"Glad you like it, Cas." They kept passing the bottle back and forth until it was empty again - Castiel offered to refill it but Dean waved that thought away; his head was already swimming and the last thing he wanted was to be hung over for the big fight. Instead he made Castiel settle back on the bed, ignoring his token protests that he didn't get tired. It was a tight squeeze; they both had to lay on their sides back to front to fit on the narrow bed, and they were close enough now for Dean to tell that Castiel was shaking like a leaf. "Cas," Dean said, putting one hand on his arm. "You gotta relax."

Castiel shook his head. "I can't quiet my mind." He let out a long breath that just seemed to shake him harder. "It was...it was easier the first time when I didn't fully comprehend what I was facing."

Dean swallowed hard. He knew what he should be doing but it still took a second of telling himself to get over it for him to wrap one arm around Cas' waist.

Castiel sighed, relaxing slightly against Dean. "It hurt," he whispered, so softly Dean barely heard him. "The smiting. It hurt a great deal."

Dean tightened his grip, the flash of rage hitting him so strong and so fast that he couldn't speak for a few seconds. "It's not gonna be like that," he said into Castiel's ear when he could trust his voice again. "The plan's solid. That son of a bitch isn't going to touch you, Cas."

Castiel didn't answer, instead twisting around to lay on his back and almost falling off the bed before Dean steadied him. "Tell me again what I did wrong at the brothel," he said, looking up at Dean; Castiel might claim he didn't get tired but Dean didn't think he'd ever seen anyone look as exhausted as Cas did just then. "You said I...spoke too much. What was I supposed to do?"

"Well, not talk to the chick about her father, that's for damn sure. Talk about killing the moment."

"I wanted to set her at ease."

"Look, Cas, the girls in those places know what you're in there for. You don't have to chat them up to get them in the mood."

"I wasn't trying to..." He sighed. "I'm not even certain what that means." He waved his hand back over the whiskey bottle to refill it and took a long swallow. "I didn't know how I was supposed to start things."

"Next time you're in that position, just kiss her already. Well, ask first, some hookers don't go for that, but yeah. You don't need to exchange life stories."

Castiel scowled. "I probably wouldn't be very good at it."

Dean shrugged, stealing the bottle for one more taste. "Eh, it's not that complicated. Takes a little practice."

Cas let out another sigh. Dean was starting to get the feeling he was morose drunk. "I'm unlikely to get the chance for much practice, Dean."

Dean heard alarm bells go off. It was one thing to go into a fight scared, Dean did that all the time, but you never went into one beaten the way Cas was now. Castiel rubbed his face, his hand shaking so hard Dean grabbed it before he could even think about what he was doing. Cas looked up at him and Dean didn't know if it was the booze but he'd never seen Cas' eyes unguarded like this; the hopelessness he saw there reached out and wrapped around him like a physical thing. He thought about Castiel sending him to Sam that day in the Chuck's apartment, lying that he could fight them off even though he knew damn well death was coming for him. He didn't remember if Cas had been shaking this hard then, too. He hadn't been paying attention.

Dean took a deep breath and kissed him before he could talk himself out of it; Cas tasted like whiskey and his stubble scratched and when his lips moved under Dean's to return the kiss Dean couldn't understand what the hell had been wrong with him, why he'd hadn't done this ages ago. When he broke the kiss Castiel's eyes were so wide with astonishment Dean almost kissed him again. "See, Cas?" Dean said, tracing his thumb along his jaw. "You did that just fine."