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Man at the Crossroads

Summary:

Cordelia (paralegal) needs to know who the hell this leather jacket-wearing, cheap cigarette-smoking rough trade is. And just why his rolling into town is shaking up her normally so-calm boss, lawyer Sam Winchester.

Notes:

(See the end of the work for notes.)

Work Text:

Cordelia hated her name. She hated her hair, and the ugly, cheap, boxy low heels that seemed to be required uniform for women in legal. She hated the way the old files she had to collate, full of dust mites, set off her allergies and made her contacts all but useless by halfway through the afternoon. She hated 2/3 of the clients her firm defended, at a conservative estimate, and 3/4 of the other professionals in her field. She hated the way she had to go a full block around from the courthouse exit to smoke when they were at the district court, and hated the shit-weasel lawyers and A.D.A.s who made shit-weasel comments to her over their own cigarettes while she tried to soothe the jones in peace, and she hated the way she always–always–spilled coffee on her left cuff when she ran back to her place after the too-short breaks, only to find the judge and opposing counsel dragging their feet and not rolling back in for another twenty minutes. She was starting to think it was possible she might hate her job full stop, her entire field, and most of humanity to boot.

But she did not–and this was very important–hate her boss. Small miracles, she'd gathered (usually the boss was at the top of a paralegal's list of nightly hate prayers), but Mr. "Please call me Sam, Cordelia" Winchester wasn't like the other lawyers.

He listened when she spoke. He valued her insight, or made a convincing show of it if he didn't. He seemed to actually, bafflingly, respect her and her capacities, and didn't sit in chagrined discomfort or smirking approval when other lawyers made passes or shit-weasel comments equating her value as a human to her tits and her ass in a business suit. He suddenly became 6'5" instead and said something scathing and bitchy like how he was dazzled someone could get through the rigors of a law school education with all the basic human capacity of a masturbating chimp, and he was just suddenly too damn big and menacing for the shit-weasels in Brooks Brothers to say anything stupider. And he was good-looking, too, tender eyes and broad shoulders and gorgeous hair, make-you-jealous hair, gleaming must-be-expensive hair that still somehow looked natural and unpretentious.

Yeah, maybe she had a bit of a crush.

Part of her wished he would hit on her, even if it might ruin a bit of the magic of him. Part of her hoped he was gay, instead. The alternative–a straight, available, evolved male, whom she personally could not bang without fucking up her career prospects–was just a little too depressing. As far as she could tell he didn't date at all, though he could just have a better work/life barrier than most. But that would be fine, too; he could be an asexual monk or something. "Off the table" was the important part.

But while she tried to get coffee out of her cuff as usual with a paper napkin and water from her eco travel tumbler (Mr. Winchester had had some made for their firm by a union printshop that employed ex-cons), she heard him take a sharp breath and looked up to see what had actually made a wrinkle in his normally unrufflable, earnest demeanor.

He looked like he'd seen a ghost–or maybe a startlingly tasty morsel, she amended, when she'd turned to follow his eye into the gallery.

A beautiful man in a brown leather jacket was taking his time easing down into a seat in the back row, eyes lasered in on her boss. His hair was peaked with gel (not her thing, she preferred Mr. Winchester's glossy hair, curling loose but neat just under his jaw) but his lips were fuller than hers even with the stupid plumper her sister had convinced her to try. He looked hard, five o'clock shadow at noon, bruises on his knuckles she could make out even from here, a dangerous looking scar above one eye, but there was mirth in his eyes, and maybe hunger, too.

So maybe that was Mr. Winchester's style. Rough trade. Heat bloomed under her polyester collar at that thought and she pretended badly that she hadn't been staring by leaning to rifle through the messenger bag at her feet.

When the images that thought brought to mind distracted her badly enough she couldn't retain anything from her notes, she scolded herself silently that she was just being stupid and horny and there must be some better–or at least less distracting–explanation.

Probably a former client, she reasoned, someone Mr. Winchester had saved from prison but whom he'd thought had fallen into the system after all. The gasp was surprise and relief. Or he was a blackmailer! But then, what could her boss possibly have to be blackmailed with? Though she supposed you never really knew. But the man did seem... predatory. An extra-legal of some sort? That could work, he had a bit of that bounty hunter look about him.

Yeah, that could definitely work.

