This story was written for drewbug, who has been one of my favorite authors since the early 2000s. The request was: a Crowley and Castiel adventure that involves whump on both sides.

The story is planned out but not written yet. I expect to post a chapter every week or two, or sooner if my schedule/life permits.

Finally, I have this set as Dean/Cas, but it will be one-sided for a good while since Dean will be a demon for much of the duration. Also, Crowley's awkward season 10 crush on Dean but it will probably make an appearance too.

Enjoy, and please leave a review if you do!


Cas was trying to sleep. He'd cranked the heater before he climbed into bed, and pulled the thin motel blanket around himself, but it was still too cold in the room. A side effect of his failing grace, no doubt—along with the persistent headache, the tightness in his chest, and the way his joints ached every morning, it was as if a chill had settled somewhere deep in his bones and wouldn't leave him alone.

He picked his head up and glanced at the glowing numbers on the clock on the nightstand. 3:47. He dropped his head again to the pillow, pressing his face into it. Exhaustion was another thing that had been plaguing him for the last several months, but for some reason sleep didn't always come easy. Too many thoughts floated through his head: Dean was gone. Dean was alive. Dean was probably, if the lore he'd found meant anything, a demon.

Sighing, he turned over, so that he was staring up at the stained ceiling, wondering how the large vaguely butterfly-shaped blotch had gotten up there. Perhaps it was time to give up on sleeping for the night. Or perhaps—

He was startled from his thoughts by a three loud bangs on the door. A pause, then another bang-bang-bang. And another.

Cas swung his legs over the bed and pulled his robe around himself, tying it with a puzzled expression. Who would be here at this hour? Sam had made it pretty clear during their last encounter that he wanted nothing more to do with him, at least until his shoulder healed.

His heart leapt. Could it be Dean?

He padded across the chilly linoleum floor and rested a hand on the door handle just as it rattled again. Then he pressed his eye to the peephole, trying to simultaneously contain the hope bursting in his chest while also reminding himself that there was no point in getting his hopes up. It wouldn't be Dean. Of course it wouldn't.

It was Crowley. Somehow, the sinking feeling that accompanied that discovery was far stronger than it had any right to be.

Cas pulled the door open, puzzlement climbing up through the weight of disappointment. Crowley was standing impatiently, hugging one arm to his chest.

"What do you want?" Cas asked.

Crowley huffed, haughtily taking in Cas's bathrobe-clothed form, then pushing past him into the room and turning to face him. "I thought I was going to have to bash the door down. What took you?"

"I was…trying to sleep," Cas said, not sure why he was bothering to explain himself. Crowley, after all, had cut all contact after Dean's disappearance, and both Cas and Sam suspected that he had been involved. Sam had summoned him shortly before Dean had gone missing, after all. He sighed. "What are you doing here?"

Crowley waited a beat, as if for effect, then said in a very serious tone, "Dean is missing."

Cas squinted at him, unsure whether this was the demon's idea of a joke. "Yes. I know."

For a moment, Crowley's unflappable façade slipped, and Cas saw an emotion—fear, or regret?—slip across his face. Then the smug mask was back. "Not like you think, angel," he said. "Believe me."

"What does that mean?" Cas demanded, his patience (already frayed by the constant worry and physical decay) wearing thinner. That Crowley was hinting that he knew of Dean's whereabouts…or had known about them… it confirmed every suspicion that Cas had already had, and didn't make him any more sympathetic to whatever Crowley's plight was now.

But Crowley didn't answer immediately. Instead, holding his left arm close, he eased himself into the creaky chair that accompanied the motel room's tiny linoleum table. He gazed at Cas, and Cas returned the gaze.

Cas folded his arms and growled a threatening, "Crowley."

"I may have…been apprised…of Dean's whereabouts for some time now," Crowley said finally, squinting at Cas as if not sure how this news might be received.

"What?" Cas said, his heart beginning to pound faster again. He hadn't been this close to a lead in months, and yet now he felt frozen in place, anger burning somewhere deep within him. Crowley had known. All those months and Crowley had known.

