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hintsofhoney · 3 months

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Ladies With Experience

Paring(s): Dean Winchester x F!Reader

Summary: When Dean makes an off-handed comment about "preferring ladies with experience", you try (and fail) to not let it get under your skin. You're a virgin, but you've done just about everything else, and when you talk to Dean about it, he offers to be your first. He's your best friend, and you've been in love with him forever... who are you to deny him?

Tags: smut, first time, virgin!reader, dom/sub dynamics, dom!dean, p in v, oral (female receiving), spanking, fingering, not-so-innocent reader

Word Count: 5k

A/N: As always, thank you to my loves @wayward-dreamer and @makeadealwithdean for beta-ing. Would be nowhere without you two 🥰

You can also read me on Ao3!

DEAN WINCHESTER MASTERLIST | SUPERNATURAL MASTERLIST | MAIN MASTERLIST

“Anyways, let’s say you’re right, fine. Who would want virgins?”

You know Sam didn’t mean it like that , and you felt stupid for letting it bother you. For letting this case bother you.

“You got me,” Dean replied with a shrug. “I prefer ladies with experience.”

And there it was, like a punch straight to the gut. You hated that it hurt you as much as it did. So what, you’ve never had sex. But you’ve done almost everything else. You knew what you liked and what you didn't. You’ve been around the block a few times with the various sex toys in your nightstand drawer. It’s not like you weren’t experienced at all . But that didn’t make Dean’s words hurt any less. You swallowed down the burger and fries from lunch that were threatening to come up, before standing up from your seat at the small motel room table.

The brothers looked at you, eyebrows raised.

“I — bathroom,” you managed, before quickly making your way there, slamming the door shut behind you.

Staring at your reflection in the dirty bathroom mirror, you let the tears fall. Silently, you wiped them away as Dean’s words echoed in your head, and you hated that you loved him. Hated that you’d never be ballsy enough to admit it to him, especially now.

Something like five minutes passed and you knew you didn’t have long before one of the boys — likely Sam — would come knocking to check on you. You flushed the unused toilet so they wouldn’t suspect anything and turned on the faucet, splashing your tear-soaked face with cold water before using a hand towel to wipe it dry. When you emerged, the guys were packing up their duffels.

“Did you find them?” you asked, hopeful.

Dean checked his gun, before flipping the safety on and stuffing it in the back waistband of his jeans.

“I sure as hell hope so, ‘cause if I’m about to crawl through the goddamn sewers for nothing —”

“They’re down there, Dean,” Sam replied, giving him a pointed look. He turned his attention to you, and if he had noticed anything off, he hadn’t let his face show it. “You coming?”

You grabbed your gun off the dresser and holstered it in reply.

Six hours later, the three of you were sweaty, panting, and splattered in blood after a close fight with dragons in the sewers. Thankfully, you hadn’t had to wade in any actual sewage. You hadn’t said a word to either brother since you had gone to the bathroom six hours ago, and to keep them from growing suspicious of your sudden silence, you opted to take a nap in the backseat of the Impala on the way back to the motel.

You stirred awake as Dean pulled into the parking lot, barely conscious enough to catch the end of the brothers’ conversation.

“I’ll get her,” Dean said.

Sam nodded and got out of the car, gently closing the passenger side door before heading inside.

You rubbed your eyes, blinking away the sleep in them as Dean’s face came into focus. He was looking at you over his shoulder, one arm resting on the top of the front bench seat.

“Mornin’, sunshine.”

It took a moment for the feeling you had been filled with prior to your nap to come back to you, his words from earlier echoing in your head. I prefer ladies with experience . You shot him a cold glare.

“Alright. What’d I do?” he asked, turning in his seat to better angle himself towards you.

The question caught you off guard.

“I don’t know what you’re talking about.”

“You haven’t said a word since we left for that hunt, Y/N.”

“How do you know Sam didn’t do something?”

He replied with a knowing look.

You stared at your hands, clasped together in your lap, and muttered, “It’s nothing. Stupid.”

“C’mon, talk to me,” he urged.

You hated this. How easy he was to talk to. How you had always been able to tell him what was on your mind.

But not this . You couldn’t tell him this.

You shook your head.

