âËâżË° Lights out âËâżË°
Summary: You, your father, your annoying little sister, and your dad's best friend are going on a road trip. The truck is small, packed with bags, and heating up quickly. Once you arrive at the cabin, Dean pulls you aside and tells you to meet him after everyone goes to bed. What does he want?
Warnings!: NSFW, sex, fingering, dirty talk, degrading, oral (f! receiving), explicit details, pet names, Dean being Dean, no mentions of y/n, reader-insert
Word count: 3.3k | : this is for my Dean girlies! This fic idea was given to me on tiktok. Thank you so much and if you're reading this I hope you enjoy!!
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A rumble and loud blaring horn woke you from your nap. You jolted away, your muscles instantly hating you and retaliating with aches. âUghâŚâ Youâre sitting up in the back of a cramped truck. Bags on either side of you and squished on the floor between the front and back seats.Â
Your annoying little sister bounces in her car seat, her pigtails wobbling. She points a chubby finger at you and howls with laughter. âHAHAHA! YOU GOT SCARED BY A TRUCK! HOONK! HOONK!â She imitated the semi, pumping her arm in the air.Â
You scoff and playfully shove her.Â
In the front, your dad cruises with one hand on the wheel and one resting on his thigh. Beside him sat his best friend, Dean Winchester. You squirmed, pressing your legs together just at the sight of him. Youâd had a crush on him since you were sixteen, but you were so not his type.Â
Dean glanced over his shoulder and smirked once he saw you were awake. âMorning, kiddo. Your nap got interrupted?âÂ
You glared and tried not to pout your lip. âStop calling me kid! Iâm twenty-one! Iâm old enough to drink!â
Dean chuckled, âOh really? âCause last time I saw you âdrinkâ, you choked on champagne at New Year's.â
You grumbled something mean under your breath and crossed your arms, looking out the window.Â
Your little sister, Millie, kept blabbing on and on about some blue dog named Bluey.Â
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An hour later, your dad pulled into a gas station. You stumbled out of the car, reaching down to fix your little skirt over your thighs. You waltzed inside the gas station, hoping to flirt with a cute boy, get a soda, maybe a snack.Â
Well, two of those things got checked off the to-do list!
All the men in the gas station were either happily married or old and creepy. You held Millieâs hand and helped her to the bathroom. The bathroom had stalls, so you had to squeeze into a stall with Millie. You let her go first, since she was squirming and you didnât want her to pee herself. She swatted and did her business. Then it was your turn. As you were mid-relieving yourself, she unclipped the lock and the door swung open.Â
You gasped, âMILLIE ANNE-â You launched to try and yank the door closed, but you couldnât. Millie squealed, delighted, and ran out of the stall. As you struggled to quickly wipe and pull your skirt up, an old woman made eye contact with you. She clutched her pearls- literally!- and gasped. âThe absolute nerve!â She scoffed, then shuffled away.Â
You growled and stomped out of the bathroom to scold your sister. You scolded her, then bought yourself a soda and a small bag of chips. You tugged her outside, mumbling under your breath. âI can not believe you, Mil! You are so inconsiderate!âÂ
Everyone got piled back in the truck, and your dad peeled out of the gas station.Â
âDad, when are we gonna get there?â You asked, already bored only a half hour in. You tossed your magazine on your lap and looked at your dad.
âLate tonight, sweetheart. Weâre stopping for dinner, so itâll be even later. Maybe⌠midnight? Maybe later?â Your dad said, rubbing his scruff with his free hand. He nodded, as if considering that answer was correct.Â
âUgghh!â You groaned.Â
Dean reached his hand back to ruffle your hair. He had a giant, dumb smirk on his lips. âHang in there, kiddo; it ainât that bad. We can talk or play some car games?â
Millie squealed and threw her arms up. âGAMES! GAAMES!âÂ
I scoffed and rolled my eyes. âCar games are for children.â You popped your headphones back in and glanced out the window. Every few moments, you could feel Deanâs eyes on you. You looked over and saw his eyes glued on your thick thighs in that little skirt. You blushed and quickly glanced away.Â
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A few hours later, the sun dips low over the horizon. The sun is painted a beautiful orange and yellow hue. The sky matched molten lava as the last rays of sun peeked through clouds.Â
âDaddy, I hungry!â Millie whined, rubbing her tummy.