"Now. Hold your horses," Crowley said quickly, no doubt sensing Cas's rising fury. "You've got every right to be upset, I understand. But hear me out. I've actually been…with Dean…uh, not in the Biblical sense of course…"

Somehow, Cas had crossed the distance between them without being aware of even deciding to move. He grabbed Crowley by the collar, hauled him up from the chair, and slammed him against the near wall, making him yowl. He tried to squirm away but his right arm appeared to be useless, and weak though he was, Cas was able to pin him in place against the wall with his forearm across the demon's neck. It took all the willpower he had not to pull back and smash his fist right into Crowley's gasping face.

"I can explain," Crowley was babbling. "Come on now. Cas. I wouldn't be here if it wasn't important."

Cas barely registered his plea.

"Dean has been with you," he snarled, shoving Crowley back against the wall again and making him yelp.

Crowley squirmed. "It was his decision not to contact you or the gigantor. Not mine."

"Crowley," Cas ground out. "Where is Dean?"

"I made him a demon," Crowley admitted after a moment.

Cas felt, for a moment, as if the world itself had tilted slightly on its axis. His worst fear—a fear he hadn't even found the strength to voice to Sam—had been true all along. Cas stumbled back suddenly, letting Crowley drop. His anger faded as a roaring sound filled his ears.

"He died," Crowley went on, adjusting his suit one-handedly. "I knew what would happen if I put the First Blade in his hands. So I gave it to him. I thought we could rule Hell together. Clean up the mess that my kidnapping and Abbadon's little civil war left behind. Unfortunately, that's not how things went."

"What do you mean?" Cas asked, folding his arms around himself. Dean was a demon. The thought spun through his mind, obliterating everything in its path. He thought off-handedly that if Crowley didn't have information he desperately needed, he might have thrown caution to the wind and smote him right there.

"Dean, er, didn't want to rule Hell," Crowley said awkwardly. "He wanted to drink, experience the local wildlife from every angle, believe me you don't want to know, and also to perform truly, truly horrible karaoke every night. I stayed with him, hoping he'd come around, but…not so much."

"Where is he now, Crowley?" Cas ground out, not sure what to make of Dean's demonic activities and deciding that he really didn't want to ponder them too much.

Crowley gave a deep sigh and blinked slowly. He looked…tired. "Hell wasn't nearly as stable as I'd hoped it would be, after the great white bitch turned half of my denizens against me. Apparently, they got tired of waiting for me to return from my 'vacation' to rule Hell, and decided to depose me. They tried to kill me, I escaped. But they took Dean. Now, we've got to get him back."

"We," Cas repeated incredulously. There was so much wrong with that presumption that he didn't know where to start. "Where did they take him, Crowley?"

"I don't know," Crowley shrugged a shoulder, wincing slightly. "Hell, I presume."

Cas squinted at him for several seconds. "Why did you come to me?"

"Isn't it obvious?" Crowley said.

"No," Cas said. The fact that he was still contemplating whether he had the energy to smite Crowley for turning Dean into a demon meant that, as far as allies went, he had to be fairly low on the list. "You don't have demons who could help you?"

"Not that I'm sure I can trust," Crowley said delicately, and Cas remembered vaguely that he'd been betrayed by a demon who had sided with Abbadon once before. "Of course, I don't trust you, either. But I assume that you'll want to find Dean. And I figured you'd be slightly less likely to kill me on sight than Moose. Anger issues, you see."

It was impossible, of course, to argue with any of that. But Cas was still confused. "You know that I won't let you take him back," Cas said. "If we find him. Sam and I will cure him."

Crowley waved a dismissive hand. "Cross that bridge, and so on. As long as Abbadon's supporters—don't even know who's riling them up, if you can believe it—don't have him and the First Blade, I'll be better off. So are you with me, or not?"

"I have to tell Sam," Cas said, taking a few steps toward the night table where his phone had been charging and reaching for it.

"Wait!" Crowley said.

Cas raised an eyebrow, hand still outstretched. "Why? Sam has been searching for Dean for months. As I have."

