Dean Winchester
Summary: Your Father's best friend is your "babysitter" for the day, since your father doesn't trust you enough to be on your own. Despite knowing Dean is always busy due to hunting, your father doesn't care. Dean was the first to complain, but when he saw you, he insisted anyways.
Pairing: Father's Best Friend!Dean Winchester x younger reader
Warnings: Smut, inappropriate content, dom!Dean, obsessive behavior, perverted thoughts, fingering, unprotected sex, dirty talk, size kink, no use of yn, fluff (if you squint).
Notes: Idk, i just want to be here.. D:
Dean Winchester was the first person who came to your father's mind when it comes to babysitting— but you don't even need a babysitter since you're old enough to take care of yourself. But your father doesn't seem to care about that, and doesn't trust you enough to be on your own. You knew the man is always busy because of hunting, but your old man doesn't seem to care about that because Dean ”owes" him.
You didn't really care what it meant, so you sulked on the couch with your crossed arms. Usually, your petty behavior makes your father give in, but he didn't. It was actually really frustrating. Your father told you that he'll be gone for a few days because of a hunt in Illinois, and he didn't want you to come because it's "dangerous". As if everything he does isn't dangerous.
”—Dean, just three days. I'll make it worth your while after I go back.." You heard your father thump in the kitchen, trying to be persuasive but he just sounds like a desperate dog. You sighed, grabbing the magazine and just read until the time pass.
In Dean's side, he had been telling Sam that he'll be gone for a few days to "babysit a damn girl", thinking you'll just be another annoying kid that he'll get stressed out on. That's where he's wrong.
It had been a few hours, and the doorbell rang. You were about to walk to the door but your father beats you to it, walking fast towards the door. You stood by the living room doorframe, crossed arms and staring at the door. Your father opened the door, revealing a. attractive older man with slight stubble often has a kind of quiet, effortless confidence about him. Well, you'll be damned.
You cleared your throat, standing stiffly. His eyes met yours, and it's the most beautiful green eyes you've ever seen. If you're mistakn, you'll take his eyes as the color of the forest. And he's fucking hot. You couldn't even catch up when your father and him were talking. Of course you know Dean Winchester, but you haven't really met him face to face. The slight stubble along his jaw and chin gives him a rugged, relaxed charm, neither too polished nor unkempt.
”Oh, yeah. Of course." He had said to your father before walking in with a smirk on his face, trying to remain respectful but his eyes differ when he looked up and down your body.
And suddenly, your normal house clothes doesn't seem comfortable anymore— maybe just yank it off. No. That's worse.
You pushed yourself off the doorframe, walking towards them as they walked towards the kitchen. You followed them, watching as your father grabbed two beer cans from the fridge.
"Hi, daddy." You smiled sweetly at your father, which he replied with a light-hearted glare.
"You're not having beer."
Damn.
You rolled your eyes, walking towards the fridge— ignoring the fact that your arm brushed lightly against Dean, sending tingles down your spine. It's not that deep. But fuck. He's so hot.
"You know, Dean. Why did you even take my father's request?" The words left your lips easily, raising an eyebrow as you looked at him.
"Just helping an old man." He smirked at you, taking a swig of his beer.
His smirk is so fucking attractive, and everything else about him. You grabbed a soda from the bottom of the fridge, bending down purposely to grab the can. You felt his eyes trail down your ass, so you smirked in victory.
When you stood up straight, you turned to look at him with a raised eyebrow. "Hm?"
He cleared his throat, shrugging.
The next few hours, your father had left to do business.. or hunting. He isn't really subtle about it, nor obvious. But at least you know, instead of him hiding it.
You were in the kitchen, contemplating everything while Dean was in the living room, watching the television and it was too loud. With an annoyed sigh, you walked towards the room and stood behind him on the couch.
"Will you turn it down?" You asked, crossing your arms and looked down at him.
