Pretty Little Baby
STANFORD!SAM WINCHESTER X F! READER
SUMMARY: You've liked sam for a while and you finally put on your big girl pants and ask him out, it turns out to be a bit more than expected
TW: MDNI- fluff, smut, car sex, semi-public sex classmates/friends to lovers, unprotected P in V (don't do it), fingering, SoftDom! Sam, pet names, praise, teasing/edging, very briefly mentioned male masturbation
BASED ON THE SONG "PRETTY LITTLE BABY" BY CONNIE FRANCIS
WORD COUNT: 3181
You and Sam met when you first started college, he was a sophomore while you were a freshman. you had been in class with him and coincidentally you had forgotten a pencil so you asked him for one. From there you started talking more, it started with just sharing notes but eventually it turned into outside of class.
the two of you would have lunch sometimes or study in the library. You may have gained a slight crush on him but he didn't need to know that, not yet at least.
♫ Pretty little baby, you say that maybe You'll be thinkin' of me, and try to love me Pretty little baby, I'm hoping that you do ♫
sometimes while you two would be studying you would catch Sam staring at you but when you looked at him he would immediately look back towards his book or notes. sometimes you wondered if he had a crush on you too. you wondered if he would think of you in his free time like you would about him. you really hoped he did.
♫ You can ask the flowers, I sit for hours Tellin' all the bluebirds, the bill and coo birds Pretty little baby, I'm so in love with you ♫
Sometimes after classes or the library with Sam, you would sit in the field on campus by yourself. you would lay out a blanket and would read for hours but sometimes you would get bored of the books and feed the birds around you, talking to them, usually about Sam and how pretty and sweet he was.
sam was the first guy who treated you as a complete equal, sometimes he would say that you were even better than him when you would figure out something before him. He made you feel good about yourself but him being handsome and pretty was just a little extra benefit. One day in particular you were talking to the flowers and the birds that you realized just how much you actually liked him, shit you loved him.
♫ Meet me at the car hop or at the pop shop Meet me in the moonlight or in the daylight Pretty little baby, I'm so in love with you ♫
The next day you had a class with Sam you decided that would be the day to do it, the day to ask him out (on an actual date). you were nervous obviously, he was tall, handsome, and practically your best friend, but you noticed the way he looked at you even if he didn't think you knew. he had to feel something right? If he didn't you hoped you wouldn't mess everything up. you cared about him and didn't want to lose him even if it meant the friend zone.
You stop sam as the two of you walk out of the lecture hall. "hey sam um, can we talk real quick?"
"um, sure?" Sam stops walking and steps off to the side of the path leaning against the wall outside and crossing his arms "Whats up?" concern flashes in his face, you cant tell what hes really thinking though
you stand in front of him looking down at your shoes avoiding eye contact before speaking "I was wondering if you wanted to go out tonight?" sam tilts his head confused on why you were making a big deal about hanging out. you speak again to aide in the confusion "i mean like a date" you mumble
"sorry what was that?" sam smiles and leans closer, he had heard you he just wanted you to really mean it. you roll your eyes at him "I meant would you want to go out together, as a date..?"
sam smirk grows wider when you speak up "Of course sweetheart, how bout that drive-in movie tonight maybe the carhop before?"
♫ Now is just the time, while both of us are young Puppy love must have its day Don't you know it's much more fun to love While the heart is young and gay? ♫
Sam picked you up exactly at 6 to take you to the carhop and the movies, he had the whole night planned for the two of you.
he stepped out of the car knocking on the door of your apartment flowers in hand behind his back. you open the door attempting to slip on one of your heels but stumble into him when your finger slips off the strap
"Whoa easy there," he smiles down at you chuckling as he catches you and helps you stand back up. "don't want you to hurt that pretty little face now do we?" you smile abashedly at him your cheeks flushing in embarrassment. he smiles again holding out the flowers he got for you "Here for you, figured you'd like 'em, always see you starin' at the ones on campus when we walk by"
You take the flowers from his hands. it was a bouquet of pink tulips and white roses with baby breath scattered throughout "Wow these are so pretty, thank you, Sam"
"of course" he says with a smile "so um you ready?" he ask looking you up and down holy shit you were hot
"yeah just got to get this damn heel on" you roll your eyes pouting at your heels
Sam gets down on one knee kneeling down "Here let me help" he says as he helps adjust the straps of your heels
oh my god, he's hot like this, shit hes hot just doing anything, maybe later I can get him on his knees for a different reason, ok stop, no, bad thoughts
he stands up again to his full height towering over you, after fixing your heels "There that should be better" he smirks down at you "ready to go now then?"
