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BETWEEN THE CITY & THE STARS - Part 2

Pairing: Dean Winchester x Reader

Summary: In the fall of 1945, Dean is having a difficult time assimilating back into civilian life after the War. He’s visiting his brother Sam in New York City, where he’s beginning to build up his law firm. At two minutes to closing time, you interrupt their evening to solicit a solicitor. Your request? You need help in order to divorce your husband.

AN: Before we tune back into some 1940s drama, I just wanted to thank you all so much for your wonderful responses on Part 1 of this series. 🥹 It’s my first time doing a story like this, so I’m very happy you liked the jumpstart here. 💖💖

Prompt for @jacklesversebingo: Historical Epic

Song Inspo: “I’ve Got You Under My Skin” by Frank Sinatra

Word Count: 3.7K

Tags/Warnings: Angst, hints of PTSD, flirting, dancing…

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Part 2: Devil May Care

After you got home from work the very next day, your apartment was entirely empty.

Predictable. Michael was still out.

This time, you counted it as a blessing. You rifled through every corner, cabinet, pocket, and drawer in search of evidence—anything you could use to prove, without even one shade of a doubt, that your husband was the unfaithful scoundrel you knew him to be. You knew it, deep in your gut. In your very soul.

You even rifled through Michael’s desk in his office, through every single folder, drawer, and booklet. You’d never done such a thing before because he was a particular man about his things, and you respected his privacy.

That was done now. In your search, you found a useless ball of rubber bands and old coupons. You took his father’s old collection of fountain pens, which you knew Michael was precious about, and threw them haphazardly onto the desk to make room for your seeking hands through the rest of the drawers.

You even came across a small, crumpled photograph from your wedding day. This one made you pause.

You considered the picture, its bent corners and slightly grainy black and white lens. You’d worn your mother’s wedding dress, and you stared up at your new husband with the rosiest of smiles. He stared into your eyes then the way he always used to—like a man ready and willing to drown in them.

You sighed and let the picture fall from between your fingertips. It swayed onto the desk’s mahogany wood surface, and rested there. You shook your head and returned your attention to your task at hand, holding your hands to your hips.

The problem was, you didn’t see anything incriminating here…until an idea finally occurred to you. You went into Michael’s closet. You sorted through the suit jackets he still needed to get drycleaned and pressed again.

In one of the pockets, you found a receipt.

You brought it to Sam Winchester’s office the following morning before work, along with some documents of your household expenses. Like you did the afternoon before, he identified the receipt as one for the Cotton Club, a nightclub in the Upper East Side. You had never been there in your life, but you heard it was one of the new go-to spots in town. It was the kind of place you used to wish Michael would take you to, once in a while.

“It could be a lead or it could be nothing, but I’ll check it out, along with these,” Sam said. He gathered the financial documents you gave him as well.

“Okay. Thank you, Mr. Winchester,” you nodded.

“You can call me Sam if you like,” he said, kind, but still professional. You smiled. Unbidden, it reminded you of his brother.

“Please,” you said, your eyes briefly closing. “Just…call me by my name. My first name.”

Dean slowly smiled. “Perfect. I like your name better anyway.”

This time, your smile in return was genuine, if tinged with amusement.

“Goodnight, Dean,” you replied.

Biting the inside of your lip, you gave into the urge to ask the question.

“It was nice of your brother to walk me home last night…what is he up to today then?”

“Ah, well, he’s out to lunch with a young lady he met last night,” Sam replied, with a somewhat wry, but still amused tone to his voice. You frowned.

“Last night? Does your brother meet a lot of women after 9:00 p.m.?”

Sam chuckled. “He’s not usually wanting for company.”

“I see,” you said flatly. You should have known. The devil-may-care grin on that man was too charming to be anything less than the mark of a shameless flirt. Maybe even a scoundrel. Lord knew you couldn’t take any chances either way.

Dean returned from his day out with Vanessa. She was a nice enough girl, a knockout blonde too. She was smart, studying to be a schoolteacher. But she also tended to twitter on about frivolous things, so much that he couldn’t really remember much of what she said. She did look good doing it though. Not to mention, she let him feel her up while they kissed in one of the alleys, between the ice cream parlor and a drycleaners.

He predictably found his brother whittling away life in his office. Dean dropped his coat and hat on the hanger with a flourish. Sam raised his head from his work with an amused smile.

“Had a good day, did you?” he remarked.

“I can’t complain,” Dean agreed. “Especially when a beautiful woman’s involved.”

Sam shook his head. Before September, he hadn’t seen Dean in three years. Yet some things just didn’t change.

“You gonna see her again?” Sam asked.

Dean made a noncommittal sound. “We’ll see. The day is young, brother.”

