#like. i want to spill coke on my keyboard and have it fry up and kill me. i want to jump off the cadillac and into a fucking volcano.

[ain-t-bovvered]

Bumpy road to Love 3

EDITED by @waywardbaby

Pairing:  Dean x Reader

Genre: 40s-50s Au. Singer Reader x veteran WWII Dean.

Warnings: none for this chapter

Disclaimer: the story takes place in the first year of WWII to the years right after, but I love the style and fashion of the 50s so some of the visuals and lifestyle will be not super accurate, especially during the flashbacks.

Summary: Many lives were ruined by the war, yours was not exception. You had money, before, stern but loving parents,a big house,and a secret love, all of that lost, burned down.  Now you earn yourself just enough money to get by, using the only thing the war couldn’t take, your voice. One foggy night, in the smoky and dark speakeasy where you worked, your imagination plays tricks on you and behind the smoke and whiskey glass , a pair of green eyes seem to read into your soul. A pair of green eyes that you thought you’ll never see again.

3.

I wrapped myself in my black fur shawl, the temperature in the club still low as the doors are open to let the smoke of the previous night out. Well that’s just stupid, I thought to myself annoyed and repressed a shiver sitting on the bar stool.

“I see you are not in a good mood today either, doll” Benny said as he was scrubbing the countertop with a towel and daring a smile to my direction.

“Shut up, Benny!” I scoffed picking at the peanuts on the counter “It’s cold as hell and I don’t understand the need to air the place. This evening will be thick with smoke again”I mumbled, raising a salt coated finger to my mouth and licking it, careful not to smudge the just lipstick coated lips.

“Well, I like to breath actual air sometimes” he said closing the shaker. I watched him, bored, my hand cradling my head.

“ Are we expecting many tonight?” I said raising my voice above the shaking noise.

“Yeah, tonight we’ll be full. You better get ready for some upbeat dance sets” he said pouring the shaker’s contents into your martini glass.

“..Oh ...wow, great!” I can taste the sarcasm in my words. I reached behind the counter to  grab a handful of olives and  Benny’s eyes fell on my wrist.

Damn it

“If that’s a new watch, you’ve been robbed” he said grabbing my wrist and eyeing the watch, “it’s stopped...and the style is a bit...” he eyed me suspiciously, “...is this a man’s watch?” he asked, squinting his eyes as he was trying to get top secret information out of you.

“...I liked the style, and I know it stopped.  I’ll take it to the shop this week” I lied, “...and Benny, I know the craving is strong but try not to steal it!!” I grinned.

Benny brought my hand up to kiss it lightly , giving me his most charming wink. I blew him a kiss as I grabbed my drink, took  a sip and walked to the stage, where Chuck was tuning the pianoforte. 

Leaning on the side of it, I crossed my arms, my glass hovering near my lips. 

“So….dancing tunes tonight, huh?” I asked, knowing exactly how much he detested them.

“..Oh joy!!” A simple roll of his eyes wasn't enough. His whole head followed as he reached for the drink, his ear close to the keyboard trying to pick up even on the tiniest out of tune note. His hand grabbed the air next to my glass so I obliged by handing it to him. Standing up, he took a sip and gave me a stern once-over. “...Darling, did you eat something before this?” he asked, his eyebrows furrowed, ready to scold me like a small child.

“Sure, I did” I opened my hand, revealing 4 martini olives.

When he saw that, he moved the glass completely out of my reach and downed the rest of my drink.

“Hey!” I protested.

“Go and eat something at the diner and I’ll give you another one afterwards ” he said pushing me off the stage.

I saw Benny laughing and shaking his head as I passed by the counter again. Slowing down I reached into his tips jar and grabbed a handful of scrunched bills, winking at him before quickly exiting  the place missing the towel he threw at me by mere inches.

The diner across the street was small, cozy and, thank god, warm. The smell of coffee and greasy food assaulted me as I pushed the door open, bell ringing.

