#hooker!Dean | Explore Tumblr posts and blogs

whimsyfinny · 9 months ago

Text

Sexy F*cking Nerd

Dean Winchester x F!Reader

Summary: When Dean discovers a little secret of (Y/n)'s during a case research session he can't help but let temptation get the best of him.

Warnings: Language, Smut, Fingering, PinV, Oral (M receiving), slight angst if you squint, Dean having a glasses kink (not really a warning but not everyone wears them hahaha lucky bastards)

MDNI! 18+

Word Count: 5688

A/N: It's taken a little while but here is the second competition winner from a few weeks back, the prompt provided by the wonderful @foxyjwls007 - I hope you like it!

The motel room was stuffy to say the least - that usual aroma of stale cigarettes and cheap air freshener lingering around us. There was a dripping sound coming from God knows where and the AC hummed in between the concerning clinking from deep within the vents. It was crap. So crap. But it was home for a few nights; just like all the motel rooms that came before. Dean stepped past me and over the threshold, immediately slinging his duffle and jacket onto his chosen bed. He stretched his arms above his head, the grey Henley clutching his muscular abdomen and rising enough to flaunt what lay beneath. I sighed, following him in and slumping onto the bed beside his - the musty stench from the sheets enveloping me.

“Well…” Dean started, pulling Sam's laptop out of his bag and placing it on the small table by the window.

“Well…?” My voice echoed as I focused on the ceiling fan that spun off centre.

“...This is… nice?” His statement was more of a question as he looked around with raised eyebrows. I propped myself up on my elbows, flashing him a look of speculation.

“Seriously?” A moment passed before he huffed a long-held breath and slapped his large palms on his thighs.

“No of course not, this place sucks more dick than a hooker on payday.”

“You got that right,” I flopped back down onto the bed, a small dust cloud erupting under my weight. I closed my eyes and listened as Dean pulled a chair out from under the table, slumping down into it. Then there was the familiar click of the laptop opening followed by the sound of stuttered not-quite-touch-typing, presumably he was starting work on the case that we’d come here to investigate. The tap tap tap of whatever was leaking began to drill into my brain, my patience already wearing thin with the rooms dire ambiance. I pulled myself up to sitting, criss-crossing my legs on the bed and brushing whatever that dust from the bedding was off my sweater sleeves.

“When's Sam back?” I asked, watching as Dean searched the keyboard in front of him for some long lost letter.

“Uuuh, I'm not sure. He said to work this case without him.”

“Ugghhh, I bet he's having way more fun than us right now, it's not fair,” I plopped my chin into my palm and stared past the older Winchester out the window, almost willing Sam to appear and walk in like any other day.

“It's just some dumb wedding, I doubt he's having that much fun.”

I scoffed before I could stop myself, Dean breaking eye contact with the screen to throw me a raised eyebrow.

“Look,” I collected myself, “you didn't know Sam in college. He won't admit it but he was popular. Really popular. Not the total nerd you think he is. He's absolutely having fun with these people.”

“Yeah right. So who's at this wedding anyway? Why was it so important that he just had to be there?”

I rolled my eyes, knowing full well Sam had already told him all the details. Typical Dean.

“It's for a couple of friends who he and Jess were close with back then. Pretty sure the bride was prom queen in highschool or something and the groom was a trust fund jock. Either way, not my crowd,” I sighed slightly, memories from my college days flooding my mind.

Deans eyebrows twitched into a small frown, his thoughts seeming to cloud his vision for a second before he reluctantly dismissed them. I looked down into my lap for a moment, reminiscing how I always kept my distance from Sam whilst at Stanford, but he had always been that boy that would make my heart flutter when he spoke up in class or when I'd see him on the quad with his friends. I remember seeing him with his nose in a book once at my usual desk in the library, my cheeks burning when he caught me staring. Who would've thought several years down the line I'd be sat in a bottom-rung motel room with his obscenely good looking older brother researching monster lore. At least we would be researching monster lore, if it wasn't for the small growl my empty stomach had gurgled out. I couldn't stop the small pulse of embarrassment burning into my cheeks as Dean eyed me with a grin.

“Wanna get some lunch?” He asked, standing up like he already knew my answer.

“Fuck yes. I'm feeling burgers,” I shuffled to the edge of the bed and stood up, watching as Dean shrugged on his leather jacket and headed to the door, holding it open for me.

“Now you're speaking my language.”

The diner was almost as sad and withered as the motel room, however the food was nothing short of spectacular. I watched in awe as Dean polished off his second burger, a small glob of sauce sticking to his stubble and threatening to drip off his chin. He must've felt me watching in wonder - or perhaps disgust - as when he looked up from his plate he shot me a questioning glance.

“What?” His tone was a little defensive through the mouthful of fries he'd just shovelled in. I took a second before asking, half-genuine:

“Where do you put all of that?”

“Put what?”

“The food - where does it go? Do you have hollow legs? Two stomachs? Does it just evaporate as soon as you swallow it?”

He grinned, wiping the sauce from his face with a napkin.

“Goes straight to the abs baby. It's muscle fuel,” he leant back in his chair, stretching a little before patting his stomach to punctuate his statement. I simply rolled my eyes.

“Yeah right, you're not that muscly Dean.”

“How would you know? You've never seen me with my shirt off.”

“I know, and I plan to keep it that way.”

He feigned a pout before returning to his fries. We ate in a comfortable silence for a few minutes, my mind absently going back to all the lore we should be trying to gather. I gripped my milkshake that had so generously been served in a thin paper cup, attempting to suck the practically solid beverage up the equally thin paper straw. Finding the nearest library would be the next task on our to-do list, despite the protesting I know I'll get from Dean.

“Hey, (Y/n)?” My train of thought was derailed at the sound of my name. The slurping of over-thickened milkshake from myself ceased.

“What's up?”

“What were you like in college?”

I eyed him with caution, wondering what part of his brain was in control right now.

“What do you wanna know?”

Catching the wariness to divulge him to such information, he smiled slightly, shrugging his shoulders.

“I'm not asking to be weird, I just-” he paused, choosing his next words tactfully, “the way you described Sam as being a totally different person - some hot-shot with the perfect grades, popular friends and a girlfriend like Jess - it just got me thinking. How would Sam have described you?”

I almost spat my dairy-goop back into the straw, my brain freezing.

“Dean,” I started before planning what I was going to say, placing my cup on the table. “Sam wouldn't be able to describe me.”

My words brought a small smirk to his lips.

“You were that hot, huh?”

“What the fuck- no- I wasn't- he didn't- Sam never- ” I stopped myself before I had an aneurysm and took a deep breath.

“I was in a totally different crowd to Sam. He was always surrounded by people and, well, I barely even had a crowd.”

“Lone wolf?”

“Bingo. But definitely not the cool, collected, stoic type. Think more, invisible to the public eye, always carrying books, and borderline selective mute because of how shy I was.”

“Oh… what changed?,” Deans tone changed entirely, genuine intrigue seeming to take the wheel. I couldn't help but laugh slightly, remembering my method to forcing myself out of my bubble.

“The only job I could get was in a bar. No one else wanted the hours and I desperately needed cash. I didn't really have a choice after that,” I paused, remembering how terrified I was on my first day and grinned slightly, grateful for the extra confidence I had now because I took that leap.

“Hey, what sort of crowd do you think I would've been in?”

I snorted, looking up into his expectant eyes - almost captivated by the glistening greens.

“What am I? A BuzzFeed quiz? I have no idea Dean, you're too much of a wildcard to predict. You probably would've fit in with anyone and everyone.”

“Even you?”

For reasons unbeknownst to even myself, my breath caught in my throat. The sudden soft sincerity of his voice contradicting his usual temperament, my heart starting to flutter in my chest. If the college version of myself had met Dean back then I just know I would have been enthralled at first glance.

“I don't think you would've noticed me. You would've been surrounded by every tall, thin blonde and brunette with perfect tits. Trust me, you would've been distracted,” I smiled an almost sad smile at the thought of him simply being on university grounds and having the time of his life - knowing it was something that he was never going to get the chance to experience in this upside down life of his. Of ours. He tapped his fingers on the table for a second, likely lost in some ludicrous thought I don't think I'd want to be privy to. I attempted another slurp of my milkshake when the paper straw gave out and flopped in half, the need to leave conversation and the diner suddenly looming over me.

