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jollyhunter · 1 month ago

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24 Kinky Days with Dean x reader - Day 22.

Pairing: Dean Winchester x fem!reader

Warnings: NSFW - MDNI! - includes explicit sexual content, Dean being naughty and goofy, teasing, praise kink, bit of fingering, a lil' spankin', biting, oral (f receiving), unprotected p in v (wrap it before u tap it!), softdom!Dean, Dean guiding you through a new s♡x-position, fluff, aftercare and also there's pizza (yes, that's a warning) - no use of Y/N - there's probably more so just let me know if I missed something - English is not my native language and I’m dead on my feet Contains brief reference to Dec.9 (Whip Stroke) and Dec. 16 (Roll Over Rule)

Summary: Your ideas of 'self-care' couldn't be more contradicting: Dean's craddling a pillow and munching on his cold pizza, while you go through your yoga routine next to the motel bed. The entire time he's watching you stretch and bend and arch your back with lingering eyes... until he decides you've had enough yoga. Time for a 'fun way' to relax.

Words: ~6,500 (yeah, I know, prepare for a lot of teasing, but it'll pay off)

Feedback and reblogs are highly appreciated! Let me know in the comments what your favorite part was! <3 A/N: At this rate, I give up on the order of the prompts / days. 🥲 But I definitely want to complete the challenge! (Sorry for the long wait y'all!)

22nd Dec. - Yoga, Kama Sutra - potato, potahto

“Of course pizza beats yoga.” Dean scoffs, his eyebrows pinched together with a lazy shake of his head in disbelief. Like the audacity of you even questioning the superiority of fast food? Unbelievable.

“But- how can you even compare the two? That’s junk food. And this is like…” You think for a moment until you remember the right term, “Self-care. You should try it once.” You try to argue in hopes that this conversion might still turn to your favour. But you know you’re pulling on threads by now.

“Oh I do self-care.” He retorts gruffly, his eyes flickering down at you. And to proof his point, he stuffs a big bite of pizza into his mouth, munching on it while he continues, his words halfway muffled, “Food and beer’s my self-care, baby.”

“But-” You groan with a roll of your eyes but stop yourself there. If that man wasn’t halfway as fit as he is, you’d at least still have the trump card of health factor left. But truth be told, despite that, you didn’t have any more arguments, and you both knew it.

So in Dean’s eyes that settled it. His way of self-care is superior to yours. End of discussion.

His focus shifts back to his pizza and the old TV boxed in by a pair of wooden chairs. The smell of cold junk food mingles with the musty carpet that's infiltrating your nostrils everytime you get a bit closer to the floor. Gratefully the sweet cinnamon smell of one of those Christmas candles you had lit the moment you returned to your room, covers up most of the motels stale stench.

After Dean has been channel zapping through various Christmas movies, he finally gave in and tossed the remote control aside on the bed. The TV is running some ads in the background now and Dean is on his stomach stuffing his face with pizza, while you are on the ground next to the motel bed, doing your yoga session on a mat. "To relax," as you had explained to him. "Desperately needed after this case had turned out to be a damn goose chase all along." You added. And on top of that, the hard mattress you had to put up with for the past week did little to ease your bad mood or aching back pain.

By now, Dean had become used to your sporadic yoga sessions whenever time allowed it. Although it was still a mystery to him how this ‘weird hippie stuff’ was in any way relaxing to you, he always enjoyed watching you. And he’d made it a habit of his own to comment with a lick over his lips – perhaps even a low, appreciative whistle – and shamelessly lustful eyes taking in every detail of your body as you’re going through your routine, “Have I ever told you how lucky I am? Like jesus – you’re so fuckin’ flexible. Like some friggin’ contortionist. I bet you can even hook your foot behind your head.”

So, naturally, Dean isn’t really paying any attention to the TV. Even though the intro sequence of “Die Hard”, one of his favourite movies, is now playing.

As always his eyes are lingering on your stretchy outfit and how tightly your favourite colour wraps your body, highlighting every curve of yours, no matter where. The thin shimmer of sweat on your exposed skin and the way you seemed so in control and at the same time at peace. To him it felt like a big contrast to the moments of action where you’d cut down a vamp or plunge a stake through a pagan’s ribcage, your movements quick, precise and face and clothings always covered in the red aftermath.

