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The Arrangement - Chapter Ten (End)

Pairing: Dean x Reader

Summary: Two years have passed since you and Dean finally lay everything out on the table, a lifetime of love and friendship, and it's about time it's made official.

Word Count: 8.2k

Warnings/tags: Smut (18+) Fluff!! Emotions are high in this one! and a surprise ending...👀

AN: Alright guys! We have officially reached the end of this series! It's been a ride and I'm so grateful for those who stuck around till the end and rode this journey with me! 🥹 It was my first time writing a full series and I hope you guys enjoyed this as much as I have! 😭❤️ (gifs not mine, found on google)

P.S. This chapter was originally 3k… 😉

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Dean exhaled sharply, rolling his shoulders as he stood in front of the mirror, adjusting his tie for what had to be the hundredth time. The reflection staring back at him felt surreal—like he was looking at someone else. Someone settled. Someone whole.

He huffed out a quiet laugh, shaking his head. If someone had told him two years ago that this was where he’d end up—with you—he’d have called them crazy.

A knock at the door pulled him from his thoughts.

Sam stepped in, already looking dangerously glassy-eyed.

Dean smirked. “You gonna cry, Sammy?”

Sam huffed a laugh, shaking his head as he stepped forward, resting a hand on Dean’s shoulder. “Just… proud of you, man. And happy for you. You deserve this.”

Dean swallowed. He hadn’t expected the weight of the moment to hit quite like this, but suddenly, it did. All those years—the two of you orbiting each other, pushing and pulling, too damn stubborn to admit what was obvious to everyone else. For so long, he’d been afraid to want this, to believe he could have it. But now?

He shook his head, smirking. “Jesus, if you start bawling, we’re gonna have to seat you in the back.”

Sam laughed, shoving him lightly before pulling him into a tight hug. Dean clapped his back, holding onto the moment longer than he’d admit.

Then, the door swung open again, and the rest of his friends poured in—Benny, Cas, Gabe—all wearing varying degrees of smug grins.

"Well, well, well," Gabe drawled. "Look at you, all cleaned up and looking respectable. Never thought I’d see the day."

Dean rolled his eyes, but Benny clapped him on the back. “You ready for this, brother?”

Dean didn’t even hesitate. “Hell yeah.”

Then, the door opened one last time, and John Winchester stepped in.

The room quieted just slightly—not out of tension, but out of the weight that John always carried with him. His gaze swept over Dean, taking him in.

“How you doin’?” John asked.

Dean let out a breath as he smoothed his hands over the invisible wrinkles in his suit jacket. “Good. A little nervous, but… good.”

John nodded, stepping closer. His sharp hazel eyes softened as he studied his son, and after a beat, he shook his head with a quiet chuckle.

“You know,” John started, rubbing a hand through his thickening beard, there was more and more grey beginning to run through it now, “I knew she was the one the moment you brought her home.”

Dean huffed a little shocked. He never thought his father paid much attention to his relationships, unless Dean was asking for advise about something. John had always been the kind of father who seemed absent, out of the loop per se but, if you ever needed him, poof he was there.

“Yeah?”

John smirked. “Damn right. You trailed after that girl like a puppy since the moment you met her.”

Dean scoffed, shaking his head. “That’s not true.” It was. But Dean wasn’t about to admit that, he had to keep some dignity at least.

John let out a low laugh, glancing toward Sam, who was already grinning. “Oh, it is. Everyone saw it—hell, you’d look for any excuse to be near her. You’d act like it wasn’t a big deal, but soon as she walked in a room, you lit up like a damn Christmas tree.” He chuckled along with the other men in the room, and then added,

“And if she so much as smiled at another boy?” He blew out a breath, like it was the damnest thing. “You’d sulk for hours.”

Benny let out a laugh, and Cas muttered a “it’s true” whilst Sam and Gabe outright cackled.

Dean huffed, rubbing the back of his neck. “Alright, alright, let’s not turn this into roast-the-groom day.”

John’s smile lingered for a moment before he took a breath, his expression growing more serious. “You know, that’s how it was for me with your mom.”

Dean blinked, straightening slightly at the sudden shift in tone.

John nodded. “She had me wrapped around her little finger before I even knew what hit me. Still does.” His voice softened. “Women like that, they keep you on your toes. They challenge you, make you work for it. But, son, there’s nowhere else you’d rather be. Nowhere better to be.”

Dean swallowed hard, something thick settling in his chest. He didn’t think he’d ever heard his dad talk about his Mom like that—not in a way that was this raw, this honest.

John held his gaze. “You found something rare, Dean. Something worth everything.” He let out a quiet breath. “I’m proud of you, kid.”

Dean felt his throat tighten, but before he could find the words to respond, John pulled him into a firm hug.

It caught Dean off guard for half a second, but then he exhaled, sinking into it. His dad wasn’t a man of easy affection—not by a long shot—but when he did something like this, it meant something.

And it warmed Dean straight through.

John clapped his back before stepping away, clearing his throat. “Now, let’s get you married.”

Meanwhile...

You smoothed your hands over the fabric of your dress, breathing in deeply as you stood in front of the mirror. The reflection staring back at you barely felt real.

The dress was perfect—elegant but effortlessly you. Every delicate detail, every soft fold of fabric. It was another thank you to Jo and her wizardry in dress picking.

