All of the feeble warmth radiating from the sun was sucked away as soon as Dean stepped over the threshold and onto the factory floor. Spring in the late afternoon was replaced by dank undertones that were even worse than the putrid mix of early flowers; in a passing thought he wished he wasn't so used to settings like this, but the notion left as quickly as the temperature dropped.

This place had once been a brass mill, before the market crash forced the business to close up and move north into Connecticut's industrial sections. Another company had moved in, but only used half of the space. As Dean walked the floor, past spare pieces of abandoned machinery, buckets full of metal shavings and black oil, he could still hear the bombinating echoes of other hardware running on the other side of the building.

The only hint that the area wasn't as abandoned as it should have been was the man who was walking steadily, surreptitiously behind him.

David Ludensky – that was his name – was the equivalent of an intern, a slightly familiar face. He had come by his apartment an hour ago, not long after he had gotten home from work. Ludensky had explained that Crowley had something for him, and now they were here, in East Flatbush. As they got closer to the most foreboding area of the factory, Dean could just begin to smell dried blood, oxidizing on the floor like rust.

Old buildings had their charm for smuggling operations and meeting spots. Some were so good people got killed over them. But this place was special.

You could, for example, beat a guy to death in here, and with the other part of the mill going, no one would hear them screaming.

"Can't get shit outta the guy," Angelo Moreno said, stepping out of a cleared out office room – it was just a three-walled alcove, with a long plastic sheet acting as the ceiling and fourth wall. Angelo was older than Ludensky or Dean – older than Castiel, too. His nose was flat like it had been broken in one too many times, and his expression was perpetually angry, no matter where he was or what he did.

"That's 'cause they won't let the damn kid talk," Dean said, already drinking up the bloodlust this project demanded. "Get 'em outta there." Angelo glared at Dean for a moment before turning his head, cheeks darkening as he barked a few rough commands in the native tongue.

Dean could hear a muted, wet sound, harbored pants, and it didn't take a genius to figure out someone had gotten punched in the mouth. Two men revealed themselves a moment later; both were a little older, a little rounder, and a little shorter – with dark hair and venomous eyes.

"Get yourselves cleaned up," Angelo ordered, eyeballing their sweat-streaked faces and bloodied hands with the same amount of disgust he had given to Dean. "Winchester's on." The two of them laughed and clapped him on the shoulder affectionately as they passed. Ludensky, on the other hand, got a patronizing 'Good luck!' in rough voices. One of them put something into his palm before going away, perhaps to scope the perimeter for curious workers on their cigarette break.

Ludensky was a messenger, simply put. He would round up Crowley's men and send correspondence when phone calls weren't an option, letters were too slow, and telegrams not personal enough. He hadn't been on the receiving end of a 'kill the messenger' attack or a variation of it – as far as Dean could tell, at least; his fingers and teeth were still there, even if he was twitchy and everything from his eyes to his hair were murky colored, washed out, and pale. Sometimes that was all that was needed to get marked as inexperienced, and that quickly sent you down with the dogs at the bottom of the family food chain. He was also Polish, if Dean placed the accent right. Even if Crowley hired from wherever, it didn't mean Crowley's men had the same picture of unity.

"I'm coming with you?" Ludensky asked quietly, growing even more ashen when Dean gestured for him.

"You don't have to hurt him, just fact-check for me when he starts answering questions in case I need it. Otherwise, stand by me and look like you'll a threat." Ludensky hesitated, so Dean brought out his arm, as if to wrap it around his shoulders in a friendly manner. "Stare at the wall behind his head; ignore him if he starts talkin' to you. Got it?" His tone was low so the kid in the office wouldn't hear them, but David might have mistaken that for kindness. At any rate, it got him heading into the office, Dean right behind him.

The guy in question was James Mondale. Some musician – too crummy to make it on the Tin-Pan Alley – who had to settle for some street corners farther south, in Manhattan. He hadn't done anything important, but he was reportedly with someone important – and that was good enough to get rounded up at dawn and dropped off here.

Dean didn't know how long, exactly, James had been tied to that chair in the frigid factory. He didn't know how long the Johnson Brothers had been working him over, either. His hair was thin and stringy; the shirt he was wearing had splotches of blood and more than a few tears in the material – even Castiel couldn't fix something like that. His eyes were squinting up at Dean, like he might have worn glasses and someone had snatched them away. His gaze then sluggishly looked over at Ludensky, who seemed more uncomfortable in the room than James did, even if he was the one strapped to a chair with bump on his forehead the size of a golf ball. Dean walked over to him, gingerly laid a hand on the top of his head and tilted his skull so that he was making eye contact with him.

"Know English, kid?" he asked gruffly. James tried to nod, realized Dean wasn't giving him the room to, and assented, betraying the truth in a layered tone. "Know your numbers?" Another strained 'yes' in response. "Okay- count to five so I know your brain's not crushed in."

James rattled off the numbers quickly; afraid Dean was going to ruin his face if he hesitated.

"Alright, good job." He nodded to himself more than to James. There was a metal chair in the corner of the room, and Dean dragged it forward with a grating screech, making both Mondale and Ludensky wince. He sat down in it, casually, about a foot from Mondale's form, as if they were two friends having a conversation. It also made it easy for Dean to move and hit him, if he needed to, the danger of that was important. "So Mondale – or, sorry, can I call you James? It's easier to remember James," Dean waited a few seconds before the other man murmured yet another 'yes'; unsure if Dean was asking or making a rhetorical request. "James, do you know why you're here?" He made it sound like he was curious, and James watched him skeptically for another few seconds until Dean's hand twitched against where it rested on his knee, and he blurted out:

"Ruby. They tell me it's 'cause I know Ruby," Dean smiled, bowed his head. At least this job was going to be easy.

