“Please,” Sam begged one last time. Defeat was heavy in his voice. He knew without the Trickster's help there was nothing he could do to save his brother. He'd already tried. He had nothing to hold over the Trickster's head and nothing to threaten him with. After spending so much time trying to hunt the bastard down, he was tired. He just wanted it to be done. He wanted Dean back.
The Trickster sighed heavily and rolled his eyes. “Fine. You want your brother back so badly. I'll make you a deal. But only because clearly, you still think you're hot shit chasing me around, thinking you can kill me and demand your precious brother back. So, the deal's this. You get your Ken doll back but, you're going to gain some humility. A lot of humility. In fact, I want to see you getting off on nothing but pure humiliation. Then, you'll get it. Because, Sammy, nothing in this world is yours to control. Even old Deano's gonna know just how badly you need to be put in your place. I'm going to make sure of it.”
The Trickster laughed to himself. “Yeah, by the end of this, you'll be begging the hounds to come for him.”
“A humiliation fetish? That's your play?” Sam scoffed.
“Take it or leave it, pretty boy.”
“Then why don't you come over here and seal it?” The Trickster winked.
--- --- --- --- --- The next day ---
Sam finished explaining his story to his fresh faced and very alive older brother. Dean looked ready to wring somebody's neck.
“Tell me you ganked that son of a bitch?” he growled.
“No, he got away. I'm just lucky he agreed to bring you back that last time.” Sam stared down at his shoes. So far, the Trickster's deal hadn't caused him any trouble, but it had only been a couple of hours. So far, the worst of it were the invasive thoughts about the woman working the register at the gas station and then when he was watching Dean put his boots on...
“'Agreed to'? Don't tell me you made a deal with that bastard. He's a trickster, Sam! It's in the name.”
Sam flinched when his brother yelled. “It's not like that, Dean.”
Dean sighed. “Shit.” He laughed humorlessly. “I know exactly what it's like. I've know this whole time I just... I didn't want to say anything.”
Sam's stomach dropped. His cheeks turned red. “W-what are you talking about?”
“That bastard. What the hell kind of deal is that anyway?” Dean was on his feet now, pacing the floor.
Sam shrank into himself. “What are you talking about?” he said again.
“Your fucking humiliation kink that's what! I don't why I know, but I do. I know all about it.”
“Yeah.” Dean looked at his brother who was blushing and clearly embarrassed. “Hey, it's okay, Sammy. We all like weird shit in bed. This isn't really all that weird.”
“Seriously?” Sam raised his eyebrows.
“Seriously. Besides, I think this could be good for you.”
Dean put a hand on his brother's shoulder. “You're always wound so tight. Let me help you with this. It'll be a great way for us both to blow off some steam.”
“We're brothers, Dean. We can't just...”
Dean pulled away “What? So it's only okay for us to have sex because we're drunk? Or because one of us is dying? Or because you thought I was going to be mad at you for not hiring a stripper for my twenty-first? It's not anything new, Sam. We just don't have to lie to ourselves about it anymore. I'm tired of it. Let me give you what you need. I promise I'll take care of you, Sammy.”
Sam kept his eyes down on the cheap linoleum floor. Old habits held him back, kept him from admitting what he wanted out loud.
“This is what you want right? Because if it isn't I swear I'll hunt down that Trickster and chop him into pieces. It might not kill him, but it'll take him a while to put himself back together.”
“No, Dean... you can't do that.”
“I can and I will. Unless you tell me different.”
Sam couldn't let Dean do something like that no matter what he wanted. The Trickster might go back on their deal because of it. Still, that didn't mean he didn't want this.“I want it. I want us to...”
“Are you sure?”
“Yeah.” Sam finally looked up at his brother. He didn't see a hint of mockery in his face. Dean was totally on board with this. Even more than that, he looked excited about it.
“Great,” Dean smiled. “'Cause I think you're gonna love this.” Dean turned on his heel and all but skipped over to his duffel bag. He faced Sam again now holding a pair of satiny pink panties in his hands. Sam moaned.
“You're gonna wear these for me.”
“Yes,” Sam said without the smallest hesitation.
“You're gonna be my pretty girl,” Dean's voice was deeper now, lower.
“Yes,” Sam said and his voice broke.
“Get down on the floor and crawl to me.”
Sam whimpered as he slid to the floor. He crawled across the room to his brother, mindful of his body, trying to look graceful despite the way his hands shook and his cheeks burned. He knelt on the floor and looked up at his brother.
Dean held his chin. “Strip, Sammy. I want you in nothing but these pretty pink panties.”
Sam shivered. In a split second he was on his feet shucking off his clothes like they were on fire. Dean winked as he handed his brother the panties. Sam couldn't even look at his brother as he slid them on. The soft and silky fabric caressed his cock and between that and the complete humiliation of his older brother seeing him such a state, he could have cum on the spot if he wasn't trying to hard not to.
Dean ran his fingers through his brother's hair. “You make such a pretty girl, Sammy.” He pulled him close with one arm and Sam melted against him.
Dean reached one hand around them to fondle Sam's balls through the satin. He gave his brother a filthy kiss.
“You're gonna be such a good fuck toy for me aren't you, Sammy?” Dean growled.
Sam whined in agreement.
“Get back down on the floor. I want to see you rubbing that cock through your pretty panties.”
Sam dropped down too the floor too quickly, almost banging up his knees. He looked up at Dean as he rubbed his cock like he was told to.
“Dean,” Sam moaned.
Dean laughed. “You're such an easy slut, Sam. Do you think you cum just from me calling you names? I bet you could.”
Sam shivered. He wanted that bad. He could imagine Dean tying him up, not even touching him, just talking to him until he came.
Dean slid his own cock out from his jeans. He spit into his hand and stroked himself, looking down at Sam like he was a million miles tall.
“You don't get my cock yet. You've gotta learn to be a good bitch first. Then I'll let you taste it. First, you're gonna be my cum rag and clean up my mess.” Dean pumped his cock harder. Sam thought he was going to cum on his face, but instead he watched as Dean groaned and painted the floor with his cum.
“There you go, baby. Clean it up.”
Sam licked his lips. He bent over, still playing with his cock, and put his tongue to the floor. He scooped up a mouthful of Dean's cum and moaned as he swallowed it down. With his hand on his cock and his tongue on the floor, Sam came, moaning, falling face first into the puddle of cum.
Sam caught his breath and licked his lips. He still had to finish what he started. He made himself busy, cleaning up the floor with his tongue, his hair was filthy with it. Finally, when he couldn't taste anymore of his brother's seed he stopped and looked up at Dean.
Dean smiled at him. “That's my cum rag.” He held out his hand and let Sam lick the cum from his fingers. “Good boy, Sammy.”