Dean blinked, turning his body around and looked up at you from where you were standing. He raised an eyebrow. Fucking delicious. "What did you say, Sweetheart?" He asked, turning the volume higher with a familiar smirk on his face.
You rolled your eyes, grabbing the remote from his hand and turned it down. "I said turn it down." You repeated, throwing the remote on his lap and turned to walk back in the kitchen.
He lets out a chuckle, making you halt on your steps and turn around with crossed arms.
"Come on." He said, patting the space next to him.
You would've decline the offer, but the look on his face is slightly screaming that he doesn't like it when someone disobey him. So you sat beside him on the couch, your thigh brushed against his jeans. You cleared your throat, watching as he turned the volume of the television high.
You don't really care about what's playing on it since you can feel his fucking radiation hot on your skin, his breathing, his smell. Everything. He smells musky, and the beer he's drinking lingering around him. In a good way.
You looked at his hand that was wrapped around the beer bottle. Imagining it wrapped around certain something. You heard him cleared his throat, so you looked at him, finding him to be already looking at you. Heat spread across your cheeks, looking away.
"What's bothering your mind, hm?" He hummed quietly, his voice low and darker from more than you anticipated. A warm hand wrapped on your thigh, his thumb rubbing the skin back and forth. It really didn't help your imagination. In fact, it made it worse.
"It's nothing, just— I'm sleepy." You lied, shrugging.
"You're lying." He interrupted, leaning closer to your face that you can feel the hotness of his breath hitting your face.
What can his hands do? If it rub circles on your clit, or when his digits moves in and out of yo—
"Hey." Dean called, raising an eyebrow and an amused smile on his face.
"Hey, Dean?"
"Yeah?"
"Do want to fuck me?" That question basically threw you off of the hill, your soul leaving your body at how obvious and weird it was. You cleared your throat, shaking your head quickly. "Fuck, I mean—"
His lips pressed against yours harshly, his hand holding the back of your neck. He wasn't really deepening it unless you respond positively. So you kissed back, parting your lips. When he felt that, his tongue brushed on yours.
You can feel him pull you on his lap, a hand on your hip as you make out. His tongue slipping inside your mouth, and his teeth nipping your lip. He pulled away, breathing heavily and pressed his forehead against yours.
"Damn it." He breathed out, looking up at you as you sit on his lap. You leaned on him, pressing gentle kisses on his jaw. He lets out a shaky breath, his hand wandering around your body. A hand on your hip, and on your waist.
Rolling your hips on his lap, his hands tightened around you while you suck and kiss his neck, leaving marks. Occasionally biting on the skin gently and kissing it after. He grunted, pulling your face away from his neck and kissed you with harshness. He wrapped his arms around your waist, moving you to lay on your back on the couch with him on top of you.
He chuckles when he pulled away, looking down at you, unbuckling his jeans. "May I?" He whispered, you nodded. "Words, sweetheart."
"Yes, fuck yes, Dean." You breathed out, wrapping your arms around his neck.
He grabbed the hem of your shorts along with your underwear and pulled them down. He licked his lips upon seeing your cunt, his hand immediately going to your clit as he presses slow circles against it. You moaned softly, back slightly arching from his touch.
He pulled his fingers away, putting it against your lip so you took it in your mouth, tongue automatically swirling against his fingers. He grunted, imagining if it's his cock what's wrapped around your lips. He pulled his fingers away, placing it against your entrance and circled it before pushing in. His fingers were bigger than once of your fingers, stretching your hole better.
"Fuck, Dean.." You breathed out, burying your face on the crook of his neck.
He smirked, letting out a soft chuckle before pushing his fingers in and out before pulling away again. You whined in anger, moving to sit up but he stopped you by bringing his fingers down to your slit for the first time that night, he made you gasp as he forced two inside. Your walls clenched around him as he curled them, triggering your g-spot.
You squirmed and whimpered lightly, wanting so badly to scream. "You have to be quiet, sweetheart." His voice purred in your ear.
