StoneyGGirl ❤️ @stoneyggirl - Tumblr Blog

A/N : Hey, y’all. I’m back with a story that is fluffy and sweet and it was written for a Galentine’s fic exchange on Discord so with a little bit of editing it’s here too. Most of you know know that fluff isn’t my go to type of story but I have to admit that I quite enjoyed writing this one. I would also like to submit this for @supernatural-jackles “Tell me a story” Bingo filling in my ‘First date‘ square.

Pairing : CEO!Dean x Reader.

Characters : Bobby Singer, Charlie, Benny Lafitte, Mick, various bystanders.

Summary : Most of the times, what you're looking for is staring you right in the face.

Warnings : self doubt, body issues, insecurity, Dean in suits ( always a warning in my book ), generous amounts of fluff.

Words : 5263

The original story was beta’d by the super awesome @winchest09 and I can’t thank her enough for everything.

The pic for the banner was found on Pinterest and the dividers are by @talesmaniac89 and @firefly-graphics

Enjoy, my lovelies.

The busy streets of the city are flowing by your cab window as you are nearing your destination. People are rushing to get to their jobs, to catch the next train or bus, to take a quick break from their schedule and maybe just look up to the sky for a shot of energy that will help them pull through. You’re sitting in the back seat and you are looking at everything that’s passing you by without really seeing it. Your hands are squeezing the folder that’s been resting on your lap so tightly that your knuckles have turned white in a desperate effort to look calm.

You still can’t believe that you had applied for the position of personal assistant for the president of “WinchesterAds”, a prestigious advertising firm that everyone who was in this kind of business would kill to have the chance to work with. You have to admit, though, that if it hadn’t been for Charlie pestering you day in, day out you wouldn't have sent in your CV. Charlie is your best friend, roommate and cheerleader. She believes in you more than you believe in yourself and you can still remember how she had burst into your shared apartment, waving the classified ads section of the newspaper in the air.

“Υ/Ν, this is it. This is your big chance,” she yelled enthusiastically and plopped herself on the couch next to you, almost shoving the newspaper in your face.

Pulling your head back a little, you turned and looked at her. She was beaming, pointing with her head for you to look at the paper. You sighed, fully knowing that when she was like that, there was no alternative than doing what she wanted. Even if it was only to get rid of her. Right there, in the middle of the page, was a big red circle that enclosed the coveted classified. You read it very carefully, realizing that Charlie had indeed found the perfect ad.

As you were going through each of the job requirements listed, you mentally checked in your head if you had them and you were very happy when you had ticked them all off. But the small smile that had formed on your lips quickly vanished when you got to the end of the ad. ‘Please send a detailed CV to WinchesterAds…’ That was when you had stopped reading. Getting a job there was almost impossible because apart from the qualifications you needed to have, the standards were extremely high. Rumors around this firm were that they only employed the best of the best, even for the lower positions and the workload was always huge. You weren’t afraid of the amount of work because you had always been very efficient but on the other hand self confidence, especially when new things were involved, wasn’t one of your strong suits. So although you knew you had all the qualifications, your own self doubt was whispering in your ear that you couldn't do it.

You opened your mouth to speak but before the first sound came out, Charlie raised her finger and stopped you. “No, no, no. You are not chickening out of this one. You are going to send your CV and I’m willing to bet my life that you will get the job. So, get your butt over to the computer and send it right now!”

“But - ” you tried to protest but she was already pulling and pushing you.

“No buts. What's the worst thing that can happen anyway? They won’t hire you. But then there's the other option. That they will.” She had already pushed you to the small desk in the far corner of the apartment and sat you down in front of the screen. “Imagine working there. Imagine having their name on your résumé. That name could open any door for you, Υ/Ν.”

You looked up at her still beaming face and you sighed in surrender. You knew she was right. There was nothing up your sleeve to contradict what she had said so you clicked on the word document that was your CV. You went through it very carefully and when you were sure that it had everything, and that it was written in the appropriate style, you opened your mail. With trembling fingers, you added the address of the recipient. Then, taking another deep breath, you attached the document and while biting your lip you pressed ‘send’.

