#deanwinchester
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lila-lou · 2 days ago
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✨High School Sweetheart - Pt 3✨
Summary: You come face-to-face with a ghost from your past—Dean Winchester. Five years after he vanished from your life without a word, and now he´s here. But neither you nor he are teenagers anymore.
-Listen to "Chance with you"-
Pairing: Dean x Reader
Warnings: 18+ only! Smut, Language, Fluff
Word Count: 9843
A/N: English isn’t my first language, please be lenient. 💙
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The morning sunlight filtered through the thin motel curtains, casting a soft glow over the room as Sam sat on the edge of his bed, waiting for Dean to finish up in the shower. Sam tapped his foot, hands folded in his lap, glancing every so often at the closed bathroom door. He’d noticed Dean’s pensive mood the night before, the way his brother had seemed lost in thought, staring out the window like he was a million miles away. Sam hadn’t pried, but he had a good guess about what was on Dean’s mind—and who.
A few minutes later, the door opened, and Dean stepped out, towel around his neck, looking fresher but still carrying that same thoughtful expression. He barely looked at Sam as he moved to grab his bag, running a hand through his damp hair.
“So”, Sam said casually, crossing his arms, “you’re just gonna keep quiet about it?”.
Dean glanced at him, a bit startled. “About what?”.
Sam gave him a look, raising an eyebrow. “About her”. He let the words hang in the air, watching as Dean’s face shifted from surprise to something softer, almost resigned.
Dean sighed, slinging his bag onto his shoulder and letting out a low chuckle. “You really don’t let up, do you?”.
“Nope", Sam replied, a small smile tugging at his lips. He watched his brother, his gaze steady, waiting for Dean to let him in.
Dean dropped his bag, shaking his head as he ran a hand over his face, still visibly trying to sort through everything that had been on his mind. “It’s… I don’t know, Sammy. It’s been years. I didn’t think I’d see her again, you know? But standing there, looking at her… felt like I was eighteen all over again”. He let out a quiet laugh, the sound tinged with disbelief. “Like nothing had changed”.
Sam nodded, recognizing that rare vulnerability in Dean’s voice. “But things have changed, Dean. You’ve changed. Maybe this time it doesn’t have to end the same way”.
Dean sighed, not answering right away as he tossed his bag onto the bed and started pulling on his jeans, his gaze distant. He seemed to be wrestling with something, that familiar tug-of-war between his feelings and the reality of his life, the job, the constant moving. He didn’t say anything as he shrugged into his shirt and boots, just focused on getting ready, as if he could avoid the conversation by keeping himself busy.
But Sam was already a step ahead, his fingers slipping into his pocket to check that he still had the card you’d given Dean, the card that now had a purpose. Sam glanced down at the small, neatly printed name of your bookstore, the address on the other side, and couldn’t help but feel a small, satisfied smile pull at the corner of his lips. Dean might be stubborn, but Sam knew how to nudge him when he needed it.
Thirty minutes, a pot of coffee, and a stack of bacon and eggs later, Sam finally put his plan into action.
"Alright, take a left here”, Sam said casually, barely looking up as he guided Dean through the quiet streets.
Dean glanced over, a bit confused but following Sam’s instructions anyway. “Didn’t think the library was on this side of town”, he muttered, frowning as he glanced out the window at the unfamiliar neighborhood. “Feels a little… cozy for a library”.
“Oh, it’s a smaller spot”, Sam replied smoothly, keeping his face neutral. “They don’t have a huge selection, but sometimes these places have rare finds, local stuff that doesn’t make it to the bigger branches”.
Dean shrugged, satisfied enough with that explanation as he continued driving. “Well, we’ve checked out stranger places for lore. Long as they’ve got some weird, dusty books, I’m in”.
“Almost there”, Sam replied, suppressing a small smile as he kept up the charade, sneaking glances at the streets to make sure they were heading in the right direction. He couldn’t wait to see Dean’s reaction when he realized what was really going on.
A few minutes later, they arrived at a small, charming storefront with a faded sign above the door displaying the name of your bookstore. Dean pulled to a stop out front, looking up at the sign with a furrowed brow, his hand still resting on the steering wheel as he took in the scene.
“This doesn’t look like a library”, he muttered, suspicion creeping into his voice as he shot Sam a sidelong glance.
Sam just shrugged, unbuckling his seatbelt and giving his brother a perfectly innocent look. “You know, it’s a bookstore. Pretty close. Besides, who’s to say they don’t have something helpful in here? Worth a look, right?”.
Dean’s eyes narrowed, but before he could question it further, Sam had already opened the door and was stepping out of the car, leaving Dean with no choice but to follow.
As they approached the door, Dean’s eyes lingered on the sign, his mind catching up to Sam’s little scheme. Recognition dawned on him, and he shot his brother an incredulous look. “Oh no… you didn’t”, he muttered, realization flashing in his eyes as he put two and two together. He shoved Sam, who only laughed, taking obvious pride in his handiwork.
“Yup, I did”, Sam replied, grinning smugly as he pushed back, his laughter filling the quiet street.
Within seconds, the two were wrestling on the sidewalk, Dean tugging Sam’s head under his arm in a firm hold, trying to keep his brother’s squirming under control. "You little shit!". Sam’s laughter only intensified, and despite his best efforts, Dean felt his own smirk creeping up. They looked like a couple of teenagers, roughhousing on the pavement outside your store.
Just then, the sound of the door opening caught both of their attention. They froze mid-wrestle, Dean’s arm still loosely around Sam’s neck, as they looked up to see you standing in the doorway, arms crossed, an amused smile spreading across your face.
“Dean Winchester”, you said, trying to keep a straight face as you took in the sight of the two brothers tangled up on the sidewalk, “I didn’t realize ‘library’ was code for causing a scene”.
Dean released Sam, clearing his throat as he straightened up, a faint blush creeping up his neck as he shot Sam an annoyed look. “Well, I, uh…”. He faltered, at a loss for words, clearly caught off guard.
Sam, on the other hand, flashed you a wide, unapologetic grin as he straightened up beside his brother, brushing himself off.
Sam’s grin widened, catching the blush creeping up Dean’s neck. He couldn’t resist pushing the moment further. “You know”, he began, eyes sparkling with mischief, “Dean here missed you so much, he insisted we come by first thing in the morning. Couldn’t even wait for a regular library”.
Dean shot him a warning glare, but Sam only continued, his voice dripping with exaggerated sincerity. “I mean, he practically dragged me out of bed just to get here”, Sam added, crossing his arms with a smug grin. “Said it was a top priority”.
Without missing a beat, Dean lunged at Sam, tackling him in an instant as they wrestled yet again, shoving each other around like kids. You stifled a laugh, watching the two brothers tumble and grapple, a whirlwind of limbs, laughter, and grumbled threats.
“You’re dead, Sammy”, Dean muttered, twisting Sam into a quick headlock, though he was clearly holding back, unable to hide the amusement behind his feigned irritation.
“Sure, sure—just don’t choke on how much you missed her”, Sam replied, barely able to get the words out through his laughter as he tried to squirm free.
You finally stepped forward, your arms crossed as you raised an eyebrow, amusement dancing in your eyes. “Alright, you two—my store’s not a wrestling ring. Think you can keep it together long enough to step inside?”.
Dean finally released Sam again, grumbling under his breath as he straightened up and shot you an almost sheepish smile. “Yeah, well… he deserved it”, he muttered, still trying to shake off his embarrassment.
“I’ll be good”, Sam said, though the look in his eyes suggested he’d take any chance he could to push Dean’s buttons.
You held the door open, motioning for them to come inside, and as Dean stepped past you, you could see that the familiar bravado was tempered with something softer, a vulnerability he was clearly trying to keep hidden. For a split second, he caught your gaze, a quiet smile tugging at his lips, and you felt that spark, the one you’d both danced around years ago, still burning there between you.
Inside, Dean shot Sam a warning look, which Sam met with a silent, amused shrug. You caught a quick, quiet exchange between them that spoke volumes—the easy, unbreakable bond of two brothers who knew each other inside and out.
You looked at Dean, tilting your head with a playful smile, your heart beating a bit faster as you let the words roll out slowly. “So… you’re here because…?”. You trailed off, the hint of hope in your voice barely masked. Part of you wanted him to say it—say that he was here to see you, that he was finally ready to pick up where things had left off all those years ago.
But Dean’s face flushed slightly, and he shifted uncomfortably, glancing at Sam as if searching for an escape. “Uh, well… research, actually”, he mumbled, scratching the back of his neck. “We’ve got some… work to do. You know, the usual. Research”. He cleared his throat. “Got anything on ghosts? Creepy old stories?”.
Your heart sank for a second, the thrill of seeing him dimmed by the reminder that he hadn’t come just for you—at least, not entirely. But before disappointment could settle in, memories rose to the surface, memories that made his question hit a little differently.
Ghosts.
Dean had asked you about them before, on a quiet night in your room, long ago. It had been a strange conversation, one that had left you wondering about the life he led, a life he’d always kept half-hidden, wrapped in shadows and secrets.
You remembered that night vividly. You’d been sitting together on your bed, the faint glow of your bedside lamp casting a warm light over the room. He’d looked thoughtful, almost hesitant, as if he were weighing whether or not to trust you with something fragile.
Flashback
The two of you had fallen into an easy silence, comfortable with each other’s presence as you shared your thoughts and laughed about everything and nothing. Then, out of the blue, Dean turned to you, his gaze holding an intensity you hadn’t seen before.
