Not Me Working On Another Wip That I Thought Of Last Night Lol. I'm Gunna Try To Make This A One Shot

The first clip 😭🤣

CR: @ackleslut TikTok

best friend's dad!jensen .ᐟ ˚｡⋆୨୧˚

okay so bear with me !! this saved as a video but i saw this gif on twitter and (my smut-rotted dilf-obsessed brain) immediately thought best friend's dad!jensen….. 18+

cw: smut, age gap (obvs), perverted!jensen, yearning, icky morals / character dynamics, reader is implied 18–mid 20s.

the way jensen looks at you, practically undressing you with his eyes, the young thing that you are, is foul to put it simply. he knows his perverted thoughts about you are inappropriate, probably verging on immoral—you’re the same age as his daughter for fuck’s sake—but that doesn’t stop the flutter of his heart or the throb of his dick anytime you’re near.

it’s like a compulsion; all he wants to do is teach you how to take his cock, make you yearn for it when he’s not around. he wants you so completely dependent on him that it makes you sick when you’re not with him. the need to slip his slimy fingers into every fold of your brain and manipulate you into a docile little lamb for his own pleasure makes him feel like a goddamn perverted mess.

he’s completely out of line, and he knows it.

but the idea of bending you over and cramming his pulsating chubbed-up cock into your tight young cunt, watching you whimper and blush as you make a mess of his pelvis with your sweet juices? jensen could jizz in his pants at the thought alone.

and the way you squirm under his gaze whenever he looks at you, his piercing green eyes and wolfish smile that shrink you into nothing but a floundering babbling little girl? yeah, he’d be silly to think he’d ever get over this fascination with you.

and the thing is, he knows you want him just as bad.

it’s evident in the way you squeeze your thighs together when you’re sat on his couch, watching a movie with your best friend, trying to find relief for that dull ache between your legs that always seems to linger whenever he’s around. or in the way your pretty eyes always flicker back to him when you think he isn’t looking. you’re such a sweet silly thing, really. he wishes he could just scoop you up into his arms and take you someplace where he could just bury his head between those sweet thighs of yours and pull orgasm after orgasm straight from your core.

you’re such a polite girl whenever you’re over at his house, so you’d deserve it, right? ….right?

and those times when he’s picked you and your best friend up from a party, helping as you stumble into his car drunk, giggling like two little school girls. the way his hand stays a fraction too long on your lower back as he helps you into the car, longing to dip lower and grope at the fat of your ass. and that charming smile he shoots you in the rearview mirror that says “such a good girl, coming home to me instead of going home with a silly boy your own age. that’s my smart girl.” those silent but oh-so-telling glances make your breath falter and your stomach pool with heat.

and jensen’s no idiot. he can see when a sweet young thing like you feels a little… flustered. he’s an attractive man; he knows when a lady has taken a liking to him.

but you? sweet little innocent you?

god, it’s bad. he feels like a sick pervert when he’s laying in bed at night, slowly stroking his cock to the thought of you—thinking about how good your pretty lips would look wrapped around his thick member with those sparkly little eyes of yours looking up at him from your knees, or how tight your walls would hug and squeeze his throbbing dick. the desire sears through him, his infatuation with you setting his body alight. he knows it’s wrong; you’re too young for him, too innocent, too good. but fuck, he needs you so bad. he wants to fucking ruin you, have you babbling as you bounce on his dick, whining about how good it stretches you out and how you’re his girl. his.

little does jensen know, your late-night thoughts mirror his exactly. you need him in a way that is indescribable, insatiable. your fingers dance around your folds, rubbing, pinching, curling up into your hole at the thought of him. but it’s just never enough. the idea of letting him, your lifelong best friend’s dad, split you open and use you however he pleases is another level of daddy issues you refuse to mentally unpack. it’s wrong; you know it’s wrong. he watched you grow up for goodness sake. the countless times he picked you and his daughter up from school. the times he took you both out for ice cream or to see a new movie. the times he’s called you his “second daughter.”

but yet, you catch his stares, the glances, the way his tongue swipes over his bottom lip when you enter the room. and you feel the way his hands linger on your skin, branding you with warm tingles and a fire that licks up your spine.

you just wish he’d do something about it.

like folding you in half, knees against your chest, fucking you into the mattress, stealing the breath right from your lungs as he plunges into you, his cock leaking pre into your needy hole. you’d do just about anything to be entangled in his bedsheets, his hand over your mouth, stifling your mewls and whines as he whispers into your ear: “shush, baby… shh shh shh, she’ll hear us. we don’t want my babygirl knowing what we’re doing, do we? keep quiet f’me, sweetheart. that’s a good girl.”