Maybe he'd brought in one of Mr. Winchester's missing clients for a loan shark, once, she mused, a little too bruised, and now her boss's hackles went up whenever he rolled back into town. Mr. Winchester was at his scariest when he thought anyone was abusing the defendants, she reflected. She'd seen him single-handedly break a blue wall of silence once by sheer menace, fist in a guard's shirt and shoulders bulging under his suit and face promising fire, when a client had arrived to court with a concussion (that Mr. Winchester had somehow diagnosed himself–where had he learned that?). The cops and guards tended to bandy the whole "you wouldn't last a minute blah blah blah" bull when the lawyers got uppity, but Mr. Winchester had smiled one of those calm "fuck around and find out" smiles, dangerous in its very invitation, and things had fallen apart for the guards pretty fast after that.

She couldn't believe the threat was genuine, when she tried to bring it to mind later, but knew she hadn't doubted it was real at the time. There was something a little dangerous lurking deep inside of him, something spring-loaded and ready to snap. It was just hard to square with those soulful, jury-swaying puppy-dog eyes.

Were his hackles up? She tried to watch him surreptitiously from the corner of her eye as he pretended to be looking at his notes, but his gaze was off somewhere over the terrible sandpaper carpeting between counsels' tables and the bench. So he was distracted, too.

She couldn't say for sure (contacts, 1 p.m), but it looked as though there were goosebumps on his neck, peeking out under his hair. And–was he sweating? He seemed to notice it when she did, pulling a handkerchief to dab his neck discreetly before tucking it away. When the judge came in, her boss seemed to snap himself into focus as they all clambered to their feet, but she fancied he was keeping a death grip on his pen as he took notes, afterwards, and he couldn't seem to stop fiddling with it unconsciously betweentimes.

"What has got you so bent, boss?" she wondered silently, but she couldn't find a chance to ask about it after they broke session for the day, because he bolted, and that wasn't like him at all. Oh, he thanked her conscientiously for her work, first, but then he was out like a flash, packed up and fleeing before hardly any of the gallery had even managed to get out.

The maybe-bounty-hunter, maybe-hot-date was gone, too.

She resolved to take an extra close look at her boss in the morning. And if she maybe indulged the earlier fantasy a bit overnight, well, that was nobody's business but hers.

---

If there had been any lasting marks from the night before, Cordelia couldn't find them. She'd even sacrificed vanity for the purpose, coming to court in her least objectionable pair of glasses. Then again, Mr. Winchester had slid in too close to the bell to give her much time to look properly before things got going. That wasn't like him, either.

Something did seem different about him, this morning, she thought. But hell if she could say what it was.

Probably something irritatingly fleeting, she mused. Her sister would have said "his aura is off" but Cordelia tended to roll her eyes at that sort of nonsense. Still, he looked different without looking any different, however that might be possible. His hair was the same; he wasn't marked up; his nails were clean; his suit was tidy (and not the one he'd worn the day before). He didn't smell like a strip club or a hangover. The only concrete change she could track was in the pen, again–his motions weren't his usual controlled and tidy but neither were they the tense, jittering motions of the afternoon before. There was something erratic about the way he moved it, long zig-zagging motions, a strange energy.

Fuck. Maybe Frida was right. His aura had gone weird. She felt a headache coming on.

"Is this what you look like after a fight outside the courtroom?" she wondered. "Or after getting laid?"

Wait. She sniffed at some unfamiliar note on the air–was his aftershave a little different than usual? He was one of the few men around here who wore any without wearing so much it choked you, but there was something cheap-but-classic mixed in today, she fancied. Lectric Shave? Brut? She was hardly a connoisseur but it evoked an uncle she hadn't seen in a decade, and the image of the dimly lit bathroom in his apartment with its handful of curious bottles on the counter.

Embarrassingly, then, she noticed her own cigarette funk, though she'd last had one on her balcony before getting dressed for the day. Frowning, she pulled one of her own curls out to reach under her nose as surreptitiously as she could, but she only smelled product.

Her sister had warned her that smoking would mess with her sense of smell and taste. Cordelia closed her eyes and rubbed the tension in her forehead; she hated it when Frida was right.

"You all right, Cordelia?" Mr. Winchester murmured quietly in concern, leaning a little nearer while opposing counsel organized notes for the next witness.

Shit. It was him. He smelled like cigarettes!

She nodded shortly, dazed, keeping her eyes down on her notes in hopes he wouldn't see them bugging out of her head. Was he a secret smoker, buzzing after a long neglected fix? Or had he picked it up from... company? Whose? His? She only realized she'd missed her chance to ask about the tense afternoon before when the A.D.A. rose to begin his questions.

Damn. An opportunity lost. And fuck but she wanted a cigarette.

