What the hell had happened to him? He was the King of Hell, he wasn't supposed to feel anything for anyone other than himself. Survival and pleasure, those were the only two things that mattered. So how did Dean Winchester play into that? It was supposed to be survival – keep your enemies closer, and that was all there was to it. But now… well, he was getting ahead of himself. It was best to start at the beginning.
When most people look at someone who does horrible things, say get drunk and beat his son, they put all the blame on that person and never think of what led them to that place. Fergus MacLeod, as had been his name at the time, had been repeatedly told by his mother how worthless he was, until he was eight years old and she ran off. Many men tried to fill gaps left by horrible mothers by flinging themselves at women, and Fergus was no different. And then he had met her. He thought he had found 'the one' until she also ran off, leaving just a note and their newborn son. So yes, he had become more bitter and had taken it out on the son that served to remind him of what he had lost.
It was a few years later that he did something really stupid. He still went out looking for women, but none were interested now that he was out of his prime and had a son. So one night when he was particularly drunk, he remembered something his mother had told him about demons and crossroads deals, and he decided to give it a shot. Truth be told, with all that he had done, he didn't believe that he had a soul anymore, so he didn't think it would hurt. Also, he had heard that crossroads demons were normally attractive women, and he was hoping to seal the deal with more than just a kiss. The demon had been reluctant on that point at first, but he had always been persistent and good at negotiating. He got what he wanted.
So he had sold his soul for a few extra inches, and ten years later, the hell hounds came for him and drug him to Hell. He thought he had known pain in his life, but it was nothing compared to the torture he received in Hell. Not everyone received the same treatment in Hell – the demons knew that Fergus would jump at the chance to be the torturer rather than the torturee, and they didn't need him, so he spent 20 years on the rack before the offer was made. When he did finally pick up the knife, it was clear that he was a natural, and he overheard some talk that the offer should have been made sooner.
He tortured in Hell for 50 years before he was approached by Lilith. She claimed that, while he was a gifted torturer, she could see that it was not where his heart was. She said that it had been clear when he had made his deal that he had some skill in the area, and she offered him a job as a crossroads demon. He gladly accepted, taking on the name of Crowley as he started his new life. He stayed close to Lilith, though, knowing that in Hell, just as everywhere else, it was all about who you knew. The two of them grew close and when Crowley rose to the position of King of the Crossroads and her second-in-command, he knew that he had made the right choice.
That was when things started getting complicated. Crowley seemed to be the only demon with a mind of his own, and so when Lilith started on the task of breaking the 66 seals to free Lucifer, Crowley knew that it was a bad idea. He had no real since of loyalty to her, but he also knew that if he opposed her, he would be killed. It put him in a tight spot, and it seemed that the only thing he could do was hope that these infamous Winchesters would put a stop to her. After all, they had thrown some kinks in Azazel's plans, so perhaps they were better than the average hunter.
That wasn't to say that Crowley wasn't doing anything, though. No, he was working on a contingency plan in case the Winchesters did fail. He only knew of one thing that might kill Lucifer, should he be freed, and Lilith had just arranged for it to be brought to her so that it could be destroyed. So Crowley intercepted the delivery – pity the poor girl didn't get out of her deal, but he did have himself to think about – and he stored the colt away for safe keeping.
Of course, the day did come when Lucifer was freed and then Crowley knew that he had to get the colt back to the Winchesters. A few whispers in the right ears brought them right into his parlor, where he finally got to meet the two of them face-to-face.
There was something to be said about expectations not living up to reality. These two were the best hunters the world had ever seen? Seriously? Tall, gangly sasquatch paired up with I'm-trying-to-make-you-think-I'm-tougher-than-I-am pretty-boy. He had his misgivings about sending them off to kill Satan, but their track record was impressive, so perhaps you really couldn't judge a book by its cover.
