DBF!DEAN WINCHESTER made it his life’s job to take care of you. He made sure you were comfortable and safe whether you were with him or not. The usual tough and disconnected man always softened whenever he was with you, his love for you overpowering any coldness inside of him. His rough calloused hands ran softly through your hair, adjusting your skirt and shirt to keep you covered up to prevent anyone else seeing what was his, his fingers gently trailing down your waistband under the table when he got impatient. He didn’t care if it was seen as immoral or wrong to date you, but you couldn’t stay away from each other if you tried.
DBF!DEAN WINCHESTER was completely smitten by you the moment he met you. You had graduated college and came back home, the familiarity of the house you grew up in and the new people and adjustments your parents had met and made was foreign to you, but they weren’t all unwelcome. It took months of back and forth pleading looks and careful yearning lingering touches of fingertips for the two of you to realise it went both ways, and the taboo relationship felt right and safe, especially the nights you lay on his chest in comfortable silence, sharing soft words and happy memories.
DBF!DEAN WINCHESTER felt guilty to be the one to take your innocence, but on the other hand, a twisted, protective part of him was glad he was the only one to take you like that. His soothing fingers and hummed praise, your soft legs and self indulgent whimpers, the silk sheets and the familiar walls of your bedroom, made the most perfect night for you and Dean. The softness of his lips trailing down your stomach and over your hips with experienced precision made your cheeks flush and stomach flutter, making you certain you wouldn’t want this moment with anybody else.
DBF!DEAN WINCHESTER FICS - missing you while he’s away
oh nothing, just laying here and thinking about dbf!soldier boy who absolutely HATES any boy you bring home. (how is he supposed to let someone parade around with whats his hm!)
*rearranging ur guts*
"see you don't need a boyfriend when you got me sweetheart."
⟡ CW! SMUT - masturbation (m & f), age gap (not really mentioned), phone sex/on video, pet names
⟡ LILITH YAPS - i hope this makes up for the lack of posts the last day or two! also do we fw the new one shot style? not proofread, lmk about any mistakes i can change <3
masterlist ⟡ request something ⟡ join my taglist
Your phone pinged on your bedside table, the message notification ringing through the bedroom. Looking at your home screen, you saw that it was a message from your dad’s best friend who was also your boyfriend, Dean Winchester.
Better yet, a video.
’Weird’, you thought to yourself. He’d only been away on a trip for a day, and he usually called you whenever he arrived. He must’ve gotten to his motel early.
You figured maybe it was a video of him showing you around his room, he loved to make it feel as if you were with him even when you were miles away.
You picked up your phone with a soft smile tugging at your lips, thinking about what you were about to click into.
The video was captioned ‘For my girl. Miss you too much to wait.’
As you clicked into it, the heat immediately climbed up your neck and painted your cheeks a light pink.
On the screen in your hands, Dean was holding his thick cock in his hand, stroking it teasingly slowly, squeezing at his leaking tip.
“Hi, angel.” His voice was gruff and thick with lust, almost sounding sheepish at the way he was recording this video.
The sight of him so pent up and aroused made your thighs squeeze together as a familiar heat grew between your legs.
Your mouth watered at how he pumped himself roughly, the impatience and desperation dripping from the grunts he let out just out of the camera frame.
As he squeezed a fist around his cock, rutting his throbbing length into it like he was using a flesh light, all he thought about was you. He imagined it was your tight pussy clenching around him, pulling him in so deep you could feel him in your lungs.
“Fuck.. Wish it was your sweet pussy. I miss how tight you squeeze around me.” He grumbled, his hand moving increasingly faster over his cock. The way it twitched underneath his fingers was something you’d almost learnt off by heart by now.
You knew he was close already. He always came quickly when it came to you.
Despite the fact both of your parents were just downstairs, you slowly slipped a hand down your shorts, teasing at the soaked fabric of your panties the way Dean would.
From the sound of his low groans on your phone and the taboo sight you were looking at, you felt close already yourself.
The need for him to be there beside you, his cock thrusting deeply into your cunt rather than his hand, his fingers groping at your nipples before he lapped and sucked on them to soothe the dull ache.
“Dean..” You gasped under your breath as you sunk a finger into your dripping hole, eyes glued to him stroking himself furiously on the screen.
A few moments later, he was done. His thick length twitched in his hand before shooting hot spurts of his cum onto him, his laboured and ragged breath broken into a relieved groan.
When he panned the camera upwards, you got to see his flushed face and stupid fucked out grin. The sound of him doing his jean zipper and his belt clinking sounded faintly underneath him before he spoke.