There were two ways to interrogate – at least two that Dean used. You could beat the answers out of a person; get a pipe and go to town, only give them respite once they started to promise information. That's what the other guys had done to Mondale, and, to their credit, it usually worked.

Other times you needed a different approach. In fact, that's probably why he had been sent for.

James had been here 'all day', from what Ludensky told him. That meant that despite his abysmal career choice and lack of intellect, he wasn't so easy to crack. Isolation didn't get to him, not even a few rounds with fists and a chiv. There was something about him that ran deeper than physical stuff; you saw that in guys once in a while, even if they appeared like a stiff breeze would blow them over. When that happened you had to go for their mind.

"Ah, Ruby," Dean worked hard to keep a fond-looking smile on his face, even if he felt like he was walking on a volcano, anger ready to burst through at the chick's name. He had known about Ruby as quickly as he had known about Lucifer – it made sense, rumors had it they were in cahoots somehow, even if no one could prove it. Dean didn't need a shred of evidence against her, though. The second he had laid eyes on her he knew she was bad news.

"I used to work with her, you know." Now James appeared interested, and Dean kept on smiling, polite and calm and sane. He could feel Ludensky look at him, probably wondering if he had jumped off the deep end since stepping into the room. He looked tranquil, a bit humble, too, for effect; even James wasn't sure what to make of it.

Dean leaned back in his seat as if he was telling a story. "I've hopped around a bit, circle to circle. We've talked. Met at a party three, four years ago; I haven't seen much of her lately, but we were more acquaintances than anything." He tilted his head, again. "What? You look like you're thinking about something."

James opened and closed his mouth a few times. "C'mon, you can tell me." Dean prodded.

Finally the man said: "You knew her, really?" Dean shook his head to the affirmative.

"Brunette, longish hair, usually parts it in the middle – and one of the smartest, silver-tongued broads you ever met; right out of a pulp glossie, right?" James did the same baffled movement of opening and closing his mouth. "Just seems too good to be true," That finally got another one-word affirmation, and Dean nodded again, this time a bit more sympathetically.

"You know her a long time?" Dean inquired, politely.

"No, just – just a few months. Durin' the winter she started listening to me play," He almost smiled, before running his tongue over the cut on his bottom lip. "She told me she could get me an act."

"Where?"

"Anywhere – it doesn't matter if you're a mouthful from starving," Dean shrugged a bit so James would continue his spiel. "She said I just had to – had to…" then he stopped short, as if realizing what he had just done.

Still, Dean kept on smiling in that urbane, recourseful way. People who were brought in for answers may be resistant to getting roughed up and bloody, but very few were resistant to that and a little inside manipulation. Sometimes the situation called for a friend, not a fighter, and Dean was more than happy to play both. He'd come in with a look on his face; an open, caring look; he'd let the person speak, answer innocuous questions that didn't matter, perform little tricks that weren't necessary to accomplish the ultimate goal. He'd idly chat as if they weren't in some metal icebox, as if one of them wasn't black and blue and red; usually they got the idea that response was a good thing, meant no more punches, and would oblige him. The talk could go on for minutes, half an hour at most until someone started to lose patience.

If they needed more persuasion, Dean would even light them a cigarette, clean up their wounds, say he was sorry – he was so new to this whole thing, to be honest, he was just doing this for him and his brother; 'Don't be mad at me,' he'd say, eyes furrowed and worried. 'Just – just tell me what you know so they don't send in anyone worse.' It was fun, trying to see how wide he could make his eyes go, how innocent he could seem.

At a point, the victims started to look at Dean like a warped version of their punisher and savior – someone who was to be simultaneously thanked and blamed. It messed with their heads, threw them too much off guard; after a while they would inwardly ask why they wouldn't indulge Dean in the answers to his questions – it only appeared to be making conversation, after all. If he actually got around to threatening or hurting with that sort of group, it would be a shock to their system – a punch to the stomach would hurt like a bullet to the heart, because they thought Dean was a friend, an ally in the mess. They wore down to nothing, eventually – everyone did with that sort of treatment.

Alastair had proven that firsthand on Dean enough times; he'd be lying if he didn't get some thrill on acting out what he had been on the receiving end of for so long.

"Cat got your tongue?" Dean asked simply; "I know, I know, Ruby's a nice girl – you wouldn't want anything to happen to her." James didn't blink. "But you have to understand – she's all grown up; and she's been caught for worse stuff than whatever she's having you do." He eased up out of his chair, cast a look back at Ludensky; he had gone back to staring at the wall, just like Dean instructed, though when he felt Dean's gaze on him he nearly jumped; his left hand clenched, and Dean was reminded of what had been put there, before he turned his attention back towards the restrained man. "She tried to go along with my brother, matter of fact. Didn't really work out – can't say I'm heartbroken,"

He lightly stepped around James's spot on the floor. His hands were at his sides and he moved in a natural stroll; nothing would seem dangerous about his ambling figure at that moment, unless, of course, you were tied to a chair, forced to watch a person slowly come in and out of view, vaguely wondering if you were about to be shot in the back of the head. "Especially when I found out going in for the long-haul is kind of her thing."

"You're lying!" James hissed out; Dean stalled a moment, but continued his prowl.

"I promise I'm not. What point would it be to lie about my brother?"

"She wouldn't do that to me – she loves me!"

"You're a musician, kid – girls like you on principle. Love's a different thing. Doesn't happen in a season, no matter what the poets tell you," He let out a long, tired sounding sigh, even if his blood was buzzing under his veins with adrenaline. "You seem like a nice guy, James, I'll give you that. Patron of the arts – I like reading myself, though admittedly if I'm going somewhere with music it's more like a club than an opera."