“Come on, let's get to the library before it closes,” I stood and pulled my oversized sweater down so it covered my ass before reaching for my backpack. Just as my fingers touched the worn fabric of the strap it was torn away, my head snapping up to Dean who flung it over one shoulder with his signature grin on his face.

“Lead the way nerd.”

I couldn't help but beam at his playfulness. I hated the fact that he made it so easy to adore him. Hated that he completely overlooked how I was his total opposite in almost every way. How when we were talking, his eyes never left mine - how he was genuinely interested in what I was like in the past. And how, when I had his attention, he didn't even notice that the hot waitress had written her number on a napkin and left it next to him.

The trip to the library was about as eventful as it sounded. After checking out multiple books on cursed items, local lore and popular antiques from the seventies, we loaded ourselves back into the impala, made an all-important beer run before heading back to the motel.

The small table by the window was now totally smothered by a blanket of books, maps and empty beer bottles. Deans chin rested in his palms as he stared blankly at the screen in front of him, and I must've read the last sentence of the paragraph laid before me a dozen times without it even sinking in. The obnoxious dripping and humming of ancient appliances was starting to make me feel restless.

“It has to be the boots,” Dean groaned, draining the last of his beer.

“Either the boots or the disco ball. But my money is on boots as well,” I sighed, pushing the book away from me and standing slowly, gathering the quickly accumulating litter now scattered around us.

“I'm gonna make some coffee, my brain is fried over how fucking ridiculous this case is,” I ditched the trash in the bin before filling the coffee machine, listening to it whir to life whilst I headed to my bed. I could feel Deans gaze on my back as I rummaged around my bag in search of a specific item.

“What are you looking fo-” he'd started to ask the question but his voice died in his throat when I turned around. I quickly pushed my newly adorned glasses up the bridge of my nose, already feeling the oversized frame start to slip down as I tried not to make a big deal over them.

“What?” My tone was a fraction off aggressive when I realised he was staring. He seemed to snap out of his daze, quickly rubbing the back of his neck and turning back to the laptop screen. He cleared his throat

“I uh, I didn't know you wore glasses,” I could tell from the slight tremble in his voice that his mind was reeling.

“Is there a problem with that?”

“No! I mean, no, absolutely not. They look good. The glasses, I mean. The glasses look good. Not on their own, obviously. On your face. They look good on your face. You have a great fa-”

“Dean?”

“Yeah?”

“Shut up.”

“Sorry.”

I grabbed a mug from the cupboard and set it on the counter, filling it to the brim with caffeinated goodness. I couldn't stop the grin spreading across my lips at Deans fumbling, almost finding the whole ordeal a little charming. I sat back down at the table and pulled the books back towards me, also grabbing my pen and tattered notebook.

“The guests at the club mentioned hearing footsteps - so it has to be the boots, right? A disco ball wouldn't make that sound…” my voice trailed off when I realised that, even though Dean was looking at me, he wasn't listening to a word I was saying.

“Earth to Dean?”

He flinched slightly at his name, but felt no shame delving in with a completely off-topic question.

“So how long have you worn glasses?”

“I’ve always worn them,” I slid back into my chair at the table opposite him, not sure whether to laugh at the shocked expression on his face or whether to be concerned about his observation skills.

“What?! No way, I would’ve noticed,” He opened another beer and took a sip before tracing the opening to the bottle over his bottom lip.

“ I only wear them for concentration work, and I have emergency contact lenses if I know I’m going to be around a lot of people as I don’t particularly like how they look.”

Dean made a small disagreeable expression before averting his gaze from mine back to the laptop, taking another swig of his beer. I placed my coffee mug down and settled back into the book I was reading before, and after a few moments I could feel my skin begin to prickle - as though I could feel a pair of eyes on me. I glanced up, my breath immediately catching in my throat. Deans eyes found mine, burning with an intensity that made my heart hammer in my chest. I didn’t want to look away, but under his gaze I felt like I’d been stripped bare, unable to hide my insecurities from an eye that seemed to scorch through to my very core.

“Dean-”

“(Y/n), you should really have more confidence in yourself; I think the glasses look cute as fuck. You should wear them more,” a fierce blush erupted across my face when he spoke, his assured tone leaving no room for disagreement. I tried desperately not to let on that his words held any sort of impact over my decisions so I looked down, away from his scrutiny and simply said:

“Maybe I will.”

He hummed in approval, finally looking elsewhere and I couldn’t stop myself from breathing a sigh of relief when the pressure of his stare was averted.

The evening dragged on and an hour and a half had passed since his loaded comment. I was on the third book we’d checked out of the library, now trying desperately to find the curse that would cause a pair of 1970s glam rock boots to dance for eternity and haunt anyone who tried to wear them. This case was absurd, and I could feel myself growing restless with the small amount of progress we’d made. I huffed out a sigh and leant back in my chair, the faux leather and rusted metal creaking under my weight. Pulling the hair bobble from around my wrist I scooped my hair into a bundle on the top of my head, securing it in place; the sensation of air on my neck seemed to clear some of the fog from my brain. The messy bun was comfortably enough that I could forget it was there, and I allowed myself a stretch before leaning back over the table, grasping my pen. As I began to read the next segment, I absently traced the end of the pen over my bottom lip, running it back and forth a few times before gently nibbling on the end. I heard the shuffling of Dean moving in his seat and a ragged clearing of his throat before the sound of vigorous laptop keys clicking ensued. Without looking up at him I continued reading, the pen still tapping my bottom lip, and when I neared the bottom of the paragraph, I slowly licked the pad of my index finger. My eyes never leaving the words, I turned the page swiftly with my dampened digit, the transition from one page to the next perfectly seamless. Another shuffle from the man opposite followed by a quiet groan filled the silence between us. Pen still between my teeth, I lifted only my eyes to glance at him and noted the dusting of pink across his cheeks and the furrow in his brow. Concluding that he’d had one too many beers I decided to ignore his persistent fidgeting, returning to my previous task on monotonous reading. Several sentences in and I’d almost forgotten Deans restlessness - that was until I pulled my bottom lip between my teeth, deep in thought, that I earned myself a throaty groan and an exasperated sigh. I looked up just in time to watch him wipe a large hand down his face, momentarily masking his pained expression.

“Can you not do that? I can’t concentrate when you do that.”

“Do what?” Upon asking my question I absently took the pen between my teeth again, quickly glancing down at the book to place a mental bookmark.

“That.”

“What?”

“That. That thing you do with our mouth, and the pen, and your tongue and your finger. Can you please stop before it kills me.”

The heat beneath my skin was immediate at his admission, knowing my small, absent-minded actions were playing on his mind and making it hard for him to think straight. I instinctively crossed my legs, a fluttering in my lower belly instantly dragging my mind back to the deprived things I’d imagined Dean doing to me in the depths of night. The places I’d imagined his hands travelling, the areas his lips would touch and the sensations his tongue could create. These were deeply, deeply personal fantasies, and right now as Dean looked at me with a restrained hunger, I felt like I was wearing these fantasies for the world to see. For Dean to see.

“It doesn’t help that you’ve been sat over there like a sexy fucking librarian all evening, but every time you do that anything with that mouth - shit, sweetheart you’re driving me insane.” His voice was gravelly as he looked at me with desperate eyes across the table. The overly rational part of my brain had shut down completely, and now the part of my mind that had spent hours conjuring vivid scenes of Dean Winchester ravishing me in my entirety had taken the charge. I stood slowly, taking a moment to reason with myself - unsuccessfully of course - before sinking to my knees in front of my chair. I could see Deans strong thighs were spread wide beneath the table so I crawled forwards, across the cold tiles and placed myself between his legs. Resting my palms softly on his thighs I made him flinch at the unexpected contact. He immediately scooted his chair back, allowing a gap for me to poke my head through - his hand instantly acting as a barrier between the edge of the table and my skull. I got comfortable and allowed myself a moment to gaze up at him, to take in the strained furrow in his brow and the parting of his lips. I observed the way his chest rose and fell in apprehensive breaths, and the way his free hand clenched into a fist on his thigh - like he was so desperate yet so scared to touch me.

“(Y/n)-”

“Dean,” I spoke softly, slowly running my hands up his thighs - delicate palms against rough denim, “you’re a smart boy - you know I wouldn’t do something I didn’t want to do. So please, don’t say I don’t have to do this.”

Dean released a shaky breath the moment my fingers unclasped his jeans. I tugged them down slightly with his help, just enough so I could dip my hand into his boxers and wrap my fingers around his half-hard length. The moment my skin touched his, his head lolled back and his eyes fluttered closed with a breathy moan on his lips.

