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zepskies · 6 days ago

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BETWEEN THE CITY & THE STARS - Part 1

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: My day tomorrow is going to be a bit packed, so I decided to release this a bit early for you guys! So here we go! The first chapter of yet another new series, my first ever 1940s AU. 🥰 I hope you have fun on this one, because I sure did. Again, very much inspired by The Clock (1945), starring Judy Garland and Robert Walker. 💜

Prompt for @jacklesversebingo: Historical Epic

Song Inspo: For this chapter it’s “Cry Me a River” by Ella Fitzgerald

Word Count: 3.9K

Tags/Warnings: Angst, mentions of cheating, PTSD, historical tidbits

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Part 1: Legal Grounds

November 2, 1945

Dean idly read the pamphlet stacked with others on his brother’s desk, which advertised his new and successful enterprise.

Law Offices of Winchester, Bialystock & Bloom

What do you know? His brother had his own office, his own business, and his name on a pamphlet.

Dean couldn’t help but curl a finger around a steel ball on the abacus sitting at the head of the mahogany desk, right next to Sam’s nameplate.

He let it fly. The abacus began to clack as one ball hit the other.

Sam looked up from the deposition he was writing to give his brother a wry brow raise.

“So this is what you do, huh?” Dean remarked, crossing his arms.

Without his jacket, his suspenders were on display over his shoulders. His red pinstripe tie was still in place, but his white dress shirt was rolled up to the elbows. Meanwhile, his brother preferred to keep himself more presentable with his sleeves down to his wrists. Jacket on.

Dean glanced around the office, nodding at the line of bookshelves behind Sam, framing him as the bookish academic he’d always been. There was limited seating in here though, just a spare chair in front of the desk, and another to the right of it. Dean stood on the opposite side.

“If you’re bored, all you have to do is say so,” Sam said. “Which is strange, considering we’re smack dab in the middle of a city that never sleeps.”

He was right, Dean could concede. His little brother had given him a veritable list of things to do in New York City: visit the park, go to the zoo, see a picture show, visit a nightclub, or sample a host of restaurants that Sam knew Dean would probably enjoy.

He’d seen a lot of this place in the week that he’d been here visiting Sam, but a good deal of it he’d either spent alone, or with any willing young lady Dean came across, thanks to the demands of this office. If he was honest, entertaining young ladies was eating into the wallet in his trouser pocket, and the hustle and bustle was starting to be a little much for him.

“You don’t get tired of it?” Dean asked, gesturing to the out there beyond them. “The, uh…the lights, the noise, all the people?”

Sam picked his head up from his paperwork to consider the question. “No, I like it. Keeps my mind busy, and…I guess it makes me feel alive, you know?”

Dean supposed he could understand that, so he nodded.

Sam wasn’t fooled though. He thought he could tell what was running through his brother’s head, watching him fidget, and turn his head a bit sharply when a bus honked loudly outside the office’s glass doors as it thundered past.

It had only been two months since the end of the war. Two months since he and Dean met back in their family home in Lawrence, Kansas after three years fighting on two different fronts, in two different countries.

Both of them had enlisted, but Sam had spent most of his time in London while he was deployed, helping British Intelligence. Dean had clawed his way out of Normandy, and later, out of the Ardennes—the last offensive before the end.

Their experiences might as well have been worlds apart, but one thing remained the same: it had been three years in which neither brother knew if they’d see each other again.

Now, Sam saw the signs. Dean seemed a bit jumpy, overstimulated, but willing to be here to spend a little more time with Sam before he went back home. Guilt prickled in Sam’s gut.

“I’ve got some work here to finish up, but afterwards let’s go to dinner,” he suggested. “Maybe see a show?”

Dean’s lips flickered at a smile. “You’re burning both ends of the candle. You know that, right?”

Sam opened his mouth to reply, when there was a knock on one of the glass doors—at the entrance to the small building. Their heads turned, and through the open door of his office, they spotted you standing there in the evening light. You wore a wide-brimmed hat on your head and a scarf underneath, wrapped over your hair and under your chin to shield your face. You knocked again with a hand covered by a leather glove, more persistently.

Cocking his head in confusion, Sam stood from his desk and left the room to let you in. Dean hung back and sat on the corner of the desk to wait. He withdrew a cigarette from the pack and a lighter from his pocket as he did so, but he heard you talking with his brother by the door.

“I’m sorry. We’re closed, miss,” Sam informed you.

“It’s still two minutes until closing. At least, according to my watch.”

“…Well, I suppose you’ve got me there.”

“So can I come in? I need to speak to a lawyer.”

“You sure it can’t wait until tomorrow?”

“I’m afraid it can’t, sir.” Your tone was firm, and it more than implied that you wouldn’t be moved. Sam paused then, perhaps to take a steeling breath.