“Hey”, he murmured, his tone soft but serious. “Do you… do you believe in ghosts?”.
The question caught you off guard, and you looked at him, searching his face for any hint of a joke, but he was watching you with complete sincerity, his usual cocky demeanor replaced with something quieter, almost vulnerable.
“I mean…”. You hesitated, not sure where he was going with this. “I’ve never seen one myself, but I guess I don’t see why they couldn’t be real”. You shrugged, offering him a curious smile. “Why do you ask?”.
Dean looked away, his expression flickering with something you couldn’t quite place. “Just wondering”, he said softly, his voice barely above a whisper. “Sometimes… sometimes it feels like there’s more out there than we want to believe”.
His words lingered, filling the room with an almost tangible sense of mystery, and for the first time, you got a glimpse of the world he lived in, a world he couldn’t fully explain, even if he wanted to.
“Have you ever seen one?”, you asked, your voice gentle, as if you could feel the weight he carried just beneath the surface.
He looked back at you, his eyes reflecting something dark and haunted. “More than you’d believe,” he said, the honesty in his voice breaking through his usual guard. And in that moment, he didn’t need to say anything more; you understood that he’d seen things, things that most people couldn’t even imagine.
End of the Flashback
The memory faded, but the impact of that night remained, leaving you with a lingering sense of empathy for him and the secrets he’d always carried. You looked at him now, older but still carrying that same shadow, that weight you’d glimpsed all those years ago.
“Ghost stories, huh?”, you replied, trying to keep your tone light. “I might have a few. This place is full of old legends”. You motioned toward a shelf filled with dusty old tomes and folklore collections. “But if you’re here to find the spooky stuff… I get the feeling you know more about it than I do”.
Dean gave you a faint smile, his gaze softening, a hint of that same vulnerability from long ago flickering in his eyes. “Yeah, maybe. But… it doesn’t hurt to have a second opinion. You know, for research”.
You couldn’t help but smile, the unspoken connection between you reigniting as you led him toward the shelf, your fingers grazing the spines of the old books. “Well, then, let’s see what kind of ghost stories I can dig up for you”, you murmured, a hint of playfulness in your voice.
And as the two of you stood there, flipping through pages of folklore and old legends, you felt that familiar pull, the same quiet thrill you’d felt back then.
Once you’d gathered a small stack of books, Sam quickly took a few, settling himself comfortably into an armchair in the corner, already flipping through one with intense focus. Meanwhile, you lingered beside Dean, the two of you standing in the quiet space by the bookshelves, a sense of old familiarity weaving around you.
You glanced at him, your expression both curious and a touch suspicious, and you mumbled, “Still into that creepy stuff, huh?”.
Dean’s lips quirked in a small, slightly guilty smile as he scratched the back of his neck, clearly trying to brush it off. “Guess you could say it’s… part of the job”.
You raised an eyebrow, tilting your head as you searched his face. “Still haven’t told me what that job actually is, though”, you said, your voice soft but pointed. “Unless ‘weird, dusty book hunting’ really is your full-time gig”.
Dean chuckled, but there was a flash of something in his eyes, a flicker of guardedness mixed with a hesitation he seemed to be trying to shake off. He met your gaze, and for a second, it looked like he was considering telling you something real, something he hadn’t shared with anyone outside of the world he lived in.
“Yeah, well… let’s just say it keeps me on my toes”, he replied, his tone deliberately vague but laced with that familiar charm. He shifted his weight, leaning slightly against the bookshelf as he looked at you, his gaze steady. “You know, keeping things spooky has its… perks”.
You crossed your arms, giving him a skeptical look. “Uh-huh. Perks like what?”.
Dean’s smile grew, a hint of mischief dancing in his eyes. “Like bumping into old friends in cozy bookstores”. His voice softened slightly, the playfulness tempered with something genuine, and he glanced away, as if the words had slipped out without his full permission.
Your heart gave a small, unexpected flutter, and you fought the smile tugging at your lips. “Old friends, huh?”. You let the words hang in the air, the warmth in your tone a gentle acknowledgment of the connection that had always lingered between you both.
He didn’t answer right away, just looked at you, that guarded look giving way to a softer, more open expression. For a brief moment, the years between you seemed to melt away, leaving only the two of you, standing there like no time had passed at all.
Dean’s gaze softened as he licked his lips, the playfulness in his eyes turning into something deeper, more intense. You could feel the air between you shift, the lightheartedness slipping away as a quiet, unspoken tension built in its place. His eyes traced a slow path from your face, lingering there for a moment, before moving down, taking in every detail, every change time had added.
You couldn’t help yourself—you mumbled, barely above a whisper, “Pretty close friends, if I remember right”.
Dean’s gaze snapped back to yours, his jaw tightening slightly, and you saw the hint of a smirk pull at the corner of his mouth. “Yeah”, he replied, his voice lower now, a rough edge slipping in. “Real close”.
You let out a shaky breath, feeling your cheeks flush as you added, “I don’t know about you, but for me, old friends usually aren’t the ones I know like that”. Your voice dropped, a little unsteady but carrying a hint of challenge. “I don’t know how my ‘old friends’ feel… or how they taste… or the sound they make when they…”.
You trailed off, the words hanging heavy between you, and Dean’s eyes darkened, his expression faltering for just a moment as the memory of that night—a memory you both clearly hadn’t let go of—washed over you both. His breathing grew a little heavier, and he took a step closer, his hand grazing the shelf behind you as if he needed something to ground himself.
“Careful”, he murmured, his voice barely more than a whisper, his gaze locked onto yours with a quiet intensity that sent a thrill up your spine. “You keep talking like that, and I might start thinking about all the ways I could remind you”.
You swallowed, heart racing as you held his gaze, the words almost daring you to push further. But before either of you could say anything else, Sam’s voice cut through the moment from the corner of the room.
"Hey, uh—found something. Might want to check this out", he said, his tone overly casual, but when you looked over, you saw the smirk on his face, like he knew exactly what he'd interrupted.
Dean exhaled, glancing away as he tried to regain his composure, the faintest flush still warming his cheeks.
And as he joined Sam to study the book, you knew this wasn’t the end of the conversation—it was only the beginning.
Dean stood behind Sam, leaning over his brother’s shoulder as he tried to focus on whatever ghost story Sam was explaining, but the words were slipping past him. His mind was elsewhere, and no matter how hard he tried to push it away, his thoughts kept drifting back to you. He looked up, instinctively searching for you, and there you were, standing by the bookshelf, watching him with that familiar smile. The moment your eyes met, a flicker of something undeniable passed between you. You bit your lip, and the memory came rushing back, the way it always did, pulling him in without permission.
Flashback
It was late, well past midnight, and the world outside was quiet, bathed in the soft glow of moonlight. Dean slipped quietly through your window, as he’d done every night he could manage since that first time the two of you had been together. He’d gotten good at sneaking out—waiting for his dad and Sammy to fall asleep, carefully avoiding the creaky boards on his way out, and making the short walk to your place under cover of night.
This night was no different. He hoisted himself up, landing softly on the floor, and there you were, sitting on your bed in your pajamas, a book in your lap, completely absorbed until you felt his presence. When you looked up and saw him, your face lit up, that familiar warmth in your eyes making his heart pound in a way he’d never admit.
“Miss me?”, he whispered, a cocky grin playing at his lips as he shut the window behind him, doing his best to keep the noise down.
You rolled your eyes, setting the book aside as you sat up a little straighter. “You’re late”, you teased, though there was no bite in your voice, just quiet affection and a hint of relief that he was there.
He shrugged, crossing the room in a few steps until he was right beside you, his hands stuffed in his pockets, a casual front that barely hid how much he looked forward to these stolen moments. “Had to make sure the coast was clear”, he murmured, his voice softer now. “Didn’t want anyone to catch me sneaking away”.
You smiled, tugging him down to sit beside you on the bed. “Well, I’m glad you made it”. Your voice was barely a whisper, laced with a warmth that made his heart skip a beat. There was something about the quiet intimacy of these nights—just the two of you, hidden away from the rest of the world—that made him feel like he could finally breathe, like he could let down all the walls he kept so carefully constructed.
He kicked off his boots, leaning back against the headboard beside you, close enough that your shoulders brushed.
He glanced down at the book you’d been reading, a mischievous glint in his eyes as he reached over, snagging it from your hands before you could protest.
“So, what’s got you all wrapped up?”, he asked, flipping through the pages with a grin. “Let’s see… ‘Gothic romance, secrets of a haunted castle…’”. His eyebrows shot up, and he gave you a playful, knowing look. “Didn’t take you for the ‘brooding hero in a dark castle’ type”.
You laughed, leaning over to try and grab it back, but he held it just out of reach, clearly enjoying himself. “Oh, come on, Dean. I like a good mystery”, you replied, rolling your eyes but unable to keep the smile off your face. “Besides, I’ve got my own brooding hero sneaking in through my window every night”.
He smirked, finally handing the book back, though he kept his gaze fixed on you, his expression softening. “Guess I can’t compete with haunted castles and dark, mysterious strangers, huh?”.
You tilted your head, catching his gaze, and the playful tone in your voice faded, replaced by something softer. “I don’t know, Winchester”, you murmured, holding his eyes. “I think you’ve got them beat”.