"P-please." You whispered, furrowing your eyebrows in agony. You felt like you'd been teased all night, when all you wanted was for him to give you a good fucking.
"What?" He asked as he left kisses on your breasts, sucking on them gently, leaving little red marks. His fingers still pumping in you, but too slowly now, the only purpose to tease you. You pressed your fingers into his arms, wanting more.
"Please." You whined. Having to be quiet turned out to be total torture for you as you arched your back, your body tensing as your oversensitive pussy was ready to climax around his fingers. "I want you." You said.
"Tell me what you want." He demanded, and you wanted to growl in his face for making you beg.
"Fuck me." You let your eyes flutter open as you fixed your gaze on his, "Fuck me, Dee, please." It wasn't necessarily your voice, more likely the choice of words, but the older man let out a deep breath and a sensual moan as he too had truly waited too long.
"Use my name." He growled, removing his fingers from you, the lack of friction just torturing you even more. Your breathing became rapid in anticipation as you watched him stroke his cocm and positioning it exactly where you wanted him to.
As he entered you, you gripped the bedsheets and gasped. "Shhh." He reminded you to be quiet as he put his hand over your mouth. Wanting to close his eyes from the amount of pleasure he felt he kept them open as he wanted to see your face, observe your reaction and save the memory forever.
You furrowed your eyebrows, closed your eyes shut and wrinkled your forehead, doing your very best not too cry out in ecstasy.
As your walls adjusted to his thickness, Dean picked up his pace. He wanted to go faster, but when the couch's leather squeaked he groaned in annoyance. Instead he fucked into you slow, but rough. You felt like you melted beneath him, into a pool of wetness and pleasure.
When he removed his hand from your mouth he laid his face into the crook of your neck, silent moans escaping his lips as he slowly withdrew his length and then thrusted forcefully into you. Clawing on his back you felt a tear run down your face, a silent protest of the feelings you weren't able to let out by moaning loudly or screaming.
"You feel so good, Dee." You whined. He had said he wanted you to use his first name, but there was something about you using his title that he loved. The sound of it made him twitch inside you, and in response you clenched your walls around him
Thrusting in and out of you in that slow pace, as to not make much noise, he grabbed your jaw and looked into your eyes. "Tell me how much you like it, sweetheart." He demanded. You closed your eyes shut as you furrowed your eyebrows by his next deep thrust. Panting as quietly as you could you whimpered lightly.
"The feeling of you." You paused as he pushed in once more, "inside of me.." You let out a stiffled moan. "Is amazing."
He did another couple of punishing thrusts as you bit onto your hand to stop yourself from screaming. But when he reached down to circle your clit at the same time, you weren't able to hold it back any longer.
You wrapped your arms around his neck, and came all over him as you nearly bit your tongue trying not to cry out. He kept his pace as he too started closing in on his high. Your rapid breathing started to calm down as you still squirmed under his mercy, but as you parted your lips to say what you did next, the older man struggled not to cum solely based off of it.
"Please cum in my mouth, Dean." He let out a deep growl as he immediately pulled himself out of you, his member drenched in your fluids. You pushed him down on his back as you took his cock in your hand. Just touching him made your sensitive clit throb once more.
As your lips touched upon his head, Dean closed his eyes in pleasure. Taking him deep into your mouth you applied the quick pace you knew he had wanted to fuck you in. Secretely you enjoyed the taste of yourself on him. When he proceeded to grip your hair in a tight grip you knew he was getting close.
He pushed the back of his head into the mattress as he furrowed his eyebrows, overwhelmed by the pleasure you gave him by running your mouth all over his length. When he bucked his hips and a groan left his lips you felt a thick line of his cum shoot into your mouth, the warmth of it filling you up.
His grip on your hair tightened as he stopped you from bobbing your head, as him cumming made it all too sensitive. The second he let go you withdrew and swallowed the load he had given you, and he loved it.