---

Mr. Winchester spent his lunch in conference with the client but told her she should take hers, and the need for tobacco was too strong for her to disagree. She made the usual brisk walk to the Ladies' and then to the courthouse cafe for a disappointing sandwich and passable coffee, shoveling down the sandwich with well-earned disregard as she headed out of the building. The coffee she nursed with more favor as she fished out her Slims on the shuffling jog around the courthouse to the designated degenerate holding pen.

Cordelia picked a wall as far away from the already present band of cutthroats from the D.A.'s office as she could and still be technically within the smoking area, holding the cigarette between her lips while she fished in her bag for the lighter that had slipped its usual pocket. Before she could turn it up, a distinctive shhhk of a Zippo and a pop of flame in front of her face startled her half out of her skin and she yelped.

Fuck, there went still more of the precious coffee.

"Sorry, beautiful, didn't mean to scare you," came a whiskey-and-unfiltereds gravel and a chuckle. "Just looked like you could use a light."

Her eyes were rolling before she'd even taken the would-be savior in, but her mouth went slack when she did, cigarette only saved by the way it was catching on her drying lipstick.

Fuck if it wasn't leather-jacket-bounty-hunter-rough-trade guy. She stared dumbly.

He was smoking unfiltereds.

He was wearing Brut.

...And he was watching her with one eyebrow quirked up. She flushed and tried to kick her brain back into gear.

"Close your mouth, Cordelia, you look like a fish," she heard in her sister's voice, and snapped shut on her cigarette, cautiously leaning forward to let him light it. She acknowledged with a nod as she sucked a breath to get it going and calm her nerves. The lighter snapped shut with a satisfying metal clink.

He leaned up against the wall beside her while they both smoked in silence, then, and she ruminated, trying to gather up her nerve for... something. Was this tense silence? A pregnant pause? She frowned and tried to look at him from the corner of her eye but the glasses, while clearer, were no help in the far periphery. Damn her eyes too, leaving him more of a colorful blur than a useful set of clues. And damn her brain, why couldn't she come up with some basic human small talk when she needed to?

"Saw you in court–" she finally blurted.

"You work with Sam–?" he blurted, at the same time, and they both stopped in nervous laughs.

"Sam? So we're on first name basis with my boss, are we?" she wondered, eyes narrowing on it. "Then again, If he smells like your cigarettes and aftershave, I should certainly hope you're on a first name basis."

"Just thought I'd take a look," he explained casually, shrugging, then watched her expectantly in side-eye.

"I'm Mr. Winchester's paralegal," she explained in turn, though his account wasn't very satisfying. "Do you, um, know him well?" At least she had the excuse to look at him more directly. That scar must have a story.

He grinned like a shark. "You could say that. Dean," he offered along with his hand, cigarette temporarily shifted to his left.

"Ah," she said significantly, reaching across her coffee awkwardly to shake, cigarette in her lips.

"Ah?" he repeated, suddenly on guard.

"Just the whole," she paused to wave vaguely, taking in the leather and denim and hair, "James Dean vibe."

"Oh," he replied, blinking, then grinned, seeming genuinely pleased with the comparison.

"Known him long?" she tried, more boldly. "Mr. Winchester, I mean."

"Forever," he said, shrugging again. "We were, uh, kids together." Now he wasn't looking at her.

She stared, dumbfounded. Childhood friends? She tried to imagine the two together as children, serious, studious Mr.–Sam, he'd have been, then, she supposed–and juvenile delinquent James Dean here. It almost worked; her boss did seem to have a soft spot for convicts. Could it go back as far as that?

"Your Sal Mineo?" she asked slyly, diverting back to her original rough-trade theory before she could kick herself and swallow it.

He pulled a flask at that–an honest to God flask, like some movie degenerate, right out in the open at noon in the California sunshine–and hid a smile in a swig. "Maybe so. Guess I better not take him down to Griffith Observatory while I'm in town, then, huh?"

An eight hour drive south wasn't exactly what she'd call "in town," but something sloshed a little sea-sick in her belly at the thought of the two of them in the forest under the stars, together, in some knife fight or a stand-off against the L.A.P.D.. Sal's character didn't make it out alive of that one, did he?

Suddenly, ridiculously, it seemed very important Mr. Winchester not run off with this man, friend or–or fuckbuddy or whatever he was. Not even for a weekend. The hairs were standing up on her neck.

"You'd just crash your Spider, better not risk it," she tried as a joke, an excuse, but to her relief he nodded, taking this in with a smirk.

"Just in town for a couple days anyway," he said, by way of setting it aside. "Don't suppose I'll be dragging him anywhere further than to a burger joint. Any good ones?" he asked, not sounding optimistic.