“That’s my girl!” Charlie clapped and hugged you as you were still sitting and regretting your decision.

“We’re here Miss,” the taxi driver announces, pulling you out of your own thoughts. Smiling, you let go of the folder, allowing your fingers to relax a little as you searched through your purse to find the money for the fare.

“Good luck,” he adds, as if he knows how much you are going to need it and you nod a little before exiting the vehicle. Standing at the curb, you raise your head and take a look at the huge glass building. Your eyes travel all the way up and stop at the simple, steel letters that form the name of the company.

What are you even doing here? Your brain is whispering to you but you momentarily close your eyes and hear Charlie’s voice from this morning. You got this babe. Go kick ass and take names. Commanding your legs to move, you take the first step and slowly edge towards the entrance. The doorman tips his hat and opens the heavy glass door for you to enter. ‘This is it. Last chance to back away.’ The stupid little voice in your head says but you grit your teeth and tell it to shut up as you step inside and move towards the big reception area.

A polished wooden semicircular desk almost hides the four young women who are sitting behind it, wearing headphones, quickly typing on computers and answering phones. You approach the first one and you can't help but look a little harder as you realize that not only her but the other three receptionists look like models. Dressed immaculately, with beautifully made up faces and hair pulled back into tight buns. Their clothes are crisp and cling to their bodies in a perfectly tailored way. Although you can’t see them completely as they are all seated, you are sure that they are all size zero and hesitantly you look down at your skirt and shoes. You have never been a size zero and that was something that had always troubled you, but you had managed to find a few brands that carried clothes for women who were more curvaceous so you were always well dressed and chic. Deep down, though, you wished that one day you would wake up and miraculously be like one of the girls in the high fashion magazines Charlie usually buys.

“Good morning. How can I help you?” The first receptionist asks, smiling her customer service smile at you and you clear your throat.

“Μy name is Y/N Y/L/N and I have an appointment with Mr. Singer for the position of personal assistant.” Her eyes very quickly roam over you and you fidget a little, shifting your weight from one leg to the other.

“Uuhhmm, yes-” she replies and checks her computer. “Take the fourth elevator and head up to the seventh floor. Mr. Singer will see you shortly.”

You thank her politely although you are not sure that she has heard you as her attention is back on the computer screen and to the next caller who’s talking to her through her headphones.

You mingle with the people who are heading towards the elevators and taking the fourth one like the receptionist had instructed you, you press the button with the number ‘7’ on it. But right before the doors shut, they open again and a tall, sharply dressed man enters. In the fleeting seconds it took him to get in, you managed to see him very clearly. His hair is short, very well groomed and styled apart from a single tuft that falls on his forehead, somehow ruining but at the same time making his whole appearance better. His dark grey suit jacket fits his frame perfectly accentuating his broad shoulders and his narrow waist. His trousers are tighter than the classic suit trousers and end right at his expensive, leather shoes.

“Good morning, Mr. Winchester.” The man standing next to the elevator entrance says and you feel like the air has been knocked out of your body. That was the man who is, if everything goes well, going to be your future boss. A fucking male model.

“Holy shit,” you whisper, as you swallow the lump in your throat and hope that no one has heard you.

“Good morning, John,” he answers, nodding his head towards the man.

Never before has an elevator ride taken so long. The floors ping away as if they are in slow motion and you are silently counting them. 1,2,3… 7. Mr. Winchester exits first and then many people follow, last of all you. You wait for a few seconds for the men and women to disperse, then walk up to another reception area which is again occupied by two equally well dressed and beautiful women. What is it with this place? Is everyone required to go through a casting session before they can work here? Why are they all so perfect?

You repeat what you had said to the previous receptionist and she immediately gets up from her seat and escorts you down a wide, well lit corridor. Her heels are clicking on the white marble floor and you can't help but notice how her hips sway under her tight skirt. “If this place indeed casts their employees, you have zero chance of ever getting this job.”

