The day goes on normally as Dean types on his computer, takes some calls and have meetings. (Y/n) would come in every now and then with some papers for him to sign and she would file in some paperwork and type on her computer.
"Net profitability aside, it's the client-retention rate that concerns me vis-à-vis maximizing return on sales. Buzz me back once you've seen the spreadsheets." Dean said into his headset but he kept staring over at (y/n) as she worked.
Then Mr Adler walks in and Dean takes off his headset and walks up to him. "Mr. Adler." Dean greets. "Dean." Mr Adler said as he slaps Dean on the shoulder. "Good stuff." he said. "Good stuff?" Dean asked. "Big things. Good stuff." Alder said and Dean smiles. "Good stuff." Dean said and Adler looks over at (y/n) as she continues her work.
"How's the new assistant treating ya?" Adler asked Dean. Dean looks over at (y/n) and a small smile appears on his face. "She's good. Great actually." Dean said and Alder notices the smile. "Oh I bet she is, you sly dog." Adler said as he, playfully, slaps Dean's shoulder then chuckles.
Later, that evening, Dean was sitting at his desk with his headset on, talking into it, as (y/n) walked in. "Oh I hear you. No, I haven't been to the gym in ages. Carrying a little bloat around myself. It's a sedentary lifestyle, my man, no two ways." Dean said as (y/n) places another set of paperwork on his desk. "All right, tell me one more time. You said lemon and—what was it? Cayenne and maple syrup, are you serious? How much did you lose?" Dean asked the person at the other end and (y/n) chuckles and shakes her head at this.
"Really? Okay, well I might have to give that a try. Okay, we'll talk later." Dean said and he takes off the headset. “Trying to lose weight?” (y/n) asked, curious on why a man that look like that would be concerned about his weight. “Not really. But it wouldn’t hurt to takeoff a few pounds.” Dean replied, picking up one of the sheets of paper she set down, skimming through it.
“Well, if you ask me, at least I hope I'm not over stepping here but, I don’t think you need to worry about that.” (y/n) said, as Dean glanced up from the paper. “Oh really?” He asked, the corner of his lips slightly turning upward. “Yes, I think you look great.” (y/n) replied. “Well thank you.” Dean said, smirking and setting the paper back down.
“If I were to say, you had a good body, would you hold it against me?” He asked, raising one of his eyebrows. (Y/n) was surprised by this sudden question, then laughs. “Mr. Smith, are you coming on to me?” She asked, trying to sound serious but the smile was slowing forming in her lips. Dean smirks at this response and shrugs. “Depends, is it working?” He asked, (y/n) laughs again. "Maybe..." she said and they share a smile.
"So...how did your first day go?" Dean asked her. "Well it was better than this morning, I can tell you that." She replied to him. "Well, I hope I wasn't being a, uh...hard-ass on ya." He said. “No at all. I’m sorry, I misjudged you.” she laughs. “Apology accepted, on one condition…” Dean said and (y/n) eyes him, suspiciously.
"And what is that?" She asked him. "I take you out for coffee." He said and she chuckles. "Going on a date with the boss? So scandalous." She said, a bit with a laugh in her voice as Dean stands up and walks up to her. "Well, then we won't call it a date. We'll call it a getting to know each other meeting." Dean said, as he stands in front of her, and she laughs at this. "Do you say this to all of the assistants?" She asks, an eyebrow raised. "Only the pretty ones." He replies and she blushes at this.
"Well, you drive a hard bargain, Mr Smith." (Y/n) said and she thinks for a moment then looks at him as he looks at her. "Okay, I'll accept your meeting." She said and Dean smiles. "Cool, how about after work?" Dean asked her and she nods. "I'll see you in the morning, Mr Smith." (Y/n) said and she turns to walk away. "Goodnight, Ms Remington." Dean said as he watches her leave the room while smiling to himself.
YOU ARE READING
Supernatural (Dean Winchester x Female!Reader)
Fanfiction(Y/n) (l/n) was trained by her father, who was a well-known monster hunter before he settled for the apple-pie life, after the death of her mother when she was very young. Now in the wake of her father's death, (y/n) has been going solo on the whole...
It's A Terrible Life
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