“Hey,” he said softly, shifting in his seat. He was fully turned around now, reaching out to tilt your chin up, forcing you to look at those green eyes. “Talk to me,” he repeated, no room for argument in his words.

“I can’t,” you whispered. You wanted to throw up. He was your best friend, and you were utterly, irrevocably, head-over-heels in love with him. He preferred girls with experience, and you had none. Not in the way that it mattered. And he had known that, thanks to a late-night stake-out game of Never Have I Ever .

His jaw clenched. “You can tell me anything, you know that.”

You briefly met his gaze. You couldn’t hold it for long.

“Was it something I said?” he prodded.

You stared at the buttons of his open flannel, your eyes quickly darting up to meet his in silent confirmation.

He sighed, pulling his hand away from your face and folding his arms on top of the backseat, resting his chin on his forearm.

“Do I at least get a hint?”

“Dean, I —”

“C’mon, Y/N. You’ve never not told me anything.”

“Why are you pushing this?”

“Because I can’t stand not talking to you.”

Your heart leaped at that confession, however innocent it might have been.

“I’m talking to you now, aren’t I?”

“Because I’m making you. You would have silent treatmented me into next week.”

You didn’t respond.

He sighed again, defeated. “Y/N, c’mon. Please? Whatever I said, I’m sorry. I’m sure I didn’t mean it.”

“You didn’t mean that you ‘prefer girls with experience’?” you retorted quite sassily. The question tumbled out before you even had time to think of the implication that came with asking it.

Dean opened and closed his mouth like a damn fish.

“Thought so.” You began to move to make your way out of the car, when Dean reached out and grabbed your wrist.

“No,” he finally said. “I didn’t mean it.”

“It’s okay if you do. I told you, it was a dumb thing to be upset about.”

“No, it’s not. I didn’t stop to think about how this case might have been affecting you. You know I wouldn’t have let anything happen to you, right?”

You swallowed, nodded. His hand felt like fire around your wrist.

“But for what it’s worth, I wasn’t serious. I don’t prefer anyone one way or the other. Sex is sex. If anyone’s willing to have it with me, I consider myself lucky.”

“Romantic,” you quipped.

A smile tugged at his lips. “I could show you, y’know.”

You almost threw up right there in the backseat. Your eyes grew wide.

“What?” you croaked.

“Well, if you’re worried about not having any experience… I just mean I’d be happy to, y’know. Show you the ropes.”

“… Of sex?” Really, you thought it was cute that he had this misconception of you. You knew about the ropes. You’d just never been tied up with them.

“Of whatever you want.”

“You think I want to have sex with you?” It came out harsher than you meant it to, like part of you still thought you could hide the fact that you were in love with him. Like if you just joked it off it would go away, and you wouldn’t have to cross this line with him, even though you so badly wanted to. But you had to protect yourself, your heart.

You didn’t miss the flash of hurt in his eyes.

“No, that’s not what I —”

You suddenly felt the need to clarify your question.

“No, I — I didn’t mean it like that either.”

Dean’s face morphed into one of confusion. “…So you do want to have sex with me?”

Your cheeks flushed red, and your throat bobbed. “Uh…”

“Forget it, stupid question, you don’t have to an—”

“Yeah,” you answered, your voice barely above a whisper. Fuck it. Who were you to hold yourself back from the one thing you’ve been wanting for years? You cleared your throat. “Yeah, I really, really do.”

Dean’s eyebrows shot up to his hairline. “Seriously?”

“Oh, cut the shit, Dean. Like you’re surprised. Everyone wants to have sex with you.”

He scoffed. “ Everyone , Y/N, really?”

“There are literally smutty fanfictions written about you,” you replied, reaching into your back pocket for your phone, dead set on proving your point.

“Gross. And Becky doesn’t count as everyone.”

“Actually, Becky only writes for Sam.”

You realized what you said at the same time he did, and he eyed you suspiciously.

“Why do you know that?”

God dammit. “I don’t. I mean — I — like, she obviously loves Sam. So, like, she wouldn’t write porn about you. Obviously.”

“Uh huh…” There was an uncomfortable silence for a beat or three. And then, “How much smut have you read about me?”

Your face felt like it had just been rinsed with fucking lava, and you knew it probably looked as red as it, too.

“None!” you exclaimed, way too quickly.

