You stood in the chilly doorway, shivering in your denim jacket and skirt as you waved goodbye to the little blonde toddler sitting on the couch.
"See you next weekend, Emma!"
You watched her chubby little hand wave you goodbye, and then spoke your farewells to Emma's uncle, Sam, as he shut the door behind himself and Emma. You smiled up at Emma's father, Mr. Winchester.
As the both of you walked back towards his car, a beautiful Chevy ‘67 Impala, he told you, “Emma loves you, y’know. Says you’re the best sitter she’s had.”
Your cheeks warmed at the compliment, and as he opened the door for you. “I love Emma! She’s a wonderful child, you did a really good job raising her, Mr. Winchester.” You climbed into the car, letting out a small Brrr sound as the cold leather chilled the skin not covered by your skirt.
There was a small thump as he got into the driver’s side and slammed the door shut, and then he turned to you and gave you a smile. “You can call me Dean, kid.”
You tried to ignore how heat crept up your neck and ears at the way he looked at you, and instead nodded.
He looked at you for another moment, just to say, “It isn’t just Em that likes you.”
You couldn’t look at him, not when your face had turned as pink as it had. You kept your gaze locked on your legs, bare and silky from shaving that morning, and hoped that your hair covered his gaze from catching how hard you were blushing. Quietly you murmured, “I like you, too, sir.”
It felt like you jumped three feet into the air from your seat when he put one of his large, calloused hands on your thigh to rub soothing circles.
You looked at him with wild eyes, panicked, but his face was painted with a gentle expression. “I told you to call me Dean.”
You watched as his nostrils flared and his lip twitched in one corner, curving up.
He kept his eyes on the road, but continued talking. “How old are ya again?”
Playing with your fingers, you replied, “I just turned 18.”
He hummed. “I notice you got a pretty little ring on your finger. Did your boyfriend give ya that?”
Your face, which had been red for so long, suddenly paled. “No! I’m not allowed to have a boyfriend.”
Dean looked at you, stunned. “Not allowed? That mean you’ve never had one?”
You shook your head, your hair falling atop your shoulders. It felt like you had been paralyzed, you couldn’t move; Your entire body electrified, burning up like a furnace, and the source of the heat was the hand wrapped around your thigh. You struggled to regulate your breathing.
“Yeah?” You cursed yourself at the sound of your breathy, high voice.
“It’s nice havin’ you around.”
You couldn’t help the smile that split your cheeks, and before you could second guess it, you laid your small, warm hand atop his, and said, “It’s nice having you around, too, Mr. Winchester.”
He didn’t correct you on the formal name, perhaps he realized he was beating a dead horse, but instead just smiled and rubbed your leg again. You couldn’t help the way your breath hitched, and your legs pressed together, catching his fingers between them. You tensed when those very same fingers spidered up your inner thigh just the tiniest bit.
His eyebrows raised. “You okay?”
Coughing, you nodded, spreading your legs back into a comfortable width. He shrugged and looked back at the road. You tried not to notice how his warm hand stayed there, right between your legs, at the top of your inner thigh.
You knew Mr. Winchester’s wife, Lydia, had died when Emma was just a baby, and how hard it had been for him. You babysat Emma on the nights he had tried to get back into the dating field, going out with Lisas and Cassies and anybody who complimented his car on Tinder. You pretended not to notice the smell of perfume and the sad look in his eyes he tried to mask- you knew not to ask how the night went when he came home. It wasn’t that Mr. Winchester was an ugly guy- with hazelnut hair and sparkling green eyes, and the ability to charm anybody’s pants off, he wasn’t going home lonely and sad because he was getting rejected by all of his dates, but probably because he was doing all of the rejecting- because no woman would ever be like Lydia. Although he was touching you and smiling so sweetly and making your insides feel like they were replaced with jelly, you knew he wasn’t interested in you at all.
You watched as he turned a sharp corner, and couldn’t help the butterflies that erupted in your stomach when he gripped your thigh tighter. Some classic rock song played quietly, and you couldn’t help but just... stare at the man before you.