the overwhelming need you have for jensen is soul-crushing cause you know, deep down, he’d never consider stepping out of line with you… would he?

fig yaps: i’m not sorry if this is FOUL !!!! cause like that fucking gif? i cannot. the way his eyes flicker up and down... the fucking smirk??? yeah... i need him so bad. ANYWAYS ENJOY PERVERTED BSF!DAD!JENSEN !!! there’ll be more of him,, and it will be me just typing out my fantasies lmao

feedback and reblogs are welcome and appreciated !! thank yaaaa <3

✦ taglist: @chevroletdean @fitxgrld @jasvtsc @bluestrd @1-imbroglio @titsout4jackles @faithfulsofi @tortureddarkstar @abellmunsonmovie @legalmente-loca @theoneandonlystonedspiderman420 @manicjk @jensenacklesballsack @minettacreekk @winchester-whiskey @emeraldcrs @freyabear @daylighted @cosmopolitan-thedrink @jwritestuff @suhnisideup @spookyysinsanity @kimxwinchester @bleuatlas @deansbbyx @angelicjackles @deansbeer @artemys-ackles @bluemerakis @misatxox @star-yawnznn @ambiguous-avery @starzify @littlesoulshine @jays-bonnie-on-the-side @freeluigihesbae @bejeweledinterludes @deanswidow @psychicnatural @ghostlyaccurate @k-slla

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i don't wanna be productive i wanna tongue kiss a man in his 40's

02. takes one to know one

ᯓ★ story index abt, you join your new friend, outlaw!dean, in a little game of cops and robbers. warnings, robbery, guns, suggestive language, sprinkle of angsty hidden feelings, there's only one bed couch (more of that in prt3!!) 2.7k words

The sheriff had a lot more going on than just civil duties, the vast ranch set picturesque before you can attest for that. The house itself is massive, pure white siding glowing in the moonlight. Beyond that, a sleek brown barn cuts into the night sky. From where you and Dean sit, crouched behind one of the dozen jagged shaped trees that line the outskirts of the property, it looks deceptively peaceful. 

But you know better.

This stash of gold Dean assures you is hidden within those walls, isn’t gonna be an easy swipe. Guards patrol the quiet ranch, a few are pacing the front as you watch and search for a blindspot. 

“You sure about doin’ this, darlin’?” Dean drawls in a hushed whisper, his eyes light and playful, almost daring you to say no. 

Your narrow-eyed gaze goes toe-to-toe with his, your lips curling into a smile. “I was born sure, Winchester.” you quip, not missing a beat. 

Dean’s husky voice drops lower, momentarily lacking it’s usual cocky drawl, “you just stick to the plan, alright? You do that for me ‘n we’ll be swimmin’ in gold before sunrise.”

You rolled your eyes but couldn’t ignore the steady thrum of adrenaline in your veins. The plan—Dean’s plan—was simple enough: get past the guards, crack the safe and get the hell out of dodge. Simple, of course, was a relative term when talking about breaking into the home of a man who probably shot first and asked questions—never. 

“Remind me again why I agreed to this?” you tease, tucking your body closer to his. Your chin grazing his leather-clad shoulder as you both keep steady eyes on the ranch. 

Dean gives a quick glance, the moonlight catching in the green of his eyes. That pretty grin of his making a slow return. “Because you couldn’t resist me.”

Playfully hitting his arm, you shoot back at him, “or maybe I couldn’t resist the payday.” His eyes are back on you, lingering as his lashes slowly lift as he takes in your features at this newfound closeness. He merely offers a quiet hum in response, brushing against you as he shifts to hand you a small set of lockpicks. 

“Figure, with the way you work a cue stick,” he mumbles, voice low and as teasing as his eye contact, “you got this part handled.” He places the small box in your hand, clasping his large hands on either side of yours as he smirks, “And I’ve got a knack for getting into trouble. Perfect match, huh?”

Before you could reply, the sound of boots crunching on gravel causes both your heads to snap towards the ranch. A guard passes by, just a few yards away, his rifle glinting in the moonlight. Dean’s playful demeanor is entirely consumed by a sharp alertness that makes you wonder just how many times he’s been in a situation like this. 

The stillness passes as the guard meanders away, the sound of his boots dying out in the quiet of the desert. Your new partner’s shoulders relax at the false alarm. That lopsided smile playing at his lips again as he tugs you closer, his nose brushing your cheekbone.

