn’t come in his pants since freshman year. But it happened, and the embarrassment came flooding over him, painting his neck and cheeks in bright red.

Dean noticed, of course, shaking his head and letting out a breathy laugh before thrusting in and out of Jimmy’s mouth. Jimmy was too embarrassed to bother trying to suck. Finally, Dean pulled off.

“Shut your mouth,” he said, stroking his cock, “you don’t deserve to swallow.”

So Jimmy shut his eyes and mouth, waiting for the hot splash of come against his face. Dean grunted, the wet sound of skin on spit-slick skin filling the air until he groaned, Jimmy caught Dean’s spend across the bridge of his nose and one eye. He waited for what felt like forever, hoping for more instructions. When he opened the one eye free of come to look up at Dean who was already turning away, tucking himself back into his jeans.

“Clean yourself up, will you,” Dean grumbled, “unless you want to walk around like a come doll all day.”