He put a gentle hand on Mondale's shoulder. "So, let's insinuate this – Ruby is taken with you like you are with her, and she may or may not be doing a very bad thing; we're not keen on killing her, to be honest I'm surprised if anyone wants to touch a hair on her head – we just want to know if a theory we have is right."

"What sort of theory is that?" James bit out.

"You tell me; what'd she tell you to do?"

Another long, long pause stretched on. "If she loves you she should forgive you for your slights," Dean offered, wondering how long they had been there in the room. James was probably getting stupid from hunger, sometimes his head lolled slightly when he hadn't done anything for a while. "And it's hard to stay mad at a guy in the hospital."

"What?"

"You've been beat to hell, James – you didn't think I would take care of it for you?"

"Those other –"

"–Forget about the other guys; they're low class schmucks. I wouldn't have done this to you. I haven't done anything to you yet." This time Mondale's hesitation was more considering, like that brief moment of lucidity that had been wrought by Dean insulting Ruby had been snatched away from him, and he was back to asking why, exactly, he shouldn't just do what Dean was so nicely asking.

"And… and you won't hurt her?" Dean smiled again; this time the expression was different – predatory with too much teeth, though the only one who could see it was Ludensky, who immediately attempted to look somewhere else. Dean eased the look on his face again and slowly slid back into his seat.

"'Course I won't hurt her – no one would hurt her. We're all not interested in taking hits out on people – sometimes we're helpers, too. Ruby knows about us – gang life is like breathing to her, trust me. She'll understand you did what you had to do; I'm sure she's in the same boat; doing what's necessary."

"Think so?"

"Swear on my grave – she's craftier than I am. Even if you did end up in a hard spot, she'd be able to get the pair of you out of it in a minute." James stared at his feet for a few more moments, and Dean let him mull it over – not long enough for him to come up with an iron-clad lie, of course, but enough to make it seem that he was being considerate. "Got that answer, James?"

Mondale looked up at him, dark eyes trying to search his; the beguiled look was on thick, and not a second later the guy had finally, willing cracked – he seemed happy about it even, as he started to tell Dean about the notes Ruby would put in his violin case every morning – insignificant pieces of paper that had 'strings of numbers' – or, as Dean gently persisted, addresses to meet-ups Crowley had going on. People would come by and pick them up – bulls, undercover cops, and Crowley's men got arrested or scattered. In exchange, there was more business for whoever Ruby was working for – probably Lucifer, though again the evidence was based on rumors and his own intuition. "So I got a little extra money from it – she said she was just weeding out some troublemakers, I didn't figure it was like… like this," James surmised.

"To be fair, she's done a better job cleaning the streets than the suits are, these days." James looked like he would've smiled, if his lip wasn't open and sore. "I'm sure you two will have a lot to talk about, though, huh."

"I… I guess so, yeah."

"Do you know where she is now?" James looked thoughtful for a moment before shaking his head. "You sure?" Dean pressed.

"She says she has a sister she goes to, all I know is that it's on the East strip of the bay."

"She mention the sister's name?"

"Uh, M-something. Margaret? Mary?"

"Meg?" Dean guessed.

"Sounds right, couldn't say. She never talked about her personal life much,"

"Understandable." He moved the chair back towards the wall with the same horrid whine, before reaching into one of the pockets inside his jacket and taking out a small knife. James looked worried again.

"What are you doing with that?"

"Cutting you loose, of course." Dean said simply. He turned his head towards Ludensky, silently requesting his attention. "Don't have to ask you not to try anything funny, right?" he said, slicing through the rope around the man's ankles, then the ones that had bound his wrists together behind the chair, now rubbed red and raw. Dean stepped back, holding his knife like he was just about to attack James if needed, but the man just massaged at his leg and groaned at the renewed pain in his extremities. "Can you walk?" Dean asked; he looked behind James towards the room's sham of a doorway, and saw Angelo staring at the three of them, as unimpressed as ever. He pointed to the oblivious, beaten man, mouthed the word 'hospital' at him, and Angelo slid out of view again, probably rounding up a driver and someone to keep James complacent in the backseat – they would give him a story, or punch him till he could think of one himself, but it wasn't Dean's problem. The second he walked out of the makeshift-office his part was done, and he was that much closer to paying his debt to Crowley.

After a few shaky steps on Mondale's part, one of his torturers from before stepped into the room. James scarcely let a word of surprise out before he was being dragged in jagged motions, fast enough that he nearly crumpled to his feet with each step. Dean watched on emotionlessly, there was no use in pretending to care about the kid, now.

"Wait!" James gasped out, sending a flurried look over his shoulder where Dean – his friend – was, though all Dean bothered to offer him was a twisted, cruel smile that parodied the one he had been making, passively watching the man be dragged out of sight without lifting a hand to help. The burly man holding him kicked his ankles every few steps or so, like he wanted to do the most damage with one move.

"See? Wasn't too bad," Dean said, rolling his gaze over to Ludensky, once the other men were gone. They went out of the bare room, onto the open area of the factory. They were alone again, and the scent of blood had been refreshed, like a new coat of paint.

"Think he'll make it to the hospital?" Ludensky asked anxiously.

"Who knows? Oh, by the way," He walked towards a side exit on the opposite side of where he had come in. "What'd those guys give you, anyway?"

Ludensky opened his sweating palms to reveal four gold rings, polished to a gentle glow, like they had been used and cleaned with care many times. They all had blocky, square faces, and two of the rings had small raised designs like a pyramid.