“Showtime, baby.” Dean whispers, pulling back with a wink as two fingers reach up to tip his hat. 

The two of you slip through the shadows of the ranch like ghosts. A mere step between your bodies as you stick close to the edges of the house where the moonlight doesn’t touch. Dean leads, moving with surprising stealth for someone so broad. Every now and then, he glanced back at you, giving a little nod of reassurance. His focused eyes softened slightly each time he turned back. 

Moving through the property was easier than you thought, but Dean’s uncanny sense for danger has made it so. He pauses just before a light sweeps over your path, his hand shooting out to pull you into the shadow of a nearby tree when he detects movement before you do. The guards are predictable, too. Their routes timed perfectly to give just enough room to duck behind a stack of barrels or hop over a fence. One guard left his post at the backdoor, leaving an opening to slip into the darkened home. 

You follow Dean’s silent lead of avoiding spots of creaky floorboards as you step inside, pulse thrumming with adrenaline. As you move through the dark, Dean peeks through doors with deliberate slowness. You watch between him and the back door, until he’s motioning you over with the flick of a finger. 

The study was just as grand as you’d imagined—dark wood paneling, glass cases displaying expensive weapons and memorabilia. A massive desk cluttered with papers sits before two large windows. In the center space, a portrait of some grim-faced ancestor takes up most of the wall. 

Dean’s already hovering over it, inspecting the frame. The sharp edges of his side profile illuminated by the moonlight spilling in through the window. His eyes finally catch yours, nodding for you to come over, a sly grin on his lips as he leans down over your shoulder. 

“These rich sons of bitches are always so predictable.” He laughs dryly, “go on ‘n tug on that side of the frame for me, Sweetheart.” 

You don’t waste a second, pulling on the frame until it pops open. Swinging like a hidden door, revealing a built in safe on the adjacent wall. Pulling the small box of tools Dean gave you earlier, you get to work on the silver lock. The tumblers click softly as you go, each sound loud in the otherwise silent room. Dean stood behind you, close enough to hear his steady breathing. Keeping an eye on the door, his hand resting lightly on the gun tucked into his waistband.

“Got it,” you whispered after what felt like an eternity. The safe door swung open, revealing stacks of gold bars that gleamed even in the dim light.

Dean let out a low whistle. “Now that’s a sight.”

You quickly began transferring the bars into the canvas bag Dean had brought, your heart pounding with a mix of excitement and fear. 

This plan of his had gone so smoothly, too damn smooth to be more accurate. 

Just as you finish zipping the bag, heart still hammering in your chest, a muffled voice barks from the hallway, “check the study!”

Dean’s jaw tightened as he reached for the gun tucked in his belt, but the door burst open before he could draw. Two guards stormed in, their guns trained on you both.

“Drop the bag,” one of them ordered, his eyes narrowing.

Your mind raced as Dean slowly raised his hands, palms out in mock surrender. His smirk returned, cool and steady, as if staring down the barrels of two guns was just a typical Thursday night for him.

“Well,” he drawled, his gaze sliding to you. “Guess now’s a good time to make a confession.”

Your stomach dropped. “Dean—”

“I mean, might as well, right?” he continued, cutting you off. His smirk softened into something maddeningly sincere, his eyes holding yours even as the guards barked for him to shut up. “You’re the prettiest little thing I’ve ever seen. And if I were a better man, I’d have asked you on a proper date. Y’know, steak dinner and all that crap.”

You blinked, completely thrown, but before you could respond, Dean’s hand shot out, grabbing the desk lamp and hurling it at one of the guards. The heavy base struck him square in the face, and chaos erupted.

Dean didn’t hesitate. He ducked under the second guard’s arm, grabbing the man’s wrist and twisting it until the gun clattered to the floor. “Move!” he shouted at you, his voice sharp.

You didn’t need to be told twice. Snatching the bag, you bolted for the window, Dean hot on your heels. He shoved you ahead of him, glass shattering as you both tumbled through the opening and into the cool night air.

The shouts behind you were nearly drowned out by the pounding of your heart. Bullets whirl through the air, but Dean grabbed your hand, dragging you across the open yard and toward the safety of the rugged desert terrain ahead.

You didn’t stop running until the ranch was a distant glow behind you, your legs screaming in protest as you collapsed against a tree.

Dean slid down next to you, his chest heaving as he tried to catch his breath. A laugh escaped him, soft and incredulous. “Hell of a night,” he muttered.