For a moment, the two of you just stared at each other, the teasing atmosphere giving way to a quiet intensity. He looked at you like he was memorizing every detail, his usual bravado slipping away to reveal something raw, something he rarely let anyone see.
“Yeah?”, he whispered, his voice barely audible as he leaned in, his hand reaching up to brush a loose strand of hair from your face. His fingers lingered, warm against your cheek, and you felt your breath catch, the closeness between you charged with an unspoken promise.
You nodded, your voice just as soft. “Yeah”.
He leaned in, his lips capturing yours in a kiss that was both tender and filled with a quiet urgency, like he was trying to tell you everything he couldn’t put into words. His hand slipped behind your neck, pulling you closer, and you melted into him, all thoughts of haunted castles and mysterious heroes fading away. Right now, this moment, he was yours.
Dean’s hand slid down, fingers gentle yet firm as he guided you backward, his lips never leaving yours as he eased you down onto the bed. He hovered above you, his weight carefully balanced, creating a barrier that was somehow both respectful and filled with an unspoken intensity. You could feel his warmth, his presence surrounding you in a way that was dizzying, comforting, and exhilarating all at once.
For weeks now, the two of you had fallen into this rhythm—a careful dance of stolen kisses and whispered words, the quiet intimacy of your secret nights together. He was cautious, holding back in a way that made your heart ache, like he was afraid to let himself want too much, to let himself take this further. And even now, as he hovered over you, his hand cradling your face with such tenderness, you could feel that same restraint, the silent promise to not ask for more than you were ready to give.
But tonight, something was different. There was a hunger in his kiss that you hadn’t felt before, an urgency in the way his lips moved against yours, and you felt your heart pounding. Your hand moved up, fingers tracing along his jaw, slipping down to rest on his chest, feeling the steady beat of his heart under your touch. He inhaled sharply, his hand tightening around yours as he pulled back slightly, his gaze intense as he searched your face.
“Dean…”, you murmured, your voice a quiet plea, filled with all the longing you’d been holding back.
He closed his eyes for a moment, his jaw tightening as if he were wrestling with himself, with the weight of everything he’d never dared to hope for. When he opened his eyes, they were dark, filled with a raw, unguarded need that made your breath catch.
“I…”, he started, his voice rough, barely more than a whisper. “I don’t want to mess this up”. He brushed his thumb over your cheek, his touch gentle but trembling, as if he were holding back a flood.
As Dean hovered over you, his hand still warm against your cheek, he remembered a conversation from just a few nights ago. You’d confessed quietly, almost shyly, that he’d been your first kiss. He’d teased you gently, surprised but flattered, but it had also made him realize something deeper—that you were trusting him with parts of yourself you’d never given to anyone else. And he’d quickly pieced it together, understood that, beyond that first kiss, you were letting him in on something new, something vulnerable.
Dean had his fair share of experiences with other girls, each encounter fading into the next, but this—this was different. This was you. And with you, every touch, every look, every whispered word felt like it held weight, like he was being trusted with something precious, something fragile. The last thing he wanted to do was rush or risk hurting you, especially with this kind of intimacy hanging unspoken between you.
He ran a hand gently down your arm, his fingers brushing over your skin with a reverence he hadn’t felt before. “I want this to be… right”, he murmured, his voice filled with quiet sincerity. He looked into your eyes, his gaze softened, that familiar cocky confidence replaced with something raw and open.
You met his gaze, your heart pounding but steady, feeling the depth of what he was offering you. “It is right, Dean”, you whispered, reaching up to trace the line of his jaw, grounding him as much as yourself. “I’ve never wanted anything more… Unless.. you don’t want it".
Dean’s eyes softened even more, and he let out a low, almost breathless chuckle as he shook his head. “Oh, sweetheart, trust me”, he murmured, his voice rough but filled with warmth, “I’ve wanted this… wanted you… since the first moment I laid eyes on you”. He brushed a thumb tenderly over your cheek, a quiet smile playing at his lips. “I just… I want it to be right. For you”.
You felt a rush of warmth spread through you, his words wrapping around your heart, settling any remaining nerves you had. The way he looked at you, with that unguarded, honest gaze, made you feel like you were the only person in the world, like there was nothing he wanted more than this moment with you.
“Then it is right”, you whispered, a smile tugging at the corner of your lips as you let your hand slip from his jaw to rest on his chest, feeling the steady, reassuring beat of his heart beneath your fingertips.
He held your gaze for a moment, as if searching for any last trace of doubt, and when he found none, he leaned down, capturing your lips in a kiss that was soft yet filled with an intensity that left you breathless. His hand moved down, sliding along your side with a gentleness that seemed almost reverent, like he was taking his time, savoring every moment, every touch, as if this was all he’d ever wanted.
Slowly, he deepened the kiss, his hand moving to your waist, pulling you closer, as his lips moved against yours with a tenderness that made your heart ache in the best way.
As the kiss deepened, Dean’s lips moved slowly, tenderly, against yours, his hands resting on your waist with a gentle but steady pressure, anchoring you both in the moment. You could feel the warmth radiating from him, the quiet intensity of his touch, his heartbeat echoing in the space between you.
He broke the kiss just barely, his lips hovering over yours as he murmured, his breath warm against your skin, “Tell me if you need me to stop… if it’s too much”. His voice was soft, roughened by the depth of his emotions, and you could hear the restraint, the care, woven into each word.
You shook your head slightly, meeting his gaze with a reassuring smile, your hands slipping up to rest on his shoulders, grounding you in his presence. “Dean… I trust you”, you whispered, letting him see the quiet certainty in your eyes, the way you felt fully, deeply safe in his arms.
His gaze softened even more, and he leaned down, pressing another gentle kiss to your lips, his touch filled with a reverence that made your heart ache.
Dean’s hand slipped down to the hem of your sleep shirt, his fingers grazing the bare skin beneath with a gentleness that sent a shiver up your spine. His touch was slow, almost reverent, as he traced small circles along your hip, his gaze never leaving yours, searching your face for any sign of hesitation. When he saw none, only the soft trust in your eyes, he let out a breath, as if he, too, had been holding onto nerves he hadn’t let you see.
When his fingers brushed along your sides, gently lifting the fabric, you lifted your arms, helping him ease it up and over your head. You bit your lip, feeling warmth flood your cheeks as you realized you were bare before him, nothing but the soft glow of the moonlight casting gentle shadows over your skin.
Dean’s gaze lingered on your exposed chest. He took a deep breath, as if trying to steady himself, overwhelmed by the sight and the trust you placed in him. The moonlight highlighted the gentle curves of your body, casting shadows that made the moment feel even more intimate and sacred.
“You’re so beautiful”, he whispered, his voice thick with awe and a touch of vulnerability. He leaned in slowly, his lips brushing gently against your skin, starting from your collarbone and making a delicate trail downward, reverent and slow. Each kiss was like a word in a silent vow, honoring the trust and affection you shared.
His hands, always so sure and strong, now trembled slightly as they traced the lines of your body, exploring the softness with a curious and gentle touch. He seemed to memorize every detail, every response his touch elicited from you.
As Dean’s lips brushed gently over your nipple, your breath hitched, a rush of warmth flooding through you. He paused, his eyes lifting to meet yours, seeking reassurance and permission to continue. The concern and care in his gaze were evident, reflecting the depth of his feelings and his desire to ensure that every moment felt right for you.
Seeing the questioning look in his eyes, you gave a small, encouraging nod, your own hands gently caressing the back of his head, guiding him back with a soft assurance.
Dean continued, his touch becoming more assured but no less gentle. He kissed you again, more deliberately this time, his lips enveloping your nipple with a tender warmth that sent a shiver of pleasure through your body. His tongue traced a slow, teasing path, exploring with a patience that had you arching slightly towards him, seeking more of his touch.
Dean’s hand slid to the small of your back, drawing you closer to him, his other hand tracing upwards along your ribcage to cradle the side of your breast, his thumb gently sweeping over your skin. The combination of his lips and the gentle caress of his hand was intoxicating.
The room was filled with the soft, intimate noises of Dean’s careful, exploring mouth and your responsive breaths, which grew sharper with each caress. The faint sounds of your whimpers mingled with the quiet atmosphere, each one sending a thrill through Dean, urging him deeper into the moment. These sounds, these quiet declarations of your pleasure, seemed to fuel him, intensifying the already palpable desire that hung heavy between you both.
Dean’s movements became gradually more purposeful, driven by the reactions he elicited from you. His kisses wandered with a deliberate slowness, tracing fiery paths down your body, pausing at your belly before venturing lower, his breath hot against your skin. Each touch was calculated to draw out the fullest depth of your pleasure, his ears attuned to every shift in your breathing, every quiet sigh and moan that escaped your lips.
As Dean’s hands moved to the waistband of your pajama pants and panties, his touch remained gentle, his eyes never leaving yours. He watched you intently for any sign of hesitation, his movements slow, giving you time to adjust or stop him.
With a careful touch, he began to pull the fabric down, his fingers grazing your skin lightly, tracing the lines of your hips as he went. The soft material slid over your legs, leaving you exposed under his attentive gaze, the air cool against your heated skin. His eyes, usually so full of confidence and playfulness, now carried a weight of reverence and awe, seeing you so open, so vulnerable before him.
You lifted slightly, aiding him as he carefully removed your pajama pants and panties, setting them aside. Once you were bare, Dean paused, his eyes sweeping over you, taking in every detail. His breath hitched slightly, a testament to the depth of his desire.
