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You tell yourself, over and over again, that this is going to be the last time. It’s not something that’s meant to be held onto, so you can just… let go.
But then you find yourself here. Between tangled sheets with your legs spread wide, your nails digging into Dean’s bicep and his cock dragging through your wet, sensitive cunt.
“There you go,” he coos in your ear, every thrust deep and rough. “That’s my girl, takin’ me so good, so- Good-“
Dean moans, pressing up against the soft, gummy spot inside of you, and your eyes roll back in your head.
He always does this. He knocks on your door and grabs your face between big hands, and suddenly all that resolve and determination—never again—dissolves with your willpower. His hands are rough and calloused, but trace your hips and hold you down so gently, you can almost pretend he cares if you break. His cock is thick and impossibly long, and he always drags it between your soaked heat and bumps it against your clit before pushing himself in just right. His lips are chapped and soft, sucking possessive marks into your neck that he has no right to claim, but that doesn’t stop you from running your fingers through his hair and holding him right where he is. He wouldn’t dare to leave. Not in the middle of this. Not before you’ve both gotten what you want.
What Dean wants. You don’t let yourself pretend that this is everything you need anymore. It’s the only hope you have of one day telling him no, because the rest of you control rests on a thin rope, and it always slips from your hands the moment Dean touches you like you matter.
You never walk away from him with an aching, unsatisfied body. A few nights ago he put you on his face and made you ride until your thighs were shaking and tears were springing into your eyes. Before this, he spit on your cunt and scissored you open with thick, careful finger, kissing and nipping at your thighs as your greedy pussy swallowed him right up to the knuckle. Even now, as every roll of his hips becomes smaller—as his face twists in concentration and his mouth against your jaw becomes desperate—Dean’s thumbing at your clit, trying to get you over the edge with him.
“C’mon, baby, c’mon-“ He pushes himself up to his knees, forcing a deeper, rougher angle. “Show me what you’ve got, I know you can do it, come on-
You whimper, staring up at him under lidded, glazed eyes. The whole world is just a blur of color at this point, but Dean is bright and clear. The heave of his broad shoulder and chest, every muscle in his arm as he wraps it around your waist and makes you arch your back, the flex of his abdomen as he ruts forward like a feral dog. The sharp, unforgiving thrusts are making your head spin with pleasure, turning you into a boneless wreck of need. You grab his arm, trying to steady yourself against something, and Dean’s attention rips up.
He says he likes to watch himself fuck you, and you’ve never doubted that for a second. He’s spent whole sessions just staring at his cock or fingers splitting your cunt open. He likes putting you on his face because he can watch you react. You like it better like that, usually. The eye contact is too close. Too intimate. Too real.
But you grab him, and he looks at you, and it’s almost like a shot. His eyes are blown-out and so strangely soft, staring at your wrecked, open expression with too much, too much, too much-
“De- Deeean-“ You cry it out like a pray, because it is. Dean grunts, hips snapping, the wet sound filling up the air and his eyes never leaving yours. “Dean- Dean- Fuck, please- Please-“
You’re babbling. You never do that with anyone else, but Dean is Dean, and he makes you do things you never counted yourself capable of. He groans your name, and you squeal when he drags you up, off the mattress and straddling his thighs. Your clit drags against his abdomen, his cock bullies right against your g-spot, and Dean grabs your jaw with a single, painfully gentle hand.
“Cum for me, sweet girl,” he rasps, still holding your gaze, even as your eyes start to cross. “Soak this fuckin’ cock, baby, cum-“
You almost scream as your orgasm rips through you, and Dean crashes his mouth against yours, eating every whimper and moan with harsh lips and his tongue down your throat. You press into him, pussy gushing and fluttering around his dick, and he makes that deep, rumbling sound that always comes right before-
“Shit-“ Dean gasps against your mouth, pulling you so close you can’t feel anything but the heat of his bare chest, the sensation of his cock twitching and pumping in your cunt. “Fuuck-“
Dean moans your name, and a warm, pleasant heat starts to spread through your tummy and drip between your thighs. He doesn’t stop moving until his cock is softened, and you don’t try to stop him. You’re barely more than a limp doll right now, returning his kisses with tiny mewls, eyes crossed and body limp.
For a moment after it’s done, you stay tangled together. You always do. It’s the most dangerous part of the whole thing, because it feeds that tiny little fool in your chest, who refuses to believe that this is just sex. Who takes your heartstrings and weaves grand worlds where Dean loves you back, and you’re going to be just fine.
Dean kisses your brow, and your eyes flutter closed. There’s an advantage, to being a crybaby whenever he fucks you stupid. He never once has considered that the tears might be real.
“Think you can walk?” He mutters, still buried deep inside of you, still holding you like he cares.
You shake your head, and his mouth twitches against yours.
“Alright, pretty girl. I’ve got you.”
And you press your face into the crook of his neck, letting that fool take you over. She takes his words as gospel. My girl and I’ve got you and Baby, they’re exactly what he means and nothing more, nothing less.
When the logical part of your brain wakes back up—Dean’s always had this ability to hit a button in you, sliding his hand around the back of your neck and making all your thoughts just bubblegum feelings and electric colors—you’re going to remember why you always say this has to be the last time.
He’s perfect, and he’s not yours. He makes that perfectly clear, until he pulls these little stunts and ends up buried between your thighs. You agreed that he wasn’t yours, when this arrangement started.
Safer with someone you know, he’d told you, like he hasn’t fucked his way across the entire country. Easier. Nothing to worry about, when it’s you and me.
And you’d been a starry-eyed, gooey hearted fool who just wanted whatever part of Dean he was willing to show you. The burning love you kept tended in your ribs hadn’t seen a problem with adding fuel to the wildfire, even if Dean was never going to see it. But now he’s carrying you to the bathroom like a princess, and he’s going to be gone in the morning, and that wildfire is an inferno. He doesn’t know. He can’t know. You can map out everything he’d ever say in response to your feelings, from the harsh sneer he would’ve given when he had the Mark of Cain, to the kinder let down you’d get now.
You’re too young, he’d say, like it was a consolation prize. And I like you, sweetheart, but I don’t do this kinda thing. Not with girls young enough to be my daughter. Not with kids that I hunt with. Not with you.
You press your face further into his neck. He’s always so warm and sturdy, a massive tree that’s offering you just as much shade crushing, unbearable weight and tangled roots that keep you pressed down. He smells like leather and whiskey and something perfectly, faintly spice. You want to drown in it. You want to drown in him.
“You good?” Dean asks, and his voice is too gentle. It rattles the little fool, screaming for the rest of you to listen and just accept that he loves you.
But he doesn’t. He doesn’t.
“You’re bein’ quiet, even for- Y’know-“ He chuckles, that low, insufferably charming pride crawling into his voice. “After I fuck you dumb.”
“You did not fuck me dumb,” you mumble against his skin, and you can hear his grin.
“Big words from the girl who couldn’t talk five minutes ago.”
“That was unrelated.”
“Unrelated,” he echoes, his thumb dragging a small circle against your spine. “Always forget how bratty you get after, sweetheart. Dangerous.”
You roll your eyes, and hug him tighter. He laughs, and kisses the side of your head, and he has the nerve to call you dangerous.
“You wanna watch a movie?” He asks, leaning down to run the water, still keeping you tucked so carefully against his chest, and all you can do is nod. Dean sighs. “C’mon, gimme a little more than that-“
“Yes, please,” you mumble, and he pauses.
It’s only a fraction of a second. You don’t understand it, and you don’t want to. Not when he feeds your delusions and kisses your brow again, then your cheek, then your lips. And you let him. You always let him, because you’re a foolish, stupid, lovesick idiot. You don’t want his affection, not like this. But you don’t want to lose him—it would be like ripping a vital organ out of your ribcage, even if you didn’t know you had it a year ago—and you can’t ever tell him to stop being so sweet without explaining yourself, and getting that gentle, horrible let down.