âI know, baby girl. Give Daddy a few more minutes, okay? Weâre stopping just ahead.â Dad said, reaching down to lower the radio volume.Â
You lean forward, elbows resting on the back of the front seat. âWhere are we stopping at?â You asked, your hair forming a curtain around your face as you leaned down.Â
Dean licked his lips and tucked some of your hair behind your ear. âSome little Ma and Pop diner. They always serve the best food.â Dean answered for your dad. Dad nodded and grunted in agreement. Your eyes met Dean, and a fire lit low in your belly. Deanâs jaw tightens, and he flexes his biceps, hoping youâll look. You do and blush a deep scarlet.Â
Dad pulls into the Ma and Pop diner. Itâs a cute little white building with flowers scattered across the front of the building. You stumble out of the truck, knocking a few bags onto the pavement. âShit.â You curse, bending down to pick one up.
You donât know it, but you accidentally gave Dean an eyeful of your ass. He sees the cute little pink thong you wore. Dean groaned and reached down to hide his growing erection. âFuckâŚâ he cursed as he felt his cock throb. It buzzed to life and pressed angrily against his jeans zipper.Â
You straightened up and followed your Dad and Millie into the restaurant. The big blue sign read, The Cozy Corner. Deanâs eyes stayed glued on your ass as you swayed your little hips, completely innocent. His cock grew harder and angrier. Throbbing painfully. He reached down to adjust himself again.Â
Everyone slides into the booths. You and Millie on one side, Dad and Dean on the other. Dinner goes by quickly and quietly. Everyone orders water to drink. The menus are laminated and sticky from use. The air smells like coffee and grease. The waitresses smile tiredly and have little notebooks and pens.Â
You giggle around a bite of burger as your dad makes another dumb joke. Dean keeps wiggling his hips to try and get comfy. Millie throws a ketchup-covered fry on the floor. It's chaos. But it's perfect.Â
The drive after dinner is quieter. Both you and Millie are asleep in the back. You two definitely look like sisters; both of you are leaning back, hair wild, with your mouths wide open and dripping with drool.Â
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At around midnight, your eyes crack open. You glance at your surroundings, trying to get a feel for whatâs happening. Once you wake a little more you get more conscious of where you are. A dark forest swallows the little truck. The only things you can see is what the truck's old headlights illuminate. Dad twists and turns the truck down the curvy back road.Â
âMmpph⌠are we almost there?â You asked Dad. You rubbed sleep from your eyes and stretched as best you could in the back seat.Â
âAlmost there, honey,â Dad said.Â
You sneaked a glance at Dean. His eyes were glued to your legs again. You blushed and looked down, only to blush even deeper when you realized your panties were visible. You tugged your skirt back down. You looked up and your eyes met Deanâs again. He licked his lips and nodded, just once.Â
Dad pulled into the bumpy, gravel drive. He parked the car and killed the engine. âWell, weâre here.â He announced. The truck's interior lights blinked to life. Millie groaned and covered her eyes with her little hands.Â
Dean hopped out first, then opened the back door for you. You got out with a small, âThanks.â
Dad helped Millie out and into the cabin. He, of course, checked inside first to make everything was safe. Then he laid her in her own room on the small twin-sized bed.Â
Dad came back out to help with the bags. He grabbed his own bag, then Millieâs. âEveryone has their own room. Sweetheart, yours is down the hall from Millieâs. Dean, yours is next to mine. Everyone get settled, and if you need anything, just holler, alright?â He asked. Once you both nodded, he nodded, then disappeared into his room.Â
You turned to head down the hall to your room, but a hand on your arm stopped you. You turned and were face to face with Dean. His breath tickled you, warm and smelling of coffee. He gently cupped your cheek and stroked the soft skin.Â
âMeet me in my room once everyones asleep. Mm âkay, baby?â Dean asked in a low purr. You felt heat in your lower belly, tempting, so you nodded.Â
You disappeared into your room and tugged your bag into the corner of the room. You laid in bed and your imagination got the better of you. You tried thinking of what Dean wanted to do with you.
âWhy does he wanna see me?â You asked, curling a piece of hair between your fingers.Â
You lose yourself in a dirty fantasy, one of your favorites to indulge in late at night.Â
You on Deanâs lap as he gently fucked you, whispering sweet nothings in your ear. You sigh and let your hand run down your body. You slip your hand under your little skirt and find your panties damp already. You rub slow circles over where you know your clit is. You whimper and arch your back into the touch. âOh⌠godâŚâ You wanted to cum so bad, but hoped Dean wanted what you really wished he did. You pulled your hand out of your panties with a grunted huff. You sit up and try to busy yourself.Â
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You barely make it five minutes before slipping out. You pad down the hall to his room. You cracked the door open. Dean was standing in front of the door, hand extended like he was about to walk out. He saw you and you saw his jaw clenched.Â
âClose the door, baby.â he growled.Â
You closed the door and heard backed you against it. The door knob dug against your back and you whined. He cupped your face and smashed his lips against yours. Your eyes fly open, âwha-â but you don't get anything but a moan out. Finally. Finally. Finally!