A wicked laughing fit hurls out of you through panting breaths, reeling from the cooling adrenaline icing your veins. “You really had me for a second, y’know,” you manage through heavy breathes, “d’you mean any of that? Or was it all just part of your plan?” 

Dean smirked, taking off his stetson to run a hand through his messy hair. “Which part?”

“Oh, I don’t know,” you teased, biting your lip in mock-deep thought. “The part about me being the prettiest thing you’ve ever seen? Or the bit about steak dinners?”

Dean chuckled, leaning his head back against the tree trunk, lazily tilting to peek down at you through his lashes, “I told you I wouldn’t lie to you, didn’t I?” He’s doing it again—that smug little smirk—a sweet boyish charm that tempts your nerves in the most unfamiliar way. 

You turn away from his gaze, settling your eyes on the bag in your lap and letting your hair fall around your face to cover the blush that’s creeping in. “Mhm,” you hum into the quiet between, “careful now, cowboy. I might just hold you to your word.”

He doesn’t answer, and you pretend there isn’t a slight twist straining your heart for half a beat. Quietly, he places his hat back on. Pressing into the ground, he rises to his feet with a huff. Dean extends a hand, his eyes scanning the distance as you take his offer. 

Boots kick up dirt as you walk side by side down the dusty terrain. And for a moment—in the quiet of the desert, with the bag of stolen gold between you, the danger of the heist morphed with the dawn settling in the horizon. A warm toned thing, burning at the edges of your cold exterior, new nerve endings bleeding light between your thoughts of Dean and the feelings he keeps insighting. 

Trudging on, the sheriff’s ranch is out of sight. The weight of the gold was growing heavier, hanging from your shoulder. But you’d be damned if you let him carry it, not when it felt like grasping some essence of control. 

“So,” you drawl, kicking at a red rock, “you looked like a real professional back there. How long’ve you been sniffing out trouble like this?”

Dean shrugs, burying his hands in his pockets as he considers his words. “Sorta spent my whole life in some type of trouble.” he states plainly, voice quieter as he continues, “Been on my own a couple of years, give or take. Found the type of trouble I like best in all that time.”

You glance up at him, his skin soaking up the orange light peeking over morning clouds. The warmth of the hue makes his eyes impossibly green. Like the cactuses zig zagging your path, sharp and rich in color. “You like it? Being on the road?”

“Yeah,” he sounds unsure, pausing with his lips parted, “Most of the time, I do. It’s… simple.” His hands return, moving with each word, “No strings, no one to answer to.” 

You hum back, nodding in agreement. It’s a sentiment you can agree with, the same idea you've convinced yourself of for much longer than just a couple years. 

“But,” he sighs, eyes flicking across the landscape, “I miss my brother, Sam.” The name makes a smile creep onto his lips as he mutters, mostly to himself, “m’little Sammy.” 

There’s a softness on the name that makes your chest ache, “Why don’t you go see him, then?”

Dean hesitates, jaw tightening, “not that simple.” He let out a low breath, running a hand over his chin. “I don’t even know where I’d start. And if I ever tried to show my face to my old man…” His voice trails off, the words tangling in a wide-eyed huff that says it all in one motion. 

You part your lips to reassure him, daring to give the advice of it’s-never-too-late to a soul you know won’t take it. But, before you could he hummed a low, dismissive note. 

“Anyways,” he quips, a lazy grin returning to his face, “look at me, turning into a regular chatterbox. This your doin’, pretty girl?” His eyes find yours, but the usual playfulness isn’t as prevalent as it has been all night. In its place is something dark, trying desperately to work its way out. 

A look you know better than to pry at. 

Leaning over to nudge his shoulder, you offer a small smile. “Maybe I’m just easy to talk to.”

Dean’s grin shifts into something softer, but he doesn't answer. With a deep inhale his chin is up in the air again, eyes looking at anything but you.

 A splotch of brown you both assumed to be more rugged desert hills comes into focus—a vacant ranch tucked between scattered fields of jagged trees and cacti. The barn had collapsed, its frame a shadow of what it once was, but the house stood stubbornly, its roof intact and its windows dark against the rising sun. 

Dean raised his brows, eyes glancing over, “looks cosy.”

You scoff, giving him a worried look, “if your idea of cozy is ‘haunted ranch on the hill’, sure it is.”

“Better than sleepin’ out in the dirt,” he shoots back, already heading for the porch. He spins on the heel of his boots as he walks backwards, “‘sides, darlin’, if there’s a ghost around I’ll keep you safe.” 