“Y/n! , how rare to see you at this hour. Did Chuck send your ass in here?”

“Nice to see you too, Meg” I groaned, sitting heavily in my usual booth. She walked to my table, already filling my mug.

“The usual?”

“You know it”, I said scanning the tabletop jukebox titles “Did you add new ones?” .

“Yeah, Chuck kept nagging me about it and I needed him to shut up” she answered from behind the counter, leaning with her head to the kitchen window. “Number 5, 2 as a side”.

“Hiya Y/N !” came a loud, chirpy voice from the kitchen.

“Hey Donna” I greeted back.

“I kept your favorites in that one” she said winking at you.

My eyes shifted to the titles again recognizing most of my old favourites, the songs from another time.

Oh hello there, Bob Eberly and Helen O'Connell and their damn song.

“So...” he said sprawling on the seat, back against the window glass, one arm draped over the backrest and his legs, I know for sure because my feet bumped on his boots when I sat composed as usual, were wide open under the table.

“Ain’t you hot with that pretty cardigan on?” he said while scanning the menu he was holding.

I squirmed in my seat, fingers nervously tucking a curl behind my ear “I’m good, thanks”.

I was not.

He threw a glance at me from above the menu, eyes shining amused, probably reading me like a book.

I huffed, eyes rolling as I began to unbutton it. He was staring at me and I stopped , I raised my eyebrow in a silent request.

His eyes widened and he quickly covered his face with the menu.

Being almost summer, I wore a sleeveless camisole under it and I chewed on my lips feeling a bit exposed. So instead of completely removing it I draped the cardigan over my shoulders.

In one of the pockets I found a coin and I stared at the tabletop jukebox, fiddling with it and flipping it between my fingers. I love music but maybe I shouldn’t show it during a date...did I just say date? No, no, no, this is definitely not a-

He slowly took the coin from my hand, his fingers brushing mine feeling rough and lived, but his touch being gentle and warm.

“You ready to order guys?”

The waitress asked, breaking the moment.

Dean looked at me expectantly.

“What?”

“Ladies first”

“...” I gaped at him, and leaned closer. “You are supposed to order for me” I whispered, covering the part facing the waitress who was chewing a gum loudly,looking bored and doodling a bit .

He blushed slightly and sat up straight picking up the menu again, eyes quickly scanning the dishes.

“You eat burgers and fries?”

“ I do”

“Coke?”

“No ice”

“That’s all?” the waitress asked, scribbling down our orders and popping a bubble.

He threw a longing glance at the dessert section and I giggled. He caught me and blushed deeply, plastering a fake, cocky smile .

“That’s all, thanks”

“Sure, hon” she said and walked to the kitchen, swaying her hips.

“You are not used to this” I said smirking, head resting on my hand as I leaned on the table.

“Used to what?”

“Date”

He mirrored me and whispered “I thought this wasn’t a date” .

Now it was my turn to blush “Never said this -”

“Here’s your drinks” the waitress’s interruption being a welcomed one this time.

He leaned back, smiling pleased with himself,  as I grabbed the glass and drank through the straw, looking everywhere but him.

Remembering the coin he took from me before, he inserted it in the tabletop jukebox and motioned at  me, with his hand to choose a song.

I scanned the titles, curiously, not knowing what to choose after having mentally narrowed down my selection between two songs, one proper and one that my parents wouldn’t approve of.

I probably took too long because as my finger reached to select one he did the same, pressing the non proper one, my finger hovering on the other choice.

While waiting I started to hum at the song softly playing,watching outside the window, my feet moving in rhythm under the table, bumping into his from time to times without really noticing. He lowered his eyes under the table and looked up again but I didn’t notice that and I started murmuring the lyrics too, missing the way he was looking at me.

“Here you are hon, let me know if you need anything else”

“Thank you, Ruby” I smiled tiredly at the welcome distraction.