His nose was long and straight, and you couldn’t help but notice the curve of his plump lips, and the length of his lashes. Suddenly, it felt so hot in the car. Your hand reached down to turn the heater off, only to see it wasn’t on.
You chuckled uncomfortably. “Yeah, just a little.”
Mr. Winchester said nothing and you watched him crank the manual window down, allowing cool air to rush in and lick soothingly at your burning skin.
It was silent for moments after that, and you noticed how your gaze kept drifting from Mr. Winchester’s face-the sharp curve of his jawline and the horrifying realization you would kill to know what his stubble would feel like grazing your smooth cheeks as he kissed you softly- and his huge hand, still perched upon your naked thigh like it was just second nature to touch you- you blushed as you thought about how his hands would feel touching you everywhere. You wondered if you being all-too-obvious that you were gawking at him like a creep, when he laughed.
“I can feel you starin’, sweetheart.”
You felt like all the blood had been drained from your body. “Staring? Oh, I haven’t been staring!” You couldn’t help but pause. Sweetheart.
Another laugh came out, this time softer, and he gave your thigh a small squeeze.
“How’re your folks?”
“Um, they’re good. Yeah, they’re good. I’ll tell them you asked! They always ask about you at dinner, they say you’re really nice, sir. You should pay me more, though, they think.”
Your jaw dropped as soon as you realized what you had just said.
“Oh my word, Mr. Winchester, I am so sorry. I didn’t mean to say that. I don’t think you should pay me more, really, I’m happy with the amount you give me already! I’m grateful you even pay! Oh, gosh, please don’t fire me, Mr. Winchester.”
Dean was unfazed. He gave your thigh another squeeze and just smirked. “Pay ya more, that so?”
You gulped. Yep, you were getting fired.
His hand left your thigh to spin the wheel. You immediately felt the absence, it felt so cold now that his hand was gone. Tears stung your eyes- you were getting fired, and Mr. Winchester hated you. You watched the hand that was on your leg close around the stick shift as he pulled over to the side of the road and parked on the gravel.
You watched in slow motion as his head turned towards you. His eyes, blazing green and so bright, locked on you. You felt minuscule and tiny under his gaze, and you squirmed uncomfortably.
His hand reached out to tuck a curl behind your ear, and his eye caught on your little earring, glimmering in the car’s soft lighting.
“You like me, right, Joanna?” he asked. You noted that there was something odd in his voice, a hesitancy, a caution maybe.
You nodded hard. “Yes sir, I like you very much!”
He nodded as well. “Well, I like you, too.”
“Thank you, sir.”
He leaned in, just a little, just enough to make your heart stop. “I’ll tell you one more time, please call me Dean.”
You nodded your head. It felt like you couldn’t speak, or breathe, or move, not when he was so close you could taste the mint on his breath, or when he smelled like leather and aftershave and the woods.
He kept leaning in, his body twisting so he faced you, and you finally realized what was happening.
“Dean-,” you gasped.
“It’s okay, kid.”
Then he leaned in all the way, tilting his head slightly so that his lips could catch on yours. You knew what to do from movies and friends and teen magazines, so you opened your mouth just slightly to slot it with his, and you swore you died. His lips were unbelievably soft and plump and his teeth were catching on your bottom lip and it felt like you were being electrified or shot by lighting or tased or all of the above all at once. He fumbled with huge hands to unbuckle his seatbelt as he kept your lips pressed to his, swallowing all of your gasps as you did everything for the first time. Every time Dean pressed his mouth deeper into yours, his tongue flicking the corner of your mouth, his teeth sinking into your bottom lip, his fingers digging into your hips, it was the first time for you.
And then, he pulled away.
You tried not to let your face settle in an unhappy frown. You didn’t try hard enough. Dean chuckled, and grabbed your chin, giving you a quick, hard kiss on the lips. You heard him mumble my grumpy girl.
“How’s that for a pay raise?”
Your face went red again, and Dean rubbed your hot cheek.
Leaning into his touch, you asked, in a voice barely above a whisper, “Was that okay?”
His expression turned confused. “Yeah, of cour-. You’ve kissed before, right?”