Your fingers brushed over the locket resting against your collarbone—the one that had belonged to your mother, the one Dean had returned to you. It was your something old, something borrowed, and as you held it gently, your heart ached with the weight of her absence. But there was comfort in knowing that a part of her was with you today.

Behind you, the room buzzed with excitement as all the ladies in your life gathered.

“Holy shit,” Jo breathed, eyes wide and a little watery as she took you in.

Charlie joined her, the both of them clinging to each other like proud aunts.

Jess, ever the romantic, clasped her hands together, beaming. “You look absolutely stunning.”

Mary stepped forward with a warm smile, adjusting your veil with careful hands. Her touch was gentle, but you didn’t miss the slight tremble in her fingers.

“You’re glowing, sweetheart,” she murmured, voice thick with emotion.

She lingered, taking you in with soft eyes. Mary had been like a third mother to you for as long as you could remember—always there with quiet wisdom, unwavering support, and a love that felt just as fierce as if you were her own.

“I’ve watched you grow into this incredible woman,” she continued, blinking back tears. “And I’ve always known—always—that you were meant for my boy. No one else could love him the way you do.” A watery smile pulled at her lips. “And God knows, he needs someone like you.”

Your throat tightened, emotion swelling in your chest.

Mary cupped your cheek, her touch featherlight. “I’m so proud of you. And I know, without a doubt, that you and Dean are going to build something beautiful together.”

You let out a small, shaky laugh, squeezing her hand. There was a nervous energy thrumming beneath your skin, but it wasn’t the bad kind—it was the kind that came with knowing something life-changing was about to happen.

Then, a soft knock on the door.

Ellen and Bobby stepped inside, and the moment Ellen saw you, she gasped. Her expression softened as she reached for your hands.

"You look beautiful, baby." Her voice wavered just slightly, and when you saw the glisten in her eyes, it nearly broke you.

Ellen Harvelle never cried.

But today, she did.

"You always were a handful," she teased, blinking rapidly as if to stop herself from full-on sobbing. "But damn if I ain’t proud of the woman you’ve become. How grateful I am to be your mother.”

You bit your lip, fighting back the wave of emotion threatening to ruin all of Jess’s hard work on your makeup. You squeezed Ellen’s hands. "I love you, mom."

"I love you too, sweetheart.” She pulled you into her arms, holding you tightly, and for a moment, you just let yourself be held.

Jess sniffled. "Damn it, you’re making me cry already!”

A collection of watery chuckles rippled through the room as you pulled back, watching Jess and the other women dab at their eyes. But when Bobby stepped forward, the laughter faded, replaced by something heavier.

He looked at you, and for the first time in your life, you saw him struggle for words.

“Ah, kid…” Bobby murmured, voice thick as he took you in. “Your mom… she’d be so damn proud of ya.”

Your throat tightened instantly, tears pricking your eyes for the millionth time that morning. You pointed at him warningly. “Nope. Don’t you do that. Do you know how long this took?” You gestured to your face in emphasis.

A chuckle rumbled from Bobby’s chest, but the warmth in his eyes didn’t fade. He stepped closer, squeezing your hand.

“I mean it. You’re gonna be the best thing that ever happened to that idjit. Not that he don’t already know it.”

A watery laugh bubbled from your lips. “Thanks, Dad.”

Bobby cleared his throat, shifting slightly. “Now, uh… before we go, I just need to make sure you’re sure about this. ‘Cause once you marry into that family, there’s no gettin’ out."

“It’s true.” Mary added with a shrug and a chuckle.

You smirked. "Well, damn. And here I was thinking I could just return him if I changed my mind."

Bobby snorted as everyone else laughed. "You’re stuck with him, sweetheart." He sighed, squeezing your shoulder. "But I gotta say… I don’t think he’d ever let you go, even if you tried."

Your heart clenched, warmth spreading through your chest, because you believed so too.

"You ready?"

You took a deep breath, exhaling slowly and then—

“More than ever.”

The first notes of Canon in D drifted through the air, soft yet powerful, carrying with them the weight of the moment. The murmur of the guests faded, the world narrowing to the centre aisle where one by one, your loved ones took their places.

Sam stood tall at Dean’s side, ever the loyal brother and best man, while your bridesmaids passed Dean with knowing grins. He barely registered them, too caught up in the pounding of his own heart, in the way his fingers curled and uncurled at his sides, in the anticipation buzzing in his veins.

And then—

The doors at the end of the aisle opened.

Dean sucked in a sharp breath.

There you were.

The world fell away, dissolving into a blur of nothingness. His vision narrowed, locking onto you as you stepped forward, arm looped through Bobby’s. Sunlight streamed through the windows, illuminating you like something out of a dream—his dream. And damn, if he didn’t feel like the luckiest son of a bitch alive.

You were stunning, but more than that, you were you. The same girl who had been his best friend for more than a decade, who had driven him crazy and made him laugh harder than anyone. The same woman he had spent late nights with on the couch, teasing and pushing each other, pretending you weren’t falling long before either of you admitted it. You were the one who knew him better than he knew himself, who had stood by him through every fight, every high, every low.

And now, here you were, walking toward him, about to be his forever.

His throat tightened. His chest ached with the sheer force of everything he felt. And it took him a second to realise—damn it, he was actually crying.

Bobby’s grip on your arm was steady, though Dean didn’t miss the way the older man’s fingers clenched just slightly, like he was holding on for one last moment. Bobby had been your rock, your father in every way that mattered, and today, he was giving you away.