Dean smirked. “You do really wanna have sex with me,” he remarked, like he couldn’t believe it.

“Trust me, the urge is fading by the second.”

His grin disappeared almost instantly. “Would it help if I told you that I think about fucking you all the time, too?”

“Well, I don’t think about it all the —”

“Y/N.” He said your name like a warning, and the tone of his voice settled right in your core.

“Yeah,” you squeaked. “Yeah, that helps.”

“Good,” he smirked, before grabbing his phone from beside him.

“Uh… What are you doing?” You watched as he scrolled for a second, pressing a button before putting the phone to his ear.

“Telling Sammy to beat it.”

Your eyes grew wide. “What!?” you whisper-yelled. “No! Just — we can just do it back here!”

He gave you a pointed look. “I’m not taking your virginity in the backseat of my car, Y/N.”

“Why not!?”

“Because we’re not sixteen, for one. And for two… I wanna make it special.” He rushed the last bit out, like he was embarrassed to say it. And he should be. You cringed as you heard it.

“Oh my God,” you began.

“Shut up.”

“You did not just say that.”

“Shut up. Sam, answer your phone, God dammit!”

“I have done, like, almost everything else, you know. In the backseats of many, many cars. You don’t need to make it special for me, Deano,” you teased.

“For the last time, shut your mouth, or I’m gonna shut it for you,” he said, the look he gave letting you know he wasn’t in the mood to play. No, he wanted to fuck you. Beyond that, he wanted to dominate you. And you were more than happy to submit.

You might have been a virgin physically, but mentally? Mentally, you’d probably give Dean a run for his money.

Sam didn’t answer. Naturally. He was probably in the shower, but you were kind of grateful because as much as you wanted Dean, you didn’t want to make Sam uncomfortable. Or worse, give him any reason to give you the talk . Because he totally would. After trying his brother two more times, Dean decided it would be better to just get a room of your own, and you were much happier with that decision.

You watched as he unlocked the door, pushing it open and stepping aside, gesturing for you to go ahead.

“Ladies first.”

“You mean you’re not gonna carry me over the threshold?” you joked. “Thought you wanted to make this special .”

He gave you an unamused look, and you shot back a sarcastic closed-mouth smile before you were being swept off of your feet and over his shoulder faster than you could process.

“Dean!” you squealed, as he carried you through the doorway, kicking the door shut behind him before practically throwing you onto the bed.

He was hovering over you seconds later, his face a few inches from yours, and the mood shifted from playful to serious.

“Are you sure you want to do this?” he asked.

You nodded, your fingers coming up to play with the collar of his flannel.

“If I tell you something, you promise you won’t make fun of me?” you questioned, your eyes glued to the plaid pattern on his shirt.

“Promise.”

“I was kinda… holding out for you.” You drew your eyes up to meet his.

“Seriously?” he asked, half laughing. You could tell it wasn’t because he thought it was funny. It was because he couldn’t believe it.

You swallowed nervously, nodding again as you stared into those green eyes, and you hoped that this meant as much to him as it did to you. Something told you it did.

“I wasn’t kidding, you know,” he said.

You tilted your head in question.

“About making it special for you. I know it’s like, the grossest thing I could have possibly said but, you deserve so much better than me, and so if —”

“There’s no one better for me, you idiot.” And you almost told him everything. That you’ve been in love with him ever since you met one summer at Bobby’s, back when you were just kids. That everything felt like it led up to this moment. That you wanted him to fuck you and make love to you all at once. That you didn’t want this to be the only time he did. But instead, you grabbed his face in your hands and pulled him towards you, your lips meeting in a kiss that felt like it could have powered an entire country’s electric grid.

He deepened it, and the two of you were nothing but tongues and teeth and lips — it wasn’t sexy. It was hungry. Starved, more like. Like he had been thinking about kissing you just as long as you had been thinking about him.

You wrapped your legs around his waist, pulling his hips down towards your denim-covered core, down until you felt the hardness underneath his jeans pressed up against the spot where you needed him most, down until you couldn’t help but grind against it. He moaned as he kissed you, so you did it again. And again. And again. And —

“You need to stop that.” It wasn’t a suggestion. It was a command. You noticed that your arms were above your head, his hands pinning your wrists against the mattress. You don’t know when that happened, but you weren’t complaining. In fact, it spurred you on.