You wished you could sink into the leather seat, and you tried your hardest to- raising your shoulders into your chin and lowering your chin into your chest.
“I’m guessing that’s a no. Really? Never?”
“I never wanted to,” you mumbled. “Before I met you,” you added quickly.
Dean laughed, his eyes and nose crinkling with it. Both hands rubbed your thighs.
“You really are cute.”
You gave a pinked shrug and leaned in again for another taste of his lips.
“Woah, slow down, baby.”
Dejected, your shoulders slumped and you nodded.
Dean noticed how defeated you looked and gave your thigh a familiar squeeze. “No, c’mon. Don’t be sad. I just don’t want to take advantage of you. You’re just a kid.”
Your jaw dropped for the second time that day. “Just a kid? You just kissed me!”
Dean was quiet for a moment, his gaze on your flushed skin. You only just now noticed that your skirt had been pushed up your thighs, and your jean jacket had been rumpled. You couldn’t believe him. He had you calling him by his first name like an adult, touching you all over like an adult, kissing you like an adult, and then he had the audacity to call you a kid?
“If at any time you don’t want to, you tell me no, okay?”
Unsure, you nodded. “Okay.”
“Get in the backseat.”
Your heart leapt with joy. More kissing?
Unbuckling your seatbelt you began climbing into the spacious back.
Dean gave a dark chuckle from behind you. “You always babysit my kid wearin’ panties like that, sugar?” He asked, a large hand reaching out to grip the exposed globe of your ass.
You were taken so aback by the touch that you fell right onto the long backseat, your skirt flipping up and revealing a pair of lacy white underwear covering smooth, hairless skin awaiting the touch of Dean’s fingers.
Pulling your skirt down and blushing, you mumbled, “I’m sorry, sir.”
Dean hummed. “Perhaps you’re dirtier than I thought. I thought you would wear cotton, baby blue maybe.”
You watched excitedly as his long limbs climbed from the drivers seat and into the back with one knee on the seat and a leg outstretched along the floor, settled so he was looming over you.
He pushed your skirt back up, his hands trailing the expense of soft skin. “God, I’m so glad you didn’t wear your little Days of the Week panties. Yeah, I know ya got em’” he added when he saw your shocked expression. “Can’t wait to rip these off you.”
Your cunt clenched painfully at his dirty words, words you were hearing for the first time, and gave a small whine.
“Be patient, princess.”
You nodded, wanting to be good for him, so you stilled your bucking hips and silenced the tiny whimpers that poured from your lips.
Heavy-lidded green eyes peer up into yours, and he gives a, “yeah?”
He’s looking at you like you’re something to eat, his lips catching on his teeth, and his tongue lolling out to poke at his lips, and his eyes all heavy and trained on you. The fire of it made another wave of heat curl up inside your stomach and lick between your thighs.
“Are we going to kiss some more?” you ask. “I really like kissing you.”
You swear you saw his eyes turn darker. “I think,” he said slowly, drawn out. “We’re gonna try somethin’ different.”
This piques your curiosity. “Different how?”
You can’t help the loud moan that pierces the quiet atmosphere of the car when you watch him spread your long legs and settle between them. His fingers settle at the hem of your panties, and he looks so hungry, like he’s just waiting for your permission so he can tear them off you like an animal.
“You like kissin’, right, baby?”
“Yeah,” you smile. “Your lips are soft.”
He chuckles. “Well, hows about I kiss ya again, but... somewhere else.”
You hum confusedly. You don’t really understand but, you trust Dean. He wouldn’t hurt you.
You smiled. “Okay.”
“It’s gonna feel real good, baby. Am I the only one that’s seen ya like this?”
It feels like you can’t stop blushing. “Yeah,” you whisper.
“Good,” his voice comes out like a growl and it almost makes you cry out.
He drags your panties down your legs slowly, and you watch his face the entire time. You spread your legs a little wider and angle your toes downwards so that the garment won’t catch on your white Converse. When they’re off, Dean throws them down onto the floor, near his foot, and looks at your face for a moment, and you imagine what he’s looking at. A small, pinked girl with big, curious brown eyes and matted sooty lashes, her round mouth swollen from an older man’s kisses. When he spreads your legs further, the first thing you feel is his probing fingers. He reaches out to touch, his fingers meeting the apex of your thigh and rubbing the dripping slick around there, making you cry out.