“Fuck…”

I gently pulled him from his confines, coming face to face with the cock I’d literally dreamt of again and again. I took the scene in, committing to memory the sharp outline of his jaw and the way his long lashes rested on his lightly-freckled cheeks. The way that, every time he breathed in, I could see his defined muscle tone through the thin fabric of his shirt; and with every small caress that my fingers made against his length, it made his fingers twitch and teeth clench. I licked my lips before leaning in and took his tip into my mouth, not giving him a chance to finish sucking in air through his teeth before I plunged his entire length down my throat.

“Oh FUCK.”

His hands flew to my hair, fingers gripping tight as they loosened strands from the messy bun, causing them to fall around my face. He’d lifted his head to look down at me, pupils blown as he pulled his bottom lip between his teeth. He looked nothing more than enthralled. Infatuated. Entranced. I moved my head up and down, up and down, again and again to a steady rhythm, pressing my tongue to the underside of his now rock-hard cock to trace every vein and nerve-ending.

“Shit, (Y/n), I didn’t know you could suck cock, like, at all… how’re you s’fuckin’ good…” his voice was breathless as he continued to grip my hair, his head flopping to the side as pleasure started to overcome his senses. I released him with a small ‘pop’, wrapping my fingers around him and smearing the warm mixture of saliva and precum from tip to base.

“Despite everything I told you earlier, Dean, I’m not a virgin - and this certainly isn’t my first rodeo,” my voice came out more sultry than I’d expected and I could feel Dean tremble beneath my palms.

“Fuck, I wish I’d known that sooner,” I chewed on my bottom lip, quickly becoming addicted to the way he writhed at my touch. The way he moaned and gripped my hair tighter when I sucked him back into my mouth was like pure ecstasy, my insides heating up and throbbing with an ache of familiar arousal. Like a thirst that could only be satisfied by him. By tasting him, feeling him on my tongue and drinking in every sound that passed his plush parted lips. The sensation of my glasses slipping down my nose as I sped up my ministrations had me reaching to push them back up, but not before Dean beat me to it. With the rough pad of his thumb he pushed on the plastic bridge, his palm and fingers pressed to my flushed cheek in the most tender, almost heart wrenching caress. I thought my heart might stop when he tilted my face up to his; lustful eyes burning into mine with a vehemence I’d never encountered. I stopped in my tracks, all actions ceased as the spell he’d somehow put me under wouldn’t let me look away.

“If you keep going like that darlin’ this whole thing is gonna be over before you know it,” his voice was raspy, a rawness to it from the harsh breaths and ragged moans that had been pulled from his throat. He slowly pulled his cock from my spit-slick lips and grasped it loosely, giving himself a few lazy pumps whilst his other hand never left my face. He stared down at me, taking a few moments as though he was committing the sight of me, knelt between his knees with flushed cheeks and swollen lips to memory. Once it seemed that memory was locked away in the depths of his mind, he grasped me by the arm and pulled me effortlessly into his lap, his fingers almost bruising against my skin. Immediately I felt him, in his entirety, press against me with the heat and wetness seeping through my jeans and past my panties. This time when our eyes met, there was a mutual desperation; a need to consume each other and to feel every inch of his heated skin against mine. He pulled me frantically down to him and crashed his lips against mine.

Some people describe their first kiss with someone like butterflies in their stomach, or fireworks exploding all around them. That wasn’t at all what this was like. Kissing Dean Winchester was different - it was wild and untamed - and describing this experience in such a mundane way would be like adding water to a top-shelf whiskey. Kissing Dean Winchester was like driving the impala at one thirty with the roar of the engine drowning out the rest of the world. It was like trying to ride a wild mustang without a saddle, or daring to stand on the highest peak on Earth with nothing to tie you down. It was exhilarating in the most dangerous way imaginable - and I was now officially a thrill seeker.

The warm taste of the beer on his tongue and the masculine scent of old leather and cologne was pulling me under. Breathing no longer mattered as long as his mouth was on mine and his fingers were in my hair, now tugging the bobble out and throwing it to the floor. As my hair tumbled free he grabbed under my thighs and stood effortlessly, moving me from his lap to the edge of the table without his lips leaving mine. I winced slightly as the corners and several books and the laptop jabbed into my rear and I fumbled to move everything aside, failing when I refused to unlock our lips. Deans patience was non-existent and with one sweep of his strong arm everything tumbled to the floor - including the laptop. I threw the remaining books from underneath me down to join them, no longer caring for their wellbeing. Before I could pull Dean back in - to allow him to do whatever the fuck he wanted to do to me - he hastily pulled off my boots and tugged down my jeans, throwing every item to the growing pile of chaos beside us. I discarded my sweater and top, but before I let his fingers touch my bra I wanted nothing more than to return the favour.

“I guess you can forget about that whole ��never seeing me shirtless’ thing, huh?” he smirked through the sexual fog, not waiting for a reply as his lips hungrily found mine again, his own top falling to the floor.

“Shut up Winchester. Now are you gonna fuck me or wh- OH FUCK-”

Two thick fingers crept under my panties and plunged into me with zero hesitation, curling up and stroking the sensual cushion deep within my core with skillful precision.

“Oh yeah? You want me to fuck you?” Even with my face now buried in the crook of his neck, I could hear the smirk in his voice, the tormenting tone going straight to my brain.

“Y-yes- fuck- please,” my knees twitched either side of him, squeezing at his hips with every push of his fingers. I gripped his shoulders tight, nails indenting his skin as I leant back to look at him better. Seeing the beads of sweat on his chest and brow alongside the raw, carnal desire in his eyes could have undone me there and then. He frowned in disapproval when I moved to remove my glasses, the fingers that were just inside me now wrapped forcefully around my wrist.

“What d’ya think you’re doing?” straight away I knew his growling question left no room for negotiation.

“I was just-”

“The glasses stay on.”

“To the end?”

“‘Til I say you can take them off.”

I did as I was told, moving my hand to grip the soft strands on the back of his neck, softly dragging my nails over his scalp and drawing a shiver from his spine and a groan from his lungs. He pulled me against him, crushing his lips against mine one more time. He swiftly pulled away and I leant back on my hands, both of us taking a moment to drink each other in - to bask in lascivious glory. I pulled my bottom lip between my teeth and looked up at him through my lashes, the lenses of my glasses starting to fog around the edges. Another deep moan rumbled from his chest as his heated gaze stayed locked to mine.

“I can’t wait any longer now that you’ve looked at me like that. Fuck.”

With a large hand gripping the soft flesh of my thigh he pulled my underwear to one side and lined himself up, slowly sinking in. Blissful moans harmonised between us, the rawness of him stretching me was unlike anything I’d ever experienced and my quivering thighs wrapped around him, pushing him to the hilt. He secured his large hands on the soft flesh of my hips and held me in place as he slowly withdrew. I could feel him; feel every ridge and vein drag out and then in, out and in, over my most sensitive, intimate, area. The slick sounds of our intimacy began to echo around the room as he picked up speed, strong thighs working at a feverish pace. With every thrust he pushed against that one spot that made my legs jerk and eyes water, my arms almost giving out underneath me as the table rattled beneath my weight. With the ferocity of his pounding and the heightened sensitivity he’d curated between my legs only moments before, we both knew that neither of us would last long. The sounds of his ragged breaths and throaty moans alone had me clenching around him already, and I know my constricting muscles already had his hips stuttering as I sucked him in with every thrust.

“Fuck (Y/n)- You’re so fuckin’ tight-”

I chewed on my bottom lip as his desperate eyes met mine.

“Oh yeah? Well I feel like you’re cock is in my fucking ribcage- oh fuck-”

He slipped one hand between us, his large palm resting on my lower belly as his thumb drew fast circles around my clit. The immediate contact on my bundle of nerves had my whole body quivering, the knot of an impending climax already starting to twist tighter and tighter in the depths of my core. The way that Dean fucked me into the motel room table was something that I would be able to feel deep in my soul for the rest of my life - my body and entire nervous system having never been worked in such a feral way before. Dean dropped forward and crushed my body into his - one large strong arm wrapped around my trembling body and kept me pressed against him as his head dropped to the crook of my neck. Soft lips pressed hot kisses against my shoulder, teeth gently nibbling the soft flesh as the coil wound and wound, the wave of orgasmic bliss rising higher and higher as my mind emptied, leaving behind only one thought.