When he heard how it had all gone down, he was mostly irritated that Samuel Colt hadn't left a list of creatures his gun couldn't kill. So there was that plan out the window. He decided that it would be best to hide in the shadows until he heard anything more from the Winchesters, glad that he had thought to plant that tracking device in their car. Eventually he heard of the plan – of course, if any angel was going to pull through for them, it would be Gabriel. Crowley hated all angels on principle, but he did have a soft spot for the supposed trickster, and he certainly knew him well enough to strongly doubt that he was really dead.
He thought it best to wait a few days before approaching the Winchesters again, and when he did, he was greeted by Sam attempting to stab him. After a few well-chosen words, he calmed them both down and got them to agree to work with him. Of course, then came the hard part of getting the pretty-boy without the sasquatch.
He was admittedly a bit surprised when Dean agreed to his terms without any fuss. Clearly he did have some brains in there somewhere. And oddly enough, he actually enjoyed working with Dean. So much so that the next time he teamed up with them, he arranged it so that he and Dean went off together again.
He was curious about the elder Winchester – there was more to him that met the eye, and he wanted to find out what it was. Of course, then things got… complicated. They were a demon and a hunter, after all, and they had very different goals, especially after he became King of Hell.
Half the reason Crowley had gone to Castiel for his Purgatory plan was so that he could work with Dean again. But the angel just had to kick up a fuss about his favorite hunter being involved, and then when Dean did figure out what was going on, he made it his aim to stop it. And naturally, whatever Dean set his mind to, he achieved, so that plan tanked. Well, it worse than tanked, it let out the leviathans. Though, Crowley had little doubt that Dean and Sam would be able to take care of them, and he was perfectly willing to lend a hand when the time came to do so.
Unfortunately, that whole ordeal ended with Dean being sent to Purgatory. And of course, being the King of Hell, he had to pretend that it was a good thing. One of the most deadly hunters gone from this plane of existence, and the other giving up hunting because of it. But the fact was, Crowley missed him. He even missed Sam in some ways, though that was more for amusement's sake. Yes, he had grown attached to Dean, and that was a very dangerous thing to do.
It proved just how dangerous when Dean found his way back from Purgatory, as he always seemed to be able to do. And then he and gigantor decided to set to closing the gates of Hell and locking all demons inside. He should kill them both – he certainly had the capability to. And yet, he didn't, not even when they only had one trial left. Admittedly, he did start killing the people they had saved, but he couldn't bring himself to hurt them.
He knew that it would all come back to bite him in the ass, and he was right. He thought he finally had them where he wanted them, and it turned out it was all a trap. And then he was locked in a church with Sam for hours, the hunter pumping him full of human blood in an attempt to cure him.
He could say this, at least, it was certainly a time for self-reflection. He could feel himself becoming more and more human, craving human things like love, and the more time that passed, the more he thought about Dean. Dean would always hate him, he hated all demons, and he would always group him in with all the rest. He would never give him a chance, and maybe he didn't deserve one. But surely everyone deserved at least that, right? Didn't everyone deserve love? Didn't he? Maybe becoming human wouldn't be such a bad thing. Maybe he'd then be able to tell Dean how he felt about him. Maybe Dean would return his feelings.
But Dean stopped Sam before he could finish the trial, leaving Crowley still a demon, but broken almost beyond recognition. And then they locked him in their dungeon to suffer in solitary, still haunted by the thoughts he had had when he was almost human. He couldn't deny anything now. He had feelings for Dean, and more than anything, he wanted Dean to feel the same about him, even though that was impossible.
Just as bad, he was now craving more human blood. He was able to steal some here and there, but of course the boys noticed. But he needed it – this feeling – and maybe then Dean might see that he was different from other demons.
The chance for his escape finally came when Dean needed his help saving Sam from the angel that was using him as a vessel. He had to possess Sam to warn him about the Gadreel, and then get out before the angel found him. He told Dean that if Gadreel found him, he'd run, but he didn't. He had to save Sam for Dean, so when Gadreel did find him, he fought, and he didn't leave until the angel was gone.