As Dean noticed your blush deepen, and your thighs instinctively press together in a mixture of nervousness and modesty, his gaze softened. The intensity of his desire was tempered by his respect for your comfort, and he sat back, giving you a little space to adjust.
Recognizing your heightened vulnerability, Dean decided to lessen the disparity between you. He reached down to unbutton his flannel, sliding it off his shoulders with deliberate, slow movements that held your gaze. He then pulled his shirt over his head, revealing his own body to you. His chest was bathed in the same silver moonlight that illuminated you, casting shadows across the muscles and scars that marked his skin—a map of his own vulnerabilities and past.
The sight of him, so open and unguarded, seemed to bridge the gap of vulnerability between you. His willingness to share in the exposure helped ease the tension in your body, seeing him as not just a partner in this moment but also as someone equally open and at risk.
He leaned in again, this time slower, his movements mirroring the care he’d shown all night. His hand reached for yours, fingers intertwining as he gently squeezed.
His chest now nearly touching yours, Dean kept his gaze locked with yours, ensuring you were comfortable as he moved closer. “Only go as far as you want”, he whispered, his breath mingling with yours, each word laced with affection and an earnest desire to keep you at ease.
You felt a wave of affection and trust surge through you at his reassurance, your earlier apprehension melting away under his understanding gaze. With a small nod, you squeezed his hand back, signaling him to continue.
Dean leaned in to kiss you again, his lips meeting yours in a gentle, loving kiss.
When Dean paused, his lips just a breath away from yours, his hand lingering at his belt as he looked at you with a mix of desire and concern. He was already achingly hard, his body more than ready, but his mind was clearly racing, considering everything and wanting to be sure.
As Dean looked around the room, his zipper already open, a flash of concern crossed his features. He was lost in thought for a moment, weighing the importance of protection against the growing heat of desire surging between you.
Sensing his hesitation, you took a deep breath, your voice steady despite the rapid beating of your heart. “Dean”, you murmured softly, catching his attention. “I’m on birth control, and… well, since I’m a… well, I’m pretty sure I’m not carrying anything”. You offered a reassuring smile, hoping to alleviate any lingering worries he had.
His eyes locked onto yours, and the concern in his gaze shifted to relief. “You’re sure?”, he asked, his voice low and earnest, searching for any trace of doubt.
“Yes, I’m sure”.
Dean, reassured by your conviction, proceeded to shed the last of his inhibitions along with his jeans and boxers. As he sat before you on his knees, fully exposed, the sight of his erection made your breath catch in your throat. The reality of the moment, the intimacy of what was about to transpire, hit you deeply. You had never seen him—or anyone—in this state, and the intensity of his vulnerability mixed with his obvious desire sent a thrill of anticipation through you.
As you bit your lip, watching him, Dean’s eyes followed your gaze, landing on his own body before returning to meet yours. He looked at you questioningly for a moment, a hint of vulnerability flickering across his face as he gauged your reaction. But then, seeing you so affected, yet composed, seemed to bolster his confidence.
Slowly, he reached out, his fingers intertwining with yours, offering you a steadying anchor as you both leaned into the deep trust you shared.
He brought your hand to his lips, pressing a gentle kiss against your knuckles before leaning in, his lips capturing yours in a kiss that was tender and deliberate. His hands moved to trace the contours of your body with a lightness that spoke of reverence, each touch careful and unhurried.
As he sat back again, his eyes never left yours. He gently placed his hands on your knees, his touch light but clear in its guidance. With a soft, encouraging nod, he coaxed you to open your legs, making room for him to come closer.
Dean moved between your legs, positioning himself with a tenderness that only deepened the trust you felt in this moment. His eyes held yours steadily, conveying both warmth and reassurance as he took in the quiet anticipation on your face. The flutter of nerves mixed with excitement quickened your heartbeat, each pulse a reminder of the profound intimacy that was unfolding between you.
Gently, Dean leaned down, pressing a soft kiss to your lips, grounding you in his presence. His hands, warm and steady, traced along your sides, sending a trail of goosebumps across your skin as he familiarized himself with each curve and contour.
As he drew closer, he paused again, his gaze searching your face for any sign of hesitation.
“If at any point you need to stop, just tell me”, he murmured, his words full of care.
You just nodded.
Dean gently grasped the base of his erection, his touch both tentative and assured as he aligned himself between your legs. As he looked back at you, his voice was soft, tinged with a hint of concern. “This might hurt a little. Hold onto me”, he mumbled, his breath warm against your skin.
You felt a mixture of nervousness and excitement ripple through you, your hands instinctively finding their way to his shoulders. Biting your lip, you offered him a reassuring smile, your fingers gently squeezing his arms in response. “I’m okay, Dean”, you whispered, your voice steady despite the racing of your heart. “Just take it slow”.
Dean nodded, his movements deliberate as he began to ease himself in.
Dean’s movements were slow and considerate as he gently pushed forward, his gaze initially fixed on the union of your bodies to ensure everything was right. Sensing your intake of breath and the soft whimper that escaped your lips, his eyes immediately lifted to meet yours, full of concern and empathy.
Your reaction, the slight tightening of your fingers on his shoulders, your nails pressing into his skin, didn’t go unnoticed. It was a silent communication of the mix of pain and the overwhelming rush of new sensations you were experiencing. Dean paused, holding still, allowing you time to adjust to him. His voice was soft, soothing. “Hey, look at me”, he murmured, encouraging you to focus on his eyes, seeking to provide a distraction and a point of comfort.
“I’m right here with you”, Dean continued, his tone tender. “Tell me if you want me to stop, okay?”. His hands moved from your hips to gently cradle your face, thumb softly stroking your cheek, a gesture meant to reassure and calm you.
You nodded, your breaths coming in heavy bursts as you adjusted to the sensation. The discomfort was sharp but fleeting, and you found your voice, albeit shaky, whispering against his ear, “Just keep going”. You wanted to move past the initial pain, to find the connection that awaited beyond this threshold.
Dean responded with a gentle nod, his expression mingling concern with deep care. He kissed your forehead softly and with a slow, steady breath, he eased forward further, his voice a low murmur near your ear. “There we go”, he said soothingly, exactly as he felt the resistance give way, the moment marking your transition fully into this new intimacy.
The sensation was intense, and you couldn’t help but cling to him, your arms wrapping tightly around his neck as a quiet cry escaped you, muffled against his skin. Dean held you close, pausing again to give you a moment, his body a steady presence against the wave of emotions and physical sensations flooding through you.
As you both held this deeply intimate pause, Dean’s steady breaths against your ear helped to ground you, his presence a reassuring comfort. “You’re doing great”, he reassured, his lips brushing against your temple as he spoke.
“Ready to keep going?”, he whispered softly, noticing the subtle affirmations in your body language that you were adjusting, becoming more comfortable with the new intimacy. He held you close, your body slightly elevated from the mattress in his arms, creating a space that felt both protective and intensely personal.
His control was palpable, every muscle tensed to maintain the slow, careful pace that he knew was necessary. He could feel the overwhelming sensation caused by your tightness around him, and it took every ounce of his focus to hold back, to move at a pace that ensured your comfort over his own rapidly building need.
You nodded in response to his question, the warmth of your breath tickling his neck. “Yes, keep going”, you murmured back, your voice a mix of nervous excitement and growing trust. Your hands moved to his shoulders, gripping him slightly as a signal of your readiness to continue.
Dean carefully eased you back down onto the mattress. As he laid you down, his lips found yours in a tender, deep kiss, an unspoken acknowledgment of the intensity of the moment. The kiss served not only as a connection but also as a gentle silencer, intuitively understanding that your reactions might grow louder with the increasing depth of sensation.
As his lips pressed firmly against yours, he began to slowly pull back, withdrawing just a few inches, the movement smooth to keep the experience as gentle as possible. The mix of his slight withdrawal and immediate return drew a muffled sound from you against his lips, a sound that was part pleasure, part overwhelmed response to the new depths of intimacy you were exploring together.
You kept your hands on his biceps, feeling the muscles flex beneath your fingertips as he moved against you, each gentle thrust creating a rhythm that resonated deep within. His hips met yours with a soft pressure, the connection eliciting a wave of warmth and pleasure that coursed through your body. The room filled with soft, wet noises—Dean’s quiet grunts of effort mixed with your little whimpers of pleasure, a symphony of intimacy that deepened the moment.
As Dean continued, his breathing grew heavier, a testament to the depth of his effort and arousal. After several more gentle thrusts, his head dropped to rest against your collarbone, his breaths hot and quick against your skin. The physical intensity of the moment was mirrored in the emotional connection that pulsed between you, binding you closer with each shared breath.
Beneath him, you still felt a tension within your body, a mix of nervous excitement and the lingering edges of discomfort as you adjusted to the new sensations. Despite the intimacy and your trust in Dean, your body’s response was still cautious, a natural reaction to your first experience.
Sensing your tension, Dean’s voice came softly, his lips moving against your skin as he spoke, “Tell me how it feels".
"It’s… intense", you breathed out, your voice barely more than a whisper, yet carrying the weight of the new sensations and emotions coursing through you. Your fingers instinctively tightened around his neck, nails grazing his skin as if grounding yourself in the moment. Dean felt the press of your touch, his body responding with a shiver that mirrored his own restraint, his focus still unwaveringly on you.