"yeah let me just put these somewhere" you motion to the flowers in your hand before retreating back into your apartment putting the flowers sam got you in a vase before coming back out "ok ready" you smile sweetly up at him
Sam takes your hand as you close and lock the door to your apartment, guiding you down the stairs making sure you don't trip in your heels with his hand on the small of your back. the two of you reach the car and he opens the passenger door for you ever the gentleman he is. when you slide into the passenger seat he shuts the door behind you after making sure your feet are in before rounding the hood getting in the driver's seat starting the car.
As he begins to drive to the carhop for dinner he continues to steal glances at you through the corner of his eye. you notice how his hand grips the wheel tight enough to make his knuckles white. so you decide to be bold and grab his hand to put it on your thigh. when he feels your hand grab him he instantly switches the hand he was driving with and complies with your grasp. when he feels you plant his hand on your thigh you can see his eyes flick over wearily as if to ask 'You sure?' and you just hold his hand there so he takes it as a yes. you can feel the tension leave his body as his hand relaxes on your thigh giving it a light squeeze. his hand trails up and down your thigh ever so often getting really close to going up your dress but never actually getting there. teasing you.
soon enough the two of you are at the carhop enjoying your dinner and sharing a milkshake and you keep stealing his fries even if you have plenty of your own. you and he are sharing simple banter as always, filled with chatter about classes, random facts, and other things. Sam glances at the time "shit better get going, don't wanna be late for the movie" Having already paid he starts the car and backs out of the spot passing all his fries to you to indulge in as he drives. his hand finds its way back to your thing more bold this time as you absolutely devour yours and his fries.
the movie Sam had picked the two of you to go see was The Notebook a recent release that was supposed to be sappy and cute as Sam had said. Sam picks a secluded spot away from other cars with the perfect view of the movie just as it starts.
Sam kept his hand on your thigh stealing glances at you throughout the movie his eyes roaming over you, catching on your lips every time. you pretended not to notice or let it affect you as much as it did, but his stares made a certain feeling coil in your stomach. you can hear small mumbles from sam under his breath as he talks to himself. you can make out what sounds like a pep talk you think?
Sam suddenly turns to you staring at you for a good second his eyes flicking from your eyes to your lips before speaking up "ok you like really dont have to if you dont want to, i understand first date and all, i just- i like totally understand if you wanna take it slow and all..." sam rambles on "i just- can i kiss you, maybe? please?" you can see the nervousness in the way he avoids your eyes and rubs the back of his neck with his hand
"yes," you answer without hesitation and suddenly his lips are against yours and the movie fades to background noise. all you can sense is just Sam, Sam, Sam. he fills your senses as his hand cradles your head gently his tongue sliding against your lips as to ask for permission. your lips part, his tongue dancing and tangling with yours in your pretty little mouth as he moans softly into your mouth.
he pulls away from the kiss and you slightly chase it before you pull away as well, a sultry look in your eyes. "backseat," he says with a desperate tinge "Please baby?"
you climb into the back seat instantly and wait while Sam struggles with getting his large frame over the center console causing a giggle to bubble from your throat and leading Sam to look at you "You think this is real funny huh?" you nod "We'll see whos laughing in a second" and just like that he's in the back seat with you pulling you onto his lap earning a small yelp from you. his mouth is on you again more desperate this time his hands roaming over you as he trails open-mouth kisses down your jawline. your fingers reach his hair messing up the perfect little bangs you've grown to adore. he smiles against your throat as he sucks a mark there trailing over your collarbone with peppered kisses. his hands grip your hips grinding you against him making you let out a soft moan. sam pulls away and brings a hand to your cheek caressing it softly "you sure sweetheart?" he whispers
you nod "yes, i want this, I've wanted this for a while"
he kisses you again his hands making their way under the hem of your dress squeezing at your thighs as you grind into him, moaning into your mouth. your hands grip his shirt tugging up on it. Sam pulls away from you for a split second lifting his arms to help you get it off of him, and then immediately goes to the zipper of your dress to get it off of you. he needed to see you. he pulls the dress over your head and tosses it to the front seat as he kisses along your cleavage. "so pretty baby" he says against your skin as he grips at your breast making his way to the clasp of your bra. you moan as you continue to subconsciously grind against him searching for any kind of friction. "so fucking perfect" he mumbles into your breast. pulling the perfect bud in between his lips making you gasp as his other hand runs his fingers over your thighs.
sams hand travels up your thigh reaching your clothed pussy. you let out a needy moan as his hand caresses you through your already-soaked panties, sam looks up at you making sure you ok with it. you nod. he can feel how wet you are through the cotton as he pushes it to the side making way for his fingers "Aw so needy for me baby, huh?" he whispers into your ear. you nod desperately biting your lip, he is so close to where you need him most but so far away "P-please Sam, need you" you whimper.