“Meg told me you’ll have a heavy night tonight” she said and refilled my cup .

“Yeah, couples dancing night and all that jazz” I answered, my tone bored and already sick of the night that hadn't even started yet.

“Maybe we’ll swing by later for some fun” she said placing a jar of honey next to the mug, knowing that I’ll need it to prep my throat. Long fast sets like the one I’ll have tonight were a no no smoke situation.

“Please do” .

She nodded and went to serve other customers, while I looked at my food. Jody and Donna’s cooking was delicious but I just wanted a damn drink, for pete’s sake!!

Damn it Chuck!!

I picked up the cutlery….

“ You’re really gonna use fork and knife to eat a burger?”

I straightened my back, my curls lightly bouncing, “What if I do?”

“That just no fun...” he said pointing at me with a fry before eating it and rubbing his hands together to shake off the salt.

He was right but still…

“Well….I ...shouldn’t” I thought about my pink lipstick getting smudged, and the terror in my mother’s eyes should she ever find out. He was looking at me confused, burger in his hands mid air and right then I realized that my mother's gaping image was what I convinced me to actually do it.

I put down the cutlery and picked up a tissue. Dipping a corner in the coke I rubbed it on my lips.

Now free from the lipstick menace I studied how he was holding his food and mirrored him, almost all the contents spilling out as I took a little bite.

He snorted and I glared at him.

We didn’t talk much while eating, but I did see him stealing glances around, taking in the place and how different he looked from the others boys who were actually on a date.

I could see he wasn’t exactly in his element and I wondered if he had chosen this place for me?

We were picking at the last of our fries and he looked bored.

“Why did you bring me here?” I asked, taking him by surprise.

The fry fell from his fingers, “What?”

“You are clearly not used to this” I said looking around.

“Isn’t this what are you used to?” he said bringing his glass to his mouth.

“...” you studied him and smirked, leaning in , “ Are you implying that I have lots of dates, Mr. Winchester?”

Coke must have gone down the wrong pipe.

“That...that was” he choked “ that was not what I meant” he pointed at me , patting his chest with his fist.

I laughed, loudly. More loudly than it was appropriate and immediately slapped a hand to my mouth, my eyes widening with surprise at my own lack of good manners. He smiled back, wide, the flush on his face making the green of his eyes shine.

No! Not shine! Sparkle!

“Why ...why don’t we do something you actually enjoy?” I asked earnestly.

He gave me a look.

“Oh, don’t be lewd!” I said feeling the heat crawl up my neck.

The waitress came back to clear the table.

“You sure you don’t want anything else? Last chance !”she chirped with fake enthusiasm.

I eyed the dessert section and raised an eyebrow at him. Getting my prompt ,he ordered a slice of cherry pie that we shared, and he enjoyed it way too much judging  by how fast he ate.

I eyed him suspiciously as he drove on non-asphalted streets, raising white dust everywhere. I had to tie a scarf around my hair preventing it from getting dustier.I tried to guess where he was taking us, looking around.

As if he could read my mind, he glanced at me and answered my unasked question.  “Relax!! I’m just going to my old man’s shop. Lots of witnesses, your virtue is safe,”

I scoffed at him, feeling embarrassed all of a sudden.

Once in front of the shop I snooped around as he disappeared in the back. I looked at the sign at the front, hanging over the dusty windows ‘ Winchester & Singer’s Auto repair and service’

I started humming the song from before, swaying on my feet , reading the other signs placed around.

“I thought that song wasn’t proper” I heard him, from a spot behind my back.

“You are right. It isn't !!” I turned around and froze.  Dean was pushing the motorcycle outside the shop, grinning.

“Is this not proper either?” He stopped beside me, looking down on me as I eyed the vehicle and then my skirt.

