fallingforfictionalmen - Tumblr blog

fallingforfictionalmen · 5 months ago

Text

omggggg okay I took a break from work to read this bc im so behind on this series and I cannot WAIT for the rest AHHHH

『 chapter three 』

꧁ summary: you and dean finally make it to the blue orchid. feels like you’re closer to some answers… right?

꧁ warnings: jealousy from both parties, dean and reader get offered a proposition, cussing, harrington is a dick, speakeasy, protective!dean, reader and dean are left speechless, tension, fluff if you squint, slight sexism, I actually laughed writing this chapter.

꧁ word count: 6.4k

series masterlist previous chapter next chapter

The Blue Orchid wasn’t just a speakeasy—it was a whole different world hiding in plain sight.

From across the rain-slicked street, it looked like nothing more than a bakery closed for the night. The windows were dark, the awning sagging under the weight of the rain, water dripping steadily onto the sidewalk. Nothing about it screamed illegal booze and jazz-fueled debauchery. But every time the door cracked open, even for a second, the truth slipped out.

A low hum of jazz filtered through the gap, teasing at something bigger and louder, before the door shut again, sealing it all away. You and Dean hung back in the shadows, watching as well-dressed men and women leaned in close to the bouncer, murmuring a password before disappearing into the night’s best-kept secret.

Dean let out a low whistle, shifting beside you. “Classy joint,” he muttered, tugging at the collar of his borrowed shirt.

You smiled. He looked damn good in it. Not that you were about to say that out loud but the way he kept messing with it, like the fabric was trying to choke him, made it clear he wasn’t comfortable.

You barely heard him. You were too focused on the entrance as Dean exhaled sharply and adjusted his shirt, the movement catching your eye. The damn thing fit him almost too well, sharp in all the right places, making him look like he actually belonged here. It was annoying. Unfair, really. You swallowed hard and looked away before your thoughts could go places they shouldn’t.

“This is a bad idea,” Dean muttered, voice low.

You smirked. “You say that like we ever have good ideas.”

Dean shot you a look, half exasperated, half yeah—fair point, but didn’t argue.

The rain had finally let up, settling into a lazy drizzle, but the streets were still slick, the glow of streetlamps reflecting in puddles that stretched like little pools of molten gold. You tugged your coat tighter around yourself. “Alright. What’s the plan?”

Dean exhaled, eyes scanning the entrance. “We get in, we find Harrington and we get some damn answers.” His gaze flickered over you, his expression unreadable, lingering for just a second too long.

You could feel the way your dress still clung to you in places, damp from the rain, and if you weren’t already warm, that look might’ve done it.

Dean looked like he was about to say something else, maybe something about how you looked, but instead, he just cleared his throat and shifted his weight. “We just gotta blend in,” he said, like it was that simple.

You smirked, eyes trailing over him. “Guess you can clean up nice. Almost didn’t recognize you without the flannel and grease stains. Think you can handle it?"

Dean scoffed, smoothing a hand over his damp shirt. “Sweetheart, I could make a burlap sack look good.” He shot you a cocky grin, eyes glinting. “And I was born to handle it.”

Cocky asshole. You had definitely seen Dean in a lot of situations. Covered in blood, grease, dirt—half-dressed, even. But this? This almost had you drooling.

The rain had done a number on both of you, sure, but Dean? He somehow made soaked to the bone look like something out of a damn fantasy.

His crisp white undershirt was clinging to him in all the right ways, the thin fabric damp enough to be just a little too revealing. It stretched over his broad chest, sticking to the hard lines of muscle beneath, and with the way the dim light hit him, you could just barely make out the definition of his torso through the fabric.

And the suspenders? Jesus.

They ran over his shoulders, snug against his frame, emphasizing just how solid he was. The rain had darkened them slightly, making them contrast even more against his white shirt, which was practically plastered to his skin at this point.

He had rolled his sleeves up to his elbows at some point, exposing strong forearms, the hint of veins standing out against his skin. If you weren’t already overheating from the situation, that alone might’ve sent you into a coma.

Dean ran a hand through his damp hair, pushing it back—which only made things worse. Little droplets of water caught in his lashes, his jaw was tight with focus as he glanced around. And then when his gaze flicked back to you, you knew you'd been caught. It was way too obvious that you had been staring.