Dean.

He was all consuming - all I could see, taste and smell. All I could feel. Oh God could I feel him; driving me to the brink of pure bliss as he frantically sped up - desperate to seek his own undoing as well as my own. One… two… three more fervid thrusts and the peak he’d helped me ascend to shattered around me as I practically screamed his name, the white-hot euphoria scorching my insides as I clamped like a vice around him.

“Oh shit- (Y/n) I can’t- fuck-”

I grabbed the back of his head and pushed his mouth to mine as he came undone, spilling inside me as he worked through his own white-hot euphoria.

The kiss we shared evolved from hot and needy to soft and wanting - the sensation of hot cum running down the inside of my thigh and cooling against my skin being the only thing to pull me away. Dean continued to lean over me for a moment, looking down at me with an expression that told me he had so much he wanted to say. Instead, he looked down at his release now starting to pool on the floor beneath us, then to the books and laptop that had been thrown across the floor before turning back to face me with the most devilish grin on his face.

“You know that this mess is all your fault, right?”

I scoffed.

“My fault? How is it my fault?”

“Because, sweetheart…” he tucked a strand of hair behind my ear and pushed lightly on the plastic bridge sitting on my nose.

“You put on on those fucking glasses.”

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rubyrubyrubytuesday · 1 year ago

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i am once again blaming hellers for this

#(this is in jest I am a destiel okay)#it could be a wincestie i guess but i think hooker dean shows up way more in destiel fic so i choose to blame them!!!#rrrt blogs supernatural

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maipareshaan · 2 years ago

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Sometimes you see blorbo enthusiasts and you just can't relate while you do the same for your blorbo.

This is about seeing people call Dean 'whore' like idk the emotions that inspire that but i do know the emotions that inspire me to call Sam a whore and ooo they are intense oooo they are rabid, i want that man to go through medieval slut shaming public punishment oooo, parade him naked and spit on him while calling him WHORE.

#Like just no emotions #And just feral emotions #I do think slutshaming sam is more of an ascended thing to do #I can't even say who is my blorbo but like different feelings for different blorbos maybe #Eh i'm clearly missing something #Maybe it has something to do with truckstop hooker dean #But idk the tone #This isn't anything srs obvs just about how we unrelatabledoing the same thing with the other bro is #Also the womencoded thing

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sorryitsmyfirstdayonearth · 2 months ago

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One of the girls

(Dean Winchester x female reader)

Summary You dress up as a working girl for a case. It brings up some memories for Dean, as well as some new fantasies of you. CWs Dean and his history with sex workers, nothing actually happens but Dean's fantasizing. Some seemingly unrequited pining. 18+. 3.7k words

Dean Winchester masterlist ⏐ SPN masterlist

You’re leaned against the side of the Gas Mart, legs stretching long and naked from the high leg of your jeans shorts and the second-hand cowboy boots you picked up God knows where - Dean’s never seen them on you, but he loves them immediately. You’re wearing a sheer red top, tied at the waist to reveal the soft-looking skin of your stomach and to top it all off, a fluffy, short leopard print jacket, that Dean hasn’t pressed his nose into, but can guess exactly what it smells like: dusty, plastic-y and perfect.

To cut a long story short: you look absolutely delicious, a juicy piece of bait that no blood sucker in the world could possibly resist. Dean sure as hell knows he wouldn’t be able to.

This was your idea, even though Dean had it first, and he’s half sure so did Sam. But they’ve both seen enough early 2000s comedies to know that suggesting you dress up as a prostitute would get them slapped. But then you suggested it, and didn’t even make it a big deal. Just shrugged, said: “the vamps clearly have an MO. So I should be the bait, dress up accordingly.”

Sam and Dean made a big show of gallantry about how they couldn’t let you do this, how it was too dangerous. You just raised your eyebrows, a cheeky smile on your pouty lips.

“No offense,” you said, “but I don’t think you’re their type. Not that I wouldn’t pay for the privilege to see you try.” Your eyes roamed over both of them, and while Sam scoffed, then chuckled, Dean couldn’t help but wonder if you really were imagining him in some skimpy, slutty outfit. He sniffs, now, pushes the thought away. Maybe something for another day.

He sits there now, in the driver’s seat of the Impala, his brother next to him, parked far enough away that they can see you but won’t scare away any potentially fangy customers. Both brothers are quiet in the dark of the car, watch you there in the light of the gas station, the way you pop a wad of gum, smacking your cherry red lips so practiced, so perfect, so much like the real thing that Dean wonders, not for the first time, where the hell you learned this.

He knows where he learned it. Learned about this type of woman. They called them hookers back then, but he’s pretty sure that’s not the word you’re supposed to use anymore. Sam would know, but he’s not about to ask him. Because there’s some things his little brother doesn’t need to know.

Dean grew up in the weird intersection of not having a single woman as constant in his life and wanting to fuck pretty much every one of them he came across, his budding sexuality something he suddenly came upon, no warning, no guidance. Only ugly bathrooms, TV blaring in the next room, doing it dry, then with lotion, once with soap that got into his urethra and made him sure he was gonna pass out. Life was just an endless string of faceless women, and that was even before he started having sex. Waitresses, hotel maids, neighbors in adjacent rooms. And the hookers. Prostitutes. Shit, he’s not sure which, but they were a constant.

They were sweet to him and Sam. Especially when they were kids. Short skirts and high heels and bra straps and sometimes wigs, but also when they stayed somewhere for a little longer, they knew him and his brother by name, would praise him for taking such good care of Sammy. He’d grin at them, and they’d tell him he’d be a heartbreaker when he grew up.

So now there you are, the sweet girl he’s had his eye on, at least until you joined Sam and Dean full time. Relationships are something fleeting to him and he can barely stay interested. Any woman he gets close to, really close to, is assigned a familial role - mother or sister. He knows there’s something deeply fucked up about that, but he’s too fucking old to change.

He keeps watching you. The gleam of the light reflected on your skin. The way you lean to accentuate your tits and hips. The slight flutter of your eyelids to seem attractive and like you don’t give a shit at the same time. There’s something so innocent about it all. Something pure.

“I’m gonna go see if there’s anything on the other side,” Sam says into the quiet dark, and Dean just barely nods, only half listening. He hears Sammy move, the frame of the car squeaks and then the door, opening and shutting. He’s too busy staring at you.

Sam’s got this whole thing about not paying for it, but Dean doesn’t really get why he’s so uppity about it. Sure, he loves the chase - a low lit bar, drinks, that connection in the air. The kissing. He really, really loves the kissing. But the truth is, it also fills his gut with anxiety. He knows he carries a certain appeal to women, and it’s not often that he’s rejected. He manages to be forward without being creepy and he’s pretty sure he does a good job once he gets down to business too.

But the simplicity of the transaction, the clear lines - there’s something about it he misses. He hasn’t done it in years, not even sure how he would do it anymore. Is all that stuff online now? Or could he still find someone in a motel lobby or a parking lot?

There is one experience he often goes back to, when he needs a little inspiration. She was older than him. He must have been maybe twenty, so it’s hard to say now how old exactly, because to him everyone past thirty seemed ancient at that time. But she wore a wig, he remembers that, blonde so bright it was almost white, short, revealing her slender neck, a little heart tattoo just under her hairline. Had soft lines around her eyes. She smelled of menthols.

She took him to the room she worked out of. Told him to lie on the bed. She took his dick out of his pants and when he reached for her, she tutted, pushed him back down on the bed by his shoulders.

“That’s alright, sweetie,” she said. “Let me take care of you, okay?”

In a way, Dean knew what she was doing. Getting him close with her hand so she wouldn’t have to fuck him for long. But he just couldn’t seem to care. When he finds a hook up, there’s so much he needs to do. He wants the women to have a good time, remember him fondly.

But this woman, kneeling on the bed by his hips, jerking him off, she was taking care of him. Her hands were soft and slippery from the lube she’d used. She kept muttering sweet things to him, calling him sugar and honey and other things.

He was close to coming when she stopped, reached for the condom. Rolled it down on his erection, making a whimper escape him from the sensitivity. Then she climbed on top of him.

She told him how good he felt and how hot he was, but Dean knew it wasn’t real. Still. She was doing it for him. Yeah, she was being paid. But there was something about that. It felt like kindness.