“All right. Come with me, please.”

You later followed behind him through the hallway and into the office. With a lit cigarette between his fingers, his arms crossed, Dean took note of you. He subtly glanced down at your crème-colored blouse, neatly tucked into the long, burgundy skirt (with lipstick to match), your modest, classy heels, and the way you wore your hair. His brows subtly raised. He’d met quite a few girls this week, but he hadn’t seen a lady like you in quite some time.

Should’ve shaved this morning. The thought was accompanied by the way he swiped a subtle hand over his prickly chin.

You gave him a cursory glance in turn, and offered a polite, “Hello.”

He stood from the desk and switched his cigarette to his other hand, so he could shake yours.

“Hey there. Dean Winchester,” he said. He offered a smile with no small amount of charm. “Pleased to meet you…”

You dutifully gave him your first name only. He found that a little strange, but you soon slipped your hand out of his and focused on the nameplate on the desk, followed by Sam himself.

“So you’re brothers,” you realized. “Do you work together?”

Dean scoffed. “Nope, I’m just here to distract him.”

Sam tossed him a sidelong glance. There was a subtle edge of bitter truth in there somewhere, and you didn’t seem to miss it. You looked between the two men, a hint wary.

“Well, as I said, I’m here to speak to the solicitor,” you said.

“That would be me,” Sam nodded. He went to his desk and sat down behind it, gesturing for you to do the same in front of him. You obliged him, smoothing your hands down your skirt once you were seated. “How can I help you?”

You met his eyes with a directness that surprised him a little.

“I want to divorce my husband,” you said.

To say it shocked the room would be an understatement. Behind you, Dean gave his brother a pair of raised brows. Sam didn’t allow himself to react too much in order to remain professional, but he still tilted his head, blinking, before he focused on you again.

“What’s your husband’s name?” he asked.

“Michael. Michael Milligan.”

“Why do you want a divorce, Mrs. Milligan?”

Here, your gaze fell to the folded hands in your lap.

“I have reason to believe he’s been unfaithful,” you quietly replied.

Once again, there was a pregnant pause.

“I’m sorry to hear that,” Sam said. His sympathy was genuine, because he could see the way you’d hesitated to say the words, like they embarrassed you, shamed you, and saddened you all at once.

“But I have to ask,” he added, “do you have proof?”

Dean glanced his way, his brow raising once again. Sam knew what he was thinking, just as he saw how you frowned as well. But there was a reason why he asked, and it wasn’t to be unkind.

You sighed. “What kind of proof?”

“Pictures. Letters. A witness. Something of legal standing that we can use as leverage and as grounds to grant you a divorce, whether he wants it or not,” Sam said.

You let out another heavy breath through your nose. “No, I don’t have anything like that.”

“Then what makes you so sure he’s steppin’ out?” Dean chimed in. By now he was leaning against the wall, off to the side where he could smoke with the window cracked open. It let in the sounds of cars and distant honking, people traversing the sidewalks.

You turned in your seat to give him a tight look. “If you must know, there’ve been…signs. I won’t trouble you with the details, but I’m sure.”

You met Dean’s gaze, and then Sam’s firmly.

“So will you help me?” you asked him. Sam nodded.

“Yes, I’ll look into your husband and try to find some evidence of his…extracurricular affairs.”

Your lips pursed. “And how long will it take?”

Since you were being so direct, Sam levelled you with honesty.

“It may take time,” he said. “Realistically, we’re looking at months, even after I find what we need… It would be easier to legally separate.”

You had been slowly deflating the more he spoke, but now your expression became stony.

“Mr. Winchester,” you began. “I don’t want to just be separated. I don’t want to live in our apartment, let alone share his bed or wear his last name.”

Despite your best efforts, your voice began to shake. Tears welled up and stung in your eyes.

“I don’t want anything from him, other than his signature on the damn papers,” you said. “The case is that I can no longer tolerate that man in my sight, much less in my life. Will you help me? Or should I look for another lawyer who will actually do his job.”

Sam and Dean shared a glance. For his part, Dean couldn’t remember the last time he heard a woman curse. Despite your outburst, the tears clinging to your lashes stirred both men.

“I understand, Mrs. Milligan,” Sam said. “I’ll help you. Don’t worry.”

He began to look for his handkerchief, but you retrieved one of your own from your purse and quickly dabbed at your eyes, sniffling. You were embarrassed.

“What about your fee?” you said, withdrawing your checkbook. “I, um…I have a little money stashed away. I’ve always worked, you see.”

Sam nodded and went over what his rate would be going forward. Once the two of you came to an agreement, you signed the first check right then and there, even though he felt bad for even taking it from you.