He takes another bite of the pizza, attempting to distract himself, but his gaze keeps drifting back to you. Your rear in the air now as you switch into the Downward Dog pose. The soft moans and heavy breaths that slip your lips makes him chew slower. His mind now imagining you arching your body in other ways rather than yoga moves, while moaning his name and – Damnit, Winchester, get your mind out of the gutter.

“You having fun up there?” Your teasing voice rips right through his rather explicit picture of him going through some yoga poses with you at his mercy and he almost chokes on the mouthful of pizza. He forces it down with a swig of beer, while he gathers his thoughts sufficiently to reply with a cocky smirk, “Just enjoying the view.”

“Of course you do.” You roll your eyes but can’t help a soft chuckle before you switch to another pose.

From the corner of his eyes, he watches how you effortlessly stretch your legs apart just to roll over onto your stomach where you continue with propping yourself up on your hands, arching your back and then tipping your head back while pressing your stomach into the mat.

“Tell ya what,” he suddenly speaks up before he interrupts himself, stuffing the rest of the pizza crust into his mouth and swallowing it down. “You could probably do the whole Kama Sutra without breaking a sweat.”

You hold the Cobra pose when your chest briefly heaves from the huff that slipped your nose. “Horn dog.”

“Yoga, Kama Sutra – potato, potahto.” He snorts with a mocking tone, clearly starting to get annoyed from his fruitless efforts to distract you so far.

He shifts on the bed, propping his head up on the pillow in the crook of his arm to get a new angle on your curves. After watching you for a moment, he decides it’s time for a new approach.

He clears his throat before he muses in a sultry tone, “There’s also better ways to relax than yoga.”

While he licks his greasy fingers clean, he can’t help but appreciate the way the tight fabric of your yoga pants stretch over your curves again.

Still playing deaf, huh? A playful Cheshire smile forms on his lips when he finishes to suck his last digit with a obscene pop. He then continues in a demanding voice, “C’mere.”

“I’m not done yet.” You reply curtly, muffled slightly by the mat, your head now dropped down with your forehead resting on your folded hands.

He lets out an amused hum, “Oh yes you are.”

Within seconds he rolls off the motel bed to move on top of you, straddling your thighs and pressing down on you, pinning you against the mat.

You let out a surprised gasp, “Dean!”

But the only response you get is a cheeky “Heh-heh”.

When you feel his warm hands cup your butt cheeks and starting to squeeze and massage them, you lift your head to glance back over your shoulder at him. You give him your warning ‘seriously now?’ look, which he just deflects with a mock-innocent grin of his that said ‘what?’.

The way his palms squeeze firmly against your butt cheeks makes him let out a low satisfied hum in his throat. One hand moves to rest next to your head, supporting him as he leans down. His breath’s hot against your ear when he mutters, “This’ a lot more fun than that bullshit yoga.”

You want to bite back with a snarky comment about it not being bullshit at all – but your thought gets cancelled the moment his lips brush over the sensitive skin behind your earlobe, tracing a path of open mouthed kisses along the side of your neck. You let out a low shuddering breath, instinctively tilting your head for him.

But then a waft of his junk-food-slash-beer-laced breath hits your face and it instantly makes your nose scrunch up in a cute fashion.

“De, you smell like a dumpster.” You chuckle and reach with your hand over your shoulder to playfully shove his face away.

“Oh yeah?” He retorts with a smirk. Meanwhile his free hand snakes to the inside of your thighs, tight fingers sliding up under the stretchy fabric of your yoga shorts.

“Huh… only one way to solve it.” He mutters before he nips at your hand which had been pushing his face, giving the tip of your middle finger a short sharp bite that makes you gasp and immediately pull away.

He chuckles at your reaction and then straightens up to sit back on your legs. He inches further down to your calves, his eyes darting from his fingers wiggling under your short pants, up to your face again with a smirk on his lips. “I know what you’re thinking, sweetheart…”

Your anticipation’s building quickly. Feeling his fingers tracing so teasingly along the rim of your panties made the heat pool in your stomach and your mind throw all other plans for your remaining yoga session out the backdoor. And he damn well knew it the moment he brushed against the damp stain in the centre of your thin patch of fabric.