He takes a deep breath, still watching you. Those vampires don’t seem to be in any hurry. You switch your weight from one leg to the other, roll your shoulders. Sigh, and Dean can see even from this distance that you’re getting bored. He grins.

The image comes to him without warning. Him, coming out of the Gas Mart, the same one he’s looking at now, maybe just tugging away his wallet or looking at the receipt. You approaching him from the side and he looks at you, alerted by the movement. He’s only mildly surprised to see you’re wearing the white-blonde wig in his little fantasy. You smile at him, lip gloss freshly applied, eyes wide and lashes flicking suggestively at him.

“Hey there,” you’d say with that sweet voice of yours.

Dean’s hand wanders to his crotch, rubs along the rough fabric of his jeans. He shouldn’t, and he’s not gonna, of course he’s not. He’s just teasing a little, just pushing down on the feeling, but he’s not gonna do anything. He leans his head back, eyes still half open. It makes you blurry in the low light in the distance. But you’re clear as day in Dean’s head.

“Hey yourself,” he says, a small smile on his face. He’s not about to act shocked that you come to talk to him. He thinks it must be pretty darn scary walking up to random men at a gas station in the middle of the night, so he wants to make sure he doesn't make you nervous.

You pop your hip, one hand going to it, allowing him to take in your body, your shape. You’re fucking gorgeous, the prettiest he’s ever seen.

“Looking for some company?” you ask, a little smile tugging at your lips at the cliché sentence, but the truth is, Dean likes it. He purses his lips, looks to the side, then back at you.

“What if I was?” he asks, teasing, and you smile at that, take a step closer to him and Dean gets just a whiff of your perfume - cheap and sweet.

“Then I’d say you just got extremely lucky,” you reply, a broad grin breaking over your face. Dean can’t help himself but chuckle a little. Both of you are going through the motions, but it’s clear that this is a sealed deal. He nods.

“Lead the way,” he says.

You walk ahead of him, and it gives Dean a chance to stare at your ass, your waist, the bit of your neck he can see with your hair tugged into the wig. And more of your smell. He’s not embarrassed to say that that alone is enough to make him chub up. He presses his hand against himself. Does the same in the Impala. But he’s not really there.

You get to your room, unlock the door, push it open. Don’t turn on the light when you do and Dean steps in after you. It’s bright enough to still see you - these places always are. It never gets fully dark out here, always some neon light buzzing, a headlight shining in. It makes you look ghostly, highlights the parts of you he can see.

Dean closes the door behind him, then steps closer to you. You take the time to shrug off your jacket, and while Dean’s kinda sad at the loss of the cheap material, he loves what he sees underneath. He can see the outline of your bra, a severe push-up number, under the sheer shirt. More skin.

He stands close, so close you’re almost touching but not quite, looks down at you, you up at him. It’s quiet in the room, the tension between you drowning out all background noises. Only breathing. He hears the wet noise of your lips pulling apart, the cheap lip gloss separating.

Your hand goes to his chest and you begin pushing him back. He follows the movement until the backs of his legs meet the bed. He plops down on it, and all of a sudden he’s looking up at you, not the other way around.

He raises his hand, carefully. Lays it on your hip. Runs it down, slow slow slow, until his fingertips touch the skin of the back of your thighs. It tickles you and you shift in place, and that grin is back on your face.

“Lie down,” you say. “Lemme take care of you, honey.”

Dean lets go, then shuffles back on the bed. Lies down, head meeting the knotted pillow the motel can’t be bothered to replace until it’s fallen apart. His hands go to his belt as he undoes it. Pops the button of his jeans, then opens the fly before he rests his hands on his chest, lies there and waits.

You appear in his periphery, and he’s not sure where you came from. Dean looks up at you, the way the low light frames you so beautifully. Without breaking eye contact, you climb onto the bed, kneel next to him.

Your hands go to his jeans, and he feels himself twitch in anticipation. You drag down his pants and his underwear and then your hand goes in and you take him out. Your lips part and your eyes go from his face to his cock. You bite a little at the bottom one and then you begin stroking him.

It’s testing, a little too dry, but honestly, Dean doesn’t care. He feels himself harden in your hands, watches as your chest rises and falls. You like this as much as he does.

“This is nice, isn’t it?” you say and Dean nods, his hair scratching against the pillow under him. “We’re gonna take our time, take it slow.” Dean swallows. Young him doing this would be terrified at the clock running out and not being able to pay in the end, or needing the money for food or anything else, and he really doesn’t want some scumbag pimp on his case. But he knows he doesn’t have to worry about that with you. So he nods.

“So nice and hard,” you say, your voice barely above a whisper, so low in fact Dean misses some of the softer consonants, but his brain fills in the missing parts. “Gonna take good care of you, baby.”

His breath shudders, stomach clenches. Your movement is smoother now, your hands gliding, and Dean’s not sure if it’s his pre-come or if you got lube from somewhere, but he couldn’t care less, because your shirt is suddenly gone. He can see the globes of your breasts unhindered, looking endlessly soft. He reaches his hand out, runs it over the left one, the satiny fabric meeting your satiny skin. Fucking perfection.

You lick your lips, pick up your speed a little and Dean’s eyes flutter shut, just briefly.

“Fuck,” he gasps under his breath at the slight twist of your hand, holding him just a little tighter than is comfortable, but he loves it this way.

“You’re so good, Dean,” you say and he blinks his eyes open. “Feel so good. Just relax. Just relax. Let it happen.”

Dean groans, feels the first tug in his balls, the pressure in his stomach. It’s accompanied by buzzing pleasure, but he has just enough wherewithal to not let it take him immediately.

“Can we–?” he says but you shush him.

“I know exactly what you need,” you say. “Don’t I always know what you need?” And Dean can only nod, because of course you do.

You slow your movement, then stop completely, giving him that strange floating feeling he gets when suddenly the stimulation is gone. But it’s not for long.

You’re naked, suddenly, except for the wig, and Dean doesn’t know when that happened, nor does he care, because you raise your leg, straddle him, the impossible soft insides of your thighs pressed against his hips. He kinda wishes you were still wearing the cowboy boots, but he doesn’t have time to focus on that, because your fingers go to your mouth as you collect some spit, bring it to his cock and the feeling of your warm saliva nearly makes him roll his eyes up into his head.

Then you take him in your hand, line him up and start sinking down on him. There was no need for the spit since you’re warm and wet, and that’s about the last coherent thought Dean has for the night.

You moan loudly as you sink lower, envelop him, the most intimate embrace. Dean’s hands go to your waist, to steady you as much as himself, because this? It’s the best he’s ever had.

Your hands rest flat on his stomach and then you’re all the way down, Dean buried as deep inside of you as he can go, and a soft shiver goes through you, one that Dean can feel where he’s snug inside of you as well as hear in your soft gasp and see in the dreamy smile on your face. You could be moaning and frowning and screaming his name, but right now, he wants you all soft and happy.

You start rolling your hips and Dean needs to press his head back into the pillow again, your wet heat dragging along him, the walls of your pussy kissing his cock. A soft whine leaves you too but when Dean looks up at you again, you’re still smiling.

His hands are still on your waist and he uses the hold to push you back a little. You understand a second later, lean back, one of your hands going to his leg instead. He can look at you perfectly this way and from the slight way your eyebrows go together he knows the position is having exactly the effect he wants it to have.

“Oh fuck, Dean,” you gasp, surprised by your own pleasure, maybe. Dean lets one of his hands wander lower as you concentrate on riding him. He presses it close to your entrance, where he’s appearing and disappearing inside of you, the fucking most perfect sight in the world, and when some of your wetness transfers to his thumb, he brings it up to your clit, presses against it.

It makes your movement stutter, makes you gasp, and then you find your rhythm again, a soft chuckle leaving you as you adjust to his touching.

“Baby,” you say and now it’s Dean shushing you. He wants you to concentrate on how good you’re feeling, not on singing his praises.

You keep going, keep rocking against him, and then your noises start becoming louder. High noises, feminine noises, soft, girly noises, sounds he’s never heard you make in real life, hiccuping. Dean feels you grow tighter around him, warmer, and he picks up the flick of his thumb, the fingers of his other hand pressing into your skin. Despite the fact that the position is so perfect, you lean forward again, hands on his front. Because you want to look at him.

You’re going fast now, mouth open as you keep his gaze, sweat building on your chest and on your brow. Dean just keeps helping your movement, keep the rhythm, keep it steady.