You were still sniffling, and twice you dabbed under your eyes to make sure your face was dry. When you handed over the check, your hands shook, just a little. Sam wouldn’t tell you that he discounted his usual rate.

Again, he mentioned that he would need some time first to investigate your husband and begin collecting evidence for your case. He asked you for any documents you could safely bring him of your finances, for example. You agreed to do an investigation of your own.

“Just be careful,” Dean cautioned. He was getting an idea of what kind of man your husband was, but Dean couldn’t be too sure of what the man was capable of. He’d hate to hear of a girl like you getting hurt over a few papers.

Dean put out the bud of his cigarette on the ashtray lying on the windowsill. He pushed off the wall to approach where you and Sam were getting to your feet. You gave Dean a nod of acknowledgement.

“I will,” you agreed. “Thank you both. I’m sorry I’ve taken up so much of your time, but I’ll be heading home now.”

“Did you take a bus or a taxi?” Sam asked.

“Oh, I walked,” you replied, and you checked your watch as you gathered up your purse. You headed for the coatrack, but Dean got there first, helping you into your beige wool coat. It went nicely with the burgundy you had on, namely on your painted lips.

“Thank you,” you said to him, but you still didn’t smile. You were a hint demurer now. It seemed with Sam’s promised help, the fire had dimmed behind your eyes and your tongue.

“How about I give you an escort, make sure you get home okay?” Dean found himself offering. “It’s getting pretty late on a Friday.”

Sam shot him a knowing look, but Dean ignored him, instead focusing on your face.

You hesitated. “It’s a bit far though. Out of your way, I’m sure.”

“All the more reason that you shouldn’t go it alone at this time of night,” he argued.

You considered his offer, and him, with a quick perusal. You seemed to be judging for yourself if he was trustworthy. Dean kept his posture straight, yet relaxed. Maybe he’d liked what he saw the moment he took you in, but after hearing your situation, he felt for you. It really was just an honest offer to walk you home.

“Where did you serve?” you asked. “The Army, the Navy, or the Air Forces?”

The question took him off guard for a beat, but he answered you.

“The Army,” he replied.

“Your rank?”

“I was a sergeant, ma’am.”

You looked at him a little more shrewdly, then you relaxed.

“I might’ve guessed,” you said. “All right, Sergeant. Let’s go then.”

You buttoned up your coat and turned to leave the office. Dean shot his little brother a raise of his brows and a what do ya know? kind of smile. He grabbed his dark brown jacket and hat and followed you out.

Sam’s smile was more reserved, with a shake of his head. He closed the door behind you and Dean and locked it. He still had some work he wanted to finish before tomorrow, and Dean’s little show of chivalry would give him time to do it.

Dean had his hands in his coat pockets as he walked with you down the long city sidewalk. Night had drawn into the November sky, but with all these lights, he couldn’t see many stars. It was also cold as all hell. The frigid wind slapped at him every time they turned the corner of a building, snapping right into his bones.

Still, he supposed there was a kind of attractiveness to the city at night. The stores and their signs were all lit up gold and other neon colors. Couples and families walked together, all done up nice for wherever dinner reservation or movie they were trying to get to. It begged the question of what your husband was doing right now if he didn’t notice his wife out at this time of night.

“Where’s your husband tonight, if I might ask?” said Dean.

You shot him a look, reading between his lines.

“He claims to be working late virtually every night of the weekdays,” you said, “but he usually comes home stinking of alcohol.” Your eyes dimmed, even with the pretty lights shining in them. “He was in the Army as well. A corporal. He’s had a hard time adjusting to being back home, and I know that… He doesn’t sleep very well. And do you know, he had a hard time finding work for a while too. Luckily, he has his father’s business to fall back on.”

Dean tried not to show how much your words resonated with him. He didn’t think it a good thing to have common ground with your husband, if he was the kind of man you said he was.

“Yeah? What’s his business?” he asked.

“He manages a meat production plant, of all things,” you said.

“Ah, located in the Meat Packing District, I presume?”

“You’d presume right.”

Dean nodded. “I get it. I inherited the family home back in Lawrence. I just need to figure out what’s next.”

“Lawrence?”

“Kansas.”

“Oh, the Midwest,” you inclined your head. “What’s it like there?”

Dean scoffed. “Dusty.”

You almost laughed at that. At least it earned him your first smile of the night.

“Do you have an idea of what you’ll do for work?” you asked.

Dean chuckled. “Not just yet. Didn’t plan that far, you know?”

“Why not?” you asked.

“Hmm. Guess I didn’t see the point,” he replied with a mild shrug. It hid a deeper, darker well inside him. The part of him that hadn’t thought he’d make it back home after the war.