Hearing your response, Dean lifted his head slightly, brushing his lips softly along your neck, each kiss deliberate, gentle. “You’re doing so good”, he murmured against your skin, his voice a blend of pride and tenderness. His hands moved along your sides, his touch soothing and reverent, as if each motion was meant to calm and encourage you.
Your heart pounded with every word, every gentle caress of his lips against your neck. The initial tension in your body began to dissolve, bit by bit, replaced by a warmth that radiated outward, filling the space between you.
With a renewed sense of calm, you found yourself moving with him, adjusting to his rhythm, feeling the discomfort gradually fade and transform. The pleasure, at first subtle, grew slowly, each gentle thrust amplifying the connection that was building between you both.
“Just like that”, he murmured against your ear, his voice thick with both arousal and affection. “We’ll go as slow as you need”.
As Dean sensed your growing comfort and readiness, he carefully adjusted his position, his movements both mindful and precise. He shifted slightly, changing the angle of his thrusts in a way that deepened the connection. His gaze remained locked with yours, watching for any reaction, any sign to guide him.
Then, with a gentle but firm movement, he found a new angle that touched you in a way that sent a sharp, intense wave of pleasure coursing through you. As he hit your G-spot, the sensation was overwhelming, like nothing you had ever felt before. It was a revelation, a rush of intense pleasure that took your breath away.
Instinctively, you pressed your mouth against his shoulder, your lips pressing tight to muffle the loud moans that erupted from you. Your body responded with an involuntary shudder, a climax that rolled over you unexpectedly from just that single, perfectly-angled thrust. Your fingers dug into his shoulder, gripping him tightly as waves of pleasure washed over you, leaving you breathless and momentarily overwhelmed.
Dean held you close, his arms wrapping around you as he felt the tension surge through your body. He stilled his movements, allowing you to ride out the waves of your climax, his lips pressing tender kisses onto your hair. “That’s it, just let go”, he murmured, his voice a soothing balm as he supported you through the intensity of your reaction.
Dean held you tightly, feeling your body shivering beneath him as you clung to him in the aftermath of your climax. The intensity of your response left him equally overwhelmed, his body instinctively reacting to every subtle movement of yours. He tried to remain still, to give you a moment to recover, but the rhythmic clenching around him made it increasingly difficult to maintain control.
Feeling you continue to tighten around him, Dean’s resolve wavered. With a deep, ragged breath, he allowed himself to move once more, his hips pushing gently but firmly deeper into you.
As he moved, his face buried in the crook of your neck, where your pulse beat wildly against his lips. His body tensed in anticipation.
Then, with a deep groan that vibrated against your skin, Dean surrendered to the overwhelming sensation. He spilled into you, hot and warm, his climax washing over him in powerful waves that mirrored your own intensity. As he released, his body shuddered, his grip on you tightening.
After a few long moments, as the waves of his climax ebbed, Dean’s movements slowed, finally coming to a stop. He remained inside you, his body heavy with exhaustion but gentle in its weight. His breathing slowed, and he lifted his head to meet your gaze, his eyes soft and filled with a mix of wonder and deep affection.
Dean kissed you tenderly, a kiss that spoke of gratitude and deep connection. “Are you okay?”, he whispered, his voice thick with emotion. His concern was evident, always attentive to your well-being, ensuring that the experience had been as profound for you as it had been for him.
You nodded, still catching your breath, a smile spreading across your face as you wrapped your arms around him. “I’m more than okay”, you assured him, your voice soft and filled with a warmth that echoed the deep bond you both had just deepened.
Dean’s cheeks colored with a faint blush as he realized the practicalities of your intimacy. “Do you have a towel or something?”, he asked, slightly awkward as he sat back, his movements gentle to maintain the intimacy and care of the moment.
You bit your lip, a little flustered, and reached blindly for the towel you had used earlier to dry your hair, which was now beside your bed. Handing it to him, you were still catching your breath, not entirely sure of his intentions but trusting him to handle the situation with the same care he had shown throughout your time together.
As Dean took the towel from you, he carefully began to withdraw, his movements slow and considerate. The moment he pulled away, you felt a warm spill between your thighs. “Oh gosh, I’m so sorry”, you breathed out, a rush of embarrassment flooding you as you instinctively hid your face under your arm.
Dean immediately softened, his own embarrassment mingling with a gentle understanding. He leaned over, his hand lifting your arm away from your face. “Hey, no, don’t be sorry”, he reassured you softly, his voice tender. “It’s okay, it’s all part of it”. His smile was kind, meant to ease your discomfort as he gently wiped the towel across both of you, careful not to make the situation feel any more awkward.
“This is normal, okay?”. Dean continued, his tone soothing as he made sure to clean up carefully. “Nothing to be embarrassed about”.
Dean chuckled softly, the sound light and warm. “You just might want to change your sheets tomorrow”, he teased, giving you a playful grin. You felt a mix of curiosity and bashfulness, biting your lip as you sat up slightly, trying to see what he was talking about. But before you could fully assess the situation, Dean tugged you back down beside him, flopping onto the bed and pulling you right along with him.
He wrapped his arm around you, anchoring you close, his fingers tracing gentle patterns along your shoulder as he settled beside you. It was a distraction in the best way, grounding you in the warmth of his presence rather than the small embarrassments of the moment. His hand found yours, fingers interlacing as he brought your hand up to his lips, pressing a soft kiss to your knuckles.
“There”, he murmured with a contented sigh, as if he’d achieved some small victory by pulling you back into his embrace. “Nothing else matters right now. Just you, me, and a very good night’s sleep”.
Your cheeks burned with a blush that didn’t seem to fade, the warmth of your face pressed against Dean’s bare chest as you tried to hide your flustered state. The feel of your breath, warm and quick against his skin, brought a smile to Dean’s lips, his heart swelling with affection for the endearing vulnerability you displayed.
He wrapped his other arm around you, pulling you even closer, if that were possible. The gesture was protective, affectionate, and filled with the silent promise of his care. “You don’t have to hide”, he whispered, his voice low and soothing. “I love seeing you like this—just being real and you”.
Dean’s fingers gently tilted your chin, encouraging you to look up at him. As your eyes met his, there was an undeniable tenderness in his gaze, a depth of feeling that seemed to pull you even deeper into his orbit. He adored these moments with you, the quiet intimacy that spoke louder than any grand gesture. The simplicity of the moment—the softness of your expression, the sincerity in your eyes—made him fall for you even more.
“You know”, he continued, his thumb brushing lightly across your cheek, “every time you blush like that, I fall a little harder”. His tone was teasing, but the emotion behind it was earnest, filled with the kind of affection that could only grow from truly knowing and cherishing someone.
Your breath hitched at his words, heart racing as the weight of his affection settled over you. Before you could respond, Dean leaned in, his lips capturing yours in a gentle, lingering kiss. The touch was soft, unhurried, filled with a tenderness that said everything he hadn't put into words. His hand cradled your cheek, his thumb brushing lightly against your skin as he poured his feelings into the kiss—gentle, reverent, and filled with a depth of emotion that made you feel cherished beyond measure.
The kiss deepened slightly, a quiet urgency within the soft, slow rhythm of his lips against yours. It wasn’t about passion or need, but rather a quiet, profound connection, a way to show you how much you meant to him in a language beyond words. His fingers tangled in your hair, holding you close as he pulled back just a fraction, his forehead resting against yours, his breaths warm against your face.
When he finally drew back, his eyes met yours, a soft smile tugging at the corners of his lips. “I think I’m in trouble with you”, he murmured, his voice low and teasing, but his gaze held that same, unwavering sincerity.
End of the Flashback
Dean straightened slightly, clearing his throat as he took in a deep breath, trying to steady himself as the memory washed over him. The intensity of the recollection left him feeling vulnerable, a warmth spreading through him that he hadn’t anticipated. He could feel his body’s response, a testament to the lingering effect you had on him, even after all these years. Across the room, he caught sight of you, your face rare and completely flushed, eyes momentarily distant, lost in the same memory.
When your gazes met, it was as if time rewound, pulling both of you back to that quiet night filled with whispered promises and shared vulnerability.
Dean gave you a small, tentative smile, his usual bravado softened, replaced by something quieter, more real. The air between you was charged, almost as if the memory itself had bridged the gap of time. It was more than just nostalgia; it was a reminder of the connection you shared, one that neither of you had ever truly let go.
You cleared your throat, hoping to steady yourself as you handed Sam another book, though your mind was still caught in the haze of that shared memory. As you turned, you suddenly felt Dean’s presence closer than before, his frame leaning over you, his arm brushing lightly against yours. The scent of his familiar cologne filled the air, mixing with the worn leather and faint vanilla notes you’d always associated with him. The proximity, the warmth radiating from him, sent a shiver down your spine, your pulse quickening despite your best efforts to keep calm.
“Guess some memories don’t fade, huh?”, he murmured, his voice low, just for you, the words carrying a weight that made your breath hitch. The intimacy of his tone, paired with the way he looked at you, his gaze both questioning and intense, made it clear he felt it too—the pull, the lingering spark that neither time nor distance had managed to extinguish.
You managed a soft smile, feeling your cheeks flush even more under his gaze. “Seems like they have a way of sticking around”, you replied, your voice barely a whisper, but the words held an edge of truth that you both understood.