Dean immediately rushed over to Sam and Crowley was free to go, but he didn't. He didn't want to leave yet, and when Abaddon and her demons pulled up outside, surely after him, he knew what he had to do. He told Sam, Dean, and Castiel to leave – he would hold her off while they got out. Dean insisted that it didn't change anything, but he knew that he had to be grateful. He managed to talk his way out of his confrontation with Abaddon and started forming a plan with two goals – kill Abaddon and get Dean.
Contrary to what he had threatened, Dean didn't kill Crowley when he next turned up. And after a few well-chosen words, he even agreed to work with him. After their little adventure, though, Crowley found himself analyzing it, wondering if he was doing the right thing here. What the hell was wrong with him? He was like a teenage girl!
That was when his addiction got worse. If he took enough human blood, he found that he was able to get drunk. He still longed for Dean, but a part of him realized that he could never have him. He was using him, after all, and he had figured it out. What had he been thinking? How was he supposed to win someone over by using them?
He didn't answer Dean's calls, even though he called a lot. When he got drunk enough, he would leave voicemails for Dean, but it was probably a good thing that they were mostly incomprehensible. When he finally realized how far he'd fallen, it was too late. He had been betrayed, and now Abaddon probably knew everything. There was only one thing he could do, even though he really didn't want to.
He called Dean, telling him that he needed help. Of course, he brought Sam with him, and their solution was to lock him in their dungeon again until he was sober. It was effective, he'd give them that. By the time they found the First Blade, he was finally thinking clearly again. Yes, he had a thing for Dean. Yes, he needed him to kill Abaddon. No, that was not worth getting himself killed over. So he took the blade and gave the boys the task of finding Abaddon.
Not that that meant that he was staying away from Dean, though. He could still have some fun, he just had to be smart about it. Not to mention, there was something he had to figure out – did Dean at least care for him a little bit? He knew he didn't on the same level that he cared about Dean, but he thought there might be at least a little something there.
So he set up a test and was quite happy when Dean saved his life, proving him right. And now if the rumors were true… well, they were definitely going places.
And sure enough, the rumors were true. He could see it when Dean killed Abaddon – the mark was definitely getting to him. And then when Sam got scared and locked him up, it was Crowley he turned to to get him out. That was the same day he died.
Yes, the news hurt to hear, but he pushed that pain aside, thinking of the bigger picture. He appeared in Dean's bedroom, and his suspicions were confirmed. Dean was now a demon.
He thought that that would get him what he wanted, but he had been wrong. Dean as a demon was ruthless, uncontrollable. There was no way that he was ever going to care about him, and he was ruining business. So he handed him off to Sam, who was able to cure him and make him human again.
That was when his problems reached a new level. His mother, of all people, showed up, and being a fool, he let her into his life. She was adamant that he should stop working with the Winchesters, and while he did take her advice in some areas, he wasn't about to take it there, not even when Dean lied to him and stole the First Blade back from him. Well, then she decided to take matters into her own hands and attempted to kill Dean.
He went to talk to Dean after that, and his advice put everything in perspective. So he kicked Rowena out and went back to doing things his way. Of course, that made an enemy for him. And when she was able to help someone who hovered on the line between enemy and ally, then that made two. Which was what had gotten them here.
It wasn't hard to piece together what had happened. Rowena had probably promised Sam that she could remove the Mark of Cain from Dean, if in exchange, he would kill Crowley. Of course Sam would agree to that. Only it hadn't gone as planned.
Dean had found out. Sam had summed Crowley to the bunker and had been about to kill him, when Dean jumped in front of him. So now Crowley was kneeling on the floor, Dean's lifeless body in his arms, while Sam slowly sank to his knees in front of him.
"This wasn't supposed to happen," he breathed, the weapon clattering to the floor. It was a weapon designed by a powerful witch to kill the King of Hell; there was no way that Dean, no longer possessing the Mark of Cain, stood a chance against it.
"I should hope not," Crowley snapped, glaring up at him. Accident or not, this was his fault.
"Why would he…?"
"I don't know." Crowley knew that Dean cared for him a bit, but just a bit. And now he had gone and died for him. It didn't make any sense.
