Imagine your boss, Dean Winchester, flirting with you every time he can.
“And last but far from least-” you let a small sigh, looking at the door in case someone was coming “Mr Fury asked to see you.”
“Fury? As in Nick Fury?” Dean raised and eyebrow, his interest peaking.
“Exactly. It either has to do with the damage you and Mr Stark caused on your small trip around town or-”
Dean chuckled, leaning back in his chair “Come on (Y/n), we were drunk!”
“That does not justify it. On the contrary, it was reckless to go take his suits while being drunk.” you said with a pointed look and his smile turned into a softer one.
“You know-” he leaned forward so that he was closer to you “I love it when you care so much about me.”
“Mr Winchester.” you scolded softly, not meeting his eyes but still unable to hide a small smile from your face.
“I thought that by now we had agreed on that, sweetheart. It’s Dean.” he said, sounding a little disappointed.
“You know that can’t happen, Mr Winchester.” you mumbled, starting to place all of his files in place. Anything to keep you occupied from looking him in the eyes “I’m your assistant.”
“Well then we can arrange that. I could always fire you.” he gave you a cheeky grin as with wide eyes your head snapped to him.
“What?” you stood there frozen for a second until he started laughing at your expression.
“Just kidding. There’s no way on Earth I would fire my most trusted worker.” he shook his head “Besides, this enterprises would crumble down without you here to be honest.”
“Glad you appreciate my job then, Mr Winchester.” you chuckled with a small sigh of relief, shaking your head at your boss.
He rolled his eyes for a moment “That’s just not going to go away easily, is it?” he huffed, almost disappointed and you bit the inside of your cheek; still not looking at him.
“Wish it could.” you mumbled and saw him from the corner of your eye get up and walk towards you.
“You know it can-” you almost jumped at how close he had gotten without you realizing it, his breath only fanning over your cheek and his hand on your back “It’s all up to you.”
“Mr Winchester please-” you glanced at the door nervously “Someone might walk in. I just- I don’t want them to think I am taking advantage of-”
“Of who? Me? Sweetheart by all means, do so.” he gave you a boyish grin and you couldn’t stop a chuckle at his words, shaking your head.
“No. Of the time I spend with you. I- I worked hard to get this position.”
“I know, I saw it for myself.” he frowned slightly “That’s why you got the promotion.”
“Yeah, well if they see us like this they’re not going to think exactly that Mr Winchester. I don’t want people to assume I am here because I am sleeping with my boss.” you placed a hand on his chest, regretting it but still pushing him away. You couldn’t even dare look him in the eyes, you couldn’t take the heartbroken look on his face.
“But they don’t have to see us, if that’s the problem.” he suggested after a long pause and you frowned.
“I mean if that’s what you’re most scared of- we don’t really have to tell everyone. Let them find out on our wedding day.” he added with a wink and you couldn’t help but giggle at him.
“Mr Winchester-” you started with a small whine but you knew you didn’t have an excuse good enough. Honestly you were mostly trying to convince yourself that you couldn’t be with him than him in the first place. Besides, it was your own feelings you had been battling with mostly these days than your boss’s advances and flirty remarks.
“Come on, just give me a chance. You’ll see I’m not that bad!” he threw his arms in the air and you bit your lip.
“Mr-” you stopped yourself “Dean, I know you’re not.” you confessed looking him in the eyes “And I know that if the circumstances were different- I wouldn’t have hesitated for a second. Especially after such a surprise.” you added with a chuckle and he grinned.
“You like them?” he remembered the flowers he had sent to your apartment. One of his many attempts in getting you “Took my brother’s advice in it.”
“The flowers were amazing, really.” you admitted “But I was mostly referring to the sweets, especially the pie.”
“Well, that one was my idea actually.” he confessed, full of pride and you giggled.
“Oh I bet!” you shook your head with a laugh.
“Say-” he spoke up, a hand again being placed on your back “How about I take you out… for pie and burgers and we can make a fresh start?”
“Dean” you sighed “You’re not going to give up, are you?”
“Hell to no.” he confessed.
“May I ask you- why are you so interested in me? Up until a few months ago I was just one of the secretaries until I became your personal assistant. But still- nothing more.” you dared look him in the eyes, only to see confusion written all over his face.
“I think we’ve made it clear that you got this position because you are the only one that actually puts effort into their work. Plus, you’re the only one that knows me so well and doesn’t dress up on purpose to show off and turn me on.” he shrugged, before pressing you close to him “That happens either way.” he added and you rolled your eyes at his cheekiness.
“I’m only wearing a white blouse and pencil shirt.” you mumbled.
“As I said- too fucking hot.” he growled almost in your ear and for the first time you let him kiss your cheek without you pushing him away.
“Dean” the way his name left your lips was definitely something you weren’t planning on.
Dean grinned widely “See? Already getting there-” he licked his lips “Do you really want to know why I am so interested in you?” he said in a low rough voice “Because you’re special. Because every morning you have walked in my office, hair a mess, no make up on and clothes a little a little wrinkled with a few buttons undone-” he paused for a moment, his eyes roaming your body “I can only think of how gorgeous you look, and how I’d love to see this sight every fucking morning. Especially after an intense night of-” he paused grinning up at you, only to see a hint of red on your cheeks.
“Gosh I would so love that.” he breathed out huskily, his breath tingling your lips as his face stood only a few inches away from yours.
“I’m- I’m not that-”
“I swear to god, if you complete that sentence I am just going to grab you and prove you wrong right here and now in any way you can imagine.” he said with a slight growl and you swallowed the lump in your throat, feeling yourself shiver when his hands started traveling. You couldn’t deny you liked it a little too much.
“Do you even know the things you do to me when you lean over my desk?” he whispered, resting his forehead on the side of your head; his lips brushing past your ear “With those tight, black skirts. I’ve had such a fucking hard time concentrating during meetings just because of you. You don’t even have to touch me, hell not even say something and I know I am a goner. I can’t think straight when you are in the same room. And gosh, you’re not even doing it on purpose. You’re so clueless.” he grinned “So adorably clueless.”
“Mr Winchester” you whispered, fisting his suit jacket in your hand.
“And the way you say that- I hated it so much at first, it felt like you put a wall between us. I still do but at the same time-it sounds so innocent, so unintentional that you can’t realize how cute and hot it sounds at the same time.” he chuckled and you bit your lip.
“And as if all of that is not enough you- you are such an amazing woman. You actually listen to me when I need it, you try to understand me and you- you love rock too. You listen to me ramble about my car when my own brother always tries to make me shut up when I do. You actually know so much about me, every side of me, that no other woman I’ve been with has ever known. And that’s only because you are the one interested.”
“I can’t help it you know.” you whispered, looking at him through your eyelashes.
“I know. Trust me baby, I know.” he breathed out, cupping your face and before you had the time to react he crashed his lips to yours.