You don’t want it. You don’t want any of it. And this, this had to be the last time.
You hold the line. You don’t know how, but you hold that line with white knuckles and grit teeth and a taste like bile in the back of your throat.
Dean knocks on the door, only two nights later, and you don’t answer. He calls your name and you sink into the mattress, praying he just thinks you’re asleep.
“I just- Uh- I wanted to talk?” He says, and you press your face into the pillow like that can somehow shield you. “Really, that’s it. Just talking, so- If you could-“
Dean sighs. You can hear the please, hanging between every word, but Dean doesn’t really say please. He just begs with everything else in him, or gives up. And you can picture him running his hand over his face, the heavy look in his eyes, the defeated sag in his shoulders. It’s like a knife being driven through your gut, and you sit up, ready to open the door-
“Alright,” he mutters, and you freeze. “Night, baby. Sleep well.”
Footsteps retreat, and you stay there on the mattress, frozen and lost, adrift in a sea you dove into.
But you did it. You held the line.
And you keep it. It makes sweat bead and your skin burn, but you close the door and don’t open it back up. You’re done, and you’re going to keep it that way.
Dean doesn’t ask questions. You don’t know if you want him to or not, but it doesn’t matter, because you catch him staring and giving out signals, but he’s taken your no in stride, and doesn’t seem to have any plans to push back against it. When this started, you agreed to leave out a specific book on the war room table if either of you wanted something. Dean starts to leave it out every night, and you never go to his door, and one night, it vanishes.
And that’s fine. That’s exactly what you wanted.
And if it feels like you’re dying because of it, and if you spend an hour over the toilet dry heaving that night, that’s no one’s business but your own.
“Dean’s been grumpy lately,” Sam says one morning, and you blink at him over your coffee.
“Grumpy? Dean? That’s- Woah-“
“Yeah, yeah, okay.” Sam gives you a flat look. “You know what I mean. Grumpier.”
You shrug, looking back to your mug. “Maybe he needs to get laid.”
“Uh huh.”
You can feel Sam’s stare. It makes you itchy and small, and you’re not sure if you want to punch him or run. You settle for staring at your coffee harder. It’s the easiest course of action.
“Dean needs to get laid,” Sam repeats your words, something strange—almost sharp—in his tone, and you nod.
“That’s what I said.”
“Dean-“
“What’s up?” Dean walks into the kitchen, stopping right behind you, and you hunch over like you can grow a shell to protect yourself.
Even just a few feet away, he’s always so warm.
“Uh- Hey, Dean-“
“Hey,” Dean mocks back, and Sam huffs.
“Dude-“
“Shut your face-“
“I didn’t say anything- I-“ Sam says your name, and you glance up. His brow is furrowed with worry, his eyes locked on Dean behind you. “We were just-“
“Just what?” Dean snaps. “Just talking? Shooting the shit, getting real comfortable?”
Sam sighs. “Dean-“
“I got a gun, Sammy,” Dean points firmly, and you stare at his finger like a woman driven mad with thirst. “Don’t forget that.”
Sam rolls his eyes. “We all have guns, that- That threat doesn’t do anything-“
“I’ll show you doing something- Hey-“
Dean says your name, and you freeze. You’d been trying to slip out while they fought, but Dean—goddamn him—had noticed. He always notices. You love him so much it’s going to make you cave in on yourself, and maybe take the whole bunker with you, like a dying star.
He catches your arm, and you can’t stop yourself from looking at him. His brow is knit, his jaw locked, and his handsome face has deep lines you only used to see when the world was ending. There are bags under his eyes. Deeper than usual. You want to smooth the lines with your thumb and kiss his jaw until he relaxes, but that’s not your ache to soothe.
Dean doesn’t say anything. You can’t say anything. He looks exhausted, and there’s a lump forming in your throat.
“You- You hungry?” Dean rasps, and you’re starving.
“No,” you breathe before you can think, and Dean swallows.
“Well, when you’re hungry- There’s a diner in town-“
“Henry’s?”
“No, uh- A new one. I- I was wonderin’ if you wanted to go, later, or something.”
“Or something?” You tilt your head, and Dean nods.
“Whatever you want.”
God, he’s cruel. He’s perfect and cruel, and you want to vomit on his flannel and kiss him until you pass out.
“Oh- Okay,” you say, because you’re only so strong.
The lines in Dean’s face relax. His grip loosens. Then Sam coughs, and Dean lets you go.
The diner is… nice. Nice and easy, in a way you haven’t felt in longer than you want to admit. Dean insists on driving you, and paying, and sitting in one of those booths with your feet bumping under the table.
He presses his knee forward, while he orders. You swallow and don’t allow yourself to think much of it. He’s warm through his jeans, but he’s always warm, and he hasn’t tried anything in a few weeks, so you allow it. Your love for him hasn’t been flickering out, but the harsh wind of his absence has made everything feel colder. It’s okay, to indulge yourself in something so small. You’re still keeping it together. You’re still holding the line.
“So, uh-“ Dean clears his throat, turning his bottle in his hands. “How are you?”
“How- Am I?” You blink at him, and he nods tightly. “I- I’m okay. How are you?”
“Good. Great.” He frowns at the table. “You know. Same as always.”
You almost laugh. “You’re always great?”
“I focus on the positives, sweetheart-“
“No, you don’t.”
He rolls his eyes, glancing up to hold your light, amused gaze. His mouth twitches. His fingers tap against the glass, and you try not to let yourself sink too deep into the attention.
It’s okay to drown a little. A long as you don’t drop the line.
“Maybe I’m turning a new leaf,” he says, and your face splits into a full smile.
“You?”
“Yeah, me. Why’d you say it like that-“
“Because you’ve never turned a leaf in your life-“
“Ah-“ He points the head of his bottle at you with a grin. “Not true. Remember when I started learning guitar?”
“Yeah, you smashed it on a werewolf’s head after a month.”
“That was a tactical choice, I would’ve kept playing if the wolf didn’t get in the way.”
“Uh huh.” You lean back in your seat, crossing your arms. “What songs had you learned to play?”
Dean’s nose wrinkles. “Hey, we don’t need to talk about that-“
“I think we do.”
“Nah, I mean- I only had a month-“
“You learned how to work a rocket launcher in a week.”
“That’s just buttons and triggers, sweetheart. Even you could work it.”
“Even I?” You raise your brows—trying not to let the delight shine too bright in your voice—and Dean freezes.
“I mean- uh- You’re not great with guns, and- I could teach you-“
“You could teach me.”
“Maybe? If you wanted- Or-“ Dean groans, slumping back. “Stop givin’ me that look.”
“I’m not giving you any look,” you tease, and Dean sighs.
“Will you stop if I say I’m an idiot?”
You soften slightly. “You’re not an idiot, Dean-“
“You sure?” He grumbles. “Kinda feeling like one right now.”
You laugh, but it’s gentle. You can almost see him pushing down into himself. It makes you heavy for him, like you’re trying to take that invisible weight off his shoulders, even if he can’t feel you helping the pain. “You’re a dork,” you say, bumping his knee under the table. “But you’re not an idiot.”
Dean grunts, watching you under hooded eyes, and you smile easily.
You missed this, more than you want to tell him. Just talking, without worrying that it’s going to end in world-changing, back-breaking, beautifully heart-aching sex. He feels like your friend again, closer to your fingertips than he’d been when he was balls deep inside of you.
“Wonderwall,” he grunts suddenly. “And Hallelujah.”
You blink. “What?”
“Those were the songs,” he mutters, picking at the label of his bottle. “That I got, before I smashed the guitar.”