"Huh," Dean muttered, putting them on a card table with a well-used ashtray on it; someone would return to find the rings there. "Wondered why his face looked like that."

xxxx

Factories were death traps – Dean knew that by now. He walked out into the sunlight, blinking hard, catching a tinted car driving down the road at a ridiculous speed. He longed for some blinders to keep the sun out of his eyes, some object to prevent reality crashing back into him full throttle.

Sam had always been too good of heart to be in this sort of schtick, but he was hanging on by the ends of his teeth and toes.

He started walking, wanting some time to numb his brain – there was always a moment of panic, of asking existential questions that bogged him down and kept him alert, but in a few miles it would be put away, and he would forget the whole thing. Until next time, at least.

It was easy to ignore the things that he did – the fact that he killed and cheated and stole for a living, but because he got money through a pyramid scheme it was better than going solo. He hated moments of clarity like this, but he needed the catharsis.

There had been a time, some months early on, where he had tried to get rid of the shock to his system by burying himself in it. He had always blamed Alastair for it; for edging him closer and closer to the deep end, but really, he had already figured that if he didn't have it in him, he couldn't have gotten that low. If it wasn't self-loathing and disgust holding him back, there would be a slippery slope waiting for him – and then what? When he had gotten too invested in the business, Sam reeled him back in, made him see what sort of monster he was turning into. Seeing that tore into him for the first time since their Father's death. And by then they were working under Lucifer, where things were more systematic, easier.

Usually he didn't have to break people open like that, anymore – at least not people who didn't somehow deserve it. Dean silently warred with the ideas forming and swirling around in his head, arms akimbo and stuffed in his pockets, like people would see the blood on his hands otherwise.

When he saw the modest apartment building come into view, he felt a small wave of relief string through him. By now, Dean had a routine that dealt with the fallout – the aftermath of a high profile job. He got into the apartment, locked the door shut, and took off his shoes and coat – material sliding off his shoulders and hastily hung up on the rack. Then he washed his hands; he always washed his hands, even if he hadn't touched anything, the smell would linger there and drive him crazy. Already he was irked by it, through the entire walk home. Looking at his fingers now he could see that James had gotten some dried, dark smudges on his skin from when he held his scalp, and those rubbed off like old scabs. He kept his hands under the faucet for another minute, until his skin turned pink and he felt clean again.

It was worse with murders, but the way James looked at him as he was being dragged out made him accountable; not guilty enough to help him, of course, he never felt that bad; but after the adrenaline eroded and everyone else had gone, he wasn't left with much else but reflections, no original thought to be had, a deadness in the center of him.

As an afterthought, he bent over the faucet and splashed scalding water on his face. He blindly reached for a towel, sighing into the starched cotton. A moment later he lifted his head to stare at his reflection in the mirror.

Castiel was behind him, watching.

"Jesus!" His arms flew out to their sides and he spun around. "Don't do that."

Castiel swallowed, tossed his head to the side. "Sorry. I wondered why you didn't say anything when you came in."

"Oh," Dean wiped at his hands, distractedly putting the towel on the edge of the sink. "I – I didn't see you. I get pretty one track after a," he let out another sigh, "after a job." Castiel continued to stare inquiringly. "I had to play question and answers with some kid who's familiar with one of Lucifer's rats. Well, a possible rat – nobody has dirt on her. Some other guys had already come by and loosened him up for a bit." He walked out of the bathroom, Castiel following.

"So you didn't hurt him?"

"Not physically, no. You don't always have to. One of those skills you pick up on."

"Lucifer taught you that?" Dean snorted, making his way over to the table. There was a stack of letters from Sam, and he suddenly felt a jolt, a new sense of abandonment that he hadn't experienced to such an extent in months.

"No, Alastair. Practiced it on me enough times."

Castiel thinned his lips, perhaps unsure where to turn the conversation. Dean felt soiled again; James was a nobody, but the last time he had felt this guilty for a job was Doctor Romano last year.

Castiel, of course, was familiar with the sort of things he got up to, and could handle the news – he knew Dean had worked for Alastair, first; knew that he wanted nothing more than to slaughter the bastard.

"Why would a don want to ruin his own workers?" Castiel quietly asked beside him.

"Alastair was never a don, not even at the height of his power; he was insane, he was crazy." Dean clasped his hands together and he still felt blood under his fingernails. "He thought I was like him," Castiel wordlessly put a hand on his shoulder.

"You're not." Castiel supplied blankly. To him it was a fact; he was better than a washed-up torturer that still haunted his restless nights.

Sometimes he didn't feel better than that, though. He had a feeling that he would be keeping James up for a long, long time. Dean sank sluggishly into one of the chairs; after being worked up for so long, it was getting high and crashing, in a way. He felt tired, but merely rested his head in his hand, letting Castiel act as a reassuring, good presence next to him.

After a few more moments Castiel went back to where he had probably been sitting before, at the end of the table. Dean cracked an eye open and noticed that some playing cards were scattered across part of the desk.

"Where'd those come from?" he asked.

"Balthazar gave me a pack the other day," Dean was too muddled to even register the name with anything malicious, his eyes slipped closed. "I was playing."

"I didn't know you played cards for fun."

"Doesn't everyone, from time to time? You can only read for so long."

"You can read for ages," Dean muttered.

He heard the tight crush of cards being shuffled and collected together; it was familiar, the crisp and clean way thick paper flicked against each other. Comforting, perhaps. "Well, you don't get good at something without practice."

"I thought you wouldn't want to play poker after that mess with Crowley last year."

"Has it been nearly a year? I've forgotten," Castiel said evenly, still turning the cards over again. It took a moment before Dean realized the other was being sarcastic. "But I'm not playing poker," Dean opened his eyes again.

"Doesn't look like you're playing anything."