“See something you like, sweetheart?” he teased, one corner of his mouth lifting.

Shit. You tore your eyes away, pretending to adjust your dress like that had been your plan all along. “Nope,” you lied, voice a little too high, a little too quick.

Dean chuckled, clearly amused. “Sure about that?”

No. Not even a little. But you’d be damned if you were going to admit it.

So you ignored Dean and how downright unfair he looked and you focused on the task at hand, stepping up to the entrance of the speakeasy. The only thing standing between you and all of that? The bouncer.

He was a broad-shouldered guy in a sharp suit, arms crossed, expression bored as he leaned against the doorframe.

His gaze barely flickered when he saw Dean. But when his eyes landed on you? Oh, that got his attention. His expression shifted, his posture straightening just a little, and the shadow of a smirk creeped in. “Go on in, doll,” he said smoothly, already stepping aside for you.

Dean moved to follow, but before he could take a step, the bouncer’s hand came up, stopping him cold. His brows lifted slightly, unimpressed. “Password?”

Dean’s entire body stiffened. The fuck? He shot you a sharp look like are you seeing this shit? before turning back to the bouncer. “You didn’t ask her for a password.”

The bouncer just shrugged. “Didn’t have to.” His eyes flicked back to you, and Dean’s jaw tightened.

You, meanwhile, had to physically bite back a smile. Dean Winchester, Mr. Confident, Mr. I was born to handle it, getting held up at the door like some random nobody? Oh, this was rich.

But before Dean could properly explode over the insult, you stepped in, looping an arm through his and flashing the bouncer your best I’ve got this smile. “He’s with me,” you said sweetly. “My husband.”

Dean inhaled sharply, and you felt him go rigid beside you. You didn’t need to look at him to know his expression was priceless.

The bouncer’s brows lifted, glancing between you two like he was reevaluating the entire situation. After a beat, he gave you a slow nod, then finally stepped aside. “Go on in, then.”

You tugged Dean through the door before he could say something smart, feeling the heat of his glare burning into the side of your face. As soon as you were inside, swallowed by the warmth of the speakeasy, he leaned down, voice low and grumbly “Husband, huh?”

You shrugged, still not looking at him. “Seemed like the easiest way to get your grumpy ass inside.”

Dean huffed, raking a hand through his damp hair, still bristling over the whole thing. “Could’ve just let me handle it.”

“Oh, yeah? And how was that going? You gonna sweet-talk him into letting you in?” You smirked, finally glancing at him. “Didn’t think so.”

Dean muttered something under his breath, his jaw still tight, and, oh yeah—he was pissed. Pissed that the guy had ignored him, pissed that you’d had to step in, pissed that the bouncer had looked at you like that. But mostly? Mostly, he was still hung up on the husband thing.

Good. Let him soak in it. You, meanwhile, had a job to do.

The second you stepped inside, Dean grabbed your hand. It wasn’t planned. Hell, you weren’t even sure he realized he did it. But the moment the door shut behind you, his fingers wrapped around yours like instinct, like he needed to keep you close.

You didn’t pull away but neither did he.

Inside the speakeasy was a whole different universe from the rainy street outside. A grand chandelier bathed everything in gold, light flickered off crystal glasses and the sequins of women’s dresses as couples swayed to the slow, sultry hum of the band. The air was thick with perfume, whiskey, cigars, and laughter mixing within the low murmur of conversations around you.

Women lounged in velvet booths, their dresses clinging in all the right places, red-painted lips murmuring secrets against the ears of men in crisp suits. Gloved fingers trailed over lapels, trailing promises.

And the eyes. You felt them immediately. Men at the bar, men at the tables—watching. Not even subtle about it. Slow, deliberate glances sliding over you, over your dress, the shape of your legs, the rain-damp curls at the ends of your hair. You straightened your spine, but ignored it.

Dean didn’t though. His grip on your hand tightened, his entire body going rigid beside you. He didn’t even look at the men, but you could feel it radiating off him, the way his jaw ticked, his fingers flexing like he was seconds from wrecking someone’s night.

You gave his hand a squeeze. “Focus,” you whispered, attempting to calm him down.

Dean exhaled sharply through his nose, forcing himself to ease up but his hand stayed wrapped around yours. “Let’s just find Harrington,” he muttered, leading you toward the bar.