“Oh,” you pause. “I love Hallelujah.”
“Yeah. I know.”
You stare at him, and he stares right back. A faint flush is threatening your cheeks, so you duck your head to hide it, and Dean lets out a soft laugh.
“You alright-“
“Yep. I- I’m good-“
“You look good.” Dean laughs again, when you shoot him a glare. “Don’t gimme that face, I’m saying something nice-“
“You’re being a butt,” you stick out your tongue, and his eyes dance with an easy kind of light that almost makes your heart stop.
“You’re the one who was callin’ me old earlier,” he drawls, and you roll your eyes.
“You are old.”
“Yeah, but that’s never stopped you, has it.”
Your mouth falls open, eyes going so wide it almost hurts, and Dean grins at you. If you weren’t shocked into static, you’d slap him or- or lunge across the table and kiss him-
Hold the line.
“Aged wine is supposed to be better,” you manage to say, somehow, and Dean laughs, loud and free.
“That all I am to you? Some wine?”
“No,” you smile at your plate. “You’re also very good cheese.”
“Good cheese, huh.”
“Mhm.” You point a stern finger at him. “No puns.”
Dean rolls his eyes, but dips his head. “Yes, ma’am.”
There’s the flush. You’d keep trying to hide it, if Dean didn’t start talking about something unimportant and easy, and suddenly you forgot to be embarrassed. He’s not trying to kiss you or get you back to the car. He’s just… Talking to you. Dropping that light, teasing praise like it’s nothing, then telling you a story about when he used a tuba to beat a poltergeist, grinning like a winner every time you laugh.
When lunch is over, he rests a hand lightly on your lower back, but doesn’t do much more. He kisses your cheek when you get back to the bunker, and asks if you want to watch a movie tomorrow night. You swallow, locking your hands together like they can force the line to stay firm. Dean says your name, almost panicked, and you blink up at him.
“Just a movie,” he says, rubbing the back of his neck. “Out in town, at- Uh- That shitty theatre next to the coffee place. Or- I can try and find a drive-in, if those still exist-“
“They do,” you say softly, and he swallows. “There’s one out in Beloit.”
“Beloit,” Dean mutters. “Yeah- Yeah, okay. You wanna go there?”
You nod, and he grins. You smile back, and it feels… Different. Shy, in a way you haven’t been around him since he first started fucking you. Almost delicate. You weren’t supposed to let this feel like something delicate.
Dean jaw works, and you can almost see the thoughts turning behind his eyes. He lurches slightly, brow furrowed, then pulls back up. You’re seconds from asking him what’s wrong when he just leans down and… does it.
His lips graze your cheek, his hand brushing against your waist, and you almost melt right into him.
But then he stands back up, and takes a large step away. You swallow, resisting the urge to reach up and brush your fingers over where he kissed. It’s not like he’s never done that before, but again.
It just feels different.
“See you tomorrow,” he murmurs, and you nod weakly.
If you had a mind that was thinking in more than bursts of glee and songs of Dean, Dean, Dean, you’d tell him that you live together, and he’s always going to see you tomorrow. But he walks away, and you let him, and it doesn’t hurt. There’s a space that he left, but something in you seems to think he’s going to come back. You can’t tell if it’s the fool or not.
For once, you decide not to try.
The movie is nice. Dean rests his hand on your knee, but doesn’t go any higher. You lean into his side, and his arm goes around your shoulders, but there’s no kissing or dragging into the back seat, and you didn’t know there could be a better way to be close to him. Sex is great. Looking up and finding him already watching you is better.
He brushes some hair from your face, and you half expect him to kiss you. His eyes dart down to your lips like he wants to. Your fingers curl in his shirt, and his throat bobs.
“You likin’ the movie?” He whispers, and you nod.
“Good find,” you breathe, and he grins.
“Thanks. Eat the popcorn, it cost me a billion bucks.”
You roll your eyes, and throw some of the over-buttered, half-burnt popcorn at his face. He laughs, catches a kernel in his mouth, and grabs your chin between two fingers. Your breath catches. He just turns your face back to the screen, and pulls you a little closer into his side.
The movie ends the same way the diner did. Dean walks you to your bedroom door like it’s the porch of your house, kisses your cheek, then walks away.
Then, after the movie, you play mini golf. You win, but you know he let you. He buys you a snow cone and licks it off his nose when he eats it like a rabid dog. You wipe a little extra off his cheek, and he stares at you, but still doesn’t kiss you. Not fully. His hand seems to always rest on your lower back, now, but that’s all the contact you get. All that you allow.
Hugs are on the table, too. They’re somehow more dangerous than the forehead kisses. After the hugs, he sometimes just stares at you and cups your cheek, and your heart moves into your throat until you think you’re going to spill it out all over his chest.
You manage to keep it together. For the sake of this new, slowly growing garden of what your friendship is becoming, you swallow your love with greater ease and more bile than you ever did while you were fucking. After the mini golf you get dinner and see another movie. You convince him to go on a walk with you, and he hates it less than he pretends to. You eat together in the bunker and call when he’s on a hunt with Sam and go to a car show and it all feels like breathing.
Sometimes he still looks at your mouth, and you freeze up, unsure if you want him to kiss you or not. You know you want him, but somehow you’ve found even more to lose than before, and if it slips through your fingers, you’re not sure they’re ever going to stop shaking and groping at the empty spaces again. You can take holding his hand in the bookstore while he peers over your shoulder, pretending to be interested for no real reason other than to make you smile.
“There are so many of them,” he mutters, and you giggle.
“There’s a lot of ways to write words, Dean.”
“Yeah, but- You’d think there would be repeats or something.”
“There probably are,” you shrug, running your fingers over the spines. “But they’re still all fun.”
Dean sighs, squeezing your upper arm. “Whatever you say, sweetheart.”
You hum, leaning back to smile at him, and all his features relax.
“You want some coffee?” He brushes some hair from your face and you nod.
“There’s a shop next door, could you get me-“
“Hey,” Dean flicks your nose, grinning roguishly. “Trust me, I know what you want.”
You nod a little stupidly, and his smile falters. He looks to your lips again, then almost shakes himself, taking a small step.
“Don’t move,” he squeezes your arm again, then backs away. You watch him go, unable to help yourself, and smile when he looks back. He does that all the time now. And he always smiles back.
You turn back to the shelf, looking at the books without actually looking. You already miss him, and he told you not to move, but that can’t count if you’re going to stand next to him in the coffee line, can it-
“Hey.”
You fumble slightly, turning to find a man leaning against the shelf and smirking at you. You blink, and his smirk widens.
“What’s girl like you doin’ in a place like this?”
“The… Bookstore?” You frown, and he laughs. You don’t think you said anything all that funny.
“Look, I just- I saw you from over there,” he nods vaguely, and you frown. “And I thought you were cute. Can I get you some coffee or something?”
“My- My friend is already getting me coffee,” you say, and your voice sounds strangely far away.
The man nods, but doesn’t retreat. “Alright, then can I get your number? Maybe beat your friend to coffee next time?”
And you don’t want to say yes, but this is a chance. To hold onto this new friendship with Dean while also getting over him at the same time. This man isn’t ugly. Compared to Dean, no one really stands a chance anyway, and you have to get over him eventually.
So you give him your number, and try not to feel like you just did something wrong.
Dean clears his throat from behind you, and you spin around on your heels, a sour guilt twisting in your gut.
“You- You’re back,” you say, and he grunts.
He’s not look at you. He’s glaring at the man with the same, deadly glint that he gives monsters and demons before he cuts them in half. You touch his arm lightly, and he tenses. You feel sick.
“Hey, buddy,” he snaps at the man, who—not seeming to understand the gravity of Dean’s glare—grins back.