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A/N: Please let me know what you think.🥰 
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Taglist: @blackcherrywhiskey @baby19sthings @suckitands33 @spnfamily-j2 @lyarr24 @deans-baby-momma @reignsboy19 @kawaii-arfid-memes @mekkencspony @lovziy @artemys-ackles @fitxgrld @libby99hb @lovelyvirtualperson @a-lil-pr1ncess @nancymcl @the-last-ry @spndeanwinchesterlvr @hobby27 @themarebarroww @kr804573 @impala67rollingthroughtown @deans-queen @deadlymistletoe @selfdestructionandrhum @utyblyn @winchesterwild78 @jackles010378 @chirazsstuff @foxyjwls007 @smoothdogsgirl @woooonau @whimsyfinny @freyabear @laaadygisbooornex3 @quietgirll75 @perpetualabsurdity @pughsexual @berryblues46 @deanwinchestersgirl8734 @kr804573 @iloveeveryoneyoureamazing @globetrotter28
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fun-kyto-wn · 8 months ago
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this shot is quite literally insane dude I could write a whole essay about it. The director was like “Oh hey guys let’s do a close up on their hands to emphasize the importance of this gesture (as if making someone a mixtape isn’t already romantic enough), their fingers just inches apart to show have close but yet far away they are, that they share these little moments of intimacy but the weight of the unspoken feelings lingers heavy in the air oh and yeah let’s also make it look like the god damn fucking Michelangelo painting.. but nothing to see here.”
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lamiasage · 9 months ago
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A little Dean doodle | ref
[More art, wips, and sketches on my Patreon 💖]
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dreampencil · 2 months ago
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Waiting for paint to dry...so here is Dean silenced by the Empty. Mars lumograph black + watercolour. To be added or removed from tag list, please let me know :)
@naughtystiel
@malicmalic
@fivefeetfangirl
@letmeblued
@castielsprostate
@dean-you-assbutt-cas-loves-you
@casdeans-pie
@pattywinchester
@bogwitchatrois
@bloodydeanwinchester
@beregond35
@horrorcas
@charlottemanchmal
@strawlessandbraless
@blue-eyed-cutiepatootie
@thefailcollection
@disabled-dean
@squirrelsarecool
@hauntedpearl
@markofcastiel
@butch--dean 
@rennerator
@sailorsally
@xofemeraldstars
@forkinthegarbagedisposal
@happilyfeatherafter
@universalcas
@riverwithoutbanks-art
@shutupjaff
@magnificent-winged-beast
@sanndh
@mrs-padalecki2341
@archervale
@idontexistbutwhodoes
@eeveestoneson
@reader-meg
@integer-0verflow
@missingmoonflowers
@seeingthestarsmakesmedream
@sini5terxwalru5
@shipsawayandusuallygay
@famouskidangel
@justjayisfine0
@examishbookwyrm
@ididit-allofit-foryou
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destielprophet · 4 months ago
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this parallel is truly insane.
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thirdsaltyhunter · 20 days ago
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If I Catch You
Summary: Dean chasing you through the halls of the bunker in a ghostface mask, what more do you need
Warning: SMUT, if I catch you I f*ck you trope, mask k*nk, choking, praise, edging, manhandling
A/N: did I forget to post this yesterday cause I was to busy partying... yes but hopefully you'll enjoy this enough to forgive me
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You had always loved Halloween even despite being a hunter. It brought back the happy memories from your childhood, when there were no worries, the monsters were only people in masks and the good guys always won at the end of every scary movie. Dean shared your appreciation for the holiday. Even before you and him started dating, you would often spend Halloween nights curled up on motel beds, watching horror marathons with all the snacks and sugar you could handle. Sam on the other hand didn't see the appeal. Sometimes he would join you in your movie watching, but it was mostly to appease you and avoid ridicule from Dean.
This year you and your boyfriend had the bunker all to yourself. Sam had chosen to spend the night with Eileen and leave the two of you to your festivities.
The empty bunker allowed the perfect opportunity for you and Dean to play out a fantasy that you had talked about a few nights before, when you were cuddled up bingeing the Scream franchise.
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"Ghostface is hot," you blurted randomly in the middle of the movie. You mostly said this to see his reaction, but there was a hint of truth to your statement.
"Why?" he said in utter confusion. He paused the movie and looked down at you in his arms.
You shrugged. "I don't know masked men are just hot."
"Masked men?" he tried to hide the hint of amusement.
"Oh yeah, it's a real popular thing now. I can show you all the thirst trap videos."
"Yeah I don't need to see that."
You laughed at his look of disgust before he continued.
"So what your saying is that I need to get a Ghostface mask, hm?" he said with a smirk.
"I mean I wouldn't mind, have you chase me through the halls in it." You tilted your head back to face him, your lips almost touching.
"What happens when I catch you?", he asked with a devious smile, his hold on you tightening slightly.
"You'll have to find out," you responded, your voice sultry and teasing.
"I think that can be arranged."
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One costume store purchase later and you found yourself in only a set of sexy underwear, standing in the empty hallway. The concrete floor was cool under your bare feet, but your racing pulse kept you from being cold.
Dean had given you a head start before he would try to come and find you. Your excitement was growing. He wasn't going to chase you, if it came down to a sprint race, Dean would win every time. No, he was going to hunt you. You knew this made the game more even, but you also knew that he was crafty and smart. Though in all honesty you wanted to be caught, you were just going to be a little tease before you let him find you.
You had just rounded the corner by the kitchen, when the power went out, causing the bunker's red emergency lights to come on.
Nice touch, you thought.
You heard his voice echo through the hall, signaling that he was coming to find you. Your adrenaline was pumping. Not out of fear, you knew Dean would never hurt you, but out of anticipation for what would happen when he found you.
You slipped into kitchen looking for a spot to hide. Unsatisfied with the spots, you head to the library. You hid in the far corner behind one of the shelves and waited. You listened for his footsteps but heard nothing, years of hunting had trained him to be light on his feet. When you finally heard his voice call your name he was much closer than you expected. He purposefully stepped heavy coming up the stairs from the War Room, his boots thudding against the stone.
You took the opportunity to dart out the door in the back of the library. The bookcase blocked you from his view, but he definitely heard the door shut. You bolted down the back hall, heart pounding as you rounded the corner just as the door opened behind you.
Quietly you slipped into one of the bedrooms and hid under the bed. You listened until his footsteps passed the door and went down the hall. Crawling out from your hiding spot, you checked to make sure the hall was empty before sprinting the opposite direction.
As you ran past the next hall you saw him rounding the other end. You picked up the pace, knowing he had seen you. You turned the next corner and stopped, pressing your back against the cool tile wall to catch your breath. When you decided the coast was clear you went to move to the next hall, when an arm wrapped around your middle, you back pinned to his chest.
You tried to wriggle from his grasp just making it free when you stumbled. You caught yourself, but his hand caught your ankle dragging you across the polished concrete floor and pulling you under him.
He rolled you over and you came face to face with the black eyes and long mouth of the mask, illuminated by the red glow of the lights. This was the first time you had actually seen him in the mask and it was even hotter than you imagined. When he pinned your hands above your head you knew you weren't getting away.
"Gotcha," he growled.
"What are you going to do with me now?" you said through panting breaths, partially from running, partially from how incredibly turned on you were right now.
"You'll have to find out," he responded before using one hand to pull his belt from his jean and loop it around your wrists.
Ok that was hot.
When your hands were secured, he stood up scooping you up off the floor and tossing you over his shoulder, delivering a quick smack to your ass before walking toward your shared bedroom. It wasn't often that he manhandled you like this and you were loving every second of it.
When you got to the bedroom, he tossed you onto the bed and straddled your legs. He hooked two fingers into the belt around your wrists.
"You want this to stay on?" he asked.
You nodded eagerly. Even being dominant and aggressive, he never wanted to push you limits, solely focused on giving you what you wanted.
"Stay," he ordered, getting up from the bed to strip down to his boxers, leaving the mask in place.
You watched him with lust blown eyes, your chest still rising and falling rapidly as you admired his body. He moved to the end of the bed, grabbing your ankle and pulling you to the end. Your underwear was pulled down your legs and tossed over his shoulder. He wrapped you legs around his hips and you could feel his clothed erection. You moaned grinding down on him until his arm crossed you hips, holding you still.
He ran two finger through your slick. '"So wet for me. Is this just from me chasing you?"
You nodded again.
He lowered to his knee, his masked face coming level with your dripping cunt. Two of his fingers dipped into you, immediately curling into the spot that made your back arch and your knees weak. Your head fell back letting the pleasure wash over you.
From the box under the bed, he pulled out your vibrator. He planned to torture you tonight.
"Don't cum until I'm inside you. Do you understand me?" he said turning the toy to the lowest setting and pressing it to your clit.
"Yes," you moaned, hands gripping the sheet above your head. You didn't know how long you were going to last. You were already on the edge of release and he had hardly touched you yet.
As you got close he removed the vibrator, running his hand up your thighs and squeezing your hips to sooth you. You whined and looked at him between you legs. You tried to give him your best puppy eyes, but you couldn't see his expression. You only were met with the blank stare of the mask and the vibrations returning to your sensitive cunt.
He continued teasing you, edging you another four or five times. You hated it and loved it at the same time. It amazed you how he knew exactly where to keep you on edge, or at least it would amaze you, if there was a single part of your brain that could think straight.
"Dean," you whined again, desperate for release.
"Beg for it," he responded sternly, fingers dipping inside you again.
"Please, fuck me." You squirmed, you didn't know if you wanted to get away from he sensation or fuck yourself on his fingers.