With a wink that works a giggle out of you, Dean jogs up the creaky steps and disappears into the run-down house. 

 The inside is covered in a layer of dust and dirt, but there’s furniture scattered around—a worn couch covered by a sheet sits in an otherwise empty space. A creaky dining table in the kitchen, where you plop the heavy bag of gold, a cloud of grey puffing around it. 

“Not too shabby,” Dean coos, coming down a set of weathered stairs. “Just an old mattress on the floor with, uh, minimal stains and a whole lotta dust. Looks like we’ve got options.” He crosses the creaky floor until his boots are inches from yours. A smirk shining down at you, as his voice finds that teasing tone again, “Unless, of course, you’re afraid of ghosts.” 

Your eyes roll at his taunts as you cross your arms. “Please. I’m not afraid of anything.”

“Uh, huh,” his brows furrow, lips twisting with contemplation as his eyes dance across the curves of your face.

“Yes, huh. Cross my heart.” You swear with a reassuring nod. 

His eyes fall to the couch, and then back to the stairs before they settle back to you. His thoughts written in the smirk on his lips. “Mattress is kinda gross, actually. Couch could fit two—”

You cut him off, throwing your palm up with a humph. “Look, Cowboy, I may look the type but it takes a whole lot more than a game of pool and stealing gold to get me all cozied up on a dusty ‘ol couch in the middle of the desert.”

Dean barks out a laugh, holding his hands up in mock surrender. “Hey, hey—’m not suggesting a thing, little miss.”

You arch your bows with a “mhm,” the faintest hint of a smile tugging at your lips. Dean follows as you walk into the living room, discarding the sheet and plopping onto the cushion with a sigh. The couch dips under Dean’s weight on the opposite end. A quiet set in for a moment, comfortable and as warm as the growing heat of the sunrise. 

“Will say, though,” Dean sighs, his thighs sprawling over the soft surface as he relaxes into the creaky furniture, “I’d be a gentleman—”

“Shut up.” you shoot back, unable to hide the laugh that slips between the words.

hmmmmm should they boink in the next part???? hmm hm hmm

tags <3 @the-fandoms-onceler @a1ecmcdowell @titsout4jackles

Hi, I'm Destiny! Welcome to my fanfic account!

I’m 25 years old and I'm currently trying to redirect my life in many ways. I'm off of everything social media besides tumblr and pintrest, I don't really count them as socials (I should). But at least with tumblr I can read and get inspired!

I have always loved reading (even if I read at the speed of a snail), and I've always loved coming up with scenarios in my head. I've had a lot of trouble in the past keeping up with the works but it's time to turn those tables!

Please be kind, the world needs more of it! My inbox is always open for YAPPING!

Things I really love: The Office | One Direction | Supernatural | Roswell (1999) | Elephants | Coffee & Tea | Any and All Things Music (besides gospel sorry!) | Exercise | Tattoos | Piercings | Horror Movies | CreepCast Podcast | Normal Gossip Podcast | Murder Mystery & Makeup I have a good-sized library of records and cassettes and vhs tapes, books (obviously). Buy physical copies of things if/while you can!

A Girlie For: Harry Styles | Dean Winchester/Jackles | Henry Cavill | Niall Horan | Chappell Roan | Sabrina Carpenter | Miley Cyrus | Chris Evans

MDNI; 18+ ONLY!!

may the fourth be with you or whatever they say

Yeah now we've entered the back pain stage

In the Fields We Lie: i

Summary: World War I is at its climax. Dean is figuring out his life before his name gets drawn from the draft. Falling in love while he can. Will he get the life he always wanted? Or will the war destroy him? Word Count: 3k

Warnings: british!dean?? let's spice it up a little bit! I just know his deep voice with this accent would eat me alive if I could actually hear it! Also, world-building. No legit tw's.

Prologue

They say that in the midst of darkness and a time where nothing prospers, the mind tends to wonder. This is the time where inspiration strikes and masterpieces are made. There is, more than anything else we have in the world, is time. What we do in that allotted space is up to us to choose. What shall we occupy ourselves with? Where shall we let our minds wander off to? Distant lands or perhaps a reality that we dream of that is better than our present? Do you dream of being in your lover's arms? Or do you wish you could have taken back those harsh words you said to your mother recently? Others have to think quickly, in a fraction of a second, or else they will not live to see the light of day. 

In that darkness there is chaos and when everything turns quiet, is that moment of primal instinct to save your life or to accept that death will grab you and bring you to a hell that you have not seen yet. Anything to keep the mind busy in times of hardship is crucial. That is how we survive. The silence, especially in the time of war, is deadly. So deadly that it could turn anyone crazy.