“Hey.” He winks at you, slowly backing away. “Have fun with your friend.”
Dean’s coffee spills over the top of it’s lid. He doesn’t look away from the man when he leaves the store. He shoves your drink into your hand, not meeting your gaze.
“Dean-“
“I’m gonna go wait in the car,” he mutters, and you swallow.
“Oh- Okay.”
Your arm wraps around your stomach, and you press a little away from him, from the wrath seeming to wave off his body like a volcano. He glances down, jaw tight and a vein in his brow ticking. You stare at his neck, unable to hold the weight of his gaze. He lets out a sharp breath, and shakes his head.
“Get your book.”
You shake you head. “No- It- It’s okay-“
Dean says your name, and your mouth snaps shut. “Just- Get the damn book.”
He looks like he’s in pain, and you don’t know how to fix it, so you do as he says. You get a cheap one, that worm of guilt burrowing deeper and deeper into your gut until you can’t even drink your coffee without feeling like it’s going to come back up.
Dean’s fingers dig into your back, when he guides you out the door. He starts the engine by almost punching in the keys, and holds Baby’s wheel like he’s trying to strangle it. You can see all the anger brimming under the surface of his skin, and worried you’re just going to make it worse. You don’t even know where it came from. It’s not like you’re together, or the guy said something rude. You open and close your mouth too many times to count, then give up, shrinking back into your seat.
Dean looks over at you. You try to look out the window, and nowhere else.
A loud, sharp breath escapes him. “Son of a- Alright.”
You look over with a frown, then squeak when he yanks the wheel off to the side.
“Shit- Dean-“
“Just- Fuck-“ He bows he head, glaring down at his legs, and you swallow.
You fidget with your fingers, watching him nervously, waiting for him to break the silence. It takes while. So long you think about just getting out of the car to give him space.
But then he looks up, and your heart gets cleaved open. His face is twisted in pain, his lips parted and his voice quieter than you’ve ever heard.
“What-“ He takes a deep breath, scanning over your openly confused features. “What else am I supposed to be doin’?”
You blink at him, fingers curling in your lap. “What?” You ask softly, and his throat bobs.
“I- I’m really trying,” he mutters, looking back to his hands. “I swear to god, baby, I’m tryin’ my best, and- I know I ain’t amazing at this but- If you could throw a guy a rope when he’s never- I’ve never done this, alright.” He waves between your bodies, jaw clenched tight. “And I’m really givin’ it my best shot, but I’m still not allowed to kiss you, and you’re takin’ numbers right- Right in front of me- So just- Something.” He gives you a pleading, broken look, eyes shining on yours in the dark. “Anything.”
You open your mouth, but you can’t even figure out what the fuck you’re supposed to say. You know all the words he’s saying, but it’s like he’s speaking a language you never learned, spitting out a code you’re just supposed to magically understand. Dean’s jaw ticks, when you don’t answer, and you try to sputter out an answer, but he’s too loud to hear your confused whimper.
“Look, just- Whatever the hell you do need me to do, I’ll do it, I swear I’ll do it, but- You gotta tell me, sweetheart-“
“Tell you what?!” You almost shout, and Dean leans back in surprise. “Dean, I- I don’t know what you’re talking about.”
Dean huffs a low laugh, looking back out to the road. “Yeah. Alright,” he grabs the keys, voice rough and pained. “Sure. Whatever-“
“No.” You grab his wrist before he can start to the engine. “Tell me what you’re talking about.”
“It doesn’t matter-“
“Yes, it does-“
“Nah.”
“Dean-“
“You wanna call that guy, call ‘im.” There’s an almost toxically bitter sound to the words, and Dean’s making a face like he just got shot. “Whatever. See if I care.”
Your nails dig into his wrist, when he tries to yank it away. He shoots you a glare, the bags—gone, after months of ease—already starting to form.
“C’mon, kid, just- let go-“
“Would you care?”
Your question is small, but it makes Dean recoil like it burned. He scoffs, but it’s too loud, and you hold him tighter.
“Would you care-“
“No, I fuckin’ love watching douchebags parade around with my girl, who would care about something like that?”
Something snaps, right at the base of your spine. You sit so tall you’d think someone is dragging you by the nape of your neck, and Dean blinks in something close to surprise.
“What-“
“Your girl,” you whisper. “That’s- I’m- Why would you say that?”
Dean blinks. “Why wouldn’t I say that?”
“Because you and I- We’re not- That’s-“ You lean back, letting go of his wrist, and when you look down, you’ve left little crescent marks in the skin. “No- No- You didn’t- You said no- No strings-“
“Yeah, and then you stopped fuckin’ me, and I-“ Dean says your name as you press back against the window, brow furrowed in worry. “Baby, it’s- It’s alright, I’m not that pissed-“
“You were yelling,” you choke out, and he swallow.
“Well, I was- Just- C’mere.”
He reaches out, cupping your cheek with the same gentle touch he used to use, right before he kissed you. You gape at him, head spinning, panting like you just ran a marathon.
“I’m not mad,” he rasps, almost pleading, and you shake your head.
“You were-“
“Sweetheart-“
“Why?” You whisper, grabbing his wrist, your nails sinking back into the marks. “Why- Why would you care?”
Dean swallows. He shakes his head, looks out the window, and chuckles.
“Dean-“
“I don’t want you goin’ out with him. And- Call it possessive, or stupid man shit, or- Whatever the hell you want,” he drags his thumb over your cheekbone, voice dropping to something tender, something soft. “You’re my girl. And I want you here, telling me what to do, how to- To be what you need.” His voice cracks. “Come on, baby. Just- Tell me what to be.”
You stare at him, a lot of pieces colliding into each other at once in your head. The diner and the movie and the touching and the caution and-
“Are we dating?” You choke out, and Dean frowns.
“What’d you mean, are we dating?”
“I mean are we dating, Dean, are you- Are you my boyfriend?”
“Uh- Boyfriend kinda makes it sound like we’re sixteen and necking-“
“What the fuck is necking?”
Dean groans, dropping his head. “Don’t say that, sweetheart. Makes me feel fuckin’ fifty.”
Your lips twitch. “You are almost fifty,” you say, and he chuckles.
“Yeah. Guess I am.” He looks back up to you, caution lining his features. “You always seemed to like it.”
You swallow. You did. You’d never been sure if it was the older thing itself, or the fact that it was just Dean, but you’d liked it. You always liked all of him, from the uglier wounds to the beautiful, glowing heart that almost managed to peak through, no matter how thick his steel and iron walls became.
He glides his thumb back and forth over your cheekbone, and your breath hitches. He swallows, closes his eyes, and mutters your name.
“Did you… Not think we were dating?”
You shake your head, and Dean snorts dryly.
“Huh,” his mouth curves into a tight smirk. “Makes sense why you wouldn’t kiss me, I guess.”
“You guess?” You squeak, and Dean nods.
“Yeah, makes a lotta sense, actually-“
“How long have we been dating?!” You almost shriek, and he gives you an amused look.
“’Bout three months.”
“Three months?!”
“That’s what I said, baby-“
“Shut- Shut up-“ You plant a hand over his mouth, and he raises his brows. “Why the fuck wouldn’t you tell me we were dating, you- You butt?!”
Dean’s eyes sparkle, looking pointedly down to your hand, and you release him with a scowl. He rubs his jaw, grinning at you like you’re some cute bunny, and you lean back in your seat with a huff.
“Sweetheart,” he says gently. “I thought you knew.”
“How would I have known-“
“’Cause I asked you on a date? And you said yes?”
“That- That never happened.” You snap, and Dean frowns.
“Yes, it did. Sammy- He was there-“
“Sam was there-“
“Yeah, and- I said there was a new diner in town, and you said you’d go with me, and we started dating!”