You barely made it three steps before—

“Oh my, my.” The feminine voice was like honey, smooth as the jazz that filled the room.

You turned around and felt your stomach drop.

A woman was standing near the bar, wrapped in deep red silk, dark hair curled to perfection, lips painted a shade of crimson that could stop traffic. Literally gorgeous. The kind of woman that men spent their paychecks on. The kind that turned heads, made them forget their own goddamn names.

And she wasn’t looking at you, no, no. She was looking directly at Dean.

Dean tensed the second she spoke, his grip on your hand loosening as his attention snapped toward her.

And, okay, yeah—you saw it. The way his eyes flickered, just for a second, taking her in. She was stunning, after all, wrapped in deep red silk that clung in all the right places, the kind of woman who walked into a room and made it her own. And she knew it.

“Well, aren’t you a sight,” she purred, trailing a gloved finger along the collar of Dean’s shirt, her touch light and slow.

Dean didn’t move away. Didn’t pull back. His lips only parted slightly, like his brain was still catching up, trying to process the attention. And then—

A hand brushed against your waist. But it wasn't Dean's. “Looks like we both found something interesting tonight,” a voice whispered near your ear, smooth and self-assured. The kind of voice that belonged to a man who never heard the word no.

Your stomach twisted. But before you could jerk away, before you could so much as breathe—Dean moved. His grip on your hand vanished and his entire arm came between you and the man, shoving him back without hesitation.

“Don’t,” Dean said, voice sharp, cutting through the warm haze of the speakeasy like a blade.

The man, tall, well-dressed, and absolutely loaded if you had to guess, raised his hands, laughing like it was all just a misunderstanding. “Relax, pal. Just appreciating the company.”

Dean’s nostrils flared and your heart pounded.

What the hell was the deal with people in the 1920s?

And then, because apparently the universe was determined to test him tonight, the woman in red trailed her finger along Dean’s jaw, her nails dragging lightly over his stubble. “Mmm, don’t tell me you’re taken, handsome.”

Dean still didn’t look at her. Didn’t so much as acknowledge her, because his focus was on you.

His green eyes locked onto yours, dark, intense, and unreadable. Something burned beneath the surface, something sharp and possessive, something he wasn’t saying but goddamn, you could feel it. He was definitely holding something back.

But then Dean reached for you and wrapped his arm around your waist, pulling you against him, pressing your body flush against his, leaving no space.

Your breath hitched just as Dean looked down at you. “She’s with me.” Dean’s voice was low and firm, leaving no room for argument. But instead of backing off, the man and woman just… smirked. At each other. Like they knew something you didn’t.

And your stomach twisted, and judging by the way Dean’s tight smile dropped and his grip tightened on your waist, he felt it too.

“Oh, we know,” the man smirked, taking a slow sip of his whiskey, eyes gleaming as they flicked between you and Dean, slowly, like they were measuring something.

The woman in red tilted her head, clearly enjoying whatever little game this was. Then she smiled.“It’s obvious,” she said, voice dripping with amusement.

Her gaze slid over Dean first, drinking him in—his broad frame, the way his shirt clung to his strong shoulders. “You,” she purred, “look like something carved from stone. Strong, striking—devastatingly handsome in a way that makes women stupid.”

Dean blinked, caught off guard for half a second. But then her attention shifted. Right onto you.

“And you…” She took her time looking you over, letting her gaze drag over every detail—your rain-damp dress, the way your hair curled at the ends. “Soft and sharp, all at once. Absolutely gorgeous and sexy.”

You almost choked on your own saliva. Okay. Okay. You’d been flirted with before. Hit on by men who thought a wink and a lazy grin would get them somewhere. But this? This was different. This was a woman who looked at you like she wanted to ruin you.

Dean’s fingers twitched against your waist and the woman hummed, clearly pleased by the tension rolling off you both. “The two of you together?” She exhaled, shaking her head like it was almost criminal. “Now that is something special.”

The man beside her smirked, setting his drink down with a soft clink. “Which is exactly why we had to say hello.” He leaned in slightly, gaze flicking between you and Dean like he was inspecting a fine bottle of whiskey. “See, we’ve been looking for… company.”

Your brain fucking short-circuited and Dean’s whole body locked up.