You smiled mischievously and rutted against him once more.

“What’re you gonna do about it, Winchester?”

He dropped his forehead to yours, steadying his breaths.

“I can fuck you like it’s your first time, or I can fuck you how I actually want to.”

“And how’s that?”

He took a shaky breath, like he was actually having a hard time controlling himself. You felt a sense of pride shoot through you at that.

“Like the fucking brat you are.”

You almost came from that alone.

Wanna know some common misconceptions about virgins? That they don’t have kinks. That they don’t watch porn. That they don’t have a plethora of sex toys in their nightstand. That they sit and crochet in their convent dorm room all day. Sure, you were years past the age when girls typically lose their virginity, but you were no saint. In fact, you enjoyed being quite the opposite. And you enjoyed being put in your place.

“Do your worst.”

It was like something in him snapped. His eyes were lust-blown and hungry and you didn’t miss the way his jaw ticked, and then he was undressing you so fast that you could’ve been part of a quick change act. He muttered something about a light system as he took off your clothes, and you nodded in a way that let him know that you already knew how all of that worked.

When you were down to just a black lace bra and panties, he paused as his fingers hooked under your waistband. He stared at you, his expression serious, and you knew that he was going to give you one more warning. One more opportunity to say, “Actually, I’d like to have a totally normal, non-kinky, first time experience, please.” But that wasn’t what you wanted.

“You sure you know what you’re asking for?”

You rolled your eyes. “I trust you. Put me in my goddamn place, Winchester. You’ve only been wanting to do it for the past two hours.”

“Oh, I’ve been waiting to do it for a lot longer than that, sweetheart.”

“Really?” you asked, raising an eyebrow.

“Oh, yeah,” he replied, huffing a small laugh before pulling off your panties in one swift motion. His hands came to rest on your bare thighs as he locked his eyes with yours. “Any hard limits?”

You shook your head. “I trust you. I mean, like, don’t pee on me or —”

“Not gonna happen. But… most everything else?”

“Dean,” you began, looking at him pointedly, “I trust you. If it helps, I’ve used like, toys on myself before. And I don’t mean just a vibrator, I mean like… well, you get the gist.”

“So I don’t have to go easy on you, is what you’re saying?”

“Put me in my place,” you repeated.

“Alright,” he replied, his hands gripping the underside of your thighs as he roughly pushed them apart, “but just so we’re clear, that’s the last order you’ll be giving tonight.”

Your throat bobbed and you nodded. “Yes, Sir.”

You meant it as a joke, but it didn’t come out that way. No, the title came out in a way that made his jaw clench and his eyes darken and it stoked the fire raging in your core.

Dean didn’t waste any more time talking after that, his tongue moving through your folds seconds later, drawing gasps and soft moans from your lips. You arched into him, your hands in his hair, silently begging for more. It wasn’t the first time a man had gone down on you, but it was the first time it felt like this .

He pinned your hips down to the bed with one hand splayed over your abdomen and then his tongue was inside you and “eating you out” didn’t come close to describing his ministrations. He was devouring you like his life depended on it, like the sounds you were making were a goddamn Zeppelin song that he wasn’t anywhere near done listening to. And then he added a finger, and then another, and it didn’t matter how many times you had imagined him doing this while you had your own fingers inside you — nothing would have prepared you for how good the real thing felt.

“Oh — fuck,” you gasped, and he chuckled into your sex and you had to actively think about not coming on his face and ending this whole experience early.

“You’re close,” he observed, flicking his tongue over your clit as he continued to pump his fingers in and out, and it was so fucking hot how he just knew that. It was like he had been fucking you for years, the way he knew your body, your tells.

You nodded. “Mmhm,” you confirmed, unable to form words with the way the coil in your abdomen was tightening.

“Hold it,” he ordered.

Your eyes shot open, because it wasn’t the command you were expecting, and you tried to lift your head to shoot him a cold glare but you couldn’t. And he just kept pumping, flicking, licking, chuckling — fucking asshole.

“Mm — fuck — please!” you cried out.

“When you come tonight, it’s gonna be on my cock. So hold it.”