You stare at him, mouth hanging open. Dean stares pointedly back, and you can’t help yourself. You bark out a loud, sharp laugh.
“That was not asking me on a date, you fucking- Oh my god!” You shake your head, and Dean’s frown becomes almost puppy like.
“Yes, it was-“
“You have to actually say it’s a date, Dean! You can’t just- Just ask me to do something, I thought we were just hanging out! As friends.”
He’s pouting now. If you weren’t pissed, it would be adorable. “I- Uh- I paid for everything. And got you gifts.”
“Friends do that-“
“Do friends kiss your face all the time?” Dean twists to fully glare at you, and you pause.
“Um- Maybe?”
Dean snorts. “No, they don’t-“
“But I thought that was just you!” You protest. “You- You’re always- You know-“
“I know?” He mocks, and you scowl.
“We were fucking for a year, Dean,” you snap, tipping up your chin. “I thought you were comfortable with me.”
“I am comfortable with you,” Dean shrugs, leaning slightly forward. “Real comfortable.”
Your nose twitches. He’s too close, now. Consuming your vision, making your vision all stupid and fuzzy. “You’re comfortable with everyone,” you sniff, and he laughs.
“Oh, sweetheart,” he drawls, running a hand slowly up your thigh. “We both know that ain’t true.”
You make a tiny, involuntary sound when his fingers dip under your skirt, teasing sensitive, neglected skin. He hasn’t touched you there in so long. Too long. You have to hug yourself to stop your body from flying at him.
“I haven’t fucked anyone else in eighteen damn months,” Dean mutters, holding your gaze. “I’ve been waiting around for you for months, wondering what the hell I was doin’ wrong, and you thought I was just being nice?!”
You swallow, your voice suddenly small. “You are nice,” you whisper, and Dean snorts.
“No, I’m not.”
“You’re nice to me-“
“Because I-“ He cuts himself off, fingers pressing into the soft skin of your thigh. You grab his hand, holding it against you, and his eyes dart down. He heaves a long breath, squeezes his eyes shut, and bows his head.
“Dean?” You whisper, and he shakes his head. “Dean, I- I’m sorry I didn’t- You said we were just going to be casual-“
“I know what I said,” he grunts, glaring at your hands. “But I- I didn’t- I thought it would help me.”
You swallow. “Help you?”
“Yeah.”
“With what-“
“You know what.” He finally looks at you, and you’ve never seen him this vulnerable. Almost bowing before you, holding onto your hand like it’s the last thing keeping him alive. “And I can’t- I don’t know how to-“ He takes another ragged breath, gives you another pleading look. “You stopped letting me pretend, you started- You started telling me no, and I couldn’t- I couldn’t.” He swallows. “I’m tryin’ to do this right, baby.” He squeezes your hand, leaning a little closer. “Please let me do this right.”
You blink at him, tears watering in your own eyes, and nod. Dean’s shoulders shudder, and he holds your hand so tight you think he’s trying to just mold you together. He glances at your lips, but doesn’t move. So you do it for him.
Dean stares at you, completely still as you lean forward, his chest so still you’re worried he’s not breathing. You rest your hand lightly on his chest and press the lightest kiss you can to his parted lips. He shakes, one hand flying to your waist, his touch still heartbreakingly delicate. You kiss him again, a little harder, and a low rumble starts in his chest.
You pull back, pressing your brows tight together. Dean stares at you, eyes glossy and blown out, the restraint ticking in his jaw, and you smile softly.
“I love you,” you breathe. “And I- I know you can’t- You know, say it back, but- I love you, Dean.”
His breathing his ragged, and he’s still gaping. You laugh nervously, looking down to your fingers, fiddling with the collar of his shirt.
“If- If you could say something, though, that would be- Um- Nice-“
Dean grunts, and your words fall off into a squeak as Dean drags you forward into his lap.
And this. This is a real kiss. Dean’s mouth slots perfectly against yours, his arm wrapping fully around your lower back, his fingers digging into your hips and his other hand cradling the back of your head. He kisses you like he’ll die if he doesn’t, pushing his tongue down your throat and moaning against your mouth. You pull on his shirt and he gropes at your ass, dragging you further into his lap. The pressure of his thigh against your core makes your head spin, but that might just be the lack of oxygen. Neither of you seem to be willing to come up for air, taking sharp, tiny breaths between sloppy kisses.
You whimper, already going limp, and Dean leans back with darkened, shining eyes. You know that look. You used to pray for and dread it all at once. It always made you feel like something close to prey, paralyzed and unable to flee his spell.
But this time is different. This time, there’s nothing you’d rather do but fall into his charm.
Dean presses another, small kiss to your lips, dragging his thumb over the tingling swell. Your tongue flicks against the pad of the finger, and he groans, pushing it slowly between your lips.
You wrap around him, sucking lightly, giving him your best, sweetest Bambi eyes. Dean’s throat bobs, his fingers digging into your ass.
“We’re goin’ home,” he mutters. “Then I’m gonna fuck you.”
That’s a lovely plan. You smile around his thumb, and he says your name, pulling his thumb away with a small pop.
“Jesus, you- You gotta tell me yes-“
“Just fuck me here,” you whisper, pulling on the collar of his shirt.
Dean glances to the backseat, then to you. “Uh- I mean- That’s- If you’re sure-“
“Please,” you push a little further forward, dropping your hand to press against the bulge in his jeans. “I need you, Dean. Now.”
And for a second, you think he’s going to demand going all the way back home. Say something about you deserving a soft bed and gentle loving, when you just want him, filthy and raw and yours. You’re so busy giving him doe eyes, you don’t notice his hand dragging down your spine and your ass, right up until it dips under your skirt, and cups your pussy through your panties.
You gasp, and Dean smirks, slowly rubbing his hand back and forth.
“Need me?” He drawls, pushing his thumb against your clit. “Like this, baby? This how you need me?”
“Ye- yes-“ Your lips brush over his, your hips starting to grind down as he drags his thumb in tiny circle, his hand still rocking back and forth. “Just- Just like that, Dean- Shit-“
You push down, kissing him with a sloppy, uncontrolled mouth. Dean grunts, splaying his free hand against your neck and pushing you down. He’s massive and warm, the hand working your pussy offering just enough friction to work you up, but nothing more. You wrap your arms around his neck, panting against his lips and moving you hips to chase more friction.
“That feels good, doesn’t it,” he mutters, kissing you between every word.
You coo, trying to kiss over his face, and Dean slaps your pussy once, leaning back with a stern glare.
“Doesn’t it?”
“Yes,” you answer immediately, already getting heavy-eyed and dazed. “So- So good, Dean, feels so good, just- More-“ You claw at his shoulders, trying to at least get to some bare skin, and settle for pressing your mouth back over his. “More- Need some more, De, now-“
Dean silences you with a deep, rough kiss, and taps his thumb against your clit in quick, harsh movements, pushing his palm down hard against your aching pussy. You cry out, trying to force your hips further down against him, and Dean squeezes that back of your neck.
“Look at you,” he mutters, almost in awe. “Few months without some cock and you get bossy, don’t you.”
“No- No,” you manage to protest. “You’re just- You’re being slow-“
“I’m being slow?” He mocks, running his fingers over the line of your panties. “Baby, I’ve barely fuckin’ started.”
You try to roll your eyes at him, but he uses his hold on your neck to turn your head, forcing your gaze back down to his. Your eyes widen, and he smirks slightly, raising his brows.
“You gonna break out some manners for me?” He asks, slowly dragging your panties to the side. “Or am I gonna need to teach you again?”
“Te- Teach me?” You choke out, and Dean hums.
His thumb drags down from your clit, parting the lips of your pussy and smearing your arousal. Your heart is trying to hammer out of your chest, every nerve in your body seeming to respond to the mockingly sweet touch.