But then you let out a frustrated huff. He’d suddenly pulled his hand from between your legs to pat your ass with it, his glinting emerald eyes never leaving yours as he continues with a drawled “Nuh-uh.”

Then he leans over to the bed, his hand sliding into the pizza box where he fishes a remaining slice out. “Open wide.” He orders with a grin as he reaches with his hand over your shoulder. There he prods the tip of the pizza slice against your cheek, “C’mon, down the hatch. Commit a sin for me.” He quips with a feigned serious tone.

When you still look at him with that expression of befuddlement, he chuckles, his grin widening, “Take a bite, sunshine. Your breath’s my breath.”

You’re torn between being turned on by his words in some dirty twisted way and being utterly amused by them. It’s not like you were on a diet – heck, you sometimes eat so much junk food with all the cheap diners you’d hit every day on the road, it was a damn miracle you hadn’t gained weight yet.

“C’mon, Say aaaah.” He hums, still grinning from ear to ear as he prods the pizza slice against your lips.

After an amused snort, you can’t help but crack a grin of your own, “You’re a silly man, Winchester, you know that?” You finally give in and open your mouth enough to take a bite of the cold salami pizza.

“Yeah, but I’m your silly man.” He replies as he discards the pizza slice back into the box.

You swallow the bite down when his finger swipes over your bottom lip to clean away a streak of tomato sauce. His eyes follow his thumb’s movement, his touch gentle but the expression on his face more mischievous when he watches the tip of your tongue licking out to chase his finger to catch the bit of sauce.

You hold each other’s intense gazes, eyes darkened with something more. The sudden shift in atmosphere had you both still in your movements, taking in how the air between you had suddenly charged up.

Dean finally can’t take the tension any more and lets out a low growl from the back of his throat. He withdraws his finger, before giving your cheek a soft pat. “There’s my good girl.”

Your lips curl into a proud smile at his praise, “Only for you.”

A soft chuckle slips over his lips as he straightens up to sit back on your thighs again. His hands run down your back until they wrap around your hips, fingers trailing the hem of your yoga shorts. He hooks his fingers into the elastic band, slowly starting to pull them over your butt cheeks.

Your breath hitches when the cold air makes contact with your exposed rear. Next moment you feel his teeth dig into the soft flesh of your left bum cheek which triggers a short surprised yelp of yours.

“It was just too tempting.” He chuckles against your skin before he lets go of your butt with a wet-smooch to the red mark and straightens up again.

He pats the spot where he’d just claimed you, with his hand, “Lift up your hips, sweetheart.”

As you wiggle underneath him, he gets up on his knees, his weight now lifted off you to aid you with it. He leans forward to get a better hold on the fabric to properly pull the yoga pants along your panties down towards your knees.

“There we go… Now hold still for me, sunshine…” He mutters while his hands move along your skin.

A shiver runs through your body as you feel the only thing between you and him being taken from you, how you feel the fabric brush down your legs until you are completely exposed for him. Exposed and at his mercy. And damn it made your breath hitch from feeling vulnerable, as much as excitement.

After his hands had traveled further down, taking your pants and underwear with him, he discarded the redundant pieces of clothing to the side.

Finally satisfied, Dean slides down your legs again until he’s sitting on your calves, his hands on the back of your thighs. “Now where was my good girl’s cute little butt again.” He comments as he gently palms the soft globes of your cheeks with his smile never leaving his lips.

You groan softly and your eyes flutter closed, your body practically melting into the yoga mat under his touch.

“Oh, right, there it is.” He squeezes, his large hands massaging the flesh before he suddenly gives you a firm spank.

“Jesus-!” You yelp up at the unexpected sharp smack, your eyes wide open now as you whip your head to the side to stare back at him.

“Hey, you’re in prime spanking position here. What am I supposed to do, just admire the view and do nuthin’?” He mutters behind a teasing chuckle, his green eyes glued to the spot on your butt that was now slowly turning a light shade of red where his palm had hit you. “Plus, I know ya like it. Or you want me to get out the leather crop and remind you of our spankin’ session last week?”