Sam raised a finger. “Speaking of which. Mrs. Milligan came by this morning. I’ve been looking through her husband’s finances.”

“Oh really?” Dean sobered as he approached his brother’s desk. “What’d you find?”

“Overall, things seemed to be in order, until I noticed something strange,” Sam said. Dean lowered into the chairs opposite his brother at his desk, and they went over it all together. Sam appreciated another set of eyes on this, with the understanding that Dean would keep the information to himself.

Starting roughly eleven months ago, there was a check signed to a Mr. Johnson for a moderate sum. Three weeks later, another check, this time a bit larger. For the past few months, Michael Milligan had been making these payments at least once a month, sometimes as much as three, albeit in different amounts.

“He might just have a gambling problem,” Sam said. He rubbed his chin in contemplation.

“Or it could be what she’s worried about,” Dean pointed out. “The name could be an alias. Maybe Mike’s paying for someone’s services…or paying her bills, if you catch my drift.”

Sam slowly nodded. “That’s a possibility.” He checked the dates on the documents again and shook his head. “Mrs. Milligan told me they got married about a year ago, here in the city. It would mean this guy started stepping out on her a month after the wedding.”

Dean both could and couldn’t believe it. He might not have been a saint himself when it came to the fairer sex, but if he went through the whole ordeal of marrying one, let alone a straight-shooting woman like you, beautiful, clever…

“Geez,” he muttered. “He could’ve at least waited until the ink dried on the certificate.”

Sam nodded in agreement. He picked up the receipt to the Cotton Club, and he shot his brother a grin.

“Wanna go to the club tonight?”

A wall of sound. That was the Cotton Club—the band on stage playing jazz tunes, loudly, if skillfully; the clanking of glasses as drinks rolled past; the clamor of heels and leather shoes as couples swung on the dance floor; and the added layer of people raising their voices to compensate. The room was filled with the smell of cigarette smoke, fighting against perfume and cologne and musk and sweat.

It was a bit overwhelming for Dean at first. He tried to ease himself into the scene with Sam at his side, even if he did jolt at the cork of a champagne bottle popping open. Sam noticed, but he mercifully didn’t say anything. He thumped a hand on Dean’s back to steady him under the pretense of a brotherly pat, adding a smile for good measure.

Sam was there to keep a lookout for Michael Milligan. Dean would help, but it wasn’t like he was being paid for it. He was largely aiming to have some fun while his brother was all serious, focused on the work. Dean was here for the community nightlife.

The beautiful, beautiful community. As a matter of fact, there were lovely ladies everywhere. One sultry blonde was singing an upbeat, jazzy tune at the mic. Dolores Daye, said the banner above the stage.

Dean’s attention shifted from the stage to the scattered round tables outside the dance floor, as well as the chair lined up at the bar. His gaze caught on someone familiar—on you, sat at a table by yourself. His eyes widened. He slowed to a stop while Sam went on ahead.

You were stunning, almost unrecognizable in a shimmering black dress that hugged every lush part of your figure, with sleeves that draped off your shoulders. His eyes drew down your crossed legs, the sheer pantyhose, leading to a pair of tall, shining black heels.

You wore a hat and partial veil that covered half your face, but he knew it was you. Those lips of yours were familiar on sight. Now they were painted red, dark and luscious.

“Dean?” Sam questioned him. He’d turned back when he realized his brother wasn’t keeping up with him. Dean subtly pointed you out. Sam raised his brows, but then he noticed what you were doing. You had a glass of wine in hand, and you seemed to be watching someone.

Every now and then your gaze would travel across the room, where your husband Michael was sat at a table filled with other men and women. They were laughing, drinking, playing cards.

Sam and Dean shared a conspiring look, one that said they had the same thought. They went over to you.

Sensing you were being approached, you looked over and found the pair of tall, familiar men with a widening of your eyes. That pretty mouth of yours fell open in surprise.

“What’re you doing here?” you whisper-hissed. You beckoned them to sit down so they weren’t standing out so much while talking to you. Both Winchester men were broad-shouldered and tall as oaks.

“The same thing you’re doing, apparently,” Sam said, once he and Dean were sitting across from you at the table. He showed you the camera he had hidden in his coat pocket. “I’m going to see if I can get a read on what your husband’s up to, maybe collect some evidence.”

You let out a rush of breath. “Good, thank you.”

“Until then, maybe you’d be more comfortable at home,” he suggested.

Dean knew what his brother was getting at. This wasn’t the kind of place for a woman to be hanging around…unaccompanied. Not a respectable one like you, who clearly wasn’t used to being in a roaring nightclub. Plus, if Michael did slip up here, it wasn’t exactly going to be pleasant for you.

You still shook your head stubbornly. “No. I want to see it with my own eyes.”