You didn’t think you could. You had played this game with yourself and your vibrator and your self-control was majorly lacking and God his mouth and fingers felt so fucking good and you were there, the coil wound so goddamn tight, it would take nothing for you to let it snap, and then —

He stopped.

He pulled his mouth away from your core, his fingers out of your pussy, and you were writhing underneath him, because you had been right there and you needed him to be touching you again right the fuck now.

You whined.

He spanked your pussy. Not hard or anything, just enough to see if it was okay with you, and fuck, was it.

“Stop whining,” he demanded. He positioned himself so he was hovering over you again, his face inches away from yours as he stared into your eyes. “Or I’ll give you something to whine about.”

You were curious as to what that something would be, but sensed that right now wouldn’t be the best time for that question. You nodded instead.

“Good girl.” He smiled when he said it, like he knew exactly what those two words would do to you.

You squirmed underneath him, it had been too long since he’d last touched you. Too long being thirty seconds at most, but still. It had felt like hours.

“Has anyone ever told you,” he began, dipping his head to place a soft kiss on your collarbone, “that you are very,” another kiss to the other side, “very,” one more to the middle of your chest, “impatient?” He slowly pulled down the left cup of your bra, your breast spilling out of it. “Makes me wanna take my time.”

His eyes stayed glued to yours as his head moved down to your hardened nipple, taking it into his mouth at a goddamn snail’s pace. You arched your back, and he let you this time, chuckling at how easy it was to make your body react. His other hand slipped underneath you, unclasping your bra in a way that reminded you that he had a lot of experience doing so, and you refused to water the seed of jealousy that had sprouted from the thought. It didn’t matter that he had done this a million times. All that mattered was that he was doing it now, with you.

He pulled your bra off and threw it haphazardly over his shoulder, and you were suddenly very aware of the fact that you were completely naked, and he still had 87 fucking layers on, the outermost of which was still speckled with dragon blood, and it’s not that you were anywhere near clean, but you certainly didn’t want those clothes touching your bare skin.

“Dean?” you rasped, and he pulled away from your nipple to give you his full attention.

“You okay, sweetheart? Do you want to st—”

“No! God, no. It’s just —” you sighed, exasperated. This was dumb. You were going to stop him for this? Your eyes landed on a spot of blood on the shoulder of his flannel. Yes, yes you were, because that’s gross. “It’s just that your clothes are covered in monster blood and I’m like, totally naked, and I don’t want —”

He chuckled like you were the most adorable thing he’d ever seen. “I gotchya, baby.”

Baby. Baby ? You tried not to overthink the pet name as he climbed off the bed to take his clothes off, watching you the entire time. Sweetheart, you’d been called a million times. He called everyone sweetheart. But baby? Baby was his car, and no one else. Unless, that’s what you were to him now. His, and no one else’s. You filed the thought away under “Things to Think About After You Lost Your Virginity to Dean Winchester”.

He was in nothing but his boxers now, his cock already hard underneath them, and you bit your lip as he hooked his thumbs under the waistband and slid them off. And then, there he was, exactly like you’d imagined him but also better, because this was real and happening. You gaped at him, at his size. He wasn’t any bigger than the fake one you had in your nightstand, but that one was nine inches and you could never fit it all the way in. He was perfect. All of him.

“You okay?” he asked again, crawling back onto the bed.

“Mhm,” you managed, gulping.

He was on top of you again, his forearm holding up his weight as his free hand came to grab your thigh, hooking it over his hip and leaning down to kiss you. You could feel him against your core, his cock moving between your folds as he moved his hips, teasing you with it.

“Dean,” you breathed.

“Hm?”

“I want…” you couldn’t find it in yourself to finish your request.

“I know, sweetheart,” he whispered.

You decided you liked “baby” better.

“Please.”

“I thought you wanted me to put you in your place?”

You shook your head. “N-next time. Just, please .”

His eyebrows shot up, and you realized what you had said.

“Next time, huh?” he asked, with that shit-eating grin of his.

You rolled your eyes. He stopped moving, the smile wiped off his lips as he gripped you underneath your chin, somewhere between rough and gentle, the look on his face telling you he wasn’t messing around.

“Roll your eyes at me again, and next time I’ll really do my worst.”

You bit back a smile, and you just knew he was thinking, Brat. But you asked your question anyway.