“No, baby, shhh. How’s it gonna look if a cop drives by, hmm? Sweet little girl spread out in my backseat, a dirty old man between her legs. You gotta be quiet, sweetheart.”
You nodded, a little embarrassed. Soothingly, Dean gave a little kiss to your ankle. He spread your legs a little wider and, finally, his gaze dropped between them. He let out a loud groan when he saw how wet and flushed your soaked flesh was, and his fingers, which were still on your inner thigh, moved just a little to rub at the bottom of your slick hole. If he added a little pressure, he was sure his digits would just slip inside you. You had to bite your lip to stay quiet like he asked.
“You smell so good,” he whispered, and you giggled shyly, nervously, when you heard him inhale.
You watched his back muscles flex as he maneuvered his body so he was kneeling, with his face just mere inches from you.
Suddenly you were wracked with nervousness. Were your parents wondering where you were? And then that nervousness was washed away; Dean said you would feel good.
“Are you going to kiss me now?”
Dean gave an Mmhm noise and kissed your inner thigh. “If you don’t like it, don’t be scared to tell me to stop.”
You nodded, and waited, watching him, your skirt around your waist and your jean jacket still on. He kept his eyes on your face as his wet, pink tongue poked out and experimentally licked through your folds. You jumped a bit at the contact and winced when you felt your nails bite the pristine car’s leather. When you didn’t tell him that it was horrible, you hated it, and to stop, Dean tasted you again. He dipped his tongue and licked right up your entrance, where you kept dripping and the taste was most potent. A small whimper bubbled out of you.
“You’re not kissing,” you whined.
Dean smiled and then ducked his head. You couldn’t see what he was doing. You felt his pouty lips seal around your clit and suck, making your body bound up and your hands began their search for anything to grip onto. Dean offered his hand to hold, you readily took it, holding on while he introduced your body to sensations you had never felt before. He began licking again, thick laps up and through your lips, his tongue circling your bud.
His mouth lowered to suck your lips into his mouth and he looked back up at you, trying to gauge your reaction.
“Dean,” your voice was so high pitched and shallow you felt Dean smile against you.
His chin was glistening with you.
“I think... I think that I want you to be my first,” you whispered.
Dean sat up, wiping his chin with a flannel-clad forearm, and squinted, trying to see if he’d heard you correctly.
“I’m sorry. What?”
“I want to do it... With you.”
Dean gave you a sympathetic look, and he leaned down to peck at your lips. “You don’t have to,” he whispered gently. “Don’t feel like you have to.”
“I don’t! I want to! I’ve always really liked you,” you looked up at him through your lashes. “I tell my friends about you.”
Dean smirked, and then he pounced, his big hands tickling your sides. “What’dya tell ‘em, kiddo?”
You laughed, out of breath with the way his fingers were shaking at your ribs. “I tell them that I think you are really cute, sir, that I think about maybe being with you when I’m old enough.”
He kissed your nose. “Sweet little girl.”
You blushed and leaned up into his lips, cupping his bearded cheeks with little hands. “Want you to be my first. You’re the only boy who’s ever been nice to me.”
You heard his belt click and clack. “Oh honey, I’m not a boy. I’m a man.”
Your face reddened again and you nodded, slowly taking off your jean jacket. You couldn’t believe you were about to lose it to the man you babysat for. Dean peeled your tank top off and pressed your lips together again. His skilled fingers reached behind you to unclip your bra. With the driver’s side window still cranked open, the chilly air bit at your exposed skin, causing little goosebumps to erupt and your nipples to pebble. As you began to shiver, Dean soothed your cool flesh with his large, warm hands.
You subconsciously keened into his touch, wanting him to continue the rough drag of his calloused digits.
Dean gave a quiet chuckle, "Such a needy little thing, aren't'cha?"
You only nodded, instead replying, "How come you're fully clothed?"