Castiel was flipping the cards over fairly quickly, one after another, only pausing for a second to peer at whatever the value was, before setting them face down on a steadily growing second pile. "I'm not – not at the moment," he said, after nearly all the unseen cards were spent. He stared at the second to last card in his hand before putting it face-down on the haphazard pile. "Want to see a trick?"

"Sure," Dean said, easing up a bit. He leaned forward in his seat while Castiel picked up the last remaining card, holding the face up to Dean instead of himself.

"Is this a two?"

"Sorry, an ace." Castiel frowned, flipped the card over, only to see that Dean had been lying. "It was a joke," he said in defense when Castiel flicked the card – the red two of diamonds – at his head. He chuckled a little and plucked the tag from where it had landed on the table. "Impressive. I didn't know you count cards."

"I don't. I'm not a terrible player, so I usually don't have to. It's a challenge to keep all the values straight in your head, but I have sometimes half a chance of being on the nose."

"So you were born with it?" Castiel shrugged.

"I'm a fast counter – arithmetic was easy, fractions are like chance – learning the game itself is the hardest for me." He tapped his fingers on the messy stack and already Dean felt worlds better than when he had walked through the door. "Can you count cards?"

"Sure, if no one's talking to me and there's only half a deck to work with." He reached for the cards and collected them together, jumbling them through. "When it's for work there are usually a couple of spotters planted that help keep a count, an ace up their sleeves or something. Cheating's hardly a one-man operation,"

Castiel smiled a little, before switching to a considering look. "Do you think Crowley would let you go if you made enough money gambling?"

Dean snorted. "Get me a casino and ten grand to play with and I'll see what I can do – the way I'm going is a lot simpler, anyway."

"Dealing with people?"

"A person or two is a lot easier to waste than a whole bag of chips." He split the deck and folded them in together.

"Is it easier for you?" Dean hesitated. Castiel's concern was warranted, comforting, too. It was something of a relief to know that Castiel could bear to hear what Dean got up to – if not in a newspaper than from his own mouth. But it was still untrodden ground, mentioning how he dealt with it all. When he and Castiel got together he hadn't done any heavy-handed stuff and there wasn't reason to bring it up.

"No," he said simply. "But when has life been easy? For either of us?" Castiel continued to stare at him. "Hey," Dean held his gaze. "I promise you that when all of this is over, we won't have to worry about this – it'll be different. Better, okay?"

Castiel looked down at his hands. "Yeah," he said. "Okay."

Dean put the cards in the middle of the table. "Want to play with me?"

Castiel stopped looking quite so morose, and leaned back in his chair, relaxed. "Sure,"

"Name your game,"

"Twenty-one. You can be the dealer."

Dean smiled. "I haven't played blackjack in ages." In fact, he hadn't played a simple, for-fun game in a while. "I used to play it with Sam a lot, actually. We always played cards when we got bored." He slid Castiel the top card – two of clubs, then his own card, face-down. Castiel's second card was a Queen, and he put a five on top of his hidden card. "Even when we were kids – I remember the two of us making up a few games. Hit or stay?"

"Hit," Dean put down a three of clubs. "Hit," Castiel said again. Dean placed an Ace on the line of cards next. "Were they fun?" he asked, looking up at Dean again, instead of his hand.

"I'm sure they didn't actually make sense. If I recall right I made some game rules where the oldest brother wins automatically," Castiel smirked, then scratched his fingers against the table, the gesture prompting Dean to put down a fifth card, two of clubs. "Getting a lot of low-rollers,"

"You probably just didn't shuffle them right," Castiel said, still smiling. He laid his fingers on the Ace.

"Thought you weren't allowed to touch the cards in a game," Dean supplied. "Hit or stay?"

"Stay," Dean flipped over the unknown card, revealing a King of Diamonds. "Fifteen to eighteen. Congratulations." He slid all the cards away with a quick motion of his hand and started another round, giving Castiel a five and six, while a King was put on top of his pair.

"What was Sam's last letter about?"

"Jess – he's so in love, it's worse than those sonnets you had me read you,"

"I thought they were sweet."

"I thought I was going to throw up – on both counts," he folded his arms across his chest, game forgotten temporarily. "They're not sure what they're going to name the kid yet," he said quietly. "He still doesn't know about Lucifer."

"Well you're going to tell him, right?"

"'Course I am! Just… well there's never really a good time to admit that kind of thing, is there?"

"There's no safe way, either. If the wrong people get hold of your mail – I mean, who says they haven't yet?" Dean worried his lip.

"I had a plan for that, actually."

"Oh?"

"Yeah. I – well, I'll get to it soon, I promise," he sighed. "Hit or stay?"

"Hit."

"Really? I could have an Ace in here for all you know," Castiel just shrugged, and got a Jack for his troubles.

"Okay, now I'll stay."

Dean's overturned card was merely a two, and Castiel smiled again, slight and triumphant. It was a lovely look; Dean hadn't seen him straight win something in quite a while, anyway, even the simplicity of friendly competition didn't hinder his appreciation. He swiped the cards again and opened his mouth when a knock resounded at the door.

All he could think of for a moment, before the paranoia settled in was, 'Again?'

They both stood up; Dean still had a gun hidden away in his pocket, and he reached for it while getting out a gruff, "Who's there?" at the door. Castiel was a silent specter behind him, not sure if their company meant that he should be there or not.

"It's Adam," was the response; Dean had never felt so terrified at the idea of a family member on the other side of a door, trying to get in.

He turned around to look at Castiel. The easy happiness from before had disappeared, and in its place he had a terrified look at the corners of his eyes. Dean had told him about Adam, had also mentioned the suspicion that had arisen from his half-brother finding 'girly' books and a suitcase during their trip to the Catskill Mountains. Adam was family, but he wasn't a friend. Not in this moment, not for Castiel, and he couldn't be seen here.

