Ok, so this is my very first Dean/Crowley. I had planned to write my usually Sam/Dean but lately I've fallen absolutely in love with Crowley and he kept popping into my head so I finally gave in and here it is. I don't know if it's any good or if I've done Crowley justice but I tried. Enjoy!

Disclaimer: Nothing belongs to me except the plot.

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Dean stared glumly at the beer he had no desire to drink and tried to make sense of the monumental mess they were all in. It wasn't often he allowed himself time to think because when he did he was swallowed by a overwhelming sense of hopelessness. He wasn't trained for this, he wasn't sane enough to shoulder the weight of the entire world on his shoulders.

Tearing his attention away from his beer he stared at the Horseman rings. The fate of humanity comes down to four pieces of jewellery. Although Dean didn't really have to worry about the apocalypse because when Death found he had lied right to his face, he was screwed for all eternity anyway. He just couldn't do it. Almost thirty years of Sam being his responsibility, and he was expected to just let Sam say yes to the Devil?

"Why so glum cupcake?"

Dean didn't bother looking up to see who it was, the gruff British drawl was impossible to mistake. He was grateful for Crowley's company, something which made him rather uncomfortable. Normally just being around a demon made the bile rise in his throat and his fingers itch for the Colt, but not when it came to Crowley. He liked Crowley's sense of humour. The first time Crowley had called Sam moose he nearly choked on his own tongue in an effort to stop the laughter that was desperately trying to escape.

"What do you think Death does to people who lie to him?"

"Nothing pleasant."

Dean glanced up to see Crowley leaning against the door to the garage holding a bottle of whisky and two glasses.

"Although, I wouldn't really know. I don't think anyone has ever been that stupid before." Crowley continued before pushing himself off the door frame and sitting across from Dean.

Dean was amazed at the level of cockiness an self importance Crowley was capable of putting into a single movement. And he was even more amazed that it didn't irritate him as much as it would if it was anyone else.

"I'm guessing your question isn't hypothetical?" Crowley asked, opening the bottle of amber liquid and pouring two glasses before sliding one over to Dean.

Dean swallowed half the liquid quickly, needing the soothing warmth that came with it. Looking at Crowley he hesitated. Was he really going to have a heart to heart with the demon?

"I promised Death I'd let Sam say yes to Lucifer." Dean admitted, swirling the whisky in his glass absently .

Crowley rolled his eyes and took a small sip of his own drink before answering. "Has it ever occurred to you, that it isn't up to you to let Sam do anything."

"What?"

"Your brother is an over grown moose of a man with breath taking anger management issues. He's big enough and ugly enough to make his own decisions."

"I know that. Fuck. I know. I just…..I raised him Crowley. After mum died, dad crawled into a bottle and I was left to take care of Sam. I was four years old, couldn't even tie my own shoe laces but I was responsible for the life of my little brother. I know he's a grown man, but to me? To me he's still the same four year old boy who wants to sleep in my bed because he's scared of the monster in his closet." Dean couldn't stop himself when it all started pouring out. He'd never told anyone this and it felt really good to finally unload.

There was a long silence as they both tried to understand the strange air of familiarity and intimacy Dean's confusion had generated. Dean was confused by how easy it was to tell Crowley such personal things and how he could feel so at ease and relaxed in the demon's presence.

Crowley was busy struggling to identify the strange stirring of emotions he hadn't felt for over two hundred years. Empathy maybe? No empathy was different, he didn't understand why Dean would feel the way he did. Sympathy perhaps?

"What are you doing here anyway?" Dean broke the silence eventually. "You usually piss off when your part is over."

Crowley snorted and poured himself another drink and asking silently if Dean wanted another. When Dean nodded he poured the drink without a word. It was only after taking a sip and savouring the taste did he speak.

"Where else am I supposed to go? My house is burnt to the ground, I can't go back to Hell anytime soon, and I'm on Lucifer's most wanted list underneath you, Moose and Angel cakes." Crowley admitted but there wasn't a hint of self pity in his voice and Dean knew why. Crowley was used to being alone, he was a survivor, adapting to any situation effortlessly.

"Give me your phone."

"And why would I do that?" Crowley asked, raising his eyebrow in a way that was both curious and condescending.

Dean pulled his own face and held out his hand. Crowley smirked and pulled the black iphone out of his jacket pocket and holding it out. Dean went to grab it but he pulled it away just out of reach. "Let me see the rings and I'll give you the phone."

Dean realised the rings were still held tightly in his left hand. Once again he had to ask himself whether or not he trusted Crowley with the rings. Sighing softly he slid them over the table towards Crowley but not without a cocky retort. "Is everything a deal to you?"

"I'm King of the crossroads for a reason darling." Crowley answered with a cocky smirk before placing the phone in Dean's hand with a quiet slap.

Dean rolled his eyes and leaned back in his chair. Glancing up he watched Crowley examine the rings curiously, a intent look on his face. Dean slid the bar across to unlock and swear when he realised he had no idea what Crowley's password was.

"What's your password?"

"That wasn't part of the deal."

"Crowley." Dean growled and was rewarded with a small smile. Not a smirk but a genuine smile.

"Sixteen sixty-one."

Crowley was telling the truth.

"You know Crowley, I like you. I don't trust you, but I do like you." Dean admitted as he created a new contact and tapped in his personal number. "So if you ever need anything, give me a call."

Dean had a feeling he was going to regret his actions sometime in the future but chances were he wouldn't survive that long so he handed Crowley back his phone without hesitation.

"What could I possibly need your help for lumberjack?" Crowley snarked but there was no heat behind it and he slid the phone back into his jacket pocket.

"What is he doing here?" Sam asked nastily, spotting Crowley as he entered the garage from the house, large body creating a shadow over the two.

"And that's my cue to leave." Crowley answered, chucking Dean the rings and disappearing.

Dean caught them and sighed inwardly when he saw the look of scandal on Sam's face.

"You gave him the rings?" Sam asked incredulous.

"I let him hold them for five minutes!" Dean shot back.

"Dean! How stupid can you be? What if he had taken off with them?"

"Sam in case you've forgotten he's the only reason we have them all!" Dean yelled back.

Sam frowned and then his face went lack, eyes widening in shock. "You trust him. You actually trust him."

"No I don't." Dean denied.

He didn't trust Crowley.

He didn't.

He couldn't.

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Alright, so there it is. There will be more coming and I know it's short but I wanted to see if it was any good and people liked it. Hope you enjoyed it and please review.