Dean hummed, and you watched thick fingers begin to work on small brown buttons as Dean slowly revealed his smooth chest and the toned expanse of his stomach. He looked up through thick lashes, and you nearly melted, feeling those pretty green eyes on you as he watched your face to gauge a reaction. He slid the plaid garment off his arms, letting it drape on the leather backseat. As you watched him begin to unbuckle his belt, it suddenly became so hard to swallow, to breathe, with the sudden molten heat between your thighs. You listened and watched intently as his belt clicked open, and you watched the shimmy he gave as he pushed them off his curved legs, revealing a pair of snug boxer-briefs that hugged his thighs and revealed an aroused tent in the crotch. Dean looked at you expectantly, and you gave a quiet little, "please", so quiet Dean wouldn't have caught it if he hadn't been watching your lips so closely.
"You're sure this is what you want?"
You nodded fast. "More than anything."
Dean hovered over top of you and you couldn't help the pathetic buck of your hips as you tried to meet his, tried to feel him. His plush lips met yours, and you savoured the rough drag of the chappedness against your smooth. He began to kiss you a little rougher, his teeth starting to bite down on your bottom lip hard enough to draw blood, making you cry into his mouth. You gasped loudly and furiously tried to rub against Dean's thick thigh when his soft tongue began to lick inside your mouth. It felt foreign, but so, so good. Your leg came up to envelope his waist and your hands found his broad shoulders, your fingernails gripping and digging into the bared skin slightly as he sucked your bottom lip into his mouth before letting it pop back into place. He sat up as far as he could, ducking his head so it wouldn't hit the roof of the Impala, and stared down at you as he pulled his briefs slowly down his legs. You couldn't help your eyes from following the movement, or the desperate whine that erupted from your lips as he shucked his boxers to the ground, revealing himself to you. He wasn't insanely long, but it was still bigger than anything that had ever been inside you, with a girthy width and a flushed, pink head that was shining with pre-cum.
He watched your reaction. "You're so fuckin' pretty," Dean breathed. You wanted to reply, wanted to say thank you like the polite girl you were, show him your manners, but you couldn't find your voice. You couldn't look away from the thick dick about to take you.
'Hey, hey. Eyes up here," Dean jokingly chastised, and you laughed, finally looking up,but when you saw Dean's face he was nervous looking. His lower lip was worried between his teeth, and his eyebrows were furrowed. You sat up, gently touching a scar on his arm.
"What's wrong? Did I do something?" You murmured the last part gently, like you were already preparing for him to throw your shed clothes out the window, sending you walking home, while yelling out a snarky comment about a pay raise as he drives away.
Dean's expression instantly softens, and he reaches out to palm your cheek. "You're old enough to be my kid, baby."
"I don't mind! I like that you're older, sir."
The added title at the end makes him groan, and he bites out a, "Yeah?" as he pulls you onto his lap. You feel his cock brush your inner thigh, so deliciously close to your pussy, you can't help but let out a small cry.
Your breathing is labored. You're so close like this. You can feel his everything, but you want more. You rest your head on his shoulder, his skin like a furnace, and slowly you slide the delicate ring off your finger. “I notice you got a pretty little ring on your finger. Did your boyfriend give ya that?” And gently, you pry open his heavy hand, and place the petite ring inside, curling his fingers around it. He gives you a confused look until he realizes. It's a purity ring.
"You're such a sweet little girl," you shiver when his stubbled jaw grazes your neck, his lips right by your ear.
Your head tilts back to allow him more access. "I want it. Please, Dean," you whisper. Quietly he swears and gently rocks you along his length, a firm grip on your hips. You dip in and give him a chaste kiss on the corner of his lips, begging another soft plead.
"I'm gonna fill ya up, sweetheart. Get you nice and full."
Then he reaches behind you, and you can feel him grip his dick. He lets it slap against your ass a couple times before he slowly pumps in and out of his fist. "It might hurt a little, okay?"
You squeeze your eyes shut and prepare for pain,but nothing comes but Dean's gentle voice.
"Lay back, honey. It'll be easier on both of us."