Adam knocked again, heavy chimes like the tolls on a bell, and Dean stammered out, "Just a minute," over his shoulder, stowing the pistol away and turning back to a desperate Castiel.

The bed was no use; everything was too out in the open. He briefly thought of the wardrobe before getting Castiel by the shoulders, pushing him into the bathroom. "Get in the tub," he whispered, the other quickly went in, sinking down as far as the porcelain depression allowed. "Don't move or make a sound until I say so, got it?" Castiel mutely nodded, slowly pulling the shower curtain around the elevated rod. Dean shut off the washroom's light and shut the door behind him; he could only hope that Adam wouldn't need to clean his hands.

Dean took three steeling breaths before unlocking the door and facing the waiting man.

Dean hadn't been completely cut off from his brother – he still saw him, passed his neighborhood and called up on him when he had the time, but things had gotten stilted between them the longer they spent under different bosses.

Adam looked a little rough around the edges – pale, skinny, like Dean had been when he was a teenager and constantly ravenous. "Kid keeping you up?" Dean said, slapping a last minute smirk on his face.

But Adam didn't seem to register the friendly greeting. Instead he dragged his gaze briefly around the room, then looked at Dean. "Can I come in?" he said. Dean nodded, letting the door shut behind the pair.

"What's wrong? Need a drink or something?"

"No, no, I won't stay long." He rubbed a hand down his cheek. "I had to tell you something."

He figured as much, though it didn't exactly calm him. "It's about Lucifer, right?" Adam got a worried look on his face, like henchmen were about to bust open the door for saying a person's name.

"He's been taking me around more and more, as a bodyguard, I mean. He says I'm a good shooter,"

"Does he still think my guy's after him?"

"Less so, but yes. Crowley hasn't made any moves yet, and it's been more than half a year; but he's still convinced that something big is going to go down." Dean found himself biting the inside of his cheek. "Everyone's been in a frenzy, trying to figure out if some family in Manhattan has something up their sleeve, or if it's Crowley, or Alastair –"

"He couldn't think that Alastair has enough gray cells left in him to do anything?" Adam shrugged helplessly. "So what, he's having all of you spy for him?"

"In simple terms, basically. He hasn't gone off the deep end yet – don't give me that look; really, he hasn't. But I'm with him more and more, and every time someone comes to him, reports some finding or fact or lead… it's crazy, how deep this whole business runs."

"Mafia's the blood veins of New York," Dean dully added, feeling his own pulse run heavily in his ears. He still wasn't sure why Adam had stopped by.

"Lucifer can get any information he wants."

"He can find the people who can get any information he wants."

Adam wiped his mouth. "Yeah," he muttered. "Like you." Dean blinked.

"Like me? Is he trying to hire me back?"

"No – no, but…" Adam stopped abruptly again, like he was trying to speak but had to go over some gargantuan obstacle in his way to force the words out. He was visibly struggling, for a full on minute, before he finally said, "Ms. Milligan got sent into the hospital last week."

"I'm sorry," Dean tried to muster all the authenticity he could at the abrupt comment. Adam's mother wasn't exactly old, but he wasn't sure why this gained notice.

"It's TB, according to the doctors."

"Oh, god, Adam," he put a hand on his shoulder.

"I had enough money to send her down to Florida – they said the warm air would treat her better, but medicine, and a decent place for a thing like that is next to impossible."

"…You had Lucifer give you a loan," Dean said, his tone and touch slipping away in mild horror. Adam nodded, slowly, looking partway ashamed and frightened himself. "How long till you pay it back?"

"He said I didn't have to – not with money, at least. He wanted to be generous." Adam didn't say 'generous' sarcastically, either. His brother was younger, a little naïve, but he seemed to be more anxious about his mother than thinking about what Lucifer would do to him, especially now that he dangled a job and a favor over his head. "He told me I can repay him with information – valuable information."

"You're a spy now?"

"No, I – he wants more dirt on Crowley, he wants to know why he hasn't challenged him yet. He wants to – to know something, anything. Nobody important to Crowley will tell me facts like that. But – Dean, you have to help me."

For a second – just a minuscule amount of time, Dean considered shoving Adam out the door and never letting him back in.

But he couldn't do that – Adam was family, trying to help one of the last blood relatives in his own life. And hadn't Dean promised? Didn't he always promise? "What sort of information do you need?" he found himself saying.

"A-anything. People Crowley's working with; CEOs, other mafia members, the jobs he's pulling for lately, where he goes for fun on Saturdays – whatever you can tell me. Lucifer wants to know Crowley like the back of his hand. And, you're here on a deal between them, but – Dean, I know you," he said, raising his eyebrows. "You're too good at this sort of thing to be on the bottom rung forever. You're ruthless – you're loyal, you'd do whatever's asked of you – Crowley has to like you, because Lucifer did, and Alastair did – I mean, this is who you are."

Dean took in a breath, held it for a few moments. The room was silent; he couldn't hear anything outside, he couldn't hear or even sense Castiel's hidden presence, and even as Adam grew animated with his spiel, without a voice he looked just as dead and desperate as ever.

And Dean, so badly, wanted to say no; claim that he owed nothing and be done with it; he wasn't meant for this – Castiel said so, Sam had said so, even he had accepted it. Oh, he was good at playing crazy, and then after a while not playing so much, but you couldn't keep the job and stay human, and if he didn't keep that one blanket sentiment of humanism with him, carried it like a shield, then what did he have to separate himself from the monsters?