“Dean,” you press your hands against his chest, unsure if you want to push him away or drag him closer. “Don’t- Don’t be mean-“
“I’m not bein’ mean,” he hum, the gleam in his eyes something else all together. “I’m giving my girl exactly what she wants, how she wants it.”
You blink at him hopelessly, and he chuckles, pulling you down into a long, slow kiss. It would be romantic and loving, if it wasn’t for his thumb pushing at your weeping entrance, refusing to dip even a fraction of the way inside.
“Remember how you used to beg for me?” He mutters, and your face burns with a mix of arousal and shame. “I sure as shit do. Spent hours thinkin’ about it lately, planning how I was gonna take you when you let me again. But,” he switches out his thumb for the very tips of his fingers, yanking slightly on your hair when you try to look down. “Jesus, baby, I’m worried I’m gonna break you.”
You shake your head frantically, and Dean raises his brows.
“Words, pretty girl,” he reminds you, pushing his fingers just a little big deeper. “I know it’s hard, but you’ve got it, talk to me-“
“I can take it,” you breathe out, watching him under fluttering lashes. “I- I can take it. I promise.”
Dean works his jaw, his grip on your hair tightening. “Sweetheart-“
“Please,” you breathe, leaning down until your noses bump. “I need it. I need you.”
Those are the magic words. Dean stops trying to play noble, stops trying to hold back for the sake of romance. You loved him when he fucked you like a whore and gave you nothing soft, and you’re going to love him even more when he treats you like a toy, then kisses you everywhere after.
Dean smashes his lips against yours and eases his fingers into your waiting pussy, groaning under his breath when you clench down around him.
“So fuckin’ tight,” he mutters, scissoring them inside you. “Never gonna get over how fuckin’ tight you are, sweetheart, like you were made for me. Made to be mine.”
He almost snarls the last words against your lips, pushing himself fully up to the knuckle. You mewl as he finds your g-spot with that precision that makes it look easy, that’s always made you sure you couldn’t ever enjoy someone else if you tried.
Dean pumps his fingers slowly, crooking them so they drag against that spot, and pulls you back to watch your face contort with pleasure.
“That’s it,” he grunts, pulling almost all the way out before slamming them right back in and twisting to bully against that sensitive spot. “That’s just how you like it, huh? Already gettin’ like this from just my fingers,” he chuckles, grinding his hips up against your thighs. “Imagine how you’re gonna be on my cock, sweet girl, if you can barely fuckin’ take this?”
“That- That’s not fair-“ You choke out, every word breathy and weak, and Dean just smirks.
“Isn’t it?”
You try to protest, but Dean pushes your head back down, and his kiss knocks almost every thought from your head. It’s all just the familiar, perfect way his mouth moves against yours, rememorizing something that never stopped being his. The wet sound of his fingers working you open fills the car, and your whole body burns with desire and shame. He’s right. You’re already soaked and ready for him, your cunt clenching down and still begging for more. You need that full, impossible split of him. After months of nothing, you’re worried his cock is the only thing that’s going to be able to do it.
But Dean seems to like proving you wrong today. A coil, tight in your stomach, starts to wind tighter and tighter. He drops his grip on your hair for a second to push down on the base of your spine, forcing your cunt almost right over his bulge. He reangles his hand, forcing in another finger, and you make a strangled sound.
“De- Dean-“
“We’re gonna get you relaxed, baby,” he mutters, twisting his wrist so the drag against your g-spot almost rips through your body. “Nice and relaxed ‘f me, you can do it.”
You let out a shaky breath, trying to listen, and your clit pushes down against Dean’s cock, still tight in his jeans. The pressure is perfect, combined with the brutal thrusts of Dean’s hand, and you press your cheek to his.
“That- That’s good,” you pant, clinging to the hem of his shirt. “So- Soo good-“
You whimper, and Dean hums. He’s rubbing your back, and that’s somehow almost as good as the hand obliterating your cunt. “There she is,” he mutters. “Always so good at listening when I got my hands on you, aren’t you sweetheart.” He kisses the side of your head. “That’s my girl.”
That’s what does it. My girl.
The coil snaps, and your orgasm rips through you, making your eyes cross and your body curl limply into Dean’s arms. His hand coaxes you through it, his palm rubbing against your pussy as you mewl and clench around nothing, the light pressure helping you ride it like a long, easy wave.
Dean kisses your cheek when it’s done, then right under your eye, then your nose.
“That’s one,” he mutters, and you whine. He chuckles, hiking your skirt up with light touches. “Come on, you know the rule.”
“Stupid rule,” you grumble. “Never agreed to it.”
“Never heard you complaining before,” he points out, peeling your dress off, and you stick out your tongue.
“That’s because I always forget- Dean!”
He smacks your ass, and you squeak, pussy clenching around nothing. He’s forming a tent in his jeans as he looks up at you, and you narrow your eyes. You fingers brush against the head of him, and his groan falters, his head tipping back against the bench.
You smile, pushing your hand down against his cock, and he catches your wrist, shooting you a stern glare.
“Not at young as I used to be,” he warns, and you giggle.
“But I want to,” you try to pull your hand free, and roll you eyes when he won’t let you. “Oh- Come on-“
“Nope,” he grunts, even as his dick jumps against the fabric. “You know the rule-“
“Dean-“
“Three to one,” he mutters, a dare gleaming in his eyes. “You give me one, I give you six. That’s the fuckin’ deal.”
You laugh, but his mouth doesn’t even twitch, and slowly, your smile falls into something more serious. More determined.
Damn this stubborn beautiful man and his orgasm rules. Damn you, for thinking he ever wouldn’t want to fuck you when he made you orgasm rules that weren’t proportional or fair at all.
You yank your wrist away, stick out your tongue again, and pull your underwear fully off. Dean watches you with his hands tight on your waist, eyes shining with curiosity, but patient.
And you’ve never been good at riding him, but you’ve always been good at this. You climb over Dean’s lap so your ass is near his shoulder and your face in his crotch, your back arched like some animal in heat, your pussy bare and on full display.
Dean’s never been able to help himself. One hand immediately slides around the arch of your back, then the curve of your ass, then settles back against your pussy. The other slides in your hair, petting your hair while you fumble with his belt. He chokes out your name, and you shoot him a glare, pulling out his cock with light, careful hands.
He’s so hard you’re worried he’s going to hurt himself. Pre-cum is beading around his tip, his veins throbbing like a porno. You stroke him slowly, and he lets out a sharp breath between his teeth.
“I’m serious, baby-“
“Prove it,” you say, before licking a slow, teasing stripe up his shaft.
And you know how this game ends. You’ve played it a million times before. The beautiful thing about it is that—especially when Dean thinks he’s winning—you can never lose.
You take him into his mouth, and the sound that he makes is sinful. It’s a choked, rough version of your name that sounds holy from his mouth, and comes with his fingers dipping into your heat like it’s a comfort toy. You take him until he bumps against the back of your throat and hum, swirling your tongue. Dean grunts, and pushes your head a little further down. You wiggle your ass, pussy cold and throbbing, and Dean groans.
“Jesus, woman- Gonna kill me- Fuuuuck-“
You start to bob up and down, sucking with that perfect pressure you know he likes, getting what can’t fit in your mouth in your hand. You can take him better and better with every second, letting his push against your gag reflex, and you drop that hand to play with his balls. Dean’s already giving shallow uncontrolled microthrusts, repeating your name over and over until it’s more of a choked moan.
“Can’t- Shit, baby, I can’t- That damn mouth, you’re gonna- Shit-“
You squeeze his balls and suck as hard as you can, and Dean almost roars your name, his cock jumping as he shoots thick, white ropes of cum down your throat. You swallow every drop, licking the rest off your fingers as you rise back up. There’s going to be a handprint on your ass, from where he was holding onto you. You hope you feel it in the morning.