Every soul is trying to keep themselves safe and there is not an option otherwise, unless they have lost their way. Lost hope. Those are the people you have to take care of, to watch out for. Without community and camaraderie, there is no purpose. Without care for others is the destruction of oneself. Without the care for oneself is to rot. Those who only think of the betterment of themself are soulless. To be self-sufficient is another story. To have support behind you, next to you, in front of you–gives you strength. To know that others are experiencing life similar to yours is comforting because ultimately you’ll feel less alone.

—

England

17 December, 1915

Friday

Dean Winchester was young and eager to work. He had always put some money to the side but now, with no end in sight to this war, he's been saving every penny. Maybe he could afford to send his brother to university–to save Sam from being a pawn in someone else's game.

It was a particularly cold morning, grey clouds coated the sky as far as you could see. The freezing air hitting Dean in the face feels like a pound of bricks. He’s already slipped and landed on his ass twice this morning while walking to work. Dean got a respectable job as a high-end tailor three years ago–a trait he has been naturally good at, all thanks to his mom.

He’s okay with having a wet bum because he knows the ladies he works with are going to have a good time making fun of him. What he isn’t okay with is his inability to stop daydreaming about his neighbor, and that is exactly what he does walking two kilometers to work.

They are acquainted. Dean has helped her move furniture and tried to fix her shower pipes once but failed miserably. The war is only getting worse, and there's no one to fix the problem–so that means unlimited access to his washroom. She has occasionally made him food whenever he came home late, or she would purposely bump into him in the morning before work to put a smile on his face.

They enjoy each other's company so much that they go to the market together to buy groceries. Sometimes, Dean stargazes in the park right below their building. On the occasion, she sees him through her kitchen window–every time she joins him to make sense of the clouds and their shapes. They’d always lay in silence, enjoying the presence not only from one another but the vast universe above them.

In this particular moment all Dean can focus on is her being in his home, using his shower. Being the gentleman that he is, he respected her privacy when she was over to wash up, which was almost every night for six months. But he also couldn’t, and presently cannot help but imagine her beautiful figure underneath her clothes.

The sound of her humming to herself in the shower echoes through his mind as snow crunches under his feet. Her voice sounds like a goddess blessing all of creation, a thought that had crossed his mind yesterday. She slipped the very first time she had been over and fell pretty hard; she screeched but then laughed hysterically. It was something Dean could get used to. Her coming over made Dean feel whole–made his flat less lonely.

In the first month of this situation, she had forgotten a change of clothes, and it was then that Dean knew he was truly in love with her.

—

Dean was making some boiled chicken and pasta when he heard the shower handle squeak and a handful of choice words fall from his beautiful neighbor's mouth. He assumed that she had rushed too fast while getting her toiletries together that she had forgotten her hairbrush or lipstick or something...

She had a date waiting for her outside the building. Jealousy raged over him when she told him that a particular man was taking her out to dinner. Apparently, they’ve known each other since grade school, even dated in their early teen years, and then reconnected at a mutual friend's wedding. The negative emotions he was feeling quickly dissipated when she said his name.

“Dean…”

She sounded worried. Why was she worried? Was she nervous?

“Fran, I know your nerves are getting the best of you, but I’m sure you look lovely…” He turned around to find her in just a towel. Eyes widened, jaw dropped, and heart racing at a million miles an hour. Too stunned to speak, Dean quickly spun on his heels so he wasn’t starring. “Shit, I- I’m, I-”

She’s now laughing at his embarrassment. All worry washed away from her voice, “I forgot my dress. I guess I was so excited to get ready that I forgot it. Can I borrow a blanket or shirt to cover up in?” 

After a few moments of silence she walked up to him and tapped his shoulder and spoke, “Dean, it’s okay. Turn around.”

He did as he was told, making sure that when he did, he only looked into her eyes. She was so beautiful–so confident in her body and in herself to let a man she wasn’t with, to look at her when she was indecent. A strand of curly hair fell into her eyes, before she could move it herself. Dean gently pushed the lock behind her ear, and both of their breaths caught in their throats. 

Dean managed to whisper, “I’ll um, go grab you a shirt.” He never walked so fast in his life. Making sure he picked out a nice shirt that smelled good was top priority. He ended up dabbing some cologne on the collar just in case.

She was too busy admiring the books on his bookshelf to notice that he had come back, so he cleared his throat before speaking, “Fran, you better change quickly before your date thinks you’ve fallen in the toilet.”