The woman in red smiled, all slow confidence and dark amusement. “Can you blame us?” Her fingers trailed along Dean’s sleeve before shifting her attention back to you. “You’re both so hot and all that tension…So delicious…” She sighed, like it was some great, tragic thing. “Such a waste if the night ended with just the two of you.”

You just stared. Words? Nope. They were gone. Not a single one left that could fly out of your mouth.

Dean cleared his throat, looking like he wanted to combust on the spot. “Uh.” He blinked, still trying to catch the fuck up. “Appreciate the… offer.” His voice was tight, edged with something dangerous. “But we’re good.”

The man lifted his glass with a knowing smile. “Shame.”

The woman in red sighed dramatically, but there was amusement in her eyes. “If you do change your minds…” She reached into the bodice of her dress, because of course she fucking did—and pulled out a small card, slipping it onto the bar. “You know where to find us.”

Neither you nor Dean moved to take it. The couple only shared one last smirk before turning back to the bar, already shifting their attention elsewhere, like they hadn’t just sent both of you into a minor fucking crisis.

You exhaled sharply, trying to process what the hell just happened. You didn’t answer right away—mostly because your brain was still trying to reboot after what just happened. But Dean was still tense beside you, his arm still lingering around your waist like he hadn’t quite convinced himself it was safe to let go yet. You weren’t exactly complaining, considering your legs still felt a little shaky.

Your eyes flicked toward the bar, where the couple had already moved on, laughing softly, their hands all over each other like they hadn’t just invited you into their goddamn bedroom.

Holy shit. You and Dean just got invited to go have a foursome? Wait was that even a legitimate term? You shook your head, trying to shake out all the mental images of you and Dean finally—

Dean scrubbed a hand over his face, muttering something under his breath that you were pretty sure included son of a bitch and what the actual fuck.

“So… we just got propositioned.” You finally found your voice, not knowing what else to say.

Dean let out a sharp, humorless laugh. “Yeah. No shit.”

You turned to look at him and his mouth was still slightly parted, like he couldn’t believe what had just gone down.

But then his eyes met yours. And for a second—just a second—you thought about what the woman had said. ‘all that tension.’ Like it was obvious. Like it was something anyone could see.

But Dean exhaled roughly, like he was trying to shake the whole thing off. “Let’s just—let’s find Harrington, get what we need, and get the hell outta here.”

You nodded, but as you stepped away, Dean hesitated. His hand brushed yours for half a second, a ghost of a touch. Then it was gone, replaced with nothing but the phantom heat of his fingers, the weight of what had just happened settling in your chest like a goddamn brick.

You swallowed hard but didn’t look back. Even as you moved deeper into the speakeasy, past tables lined with half-smoked cigars and whiskey glasses smudged with red lipstick, you could feel it.

The way Dean was still looking at you. The way your skin burned under his gaze. Dean’s hand finally dropped from your waist as you reached the far side of the room, but damn if your skin didn’t still feel the ghost of his touch. Like your body hadn’t quite gotten the memo that he’d let go.

You took a breath, forcing yourself to focus. “See him?”

Dean rolled his shoulders, shaking off whatever the hell had just happened. His gaze swept over the crowd, before— “Got him.”

You followed his line of sight. And near the back of the room, tucked away at a private table like he owned the whole goddamn place, sat him.

Vincent Harrington.

Mid-fifties, graying hair slicked back, a suit so well-tailored it probably cost more than most people made in a year. He had a half-empty glass of scotch in front of him, fingers tapping idly against the rim like he had all the time in the world. His posture was relaxed, effortless—like a man who didn’t worry, because he never had to. Like a man who always had the upper hand.

Your stomach tightened.

Dean shot you a look. “You ready for this?”

You let out a slow breath, steadying yourself. “Not like we have much of a choice.”

His smirk was there, but it was tight, stretched thin over something sharper. “That’s the spirit.”

Together, you wove through the crowd, slipping between dancers and drunk men too lost in the haze of whiskey and perfume to notice. The scent of cigars thickened as you neared the back of the room, where the lighting was dimmer, the air heavier.

Harrington didn’t even glance up—didn’t have to until Dean pulled out a chair and dropped into it like he fucking owned the place. You took the seat beside him and rolled your eyes at his dramatics.

Harrington finally acknowledged your presence after a few seconds. He leaned back, fingers lazily swirling the amber liquid in his glass before lifting his gaze. His expression barely shifted, but the unimpressed arch of his brow said enough. “And you are?”