And when you smile at Dean, you know you’re in trouble. Naked and wet for him, crawling forward so your tits press into his face and kissing him as sweetly as possible. Dean grunts, one hand shooting up to cradle the back of your head, and his responding kiss is deceptively gentle. He lets you lead it, groaning when your tongues press together, tasting himself on your lips. He lets you pull his shirt over his head and lets you trace over the lines of his muscles. You smile against his lips and lean back, and there’s that predatory glint again.
Dean’s hand twitches on your back. He wipes your chin, gathering some stray cum and slowly pressing his against your lips. You clean it off obediently, and his jaw ticks.
“Back seat,” he grunts. “Now.”
You almost scramble to listen. Rolling off of him and trying to climb over, making it halfway before you feel massive hands wrapping around your waist, holding you in place. You swallow, trying to twist over your shoulder to look at him, but Dean blows a sharp breath over your clit, and you double over with a squeak.
“De- Dean-“ You plant your hand on the bench, blood rushing to your cheeks. “Dean- wait-“
“Hmmm.” He kisses one curve of your ass, then the other. “Wait for what?”
You’re not really sure. “This- I- I can’t hold myself up,” you fumble, and he chuckles, kissing right over your clit.
“That gonna be a problem?” He teases, pressing smaller, faster kisses over the sensitive button. “Or,” he spreads your ass cheeks, humming against your heat. “Do dirty girls get what they asked for?”
Shit. “It’s uncomfortable,” you whisper, and Dean pauses.
He sighs, then kisses your clit again. You squeak when he drags you back down, and melt into his chest as he kisses all over your face, rocking you back and forth in his arms.
“’S why I wanted the bed,” he mutters, and you sigh.
“’M sorry-“
“No,” he kisses the corner of your mouth, massaging your hips with steady hands. “I’ve got it, just- uh-“
He glances up, and you watch him frown around the car with an openly adoring expression. The work of his jaw and furrow of his brow as he thinks, how he holds you so tight in his arms, it’s impossible to not love him.
“Got it,” he mutters. “Trust me?”
You nod easily, and he glances back down. His eyes soften when they meet yours, and this kiss isn’t feral or brutal. It’s just… slow. Adoring, a silent promise of what you’ve sort of always known.
Dean is going to take care of you.
He lays you out in the backseat, rubbing your thighs as you settle into the cushioned bench. You watch him with your heart in your throat, arms wrapped tight around your stomach. Sometimes, under his attention, you’re not sure what to do with yourself. He’s too pretty, too big, too much in the best possible way.
“Getting’ shy on me?” He teases, pushing up your knee, and you flush.
“N- No.”
“Hm,” Dean pins your leg against the bench, guiding the other one so it hooks over his shoulders. “Sounds like you’re gettin’ shy.”
You swallow, hugging yourself tighter, and he chuckles.
“All that work to make you relax,” he mutters, kissing his way up your thigh. “And you’re already wound back up.”
“You took too long,” you whisper, and Dean laughs.
“Sorry, sweetheart.” He kisses just the side of your cunt, and your breath hitches as he sucks a small, firm bruise into the skin. “You know I’m gonna make it up to you, yeah?”
You nod weakly, then blurt, “Yes!”
Dean’s mouth twitches, and he grabs one of your wrists, guiding it down to his hair. You weave it between your fingers, your breathing already ragged, your whole body lit up with anticipation.
“Easy,” Dean murmurs, kissing the other side of your cunt, massaging your thigh and pushing your leg a little higher. “Nice and easy, pretty girl.” He kisses you pussy, open-mouthed and wet, and you let out a high, shameless sound.
His mouth should be classified as a sex toy or something. It moves and works against you like a machine, kissing you with so much fervor you already start to see stars. You had some recovery from the fingering, but Dean’s already stripping it away with sharp, unrelenting kisses and grazes of his teeth against your clit.
“Taste so fuckin’ good,” he groans against you, the word vibrating through your body. “Never wanna live without this pussy again, baby girl, shit-“
He groans and dives back down, starting to work you open like a man starved. You push on his head, silently begging for more, afraid to open your mouth. The sounds that leave you will be embarrassing, and you’re already too far gone for them.
But Dean likes you loud, and he won’t let you hold back. He hooks his arm fully around your leg, dragging you further down, giving him a better against your pussy. You mewl when he wraps his lips around your clit, sucking impossibly hard, and Dean laughs against your cunt.
“Fuck- Fuck-“ You grab at the front bench, yanking mindlessly on his short hair. “De- Dean- Oh my god-“
He groans, pushing his face impossibly further. His tongue is deliberate and thick, pumping in and out of your cunt before pressing flat on your clit and dragging back and forth. It’s enough to drive you mad, making the coil in your stomach burn and burn and burn until your whole body is shaking with the sensation.
“De- Dean-“ You whimper. “You- Fuck-“
He nips at your clit, dragging a long, slow stripe up your pussy. Your eyes lock, and you swallow, a broken moan falling from your lips. The first time he did this, he told you that he loved it. That there was nothing better than a woman, right on his face, dripping and sweet for him. It didn’t take you long to believe him.
Here, he looks at you like you’re some kind of heaven he’s been allowed to touch. His mouth never stops moving against you, his eyes lidded and almost drunk, and your arousal shining on his face whenever he reangles it to devour you a new way. It’s a sight that could knock you off your feet, if you had any left to stand on. Dean on his knees, his broad, freckled shoulders forcing your knees apart, his attention a drug you never want to bother being clean from again.
You start to shake, your stomach seizing up as you fight off your orgasm, but Dean doesn’t tolerate that either. His mouth goes back against your clit, his tongue darting up and down and back and forth in tiny motions, almost tickling it, making the little nerves light up and-
You cum with a loud, choked sound that’s really supposed to be Dean’s name, and push at his head. You expect him to stop, and finally get on top of you.
But you forgot about his stupid orgasm rule, and he doesn’t stop. His grip tightens and he starts to make out with your overstimulated pussy. You squeak, pushing weakly at his head, and his eyes gleam.
“De- Dean- Fuuuuck- That’s-“ Your eyes roll back, your body seizing up again, almost unable to take so much. “Oh- Oh my gooood-”
Dean groans against you again, and it’s worse than a vibrator. It’s warm and deep and Dean, mixed with his filthy mouth and stubble, scraping against soft skin. Your thighs lock around his head and he lets them, his eyes never leaving yours as he slowly pulls you fully onto your back, pushing himself up onto his knees. His cock bounces against his stomach but he ignores it, using his now free hand to grope at your breast. You moan, clenching around nothing as he laps at your clit and pussy.
“I- I can’t-“ Tears spring at your eyes. “Dean- Please-“
He hums, rolling your nipple between deft fingers, and you throw your head back with a broken moan.
Warm, thick fingers weave through yours, and you blink at him under watery lashes. He’s let go of your breast to hold your hand. His thumb is dragging slowly back and forth, and his mouth isn’t slowing down, but you don’t want it to. You can see the challenge shining in his eyes. You take a ragged breath, give him the smallest nod, and he smiles against your pussy.
You didn’t know the human tongue could move that fast. You’re sure it’s not supposed to, but Dean’s never cared about things like that. He drinks you up like wine, rapidly toying with your clit—swirling and kissing and flicking and sucking like it’s candy—and your eyes roll back in your head as your third orgasm springs through your body like a geyser.
Dean lowers you down slowly, pressing one last kiss to your swollen kiss before rising back up, wiping his chin of your release and cleaning it off his fingers with a smug grin. His cock is at attention, and your mouth waters. He always gets it in. You’re a little afraid of it right now.