Sam finally indulges in both of your wants. his fingers fill your tight pussy filling you up and hitting that perfect spongy spot inside of you making you moan and writhe against him searching desperately for any movement your pussy clenching around his fingers. you moan and whimper as he starts to move his fingers inside.
"mm fuck Sam, faster please" he instantly picks up the pace with your begging, his thumb circling your clit applying just the perfect amount of pressure to it. you can feel the coil in your stomach tighten as your legs start to tense. Sam must be able to feel it too as he pulls his fingers out of you instantly, making you whimper at the sudden emptiness. he holds your eyes as he licks his fingers clean of you, groaning as he does so before bringing his hand to your cheek and caressing it with his thumb "Need you to finish on my cock baby"
you pout slightly but nod in agreement within a millisecond already fumbling with his belt buckle. after getting his belt off the jeans come down quickly as well leaving him in only his boxers with his jeans pooled at his ankles. you could see the outline of his length through the black material- thick and heavy- it was begging to break free pushing at the waistband of his boxers. you rub your hand along it through the material earning a groan from him his head tilting back, his eyes shutting. his hips buck into your hand "P-please baby, need to feel you, wanna fill you" his voice is desperate and hungry, He's letting you lead for now. you remove your hand from his length and adjust so you can pull his boxers down.
you pull his boxers down tantalizingly slow, and his cock springs free before resting think and heavy against his stomach, you take a second to admire it, it is significantly larger than expected. the tip was already leaking pre cum, the way it twitched showing his desperation. you run your thumb over the bead using it to wet the tip making him moan. he looks at you again, his gaze sharpening at you you were teasing him and he couldnt take it anymore.
his arm snaked around you quickly pulling you up against his chest your arms on either side of him. he lines himself up with your entrance entering you slowly letting you adjust to his size. he bottoms out in you his tip perfectly kissing your cervix. he lets you sit for a second letting the pain of the stretch turn into pleasure. you let out a soft whimper, clenching around him. sams head meets the back of the seat again groaning at the feeling, you were so perfect just for him, like you were made for him, the ways your bodys fit together.
Sam begins to thrust into you slowly at first, testing the waters. your lips part with a soft whimper your head falling onto his shoulder feeling him hit that perfect spot inside you.
sam can feel the way you clench around him everytime he hits it, and it makes it hard to control himself. it had been torturous months of waiting for him hoping you would make the move first, months of fantisizing about you wishing it was you instead of his hand. now here he was, and he was trying so hard not to come undone right there.
he picks up his pace now, knowing you can take it, his hands gripping your hips to guide you on his cock. your head tips back again as you moan his name. his mouth finds your throat again leaving punishing kisses and love bites along it as he thrusts deeper into you. Your hand tugs on his hair eliciting another moan from him. One of his hands finds its way in between your bodies, his thumb going in between your slick folds to circle your clit applying gentle pressure. you can feel the pressure build in your stomach again your thighs clenching around his. he can feel the way you clench around him and he captures your mouth with his wanting to swallow and own every moan you make. your moans get louder, more filthy, and carless
"f-fuck sam" you moan into his mouth, sam presses more deliberitly against your clit applying just enough pressure trying to make his name slip from those pretty lips again.
"Sam, m close" you moan loudly feeling your stomach coil tightly, your legs tensing your walls begining to flutter around his cock
"mhm I know baby, let go f'me" Sam coos softly into your ear rolling his hips in a practiced rhythm and planting soft kisses along your pulse point. he can feel himself getting close too, as your walls perfectly encase his length squeezing him just right
his thrust becomes sloppier and messier as you come undone, crying out his name as your hips stutter on top of him your pussy clenching around him. Sam helps you ride your high out guiding you with his hands as he follows soon after his head tilting back with a groan as he releases inside you, his warmth filling you.
your head falls on his shoulder both of you spent. you sit there for a while before you can feel Sam place a soft kiss on your head stroking your hair with his hand "Did so good baby, so proud of you" he whispers into your ear. you fail to muster up a response so you just nod.
he lifts your head with his hands holding your cheeks gently "Is it too early to say I love you? Because I think I do" he says as he smiles at you with the most adoration and loved filled eyes
"no, I don't think so, 'cause I love you too" You smile down at him leaning into his touch and planting a kiss on the palm of his hand. he pulls you closer to him snuggling you and running his hand up and down your back gently, he wanted to stay here forever, never wanting to let you go again you were his now, no one else's. oh and um thank god for tinted windows
7 yaps: um hey guys so um... I'm back with a bang (literally) I've been crazy occupied as of late and have had literally no inspo to write but I finally decided to finish this wip. fair warning this was my first time writing smut ever so I'm sorry if it's not good and please give any feedback. this also went way far off the rails for what I was originally envisioning but don't blame me blame the friends who encouraged it. I really hope yall enjoyed tho and it wasn't too painful to read
P.S. Not proofread
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