“Ha, ha. Very funny Winchester. Gimme that.” Snatching the shirt like it was hers to begin with. She disappears behind the washroom door and reappears seconds later it seems like, but maybe that’s from the state of shock Dean’s still in. Fran has to ask him this twice to get his full attention, “Will you watch for any unwanted eyes as I walk to my flat?”

“Of course I will. Let me see your key so I can unlock your door.” 

Walking past her is painful, he can feel his excitement pushing against his trousers. It’s only just started but he needs to be free of Fran soon or else she’ll see his indecency. Moving quickly and lightly, making sure not to cause a ruckus and concern the nosey neighbors. He unlocks her door and sets her key on the small table that sits just to the right of the door. Making sure that no one is in sight he quietly calls out her name. She holds her dirty garments to her chest as she sleepwalks to him. Hopping almost. Bloody cute, this one, Dean thinks to himself. As soon as she’s in her doorway Dean stands in front of her with both arms outstretched, and hands grabbing the baseboards to make for a better cover for Fran.

They are extremely close again, both of their hearts are pounding so hard it’s a surprise they can’t hear each other's heartbeats. 

“You better have fun on your date. Hurry along then, you don’t want to miss him.”

“Oh, I will. Aaand… don’t tell me what to do.” Fran winked at him and then closed the door in his face. Dean smiled and walked back to his flat. He ended up burning his pasta on the stove. If this was any normal night, he would have lost his wits if he burned his food, but he made an exception for the gorgeous woman that stole his attention.

—

Ever since that incident, a very particular image of Fran has been taking over Dean’s mind. The shirt that Dean gave her was a pale pink shirt and he never realized, that without an undershirt underneath, that it was sheer. When Fran came out of the bathroom, her hair had gotten the fabric around her breasts wet. It was only for a brief moment that he looked, and Dean swears that she did it on purpose. She was perfect, everywhere. He thought he saw her smile when he gazed his eyes up and down her body, seeming almost satisfied with his actions. An angelic devil.

Too distracted by his thoughts, he barely realized that he was arriving at work. Taylor the Tailor: “Let Taylor, Tailor You!” was displayed above the building in bright red lettering. It was a quaint little shop that sparked Dean’s interest when he first moved to the city. Before he even asked for a position, he had to come in for a repair on a set of trousers. Long story short: while moving into his flat, he had slipped on some ice like he had been doing presently, and ripped them right down the bumline. Quite embarrassing, even more so, considering one of his neighbors came out of the building right as it was happening and laughed. It turned out to be Fran. She still teases him about it.

His mum taught him how to sew, crochet, and knit, so already having experience was attractive to the owner, Mr. Taylor. He was hired on the spot actually. He loves everyone he works with and that’s the reason why he’s stayed with the shop for almost two years. 

He welcomes Mimi and Rena as he walks through the main room and towards the back to set down his jacket. Dean can hear the two older ladies gossiping about who knows what but it makes him chuckle. They think they’re whispering but they’re both basically shouting at each other.

“Ladies, ladies,” Dean interrupted them, “No need to whisper about how gorgeous I am, when I’m right here!”

Rena rolled her eyes, while Mimi stood up and made her way to him. Mimi takes his blue bowtie from his hand and begins to put it on for him. A little tradition that they’ve made. Dean is fully capable of doing it himself but he lets her. They both gain from it. “Thank you, my darling,” He kisses her on the cheek when she’s finished. “And how are both of my girls today? Ready for the weekend?”

“Always ready for the weekend, Winchester. Two days out of the week where I am free of you.”

“I’m truly hurt by your words Rena. You know what that does to my ego. Everyone loves me, right Mimi?”

Mimi laughs, “You are very lovable Dean. Rena is just an old fart. You’d think after so many years she’d warm up to ya.” That is exactly how each day goes. Rena is the stern and conservative type but has her moments, Mimi is a freer spirit and can get along with both of her coworkers, and Dean is, well, Dean…

The day is long and cold, everyone is being careful not to let their fingers get too stiff. Their day has only gotten longer, because right before five o’clock, a woman comes in. She is in desperate need of fixing her husband's work attire that her children had shredded with scissors. Three shirts and four trousers. She was a fairly sweet woman and she would pay them extra to get it done for her by Monday morning. They all obliged.

To make things fun, Dean took on three garments that were badly damaged, and told the ladies he would finish all of them before they finished their two pieces. This didn’t amuse Rena, but she ended up finishing before him and she was greatly satisfied, giggled even. Getting out of the shop around half past nine was quite impressive and everyone patted themselves on the back for the hard work.