“But not this time?” There was a devilish gleam in your eyes. You were tempting him, and he knew it.

“Do you ever get tired of being such a brat?”

“Dunno,” you shrugged. “Do you ever get tired of it?”

His jaw tensed, and he forced a sardonic, closed-lip smile. “Nothing I can’t handle.”

“Hm. But not this time, right?”

“Y/N —” he warned.

“Afraid you’re gonna hurt me? Scare me? What’s really keeping you from putting me in my place… Sir?”

For the second time that night, something in him snapped. You yelped as he flipped you over and grabbed your hips, dragging them upwards so your ass was in the air and your chest was on the mattress. Four hits to your cheeks came down in quick succession, and when you reached your hand behind you to block them, it was quickly pinned to the small of your back. Three more hits followed, accompanied by a pathetic, “Ow!” from your lips.

“Color?” he questioned roughly.

“So fucking green,” you replied, dazed.

Seven more hits followed, each one harder than the last, and you didn’t think there was anything better than the sting you were feeling right now. There was nothing more you wanted than for him to mark you up like this.

“Fuck, you’re dripping,” he commented. Five more hits.

“Oh, fuck!” you cried out at the last hit, one that felt like it reverberated through your entire body. One that definitely left a handprint behind.

“Yeah, but you like it, don’t you?” It was a rhetorical question. He spanked you four more times. “You just wanted me to mark you up, is that it? Think of me every time you sit down for the next few days, hm?” Three more.

“Mmph!” Your cries were muffled by the comforter.

“Yeah, I can tell. Look at this fucking mess.” He dragged his fingers through your soaked folds. “Jesus Christ,” he said under his breath, and then he was flipping you back over. He nestled himself between your legs, his tip teasing your entrance. His expression softened as he stared into your eyes. “Are you sure?”

You nodded. “Yeah,” you replied breathily.

He slid into you slow and easy, your mouth open in a silent moan as he bottomed out.

“Good?” he asked.

“So fucking good.”

When he started to move, you thought you were going to die. In a good way. In a way that made you decide right there and then that when the time did come, this was how you wanted to go out.

“Harder,” you encouraged, and he obliged. “Faster.”

He was properly fucking you now. Hard and fast and dirty. Your legs were wrapped around his waist, your heels digging into his ass, forcing him to go deeper. His head was buried in your neck, your nails were clawing up his back, and the room was filled with moans and pants and expletives that put a sailor’s mouth to shame.

“Shit, baby,” he panted into your neck. “God damn, you feel good. So fucking tight.” He sped up his thrusts, and the bed was squeaking so much that you thought it was going to fall apart underneath you, but you were too far gone to care. He reached a hand down in between your bodies, his fingers finding your clit, circling it expertly. You were on the precipice of your release in seconds. And then —

“Come. Soak that fucking cock, baby. Come for me.”

And you screamed loud enough to get both you and him kicked out of the motel if they cared enough as your orgasm ripped through you. He fucked you through it, his pace only faltering moments later, right before he pulled out and painted your stomach white. It looked like a Jackson Pollock on your abdomen. Kinda hot, actually.

“You okay?” Dean asked, looking down at you as he finally caught his breath.

“More than,” you smiled.

He mirrored the look on your face before crawling off the bed and heading to the bathroom. He came back moments later with a damp washcloth, gently cleaning his masterpiece off of your skin. When he was done, he threw it across the room, aiming for the bathroom, and it landed on the tile in front of the toilet. He laid down next to you, pulling you into his chest as he pressed a soft kiss into your hair, and you wanted to ask so many questions, all at once. What were you two now? How long had he been wanting this? Would there be a next time? Instead, you opted for —

“You know in fanfictions, they write you as a submissive most of the time.”

He snorted. “They’re half right.”

“A switch?” you asked, surprised. “Lucky me.”

He chuckled softly. “Sorry about your ass.”

You shrugged. “I was asking for it.”

“Oh, you were definitely asking for it. Still, I… I dunno. It was your first time, I didn’t want to get too —”

“It was perfect, Dean.”

“Yeah?”

You nodded, smiling, dozing off already. “Yeah.”

#dean winchester x reader #dean winchester fanfiction #dean winchester smut

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