Your thighs twitch involuntarily at the reminder of that evening. And the heat in your core is tingling from the vivid memory of that sweet-burning sensation that had taken over your body every time the leather smacked down on your skin.

“Guilty as charged.” You mutter while you have to force a moan back down your throat.

Dean’s lips curl into a cocky grin, “Knew it.”

You playfully narrow your eyes at him as you glance back over your shoulder to keep an eye on his sinful hand. But Dean stays unperturbed, if anything, your warning look just spurs him on even more.

“That’s for looking too damn good in those tight-ass yoga leggings.” He continues, giving your butt another firm slap before he reaches between your legs and your breath catches in your throat. His thumb traces the outline of your dripping folds, “And this-” His fingertips just graze over your centre, “That’s for being my good girl.”

He takes a moment to enjoy your gasp and how your head had dropped to the mat, your breath shaky already. His tongue darts out to lick his lips before he orders in a more gravelly tone, “Now be a good girl and spread your legs for me. I need to taste you.”

A shuddering exhale leaves your mouth, followed by a curse that luckily gets swallowed by the yoga mat you’re breathing into. You bend your knees slightly outward, as far as his hips pinning down your calves allow you to go.

“That’s it sweetheart…” He murmurs before his large hands grab the inside of your thighs, guiding your legs to part even further while his head slowly starts to sink down between them.

Your thighs begin to shiver from his warm breath hitting your soaked slit, desperately begging for his attention. Your hands blindly search for the edge of the mat, your fingers clutching it on each side as you prepare for him to dig into you.

Dean of course notices your anticipation and can’t miss the chance to comment on it.

“You’re gonna grab that mat nice and tight for me, sunshine. And you’re gonna hold still, keep those legs spread, and stay nice and quiet.” He instructs, his tone taking on a more commanding one, but still with a mischievous edge to it.

He then lowers his eyes again to admire the slick flesh between your legs where your folds are already parted, practically gleaming in the dim light of the motel room.

“Damn, look at you all nice and wet and open for me.”

Dean shifts his weight to brace his left elbow on the floor next to your hip, the other hand splayed out on the small of your back to hold you in place.

“You’re like a damn waterfall already, sunshine.” He murmurs in awe. The way your body reacts to him never ceases to fascinate him. He leans in, and you feel his hot breath coming in short puffs as he places a gentle kiss on your hooded clit, before he pulls back again.

As you immediately lift and tilt your head to look at him, he lets out an amused hum, “Now now, head down, sweetheart. Remember, yoga’s about relaxing and focusing on your body.”

“Smartass.” you manage to groan out.

“Eatsass.” he corrects you and before you get to be smart with him again, he proofs his point by suddenly parting your slick folds with his tongue, drawing it all the way up until he pulls it back into his mouth with a smack of his lips.

A low moan ripples through your chest, finally feeling that long desired friction that has you melt into a puddle of a blubbering mess. “Please- Dean- don’t stop- I need more- please-”

He grins at your pleading words and dives right back in. Licking, prodding, tongue lapping across your glistening folds, drinking your juice like its the only thing that keeps him sane. He moves up, his tongue circling your clit before he wraps his lips around it. Your legs suddenly tense up and a pathetic mewling-yelp erupts from your parted lips when he starts to suck at your bud like he’s finishing off a flurry through a thin straw.

Your hips jerk back and involuntarily try to pull away from the onslaught. But in vain as his large palm presses down on the small of your back to keep you in place and in reaction to your attempted escape, he just increases the borderline painful pull on your clit even more.

The foam gives in under your clawing fingers, feeling yourself near your climax. You’re close to a scream - until he finally loosens his grip around your sensitive bundle of nerves. You’re relieved and frustrated at the same time. Your clit’s now swollen and overstimulated and oh so close to pop you off the edge.

“P-please…” you whimper and turn your head to the side against the mat to be able to look back at him, “De… please – I-… I’m so close-”

“You want to come on my face… or my fingers, hm?” Dean hums with a cocky sound to it.

“Both- anything- please,” you beg now, your chest heaving under the weight of your body, your breaths grown ragged and heavy.