When you reached the altar, Bobby turned to Dean, meeting his gaze with the kind of silent understanding only a father figure could give. His eyes softened, but there was steel beneath them—a warning, a promise.

"You take care of her, ya hear me?"

Dean swallowed hard, nodding with confidence as he told him, “always.”

Bobby gave your hand one last squeeze before placing it in Dean’s, stepping back with a small, gruff sniff.

The warmth of your touch sent a shiver up his spine, grounding him, steadying him.

You looked up at him as you stepped up to the alter, eyes shimmering, lips curving into a small, breathless smile. “Hi.”

Dean let out a quiet, shaky laugh, shaking his head as he drank you in. “My god, you’re beautiful.”

Emotion swelled in your chest, thick and overwhelming, and as you stared into his eyes. Those same green eyes that had been home for as long as you could remember. You knew, without a doubt, that this was exactly where you were meant to be.

Every step that had led you here—every late-night conversation, every argument, every kiss, every stolen moment—had been leading to this.

To forever.

The reception was already in full swing, the room buzzing with laughter and clinking glasses, but everything quieted when Gabe stood, a smirk already tugging at his lips as he raised his champagne flute.

"Alright, folks, settle in," he started, flashing a wink at you before glancing at Dean. "Now, I had a whole touching, sentimental speech planned—real tearjerker, would’ve had you all sobbing into your drinks—but then I thought… nah, let’s tell the truth instead."

A ripple of laughter swept through the crowd, Dean shaking his head while you rolled your eyes fondly.

"This story? This epic love story? It didn’t start with a grand romantic gesture, or some movie-worthy meet-cute. Nope. It started… with a dream." Gabe let the words settle before arching a brow. "And not in the chase-your-dreams kinda way—though, to be fair, there was some chasing involved."

Laughter rippled through the room, Dean groaning as he dropped his head into his hand.

"Yeah, yeah, we all know what I mean," Gabe continued smugly, clearly enjoying himself. "But let’s be real, this was always inevitable. It was clear as day these two were made for one another, the rest of us were just waiting for them to catch up. And when they finally did? Well, let’s just say… history was made. And, in some small way, I’d like to think I played a part in that. Y’know, a guiding hand. A little nudge. A subtle push toward the right direction."

Dean snorted. "Subtle, my ass."

Gabe ignored him, raising his glass higher. "So, here’s to them—two people who took their sweet time figuring it out, but who got it right in the end. To love, to laughter, and to the two luckiest people in the world."

The room filled with cheers and the clinking of glasses, and you turned to Dean, shaking your head.

"You still sure we shouldn’t have revoked his speech privileges?" you teased, despite the tears in your eyes.

Dean chuckled, pulling you closer. "Nah, he’s an ass, but he’s our ass.” You hummed in agreement and allowed Dean to pull you in for a sweet kiss.

Gabe clinked his fork against his glass again, clearing his throat dramatically. "Alright, lovebirds, enough of the mushy stuff, before you make us all sick. Let’s get to the part we’ve been waiting for." He shot a wink your way before grinning at Dean.

"Ladies and gentlemen, without further ado, it’s time for the bride and groom’s first dance!"

Another round of cheers erupted as Gabe lifted his glass in your direction, smirking. "Try not to step on her feet, Winchester."

Dean rolled his eyes as he stood, but then grinned down at you, taking your hand and guiding you toward the dance floor. Your heart pounded—not from nerves, but from the sheer overwhelming happiness swelling in your chest.

Then, the unmistakable opening chords of Ramble On filled the space.

You blinked, then let out a surprised laugh, shaking your head as you glanced up at him. "Seriously?"

Dean smirked, pulling you in close. "What? You really thought I’d let our song be anything else?"

You melted into him as he wrapped his arms around you, his hands resting warm and steady on your waist. The world faded, leaving just the two of you swaying together as Plant’s voice crooned through the speakers.

It was perfect.

From childhood best friends to navigating the tangled mess of emotions that came with your so-called arrangement. The night you finally admitted the truth—that you had always loved him. And whats more, so had he. You’d both been naive idiots thinking you could be anything other than this.

A year later, Dean had proposed.

He had done it under the stars in your father’s scrapyard, the place that had always been special to you as a kid, where you had felt closest to your mom. He had decorated it with fairy lights, roses, the whole nine yards, and when he dropped to one knee, looking at you like you hung the damn stars, you hadn’t even let him finish his speech before tackling him to the ground with your answer.

And now, here you were.

Your matching wedding bands, new but already familiar, warm against your skin.

Your arms around him, your heart pressed to his, exactly where you were always meant to be.

Dean pressed a soft kiss to your forehead, swaying with you in time to the music, his voice low as he murmured, "Took us long enough, huh?"

You smiled, tightening your hold on him. "Yeah," you whispered. "But we got here."

The song carried on, and as the tempo picked up, you felt Dean shift against you. His lips brushed your ear as he whispered, "You ready to really do this?"

Before you could ask what he meant, he pulled back, a devilish grin spreading across his face just as the beat kicked in. With a playful tug, he spun you out, making you laugh in surprise, and when he pulled you back, he didn’t slow down.

The two of you let loose.

Gone was the slow, tender sway. Instead, Dean twirled you, moving with an effortless ease that made your heart race for an entirely different reason. You chuckled, shaking your head at the fact Ramble on was your first dance song, but damn if it wasn’t so him—so you.