Your brain just won't shut up today. She stops outside a dark wooden door and you manage not to bump into her at the very last moment as she softly knocks and waits till a voice is heard from the other side. She opens it for you to walk through and you do so, thanking her politely. But you haven’t taken two steps when you freeze to your spot. The large office has floor to ceiling windows that allow the sunlight to seep through making the heavy, wooden furniture shine. On the wall to your left there are six TVs showing different channels ranging from the stock market and various news shows to advertisements and places around the world. But none of those things are what render you immobile. It is the beautiful, broad frame of the owner of the company who is standing with his back to you, looking out one of the windows.

“Ms Y/L/N, come in,” a voice from your right says, snapping you out of your trance and making you remember the reason you are here. Praying that the signal from your brain will reach your feet, you sigh in relief when you feel yourself move towards the older man who is already standing from behind his desk, extending his hand to you. “I’m Mr. Singer. Please, sit down,” he continues, motioning for you to sit. You shake his hand, stealing glances towards the other man in the room who hasn’t said anything yet and you sit in the big leather armchair across from Mr. Singer.

“Your résumé is really impressive, that's why we have asked to see you in person,” he begins, “Me and Mr. Winchester-” he continues and the other man is now walking towards the desk and leans over the older man to look at something on the computer screen and then at you, “-are always interested in having the best colleagues and associates in our firm. We offer a wide range of benefits to our employees and I’m sure that you know that working here is something that very many people strive to achieve.”

You nod your head in agreement and you look from Mr. Singer to Mr. Winchester who is now leaning against the wall behind the older man with his arms crossed over his broad chest.

“In return, of course-” he goes on, “-we need the people who work for us to be trustworthy, ready for long working hours as most of the time there will be difficult projects that need sharp minds and quick decisions.”

You continue nodding your head because for anyone who was in your line of business all those things were already known, plus no actual words could find their way out of your mouth.

“Ms Y/L/N,” Mr. Winchester begins and the sound of his voice feels like a warm blanket on a cold winter’s night. Like a sweet piece of chocolate that’s slowly melting on your tongue. It's deep and a little gravely and you can’t help but wonder how all those women in here manage to get any work done with this man breathing the same air as them. “I personally reviewed your CV and asked Mr. Singer to bring you here for an interview. You seem like a person who knows exactly what you’re getting yourself into-” he pauses and smiles a small smile, looking at you carefully, probably trying to assess if you understand what he’s saying, “- and if that’s the case, I will expect to see you back here, Monday morning at nine sharp.”

You aren’t sure what has just happened and you keep staring at the tall, handsome man until Mr. Singer gets up from his seat and extends his hand once more to congratulate you on your new position. “Welcome aboard.”

Six months later

The last six months flew by so quickly. There were so many things you needed to learn. New and difficult things. The pressure was immense and whatever you imagined you were going to have to deal with, was simply an understatement to the reality you had walked into. The workload, the projects, every single detail that had to be checked and double checked before a rough draft was even examined by Mr. Winchester, the appointments, the meetings. It was just too much. But instead of all this pressure making you feel frustrated or scared, it has actually made you want to succeed even more. Because every time a project went through, every time a small detail was caught before it reached a potential client, you were rewarded with a warm smile from your boss accompanied with “Excellent work, Y/N”. Although neither of those things could be considered as great, they made you feel very special.

After the fourth month, Mr. Winchester had insisted you call him Dean and if you have to be honest with yourself, you are still struggling with that. In the long hours you have been working together, you very quickly came to realize that he is a fair boss who recognizes and values the people who work hard. And very often, when the workload kept you in the office late, he would personally order food or coffee for the much needed energy boost.

Now six months in, you are accustomed to the speed with which stuff needs to be done, with the demands, with the endless working hours. What you aren’t accustomed to yet, is not being affected by him. The green of his eyes that seem to not just look at you, but stare into your soul. His plump lips that look so soft as they crook up into a side smile that makes your knees weak. The way that he bites the tip of his tongue when he’s deep in thought. His presence that dominates any room he walks into. The way he praises you for your good work and makes you feel so special. Very often, on your lunch break you picture him, taking you in his arms and kissing you slow and sexy while the sun is setting behind you like they do in all those rom-com movies. Or dancing with you, both dressed in expensive evening clothes in a private room of a restaurant while the music is playing just for you. But he doesn’t look like the kind of man who would be into chick flicks, and you are not the woman that he would be with even if he were. You have seen the kind of girls that come by his office to escort him to galas and functions. You have answered phones and made arrangements for them on multiple occasions. Saying that this man is out of your league isn’t just an understatement, but an understatement to the understatement.