“Such a greedy little thing,” he growls, his tone laced with pride, knowing exactly that he can always drive you mad with need if he wants to.

He shifts his weight, his chest resting between your legs and his free hand snaking over your thigh to join him. His fingertips reach between your legs, running through the folds, as he lets his finger circle around your entrance for a moment. At your muffled whimper, he effortlessly pushes his middle finger inside. “But first, I wanna see if I can make those legs of yours quiver from just one finger…” Dean states, his tone low with a raspier edge, and darkened eyes fixed on your dripping hole.

You gasp at his words, his gravel tone sending a shiver down your spine. But after a moment of enduring his finger’s tantalizing strokes, your patience snaps and you regain your voice.

“Oh fuck you.” you groan in protest, your teeth clenched from frustration. One finger after all this teasing? This was just pure torture now and he knew it.

“What? You want me to go in full house?” He chuckles knowingly, enjoying your worn down patience way too much for your liking, “Want me knuckles deep inside you again, is that it?”

He doesn’t wait for an answer, but instead quickly jams his index finger inside you, pumping them both in and out while his lips enclose around your clit once more.

You don’t even have the time to gasp for air when you feel your walls clenching and gripping onto his curling fingers. A few seconds of intense onslaught of his is enough to send you flying over the edge with a loud guttural moan. Your nails dig into the mat, your legs are shaking and your walls fluttering around his fingers while he helps you ride out your height.

Once you fall limp and try to catch your breath, Dean slowly withdraws his two fingers to raise them to his mouth and suck them clean. He grins, wiping his face with the back of his hand before his tongue swipes over his lips, kingly as he does so, savouring every last drop of your taste.

He shifts on top of you to move a hand next to your waist on each side, leaning down to grab the hooks of your sports bra between his teeth. With a swift tug, it falls open and he leans in to kiss you between your shoulder blades. You let out a low hum, enjoying the soft affection with eyes fluttered close. He moves again to gently tug the last piece of clothing over your shoulders and arms until he flings it over his shoulder, where it lands next to your other things.

You feel the rough fabric of his shirt graze your skin, and the buckle of his belt makes you shiver when it lowers down on the nape of your back. Just below it, the growing bulge behind his jeans rubs against your butt when he rolls his hips against you.

“You feel how hard I am just because of you?” He murmurs against your skin, the words almost lost in a stifled groan. But you still answer with a low confirming hum. He continues to plant kisses along your back, taking his time to explore every single inch. His lips send small shivers down your spine and all the way to your core again, each one of them like a spark along your fuse.

“Babe?” He mutters between hot kisses lining up to your ear now.

“Mh?” You hum into the yoga mat while tilting your head slightly for him.

“You ever heard of the elephant position?” He asks innocently.

The what? That name earns him a surprised giggle of yours. It was nothing unusual that Dean would randomly hit you up with some sex-position he’d like to try out with you, but this one was a new one to you. “Are you seriously talking about how elephants mate? Or are you trying to impress me with the yoga pose?” You tease him. Clearly he wasn’t talking about the latter. “Or, let me guess, it’s a Kama Sutra thing.”

He plants another open-mouthed kiss right under your ear, “Mmm-hm,” and his throat rumbles against your neck, is lips lingering there for a moment while he murmurs, “That… Ever tried it?”

With the side of his face he nudges your head further aside before he dives down to take the skin of your neck gently between his teeth, pinching it enough to make you gasp.

At his question, though, you look a bit sheepish and you shake your head, “No… is it… good?”

Dean beams at your admission – he simply loves it whenever he can show you something new, especially when he knows how much pleasure it��ll bring you.

He perks his head up like an excited dog, “Oh you’ll love it, baby. I promise. It hits all your super-sensitive spots.” He leans back in to nibble on the soft flesh of your neck before he continues in an eager tone. “You wanna try it?”

“Uh,” you lift your head now to glance back, meeting his glinting green eyes above his wide smile. Your lips curl upwards at the sight of his excitement and you respond, “Yeah, will you, uh, will you show me?”

“Of course, baby.” He leans back to lower his hips on your thighs again, his eyes raking up and down your buck naked body. “I need you to stay just like this- uh – whatever pose this is.”