When the lyrics hit, Dean pointed straight at you, his voice loud and clear as he sang along, "I'm goin' 'round the world, I gotta find my girl—"

You didn’t miss a beat. Grinning, you sang right back, "I've been this way ten years to the day—"

The crowd erupted into cheers, the energy crackling through the room like wildfire. One by one, your friends and family got swept up in it—feet tapping, hands clapping, laughter spilling from every corner.

Charlie and Jo grabbed each other, twirling dramatically before rocking out to the familiar riffs, their hair flying as they head-banged in sync. Sam was pulled in by Jess, who grinned up at him with that determined look he never could resist.

Even Bobby, usually content to watch from the sidelines, let out a gruff chuckle before grabbing Ellen’s hand, the two of them stepping onto the dance floor like they’d been waiting for an excuse.

And then there was Gabe—fully committing to the moment, arms flailing, air-guitaring like his life depended on it. The sheer ridiculousness had you dissolving into laughter as you twirled in Dean’s arms, breathless, giddy, caught up in the rush of it all.

Your friends and family surrounded you, the circle growing tighter as the song surged on. Twirling, jumping, shouting the lyrics like you were at the best damn concert of your lives. It was wild. Chaotic. Perfect.

And through it all, Dean never let go of you.

No matter how much he moved, how hard he laughed, how off-key he sang, his hand always found yours. Always drew you back to him. Like he was tethered to you, like you were the one thing in the world he’d never lose sight of.

By the time the song came to an end, you were breathless, cheeks aching from smiling so hard. The room blurred around you, a hum of joy and celebration, but all you could see was him.

Dean pulled you close, his forehead resting against yours, his warm breath fanning across your lips as he panted slightly from the exertion. His green eyes, bright with mischief and something even deeper, locked onto yours.

“I love you, Mrs. Winchester.”

The way he said it—like he was savouring the words, letting them settle into his very bones—you knew he’d never tire of calling you that. And neither would you.

“And I love you, Mr Winchester.”

Dean’s smile was radiant, warmth and adoration shining in his gaze as he cupped your face, brushing his lips against yours in a kiss so soft, so reverent, it stole what little breath you had left. In that moment, with the music fading and the world narrowing to just the two of you, your heart felt impossibly full. Your soul, finally, was whole.

3 weeks later.

The soft sound of waves gently lapping against the shore blended with the distant chirping of tropical birds as the golden morning light seeped through the sheer curtains, casting a warm glow across the plush California king-sized bed.

A gentle breeze drifted in from the open window, carrying the scent of salt and sun-kissed sand, ruffling the gauzy fabric ever so slightly. The silky sheets were cool against your bare skin, a stark contrast to the lingering heat of Dean’s body beside you. With a contented sigh, you burrowed deeper, letting the warmth of the moment settle in your bones.

It had been a whirlwind since your wedding three weeks ago—an intoxicating rush of something long overdue. Of love, laughter and celebration with everyone who mattered most, all of which still echoed in your mind.

Unfortunately, reality had hit fast afterward, with both of you needing to dive back into work almost immediately, your honeymoon put on hold until the vacation days finally kicked in. But now, you were here. Just you and Dean. Together. Alone in paradise.

And what a paradise it was.

Ten glorious, sun-drenched days in the Maldives, tucked away in your own private villa perched over the crystalline water. The white sand stretched like silk beneath your feet, the ocean a dazzling shade of turquoise that shimmered under the endless blue sky. Every morning felt like something out of a dream, like waking up inside a living postcard.

You’d always imagined a warm, beachy destination for your honeymoon—Hawaii, maybe the Florida Keys. Something close, something simple. But you never expected this. Your parents and Dean’s had banded together, insisting you take your first trip as husband and wife international. A wedding gift so extravagant it had left you both stunned, speechless even.

Of course, you knew why you and Dean had initially opted to keep things local.

Your lips twitched at the memory of the exact moment Dean had opened the gift, his expression shifting from excitement to sheer, unfiltered dread. Because the Maldives didn’t just mean a long flight. No, it also meant taking a seaplane to reach the private island resort.

Looking at him now, utterly at peace, snoring softly beside you, his upper body bronzed from days in the sun, freckles scattered across his golden skin like constellations, it was almost impossible to believe this was the same man who damn near lost his shit on both flights. The contrast was almost comical.

Gone was the stiff, panicked man who had sat ramrod straight in his seat, white-knuckling the armrests like his life depended on it. The man who had hissed “This is a terrible idea” every time the plane so much as dipped slightly. The same man who, when faced with turbulence, had squeezed your hand so hard you were genuinely worried about circulation loss. And when the seaplane landed on the water? He’d practically kissed the ground the moment you stepped onto the dock.

Your heart ached in the best way as you thought back on the past week—warm sand between your toes, the taste of tropical cocktails, the lingering press of Dean’s lips against your sun-drenched skin. Late nights filled with soft laughter and slow kisses, tangled sheets as you celebrated your marriage in the best way possible.

It had taken you both a long time to get here, to this moment, but damn, were you happy.

Unable to resist, you swam through the sheets, moulding yourself against the familiar warmth of Dean’s body. Your fingers trailed across his chest, tracing over the scattered freckles like your own personal game of connect the dots, mapping out the skin you had come to know so intimately.

Your touch was light, teasing, before finally settling over the hand resting on his stomach, now adorned with the simple silver wedding band that matched the ring on your own finger. A symbol of forever.