“I hope you’re touching yourself right now, darlin’.” He spoke directly to the camera, a teasing knowing glint in his eye.
You bit the inside of your cheek, feeling called out and ashamed of how predictable you were in this situation.
“‘M gonna show you what we’re both missing when I get back, ‘mkay?” Dean continued, his expression more serious and promising this time.
After he speaks those words, the video ends.
You take a minute to collect yourself, your own fingers still moving slowly inside of your clenching cunt.
With one hand, you type something back to him in response to the video.
W: Use of petnames, Biting, Unprotected pinv (wrap it before you tap it), dean being dean, oral (f receiving), DBF!Dean, Age gap (reader is 20, dean is late 30’s), Angst, Hand kink, Creampie, Size kink (if you squint), I think that's it!
A/N: Dean would be such a girl dad you CANNOT change my mind. I'm a Dean girlie so I feel like it's easier for me to write with him opposed to Sam. That being said, I hope you enjoy this. I had a blast working on it.
A/N2: I posted this, no joke 30 minutes later i was in an ambulance 🥴
part two
You had just gotten off of work. Your 9-5 has drained you. Same papers, day after day. If you were honest you could have just skipped dinner, and went to sleep. God knows you need it, but here you are.
Walking into the grocery store to pick up a few things for a quick dinner. Deciding to roast some chicken, you stopped by the produce to pick up a few odds and ends for your lunch the next few days. While you were scoping out the best cantaloupe to buy, brown pigtails adorned with pink bows came into your vision. The little girl tugged on your blouse, “I think I lost my daddy.” She mutters shyly. Immediately dipping down to a crouch you tried to comfort her, “Well sweetheart what does he look like? Where did you see him last?”. The girl, who couldn't have been more than 6 years old, began to describe her father to her best ability. During the little exchange, her father came from the chip aisle, seemingly anxious. He breathed out in relief when he finally saw her again, “Babygirl where did you run off to?” He picked her up, setting her in the cart. “I wanted strawberries, then you were gone.” She pouted, “Sweetheart we could’ve gotten you strawberries you just have to ask.” he looked up from the girl to you, “Thank you so much, I’m so sorry.” You smiled at the man, “No problem she wasn’t a bother.” looking down to the girl you smiled again. He thanked you again and you both went about your shopping.
That night in the midst of making dinner, he was all you could think about. You didn't even know his name yet the thought of him consumed you. Dinner was silent that night, the sounds of your fork against the ceramic, too caught up in your thoughts to turn something on. You went to sleep later than normal, since you had opted to make food instead of ordering out. Your wallet needed a break, and so did your stomach.
---
Traffic was bad the next morning when you left to go to work, just what you needed. You were already running late due to your phone being dead. No phone = No alarm. You were finally able to clock in, sliding your card through the scanner to get in. Dull boring day was going by like usual when you got a call from your dad, “Hey is everything okay? I’m at work.” The man sighed over the phone, “Yeah sweetheart are you off tomorrow?”. He sounded happier than usual. Odd. “I can be, what’s up?” you questioned. “Nothing, just me and a buddy of mine going fishing tomorrow.” You relaxed as he spoke, “Okay this relates to me how?” You asked. “Well his babysitter flaked on him so he needs someone to watch his little girl.” There it was. You began to realize the relation. “So this is you calling me to ask to babysit?” You sighed into the phone, “C’mon honey it’s the first fish of the season.” He begged into the speaker. “Fine, but you totally owe me.” You reluctantly agreed. “Love you too pumpkin.” He hung the phone up, pleased. You slumped into your rollie-chair. Before you clocked out that night, you were sure to brief them of your absence, despite your affliction.
It’s not that you didn't like kids, truth be told you couldn't wait to start a family. It’s just you haven’t had a day off in over a month and here you are using it to babysit one of your father’s friend’s children. Maybe it won’t be that bad, you thought.
You woke up around 6am, the same as always. Only this time you were switching blouses and skirts, for sweats and a t-shirt. After showering, you got dressed in a simple black pair of sweatpants and a Led Zeppelin t-shirt. Thinking nothing of it, you threw on your red converse and headed out the door. The drive there was peaceful. Slow easy Saturday morning. Fog covered the road in a thin haze. Despite your gps failing halfway through, you had gotten it to boot back up and continue to give you directions.