Dean smiled, slow and sharp. Not his real smile. The other one. The one that said, I know exactly what kind of man you are, and I don’t give a shit.

“Names don’t matter much, do they?” Dean said, his voice smooth as he settled into his chair, like he wasn’t at all phased by the weight of Harrington’s gaze. “Not when we’re here to talk business.”

Harrington studied him, his expression unreadable, then turned his attention to you. His eyes lingered a second too long, assessing, calculating.

You held his stare, unwavering, refusing to shrink under the scrutiny.

And he smirked. “Business, huh?” he murmured, tipping his glass slightly, watching the scotch swirl. “And what exactly do you have to offer?”

Dean’s posture didn’t change, but you felt it, the way his shoulders went rigid, the way his jaw set just a little too tight. Like he already didn’t fucking like where this was going.

“Someone told us you can get us home.” You spoke before Dean could.

Harrington didn’t so much as blink. He only lifted his glass, taking a slow sip of his scotch before setting it down with a soft clink. His gaze drifted over you calmly, assessing, before the barest hint of amusement tugged at the corner of his mouth.

“Home?” he repeated, rolling the word around like he was savoring the taste of it. “Afraid I don’t know what you mean, darling.”

Liar.

Dean shifted beside you, but you barely noticed. Your eyes had caught something else—something small, something subtle, but impossible to ignore.

A pin. A small, polished insignia, resting neatly against the deep navy of Harrington’s lapel.

Your pulse spiked seeing it. That symbol—you knew that symbol. You felt your stomach twist, heat prickling at the back of your neck. He wasn’t just some rich bastard throwing money around—he knew things. He had access to things. Of course he did.

You leaned forward slightly, expression hardening. “Cut the shit.”

Dean’s head snapped toward you, startled at your tone and Harrington’s brows lifted just a fraction, the first real crack in his stone cold demeanor.

But then, slowly, his gaze followed yours. Down to the pin. For a long second, no one spoke.

Then Harrington exhaled a soft chuckle, shaking his head as he lifted his drink again. “Well,” he mused, eyes glittering with something sharper than amusement. “Not just a pretty face after all.”

Your fingers twitched against the tabletop, fighting the urge to snap back at him, but you held your ground, keeping your voice steady. “That’s a nice accessory you’ve got there,” you said coolly. You drummed your fingers lightly against the wood, gaze never leaving his. “Didn’t know they were letting just anyone wear their crest these days.”

Harrington smiled, slow and knowing. “So,” he drawled, setting his glass down, “what year are you from?”

Your breath hitched and Dean tensed beside you, so still you could feel the shift in the air between you.

Harrington smirked. “Ah,” he murmured, watching your reactions like a man who already knew all the answers. “That’s what I thought.”

Dean recovered first, his voice edged with suspicion. “How the hell do you know that?”

Harrington let the question settle for a moment, the quiet stretch of time dragging like he was letting the weight of it sink in. Then, with an almost lazy motion, he glanced down at the pin, his fingers brushing over it like a habit, a reflex.

“You two stick out like a sore thumb, you know that?” he said finally, his tone casual but his eyes sharp. He wasn’t just making conversation—he was studying you, pulling you apart piece by piece.

Dean’s shoulders squared, his expression hard, but Harrington didn’t even look at him. His focus was on you.

“You especially,” he continued, amusement curling at the edges of his words. “No woman in this day and age would dare speak to a man like me the way you just did. Not unless she had a death wish. Or…” He tilted his head slightly, eyes narrowing. “She wasn’t from this day and age at all.”

Your fingers twitched against your knee, but you didn’t break eye contact. You weren’t going to give this bastard the satisfaction of rattling you.

“And him?” you asked, jerking your chin toward Dean. “He sticking out too?”

Harrington hummed, finally sparing Dean a glance.

“Less obvious, but yeah,” he admitted, swirling his scotch in his glass. “Maybe it’s the way he carries himself. Not stiff like a businessman, not polished like a politician. There’s something else there—something rough around the edges. And those eyes…” He smirked faintly. “Like a man who’s seen things no one in this time should have seen.”

Dean’s jaw tightened, his patience wearing thin, but he held his tongue. For now.