Dean stirred as the soft press of your lips ghosted along his shoulder, trailing kisses up the strong column of his neck. A deep breath shuddered through him, his muscles tensing before melting into your touch. He shifted fully onto his back, blinking his tired eyes open, only to be greeted by the most beautiful sight.

The soft glow of morning light behind you, your hair tousled, your eyes sparkling with warmth and mischief.

That damn smirk of yours.

His lips curled up at the edges, but before he could say anything, you leaned in, continuing your path of lazy, unhurried kisses along his jaw, your mouth warm and soft against his skin. His breath caught when your teeth grazed his pulse point, the sharp contrast sending a thrill straight through him. His eyes fluttered shut again at the feeling, his breath coming quicker.

But then a thought, albeit fleeting, hit him. Why did this feel so familiar?

However, his grip tightened instinctively on your waist, heat blooming low in his stomach as you suckled at his skin and he pulled you up, crushing his lips to yours in a slow, searing kiss.

Your tongue caressed his, your touch sending fire through his veins, and then your hand slid down his abdomen—fingertips just barely grazing the hard planes of his abdomen, slipping beneath the sheets with agonising slowness.

And that’s when it hit him. Just like Déjà vu.

The dream.

This was exactly what he had pictured two years ago. The one thing that had shattered every illusion he had about what you were to him, the moment that had forced him to confront the truth—that he wanted you in ways he had refused to acknowledge before. That you were so much more than just his best friend.

It had led to The Arrangement. The realisation. The confession. Everything between then and now had stemmed from that dream.

And now, here you were. Not some figment of his imagination. You were real, you were his wife.

And this time, there was no rude awakening. No air horn. No sudden jolt back to reality.

Just you and your fingers curling around his hard length in a teasing grip, that had his breath stalling in his throat.

A dream literally come true. And damn, if this wasn’t a full circle moment.

“Fuck.” Dean huffed, head falling back against the pillows as your touch grew more purposeful, the whole thing made more intense by this little realisation. You tugged him softly, playfully, the pads of your fingers stroking his heated skin with an almost lazy confidence, and Dean let out a long, shuddering exhale.

“Jesus, sweetheart,” he groaned, one hand gripping the sheets while the other tangled in your hair. “Feels so good, baby.” You hummed in response, pressing wet, open-mouthed kisses along his jaw, then down his throat, your pace never faltering as you worked him, watching the way he came undone beneath you.

Dean’s stomach tensed when you suddenly slid lower, a slow, teasing descent, your mischievous gaze locked onto his as you kissed your way down his chest. He sucked in a sharp breath, his entire body thrumming with anticipation as your lips trailed lower.

“Shit,” he rasped as you reached his lower abdomen, your teeth grazing over the sensitive dip of his hip. His cock twitched in your grip, thick and pulsing with need, and you smiled against his skin, amused at just how wrecked he already was.

“You okay there, handsome?” you teased, your voice warm and sweet, a sharp contrast to the absolute sin in your eyes.

Dean let out a strangled chuckle, shaking his head. “You know what you’re doin’.”

“Mm. Maybe.” Your fingers tightened around him, stroking him once, twice, before your tongue darted out to tease the tip, swiping across the leaking head in one slow, torturous lick.

Dean’s hips bucked on instinct, a wrecked groan spilling from his lips. “Fuck—”

And then, without warning, you took him into your mouth, warm and wet and perfect, and his whole world tilted.

“Shit—baby—” His hand fisted in your hair as you hollowed your cheeks, taking him deeper, your tongue working him in a way that had his jaw clenching and his abs flexing beneath you.

You were relentless, sucking him down with slow, deliberate drags, your eyes locked onto his the entire time, like you wanted to watch him fall apart. And he was—fuck, he was unraveling at the seams, barely holding onto control.

“You’re too good at this,” he rasped, his fingers tightening their grip in your hair. “So goddamn good. Fuck—gonna make me—”

But before he could lose himself completely, he forced himself to move, a growl ripping from his throat as he reached down and hauled you back up, capturing your mouth in a desperate, heated kiss.

“Not yet,” he murmured against your lips, his voice thick and rough, still breathless. “Wanna taste you, sweetheart.”

And then, in one swift motion, he flipped you onto your back, hovering over you, his lips trailing down your body, kissing, worshiping, taking his time to appreciate every inch of you.

His hands spread across your thighs, parting them, his breath hot against your skin as he settled between them. His mouth found your inner thigh first, teasing, his teeth grazing your sensitive flesh just to hear the way your breath hitched.

“Dean,” you whimpered, your hips shifting beneath him.

He smirked, dragging his lips up, and up, until he was right where you needed him. “Relax, sweetheart.” His voice was low, rough, filled with promise. “Lemme take my time with you.”

And he did.

He pressed a soft, lingering kiss against your clit before dragging his tongue through your folds, slow and deliberate, savouring you, his hands gripping your hips as he pinned you down, determined to make you feel everything.

You gasped, your fingers threading into his hair, your back arching off the bed as he worked you open with his mouth—licking, sucking, teasing, his tongue flicking against your most sensitive spot until you were trembling beneath him.

“Dean—”

“That’s it, sweetheart,” he murmured against you, his voice thick with hunger, dark with raw need. “Let me hear you.”

And so you did.

You didn’t hold back.

You cried out as two thick fingers slid deep into your dripping cunt, curling just right—hitting that devastatingly perfect spot he had long since memorised, learned by heart just to ruin you over and over again. Your back arched, muscles clenching as he pumped them in and out, each stroke dragging a fresh moan from your lips.