"Because he's not found, yet," Crowley said, as if it should be obvious. "And because if Moose gets word that I'm the one who took him from dead to demon, what do you think the chances are he won't try to kill me? Come on, now, we've been over this." When Cas hesitated, he added, "I can get Dean back, with your help. I can't do it if I'm bloody dead, or running from an overgrown Winchester."

Cas sighed, but picked up the phone anyway. Crowley's eyes followed it like it might suddenly bite. "I'm going to leave him a voice mail," Cas said. "He's kept some of Dean's phones. He turns them on to check them weekly. He won't find out about this until Saturday."

It was Tuesday.

"…Fine," Crowley said grudgingly. "Plenty of time to do what we need to do."

Cas paused, finger hovering over the little line of text that read Dean Cell #3. It was, as the answering feature would tell him when he dialed, Dean's other other other cell. His stomach flipped at just the thought of hearing Dean's voice again, until it occurred to him that it was a real possibility he would see the actual Dean again. He set the phone down.

"What do we have to do?" he asked.

Crowley's face lit up. "Easy. Well. Kind of. I assume Squirrel is in Hell. Demons, after all. If he is, we can find him."

"Yes, you said that," Cas said impatiently. For a moment, the thought slipped through his mind that it was insane to trust Crowley, and that perhaps he should dispose of him and then try to find Dean himself. But it passed just as quickly. He was in no shape to mount an attack on Hell like he had six years before, especially not without a garrison of angels at his back. If he was going to go in, he'd need help from someone on the inside.

"Yes. Right." Crowley shook his head slightly, as if trying to marshal his thoughts. "Well. In Hell, there's a room of sorts, like those big security rooms they have in malls and banks and such, where a person can watch all the cameras. Of course, there aren't literal cameras, but there're spells and enchantments and so on that allow a person to see what's going on in all corners. All we have to do is get in."

He paused dramatically, making Cas wonder, "And how do we do that?"

"Well," Crowley said, "As king I had full access. As…deposed king with an angel as a wingman" (he smirked) "we'll have to take the back entrance. Lots of areas not often tread, by demons or anything else. Very Frodo and Sam sneaking into Mordor, if you catch my drift."

The phrase sent several thoughts and images cascading through Cas's head, which meant that it was a pop culture reference instilled by Metatron. He frowned briefly, sorting them out, then said, "I see. Like when Gollum let Frodo and Sam through Cirith Ungol to reach Mount Doom, nearly causing them to meet their destruction by the giant spider Shelob."

"Erm…yes. Exactly," Crowley agreed, squinting at Cas in plain confusion. He rubbed at his immobile shoulder with a mild grimace before going on. "In any case, we should be able to get past most of the nasties if we take a few ill-trodden routes. Once we've located Dean, we can find a way to free him. That's why I need you, after all. They won't be expecting an angel. Not even one whose batteries need a good recharging, long as you don't mind a few tough spots."

"I'm fine," Cas said, then regarded Crowley thoughtfully. "You're hurt. How can I be sure that you're up for this?"

Crowley glanced down at his shoulder, as if surprised Cas had mentioned it. "This? Souvenir from my grand escape. Barely a scratch."

Cas nodded, satisfied for the moment. He found that, as insane as it was to trust Crowley to lead him through Hell for simply the chance to find Dean, with no guarantee that they'd even be able to free him, or that Crowley wouldn't simply try to kill him as soon as he didn't need him anymore, the last few months without his friend had been so painful that there was really no question. Of course he'd go after Dean. Of course he'd risk everything he had.

The memory of standing over a bloodied Dean with an angel blade raised, as Dean choked out, "I need you," sprang to his mind unbidden, as it did occasionally. But now, instead of the usual rush of mixed guilt and amazement that Dean actually felt that way about him, he felt only one thing: a certainty that as much as Dean had once needed Cas, Cas needed Dean. Without Dean, his life was empty.

"Very well," he said finally, eyeing Crowley. "How do we begin?"

"Well," Crowley said, eyeing him back, "first things first, angel. Put on some bloody pants."