You turned to him then, and you saw it behind his eyes. The two of you walked in silence for a little while as the neighborhood blocks began to shift and change, becoming somewhat quieter, more residential. Dean put himself between you and the sidewalk when a taxi zoomed by too close to the curb, resting a hand on the small of your back for protection.

Part of you trilled inside at the small touch, but you immediately beat that reaction down. Dean Winchester was an attractive man, to be sure. His hair was a lighter brown than his brother’s, and shorter too. He had an air of roguishness about him, even though he’d been perfectly pleasant so far.

But by the way he eyed you when you came into the law office, you had a strong feeling he was a flirt. You had no room for that in your life, and not only because you were still a married woman.

Yet, there was something about him that…well, made you curious.

“I was a nurse,” you said eventually, earning his attention. “I was there when they liberated Paris.”

Dean turned to you with newfound interest lighting his green eyes. “You were at Normandy.”

You nodded. “For a while. Almost a year before D-Day.”

Dean let out a short, if humorless chuckle, running a hand through his hair.

“Well, that’s where I was. At that time, at least,” he said. You gave him a similar look; respect, and perhaps finding a kindred spirit.

“I did what I could do before, during, and afterwards,” you said. “I think that’s all we can do now, Mr. Winchester.”

“Call me Dean,” he said. “If you like.”

A second smile almost tugged at your lips. You nodded in agreement.

“Dean,” you said.

In another ten minutes, he was walking you up to your porch at your apartment building. You travelled up the four small steps, while Dean stopped at the second one. For the first time, you had the vantage point above him as you turned on your heel to face him. You were about to thank him when he shook his head, scoffing.

“This guy must be dumb, deaf, and blind, sweetheart,” he said.

Your face warmed in a blush, and you gave a rueful smile when you realized what he meant. He was looking up at you like someone who couldn’t understand your plight. You knew the feeling.

“That’s kind of you, but you don’t have to do that,” you said.

His brows furrowed. “Do what?”

“Try to make me feel better,” you said, scuffing the toe of your sensible heels against the brick platform. Dean crossed his arms.

“Why not?” he asked.

“Because the fact of the matter is, Sergeant, words don’t move me anymore.” You picked up your gaze from the ground, and you met his. “Flattery is just a pretty way of lying, and I’ve grown to really, truly hate lying.”

It took him a moment, but Dean nodded.

“I guess that’s fair,” he said. He had to stop himself before he proved your point with a smart word on your pretty smile. Although, it wouldn’t have been a lie. He tipped his hat up. “Goodnight then, Mrs. Milligan.”

You stopped him from leaving with just your voice.

“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.

He gave you a charming grin and a more casual soldier’s salute. Then he stuck his hands back in his pockets, turned on his heel, and began to walk back the way he came. You couldn’t help but watch him go for a second or two. His legs were slightly bowed under his slacks, you noticed.

With a blush, you shook your head to rid yourself of those silly thoughts. You closed the door.

That night, Michael came home late, as usual—this time at two in the morning. He reeked of alcohol, also per usual, but this time when he rolled over towards you in bed to say goodnight, you stiffened. He also smelled like a woman’s perfume. Expensive stuff.

This was one of those signs you hadn’t wanted to tell Sam Winchester. Frankly, it was crude and embarrassing.

“Sorry it’s so late, darling. Got held up,” he said, kissing your shoulder through your nightgown. His fingers played with the ends of your hair while you laid facing away from him.

You squeezed your eyes shut. You were fighting every instinct you had inside you that wanted to recoil from his touch and bolt out of the bed. When just a few months ago, his touch was all you craved, almost desperately so.

“Where were you?” you asked. Somehow, you kept your voice steady and calm. “You weren’t at the office all this time.”

“Had a couple of drinks with the guys after,” he said with a shrug. “Sorry. The night got away from us, but, uh…I’ll be home on time for dinner tomorrow.”

With your back turned to him, you were able to roll your eyes.

“What’d you make tonight, outta curiosity?” he asked.

“Egg salad sandwiches,” you replied flatly.

“Hmm. No real loss there then.”

Your teeth clenched. “If I thought you were actually going to be home when you said you would, maybe I would make a rump roast with all the fixings.”

Michael paused, but then, he grasped your shoulder, slowly turned you around in the bed until you were facing him. His face was sterner.

“Excuse me?”

You remained quiet. Your gaze travelled downwards, avoiding his.

Michael huffed, shaking his head. “Sometimes you got a real mouth on you. One of these days, you just might regret it.”

He turned his back on you, laying on his side. You did the same while trying to stem your tears.

When did this become your life?

AN: Oof, sorry for all that angst at the end there, but I hope you liked the first chapter! Did you enjoy soldier!Dean and soldier/lawyer!Sam? Do you want to find a dark alley for Michael yet? 😅

And are you ready for what's coming up next? 😘

Next Time:

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?”

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