But Adam was right when he said he was loyal; not to Crowley or Lucifer or Alastair, but he was loyal to the people who earned it, and Adam was on that list preemptively by being blood. "I can't promise anything," Dean said hastily. "I know what you're saying, but I bet Crowley doesn't trust me that much." Which, he knew, was a lie. He could tell Adam the secret he was harboring – the one even Sam didn't know about. If he did, Lucifer might reward the both of them; he might be able to double-cross Crowley and come out with his skin.

But maybe not.

"There's a – a guy I know," he said suddenly, surprising himself. He had to give Adam something decent, something at least partway true, and this was the first dirt he could think of. "We've been around together and he doesn't work for anyone, but he's seen Crowley with some guys – important, rich types, at parties, playing cards. He has their names, and I can start you off with that." He could feel his own blood rush from his face, even as Adam began to grow a less sickly complexion, as if he was feeding upon Dean's own essence. "I don't know how much I'll be able to prompt you after that – Crowley, well, it's hard to tell, but you know that we can't hang around each other so much. We haven't, anyway, but especially not now."

Adam nodded. "I understand. I just, didn't know who else to turn to." He paused. "You'll let me know if anything's going on with you, right?" Dean jerked his head to the affirmative, trying to remain steady.

"Of course. Things are fine for me at the moment but – you know, I'll be here."

Adam smiled, for the first time since he came by. "Thank you, Dean," the sincerity behind it all was enough to confirm that Dean was in the right by helping Adam – by risking his own status, maybe even his own life. "You said I could count on you, and, and I'm glad I could." In a quick, compulsive gesture, he hugged Dean, too fast for Dean to recognize the gesture, much less return it. "Send it as a letter or a telegram or whatever you can, and, and anything else, as you see fit."

"I will," Dean promised. He cast another look outside, and felt uneasy all over again; maybe helping Adam was the right decision, but his brother still wasn't in the best place. The sky was darkening, and street lights flickered on. "It's getting late. Don't keep the missus waiting, huh?"

"Oh, right." Adam went to the door, gaining confidence with each apparent step. He was out in the hallway, and Dean put his hand on the aperture, meeting Adam's eyes.

"Give my regards to your Mom, and the family. And be careful," Dean warned, even as Adam looked magically better than before.

"I will, and you too, Dean." He gave his older brother a wave before slowly walking down the hall.

Dean softly shut the door on his half brother and leaned against it, closing his eyes and letting out a puff of relieved air. "Jesus," he murmured. He eased himself up enough and walked into the washroom, turning on the light.

Castiel was in the bathtub still, his feet resting against the porcelain sides, making his knees tip up like two black-clad mountains. His hands were interlocked on his chest, and he stared up at Dean with wide, unblinking eyes. "I take it we're safe?"

A fully dressed man in his tub was asking if they were alright; wasn't that enough of an indication? Dean couldn't even bring forth any humorless laughter at the sight; instead he just slumped against the side of the tub, propping his back up against the white. His head hit against the lip of the bathtub and he groaned – not out of pain.

"I think I just kicked myself out of the family again."

"Which one?"

"The real one and Lucifer's. Adam's playing a snitch now."

"Nobody likes a look-out," Castiel conceded. "Did you tell him about Crowley's plan?"

"I can't – I couldn't," he rubbed a hand through his hair. "Lucifer's got Adam locked up tight – he said his mom's in the hospital. TB; there's no cheap way to fix that."

"You don't trust Adam?" Castiel wasn't accusatory, just inquisitive.

"I trust him more than I'd trust most people, but that's his mother – that's the only true blood family he's got left – that he cares about that much, at least. If I had the chance to get her back –" he paused, realized what he was saying. "If I could've saved my mom, a half brother I've only seen a little of ain't going to change that, and I can hardly recall her."

"He's not coming with us, then."

"No. I – no, I don't think we can risk it. I know you, and the rest of your family enough, and they'd never sell you out. I don't blame Adam for picking sides; family's family, after all."

"You're his family, too." Castiel supplied.

"Not the one he wants right now." He felt something in his belly clench and cut at the thought; he put a hand to his abdomen, just to be safe. Castiel eased himself forward so that he rested his forearm by Dean's head. "He wouldn't like you, anyway, remember?"

"He didn't notice the books?"

"We were staring straight at each other, mostly, or at least his eyes were on the back of the wall; anything close enough to make out didn't get a once over, I'm sure."

"Isn't my tie on the headboard still there?" Dean couldn't quite recall everything they had gotten up to last night, much less whether they had straightened things out, after.

"Well, I can make up something for that – he won't know it's your tie, after all." Castiel hummed in agreement, and Dean pressed on, not wanting to talk about Adam any longer. "Did you manage to tell Anna and the rest of 'em?"

"That's not the easiest thing to do," Castiel admitted. "I would go anywhere with you, they would go anywhere with me, but no one is clamoring for that sort of change."

"I hear you," Dean closed his eyes; he still wasn't too sure when Lucifer's death date was set out to be, but it wasn't going to be anywhere in the next season; he still had to buy his way out for the Novaks – they had till fall at the very least, and it was just springtime.

"How about I tell them the plan when you tell Sam?"

"Fair enough," Dean said, and they sat together in the washroom for a considerably long time after that.

xxxx

Dean thought it was fair enough to say that nothing spectacular happened after Adam's visit – not for the next few months, in any case. He and Castiel managed to go to the state shore in June, trading the brackish, dirty waters of the bay for dull, cold ones. Dean continued to remind him that waters in California were better, and Sam's letters continued to offer proof, as if even from across the country his brother wanted to help sway an argument, though he had no idea that Castiel would be coming along, just yet.