Sam almost sighed, but Dean shot him a nod. Right then, they had an understanding. Dean would stay and look out for you while Sam tried to get closer to Michael. Sam left you and Dean together at the table thereafter, and Dean ordered a drink for himself. You sipped at your wine.

Dean glanced at you in appreciation. You really were beautiful…and not just tonight. Though he had to smile at your “disguise.”

“You think that getup is gonna fool your husband?” he remarked, gesturing at your form.

Your lips pursed, but you kept your head angled towards him, so that your hat and veil continued to hide your face from Michael’s direction.

“It has so far,” you retorted. “And this isn’t a getup.”

You smoothed slightly self-conscious hands down the skirt of your dress. Dean smiled.

“All right, I’m sorry. Poor choice of words,” he said. He dropped his chin and raised his brows, earning your gaze under the hat. “It’s quite a dress, sweetheart.”

I’d like to see you out of it, he thought, even though he immediately stamped it down. You weren’t exactly available, no matter how delectable you were. The interesting part was, you didn’t seem to realize it as you fidgeted in your seat, a little self-consciously.

“Is that supposed to be a compliment?” you snipped.

His lips tugged at a smirk. He tilted your hat up a little so he could see more of your frowning face.

“Want me to do better?” he teased.

“I’d like you to leave me be. How about that?” you said, grabbing the edges of your hat and tilting it back down. “You’re distracting me.”

“Oh, I’m distracting?”

You met his gaze to give him a hot reply, but your words failed you. Just then, faced with his perfectly handsome, roguish face, you finally noticed how green his eyes were. Holding the gleaming reflection from the crystal chandelier above the bar, they briefly dragged over you again, like he was a starving man, and you were the very last morsel held in front of him.

It was indecent, you thought, but suddenly your mouth had gone dry.

“How about this,” Dean said. He finished off his whiskey and held out a hand to you. “Dance with me. You’ll have a better vantage point to spy on Mike over there.”

“Keep your voice down,” you shushed, glancing around.

Dean just smirked. He beckoned you again with a raise of his brows.

You hesitated, but you still eventually dropped your hand into his. He stood before you so he could help you to your feet. You allowed him to escort you over to the dance floor, and all the while you fought off your nerves. You were only doing this because he had a good idea; this would help you keep an eye on Michael without looking so out of place, a woman drinking alone at the table.

The band was playing a moderately paced song, which was good. You weren’t in this to be swept into the air.

“Relax,” Dean whispered, once he had you in his arms. His hands were respectably placed on your waist and in your hand. You knew you did have to relax though. Already you were too stiff while tentatively holding his hand, your other resting on his shoulder.

“I haven’t danced in—in a while,” you admitted. You were a little nervous as you began swaying with Dean, letting him lead you. He turned you about with ease, even twirling you under his hand.

“See? There’s nothing to it,” he said, welcoming you back into his arms. “When’s the last time you had some fun?”

You tilted your head as you thought about it. You and Dean shuffled about the dance floor in more complicated steps as the song increased in tempo. You were breathless in a good way. In a way that you couldn’t even remember needing to breathe as the golden lights sparkled in the corners of your eyes.

“He took me to a club like this once, about…I’d say month or so after we got married last year,” you admitted between spins. You had to hold a hand to your head to keep your hat on.

You were distracted enough by it all—the spinning, the laughter and tinkling glasses, the flashes of spotlight in between sultry dim shades, the heady smell of this man’s cologne, and his every touch, however brief on your body, but just as confident and measured. You actually told him the truth.

“I’ve been dying to get out more ever since, but…” you trailed as he spun you again, then winded you back into the growing familiarity of his arms.

Dean smoothly guided you even closer to him by your waist, until there was hardly any room between your chest and his, between your face and his. Your hand curled around the back of his neck on instinct, the edge of your nails just barely grazing through his hair. You wouldn’t know how it elicited a hot zing of sensation down his spine.

“Your husband really is blind, and even dumber than he looks,” Dean said, glancing down at your face. “I clocked you in five seconds flat, just by those pretty lips.”

You lowered your eyes, but not very far. They landed on his plush lips in contemplation. When your eyes met his again, Dean had a conundrum. He just didn’t think he cared all that much about the consequences.

His head began to bow towards yours, just when the song slowed to a stop. Almost without realizing it, he pressed his hand a little more insistently on the small of your back. You found yourself accepting that guiding pressure. Half-lidded eyes and heavy, mingled breaths in between…

“Let’s hear it again for Dolores Daye, everybody!” the host called out.

You snapped to attention and glanced over Dean’s shoulder at the singer. She waved goodbye to the crowd with a sensuous smile on her ruby red lips. Then she walked off stage in her glittering golden dress, and she grabbed hold of a man’s tie. That man was your husband.