You nod and do as you're told. The leather is chilly from the cold air whooshing in from the slightly cracked-open driver's side window and you shiver.
"It's okay. I'll make you feel so good. You trust me, right?"
Of course you nod without hesitation, without apprehension. You'd do anything for Mr. Winchester. He grunts out a good, and then you feel his blunt head dragging across your pussy lips. One of Dean's big hands positioned above your head, his head hanging above you, watching for any discomfort. Your hands wrapped around his shoulders, one coming to rest at the nape of his neck where your fingers entertained the short hairs there.
"You feel so good already, baby. So warm."
"Please. I can take it."
Dean said nothing, but smiled and rolled his eyes, guiding himself to your entrance. Finally obliging, he began to thrust his hips forward to sink into you. Barely an inch in, and Dean felt like he was going to die. You were so tight around him already, so warm and wet. For him. It felt like heaven. You stayed quiet, your teeth worrying your bottom lip so hard you thought it would split. Dean held your hand as he continued to bottom out. Tears welled up in your eyes, and you weren't sure from what. Pain? Pleasure? Foreignness?
"Relax for me, dollface. You're squeezin' me so tight."
Taking a deep breath, you open your eyes. He's still watching you, and he gives you a little smile. You return it, and its heartfelt. He's so beautiful like this. Tanned skin glistening with sweat and a heaving, broad chest. Green eyes, even in dim lighting, twinkle and shine like a Christmas ornament. His lips are bitten and swollen with your kiss, and his hair is disheveled and mussed from your hands. You think you could fall in love with Dean, if you haven't already. He plants a heavy hand on your cheek, the hand that was on your hip, and you think you're mush when his thumb brushes your lips. Shyly, you open your mouth to suck gently on the tip of his finger, looking at him. Dean smiles a little, his tongue peaking out through perfect teeth, as he dips his head down to nestle into your neck, breathing hard as he begins to gently pump his hips. The fire in your stomach intensifies, never having felt so stretched out, so full in all your life. Your nails dig into his arms, feeling the toned muscles there flex in your grip. You whined on every push in and out, a mix of feeling uncomfortable, but not wanting to stop.
"Sweetheart, you gotta relax for me," he whispered soothingly, kneading the softness of your hip. When you couldn't open up for him, still tightening on his thick cock and whimpering, he pulled his hand off your hip and moved to rub softly at your clit. You gasped immediately and Dean quickly took this as an invitation to buck into you. Biting down on his shoulder you tried to stifle all of your moans and screams. Dean sat up a bit so he could grip your hips with both hands and bring you down on his dick.
Noticing your whine at the loss, Dean murmured, "Rub your clit, baby," with a nod directed between your legs.
Your eyes rolled back and your body began to shake as you reached down to circle the sensitive little bud. Your noises were wanton and needy, high pitched and loud. You couldn't bring yourself to be embarrassed.
"I want you to cum while I'm inside you. Want your first one to be with me."
You couldn't do anything but nod as he fucked you breathless, the stimulation so much you couldn't even touch yourself anymore. Suddenly, Dean's greedy mouth was on your neck, gently nipping and sucking on the thin skin, breaking blood vessels beneath. Delicately he sank his teeth in, making you scream out, but he only soothed the mark with his warm tongue.
"Please no marks," you breathed. "Not ones people can see- my parents will see."
Dean growled. "Don't care. Parents think I'm cheap anyway. I want them to know you belong to me," he nosed at your jawline, his mouth right next to your ear. "I want you to go home, covered in my mark, and I want your father to know I'm your daddy, too."
You did nothing but whine, letting him continue his assault, your hands in his hair as he ravages you.
"Gonna go a little faster, yeah?"
You made an Mmhm noise, closing your eyes and breathing in his aftershave. Dean suddenly slipped out of you, and you keened at the sudden loss, to bunch his discarded flannel up underneath your hips, elevating them for him. He slid back into you and resumed a much faster, deeper pace, the sound of skin against skin resonating throughout Baby.
He breathed heavily into your neck, nipping your earlobe while grunting out,
"You like this?"
Your eyes clenched shut, rabidly scratching at his back as you let out dry sobs.