That's where his thoughts were trailing, one day in July, as he went through the apartment and sorted out clothing to carry over to the tailor shop. Every two weeks one or the other would put the laundry in bags and get a free wash; it was better than using the unreliable washer the apartment building had – they didn't have a dryer, either, so Dean had to wait for a guaranteed sunny day to let them drip-dry on the window sill.

Since he and Castiel were the only two who usually saw the inside of their place, clothes were normally strewn this way and that; balled up by the foot of the bed or stuffed in a heaping pile by the chairs, a mess of white, black, and dishwasher gray; denim, cotton, and silk. Dean paused for a moment, looking at the shirt he had scooped up – sometimes it was hard to tell until one of them put on the piece of clothing and saw how it didn't fit, but this one might have been his – the shirt was a slightly nicer quality than the ones Castiel wore in the shop. It was still crisp enough to suggest it had only been worn for a few hours. Turning it over in his hands, he spotted a red streak, nearly hidden, on the top of its collar.

"Huh," Dean said aloud, trying to recall the last time he had gone somewhere that required a nice shirt in the last few days. Unless it had been sitting around for a while but – no, no, that didn't seem right, not if it was bundled up with other things. Maybe it was Castiel's.

He scrutinized the small splotch of color – about the size of his fingernail and faded, like it had been rubbed into the material. It was the color of blood, but bringing it closer it didn't give off a rusty smell. In fact, he caught something else; a quiet, passing scent like it hadn't been there at all. A sweet smell; honey, lilies – it was a perfume.

Despite being alone in the apartment, Dean suddenly turned and looked around the room conspiringly, clutching the garment in his hands like it was about to be ripped from him at any moment.

His mind became a frantic, terrifying race that tried to come up with explanations as quickly as another part of him made accusations.

It could be anything, Dean told himself, thumb running over the stain. He had never seen Anna wear lipstick, but sometimes she had rouge or kohl on so it wasn't out of the question – she never smelt like lilies, either, but Castiel saw her much more than Dean ever did. And – and Castiel did know other people, he hastily reminded himself; neighbors, customers, a drunk stranger could have approached him on his way home from work. Even Balthazar maintained that Castiel didn't care for women. There was obviously an angle Dean wasn't seeing at the moment, that had to be it.

Because if it was anything else…

He swallowed harshly, like he couldn't breathe right, and balled up the shirt so tightly he hoped it would rip. "Cas wouldn't do that," he whispered, eyes shut, the floral smell invading his head and choking him, even after he tossed the shirt down and backed up until he could sit heavily on his bed.

He watched the crumpled top, lying abandoned on the carpet, stain in place looking more pronounced every time Dean gave it a glance. He didn't move for a long time, thinking of nothing, everything, wondering first if Castiel had ever at all seemed off, tried to ignore him, and then hastily thinking that he had never done anything strange – Castiel said he wouldn't hurt him, and he hadn't been wrong; in fact, it had only been Dean who let Castiel down: Early on when he had laughed at the idea that the two of them were good for anything more than a quick roll around in the sheets, and later at Crowley's card table, and even after when he got mad enough to push him away and break the goddamn window – all through that, Castiel hadn't done a thing, why now? Why this? It didn't hold water, the idea of Castiel being unfaithful, and he left it at that.

It didn't make a lick of sense, and if he had some wit about him he would just ask Castiel himself.

That's what he should have done, but instead, at quarter to six when Castiel was almost due home, he got back to the pile of laundry and stuffed all the darks, coloreds, and whites into their respective bags, the crinkled, stained shirt still oozed that sickening smell, even when he pushed it to the bottom of its sack like he was burying a body instead.

Castiel arrived, as regular as ever. Dean kept his mouth shut, didn't hint at a thing. There was a reason he wasn't seeing, he repeated furiously to himself, a constant mantra that lasted four hours straight until bed.

Usually they slept close; entangled after sex or touching because they wanted to. But the thoughts kept him too aggravated to act naturally anymore, so he turned away from Castiel harshly, staring at the wall, and then to the black bags that housed that dirty secret like a heart burrowed under the floor boards. He could still feel that floral mist around them, and for a time he thought that Castiel had actually carried it in with him. But that was ridiculous – impossible. Even if Castiel did go behind his back – not that he would, he reminded himself, gnashing his teeth in the darkness, he was too smart to come back to him smelling like it.

Eventually sleep overtook even the suspicions, and upon waking, Dean felt normal for a split second, like it had all been a jealous dream.

Then Castiel, partway asleep besides him, shifted, moaned, settled back into the pillows, and for the rest of the day Dean couldn't even bear to look the other man in the eye.

xxxx

A/N: I went a little crazy on slang in this chapter. Tin Pan Alley is a slightly curved street that ran through Manhattan; it housed a lot of famous street performers. The Johnson Brothers was a term for mobsters or general henchmen that liked cracking a person's skulls open. When Dean mentions a 'pulp glossie', that's a reference to a pulp fiction magazine, which were popular at the turn of the century. They were 'pulp' due to the cheap unrefined paper the syndicated stories were published on – they were usually about sex, science fiction, crime, or a mix of the genre, and were generally considered trashy. That brings us to the card game. Blackjack, or sometimes called 21, had been played since at least the 1600s with a few variations. It's a bit easier to understand than poker, however. Basically, you play against the house, or dealer, and try to get an amount of cards that exceed the hidden value of the dealer, but do not go over 21. Those who can count cards find this convenient if they play with a large group over a long period of time, because one can eventually determine what the dealer's hidden card might be, and drop out of the game before they lose all their money, or increase their bet and win more. And as a last note, while the ending is a bit dismal, I offer readers to come up with their own explanations as to how Castiel's tie ended up affixed to Dean's headboard (and I may be tempted to write that out myself.)