Michael wore a wide smile on his face as she led him to his feet by his tie. He stood, his form looming over her, though she didn’t seem to mind—especially when his arm wrapped too familiarly around her waist.

It wasn’t the kind of embrace you would see between strangers, even for the sake of a good show for the crowd. Their faces became impossibly close, but it was just shy of a kiss as she laughed, a sound like fine crystal bells.

Dean noticed why you froze. He turned to look over his shoulder and his expression faded, becoming grim. He led you off the stage, and while keeping a discreet eye on the scene, he lingered at the bar in the center of the room. His arm stayed around your waist. He could tell himself it was to stay in character, but really, he just wanted to keep you grounded…that right now, you weren’t alone.

Here by the bar, it was far enough that Michael likely wouldn’t notice you, but close enough that you both could hear what was happening.

The host stepped down from the stage and joined Dolores and Michael, laying a heavy hand on your husband’s shoulder. Yet another clue that Michael showed his face here all too frequently. The host waved over his entire table of friends, Sam included. He’d managed to get himself invited to sit with them.

“Come on. Join us out back,” said the host, gesturing behind the curtain.

“Where to?” Sam asked.

“For a card game or two, a little smoke, a nice little drink,” Michael said, grabbing Sam’s shoulder. “You in?”

Sam nodded. He glanced over and found Dean across the room with his eyes. They shared a brief, but telling look, after which Sam followed Michael and Dolores past the curtain discreetly. Meanwhile, you were already pulling away from Dean’s arm.

“I’m sorry. I’ve got to go,” you murmured.

You went back to the table to collect your purse. You left the rest of your wine there with a few bills on the table to cover it, and you were off, walking brusquely to the front doors. Dean followed suit, laying some money down for his own drink before he followed after you. The clerk at the front brought you your coat after you handed over your ticket, and Dean did the same.

“Hey, why don’t I take you home,” he said, having to raise his voice even here over the noise.

“No, thank you,” you said thickly.

After you had your coat on, you hastened to the closest bus stop outside the club. It was late, it was dark, and it was cold. You saw your fragile breath on the air as you stood there in your tall heels, and you held yourself for more than one reason as you fought off bitter tears.

You bit your lip and blinked against the burn, but you still had to swipe a few droplets quickly from your cheeks. You tried to even out your shallow breaths. It felt like someone had reached into your chest and started squeezing whatever they found. Whatever was left.

Dean sidled up to you with his hands in his pockets. You heaved a sharp sigh, recognizing him just by his shadow casting beside yours under the streetlamp. You kept your face away from him as you wiped at your tears.

“Why do you insist on watching me be miserable?” you asked.

“Aw, come on, sweetheart.” He shook his head, carding a hand through his hair. “I know you’re upset. I just want to make sure you get home safe, that’s all. …You don’t even have to talk to me if you don’t want to.”

You slowly shot him a glance, but you didn’t budge. Your frown deepened along with your furrowed brows.

“Dean, please. You don’t have to do this just because you feel sorry for me,” you said.

“I don’t feel sorry for you,” he said.

It earned your attention, your confused and hurt expression.

Dean met your gaze steadily. “I feel sorry for him. Because he doesn’t have a clue what he’s just lost.”

Your breath stilled in your lungs.

His words touched you, more deeply than he probably realized. Part of you still wanted to give a sharp retort, that you didn’t need a chaperone. You didn’t need him to swoop in and collect you like broken glass…but a larger part of you craved the company. You didn’t want to be alone.

Soon enough, the next bus pulled up at the curb in front of you. The doors opened.

Dean gestured with a sweeping hand towards the bus’s steps.

Ladies first.

With another small sigh, you climbed up without a word. You even accepted his helping hand as you did so. Dean stepped up after you, and the doors closed behind you both.

AN: Welp, Happy Valentine's Day! 😅💜 Quite literally an angsty ride here, but what should happen on this bus going nowhere...

Next Time:

You admired his hands as they rested casually in his lap. They were larger than yours, with long fingers. His hands look strong and capable, like the rest of him, even though they were always considerate when they touched you.

“Then you should do something you like doing,” you said. “Fixing cars! That’s good, honest work you can make a living out of.”

Dean looked over at you. “You think so?”

You nodded your encouragement, smiling bright. “I know so. You might be a bit of a flirt, but you also look like someone who can accomplish whatever you set your mind to.”

When those words slipped free from your mouth, you realized how he might take that little accusation, let alone how overeager you sounded. Your gaze fell away from him as you felt your face getting warm in a blush.

Dean’s smile slid into a smirk. “I’m a flirt, huh?”

“Well…” You bit the inside of your lip and tried your hardest not to look at him for a while. “At least you’re an honest one.”

Dean laughed freely at that.

▶️ Keep Reading: PART 3