“It’s so not proper...”I whispered and then raised my glare to him, chin high, “... but as long as you don’t look and you don’t drive into town flashing my petticoat to everybody, it should be fine”

He smirked pleased and bowed slightly, hand on his heart, “ As you wish”. He straddled it, taking the kick-stand off the ground, and patted the space behind him. “Hell of a show, I’m sure”.

I opened my mouth outraged and I sat behind him, tucking my skirt safely under my thighs. As he started the engine I could feel it vibrating under me. This is absolutely improper and I felt a tinge of pleasure thinking again how my mother would have reacted if she knew. I gripped the sides of his jacket, the smell of leather and motor oil strong in my nose.

My small hands nearly got lost in there, trying to hold on to him. He chuckled and covered them with his leather clad ones, bringing them around his waist, squeezing them together tightly.

Looking at me above his shoulder he winked and we raised more dust as we took to the street again.

Dean POV

Maybe this wasn’t the best idea, I said to myself as I lean my bike to the side lightly, taking the hill’s curve slow and careful. Oh god, she’s squeezing me so much! I’m sure there will be an imprint of her fingernails embed in the leather. The dry hot air is messing up my hair as  I close my eyes enjoying it and the speed too, even if I’m going slower than usual.  This is what makes me feel alive.

Oh shit! Another tight curve.  I better stay focused, at least until I get her to the top. I take the next curve a bit faster than before and I hear her whimper even over the sound of the engine.

I chuckle. Well, at least she didn’t start hitting me to stop. Carefully I bring the speed up a bit more. Maybe I’m lucky and I get to reach the top before sunset.

Finally stopping I wait for her to get off, but she doesn’t budge, her arm still tight around me. Stretching my neck around, I see her face pressed into my back, her eyes squeezed shut.

Oh she’s adorable.

I clear my throat and she let me go immediately.

I already miss it. She gets off, clumsily, stumbling a bit and I grab her elbow to steady her.

She blushes and murmurs a thanks before brushing off dust from her skirt. She turns around, fingers undoing the tight knot of her scarf, slipping it of her hair.

I climb down the bike too, kicking down the stand and watch as she realizes where we are. I chuckle as she skips forward, stopping a few steps away from the edge and I follow her.

The wind is making her skirt flutter and her hair dance, carrying her flowery perfume to my nose. I tell her to be careful as she steps mor forward, one hand keeping the hair away from her face, the other involuntarily reaching back to me. I grab her elbow, as she bends her torso to look down.

I shift my gaze to the horizon already tinged by the sunset colours.All the purples and the oranges dancing together, blending, tinting the running clouds above us with colors that I don't even king the names of. The serenity and beauty of them in complete contrast to the danger of the cliff that spreads in front of us.

This might be the perfect place to impress a girl, but this is the first time I brought someone here. I look at her again frowning. This is my little hideout, and yet in merely hours of knowing her I already brought her here.

Why?.

She turns around to say something that I didn’t catch because all I can see is how her hair is hiding part of her face, eyes big and amazed ,smile as bright as the setting sun behind her. I can’t help the smile that grows on my lips and my feet carry me closer.

“...Dean”

Hearing my name I blink and focus on her voice “...uuhhh, what?” She tilts her head “I said, this place is gorgeous, Dean” she smiles softly, cheeks flushed in excitement. I really want to cradle them between my hands and kiss her.

WOAH….ok...ok...calm down, there.

“I’m glad”

She’s looking at me. No, she's scrutinizing me. I feel like she can see right through me. She raises an eyebrow, crossing her arms and shifting her weight on one leg.

Uh uh!

“So what number am I ?” she asks.

“Number?” I’m confused.

She blushes a bit but her gaze is sharper, “ How many poor girls have you brought up here to charming the skirts out of them?”

I scoffed.

“My lady ...I’m insulted!” I cross my arms, trying to keep a serious face, “This place is halfway from where I used to live and where your town. I’ve been coming up here my whole life and, on my honor, you are the first I’ve showed it to” I lean closer to her, almost looking at my reflection in her eyes and whisper, 

“ I wonder why”.