"I like it, Dean. S-shit. I love you. I love you so much."
Dean had no idea if you genuinely meant it, or if he was just dicking you that good. Dean nodded, and kept the quick pistoning of his hips. "It's okay, baby."
You kiss him again, not moving your lips, just pressing them together as Dean pulls out and thrusts back inside.
"Mmph-" he moans into your mouth, you held him tightly against you, pressing up into him as your body continually works to accommodate him inside you. You make sure to keep your bodies pressed tightly together, wanting to feel the beat of his heart against yours as you burrow your face in the pulsing heat of his throat.
You can imagine how tight you are on him, and you try to envision what it must feel like for him. Hot, velvet walls surrounding his dick as he thrusts deep inside, about to cum.
"Need you to cum for me, honey,"he encourages. His hand slides down again between the junction of your thighs, his thumb rubbing quick, precise circles into your clit. It felt like being electrocuted, your body full of jolts and shocks and shakes connecting your body to his. You struggle to keep your eyes open for any longer, screwing them shut and searching for something, anything, to grip onto, to anchor yourself. Dean offers his free hand, lacing your fingers together while you squeezed tightly for purchase.
"Ple-please. It feels so funny- I've never felt anything like this before."
Dean gives a dry chuckle, his voice gruff. "I know, kid. It's okay, just let it happen, I got you."
You kept babbling, gripping his hand as tight as you could, a coil in your lower abdomen tightening and this blinding white heat burning until finally-
"Oh my God! Dean!"
Your hips bucked up and with every intense wave of pleasure, you felt yourself clench down on his dick, your body racking up into his solid chest. Desperate pleas of fuck and please left your mouth in an endless stream that Dean shushed with sweet kisses to your dry lips and wet cheeks. Through the haze you could feel his hips stutter, and his dick twitch in you. He kept rubbing you, pumping deep, until you finally came down, your body struggling for a breath, your hair a mess, a content sigh leaving your lips.
"You did so good, sweetheart. You were such a good girl," he whispered, kissing your sweaty hairline and nose.
You gave a lazy smile, leaning up into the touch. "I want to make you do that, too."
Dean shushed you, petting your hair and smoothing it down. "It's okay, baby. I'm okay, you don't have to."
"Please? I want to try tasting you, like how you did to me."
Dean's eyes narrowed, and he swallowed back a groan. "Lean your head down."
You sat up up on your knees, craning your neck so that it was almost laying on Dean's lap, your face right by his dick. It looked so pretty up close, a red tip, and a vein on the underside that you wanted to lick. There were faint freckles littered all over his stomach, and you gently ran your finger over them. "You're so pretty, sir," you mumbled softly.
"You're pretty too, baby. Just stick your tongue out."
So you did, opening your mouth wide and poking your tongue out of your mouth, trying to look up at him for approval. From your peripheral, you could see a heavy fist grip the base of his cock and pump fast. He warned you he wouldn't last long.
The head was dripping small white beads, and so you leaned in, licking one off.
"Mm god, do that again."
So you did. You'd do anything he asked. You flattened your tongue and pressed kitten licks and small kisses to the tip of his dick until he gave a low growl that he was going to cum. He watched his freckled face turn pinker and his fist speed up before he was painting your tongue with heavy ropes of thick white. He didn't tell you to swallow it but you did anyway, and he held you close for a long time after that.
You laid together in the backseat of his car until the fog melted off the windows, until you were reminded you had a home and parents to go back to, until Dean told you he had a baby to put to bed and a brother to thank for watching his kid while he fucked the babysitter. Then, he dressed you, slipping you back into your rumpled skirt and jean jacket, and tucking your panties into his pocket as he got redressed too.
He held your hand as he drove, kissing you gently at stop signs and red lights, and when he dropped you off at home, you stood outside the car, your head poking in as you leaned into the rolled-down passenger window, mumbling, "Goodnight, Mr. Winchester. Thanks for driving me home."
And he smiled. "No problem, kiddo. Tell your folks I say hi."
"I will, sir."
And you turned around to walk to your doorstep, and Dean called out, "I need a babysitter this Friday night!"