You chuckle and raise yourself on your elbows. “The sphinx.”

“Yeah, right, okay, sphinx.” He mutters and pushes himself off you for a second, “Stay. Don’t move.”

He reaches for his belt buckle, the sound of the metal clinking while he unbuttons his jeans and slides the denim along his boxers off his hips. The heavy, worn jeans quickly land somewhere next to your yoga outfit, and his shirt follows seconds after.

“Yeah, that’s better.” He mutters to himself before climbing on top of you again, his knees straddling your legs as he lowers himself down. He runs his hands up and down your sides, his firm pecs brushing against your back. “’M not crushing you, am I?” He asks, his tone softer for a moment.

“No, all good. Don’t worry.” You reassure him before you angle your shoulders to nuzzle your nose against his jawline, feeling the scruff prickle your skin.

“Good.” He nuzzles back into your neck, hands trailing down your arms, “Mmmh… you’re so soft, sunshine.” His hands continue their path until they wrap around your wrists and guide your arms up just slightly above your head as your chest slowly lowers back down. He places them there before he murmurs against your ear, “Keep them there for me, baby, keep them right where I can reach them, yeah?”

“Mhm.” You nod and suddenly become aware of the way the tip of his erection brushes against your inner thighs every time he moves.

“Just wanna make sure I know where those hands are.” Dean chuckles and purposely bucks his hips so that his swollen head briefly kisses your entrance.

His hands slowly glide up the inside of your arm, fingertips ghosting over your twitching skin. He brushes them underneath you, hands up the front of your chest, cupping your breasts and slowly kneading the soft flesh in his palms, “Can’t have you squirming and fighting against me while I’m trying to make you feel good, y’know.”

You arch into his hands, needy little sounds of pleasure dripping off your lips. Your core’s burning again, begging to be taken care of.

“I know baby, I know…” he coos between tender kisses, and in spite of his chapped lips, he caresses your shivering skin with soft love letters.

“Dean- please- I-” you start to plead, your voice bouncing off the pink foam you’re panting against.

But Dean finishes for you with his voice dropped to a rougher octave, while still trying to sound soothing for you, “You just want me to pound you mindless into that damn mat… I know… and I can’t wait to make you cry, sunshine… Gonna make you scream my name so loud, the folks at the front desk will hear it and think there’s a whole exorcism going on or somethin’… But first you need a lil’ patience, sweetheart… alright?”

The question was of course rhetorical. Once your boyfriend has his mind set on something, he’ll pull through with it. Or at least that’s how he’d like to describe himself. You of course know that you’ve got him wrapped around your little finger whenever you really want.

“It’ll be worth it, I promise… I’ll make sure you come so hard, you’ll be seeing nuthin’ but stars for a whole minute.” He adds while he withdraws one hand to palm his erection before he lines up behind you.

“But first… I gotta pump your tight bands of muscles up… the ones closest to your sweet, drippin’ entrance– ” He begins to explain but gets interrupted when he pulls a gasp from your lips, thanks to him suddenly biting down on your shoulder.

His words come out slightly muffled as he continues with a growl, “… get them hot ‘n aroused ‘n sore from all my undivided attention… I want you to come just from my cock inside you.”

You feel his tip tease your entrance, circling it but never pushing in like he’s waiting for the right moment. His feet then dip beneath your legs, before his calves and heels press against your thighs to keep them clamped together. “That’s it… keep ‘em nice ‘n tight.” He husks somewhere behind you while he rocks his hips again. His warm breath’s skimming over your sweat-dampened skin sending shivers of goosebumps in its wake.

Once you’re just in perfect position for him, he finally pushes his cock inside you in one smooth motion which draws a low guttural moan out of your throat.

For the next minutes, Dean does as he explained, taking his sweet time to build up your tension at just the right spots.

He pulls the ridged-band along your slick, clenching walls, slow and ordaining. When he feels you twitch, he knows he’s found just the right spot. With deliberate rolling motions of his hips he begins to push and pull the head of his cock along your g-spot.

Your face drops to the mat, a shaky breath rippling out of your throat when you feel him graze your insides. His slow motions are torturous and unbelievably pleasurable at the same time.