You crush for the past odd number of years was kissing you. And you were standing there dumbfounded?!Â
You went to kiss back, just as he pulled away.Â
âOh babyâŚâ he stroked your cheek. âI've been waiting all fucking afternoon to do that. That goddamn skirt you're wearingâŚâ his eyes trailed down your body to rest on the little pink skirt. âYou do that on purpose? Teasinâ me? I knew you liked me. But God⌠im only a man, baby.â He nuzzled his nose against your neck, inhaling your scent.Â
You felt Deanâs hand slowly travel down your body. He gently strokes your inner thigh. Then, in a low rasp, he asks, âbaby⌠please say yes⌠please tell me I can go furtherâŚâÂ
You would have slapped yourself silly if you ever even thought of saying no. So, of course, you nodded slowly.Â
âWords, baby⌠I need you to say it. Say we can go further.â Dean purred, his hand slowly slipping under your little pink skirt.Â
âYes, Dean. PleaseâŚâ You basically whimper.Â
Dean groans and drops to his knees. He wastes no time, sliding your panties to the side and licking a long, wet stripe through your center.Â
You cry out and your hips jerk from the delicious touch. He licks big, long stripes up. Then pulls back, only to do it again. Your hips jerk and you moan loud. Dean nibbles on your inner thigh, and with a rough growl, whispers, âquiet, baby⌠we donât need your daddy coming in here to check on us.â
Dean dives back in and your eyes roll back. You have to cover your mouth with your hand to keep from moaning. Itâs so hard when heâs feasting like heâs never ate before. You whine, muffled against your hand. Your other hand reaches down to tangle in his short, spiky brown hair. You tug and pull, guiding his face. You feel his dumb smirk as he keeps eating you out.Â
Just when you start feeling that delicious curl low in your belly, he pulls away. He stands abruptly. You whine and pout your lower lip out.Â
Dean swats your ass through your little skirt. âHush, baby. I ainât finished.â He tugs your skirt and panties down to your ankles. You kick them off and lift your arms. He chuckles, âeager little thing, ainât ya?â He helps you take your shirt off. He gasps as he sees a cute little white bra left. He gently strokes the bottom hem of the bra. âSo pretty, baby⌠this all for me?â He asks, one hand slowly sliding back to undo the clasp.Â
Once your bra falls to the ground you feel your cheeks heat up. You blush and look down at your bare feet. You felt shy all of a sudden. Bare and exposed to one of the people who knew you best.Â
Dean gently stroked your cheek. Then he tilted your head up to look at him. âBaby⌠Youâre so gorgeous. Donât go getting shy on me, now.â Your eyes met and he smiled softly. âI ainât gonna hurt you, precious. Just tell me if anything makes you uncomfortable, or if you donât like how something feels. Okay? I ainât using ya.â He gathers you in his arms, holding you close. âI just wanna hear my girl make those pretty little sounds. Make ya feel good⌠Mmm âkay baby?â He stroked your hair. You blushed and nodded.Â
Dean nodded and slowly pulled away. He helped walk you over to the bed he was assigned. âLay down, baby. Get comfy. Iâm gonna get everything ready. If you need anything donât be scared to ask.â You laid down and got the right amount of pillows situated. You kicked the blankets to the edge of the bed.Â
Meanwhile Dean was digging around in his bag. He pulled out a black box and a bottle of some clear liquid. He set them on the nightstand. Then his hand went to his zipper. The sound of the zipper filled the silence and he winced, eyes shooting to the door. Both of you stayed silent, listening for any movement outside. Nothing. He slowly shucked his jeans off, tossing them aside.Â
You tried not to stare too hard at the bulge in his boxers. He was leaking, a wet spot was very clearly visible, and stained to the front of his boxers.Â
Dean chuckled when he saw you staring. âYeah, yeah. I know this is a damn sight. Iâve been like this since you bent over in that fucking skirt.â He tugged his shirt off over his head.Â
You gasped and blushed. Your thighs instincvitvely squeezed together. You felt warmth both in your cheeks and lower areas. Your pussy throbbed just at the sight of this man. He was muscular, thatâs for sure. His abs were light but defined. His biceps flexed as he shucked off his boxers next. And god⌠those forearms.Â
Now you got an eyefull of his obviously hard dick. It was pointed up in arousal, and wet at the top. Hairy, like natural, but slightly trimmed.Â
âLike what you see?â Dean chuckled again. Then crawled over you, and, God⌠you never thought you could get so wet between the thighs. You whimpered and squrimed. âShh⌠just lemme touch you, sweet thing.â His hand slid up your thighs, digging his fingers into the supple skin. His hand disappeared between your thighs and your back arched like an bow. A soft moan escaped your lips as he gathered your wetness. âSweet thingâŚâ He groaned, âso wet? All for me?â He grinded against the mattress as he got your pussy ready.Â
Your fingers dug into his hair, just needing something to hold on to. You moaned and squirmed, your hips raising into his touch. âDeeâŚâ You moaned his nickname, your eyes closing.