Pulling up to the house it was beautiful. Gorgeous white house with a wrap around porch. Adorned with an American flag hanging from the banister. Charming baby blue shutters hung by the windows. This wasn’t just a house, no this was a home. Pulling up into the driveway, you are met with a familiar sight. Your father’s red Ford pick-up, parked right next to an intense black Chevrolet Impala. Parking a bit off to the side, you grabbed your bag and headed to the front door. Chatter muffled behind the door as you knocked. Your father was quick to greet you. “Sweetheart you made it! Come in.” He slid to the side and ushered you inside the home. “This house…It’s so beautiful.” you muttered, setting your back on the table by the door. “I helped build it, a long long time ago.” Your father smiled at the reminiscence as you both walked into the kitchen. An oddly familiar voice shouted from atop the steps, something directed at your father. Where have you heard that voice before? God it felt like it was on the very tip of your tongue and you couldn’t spit it out for the life of you.
Heavy boots stomped down the steps followed by a softer pair of slippered-feet. As the figure came into view, it felt like the wind was knocked out of you.
That’s where you knew him from.
“Nice shirt.” Was all he could mutter, sporting his signature grin. You smiled back, as the blush creeped from your cheeks to the tip of your nose. With no makeup on was a hell of a way to greet the man that consumed your thoughts. It also made it harder to hide the attraction slapped across your face. “Thanks, small world.” Was all you could find. Your father looked between the two of you confused, “Wait how do you know each other?”. He was almost scared to ask, knowing Dean’s past. “The grocery store actually, his daughter-” You started but he cut you off, “Cassie.” He corrected. “Right, Cassie wandered off on the search for strawberries was it?” You questioned, looking down at the little girl still dressed in her pajamas. Dean smiled at the two of you, as she rubbed her eyes. “Yep slipped right out from under me, and found your daughter-” He said. This time you corrected, “Y/n, nice to meet you. For real this time.” You smiled as you extended your hand, to which Dean took in his, shaking gently. You almost passed out when he took your hand, whole body buzzing with tension as his engulfed yours. “Dean.” He grinned, looking down at you slightly due to the height difference.
Both Dean and your father watched as you crouched down to the little girl, “And it is so nice to see you again Cassie.”. Smiling at the little girl, this time her tiny little hand darted out to shake yours, you were quick to return the gesture before standing back up to your regular height. “I’m sure you two will get along just fine.” Your father looked between you and the little girl and then to Dean who was staring at you. “Don’t get into too much trouble while I’m gone, okay?” Dean pointed between you and his daughter to which she just found hilarious as she bursted out in giggles. “No promises dad.” You teased, and a spark went past Dean’s eyes as he went to speak but choked on his words. “Right. You girls be good, okay? Have fun” You and Cassie walked the pair to, and out the door. Waving at them as your father’s truck pulled out from the driveway.
—
You were told to have fun, and fun you had.
First order of business, like any, was to put on a gorgeous princess belle dress. Of course. Every princess needs a good breakfast so that you got to making. The smell of banana filled the air as you flipped the pancake, one of which was supposed to look like a crown, though ended up more like a squiggle. Cassie loved it nonetheless. After pancakes you decided to make cupcakes for your fathers’ return. A mess of sprinkles and frosting later, you have 12 well 10 cupcakes. You and Cassie had to make sure they tasted good. The two of you played for hours, swinging and running around the yard. Playing just about every game that could be played. The sun beginning to set, you had come up with one final activity. “Oh come on you’ve never built a pillow fort?” You asked the girl, and she shook her head, “Never-ever.” She replied. “Well it is your lucky day because we are about to change that sister.” You smiled down at the girl and the two of you started to round up all the pillows and blankets in the house.
One magnificent pillow-fort later, and both of you were tuckered out. Cassie had finally given up the ghost and was passed out in the fort as the credits of Princess and The Frog rolled in the background. The sound of car doors shutting, followed by the low hum of your father’s truck pulling out of the driveway filled your ears. You perked up as the door swung open and Dean stood there looking into the living-room.
You sat up against the leather of the couch as Dean walked into the living-room, “Oh you two had a blast didn’t you?” he muttered smiling down at the fort before meeting your gaze. “Best babysitter ever.” You motioned to yourself playfully. “I bet sweetheart.” He grinned while deconstructing the fort to retrieve his daughter. You started to refold the blankets and he held her close, still sleeping, and took her upstairs to her room. Folding the last blanket you grabbed your phone charger off the couch and put it in your bag, before starting to clean up the kitchen. You had just started to wash the dishes when Dean came back down the steps, this time empty handed.
