Work Header

Deal of the Century

Work Text:

Word spread quickly through the rank and file of demons that Dean Winchester was in Hell, enjoying the tender care of Alastair. Shortly after, orders came down that no demon was to make a deal with Sam Winchester, no matter how temptingly the younger Winchester begged.

Crowley sat in his chair, sipping a very fine brandy as he wagered with himself. Barely two hours before his deadline he got word one of his Crossroad demons was dead at the hands of Sam Winchester. Crowley briefly mourned her loss for she had been on of his top employees. That sweet deal she’d made with the elder Winchester had been talked about for some time after.

Two days later, Sam killed another Crossroads demon. Crowley raised an eyebrow at that. He’d assumed Sam would be satisfied with the death of the demon who brokered his brother’s deal. It seemed he had been wrong, something that didn’t sit well with him.

When the request came again from Sam, Crowley made a point to answer it himself. He wanted to see this boy who was off limits to his demons.

The boy was unkempt, hair stringy and oily, reeking of alcohol. A week’s worth of beard and the sallowness of his cheeks spoke of a man at the very end of his rope. Crowley tugged on his cuffs, straightening them as he studied Sam. Sam stared back at him with wild eyes, a knife held tightly in his hand.

“My, aren’t you a sight.”

Sam only glared at him. “I want Dean back. Now.”

“Really. I believe you’ve already been told that will not happen. We have him and we are not inclined to let him go. I’ve heard he screams so very well on the rack.”

Sam took a step forward, knife raised. Crowley vanished and reappeared behind Sam. Sam whirled around, staggering a little on his feet. .

“Now, Sam. You can kill all the demons you like but it won’t bring your brother back. You need someone higher up on the food chain to get him out.”

“And I suppose you’re that person.”

“I might be.” Crowley shifted closer to the human. “Just what will you do to get your brother back, Sam Winchester.”

“Anything.” Sam’s response was immediate, a glimmer of hope in his eyes.

Crowley smiled inwardly, feeling the first bite on his hook. He reached out to stroked a hand down Sam’s chest. Sam flinched but stood still.

“It could cost you your soul.”

“I want my brother back no matter the cost to me.”

Crowley slid his hand down Sam’s belly, holding Sam’s gaze. Sam stared back, quivering as the King of the Crossroad’s hand cupped him through his jeans. Sam hissed but didn’t pull away.

Instead, he lunged forward, kissing Crowley hard. Crowley hummed in pleasure, opening his mouth to taste grief, despair and a hint of insanity in Sam’s mouth. He squeezed gently, enjoying the feel of Sam’s cock in his hands.

Sam pulled back. “Do we have a deal?”

Crowley licked his lips, smirking at Sam. “Oh yes, we most certainly have a deal. However, it may take some time to fee Dean, even given my position.”

“Whatever it takes.” Sam said.

“Come to this address tomorrow. Make sure you clean up first.” Crowley held out a business card. Sam took it, the glimmer of hope spreading across his face now.

Crowley held back his laughter until he was home. He licked his lips again, capturing the taste of Sam from them. This had the potential to be one of his greatest deals. An unstructured deal with no terms set and no time line for delivery. Oh he was going to enjoy himself.

He wondered how soon he could get Sam in his bed on his hand and knees, that sweet ass of his on display for Crowley’s pleasure.

Dean Winchester would be set free from Hell in time. Crowley had been hearing the rumors for years of the plans from both Heaven and Hell. It was just a matter of time before the elder Winchester would be back on the Earthly plane. All Crowley had to do was string Sam along long enough for Dean to be freed and for Crowley to sink his hooks deeper into Sam until Sam was his. Bound to the King of the Crossroads.