Dean tsked, âno, baby. Eyes open, now. You can take two fucking fingers on your pussy. You ainât a baby. Open those beautiful eyes. Now.â He said. You whined in protest, so his fingers slowly started moving away. Your eyes shot open immediately. âGood, girl.â He rewarded you with circles to your clit. You moaned and your back arched again.Â
Once he decided you were nice and ready he pulled his fingers out. You whined and squirmed, clenching around nothing. He shushed you, then dragged his cock through, âshhh⌠I was just getting you ready, sweet girl.â He reached over to the nightstand. He grabbed the box and tugged out a small plastic square. He ripped it open and rolled the condom up his length. He grabbed the clear bottle and squeezed some of the liquid in his hand. He rubbed it between his hands, then rubbed it on the condom. His jaw clenched and he groaned. Stroking himself to get himself ready, now.Â
âWhats that?â You asked.
âWhat- oh. The liquid? That's lube, baby. It helps things be smoother. Less friction. Makes things feel way better for you.â He said softly, cupping your cheek. He lined up, the head of his cock nudging your entrance. âTake a deep breath, baby⌠in⌠outâŚin-â he gently pushed his head inside. You gasped, squirming from the sting. âShh⌠shh.â He gasped, his voice shaking. You were squeezing him like a vise. He tried so hard not to thrust in, literally shaking from the force of holding himself back.Â
âBaby⌠baby, fuck⌠stop squirmingâŚâ He soothed, reaching one hand out to squeeze your hip. âTake a few deep breaths, sweetheart. You're making this harder âf me.âÂ
You took a few shaky deep breaths, trying to calm yourself down. It works, the sting soothes to a gentle throb of pleasure.Â
âGood girl.â Dean groaned, slowly thrusting home. You moaned and bit your lip hard. Dean shook his head. His thumb reached up to smooth your lip back out. âNone of that, sweet thing. Lemme hear those pretty noises I pull outta ye.âÂ
Deans thrusts started out full, repetitive, and so sweet with pleasure. You moaned and squirmed. Your back arched as you pressed your hips into his. The sounds and smells filled the room; slapping skin, soft feminine moans, male groans. The smell of sex and a vanilla candle swirled around the warm bedroom. Outside the window the forest mattered with soft droplets of rain. The scene was perfect.Â
âDeeâŚâ you moaned, barely five minutes in.Â
Dean felt the tightness growing in your pussy, he knew you were about to come. He nodded, âI know, baby.â He tried to keep his thrusts even and repetitive. Knowing girls hate change in sex like this. One thing worked? Stick to it. So he did. But God, your tight, warm pussy made him wanna lose himself.Â
âFuck⌠Sweetheart.. why haven't we done this before?â He groaned.Â
You giggled and buried your hands in his hair again. His eyes stayed transfixed on your breasts. They swayed and jiggled with every thrust.Â
âGoddamn⌠FUCK!â He spilled inside the condom, coming hard without warning. You came next, your back arching and your nails digging into the back of his neck.Â
âAhh!â You cried out, tears springing in your eyes.Â
Dean pulled out, but didn't move away. He slumped against you, bury his face in the valley between your breasts. His breathing was heavy, matching yours. You both laid there, panting and spent. It was silent for a while.Â
Dean finally broke the silence. âThat was fucking awesome. We are so doing that again.â He ran his fingers through his disheveled hair.