He sped up his motions and leaned over you body until he was face to face with you. You could just barely see his eyes, but you knew he was watching you fall into ecstasy.
"Please," you begged.
He removed his fingers and dropped his boxers. His cock was thick and dripping precum, edging you had teased him almost equally as much. He pulled your hips even closer to the edge of the bed and hooked your shaking legs over his shoulders. His hands gripped your hips firmly as he slid into you, filling you completely.
He watched your face as your head fell back in pleasure, a loud moan escaping your lips.
"That's my girl," he praised, running his hands up and down your sides, desperately trying to keep himself together.
He started thrusting into you, slow, but so deep you could hardly take it.
"Look at me," he said, his hand came up to circle around your throat to put your attention back on him.
Your eyes opened to watch as he fucked you. You could see a blush of exertion creeping down his neck from under the mask. He gently added pressure to the sides of your throat as the speed of his hips increased.
Your hands reached for him as you got closer to falling apart. Noticing how close you were, he started to circle your clit with his thumb. You came with cry of his name, your hand gripping his forearm, his hand loosening from your throat, causing you to feel almost high.
He planted his hand beside your head as his hips stuttered and he came with a deep moan. You both stilled for a few minutes, panting and trying to regain your bearings.
After a moment, he gently pulled out to go get a towel to clean up your combined mess. You squirmed from the sensitivity as he wiped you down. He whispered an apology before tossing the rag and undoing the belt from your wrists.
Finally removing the mask, he ran a hand down his face and smiled down at you. It was funny to see him have that boyish grin after playing the sexy, dangerous slasher for the past hour. He lifted you up to place you at the top of the bed against the pillows.
"That was awesome," he said, laying down beside you and wrapping you in his arms.
"Yeah it was, I fucking love you." You laughed and buried your head in his neck.
"I love you too sweetheart, and I love that I can do things like this with you."
You nodded in agreement before you started to feel how worn out you were.
Both of you were exhausted from your activities and quickly fell asleep, deciding to take a nap before settling down for a night of Halloween movies and junk food.
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reallyunluckyrunaway · 4 months ago
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❤️❤️ THIS ❤️❤️😤🙏
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letsdropdeaduniverse · 2 months ago
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cheynovak · 2 months ago
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Sleeping beauty
Characters: Dean Winchester x Y/N Female character     
Summary: REQUEST: Dean sees Y/N sleeping, in his bed, in his shirt and it drives him insane. The heat he feels rushing through his veins. And it's all because she looks so good while sleeping. He just can't keep his hands to himself.
Warnings: 18+ Explicit, Somno, mastrubating, unprotected P in V, slight dominance, ...
English is not my first language 
*This story is my own original story, please do not copy my work, reblog/comments/likes are appreciated* 
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Dean pushed open the heavy metal door of the bunker with a quiet grunt, his entire body aching from the hunt. The long drive back had done nothing to ease the tension in his muscles, and the only thing on his mind was crashing in his bed.
Dean pushed open the heavy metal door of the bunker with a quiet grunt, his entire body aching from the hunt. The long drive back had done nothing to ease the tension in his muscles, and the only thing on his mind was crashing in his bed.
It was late—really late. The dim lights of the bunker cast a soft, familiar glow over the stone walls, offering a kind of comfort he rarely admitted to feeling.
The hunt had been brutal, but it was over. For now, at least. He ran a hand through his tousled hair, feeling the grit of the day clinging to him like a second skin.
All he wanted was to crawl under his sheets and sleep for as long as his mind would allow, which wasn’t ever as long as he hoped.
Kicking off his boots near the war room, planning on taking a quick shower, just to clean up before going to bed. Or that was what he thought he'd do. He padded silently down the hall toward his room.
As he got closer, a sense of something different hit him—something warm, something familiar. The door to his room was slightly open, a thin warm light spilling into the hallway from the bedside lamp.
Dean's brow furrowed in confusion, but the weariness in his body kept him from thinking too much about it.Pushing the door open, he froze in the doorway.
There, nestled in the middle of his bed, lay Y/N.
She was on her side, facing away from him, curled up in the middle of his bed like she belonged there.
The soft fabric of his worn, oversized flannel shirt draped loosely over her body, the sleeves bunched around her hands.
The sheets were tangled between her legs, one knee tucked up and the other stretched out, the thin blanket doing little to hide her body. Her hair spilled across the pillow, framing her peaceful face.
Her hip and ass showing over the sheets since she wore little to nothing except a pair of panties, Oh god... what is she doing to me!
Dean couldn’t move. Couldn’t speak. His eyes glued on her body. A part of him was surprised, but another part—one he rarely allowed to surface—felt like this was right. Like seeing her here was what he needed after a hunt like that.
After a life like this. Come home, find her naked or nearly naked in bed, fuck her till he find sleep himself.
His gaze lingered on her for a moment longer. Before he silently took his fresh shirt and boxers to go shower. While he closed the door behind him softly he kept looking not to wake her.
His mind spiralled in the shower. Why was she there? Did she miss him or maybe her own hunt was shitty and she needed him?
But all he could think of was her curves, how her ass lifted in the air, calling his name. Dean's cock was throbbing, his hand moved instinctively to it, making the release quick and hard.
But the second he turned the shower off, thanks to his own vivid imagination, he was hard again.
He walked back to his room, half expecting Y/N to be gone. But no... she was still there, in the same position.
The soft rise and fall of her breath was the only sound in the room, the quiet rhythm calming something deep inside of him. She looked peaceful, completely at ease. It was such a stark contrast to the usual chaos of their lives. And she was in his bed, wearing his shirt.
She turned a little more, showing herself a little better. Dean’s lips quirked up into the faintest hint of a smile. She is asking for it.
He stepped forward quietly, not wanting to disturb her, and sat on the edge of the bed. The mattress dipped slightly beneath his weight, but Y/N only stirred for a second before settling back into her dreams.
She looked so small wrapped in his clothes, the shirt swallowing her frame, and the sight did something to his heart (and cock) he couldn’t quite explain.
For a while, Dean just watched her sleep. His eyes traced the soft lines of her face, the way her lashes brushed her cheeks, how her lips parted slightly with each breath. Hands hovering over her curves wanting to touch her skin.
He didn’t know how long he sat there, just soaking in the moment, but for once, there was no urgency. No looming threat, no ticking clock. Just her, and the quiet sound of their breathing. Unless he counted his erection as a ticking time bomb...
They often enough had a quick fuck during or after a hunt. Just to release stress, this wasn’t different, all though he tried to ignore the sensation his cock was giving him. Just releasing stress.
He leaned back slightly, his hand coming so close to touch her. The warmth of her skin was a stark contrast to the coolness of the room, and he found himself wondering again how she’d ended up here.
Did she miss him while he was gone? Had she come looking for comfort in his absence? Or was she desperately looking for sex. That wouldn't be a first.
They shared a bed... couch... car... They settled boundaries before. And this was something he knew she'd be into.
His hand now warm on her hip made her lean closer to him, showing him a little more.
His flannel hung loosely off her shoulder, exposing the smooth skin of her collarbone, seeing how she was naked under his shirt.
Fuck! Dean had to fight the urge to reach out, to touch her, to pull her close, to knead and feel her breasts, feel how her soft nipple hardened with his touch.
Instead, he let out a soft sigh and ran a hand down her leg.
Carefully, not to wake her, Dean turned beside her on the bed, The mattress shifted slightly, and Y/N stirred again, her brow furrowing for a moment before she relaxed once more. Dean turned on his side, facing her, his head resting on the pillow just inches from hers.
But he couldn't stop himself. His hand moved slowly, his fingers brushing a strand of hair from her face, tucking it gently behind her ear. The touch was so light, so careful, as if he was afraid of shattering the calm of the moment.
His fingers moved over her collarbone to her breast softly kneading her flesh.
As if sensing his presence even in her sleep, Y/N shifted closer to him. Her body instinctively pressed into his, her ass moving against his hips.
Dean’s breath hitched at the contact, the feel of her so close sending a warmth through him. Fuck he needed her!
She mumbled something incoherent in her sleep, her fingers curling slightly into the fabric of his sheets. Dean chuckled softly under his breath, a rare sound in the stillness of the room.
“You always steal my shirts.” he whispered, even though he knew she wouldn’t hear him. His voice was rough with exhaustion and need but soft, the kind of tone he only used when it was just the two of them.
"This time you'll need to pay for it princess." He whispered while his hand dipped between her legs. Unknowingly she let him, moving her leg a little higher. "Fuck you're so wet already... did you...?" his voice broke off.
Would she? The idea of her playing with herself in his bed, in his flanel drove him insane. Her breath became deeper while his fingers played with her. Drawing slow easy circles on her clit.
He tugged her panties aside, before he freed his throbbing dick from his boxers. No longer able to wait, he rubbed himself against her wet core. The feeling almost enough to come then and there.
Seeing how her panties get wet with their movement.
A soft moan escaped her mouth, "D-Dean?" her voice sounded sleepy. Her hand moved back, trying to find him, and she did, pretty easily she found the back of his head, pulling him closer.
His other arm slid under her, pulling her just a little closer, and she instinctively settled into him, her head now resting against his chest.
"Shh..." He whispered. He turned her on to her belly, granting himself more access. Her hand kneading the pillow while he adjusted himself. Pulling her panties further down. Kneading her ass, kissing her flesh.
He guided himself inside, feeling her thighten just a little by the surprise of him. Her body reacted, a soft "Mhm." escaped her mouth, not knowing weither she was fully awake or he'd just given her a great dream.