Harrington set his drink down, lacing his fingers together as he leaned forward slightly. “But it’s you, darling, that really gives it away.” His eyes flicked back to you, sharp and knowing. “Because you know what this is.” He tapped the pin on his lapel. “And no woman in 1925 would know that. Hell, even most men in this world wouldn’t. The Men of Letters keep their secrets close.” His smirk widened slightly. “They don’t take kindly to outsiders. And they sure as hell wouldn’t let a woman into their little club.”

Dean rolled his eyes at that, his knuckles pressed against the table like he was about two seconds from decking the guy. But you, you just stared at Harrington, your mind working a mile a minute.

Because he was right. You weren’t Men of Letters. Not exactly. But you knew them. Knew their symbols, their secrets, their history. You’d walked through their halls, read their books, fought their battles, even if they never would’ve let someone like you through their doors back then.

Harrington watched the realization flicker across your face and chuckled. “See? You don’t belong here,” he said smoothly, like he was reading your mind. “And lucky for you, I do know how to send you home.”

Dean’s gaze snapped to him, eyes burning with barely restrained frustration. “Then start talking,” he growled.

But Harrington just smiled. “Not so fast,” he murmured, reaching for his drink again. “I could help you. But the question is… why the hell should I?”

Dean leaned forward, voice low, edged with something lethal. “We’re not asking.”

Silence. A long, tense moment stretched between the three of you, the distant laughter and clinking glasses fading into the background. Harrington chuckled. Like this was all a fucking joke. His smirk was slow and knowing, like a cat playing with a cornered mouse. He swirled the whiskey in his glass before setting it down, his fingers tapping a lazy rhythm against the wood. His smirk was damn near lazy, eyes flicking between you and Dean like he was sizing up something amusing, something obvious.

Dean, meanwhile, looked about two seconds away from throwing a punch. His fingers drummed against the table, his patience hanging by a thread. “You got something to say, or are you just wasting our time?”

Harrington hummed, swirling his scotch. “You two really are something.” His gaze slid over to you, lingering just long enough to make Dean’s scowl deepen. “That chemistry—you can’t fake that.”

You folded your arms. “If you’re done playing matchmaker, maybe we can get to the part where you actually help us.”

He chuckled, clearly entertained. “Patience, darling.” He reached into his jacket pocket, pulling out a small card, but instead of handing it over, he just twirled it between his fingers. “This man owes me a favor. You go to this address, tell him Vincent Harrington sent you, and he’ll help.”

Dean held out his hand expectantly, but Harrington didn’t give it up just yet. He flipped the card between his fingers, dragging out the moment. “You sure you two know what you’re doing?” He flicked his gaze back to you. “Or is this another one of those ‘we’ll figure it out as we go’ things?”

You narrowed your eyes. “Give me the damn card.”

Harrington’s smirk deepened. Instead of handing it to Dean, he extended it toward you, holding it just out of reach for half a second before finally letting it go.

You snatched it from his fingers, jaw tight. “Alright. I’m done with this conversation.” Without waiting for a response, you turned and walked off, not even sparing him another glance.

But as Dean moved to follow, Harrington’s voice stopped him. “Wait a second, son."

Dean turned, already irritated. “Now what?”

Harrington’s smirk was sharp as ever. “Women like that?” He nodded toward you, watching as you disappeared into the crowd. “They don’t come around often.” He took a slow sip of his drink. “You might want to man up before someone else does.”

Dean’s jaw twitched. “Yeah? And what the hell do you know?”

Harrington chuckled. “More than you, apparently.” He set his glass down with a soft clink. “I’ve seen a lot of men let a good thing slip through their fingers because they were too damn stubborn to admit what they wanted.”

Dean exhaled sharply, shifting his weight, suddenly feeling too warm. “Yeah, well, thanks for the unsolicited wisdom, but we’ll be on our way.”

Harrington just gave him a knowing look. “Suit yourself.”

Dean muttered something under his breath and finally turned to catch up with you, hands shoved deep in his pockets.

Because the worst part?

Harrington wasn’t wrong. And that pissed him off more than anything.

You followed in silence, your footsteps barely audible over the distant hum of the city. The rain had stopped, but the streets were still slick, reflecting the glow of gas lamps and neon signs. The air was damp, carrying the scent of wet pavement, whiskey, and cigarette smoke, wrapping around you, lingering.