"Can you bring him back?"
Crowley wanted to point out that Sam was asking for help from the guy he had just tried to kill, but even more so, he wanted Dean back, so he wasn't going to put up a fight. "Yes, but I can't do it without-"
"My soul. Fine. Take it."
"You two and your self-sacrifice," he sighed, shaking his head. "Well then, you know the drill."
Sam grimaced as he leaned in and Crowley reached out a hand, grabbing the collar of his shirt to pull him in the rest of the way until their lips met. Ugh. This was definitely not the Winchester he wanted to be kissing.
"What the fuck?!"
Crowley and Sam jerked apart, looking down at Dean, who was hastily pushing himself to his feet. Crowley and Sam followed suit and stood as well. "Sam, what the hell? First, you're trying to kill Crowley, and now you're selling your soul to him?"
"I had to-"
"Bullshit. You didn't have to do anything. I told you to drop it with the Mark of Cain, to burn the Book of the Damned, but instead you turn to Rowena?"
"Well, the mark's gone, isn't it?"
"Yeah, but at what cost? Rowena has the book, and regardless, it's not worth Crowley's life. He's been helping us! And then you go and sell your soul-"
"Relax, Dean," Crowley spoke up, before turning his attention back to Sam. "You're released from your contract."
"What?" Sam asked, his eyes wide.
"I didn't intend to hold you to it. I just needed the exchange to bring him back."
"Um… thanks."
"I would just appreciate it if you don't try to kill me again."
Sam hesitated just a second. "I won't."
"Good," Dean said. "Now we just have to worry about stopping Rowena before she comes after all of us."
"With those books, that'll be nearly impossible," Crowley pointed out.
"She doesn't actually have the books," Sam said. "She just used them to find a cure for Dean. I wasn't going to let her have them."
"She'll still have memorized a few things, though"
"But it's at least better than her having them," Dean admitted.
"We could use your angel."
Sam nodded. "I'll call him."
"While he's doing that…" Dean turned to Crowley. "Crowley, can I have a word with you privately?"
"Of course." Crowley felt Sam's eyes on them as they walked out of the room, but his mind was elsewhere. He was actually feeling nervous, which was something he rarely felt. Great, he was back to feeling like a teenage girl again. How did Dean have this effect on him?
He followed Dean into his bedroom, vividly recalling the last time he had been in here. The whole Mark of Cain ordeal had been one big mistake.
Dean closed the door behind them, then turned to face him. "Thank you. I know you didn't have to release Sam from his contract, especially after he nearly killed you. So, thanks."
Crowley shrugged. "Don't mention it."
"Why'd you do it?"
"Because I didn't need a price to bring you back. You saved my life… died for me…. I just don't understand why."
"Because I didn't want you to die."
"That's new."
"Not as new as you think."
They stood in silence for a few minutes before Crowley broke it. "If I had known that all of this would happen, I would have never had you get the mark."
"I know. But I needed it to kill Abaddon. There was no way to know that all of this would come from it. For what it's worth, if I had known all this would happen, I would never have tried to close the gates of Hell. That's where this all really started. Abaddon would have never even been a problem if it weren't for the things we did then."
"We've all messed up."
Dean nodded. "Maybe I'm still messing up," he mused.
Crowley arched an eyebrow. "In what way?"
Dean hesitated. "You."
Crowley wasn't always sure that he had a heart, but right then he felt it drop. "Yeah, you probably shouldn't have saved me. I am a demon, after all."
"I'd do it again, though." He made eye-contact with him and Crowley felt his breath catch.
"Well, I'm definitely still messing up," he muttered, more to himself.
"How-?"
Before Dean could finish his question, Crowley closed the space between them and wrapped a hand around the back of Dean's head to pull him down into a kiss. Honestly, he had expected Dean to pull away. He expected him to shout at him and for this to be the end for them. But after a moment of being frozen in shock, Dean's arm wound around Crowley's waist, pulling him closer as he returned the kiss. Crowley had never been so happy to be wrong.