"You are gorgeous, Dean," Crowley mused, running a hand over the hunter's bare chest. They had been on there way to grab a demon who worked for the horsemen, but when Crowley mentioned that they had time to make a pit-stop, Dean didn't give it much thought before finding the nearest hotel.

Dean rolled his eyes. "Thanks, I guess." He rested his hand on Crowley's arm, absentmindedly rubbing his thumb along his skin. "Can I ask you something?" he asked after a minute.

Crowley raised an eyebrow. "Depends on what it is."

"When we made our deal… why did you ask for this?"

"As I said, you selling your soul would have been counterproductive. I needed your focus on fighting Lucifer, not on finding a way out of our deal, like you attempted with Lilith. And I also knew that I would become a target, so I needed you to protect me. And the only way to ensure that was for you to be under my control. As for the sex… so long as you belong to me, I intend to have fun with it. Can you really blame me?"

Dean chuckled. "I guess not."

"Really?" Crowley asked with interest.

"Shut up."

"I told you you'd like this deal."

"Yeah, well, don't tell me you're not enjoying this more than you thought you would."

"Oh, I'm not denying anything. You are amazing, Dean. This is the best deal I've ever made." He brushed a hand against Dean's cheek, prompting him to look up so that he could press his lips against his. Dean returned the kiss deeply, rolling over so that he was straddling the demon.

It was several minutes before Dean broke the kiss, his hands pausing their exploration of Crowley's sides. "How much time do we have?" he asked breathlessly.

Crowley glanced at the clock. "Less than I would like. We should get going."

Dean sighed as he got to his feet, looking around for wherever his clothes had ended up. Crowley sat up on the bed, watching the hunter thoughtfully. "Is it just me, or are you disappointed that we don't have more time together?"

Dean didn't look at him as he pulled on his boxers. "Like you don't already know the answer to that."

"Maybe I want to hear you say it."

Dean didn't respond as he searched the area around the bed, finally looking at Crowley when he came up empty handed. "What the hell did you do with my pants?"

"You took your own pants off, darling. I think you tossed them somewhere in that direction." He motioned vaguely toward the door.

"Oh… right," Dean muttered sheepishly as he moved to look where Crowley had indicated. He located his pants and pulled them on, then found his shirt thrown carelessly over a chair. Once he got everything on, he turned around to see Crowley standing right behind him, already fully dressed.

"Dean, I would like an answer," he said softly.

"You don't always get what you want." Dean started to turn away, but Crowley caught his arm.

"It's a simple question."

"But that's not what you're really asking. You don't want to know if I'm disappointed about not having time for another round, you know that I am. No, you want to know if it's more than that, and I don't have an answer for you, Crowley. Now, you said that we have to go, so let's go."

Crowley, for once, was speechless as he looked at Dean, and Dean looked determinedly back at him. After a few seconds, the demon sighed and released Dean's arm. "You're right." He motioned toward the door. "After you."

It was thanks to Crowley that they were able to take out Pestilence the next day. He got the horseman's location from the demon, Brady, and then proceeded to save them all from a hell hound. Sam may not want to admit it, but Dean knew that they wouldn't have been able to do it without him.

Now all that they were left with was Death, and then Lucifer, himself. Dean wasn't going to say it aloud, but he wasn't all that confident in their chances, especially with the potential spread of the Croatoan virus that Sam, Cas, and Bobby were left to stop. Of course, they had the easy job – Crowley had chosen to partner with him again to take on the task of killing Death to collect the final horseman's ring. At least Crowley had just happened to have the one thing that could kill Death, but Dean still had to get close enough to him to use it.

"Is there any chance that we're going to succeed here?" he muttered as they drove into Chicago.

"You are horribly pessimistic, squirrel," Crowley sighed.

"Well, we're about to take on Death, what am I supposed to think?" Dean snapped.

"You have his scythe; you can kill him."

"Yeah, but he's freakin' Death."

"And you're Dean Winchester."

He rolled his eyes, not reassured by that in the slightest. "You've got an awful lot of faith in me."