His mouth came away from you, slick with your arousal, his focus now solely on his hand as he fucked you with his fingers, determined, relentless. His wrist flexed, his pace quickening, the wet, obscene sounds filling the room.

Your thighs trembled violently, your body caught between the unbearable pleasure and the overwhelming pressure coiling deep in your core, rising fast, too fast.

“I know, baby,” Dean groaned, his free hand gripping your thigh, holding you wide open as you writhed, instinctively trying to fight what you knew was coming. “Don’t run from it. Let it happen. Give it to me.”

The raw command in his voice shattered you.

With a strangled cry of his name, your orgasm slammed into you, white-hot, electric, tearing through every nerve in your body. Your release poured out of you, soaking his arm, drenching the sheets beneath you. The sheer force of it left you shaking, gasping, completely wrecked beneath him.

And Dean all but growled.

“Jesus Christ,” he rasped, dragging his fingers from your pulsing cunt, watching in fascination as your slick dripped down his wrist. He lifted them to his mouth, keeping his gaze locked onto yours as he sucked them clean, groaning at the taste.

“Fuck, baby,” he murmured, his voice thick with admiration and something darker, something purely possessive. “Every time… I swear, it just gets better.”

Heat flushed through you, but the shame that once crept in at moments like this was gone.

Dean had stripped it from you, erased it with every moan, every praise, every time he worshipped the way your body responded to him. He loved this. Loved dragging you over the edge so hard, so deep, that you couldn’t hold back. Loved watching you come apart, seeing the proof of how fucking good he made you feel.

And fuck, did he make you feel good.

You swallowed, watching as he smirked, his hand gliding up your trembling thigh, rubbing soothing circles as he took in the mess between your legs like the goddamn masterpiece it was.

“So fuckin’ pretty,” he muttered, trailing his fingers through your slick folds, groaning at how sensitive you still were. His cock twitched from where it was trapped against the mattress. “And already dripping for more.”

You bit your lip, eyes half-lidded with need, your body still molten, still buzzing, but the hunger in his gaze sent another sharp pulse of arousal straight to your core.

“C’mere,” you murmured, crooking a finger at him, and Dean obeyed instantly, moving up your body with a predatory grace until he was caging you beneath him, his forearms bracketing either side of your head.

You grabbed the back of his neck, yanking him down for a kiss that was all tongue and teeth, desperate and messy. You moaned into his mouth at the taste of yourself on his tongue, the way he devoured you without shame. Your legs wrapped around his waist, heels digging into his lower back, tugging him closer, needing him now.

Dean chuckled against your lips, low and husky, cocky as ever, but fuck, he loved you like this—needy, impatient, desperate for him. He rolled his hips, his thick cock gliding through your soaked folds, coating himself in your slick, teasing you both with the friction.

“Dean,” you whined, your nails biting into the firm muscles of his back.

He groaned, his head dropping into the crook of your neck. “Goddamn, baby—”

You whimpered as the head of his cock caught at your entrance, your whole body arching, pulsing, silently pleading.

“Baby, please,” you breathed into his ear, your voice drenched in pure want.

And fuck—Dean couldn’t deny you anything when you begged like that.

With a deep, shuddering breath, he tilted his hips and pushed in, inch by glorious inch, stretching you open, filling you to the brim.

A guttural groan ripped from his throat as he bottomed out, buried to the hilt in your tight, throbbing heat. His forearms trembled where they held him up, his jaw clenched as he fought for control, fought against the primal urge to pound into you, to take you the way he needed to.

“Jesus Christ,” he gritted out, his forehead dropping to yours. “You’re perfect.”

You gasped, your walls fluttering around him, nails dragging down his back, your body begging for more.

“Fuck me, baby,” you pleaded. “Please—”

And with that, he was gone.

All restraint shattered.

Dean fucked you, deep and unrelenting, hips snapping against yours with a rhythm that had you keening, moaning, gasping his name like a prayer. His hands were everywhere—gripping your hips, sliding up your stomach, palming your breasts, fingers finding your throat, owning you.

He growled against your lips, biting at your bottom one as he pulled back, eyes dark, feral. “This what you needed, sweetheart?”

You couldn’t even form words, just nodded frantically, lost in him, in the overwhelming pleasure he wrung from your body with every deep, punishing thrust.

“Goddamn, you’re so good for me,” he groaned, voice wrecked, his pace growing erratic as he felt you tightening around him, pulling him deeper. “Gonna come for me again, huh? Gonna soak my cock this time?”

You sobbed, your entire body trembling, on the edge of bliss so sharp it made you ache.

Dean reached between you, his fingers finding your swollen, neglected clit, rubbing tight, desperate circles.

That was it.

That was fucking it.

Your climax crashed over you, stealing every last bit of breath from your lungs, and you screamed his name as your walls fluttered around him, squeezing him like a vice, milking him for everything he had.

Dean groaned, long and deep, his hips stuttering, his body locking up as he spilled into you, filling you with everything he had, holding you tight, panting against your sweat-slicked skin.

For a long moment, neither of you moved, just lay tangled together, bodies trembling, completely spent.

Dean finally let out a slow, satisfied breath, brushing damp hair from your forehead as he kissed you, slow and deep, nothing but pure devotion in the way his lips moved against yours.

“God, I love you,” he murmured between kisses, voice hushed and reverent, as if the words themselves weren’t enough to contain the depth of what he felt.