"Mr. Winchester doesn't eat burgers," she protested automatically. Hell, she didn't even think he ate meat. "He's more of a... a quinoa and kale guy," she trailed off into a mumble, as Dean snorted in derision, then grimaced.

"I hate kale. And for me," he confided conspiratorially, "he'll eat a burger. If it's a good one. Or if there's good beer," he amended.

"Ghost Town Brewery does a decent burger and a kale salad," she offered as compromise, and didn't understand why he barked a laugh. "About a mile that way," she offered anyway, frowning and pointing vaguely.

"Sounds perfect," he said, placatingly, getting his laugh under control.

Damn, now she wanted a beer. Well, she'd stop by on the way home from court.

Court. Fuck. Checking her watch, she gulped as much coffee as she could, in hopes of keeping it off of her perpetually stained cuff, and smashed out the cigarette. "Nice to meet you, Dean," she called over her shoulder as she started to run back to court, "don't get shot by the cops."

"I'll try not to," he promised, with another dose of illegal public consumption on federal grounds.

As she shuffled through the metal detector and prayed the judge was as delayed as usual, she wondered whether that might not be a real risk in his life, after all.

---

Cordelia was finishing her second pint of Dank and Deceased and deliberating on a third when she heard the laughter.

"No, seriously, man, you have to try it, it's called 'Salt the Earth,'" Mr. Winchester was insisting, buoyant. Dean had taken her advice after all.

"Yeah, and it also says shit about–about lemon and fennel and shit. I'll stick with 'salt and burn,' thanks, you try it." Dean, there, though she couldn't make much sense of that. "Just get me something normal. And we're both getting burgers," he declared, "don't be a little bitch."

"Jerk," Mr. Winchester said promptly. "I'll have the burger if you have the girly beer you were destined to have the minute we came in here."

Cordelia shifted around on her barstool just enough to get a glimpse of them at a far table. They were sitting across from one another, but crowded in so close that they could easily touch. Mr. Winchester's neat conservative suit made a bizarre match with Dean's dirtbag look, but their eyes had a matched intensity.

And Mr. Winchester looked... happy, she realized with a small pang. She hadn't realized she hadn't known what that looked like.

Dean narrowed his eyes like a poker player considering a bet, and then slapped the table in decision. "Deal. Bring on the salt."

Yeah, she was staying. It was a Friday night, and she didn't exactly have any more exciting plans lined up. Diego, her cat, was seventeen now and not exactly riveting company most of the time. She waved another pint from the barman and wound her way to the Ladies' and then to a cigarette in the alley to shore up for the stake-out.

When Cordelia made it back to the bar, they'd apparently finished the negotiations and arranged the thing because the waitress was delivering their burgers and fries while they argued about their respective beers. Dean insisted his was "a cursed object," which she thought was surprisingly poetic, but Mr. Winchester was rolling his eyes like a teenager and throwing ketchup packets at him.

When he bit into the burger, though, his eyes closed in what she was pretty sure was bliss, and it was Dean's turn, kicking him under the table. "See?" he gloated, through a mouthful of fries. "You know you love it, bitch."

Mr. Winchester ignored this somewhat loaded comment, but studiously licked the juice off of the side of his palm where it was running. It was probably the beers, but Cordelia felt her whole face flush.

She thought maybe Dean's did, too. He certainly watched like a starved man, even though his own burger was hanging forgotten in his hands.

Most of the rest of their conversation over dinner was conducted in mutters, with Dean periodically fishing something out of a duffle she hadn't noticed at his feet–a leather notebook, a newspaper, what looked disturbingly like a real animal skull–but Mr. Winchester waved it all away a bit imperiously, and Dean shrugged and knocked it all back into his pack.

"Whatever, Sammy." That carried.

Sammy? That right there, Cordelia was pretty sure, broke her brain. Mr. Winchester didn't seem to like it either, rebuffing him, but Dean just reached across the table to wipe a dot of ketchup off of his cheek before licking it off of his own finger.

Mr. Winchester–Sammy–shifted uncomfortably and waved for the check.

While the waitress took his card, Mr. Winchester went the direction of the Mens', coming back shaking his hands after what she guessed was an encounter with an underperforming hand dryer. As if to irritate him, Dean very deliberately smeared the grease off his hands onto some paper napkins, dumping them on the table, and stuffed his hands into his jeans pockets.

Cordelia sighed, paid her tab, and called a cab. She supposed she hadn't learned much about her circumspect–secretive?–boss, but at least the view had been nice. She hit the Ladies' one more time and, finding them gone when she returned, wandered out to the alley for a smoke while she waited for her ride. Maybe Diego would tolerate a cuddle, tonight, she thought without much hope.

