"Hello, boys." Crowley reiterated his infamous catchphrase as Squirrel entered the torture room, closely followed by his angel boyfriend. Both looked sincere as they glared at the King of Hell shackled to the chair that he's been sat in for so long that it had practically become part of him. Then again, the dozy duo was generally serious, what with everything they've been through. Fools, Crowley thought to himself. Letting it get to them. They're so… human.
"Tell us what the deal was." Dean interrupted his thought process, strolling ominously towards the demon.
"I don't follow." Crowley retorted.
"Don't pretend you don't know. You made a deal with him, or one of your cronies did, and now you're going to pay." Dean continued, clearly getting angrier by the second.
"I have no idea what you're talking about." Crowley remained nonchalant.
Dean grabbed Crowley's front, one hand hovering over him, threatening a punch. "Listen here, you son of a b-"
"Easy, there, Squirrel. Put me down and we can talk this through." Crowley was slightly concerned now, though he didn't show it. Dean breathed deeply, a furious expression on his face. He showed no signs of letting up.
"Dean…" Castiel chipped in, warning his boyfriend to ease off a bit. Dean glanced over at the angel then sighed, dropping Crowley back into his seat, looking more dishevelled than previously.
"What's happened, exactly?" Crowley inquired innocently. The low growl of a hellhound emanated from outside, and suddenly he knew what had occurred.
"Kevin is dead." Castiel said bluntly in his monotonous voice. The harsh words impacted him like a series of punches. A cocktail of conflicting emotions surged through Crowley in the brief aftermath of the statement. Shock, suspicion, denial. And that was barely a fraction of the full amount. But then, a sense of relief settled over the demon. At least the deal was complete now. He no longer had to worry about it. The pain surely didn't last long, though that was nothing compared to the torture the boy would endure in Hell for the rest of eternity. The thought of that caused a sinking feeling in Crowley's chest. The King of Hell knew the day of Kevin's demise was coming ten years before it actually happened. He'd had plenty of notice. Yet it still came as a shock.
"Oh. I'm sorry to hear that."
"Don't pretend you care. You tried to kill him. And caused his death." Castiel snapped. How dare that interfering angel judge him on such matters! He has absolutely no right to dictate the feelings of the King of Hell. And he didn't try to kill Kevin either – he was simply preparing him for the inevitable future ahead of the poor boy. Crowley realised he probably shouldn't let on that he was the one who made the deal, or he was dead for sure. Well, he'd be able to avoid it, but it would be cutting it a bit too close, especially as he was still trapped in chains.
It took every last bit of Crowley's willpower to not respond sarcastically (as was his natural speech pattern as a demon). He shouldn't come across as apathetic, however also couldn't seem too caring. It would make these mop-heads suspicious. Eventually, Crowley created an acceptable response.
"I told him this was gonna happen. I tried to warn him but the kid didn't believe me. I told him to run."
And the demon was eternally frustrated that Kevin didn't listen to him…