He reaches one hand up, his index and middle finger connecting with the strands of the wig, pulls gently and it drops off you. Your real hair opens from how you rolled it up to get it in, falls and it’s really you, all of you, there on top of him.

“Right there,” you gasp, you fingernails digging into his skin and then Dean pushes up into a sitting position, arms going around you as he holds you tight, thrusts up at you and you cry out, one hand on his shoulder, one in his hair, and holy fuck, you’re about to come, he’s about to make you come for the first time ever. He presses his mouth against the skin between your perfect tits, drives up hard and then for a moment you sound like you’re in pain, shaking, then no sound and then the loudest, longest moan he’s ever heard, and he’s right behind you, just a little more, just one more thrust, one more and–

Dean flinches at the knock on glass, eyes flying open, heart punching him in the nipple for a second with how hard it’s beating. He looks to the side, and it’s Sam, arms widening in what is clearly the sign language equivalent of what the fuck. Dean looks down - no, his jeans are closed, and although his hand rests dangerously close to his crotch, he doesn’t seem to have made a mess.

Well, the other reason he can tell he didn’t come is cause he’s hard as a rock.

He rubs a palm over his face, sniffs, just as Sam rounds the car, opens the door on the other side. Did he fall asleep? Is that what happened?

“Dude,” Sam says, just as he folds his long body into the passenger seat. “We’re on a case with vampires and you decide this is the perfect time for a nap?” Dean opens his mouth to sass right back, when the door to the backseat opens too and you get in.

No wig, no cheap perfume, but you duck your head, scoot to the middle of the bench. Dean swallows, awfully aware of the circus tent he’s sprouting.

“Get off his ass, Sam,” you say, taking off the leopard print jacket - the t-shirt underneath is a lot less sheer than Dean remembered, plus no sight of tits pushed to the high heavens. You reach for the jean jacket you abandoned and lay it over your shoulders. You push the leopard number away with two fingers.

“That thing was giving me an allergic reaction,” you say, throw a quick smile at Dean. He huffs.

“What, uh, what happened to the vamps?” he asks, looking at Sam. He takes a deep breath, sighs.

“No sign of them,” he says, shaking his head. “Looks like we’re back to square one.” You lean forward, arms crossing over the backseat of the car.

“Maybe my acting just wasn’t good enough,” you say, raising your eyebrows at Dean in a self-deprecating manner. All he can do is grin.

“They’re missing out, is all I can say,” he says, not aware how that sounds before it’s out.

He can feel Sam throwing him a confused, potentially disturbed, look, but Dean doesn’t care. Because you look surprised and then amused.

“Mmh,” you say and then Dean needs to turn around, get the car started because he’s pretty sure if he keeps looking at you he loses any chance of hiding his erection. He turns the key, Baby starting to purr under him, and starts driving her off the lot.

Only once the lights of the gas station are far behind he dares to look in the rearview mirror. You’re leaning against the bench, looking out into the night. There’s a soft smile on your lips and when you suddenly turn your head, look back at him and meet his gaze, Dean swears he can feel you back in his lap, where you belong.

#supernatural #spn #fanfic #dean winchester #fanfiction #spn fanfic #dean winchester x you #dean winchester x reader #sorry's fics

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rizlowwritessortof · 1 month ago

Text

Friends and Lovers

You and Dean were the best of friends - until the night something happened that changed everything. But when you tried to move on, Dean was always standing in your way. And when you signed up for an online dating service, he was a total dick about it. What the hell did he want from you, anyway??

Pairing: Dean Winchester x Reader

Word Count: 4719

Warnings: Nothing but a little angst, arguing and smut

Square #8 for my @jacklesverse-bingo 2025!! Prompt for this one was: Online Romance. Hope you enjoy!!

“It’s just a bad idea,” Dean argued, glaring at his laptop to avoid looking at you.

“Dean, people do online dating all the time.”

He scowled at you. “People. Maybe. I still think it’s stupid. But the thing is, we’re not ‘people.’ We’re hunters.”

You rolled your eyes. “What the fuck does that have to do with it?”

He let out a long-suffering sigh. “Do you know what internet dating is to monsters? A fucking take-out menu.”

“Oh, my god. You are so dramatic.”

“These things never work out well. I know.”

Sam snorted softly from his seat at the end of the table. “Impala ‘67,’” he muttered, and Dean shot lasers his direction.

“Shut up, Sam!”

You closed your laptop and glared across the table at him. “Look, I’m sorry about your hooker and her demon pimp. But this site is different.”

“Right.”

“You won’t even listen, so this – this discussion is over.” You stood up, grabbing your laptop and moving to leave the room.

Dean leaned forward, his eyes sparking with anger as he raised his voice. “Just a bunch of assholes lying to you, that’s what you’re gonna get. And you’ll be lying to them, because you can’t be totally honest about who you are to some clueless civilian.”

That stung. “Fuck you, Dean!” you fired back as you stormed away, heading for your room. You slammed the door with extra emphasis, and the sound echoed through the bunker. You let out a muffled scream of frustration, dropping your computer onto the desktop and throwing yourself down on the bed.

He was so stubborn. You knew he was just being protective – over-protective – and that he wanted to keep you safe, but nothing fired you up more than his obstinate refusal to listen to someone’s viewpoint that didn’t align with his. He pushed your buttons in a way that no one else had ever done, and it pissed you off that you let him get to you like he did.

The argument had been going on for days. It had all started when you signed up on the dating app, Friends and Lovers. Their whole approach was the antithesis of the hook-up sites that were basically there for booty calls. No photos were allowed, each person signing up was assigned a generic name, once they filled out a form stating their pronouns, relationship preferences, general likes, dislikes, and interests. They encouraged setting up private chats, spending time getting to know each other for a few weeks before actually meeting in person. The whole premise was that building a friendship first would be a stronger foundation for a lasting relationship instead of basing everything on looks and physical attraction.

And if Dean hadn’t been snooping on your computer, he wouldn’t have known anything about it. Ok, fine, he had just asked to borrow it, and you had left the app open by accident. But he’d been riding your ass about it ever since.

This was all his fault in the first place. That night a few months ago had fucking ruined everything. Before that, you had resigned yourself to being his bestie without benefits, no matter how you really felt. Because you knew he didn’t feel the same way, so you just pushed it down and enjoyed what the two of you did have together. And then he had to go and give you that spark of hope for one quick second, that glimpse of what could be, and it had fucked it all up.

You woke gradually, reluctant to leave the warm, cozy comfort of sleep, your eyes fluttering open and blinking slowly. Dean’s green eyes were right there, looking down at you as he brushed a lock of hair from your eyes. “Hey, sleepyhead. You didn’t even make it halfway through – lightweight,” he teased.

He was so close. It finally dawned on you that you were laying on his shoulder, and he smiled in amusement at your sleepy confusion. “Are you with me?”

“Yeah, I think so. Wow, I crashed,” you muttered, yawning.

“Big time.” You looked up at him again, a sleep-drunk smile on your lips. He was still staring down at you, his smile slowly fading. Something in his eyes changed as he looked at you, moving closer, and closer, and you wondered for a second if you were still dreaming, because it looked like – oh, shit, it felt like – he was going to kiss you. You let your eyes drift closed again, and you could feel his breath, could sense his lips almost brushing against yours.

And then he froze. He stayed there, motionless, for a moment, then straightened up so suddenly that your eyes opened again, searching. He was sitting bolt upright, stiff, jaw clenched as he looked away from you. Then he leaned away, rising to his feet after you sat up in response, disoriented, your head spinning a little at the sudden change in the atmosphere.

“Guess we should hit the sack, huh? G’night.” And then he was gone, leaving you feeling suddenly cold, alone, and utterly rejected.

Your relationship – whatever it was – hadn’t been the same since. He had pulled away, keeping you at arms length, and you had pulled away, too – hurt and confused. And the longer it had gone on, the bigger the rift had grown.

Dean sat there staring at his computer, his brows bunched as he gnawed at his lower lip. Sam fixed his eyes on his brother, his lips pressed together as he shook his head. “Don’t do it, Dean.”

Dean frowned back at him. “Don’t do what?”

“Whatever it is that you’re thinking about doing.”

Dean reared back in his chair, his arms folded across his chest. “How do you know I’m thinking about doing anything?”

“I can practically read the thoughts going through your brain just from your expression.”

“Shut up, Sam.” Dean leaned up to his laptop again, and Sam spoke again, more softly this time.