The blush increases as her eyes widen and look down.

“D-don’t call….” she raises it again, this time pointing her finger against my chest, “...don’t call me t-that”.

I shrug my jacket off while walking to the edge, and lay it on the dusty ground, sitting beside it, feet dangling off the precipice. I stretch my neck behind and pat the seat beside me.

She seems to think better of it but eventually steps closer, stopping right behind me, still away from the edge.

“D-don’t look” she orders. I raise my hands and look ahead until I hear the shuffling of fabrics. In the corner of my eye I see her feet. She has taken off her heels, coming in my range of sight. I peek a bit more and I see her trying to shuffle near the edge from an already sitting position. I bit my cheek trying not to laugh and look the other way.

“I told you not to look!” she whines embarrassed.

“I didn’t!!”

“Liar “ she huffs and her feet hang down near mine. I turn my head to say something snarky and I choke on my own words. Her skirt has  ridden  up on her right side and my eyes follow the curve of her leg up to where the stocking ends, the suspender of the garter belt showing, digging into her naked skin. My eyes linger there a bit before I cough and shift uncomfortably, looking up.

“Your, ehm…” I clear my voice “...your skirt rode up a bit ….”

I sense her fumbling in panic, and I choose for her sake, and honestly mine too, to forget it ever happened.

We stay silent for a bit , enjoying the wind that morphed into a light warm breeze as the sun lit the sky on fire.

She’s the first to break the silence.

“Why did you move here?”

I glance at her but she’s looking ahead , her feet rubbing together nervously.

“Needed a change of scenery...after my mother passed away” I blurted out, and I’m again surprised how easily I said that to someone I barely know.

“I’m so sorry, that must have been difficult”

“Meh, not really, we didn’t have that much to leave behind”

“...I meant your mother”

“Oh...yeah ...that” I know she’s looking at me now so I meet her eyes, “ Well, it happened years ago, but my old man needed money and time to open a shop with my uncle. Once that was settled we left those few things we had and came here some months ago”

“Months?” “I work there too and they need all the help they can get. I didn't want Sammy to help, and I left school so he could continue”

She stayed silent, and raised her legs hugging them,laying her head on her knees, those big eyes staring.

“You must think I’m just a hood with a motorcycle who dirtied your homework with my oil covered hands” I chuckle nervously, scratching the back of my head.

“It must be nice to earn your own money”, she sounded sad as her gaze fell on the now dying sun. “ ...you must feel free”

“...”

“ After finishing school my liberty is my father’s to do as he pleases”

“What do you mean?” She snorted and looked at me, “You are a man, you can do whatever you want. Me?...yeah I may be rich, but all that money is not mine. Think of it like a price on my head, to be sold to the best candidate. It’s a miracle they let me finish school before marrying  me off to some greedy bastard” She bites her lips almost ashamed.  “Sorry for the language”.

“... I like it , it’s a great contrast”

I manage to make her laugh, but it’s a bitter one.

“Here’s what you should do “ I said jumping to my feet, dusting off my jeans from the dirt and offering her my hand. She took it , standing up beside me.

“Scream!!”

“...what?”

“ No one here can tell you what’s proper and what’s not and I sure as hell won’t do it either”

I take a step back, giving her a little push “Come on, vent to the world, it doesn’t care anyway”.

I see the indecision passing over her face, before turning around, fists clenched by her sides.

“ I DON’T WANNA MARRY AN OLD  RICH DROOLING GEEZER!!!”

She takes another  breath

“ I WANNA EARN MY MONEY, AND …” she pauses and straightens her shoulders “I WANNA MARRY FOR LOVE” .

I see her stumbling as she took a step back , turning around and  I grin at her . She raises a finger and turns toward the horizon again .