Maybe her ex would drop by if she texted. She was almost drunk enough for that.

"...mess up your pretty suit..." drifted from further down the alley, on the other side of the dumpsters, and she froze, suddenly much more alert.

"Fuck the suit," Mr. Winchester was saying, and then there was a grunt, a faint groan, a wet sound.

What. The fuck.

"Come on, Sammy, let me take you home," Dean said, hoarse, through more groans, and then one of them gasped.

She couldn't quite make out Mr. Winchester's response, but she thought she heard, "...let you take me here..." and she stifled her own mouth. She needn't have worried; Dean's groan would have covered her wheeze.

As quietly as her inebriation would allow, she rearranged to huddle low and close against the wall, where she could just make out a slice of the alley beyond through the gap behind the dumpsters, faintly lit by yellow halogen. Fists gripped in clothing, a knee braced against the wall, a throat bared to teeth, leather and fine wool and denim mashing together or ruffling open.

Her cigarette, still unlit, was forgotten in her hand.

Their muttered conversation, carried on between what appeared to be a mutual mauling, made it to her in snatches. "...missed you..." then "...come with me..." then "...know I can't..." then "...oh, fuck, yes."

She was just wondering how close to live porn she was going to get, wiping the corner of her watering mouth, when her phone made a chime that she was certain in her heart of hearts was as loud as a gunshot.

Fuck. The cab!

The grunting and rustling stopped.

"You hear something?" That was Dean, tense and sharp.

"No..." replied Mr. Winchester, but he didn't sound convinced. She saw them break from the wall.

Closing her eyes for a brief prayer, Cordelia took a shaking breath and then bolted for the street, head ducked. "Please God please God don't let him see me don't let him recognize me," she thought in a panic, not bothering to try to disguise her running steps, and didn't look back until she'd hurtled herself across the back seat of the cab, waving the driver to get her out of there. She stayed ducked below the level of the window until he began to pull away from the curb, certain she looked ridiculous or alarming or both, but she would have to live with that and hope the driver saw sufficiently worse in a day that she wouldn't be a lasting blip on his radar. She would tip him an excessive amount in her embarrassment, when they reached her apartment.

The streetlights flashed a glare across her glasses when she finally dared to peek, but she thought she could make out two figures by the mouth of the alley, just far enough back to stay faceless in the shadows. Two men, looming and vague and dangerous, obscure in the night.

---

Come Monday morning, Cordelia couldn't stop sweating, tried so hard to not get caught either looking for or avoiding her boss that she ran into him, instead.

"Hey, careful," he said, warmly, bracing her before she could bounce off of him and into a door.

"Thanks," she said, not looking up, until she realized it would be even weirder if she looked at his sternum all day. So she braced herself, found her balance, plastered on a fake but dazzling smile, and turned her face up. She tried very hard to look only at his face, and not at his neck. "Why, no, never. Not checking for hickeys, no sir, not me," she thought inanely.

She wondered if she looked like one of those guys trying so hard not to notice your cleavage that they wind up staring at your hairline instead.

"Did you have a nice weekend?" he asked her, smiling, though there was a wrinkle of concern between his brows.

She swallowed at her suddenly dry throat. "Y-yes," she stammered, "I mean no. I mean–" she laughed nervously, shaking her head. "Sorry, my coffee hasn't kicked in yet. It was, you know, boring. So-so. You?" she asked desperately, to stop her mouth.

He laughed politely. "Same," he said easily, his smile reassuring. But in her peripheral vision (blessed contacts), she was pretty sure she saw the faint bruise of a hickey just under Mr. Winchester's–Sam's–collar.

She was almost able to focus on the trial, after that. Almost.

At the end of the day, she thought she was happy for him, chasing his bliss. Just so long as he didn't chase it too far.

"Stay here in Oakland," she thought, with a fervor she didn't quite understand. "Stay here in the light. Or James Dean will get you both killed, someday."

Notes:

For ashtraythief's lovely Spn Masquerade 2022 prompt:
WINCEST, CANON-DIVERGENT, LAWYER!SAM, HUNTER!DEAN:
Sam is a successful lawyer, so he keeps it a secret that his brother is a fugitive hunter who stops by whenever he can. They balance both of their jobs while still having a relationship. Would love to see people in Sam’s life catching sight of Dean with Sam and wondering what prim and proper lawyer Sam is doing with that dangerous looking, leather jacket wearing guy and what their deal is. My first born for outsider POV.

Title taken from a piece by the ancient cat's namesake.

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