Your heart fluttered, as it always did when he uttered those three words, and your arms around his neck tightened, holding him closer.

“I love you too,” you whispered, pulling back just enough to meet his gaze, your fingers ghosting over his cheek. His green eyes softened as he leaned into your touch, letting out a contented sigh before turning his head to press a lingering kiss to your palm.

And then a quiet huff left his lips as he dropped his head onto your chest, the weight of him grounding you, comforting in a way you could never quite put into words. Without a second thought, your fingers drifted into his sweat-slicked hair, combing through the damp strands, soothing him as exhaustion slowly pulled you both under.

“I can’t believe this will be our last night here,” he mumbled into your skin, his voice thick with sleep.

You hummed in agreement, a pang of sadness settling in your chest. This place, this little bubble you’d created together, had felt like a dream—one you weren’t quite ready to wake up from.

“Maybe we should just move here,” you murmured playfully, a small smile tugging at your lips. “Quit our jobs and stay forever.”

Dean let out a lazy chuckle, his breath warm against your skin. “Don’t tempt me.”

You pressed a kiss to the top of his head, feeling him snuggle closer, his breathing deep and even. Within moments, sleep, once again, claimed you both.

A couple of hours later, the sharp grumble of your stomachs had dragged you both from your unplanned nap. The two of you groggily peeled yourselves from the tangle of sheets, reluctantly leaving the comfort of your bed to shower and dress.

The day passed in a slow, blissful haze—lounging on the terrace, nibbling on fresh fruit and pastries, talking about home, about work, about everything and nothing at all.

As the evening approached, you had one last dinner reservation at the resort’s restaurant. Dean opted for a quick dip in your private pool while you got ready, the sound of water rippling as you slipped into a white, flowy sundress, the light fabric brushing against your ankles. You left your hair down, the soft waves cascading naturally over your shoulders—just the way Dean liked it. A touch of mascara, a swipe of lipstick, and you were ready.

“You look beautiful,” Dean’s voice was thick with appreciation as he appeared behind you in the mirror, his reflection stunning—his hair damp, torso bare and glistening with droplets.

You bit your lip, heat pooling in your stomach as he trailed his fingers over your exposed shoulder. Respectfully, he refrained from pulling you flush against him—knowing he’d soak your dress—but he still pressed a slow, lingering kiss to your skin.

Dean winked before stepping back, and with zero shame, dropped his shorts, giving you a perfect view of his delectable peach of an ass. He caught you staring as he looked over his shoulder, and with a cheeky grin gave his own firm cheek a light smack before stepping to the shower.

You were still giggling and shaking your head as you slipped on your sandals.

The restaurant was breathtaking—an open-air dining space set against the endless stretch of ocean, the sky painted in fiery hues of orange and pink as the sun melted into the horizon. Soft lanterns swayed gently in the evening breeze, casting a golden glow over the wooden tables adorned with crisp white linens and delicate floral arrangements.

The scent of salt and grilled seafood hung in the air, mingling with the distant hum of waves rolling onto the shore and light spoken conversations from the other guests.

Dean pulled out your chair for you before settling into his own across from you, already reaching for the menu with a familiar furrow of his brows.

“You know, we’ve been here all week, and I still don’t know what half this stuff is.” He let out a huff, rubbing a hand over his jaw. The two of you had tried different restaurants around the island, and while the menus varied, the dishes always seemed to push him slightly outside his comfort zone.

You giggled, shaking your head before deciding to take pity on him. “How about the steak?” You leaned over, tapping the menu where the 8oz fillet with sautéed potatoes was listed. “It’s about as close to a burger and fries as you’re gonna get.”

Dean followed your finger, eyes scanning the description with renewed interest before nodding. “Alright, yeah. I can work with that.” He flagged down the waiter, ordering you both a beer along with his steak, while you opted for grilled salmon with fragrant coconut rice.

When the food arrived, Dean eyed his plate warily, poking at the steak as if it might bite back. Clearly not used to the meat un-minced and patty-like. He cut into it, taking a tentative bite, chewing slowly as he mulled over the flavours.

“Well?” you prompted, watching him closely, lips twitching.

Dean let out a low hum of consideration. “It’s… not bad.”

You let out a laugh. “That’s practically a glowing review from you.”

He rolled his eyes, but a smile played on his lips. “Hey, I like what I like.”

Still, he indulged in the experience, even letting you feed him bites from your own plate after some playful coaxing. He’d grumble about it, but the way his eyes flickered with enjoyment every time he took a bite of your dish didn’t go unnoticed.

The night carried on in soft conversation and easy laughter, the warm glow of the lanterns reflecting in his eyes. And through it all, his gaze never strayed far from you—watching, adoring, committing this last night to memory.

Back in your villa, the island's natural warmth was thick in your hut with the scent of salt and jasmine as you pushed open the patio doors. Behind you, a familiar melody drifted through the space—the soft, unmistakable chords of Your Song filling the air as Dean messed with the vinyl player. The resort seemed to be a big fan of Elton, you'd noticed.

You smiled at the song choice, turning just as he held out a hand, a boyish grin tugging at his lips.

“Dance with me?”

Your heart melted, and without hesitation, you slipped your hand into his, letting him pull you close. His hands settled at your waist, yours looping around his neck, and he swayed you both to the slow rhythm. His chin rested atop your head, his fingers tracing lazy, absent patterns along the small of your back.