His strong thighs bind yours between his own while he increases the friction, now rutting his swollen tip against your tightly grasping entrance.

“You feel that baby?” He whispers huskily, his lips right next to your ear-shell.

“Y-yeah,” you answer weakly, your breath slowly picking up pace to match his hips new rhythm.

Once he notices your entrance shimmy around his shaft, he knows he’s got you just where he wants you. He swiftly pulls his length out, earning himself a frustrated whimper of yours.

“No- no please, don’t stop-” You start to plead but before you know it, he pushes back in. This time without holding any inch back.

“You did so well, being so patient for me…” He begins to mutter against your hair, “I’ll take care of you now. Let go and just feel me, sunshine.”

You groan, arch your back and raise your chest off the floor, holding yourself upright with your elbows. But you quickly notice it’s in fact, Dean, who’s keeping you from collapsing back into your pink mat.

He had his arm wrapped around your torso, pulling your back close to his chest. His large palm slides along your body until it wraps around your soft, plump flesh to cup one of your breasts, your nipple teasingly pinched between his thumb and index finger. He supports you both on his free hand pressed into the foam, the muscles of his biceps flexing relentlessly from the force of his movements.

All the while he keeps snapping his hips against your bum with precise thrusts, each time taking your breath as he meets your cervix. Each collision eliciting a twinge, like a sweet hurt that has your pupils dive under your eyelids.

He switches his supporting arm, the freed hand roaming every part of your body like he’s exploring and worshipping it at the same time. His large palm comes to rest on your ass, splayed out on your soft flesh. Then you feel him slip out of you, shifting his position as he puts some of his weight on your ass now to hold you down when he begins to pound you into the mat again.

“Oh fuck-” The new angle draws a surprised yelp from you.

But Dean quickly comes to soothe you with open mouthed kisses dancing up your spine, his teeth skimming your skin and his lips tasting the sheen of sweat clinging to your body. Arrived at the nape of your neck, he husks out, “Good girl, takin’ every inch of me… lettin’ me fill ya up all the way…” his voice drifts off when his tongue darts out to lick the sensitive spot behind your ears, sending another shiver down your back.

The new pace of his hips is slower but no less intense. He continues to slam his cock past your slick folds, pulling out almost entirely before he rocks his hipbones back into your cheeks. Over and over, each time all the way to the shaft’s base, drawing those guttural moans from your sweet lips which make him growl with pride.

He rasps out groans and praises against your neck, each spurring you on equally, “You’re taking me so well, baby- Fuck- so good for me… my good girl… bein’ so, so perfect, only for me…”

Your moans grow more desperate, breathless, feeling his cock harden against your soft walls. “D-Dean-,” you whimper as your head briefly lolls back to lean into his shoulder just before it drops forward again with a loud shuddering moan sparked by your core.

Your hands start fisting into the crappy motel rug, pulling at the loose threads of it as you desperately search for something to hold onto. Your frantic actions don’t go unnoticed by Dean who’s watching your every hitch in breath and twitch of your muscles, always making sure he doesn’t miss the signs that the pain’s still pleasurable to you.

He quickly shifts his weight as his hand on your ass darts over to your clawing fingers, doing the same with his other. He untangles your fingers from the fabrics, intertwining them with his own while his forearms come to join yours on the pink foam, supporting himself on both elbows now.

He can feel your legs tremble against the weight of his hips, which he uses to plough you into the yoga mat as he slams into you. His movements now erratic and rough. Squelching sounds mix with your combined moaning and panting. Driving each other closer to the edge with every sound.

“Y-you close, baby?” He growls against your ear, already knowing the answer. He can feel your fluttering walls gripping him tightly, “Fuck-” he groans, his hands squeezing yours and pinning them there when your body starts to buckle and shudder beneath him. He’s now driving his cock inside you with primal need.

“Oh God-” you whine, face pressed flush into the foam as you feel the knot in your belly tighten up and your muscles go tense.

“F-fuck yeah- that’s it- squeeze and come on my cock, come for me-” He growls, his voice dropped to a gravelly, rumbling tone. He runs his nose along your neck, across the trail of red marks, when he suddenly sinks his teeth into your flesh once more.