“Six?” You breathe out, and Dean snorts.
“You’re the one who pushed for it, princess.”
“It- It’s your stupid rule-“
“You love it,” he shrugs, slowly settling himself back between your legs. “And you’re gonna take it, aren’t you, baby.”
You wrinkle your nose, and Dean gives you a stern, amused look.
“Aren’t you?” He taps the head of his cock against your cunt, and you squeak.
“Dean-“
“You’re the one who got bratty and cocky, sweetheart,” he drawls, pushing your leg back down. “So you’re gonna take it, ‘cause I know you can.”
You swallow, giving him your best doe-eyes, and he just chuckles. Dean lowers himself down, presses a gentle kiss to your brow, and murmurs against your skin.
“That ain’t gettin’ you out of this.”
You press your face into the crook of his neck, and Dean smiles, kissing the side of your head.
“All shy again,” he mutters, dragging that massive cock between the lips of your pussy. “Let’s take care of that, huh?”
You cling to him as he rolls you both over, guiding your legs to straddle his torso and lining up his cock with your weeping, abused pussy. He pulls you gently up, rubbing your side and watching you a painfully adoring gaze. You try to cover yourself again, and he catches your hand, shaking his head.
“Come on,” he mutters, weaving your fingers together. “Let me see you.”
And damn him for being so soft and sweet, you don’t think you could tell him no if you wanted.
“Take it easy,” he says, wrapping both of his hands around your waist. “All you, baby. Show me what you want.”
“I- I can’t-“
“Yes, you can.”
You believe him, in a way you’d never believe anyone else. It might be how he looks at you. Like you’re an angel over him, like you’re really, truly letting him enter paradise as you sink down onto his cock.
He grunts, his fingers tightening against your body as his cock slowly splits you open. Even with how much he’s worked you open—your pussy so wet it’s already dripping onto his thighs—it’s a tight fit. You can feel every vein dragging inside of you, the hard curve pressing right into your g-spot and making you flutter around him.
Dean jerks his head up, squeezing his eyes shut, and you swallow.
“Sorry-“
“’S- ‘S alright,” he exhales sharply, relaxing back into the seat. “Don’t worry ‘bout me, baby. I’m good.”
A smile ghosts over your lips, even as you start to only breathe through your nose. “You look it,” you tease, and Dean gives you a half annoyed, half impressed look.
“You’re tight,” he grunts, and your smile widens.
“You’re big.”
He groans, throwing his head further back, and you giggle again. He’s sitting just right again, his chest rippling under your hands, and you feel like that angel. You feel like a goddess, with how his hands are dragging over your body, how your name falls from his lips.
“So fuckin’ perfect,” he mutters, eyes raking over your body. “So perfect.”
You take a deep breath, and start to grind down onto his cock. Dean groans, one hand dragging down to squeeze your ass, but he doesn’t move. He won’t unless you beg him, and you’re determined not to. You can ride him until your thighs give out. His cock bumps against your g-spot, and his abdomen drags near your clit, and it feels good. You rock back and forth a little faster, your breath catching, and Dean groans.
“Look at you,” he mutters, almost to himself. “Pretty fuckin’ girl, riding my cock like the needy little thing you are, aren’t you. So fuckin’ wet for me, baby, so- so tight-“
He groans, and you push down on his chest, picking up your pace.
“So big, Dean,” you moan, pushing up your chest like a pornstar, trying to make him break first. “You’re so big, feels so- so good-“
You moan, tossing your hair, and Dean makes an almost feral sound.
But he doesn’t break. The bastard never breaks, and you’ve never been good at riding him. Your thighs are already sore, and they quickly start to ache, making your movements smaller and weaker. Dean watches you start to whine, your brow furrowing in concentration, and just smiles. You both know what he’s waiting for. You don’t want to give in.
“So quiet, sweetheart,” he coos, running his hand up to palm at your breast. “Someone drove by, they’d think I wasn’t fuckin’ you properly.”
You glare at him, unable to even speak, and he chuckles.
“You know what you gotta do, baby girl.”
“Fu- Fuck you-“
“I will,” he winks. “If my girl says please.”
Your eyes narrow. His grin widens, and you think you might be about to fly apart with how bad you need it. Fuck him. Fuck him and his stupid face that you love and his big cock that makes you all jelly and dazed thoughts and useless.
“Please-“
The word barely leaves your mouth before Dean moves. A single, well-aimed thrust up into your cunt that makes you fall apart. You fall forward onto his chest with a scream, and Dean groans, giving shallower, gentle thrusts to work you through the orgasm.
“I know,” he murmurs in you ear, his words painfully soft in comparison to the pleasure wracking your body. “I know, princess. Two more to go.”
You don’t think you can take two more. Four has been your max for a very long time, and that was with a lot more prep time and space between orgasms. But Dean doesn’t seem like he’s going to give you much of a choice.
You’re a doll in his arms again, when he hauls you up into his lap. His cock leaves you for a single second, just for the adjustment, and you whimper at the loss.
Dean hums, kissing all over your face as he slides back in.
“That’s my girl,” he starts to rock your hips back and forth with steady hands, picking you up then dropping your back down so his dick drags through every inch of your heat. “Takin’ me so good. Just like that, feel that, baby-“ He pushes on your lower back, making his cock slam against your g-spot, and you sob against his neck. “Feel how fuckin’ good we fit together, my girl.”
Dean’s voice is lined with something darker now. More possessive and hungry. He fucks up into your like an animal, dips drilling forward and mouth attached to your neck. All you can do is take it, over and over until your eyes are crossing and the only words you can remember are babbles of Dean and please.
The neck orgasm is slow, blooming from where he’s slamming against your cervix and spreading pleasantly through your body. Dean moans against your skin, mouthing at your jaw and neck, his tongue dragging and kisses messy. When you try to kiss him back, it’s mostly with a mewl and lips that follow his lead. Everything is humid and light in your body, everything is Dean around you, and there’s a new, strangely hot sensation in your core that’s demanding all of your attention.
It’s tighter than the usual coil, and gets hotter and hotter with every thrust of Dean’s cock. He’s getting uneven now, his own words falling into pants and moans, his balls slapping against your ass and hands leaving prints as he folds you fully over his chest.
“One- One more-“ His voice is gravelly, almost as wrecked as you feel. “Milk my fuckin’ cock, baby girl, cum for me-“
You open your mouth to warn him about the strange feeling, but it’s too late. Dean slams home, crashing his mouth against yours, and you cum with a hoarse scream. Hot cum shoots into your cunt, right as something gushes out of you in wet, burning waves. It feels good, so good you can’t think, so good your mouth hangs open and your moans turn into pathetic, weak babbles.
“Fuck- Fuck-“ Dean groans against your mouth. “Fuckin’- Yes-“
Your body seizes and twitches around him, but even when he’s done, Dean doesn’t pull out. The last of your release pushes itself out and her collapses backward, rubbing your back and craning his neck to grin at your cockdrunk expression.
“Gettin’ stupid?” He teases, and you can’t manage to raise an arm, so you just bite his nose. He laughs, leaning up to steal another, quick kiss from your lips before settling back down.
You curl over him, resting your head against his shoulder while he pets your head, both of you still panting and coming back down. You might be there for a hundred years, or just an hour. It doesn’t matter. The car is going to reek of sex for maybe a year. Sam might never agree to ride in it again. But it was worth it. More than worth it, when you look up at Dean, and find him—just as always—already looking back.
“We’re still dating, right?” You whisper, because you have to be sure.
Dean grins, and kisses you slowly. You hum, letting your eyes flutter shut. Letting him carry you, whenever he thinks is safe to go.
“Yeah,” he mutters, and you can hear it in his voice. All the love he’s been trying to show you, for who knows how long. “We are.”