“You don’t have to do that.” He muttered as you rinsed the batter bowl from earlier. “I don’t mind.” You smiled warmly. It felt almost domestic, intimate. He reached for the plate of cupcakes, picking one up and peeling back the wrapper. You watched as his hands worked at the paper before he brought the dessert to his mouth and took a bite. You swallowed hard and he noticed. “Everything alright there sweetheart?” He asked, grinning while he chewed and finally swallowed the bite of cake. “Mhm, any good?” You questioned and he nodded. “Been awhile since I’ve had somethin’ sweet.” He muttered.
It almost felt loaded.
Like he meant something other than that cupcake in his hand.
“Glad I could help.” You smiled and teased back, hoping you weren’t mis-reading signals. He smirked as you dried your hands with the dish towel. Leaning over to wipe down the sticky frosting-covered counter, Dean pressed against you. You froze as he spoke, “Now what did you mean by that sugar?”. Your face went red as you laid there against the counter, pinned between him and the cold surface. “T-The cupcakes, something sweet.” You replied in a choked stutter. Smooth. He laughed from behind you. You could feel the vibrations from his stomach against your ass as he spoke, “You and I both know damn well I wasn’t talking about a cupcake sweetheart.” His words went straight to your core, dripping with each word. You stood up, still pinned but now with your back to his chest. “You knew that, didn't you baby?” He whispered into your ear. Lips ghosting over your neck, leaving goosebumps in their path. You nodded as you melted into his touch. “I’m gonna need you to give me more than that angel.” He said as he turned you to face him. Grabbing your hips, he sat you on the counter. Barely meeting his height, he pressed his forehead against yours.
“Dean-” You whimpered in frustration, wanting nothing more than his hands on your body. “Haven’t even touched you yet and you’re already falling apart.” He whispered, his lips almost touching yours. Not wanting to wait any longer, you leaned forward and pressed your lips against his. A tangle of limbs, resulting in your sweatpants around your ankles left you craving more. “Please I need-” His voice cut yours off, “Need what baby? Tell me and it’s yours.” He tested your restraint, leaning down to kiss your thighs. The top of his head pressed against your stomach, and your hand tangled in his hair. Dean groaned against the feeling of your nails on his scalp. “Fuck.” He growled. “Need you Dean, everywhere.” You whined, and he finally gave in.
Pulling your sweatpants past your ankles, he tossed them to pool on the floor. His hand cupped your head as he leaned you back fully against the counter. Gripping firmly onto your thighs he spread you open, head immediately going to your core. Pressing open mouth kisses against the cotton of your underwear, he watched intently as you squirmed against the laminate. His skilled hands pulled the thin fabric to the side, like a cupcake wrapper. Your nails scratched against his scalp as your fingers tangled in his short hair. Groaning against you as his tongue delved inside you. His eyes, once a soft shade of emerald green, were darker and boring up at you. Dean watched your every move as his tongue worked skillfully on your clit.
It was like a bomb went off when you finally came, taking your hearing and eyesight with it for a moment. Your chest heaved as you laid sprawled out on the counter, Dean licked his lips as you sat up, resting against your elbows. “Sweeter than that damn cupcake.” He grinned as his thumb rubbed against your thigh. “I need more Dean–please.” He looked at you with hungry eyes, “We don’t have to do anything you don’t want to sugar.” He traced your hips, and you grabbed for his belt, “Need, Dean.” You said it plainly, not being able to simplify it anymore. With that he didn’t waste any more time and he unbuckled his belt in the midst of a messy make-out. He quickly rid himself of anything that could keep you from him. Pressing the tip of his cock against your slit, he leaned his forehead against yours and watched as your eyes widened at the intrusion. The way your face scrunched he could tell that it hurt and he was quick to comfort you.
“I know baby I’m so sorry.” He cooed as he pressed inch by inch in until you were flush against him. Soon, pain turned to pleasure and you allowed him to move. Each rock of his hips buried deeper inside you, you weren’t gonna last long like this. Whines and groans mixed together as you both approached your orgasm. What you didn’t expect was Dean to pick you up, wrapping your legs around his hips and plant his hands firmly on your ass. Gripping the flesh, he pounded into you ruthlessly. Rutting the deepest he’s ever been.
He tried to hold off as long as he could, wanting to soak in as much of this moment as he could. You cried out into his neck, sinking your teeth into the soft flesh as you came. “Oh fuck-” He groaned, not expecting the bite. That’s what dealt him in, the sharp pain of your teeth into him was too much to hold off on. One last thrust he came inside of you, painting your walls with a thick creamy off-white. Setting you back down on the counter, he pulled his softening cock out of you. Whining at the loss, he kissed your lips as he dripped out of you and down the side of the counter. Wiping you clean with wet-paper towels, he muttered with that boyish smile, “You free next week?”.