And that does it for you. Your knot explodes into waves of pleasure rippling through your body. Stars take over your vision when you scream his name. Your walls flutter around his cock, pulling him over the edge along you and coating your walls with his warm seeds. The climax keeps crashing down on you in multiple shock waves until your body finally falls limp, your limbs twitching as if you’d been struck by a lightning bolt.

Dean collapses on top of you, his breath ragged and hot as it wafts against your sweaty skin. His forehead dropped to your shoulder, his biceps just barely able to keep his body from completely burying you under his weight.

“Damn… that- wow…” You whisper breathlessly, still trying to regain your vision and collect your thoughts.

“You were amazing, baby.” Dean praises you with a hoarse voice, his lips lingering on your temple.

You tilt your head to catch his lips in a soft, but purposeful kiss. When you pull back just enough to speak, you catch a glimpse of his eyes briefly widen at your words, “No, you are amazing.”

♡

For a moment you both enjoy each other’s soft breaths and the way he hugs you tightly as he wraps his body around you like a heavy blanket. You keep nuzzling your faces into each others hair while you let the silence be filled by your affections. Silence except for the TV which’s now playing the final scenes of “Die Hard” in the background.

After some time, Dean pushes himself off you, gently sitting back down on your bum as he takes in the sight of you in front of him. His hands are kneading the flesh of your ass as he watches you with hooded eyes. Then a cheeky grin begins to form on his lips when he realizes something.

“Y’know, you’re laying down in the perfect position for me to do somethin’.” He states with a full-out grin now.

“Huh-?” Before you can even process what’s happening, his fingers dig into the skin where he knows you’re the most ticklish.

“Dean!!” You squeal like a mouse – but the sound quickly hitches into a high-pitched giggle while you desperately try to wiggle away from him. “St-stop it- y-you jerk!” You stutter between gasps for air and the tears gathering on the rim of your eyes. You kick your legs, throwing him off and not wasting your chance, slipping away to scramble for an escape.

But you quickly find yourself back on the motel rug with a gasp and a thud, thanks to Dean pulling you back by the ankle. His smile has turned into that smug grin of his when he taunts you in a commanding voice, “Where d’you think you’re goin’, hm?”

“Th-that’s- unfair!!” you protest, but your words dissipate in another round of giggles as you turn onto your side, trying to free yourself. But Dean has his calves wrapped around your knee to lock it while his fingers skitter across the heel of your foot. You grapple with his free hand but he effortlessly evades your flailing limbs and grips you by the hip before you get to wiggle away again.

Next moment, you find yourself unceremoniously flipped back onto your stomach and his weight dropped down on your ass to pin you down bellow him. His thighs straddle you, this time reverse as his hands dart out to snatch one of your ankles, bending your leg back so he can continue his assault.

“Unfair? Me?” He lets out a deep chuckle, lips pursed in mock-innocence, his head tilted to glance back down at you over his shoulder. He stills his teasing fingers, waiting for your reaction.

You try to catch your breath while you narrow your watering eyes at him, daring him to go on.

Of course that sly bastard musters the audacity to answer your threat with a wink of his emerald eyes glinting with mischief and his lips flashed into that cocky smirk of his.

“Never.”

A/N: Dean going from goofy to smut to fluff to rough sex and back to fluffy and goofy like 📈 Idk I just see him like this, a caring 'n goofy softdom horn dog who loves it when he can show you new things.

Let me know what you think and if you got to enjoy it my sweet vixens ♡

Masterlist of opened windows:

1st Dec. - Sunshine 2nd Dec. - Spell Book 3rd Dec. - Lights Out 4th Dec. - Tickle 5th Dec. - Dirty UNO 6th Dec. - (TBA) 7th Dec. - Candlelight 8th Dec. - Hex Play 9th Dec. - Whip Stroke 10th Dec. - Barbie World 11th Dec. - Temptation ... (check the masterlist for more!)

Kinky Advent Calendar Tags:

@ariasong11 ♡ @deansjacket ♡ @literallylexa ♡ @lmpala1967 ♡ @foxyjwls007 ♡ @impala67rollingthroughtown ♡ @aylacavebear ♡ @jc-winchester

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