“Get home safe my loves, I will see you later. Rena, you better think of me!” He yells at them when they’re about to round the corner of the street. It makes Rena furious.

The weather changed within the last two hours, snow is falling fast. He usually doesn’t mind walking through it, but he’s afraid that he’ll fall like he did earlier. His tailbone was still throbbing. As if summoning the inevitable, he slips and one of his legs extends too far out in front of him. Almost ripping his pants, again! Thank goodness for having hands to catch you. It was a close call—the amount of stretch he felt was worrisome. 

As he approaches his building, he notices an all too familiar Rolls-Royce that belongs to someone who is the epitome of rubbish. Someone who is used to getting his way. Maybe it’s the money he has or possibly the fact that he has not struggled a day in his life–is why Dean hates him so much. There’s definitely another reason that has nothing to do with those things though. Dean is reluctant to go inside the entryway but likes to make this man suffer.

“Hello, Dick! It’s awful seeing you here,” Dean coldly welcomes him, “Where will you be taking Fran tonight?”

“For the last time, it’s Richard. And it should be none of your business, but I know she’ll tell you anyhow. We are going to my brother’s engagement party, and before you say anything–”

“Speaking of engagement, when will you ever ask Fran to go steady with you? Oh wait, that’s right, you were too busy getting your dic-” By the look on the other man's face, Dean knew Fran was walking up to them, “Dick! So lovely to see you mate!”

He then turns around and smiles at his neighbor. As he walks up to her, he whispers for her to be safe, and heads up to his flat. In the stairwell, Dean could hear Dick tell her how much he annoys him, and that is always his goal.

“Such a nosey neighbor…”

“I think he’s perfectly fine, Richard. Leave him be…” Her voice is so soft. She wouldn’t be talking so tenderly to him if she knew that he was seeing other women. It infuriates Dean to his core, but he can’t tell her because she would rip him a new one for knowing. Quite frankly, he feels like Fran wouldn't believe him.

Dick has her wrapped around his diseased little finger.

Second, Fran would be so devastated and Dean doesn’t want to deliver that news to her. She will find out sooner or later, and Dean prays that he gets front row seats to Dick getting his balls kicked in.

—

The storm only got worse throughout the night. The power went out shortly after Dean got home. Currently at the kitchen table reading a book but failing horribly from sore eyes, waiting for Fran to be dropped off. At this point it could be likely that she had to stay with Dick and his family, which is revolting.

It’s none of Dean’s business where she is, who’s she with, and he shouldn’t be waiting up for her but something isn’t sitting right. It's way too late for them to still be out for dinner. Maybe the group was drinking or something? Fran is a grown woman. She’s fine. Dean needs to stop worrying.

Looking out of his window one last time, to make sure he doesn’t miss her, is when he sees headlights crawling towards the building. Assuming it’s Fran, Dean sighs in relief and heads to his washroom to get ready for bed. As he gets done brushing his teeth is when he hears her walking up the stairs and decides to meet her in the hallway. Knowing she can barely see up the stairs from the power outage, he brings out a candle to give her when she gets home.

“How was your night out Miss Fran?” He questions as genuinely as he can, as she reaches the last step. She’s too quiet. He walks closer to her once she reaches her door and leans against the wall. She looks sad. Her eyes and nose are red. Dean can make out where the tears streamed down her face. His stomach flips and he feels nauseated instantly. 

What happened? He wants to ask but knows it’s not the time.

Her voice is hoarse, “You know, you don’t need to wait up for me—it’s sweet but a little strange.” She half heartedly jokes. “My night was fine, thank you. See you tomorrow, yeah?”

“Of course. Here, take this…” He straightens up, taking a few steps to get closer to her, and he smells the alcohol coming from her breath. It must’ve been a rough night because she hardly drinks. 

Handing her the candle and keeping eye contact he whispers, “So you can see where you’re going. I’ll come get you tomorrow.” 

Dean wipes away a fallen tear from her face with his thumb and kisses her cheek in that same spot.

So softly she murmurs, “Goodnight Dean.”

“Goodnight Fran.” He says with equal gentleness. With even more longing.

—

A/N: Please let me know what you think!! I edited this on four hours of sleep lol.

tags! @aylacavebear @daylighted (idk if yall wanted to be tagged but hopefully it's okay!)

before anyone asks, yes im ovulating

need him to hold me and tell me it's all good. it's fine.