Luckily, though, you have managed to keep your daydreaming limited to your lunch break and haven’t let it affect your work. So here you are, another Thursday that you are still in the office after seven in the evening, going through next day’s schedule and wishing for a way to get more coffee teleported to you, when you hear the glass door that separates your office from Dean’s open. You raise your head just as he’s exiting followed by his best friend Benny.

Benny is also one of his financial advisors and he can be found on your floor more often than on his. Dean is holding his suit jacket in the crook of his arm and he’s lowering the sleeves of his crisp white shirt. His tie sits undone on his chest and the two top buttons are open, leaving a small patch of skin visible. He abruptly stops when he sees you still at your desk, making Benny almost crash into his back and smiles that heart stopping smile of his.

“Y/N, you still here? Your boss is a cruel man, I tell you,” he chuckles as he moves closer to your desk.

“Sometimes,” you respond, offering him a smile.

“I told you man,” Benny starts, winking at you, “I don't even know how you managed to get things done before this gem started working here.”

“You’re exaggerating, Mr. Laffite but thank you,” you reply, bowing your head just a little, mimicking a small curtsy.

“I hope I’m not interrupting,” Dean says as he’s putting on his jacket and before you even attempt to answer, he continues. “So, all set for Saturday evening, right?”

You frantically try to remember if he has asked you to make any kind of arrangement for Saturday, and you’re a second away from having a panic attack because your mind comes up blank. The confused look on your face makes him realize that you don’t, in fact, know what he’s talking about.

“The company’s annual party. It’s this Saturday. I can’t believe I didn't tell you. I can't believe that nobody told you,” he continues, a hint of regret and sadness in his voice as his eyes dart back to Benny in an attempt to somehow place a small part of the blame on him.

Benny, who unphased by the whole situation, is smirking and is not even trying to hide it. “It’s gonna be held here, at eight,” he adds. “You must come.”

“Uuuhhmm-” you start but you soon realize that you have nothing to say. Attending parties has never been your thing, mainly because you more often than not end up screaming over a mountain of clothes you don't think suit you, but also because in this case you simply don’t want to walk into this place alone.

“No ‘uuuhhhmmms, buts or maybes,” Dean says. “I realize that it is kinda short notice and all so imma do the noble thing and give you tomorrow off so you can go shopping or do whatever you want. But-” he retorts, raising his long, thick finger, “- you must be ready by seven thirty. I will send a car for you.” And with that, he pats Benny’s back to make him move and they both disappear towards the elevators leaving you alone, wondering exactly what the fuck had just happened.

Thirty minutes before, in Dean’s office

“So, are you bringing Jo to the party?” Benny asks Dean as he’s pouring himself a glass of whiskey. Dean looks up at him, taking his eyes off the computer screen and sighing heavily.

“I don't wanna bring anyone to the party. Hell, if I weren’t the boss, I wouldn't even attend it,” he replies, getting off his seat and walking slowly towards the huge floor to ceiling windows.

“Trouble in paradise?” Benny inquires, downing his drink in one gulp.

“Paradise?” Dean snorts. “I swear man, I’m so fed up.”

“With Jo?” The other man asks again.

“With Jo, with Lisa, with all of them. I just can’t talk with them about anything serious or important. All they care about is going on trips, getting presents, and being seen on pages of glossy magazines. I’m sick and tired of it, Benny.”

His friend goes to stand next to him, his hands in his pants’ pockets as his eyes are looking down over the lights of the city. He doesn’t say anything for a while, probably thinking that Dean has more things to share. When a few minutes pass in silence, he turns to his friend and pats him on the back. “Then maybe you should start looking for women who are worth your time and your intelligence, my friend and not just women who want to be eye candy. Look for someone you can have an intelligent and stimulating conversation with, someone you won’t be scared of what could come out of their mouths.”

