Dean didn't normally spend so much time down in the 'muck' of Hell; where the filthiest deeds of Hell took place.

Nah, that was a total lie.

He was always down there, checking on Cas, talking to Cas and giving the guy some company. There really wasn't any other reason for him to be down there. He didn't have a 'job' anymore like his blue eyed friend. He'd outgrown that. As a higher-ranking demon he mostly worked freelance. They called on him when they needed him, otherwise he could just run around and cause general chaos for all they cared.

And sure, he did that. Over the decades he'd spent in Hell though, that'd gotten pretty fucking old.

… 'Scuse the french.

So Cas was a nice change to all of that, someone who could actually hold his attention. The only demon Dean actively sought out when he had free time.
He didn't know why exactly he was so… drawn to the bloke. Sure, he was one of the few demons that had a soul in such good shape. Dean could still see the 'bluest blue' in his gaze, and only rarely did his eyes flicker to black. His skin, whilst ravaged from his years spent on the rack, still showed his (in Dean's words) pretty damn-fine looking form. A runner's form, if Dean's memory served.

Which, nowadays, it kinda didn't.

Anywho, Besides Cas' physical appeal, the guy was a breath of fresh air. He didn't think like other demons. It hadn't taken long to notice.

Cas didn't appear to be ruled by baser urges- urges to maim and trick and deceive. He wasn't all that vicious either.

Dean knew from experience that Cas could be pretty freaking scary when he wanted to be, but most of the time he was more like a kitten. An adorable, rain soaked kitten who had squinty, beautiful eyes.

[Cas would probably kill Dean if he heard him think that.]

All of this came together to explain why, after just finishing saving a crossroad demon's ass (God dammit Steve), he was making his way down the oh-so-aptly dubbed 'Hallway of screams.'

… He may have came up with that name himself.

It wasn't hard to find Cas, the guy stood out like a sore thumb. Still in his Earthly clothes and with a full patch of hair (Dean was jealous of his floofy black mess. Who could blame him? Given his own follicle impairment.)

After their chat earlier, Dean had been thinking. He had never really considered the whole surface vs damnation debacle. Hell had become his home after time, and he'd long since forgotten what Earth was really like. Only his few-and-far-between trips up above gave him some perspective. Each time had been for a job though. He could visit anytime he wanted, but what was the point?

Since Cas had brought it up, Dean had put some thought into the question.

"Hey Cas," he greeted, bony hands lifting to ruffle Cas' hair.

The demon ducked his head to free himself, but Dean didn't miss the exasperated/amused wombo-combo on his face. "Hello dean."

"Did ya' miss me, honey-buns?"

Castiel read something on his clipboard before responding. "If I say yes, will you leave me alone?"

"Aww, don't be like that Cas." Dean circled him, pressing into the man's personal space. "I know you absolutely love my company."

"Keep thinking that," Cas responded blandly, not giving anything away.

Dean chuckled. "You're so cute when you're being stubborn."

"What brings you down to the racks this time?" Dean didn't miss how he changed the topic.

That was another thing about Cas that kept Dean coming back. He could never really get a read on the guy. He knew Cas had to at least kind of enjoy his company. Otherwise he would've been told to shove off by now.

"Same old, same old. It was getting too boring hanging around and waiting for orders. Thought I'd come bug my favorite pencil-pusher."

Castiel directed a deadpan expression in his direction. "How considerate."

Dean couldn't hold back the giant grin that broke out across his face. "I know right? I might be the nicest demon in this place."

Cas looked at him as though he might be crazy.

The sad truth was that he was. Pretty much every demon in Hell was at least some percentage of coo-coo.

"Whatever you say." Cas turned and started talking to a waiting demon, instructing him on which rack he'd be working.

Dean waited.

"So how's your day been?" Dean asked when Cas was done.

"Quiet," Cas answered. The double-meaning of that statement did not allude the older demon. "How about you?"

Dean wondered, for perhaps the millionth time, if he should open up to Cas. Tell his demon pal that he was so over doing all the dirty work for the pompous assholes that ruled over them. Sure, he always got some sick satisfaction from torturing some schmucks or roughing up some misbehaving demons, but the truth was–

"…Same old same old."

Dean had always hated talking about feelings.

If Cas picked up on Dean's hesitation, he didn't show it. It was probably better that way.