Dean moved ahead, his shoulders squared, his gaze locked forward as he led you through winding streets, past shadowed alleys and the occasional drunk stumbling home.

The deeper you went, the quieter it became, the sounds of laughter and jazz fading into something more hollow.

Then, finally, he stopped and turned toward a narrow passage barely visible between two brick buildings. It looked like nothing—just another forgotten alley swallowed by the city. But at the very end of it, half-hidden in the darkness, stood a rusted metal door. Dean exhaled, shifting his weight. “This better be it.”

You didn’t bother answering, just nodded as a chill crept up your spine. Dean stepped forward, wrapping his knuckles against the steel and knocked three times.

Erie silence filled the space between you before a heavy clunk sounded and the lock slid open. The door creaked inward, revealing a man standing in the dim light. He looked to be in his late fifties, with wild gray hair sticking up in uneven tufts and deep lines carved into his tired face. His clothes were wrinkled like he’d been up for days, but his eyes were sharp.

He studied the two of you for a moment, then arched an unimpressed brow. “You lost?”

Dean let out a humorless huff. “Buddy, you have no idea.”

The man didn’t react, just leaned against the doorframe, arms crossed over his chest. “What can I do for you?”

Dean squared his shoulders. “Vincent Harrington sent us.”

At that, something flickered in the man’s expression. His gaze lingered on Dean for a second longer before he sighed and stepped aside. “Alright. Come in.”

Dean didn’t hesitate. The second the man stepped aside, he gestured for you to go in first, his hand hovering at the small of your back—not touching, but close enough that you could feel the warmth of it.

You shot him a quick look, but he wasn’t paying attention to you. His eyes were locked on the stranger, his posture tense, protective, like he was ready to throw a punch if this guy so much as blinked wrong.

Stepping inside, you took a moment to take in the space. It was cramped, cluttered with stacks of books and papers scattered across every surface.

The air smelled of ink, dust, and something metallic—magic, maybe. Old and heavy, soaked into the very walls. Shelves lined with jars held strange trinkets, things you probably didn’t want to inspect too closely. A single buzzing lightbulb swung overhead, casting long, shifting shadows.

Dean followed a second later with the door clicking shut behind him.

The man folded his arms and leaned back against a desk, eyeing the two of you with mild curiosity. “Alright. What can I do for you?”

Dean exhaled, running a hand down his face before cutting straight to the point. “We need to get back to our time—2013, to be exact.”

That got the guy’s attention. His brows lifted slightly, and his gaze sharpened as he looked between the two of you. “2013,” he echoed, like he was making sure he’d heard right.

You nodded. “Yeah. And unless this is just a really weirdly themed town, I’m guessing you already know we don’t belong here.”

The man let out a slow breath, tapping his fingers against his arm as he studied you both. “Well, well… you two must’ve really pissed someone off.”

Dean huffed a dry laugh. “Yeah, you could say that.”

The man squinted at you both for a beat longer before asking, “And how exactly did you end up stuck here?”

You and Dean exchanged a glance before you answered in unison, “A witch.”

The man snorted, shaking his head. “Figures.” He scratched at his jaw, eyes flicking between you and Dean like he was weighing just how much trouble you were about to be. “It’s possible to get you back. But it ain’t easy.”

“Shocker,” Dean muttered under his breath. You ignored him, leaning in. “What do we have to do?”

The man sighed, pushing off the desk and pacing a slow circle around the room. “You need a strong enough energy source to rip through time. That’s what got you here in the first place—a surge of raw power. Without something like that, you’re stuck.”

Your stomach twisted. “And where do we find that?”

He stopped, rubbing the back of his neck. “If you’re lucky? There’s a relic—a gold pocket watch that’s been soaking up energy from spells for decades. It’s the real deal, holds enough residual power to punch a hole through time. Problem is, it’s locked up in a private collector’s estate on the other side of the city.”

Dean groaned, scrubbing a hand down his face. “Great. Lemme guess—this collector isn’t just gonna hand it over?”

The man smirked. “Not unless you’ve got a few thousand dollars lying around.”

Dean shot you a look, exasperation written all over his face. “Fan-fucking-tastic.” You exhaled slowly, letting the weight of it settle before you squared your shoulders. “So we steal it.”

Dean blinked at you. Once. Twice. Then a slow grin spread across his face, half amused, half impressed. “Damn. And here I thought I was the bad influence.”