Dean turns his head and looks at his friend, a bitter chuckle escaping his lips. “You know where I can find one of those? Because it seems that for the last few years, luck hasn’t been on my side.”

“That’s because you're looking in the wrong place, dude. If you open your eyes, you will see that what you're looking for isn’t too far away.”

“What do you mean?” Dean asks, his eyebrows knitting together as he tries to figure out what his friend is saying.

“Man, I swear if it weren’t for your looks and money, you would wind up alone,” Benny replies and points with his head towards the door.

“Who? Y/N?”

“You bet your ass, Y/N. She’s freaking intelligent, she knows how to talk and she’s capable of dealing with anything you throw her way. She’s hella cute and her eyes have that constant sparkle very few people have. Plus, her commitment to her job goes well beyond her duties and the fact that you haven’t realized why she does what she does renders you a bigger idiot than I thought you were.”

Dean is listening carefully and little by little his eyes grow wider like the pieces of a puzzle he didn't know he wanted to solve have fallen in their right place.

Y/N. His assistant Y/N who he could always count on for everything. Whose wit and knowledge are invaluable. Who knows what he wants before he even thinks of it himself. Who has saved and prevented many mistakes from happening. Whose input and ideas have many times proven to be more clever than many other, higher ranking people in the office. And just like that, he knows.

“Let’s go,” he almost shouts at Benny as he grabs his jacket from the back of his chair and opens his office door.

Saturday evening

You check the round wooden clock that’s hanging over the tv, trying to make sure that its hands are moving because you could swear that instead of going forwards they seemed to be immobile. You are dressed and ready but if anyone asked you why, you wouldn’t be able to give them a proper answer.

‘I’ll give you tomorrow off,’ he had said, and you didn’t know how to process or work with that information. Thank God, Charlie had stepped in once again after you had explained to her what had happened at the office in vivid detail. She had dragged you out of the house and made you visit almost every clothes and shoe shop she knew. You had ended up purchasing a lovely, silk, black dress that wrapped around your upper body perfectly and then flowed over your hips, stopping just under your knees. A pair of strappy black sandals that hurt your feet even just by looking at them completed your simple yet elegant look. Charlie had also helped you style your wavy hair and applied your make up for you, ensuring that your pretty eyes were accentuated. A bold red lipstick was the final touch and you couldn’t help but admit that when you looked at yourself in the mirror, you were very pleased.

Very many things still didn’t make sense in your head, like why he would go to all that trouble just so you could attend the party. Give you the day off, send a car for you…although everything is extremely kind of him, it goes well beyond what a boss would do for his employee.

Just as you are about to replay what had happened in your head, the doorbell rings. ‘Holy hell, this is it!’ Your inner voice whispers and you feel as if your feet are glued to the spot. A second, more persistent ringing jolts you into motion and answering it, you hear Mick’s voice telling you to come down. Mick is Dean’s driver and it seems like he’s on call 24/7. You let him know that you are on your way and grabbing a small purse, plus your phone, you turn off the lights and head to the elevator before you think about it again and end up changing your mind.

The big, black SUV is waiting at the curb right outside your apartment building and when Mick sees you, he rushes to open the back door, greeting you politely. You get in and fasten your seatbelt mechanically as Mick climbs back in the driver’s seat. Looking outside your window, you realize that your mind is just a blank sheet of paper, which is a welcome change from the frantic overdrive it has been all evening. But after a few minutes you see that the car isn’t heading to the office but has taken a completely different direction.

“Is this a new route, Mick?” you ask, still looking outside.

“Mr. Winchester has asked me to make a stop before we get to the party, Miss. Don’t worry, we’re going to be there in no time,” the driver says, looking at you through the rear view mirror.