“Dean, I’m just saying, some things you may not be able to come back from.” Dean let out a frustrated sigh, but Sam went on. “Maybe you should just talk to her.”

When his brother looked up this time, his eyes were clouded. “She won’t talk to me. She hasn’t for a while now.” He closed his laptop and pushed back from the table. “If we’re done with therapy, I’m gonna go to bed.” He ignored Sam’s accusing stare as he left the room, heading for the peace of his own bedroom.

He pulled off his boots and sat on his bed, pillows propped behind his back, and opened his laptop. The home page of the dating site was still open there, and he looked at it for a few minutes, Sam’s words still ringing in his ears. “Fuck it. What’s the worst that can happen?” he muttered to himself, and started filling out the form.

You hummed a tune to yourself as you stared into your closet, debating on which shirt to wear with your jeans. It was your first meeting with ‘Tom,’ and you had decided to go casual. You were just meeting him for drinks, wanting to keep everything low-key to start with. Not that you still weren’t nervous, but the two of you – well, ‘Tom’ and ‘Dana’ - had been chatting regularly for three weeks now, and he seemed like a pretty nice, easy-going guy. You seemed to have a lot in common – that you could share, anyway – and he made you laugh. You both constantly referenced and quoted movies and TV shows, liked the same type of food, and he came off as pretty down-to-earth. You were looking forward to getting to know a little more about him – like his real name – and that was a good sign, right? It had been so long since you had an actual relationship with potential that you weren’t even sure how to act. The plan was to keep things loose and not get too eager to jump into more before you were both really ready. If you were ever really ready.

Neither of the guys were in view when you walked through to go to your car. You were a little relieved, not wanting to answer questions anyway. Dean would just get that expression you hated, or start in again about meeting up with some guy you didn’t really know, and you breathed a little sigh of relief. It was sunny outside, and you allowed yourself a dose of cautious optimism as you drove to town.

You walked into the restaurant, targeting a table in a back corner where you could have a little privacy. You were really looking forward to meeting ‘Tom’ in person – your conversations had been far easier than you’d expected. He had a goofy sense of humor, and you’d laughed more online with him than you had in months. You just wanted to enjoy spending time with someone who understood you. He seemed to get you.

The waitress showed up and you ordered a draft beer and some appetizers. He would be showing up soon, but you didn’t want to be sitting there staring at the door when he walked in, so you took out your phone to keep yourself busy. When you heard footsteps, you looked up, your eyes widening as you saw the last person you expected or wanted to see standing there. Dean. “What the hell are you doing here?” you asked, fighting to keep your voice steady.

He looked a little nervous, staring down at his boots as he answered. “I’m supposed to meet somebody here.” He took a deep breath, finally looking you in the eye. “Her name is ‘Dana.’”

Your eyes went wide, your mouth opening wordlessly as you stared back at him. Then you shoved your chair back, almost knocking it over, and pushed your way between the waitress and Dean as you rushed towards the door.

“Hey!” the waitress said, barely managing to keep from dropping the beer and food you’d just abandoned. She set it all down on the table and looked back towards the door. “Great. Now who’s gonna pay for this?”

Dean pulled out his wallet and dropped a couple of twenties on the table. “Keep the change.”

She smiled at him in relief and thanked him. “Listen, you’d better go after her. She seemed pretty pissed.”

Dean moved towards the door, muttering under his breath, “You have no idea.”

When he stepped outside, he spied you, leaning against the side of your car, arms folded across your chest, staring hotly in his direction. “Shit,” he breathed, walking towards you, trying to come up with words.

“This is a new low for you, Winchester,” you spat, your seething anger making your voice a little shaky.

“I know it was stupid. Sammy told me not to do it.”

“Sam knew you were doing this?!”

“No – he didn’t know. He just knew I was thinking about doing something, and he told me not to.”

“Why? Why would you do this? I really thought I was talking to a nice, normal guy, thought maybe for once… But no, you were right, it was just another asshole lying to me on the internet.”

Dean ducked his head, his jaw working as he felt the blows from her well-aimed words. “I’m sorry. I never meant…” He looked up at her, shaking his head. “I didn’t do this to hurt you.”

“Then why the hell did you do it?”

He hesitated for a second before answering. “Because maybe I’d like to get back to the way we were before.”

“Before what?” You shouted, your voice still brittle with anger, and he returned fire before he could pull it back.

“Before I fucked it all up!”

You were silent for a second, staring down at the ground, the sounds of your raised voices seeming to linger in the air between you. You finally looked up, hurt in your eyes as you spoke quietly. “Well, this didn’t exactly fix things, did it?” You turned and opened your car door, climbing inside and closing it without another word. He stood there watching as you drove away, head hung low, wishing like hell he had listened to Sam’s advice.

It was almost unbearable in the bunker for the next couple of weeks. It was miserable trying to avoid Dean while living in the same space, and you finally got up one Saturday morning, deciding it was time for a change.

You went out to the kitchen and grabbed a cup of coffee, ignoring the surprise on the brothers’ faces at your appearance. “So,” you ventured, “it’s been too long since we all hit the bar together. Tonight we’re going out for drinks. We’re gonna get drunk and we’re gonna have fun. You know, like we used to.” You turned on your heel and headed back to your room leaving them wide-eyed and jaws dropped in the kitchen.

That evening, you stood in front of the mirror in your room, critically eyeing your reflection. Black lace thigh-high stockings, short denim skirt, and a clingy silver-grey top that draped gracefully low, providing a tempting view of soft curves and a generous portion of cleavage. You smiled, happy with the results of your preparations, and turned to put on your denim jacket. You’d save the unveiling for later. One way or another, before the night was over, Dean was either gonna make a damn sandwich or get the hell out of the kitchen.

You sat at the table with the boys for a couple of beers, even though the conversation was sparse and stilted. Sam tried his best to keep things going, but Dean was obviously still not up to much small talk. When you stood up and shed your jacket before heading to the bar, the expression on his face was everything you had hoped for.

You could feel his eyes burning into you as you made your way to the bar, ordering a shot and chatting with the bartender. It wasn’t long before a guy with an expensive haircut and too many buttons undone on his shirt came sidling up to you – exactly what you had been hoping for. When he asked you to dance, you gave him a promising smile and let him lead you to the dance floor.

Dean sat at the table, staring in your direction with a death grip on his beer. You were out there having a great time, laughing and dancing, flirting your ass off from the looks of it. He ground his teeth together, then slammed the rest of his beer down in one go, standing up and stalking to the bar for another. No, fuck that, he wanted whiskey. A double.

He polished off the whiskey and ordered another before heading back to the table. Sam was watching him, but wisely pressed his lips together and kept his mouth shut. Dean’s eyes drifted back to the dance floor again, just as another song began, this time with a heavy, sultry beat. His blood came to a low simmer as he watched the asshat you were dancing with move in close behind you as you turned your back, his hands possessively on your hips as you swayed to the music. Then you did a sexy little dip and roll, and Dean felt his mouth go dry, followed by his temper reaching the boiling point.

Sam said his name as Dean stood up, killing his whiskey in one swallow, but the blood rushing in his ears drowned it out as long, purposeful strides carried him over to you. “We need to talk,” he demanded as you stopped dancing, staring up at him incredulously.

“Seriously, Dean? Right now?”

He grasped your hand with a firm grip. “Right now.”

You shrugged and rolled your eyes at your dance partner when he protested, but Dean’s murderous expression cut him off, and he backed away, hands held out in surrender. “Yeah, whatever, dude.”

“Good choice,” Dean muttered, and to keep from making a scene, you let him lead you through the bar and out the front door. He didn’t stop until the two of you were in the back parking lot next to the Impala, and then you jerked your hand away, planting your feet and glaring up at him.

“What? I was dancing, having a good time. What is so goddamn important?”

“Dancing? Really? He was practically dry-humping you on the dance floor!”

“So?” You shouted the word at him, anger sparking in your eyes. He opened his mouth, then closed it again, no words coming to his rescue. “Why do you even care?”

His jaw worked as he tried and failed to look you in the face. “Because I do.”

You moved a step closer to him. “Why?”

He huffed out a frustrated breath. “I just do.”

You rolled your eyes. “Right. Because we’re such good friends, and that guy is no good, and you’re just trying to protect me. Blah, blah, blah.”

“Yeah,” he said defiantly, and you shook your head.

“Not good enough. Every guy in the world that I look at can’t be bad news, Dean.”