The gentle hum of Elton John’s voice wrapped around you both, the moment steeped in quiet affection.

“I hope you don’t mind, that I put down into words…” Dean sang along to the chorus, his voice soft and deep, trailing off as he smiled down at you.

“How wonderful life is, while you’re in the world,” he finished, his gaze holding yours, warm and full of something that made your chest ache.

Just as you rose on your tiptoes, he wasted no time meeting you halfway, capturing your lips in a kiss—slow and deep. The warmth of his body, the press of his hands against you, the way he kissed you—it all built into something deeper, something more desperate.

But then—

A sharp pang shot through your stomach.

You froze, your breath hitching. Then, it twisted, turned, and a wave of nausea slammed into you so suddenly, you barely had time to shove Dean back before sprinting to the bathroom.

“Shit—sweetheart?”

Dean was at your side in an instant, gathering your hair as you lurched over the toilet, emptying your stomach. His warm hand rubbed slow, soothing circles over your back, his voice laced with concern.

“Do you think it was the food?” he asked, frowning.

You let out a weak breath, wiping your mouth. “Maybe,” you murmured, though doubt crept in. If it was the food, wouldn’t Dean be sick too? He had shared bites of your meal, after all. However, another wave of nausea hit you and had you hugging the toilet bowl once more.

You spent the rest of the night curled on the cool tile floor, Dean refusing to leave your side. He wiped your clammy forehead, whispered reassurances, cradled you against him when you finally had nothing left to give.

By the time the early morning light filtered through the windows, you were drained, barely able to crawl into bed.

When you woke a few hours later, your body was still heavy with fatigue, your stomach uneasy, but you managed to push through, packing sluggishly as Dean went to check out.

You were in the bathroom, collecting your toiletries, when your gaze landed on something that made your breath hitch.

Your box of tampons.

Unopened.

A strange, uneasy feeling settled in your chest as you stared at it. Slowly, you did the math in your head, counting back the days, trying to recall the last time you’d needed them.

Two weeks late.

Your stomach flipped—not from nausea this time, but from something far more terrifying.

No. No, it was impossible.

You were on the pill. You took it religiously.

But they aren’t always foolproof, your annoying voice of reason argued.

A sharp breath left you as you stared at the box, heart hammering in your chest. However, a thought hit you. You remembered finding it on your first night here.

Rummaging through your toiletry bag, you exhaled in relief when your fingers brushed against it. A pregnancy test. One Charlie had slipped in as a joke—a homage to her annual Twilight binge—thinking she was hilarious. And right now? You were thanking her ridiculous sense of humour.

“Right. You’re just being irrational,” you whispered, trying to calm yourself. “You just ate something bad and your body rejected it. It’ll be negative and you’ll feel real stupid for freaking out over nothing.”

Your fingers fumbled with the packaging as you ripped it open, barely noticing the way your hands shook. Luckily, you needed to pee anyway, and with a deep, steadying breath, you settled onto the toilet, slipping the stick between your legs.

When Dean returned, the sight of your half-packed suitcase made his stomach tighten. You weren’t in the main room where he’d left you.

Had you gotten sick again?

The thought unsettled him. He’d spent the entire walk back hoping last night had been a fluke—that you wouldn’t suddenly take a turn for the worse, forcing him to figure out where the hell the nearest hospital was on this island.

You looked better this morning. Tired and a little pale, but no vomiting. No fever. That had been enough to ease his nerves—until now.

Then, he saw the bathroom door slightly ajar.

Quietly, he stepped forward, pushing it open. You were sitting on the edge of the bathtub, head down, shoulders tense.

“Hey, is everything o—” His words died in his throat when his gaze landed on the object grasped tightly in your hands. A little white stick.

His heart spiked.

At the sound of his voice, you looked up, eyes wide and alarmed, not easing his nerves at all.

“Dean,” your voice wavered, barely above a whisper. “I’m pregnant.”

AN: Now... I have a confession. I had originally ended this at the wedding, but inspiration struck. And maybe stubbornness to finish up with these two. So the honeymoon was added and thus the premise to... *drum roll*... The Predicament. A sequel series that will follow Dean and the reader becoming parents. That's right! This isn't the last of this pair. 🤪 Also want thank you all so much for reading and sticking with me throughout this series! I hope you're all excited for another adventure with these two! 💙

Dean Winchester/Series Tag List:

@bettystonewell , @nancymcl , @happyfxckinghorrors , @ambiguous-avery @jollyhunter @tbgfvfdcb @crooked-haven @chevroletdean @paganvamp @stoneyggirl2 @deans-baby-momma @spnaquakindgdom @ladykitana90 @lyarr24 , @impala67rollingthroughtown @jackles010378 @riteofpassage77 @spnaquakindgdom @cevansbaby-dove @shadysoulangel @piptoost @star-yawnznn @deansimpalababy @megara0224 @hobby27 @idontwannabehere78 @maddie0101 @kr804573 @shadysoulangel @mrs-nesmith @zepskies @ohheyguyss @suckitands33 @ultimatecin73 @mishkatelwarriorgoddess @arcannaa @aylacavebear @bobbdylann @jaredpadonlyyyy @waynes-multiverse @impala67stellawinchester @bonbonnie88 @youroldfashioned @iloveeveryoneyoureamazing @bejeweledinterludes @rach5ive @ladysparkles78 @globetrotter28 @kayleighwinchester @amberlthomas

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