"D-Dean?" she moaned sleepy. "What are you...Oh!" He leaned in closer, thrusting all the way in "Just enjoy baby." He said before he kissed her neck. She was clearly awake now, pushing her ass up so he could thrust deeper.
His hand fisted her hair, "Do you have any fucking idea what you’re doing to me? Sleeping in my bed, halve naked."
"Mhm..."
"What did you think of when you tickled that pretty little cunt of yours." Her head lifted. He knew... but he bit playfully in her neck. to hold her down.
"I felt it... while you where sleeping, I felt how wet you where without me even touching you." A breathy "Oh." escaped her mouth.
"You wanted me to fuck your sleeping pussy didn't you."
All she could was moan in response.
"Yes..."
--
Please like, share or comment when you liked the story. If you liked this, please check out my masterlist for other stories.
Tag list:-> If you want to be added let me know what you like to read! If anyone feels like you're tagged too much, also let me know please. :)
@deans-baby-momma @soab1967 @livingdeadblondequeen @ladysparkles78 @kr804573 @nancymcl@suckitands33 @mostlymarvelgirl @globetrotter28 @jackles010378 @hobby27 @call-me-mrs-winchester @winchesterwild78 @deans-baby-momma @soab1967 @livingdeadblondequeen @ladysparkles78
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deanway-to-heaven · 5 months ago
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Dean Winchester in every episode | S01E01 | Pilot/Woman in white
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kryp-does-random-stuff · 4 months ago
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Tried another method of rendering but i just keep losing against my brain overthinking/overdoing all that jazz.
So, I lost my patience during the rendering of the clothes especially... thus i didn't finish that.
And you didn't notice it, clear? 😉 Ref pic:
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wandering-winchesters · 3 months ago
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Unspoken Feelings
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Summary: What started as simple, comforting snuggles between friends gradually deepens into something more
It started as something simple, something innocent. Just a couple of friends seeking comfort in each other after a particularly rough hunt. You and Dean had always been close—there was an unspoken bond between you, forged through countless battles, late-night heart-to-hearts, and a mutual understanding of the life you both led.
The first time it happened, you didn’t think much of it. You were both sitting on the couch in the bunker’s library, exhausted and battered from the latest hunt. The adrenaline had worn off, leaving behind the aches and bruises, both physical and emotional. You’d been talking about nothing in particular, just letting the words fill the space, when you suddenly found yourself leaning against Dean, your head resting on his shoulder.
To your surprise, Dean didn’t pull away. Instead, he wrapped an arm around you, pulling you a little closer, his hand resting comfortably on your arm. It was a simple, platonic gesture, one that felt natural, even necessary in that moment. The comfort of his presence, the steady rhythm of his breathing, it all made you feel safe, grounded.
“Rough night,” you murmured, your voice muffled against his shoulder.
Dean chuckled softly, the sound rumbling through his chest. “You can say that again.”
You didn’t say anything else, and neither did he. The silence between you was comfortable, familiar. You stayed like that for a while, just leaning on each other, taking solace in the fact that, for the moment, you were both okay. It was just a quiet, comforting moment shared between two friends who had seen more than their fair share of darkness.
After that night, it became a sort of unspoken tradition. Whenever the world felt too heavy, whenever the hunts took too much out of you, you’d find yourself sitting next to Dean, letting your head rest on his shoulder, his arm draped casually around you. Sometimes you’d talk, sometimes you’d just sit in silence, but the snuggles became a constant—a small, quiet escape from the chaos of your lives.
Over time, those moments became more frequent. It wasn’t just after hunts anymore. Sometimes, you’d be watching a movie, and you’d find yourself leaning into him, or you’d be sitting at the kitchen table, and he’d rest his hand on your back, just a simple touch that made you feel connected, understood.
You didn’t think much of it at first. It was just Dean—Dean who always had your back, who always knew what you needed, even before you did. But as the weeks went by, you started to notice the little things. The way your heart would skip a beat when his hand brushed against yours, the way your breath would hitch when he pulled you closer during one of your late-night snuggles, the way you found yourself craving his touch more and more.
It was confusing, this shift in your feelings, but you didn’t let yourself dwell on it. After all, it was just Dean. Your friend, your hunting partner, the one person you could always count on. And yet, something had changed. The snuggles that had once been purely platonic were beginning to feel like something more, something deeper.
You started to notice that Dean was different too. He held you a little tighter, his hand lingering on your arm or your back a little longer than before. His touches were softer, more deliberate, like he was savoring the contact. There were moments when you’d catch him looking at you, his green eyes filled with something that made your heart race, but he’d always look away before you could figure out what it was.
One night, after a particularly stressful day, you found yourself in Dean’s room. You hadn’t planned on going there, but when you passed by his door and saw the light on, your feet had carried you inside before you could think twice about it.
Dean was sitting on the edge of his bed, his shoulders slumped, clearly exhausted. He looked up when you walked in, a small, tired smile tugging at the corners of his mouth. “Can’t sleep either, huh?”
You shook your head, feeling a wave of warmth and affection for him wash over you. “No. Mind won’t shut off.”
Dean patted the space beside him, and you didn’t hesitate to sit down next to him, the familiar comfort of his presence already easing some of the tension in your chest.
Without a word, he wrapped an arm around you, pulling you close, and you rested your head against his shoulder, feeling the steady rise and fall of his breathing beneath your cheek. The quiet settled over you both, and for a while, you just sat there, letting the silence do the talking.
But tonight, something felt different. The way Dean’s hand was resting on your back, the way his thumb was gently tracing patterns on your skin—it felt more intimate, more intentional than it had before. Your heart started to race, and you couldn’t help but wonder if he was feeling it too, if he’d noticed the shift between you.
“Dean,” you whispered, your voice barely audible in the stillness of the room.
“Yeah?” he replied, his voice just as soft, almost hesitant.
You hesitated, unsure of how to put what you were feeling into words. “Do you ever… do you ever think about us? About what this is?”
Dean was quiet for a moment, and you could feel his breath hitch slightly, like he was trying to figure out how to respond. Finally, he spoke, his voice low, almost vulnerable. “Yeah, I do. More than I probably should.”
You lifted your head to look at him, your heart pounding in your chest. His expression was serious, his green eyes searching yours like he was looking for something, anything, to tell him what you were thinking.
“What if…” you began, your voice trembling slightly. “What if this is something more? What if it’s not just… comfort?”
Dean’s gaze softened, and he reached up to cup your cheek, his thumb brushing gently over your skin. “I think… I think maybe it’s always been something more,” he admitted, his voice rough with emotion. “I just didn’t want to mess things up by saying it out loud.”
Your breath caught in your throat, and you felt a rush of warmth spread through you at his words. All the little moments, the touches, the way he held you close—it all made sense now.
“So, what do we do now?” you asked, your voice barely more than a whisper.
Dean’s thumb continued to stroke your cheek, his touch so tender it made your heart ache. “We figure it out,” he said softly. “Together. One step at a time. If… if that’s what you want.”
You nodded, leaning into his touch, your eyes never leaving his. “It is, Dean. It really is.”
A slow, relieved smile spread across his face, and he leaned in, pressing his forehead against yours. “Good,” he murmured. “Because I’m all in, Y/N. I want this, with you.”
And with that, the distance between you disappeared. Dean’s lips met yours in a gentle, lingering kiss that was filled with all the emotions you’d both been holding back for so long. It was soft, tentative, but it spoke of promises and possibilities, of something real and deep and lasting.
When you finally pulled back, you were both breathless, your foreheads still resting together, the world outside fading away.
“So, I guess our snuggles aren’t so platonic anymore,” you teased, a smile tugging at your lips.
Dean chuckled softly, his thumb brushing over your lips. “No, I guess not. But I’m okay with that.”
“Me too,” you whispered, your heart full as you wrapped your arms around him, pulling him close once more.
And as you settled back into his embrace, the line between friendship and something more blurred completely, leaving behind only the warmth of his arms around you, the steady beat of his heart beneath your cheek, and the certainty that whatever came next, you’d face it together.
Taglist: @roseblue373 @jc-winchester @hobby27 @mishreem
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fun-kyto-wn · 8 months ago
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I burned so long so quiet
You must have wondered if I loved you back
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I did,
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I did,
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I do.
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lamiasage · 8 months ago
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Men's
[HQ download and drawing process on my Patreon here!]
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dreampencil · 6 months ago
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Taking a break from my commission with a Destiel pencil sketch :) Taglist, please ask to be added or removed :)
@naughtystiel
@malicmalic
@fivefeetfangirl
@letmeblued
@castielsprostate
@dean-you-assbutt-cas-loves-you
@casdeans-pie
@pattywinchester
@bogwitchatrois
@bloodydeanwinchester
@beregond35
@horrorcas
@charlottemanchmal
@strawlessandbraless
@blue-eyed-cutiepatootie
@thefailcollection
@disabled-dean
@squirrelsarecool
@hauntedpearl
@markofcastiel
@butch--dean 
@rennerator
@sailorsally
@xofemeraldstars
@forkinthegarbagedisposal
@happilyfeatherafter
@universalcas
@riverwithoutbanks-art
@shutupjaff
@magnificent-winged-beast
@sanndh
@mrs-padalecki2341
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haircurlscas · 3 months ago
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and though i burn, how could i fall
when i am lifted by every word you say to me?
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