His lips were pressed tightly together, the dimples that always deepened when he was angry or frustrated showing clearly in the dim light. “I don’t trust him.”

“You don’t trust anybody with me. Why don’t you just tell me why?”

“I told you why.”

You jabbed a finger his direction, your voice rising. “If you don’t tell me the fucking truth, I swear to God I’m going back in there and do him right on the dance floor!”

His glare sent a little thrill up your spine. “The fuck you will.”

“The fuck I won’t.” You whirled around and took a step back towards the bar, but he grabbed you, jerking you back and turning to trap you between his body and the car. You shoved at his chest in frustration. “Why don’t you just admit how you feel?”

“What’s that supposed to mean?”

“You know what it means.”

He looked away, avoiding your searching eyes. “No, I fucking don’t!”

“Admit that you want to be with me.” He still avoided looking at you, and you bit at your lip hard, then forced the next few words out, fear making you feel a little sick. “If you don’t want to be with me, Dean – you’ve gotta let go. I can’t – we can’t keep doing this.”

There was a tense pause, a few seconds where you thought you might have to just walk away. When he spoke, his voice was hushed, strained. “I can’t stand watching some asshole touch you the way I want to touch you.” He finally looked at you, the intensity in his gaze making your heart jump. “Yeah, I want you, so damn bad it scares the hell out of me.”

You stared up at him, reading the truth in his eyes. “Fucking finally,” you said, standing on tiptoe, your arms wrapping around his neck as you kissed him, his body warm and solid as he crowded you against the car. He deepened the kiss with a low groan, one hand coming to rest at your waist as the other trailed slowly from your jaw down the length of your throat, finally finding your breast and kneading at it as you arched into his touch.

When you finally stopped, he leaned his forehead against yours as you both panted for air. “Where are your keys?” he asked, and you reached into the pocket of your skirt to pull them out. “I’m gonna take these in to Sam. I’ll be right back.” He kissed you again, soft and quick, and backed away, letting you open the car door and slide inside.

He was back in a flash, slipping in beside you. He leaned in to kiss you again, then raised his head, pulling his bottom lip in as if he were savoring the taste of you. “You ready?” he asked, his voice raspy and low, and you smiled, your eyes shining.

“So ready.” His lips curved in a sexy smirk as he started the car and backed out, his hand warm on your lace-covered thigh as you headed down the road.

You scooted a little closer, returning the favor and tracing little patterns on his jeans, feeling the muscle shift beneath your fingers as he braked at the stop sign at the edge of town, then stepped on the gas. His hand was stroking slowly over your thigh, moving a little higher each time until he slipped under the hem of your skirt, and he swore under his breath as he touched the bare skin above your thigh-high. “Not sure we’re gonna make it all the way home, sweetheart,” he managed to get out, and you laid your head back on the seat next to his shoulder, smiling up at him.

“I’m okay with that.”

Dean took a sharp turn onto the next gravel road, and by the time he found a trail where he could pull off and park, you had gotten your boots off. You moved so he could slide out from under the steering wheel, and he watched you with hunger in his eyes as you finished shimmying out of your skirt and began to peel off your shirt.

He watched every move as you climbed aboard his lap, nothing but black lace and silky skin, and he swore as you settled on top of him. “Jesus, baby,” he said, shifting his hips a little as you trapped his hard-on between you. “You know you’ve been driving me crazy for months now.”

He was reaching for you, but you grabbed his hands, holding them against his chest as you fixed him with a stern stare. “Well, whose fault is that?”

He ducked his head with a rueful smile. “Mine. Totally mine.” He looked back up at you as you nodded.

“Damn straight.” You tilted your head, an evil glint in your eyes, then leaned forward and gave a gentle tug on his lower lip with your teeth. “I should make you wait.” You couldn’t help but laugh when a little whine escaped his throat as he looked at you with the most pathetic sad-puppy face you’d ever seen. “Awwww,” you cooed as you bent to kiss him, shifting your hips and making him groan at the friction.

You finally let go of his hands, and then they were everywhere, exploring, squeezing, grabbing handfuls of your ass and pushing, rubbing you rhythmically against his hard cock. You raised your head, letting it drop back as you lost yourself in the sensations. “Are you gonna be mad at me if I ruin these?” he asked, plucking at the waist of your panties.

You lowered your chin and looked into his eyes. “I don’t care if you set them on fire, as long as it ends up with you inside me,” you said breathlessly, watching his face as he swore softly and moved his hands to one side of your hips, then the other, ripping the lace apart.

“Lift up for me, sweetheart,” he said, his voice a little breathless, and he tossed the ruined scrap of cloth to the floor of the car before reaching under you to cup your pussy in his hand. “Christ, baby, you’re so wet. Gonna let me slide right in, aren’t you?”

“Yes,” you whimpered, “Hurry up, I need you.” You were fumbling at his zipper, and he chuckled softly, pushing your hands aside and taking care of it himself, shoving his clothes down as far as he could reach with you straddling him. You reached to hold him steady as you centered yourself over him and sank down on his cock, inch by delicious inch until he was fully buried inside you, so deep it ached in the best possible way.

You squeezed your eyes closed, overwhelmed for the moment. When you opened them again, Dean was watching you intently, and he cupped your face in his hand, leaning in to capture your lips in a lingering, tender kiss. “Sorry I waited so long,” he whispered, then kissed you again, slanting his mouth over yours with a moan as you opened to him, your hips grinding against him as he bucked upwards in response. “So – fucking – perfect,” he groaned in between kisses, each word emphasized with a thrust, and you reached up to brace your hands on the Impala’s roof, bearing down to take him as deep as possible.

“Dean! Fuck…” you managed to utter breathlessly as he bent his head to bite and tug at your nipple through the lace of your bra. The car was rocking and creaking in rhythm with your motion, you and Dean both panting as you fucked each other with the reckless need of passion too long suppressed.

Your orgasm hit you just when your thighs were trembling in exhaustion, electricity firing through your veins, his name a keening cry as you came undone. Dean swore as you clamped tight around him, a velvet vise that soon sent him over the edge, and he flooded you with his release, pulling you close to his chest as you collapsed against him with a whimper, your strength spent.

You clung to him, a helpless little whine smothered against his shoulder as an aftershock shuddered through you. His arms wrapped around you tight, crushing you to him as if you were going to disappear. “I got you, baby,” he said softly. “I got you.”

After a time, you sat up, leaning in to kiss him before looking into his eyes with a sweet smile. He gave you a lazy, crooked smirk in return, his head resting back against the seat. His eyes roamed over your face, then down to your chest, warming as he took in every detail of your breasts still covered in black lace. “Didn’t even get to see,” he muttered, and you laughed softly, reaching to stroke your fingertips along his jaw line.

“Well, take me home, and you can see anything you want,” you said, your smile growing as he arched an eyebrow, his cock twitching inside you. “Or we can just stay here, I guess,” you teased.

“Let’s go home, give my memory foam something to remember,” he rumbled, leaning up to kiss you. He shrugged his flannel off his shoulders, and you helped him take it off. “Here, you can use this if you wanna clean up a little, since somebody ruined your underwear.”

You moved away from him with a kiss and a sigh, getting dressed while he adjusted his clothes. He slid back behind the wheel, and you tucked yourself under his welcoming arm for the ride home.

The bunker was quiet when you got there, and the two of you made your way to Dean’s room, whispering and giggling, stealing kisses like a couple of teenagers who had broken curfew. When you made it inside, he closed the door behind you and pulled you close for a long, slow kiss, your arms around his neck. He finally let you go, and you sat on the end of the bed, taking off your boots and then peeling your stockings off as he watched appreciatively. “Hey, what do you call that little move you did on the dance floor tonight?”

You looked up at him, your eyes sparkling with mischief. “You mean this?” You stood up and shifted your hips in the little dip and swirl that had shifted him into action at the bar, watching him catch his tongue between his teeth as he moved closer to you, his eyes following every move.

“Mmmm, yeah. That.”

“Well – I call it…” You pulled your shirt off over your head and looked up at him through your lashes. “Bait.” You laughed as he shook his head, a slow grin curving his lips before he pounced on you and tackled you to the bed.

Sam paused for a second in the hallway outside on the way to his room from the shower. The sounds of muffled laughter and a little shriek from you made him smile, and he nodded his head in approval. “It’s about time,” he mumbled to himself, then went on his way.

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#friends and lovers #jacklesversebingo24 #dean fic #dean x reader #dean angst #dean smut #tag list 1

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