You settle back in your seat but very soon the car pulls up outside one of the fanciest, most expensive restaurants in town, and Mick is quickly opening the door for you. The confused look on your face speaks volumes and when the driver extends his arm to help you get out, you take it in hope he will reveal just what is going on. The porter opens the restaurant door without asking anything, tipping his hat at you and you are immediately escorted through the rows of tables to a more secluded part of the establishment. A waiter standing there motions for you to enter and Mick bids you goodnight and disappears. Moving further in, you see a small round table with two white candles illuminating the small, yet elegant space and a bouquet of flowers between them. Champagne is chilling in a cooler and soft music is heard from the sound system, making the noise from the rest of the restaurant disappear. And then, you see him.

Dean is right there, dressed in an elegant, dark blue suit looking so handsome and dapper. The minute he sees you, he moves closer and takes your hand in his. He kisses it softly as he escorts you to one of the chairs and helps you sit. Everything feels as if it is a dream, as if you are a bystander watching an intimate scene and not as if you are living it. He pulls the chair that is opposite yours and brings it right next to you, taking your hand in his again.

“Thank you for coming,” he says softly and his eyes are warmly roaming over your face, making your knees weak. “I’m sure you must have a ton of questions and if you give me five minutes, I will try to answer all of them.”

You look into his beautiful eyes that are shining with excitement, his lips that are curving up into a mischievous smile and inhale his scent as he’s sitting so close to you, making you dizzy.

“You know, Y/N-” he begins, his thumb rubbing slowly over your knuckles, “-there are so many things I wanna say to you but right now it feels like my head is completely empty.” He lowers his head a little and takes a deep breath as if he’s collecting his thoughts. Without really knowing where you got the courage from, you raise your hand and place it on his cheek, letting the light stubble delightfully scratch against your palm. When he feels your touch, he raises his head and smiles.

“Sometimes-” he starts again, “all we need is for someone to grab us by the shoulders, shake us up and steer us in the right direction. Help us see.”

“See what?” you ask, your heart beating loudly in your ears, uncertain of what is coming next.

“See that-” he tries but stops again. “Damn it. I’m a full grown man who acquired the ability of speech when he was a year old and now I can’t even put two words together. What I really want to say is that for the last six months, you have been the reason I wake up in the morning, the reason my heart feels lighter. When I walk into the office and see you there, biting your pencil between your teeth with your cheeks flushed and your eyes sparkling with excitement from succeeding in your work, I realize that what has been missing from my life is you. That’s why tonight I didn't want to share you with anyone else, I didn't want to waste one more evening among an uninteresting crowd. I wanted to have you all to myself to talk to, to stare at, to touch.”

Not sure if you have understood what is happening, you keep staring at him. He slowly moves his head closer, his lips stopping an inch from yours.

“I’m in love with you,” he whispers and lightly kisses you. Your whole body is set on fire, a million goosebumps prickling your skin and you surrender to his kiss. A slow, sensual kiss that neither of you want to end. After a little while, he reluctantly pulls his head back and his eyes fall on your lips, delightfully wet and swollen by his assault. “My God, you're so pretty,” he hums. “Tell me that-” small kiss “-you feel just-” small kiss “-even half-” small kiss “-of the things I feel.”

“Dean,” you breathe, “How is it possible for you to have seen all those things and not know the answer to what you have just asked? I love you. I have loved you since the minute I saw you in the elevator on my first day there.” You are surprised at how steady and even your voice sounds. “I’m yours, for however long you want me to be.”

“Forever it is then,” he replies and his lips find yours once again.

Thank you all for reading and if you wanna make my little black heart happy, you can always share your thoughts with me HERE.

LOVE, ZEE

@ain-t-bovvered @dean-winchesters-bacon @cosicas-cuquis @idreamofplaid @waywardnerd67 @ladywinchester1967 @babysimpala @katbratsupernaturalwhore @akshi8278 @hobby27 @adoptdontshoppets @princessmisery666 @destielhoneybee @flamencodiva @msmarvelouswinchester @treat-winchesterswith-kindness @asgoodasdancingqueen @mvdeanw @charred-angelwings @pink-sparkly-witch @petitgateau911 @kickingitwithkirk @themoonandotherslikeit @b-i-t-c-h-i-e @sweetness47 @b3autyfuldisast3r @shawnie74 @ackleholicwinchester @lyarr24 @icequeen6666 @colewrites @mogaruke @deanwanddamons

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