"I know what you're capable of; it's why I bought you."

"Oh, great. Way to make me feel like a piece of property."

"Well…" A small smirk tugged at the demon's lips.

"Let me guess, I'm your property." He shook his head, but his lips were pulling up into a slightly amused smile. "Should I get a 'Property of Crowley' tramp stamp?"

Crowley chuckled. "Would you, if I asked?"

"Hell no," Dean scoffed.

"I thought not," he sighed. "I could make you, of course."

"But you won't."

"You're confident."

"And you're going soft."

Crowley shifted in his seat, looking at the hunter with raised eyebrows. "That's a bold claim, Winchester."

Dean shrugged. "When's the last time you actually used our deal to make me do something I didn't want to?"

"Well, I haven't had to, have I?"

"Oh, there've been a few times that I've said no and you didn't push it."

"Then clearly those things weren't that important to me."

"Hmm…" Dean hummed thoughtfully. "Or I'm growing on you."

Crowley scoffed, crossing his arms as he turned to look out the window.

Dean smirked triumphantly. "Does the King of the Crossroads have a soft spot for a hunter?"

Crowley was silent for a few seconds, and Dean caught the reflection of his glare in the side window. "I believe that we should be focusing on Death, should we not?"

Dean chuckled. "Sure thing, sweetheart. Tell me where I'm going." Well, at least that was one battle that he could win today… more or less.

But as it turned out, it wasn't the only one. Taking on Death turned out to be not near as big of a deal as Dean had expected it to be. Death wanted Dean to stop Lucifer and simply handed over his ring. Of course, there was always a price.

"I can't do it."

"Dean, you promised Death, you can't go back on that."

Crowley had come to visit him at Bobby's that night; they were sitting out in the junkyard, on the hood of a broken-down car, sharing a bottle of Scotch.

Dean shook his head, looking hopelessly down at his half-empty glass. "This whole mess… all I've ever wanted is to protect Sam, and now I'm supposed to just let him die?"

"I'm sorry," Crowley's voice was soft, almost sincere. "But Death is right. I don't know how else we're supposed to get Lucifer to just step into the cage unless Sam is the one pulling the strings."

"And you think he can just overpower Satan?" He looked up at Crowley uncertainly.

"One thing I've learned is to never underestimate you boys. I don't know how much your brother is capable of, but if I were the devil, I'd be worried."

Dean nodded thoughtfully as he finished off his glass. "So what am I supposed to do?"

Crowley snapped his fingers and the empty glasses disappeared. "Let him make his own decision. He's a big boy."

"He'll want to do it."

"I know."

Dean sighed. "Everyone keeps telling me the same thing, and I'm suddenly feeling like I don't have much of a choice." And there really was only one choice – he knew that, as much as he didn't want to admit it. He jumped off the hood of the car and turned to Crowley. "Well, Crowley, it was nice knowing you. See you at the end of the world, or in Hell, whatever comes first."

Crowley slid off the hood of the car, resting his hands on Dean's waist. "If you die, someone will have Hell to pay. Look out of yourself, okay?"

"What? The insurance policy you took out on me expire, or something?"

"Shut up." Crowley's eyes were blazing with intensity as they looked up into Dean's. "You were right. I see now how I made a mistake in getting close to you, but it's too late to do anything about that. I just need you to make it out alive tomorrow. Whatever the cost."

Dean licked his lips as he leaned down, resting his forehead against Crowley's. "Crowley, I…"

"Don't say it," he demanded sharply.

"What?"

"Don't say those words because you think it'll be the last time you have to tell me. I will not be left with that in my memory of you. I'd much rather pretend you hate me because that I can live with. Not whatever this is."

"So if I do make it back?"

"We'll cross that bridge when we get to it. And I do mean when, because you are coming back."

Dean nodded, breathing in a deep breath. "Stay out of harm's way until this is all over."

"I will."

Dean pressed his lips to Crowley's before stepping back. They stayed looked at each other for just a moment longer before Crowley gave him a small smile and then disappeared with a snap of his fingers.