The man shrugged, completely unfazed by the small conversation between you and Dean. “You get me that watch, I can send you back. No watch, no deal.”

You straightened, setting your shoulders like the weight of the whole damn situation hadn’t just settled on them. “Then we better get to work.”

Dean tilted his head, watching you. Despite the tension still simmering between you, there was something else in his gaze—something sharp, flickering just beneath the surface. Admiration? Maybe a little frustration, too, but mostly admiration.

“Alright,” Dean muttered, rubbing his temples. “Let’s break into a rich guy’s house and steal a magic watch.”

You smirked. “Like you haven’t done worse.”

Dean pointed at you. “That’s not the point.”

The guy who had been observing the two of you with thinly veiled amusement, finally cleared his throat. “The estate is heavily guarded. Caldwell—our collector—is a paranoid son of a bitch. Keeps the watch locked up in his private study. And believe me, it’s not just sitting on a desk waiting to be snatched.”

Dean leaned against the desk, arms crossed. “Let me guess—it’s not as simple as busting in and grabbing it?”

The guy huffed a dry laugh. “Not unless you feel like dodging armed guards and a man who collects more than just rare artifacts.” He paused, eyes flicking between the two of you. “Caldwell has… business partners. The kind who make people disappear when they step out of line.”

Dean let out a slow breath. “Of course he does.”

You took a step forward. “So, what’s the plan? How do we get in?”

The stranger reached for a folded sheet of paper and slid it across the desk. A rough sketch of the estate—multiple floors, gated entrances, long hallways, and a grand ballroom that stretched across nearly half the place.

“There’s a gala tomorrow night,” he said. “If you two can get in, you might have a chance to slip away and grab the watch.”

Dean sighed, already knowing the answer. “Looks like we're about to crash the party.”

The guy smirked. “Now you’re getting it.”

Dean dragged a hand down his face. “Alright. So we need a way in, a way out, and a way to grab the damn thing without getting shot.”

The guy tapped the paper. “I know a guy who can forge invitations. They won’t be perfect, but they’ll get you through the front door.”

You glanced at Dean. “That means we need to look the part.”

Dean groaned. “If you make me wear another fancy suit, I swear—”

“But you'll look damn good in it,” you interrupted, grinning.

Dean narrowed his eyes at you, but he didn’t argue. The guy chuckled. “Sounds like this ain’t your first time pulling something like this.”

Dean shrugged. “Let’s just say breaking and entering isn’t exactly new territory.”

The guy nodded. “Then you’ll figure it out. But listen—Caldwell doesn’t play around. If you get caught…” He let the words hang, but the meaning was clear.

You swallowed hard and Dean set his jaw, gaze dark and steady. “We won’t.”

The mysterious man then reached into a drawer and pulled out another folded slip of paper, and pushed it across the desk. “Here’s where you’ll find my guy for the invitations. Get those, get dressed, and don’t get caught.”

Dean snatched up the paper and turned toward the door. “Great. Let’s go commit another felony.”

author’s note:

what can I say, I’m a whore for jealous!dean. I was actually laughing at the couple hitting on dean and the reader. ahh that was my favorite part to write out of this whole chapter, lmfaooo. it was so awkward for them and I love it. told y’all there would be a lot of tropes in this series, haha.

just wait until the next two chapters >:) I’ve been cooking up something that makes me giggle and kick my feet like a teenager. I hope you guys enjoyed this one! plenty more to come!

— requests are open.ᐟᅟ please read request rules.ᐟᅟ

tags:

@freeluigihesbae @aylacavebear @supernotnatural2005 @bettystonewell @lieutenantchaos @bejeweledinterludes @ambiguous-avery @star-yawnznn @exansation @darkrose064 @megara0224 @pressedwater @ladysparkles78 @waynes-multiverse @exansation @darkrose064 @fallingforfictionalmen @jollyhunter @pilotdeanwinchester @kaz-2y5-spn @darling-eos @illicithallways @saturnsooya @miss-marmalade @h8aaz @xo-zeze @kamisobsessed @taleofmanyships @megara0224 @remzywashere (lmk if I’ve missed anyone or if you’d like to be taken off)

If you would like to be tagged please fill out THIS form and I will add you to the list! ❤︎

my works

#dean winchester x reader

113 notes · View notes