“ FUUUUUUUUUUUUUUUCK “

The echo goes on quite a bit before I double over and laugh until my stomach hurts and I have literal tears in my eyes.

I see her approaching me grinning, her steps lighter.

“That..” I tried to say, wheezing “...that was awesome!! I think I will not be able to eat dinner.  My stomach hurts too much” I’m able to say before another fit of laughter shakes my body.

“DINNER?”

She looks at my watch and her eyes grow wide and panicked, “ ...Dang I’m almost past my curfew !” .

I watch as she slips into her shoes, tying her scarf around her head again and  I already hate it. She looks good with her hair messed up.

Ok Winchester! Enough of that!!

She grabs my arm and drags me to the bike “Get me home as fast as you can” she orders, her fingers digging into my flesh, her face panicked.

“Uh….you sure?”

“Better risk an accident than my parents’  rage”

I look at her horrified and she huffs rolling her eyes “ I’ll grant you another date if you bring me home in time”

“...oooh...so this was a date after all”

“DEAN…!!”

“Aye aye, ma’am” I said smirking, eyes focusing on the road ahead.

I drive fast, wind in my hair, and push it to the limit, just because she asked.

She’s gripping me tighter again, her face hidden in my back, her body pressed against mine and, lord forgive me, but she feels so good. I think she's even forgotten about the skirt and my mind is trying to imagine the way it flutters around her thighs. And now that I know what’s under it, it makes my blood boil. I grip the handle tighter and shake my head.  Focus, Winchester!.

I’m glad it’s dark once we arrived on the long, straight, lonely road that leads to my family’s shop. I slow down, check her watch and a low, relieved sigh escapes my lips. We are perfectly on time, and turn around to check on her .

I’m sure I freaked her out because I see that she’s trembling.

“You okay?” I shout over the rumbling of the engine. She raises her shaky head and I realize that she’s laughing.

She’s genuinely laughing. A big, fat,  loud laugh that's  brought tears in her eyes. That’s why they are shining. Those look at me and I’m sucked in, but it’s what she does  next that makes me really understand and accept  that I’m done for.

Y/N POV

This is too fun.

The speed, the wind that blinds me and cuts my breath, the smell of leather and motor oil, the rumbling of the bike that fills my ears. I can feel its vibration between my legs and it’s kinda hot and dangerous and is making me feel  all the things I shouldn’t feel.

I press my palms against him, and I can feel him like he’s naked , his abs are taunt and I feel them clench as he moves with the bike, following its movements. I should feel embarrassed of pressing myself to him so shamelessly. But, when we slow down on the deserted country road leading to the shop, and he turns around asking me if I’m okay I can’t help but laugh.

Because I don’t care.

Because I feel alive.

Because ….. I tug the knot of my foulard and, raising both my hands in the air, I let out a delighted scream as the wind slips it off my head.

Because I feel free.

“There, you can leave me here” I pat his shoulder and I stretch over the seat of his car retrieving my purse and books, “I’m just around the corner, across the garden”

“I should walk you to the door” he tries to protest.

“You want to be shot with salt rounds?”

“....no”

“Then here is good”

He quickly got out the car, making room for me to slide on the seat to exit the car.

“What are you gonna do about the scarf?”

“Foulard” I grin and produce a different one from my purse “ A ‘lady’ should always have a spare one” I mimic my mother’s tone. Before I could do it, Dean slipped it from my hands and gently wrapped it around my head. His eyes follows his fingers as they graze my face, pausing at my parted lips, before securing the knot tugging me to him, our face closing in.

He whispers : “Same time and place? This Saturday?”

I just nod , transfixed .

He let me go and I walk in a daze through my big house garden, the song from the diner still in my head. I’m in no rush now.

I start to sing softly.

Those cool and limpid Green Eyes A pool wherein my love lies So deep that in my searching for happiness I fear that they will ever haunt me All through my life they'll taunt me But will they ever want me

I know  my night will be spent dreaming of green eyes.

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