This imagine features Boss!Jensen, fluffy and what not. It's not like those usual ones with the intense relationships between employee and boss.

🎶: 'Hiding My Heart' covered by Adele

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'Ackles Enterprises'.

One of the largest conglomerates out there. They practically own everything. The food you eat, the appliances you use, the water you drink... hell, even the electronic device you're using right now is made by one of their subsidiaries.

You'd assume that the boss is probably this greedy and arrogant douch-bag, like how it usually is, the clichè.

However your boss isn't that bad in-

"Hey [y/n], Mr. Ackles wants these up to his office," Rebecca told you and dumped tall pile of sheets into your arms. They're  heavier than they looked and you stumbled a bit. On top of that, she placed a coffee mug, a coaster underneath, on top of the stack.

"Thanks [y/n/n]!" She smiled with her teeth and walked off. You hugged then blew the strand of hair out of your face, though regretted it when the coffee mug threatened to fall over and spill over the documents.

You made your way up the elevator and to Mr. Ackles' office on the 18th floor. The view was amazing and you're thankful that he hasn't caught you staring out of the windows.

You're Mr. Ackles secretary but it isn't that boring or that... entertaining either. You have no relationship with your boss, just colleagues, though you always wonder if you'd be in some sort of boss-and-secretary affair...

"Hey [y/n], Jackson is really upset about you not replying to his email," Robert, one of the sales members, told and you frowned. To your horrible luck, you ran into Jackson a few metres ahead.

"HEY! You think you're the boss's secretary so you can get away with anything? You know how much this will cost us?!" Jackson yelled, but not enough to make a scene.

"I-I-"

"Make sure this doesn't happen again, otherwise I'll have a word with your employer!" He threatened and you sulked. He was the real douche bag. The douchiest bag out there.

You don't get the respect that should come with your job title. Many people do respect you but some tale advantage of the weak image you've made of yourself. But Mr. Ackles always has your back... whenever he can.

You're not some sort of slave. You're a respected individual, atleast by the one person who matter to you. Mr. Ackles is all a boss should be, he cares for you and you're sure about that.

You like him... you like working with him. It's the reason why you haven't left-

"Mr. Ackles was asking about you Ms. [y/n]," A lady by the name of Becky told you and you smiled at her. You walked over to his office door and knocked on it lightly. Whether it was the way you knocked or the speed and rhythm of it, or something else entirely, Mr. Ackles always knew that you were standing on the other side of the door.

"Come on in [y/n]!" He shouted from the other side and you smiled slightly. Before walking in, you clenched your jaw so that your refrain from smiling in front of him.

"Mr. Ackles, I've got some-"

You paused, watching as his mouth was wide open with lettuce sticking from a fork about to make home in his mouth.

"Oh, I'm sorry. I didn't know you were... eating," You place his coffee on his desk neat his pencil holder and place the stack of papers next to it. You hurried to the door as you said, "I'll come back later."

"No [y/n], you don't need to come back later!" He stopped you, standing from his seat. He ran a hand through his hair and went over to his bookshelf. He opened up a drawer and took out a plastic see-through container.

"I got you something to eat while we discuss something about the company's latest project," He explained and you looked at him with your head tilted. You didn't know how to react.

Are boss's supposed to get food for their secretaries? Is this normal? I probably seem like some weak and needy person, taking food from my boss...

You feel hesitant but he puts the box forward, sticking his arm out. You can't reject his offer... can you?

You smile slightly then take the box from him. He gestures for you to sit down on the seat infront of the desk and you nod your head.

I hope this doesn't end up becoming awkward... You thought

*****

3 days later... The weekend

You walked into the local bar, it wasn't too shabby and it wasn't too extraordinary. It was perfect for a casual night of having some drinks.

You sat on one of the stools close to one end and asked the bartender for some beer. He came back moments later with a bottle and thanked him.

You started to drink, only to-

Shit, You thought as you noticed the guy sitting on the other end.

Your eyes widened, trying to analyse and make sure if the person you saw what actually that person.

SHIT SHIT SHIT, You thought.

It was your boss, Mr. Ackles.

You started to get up from your seat but he saw you and waved. You waved at him and smiled nervously.

Great, you can't go anywhere now.

Mr. Ackles walked towards you and smiled. "Hey [y/n], what are you doing here?" He asked and looked to the seat next to you, "Mind if I?" You shook your head and smiled.

He sat next to you and you answered, "Just having some weekend drinks. What about you? I'd imagine you'd be home with your wife but I guess... not."

"What? No way, I don't have a wife! I'm not married," He responded and you stared at him with surprise. "Really? You must have a girlfriend," You said but he smirked and shook his head.

"Wow... And I'm your secretary. I don't even know about your personal life," You felt odd inside, as if you're doing your properly.

"That's alright, you're my secretary at work. We have nothing in terms of a personal level... yet," He said and took a sip from his drink, "I don't talk about my personal life with my colleagues."

"Well, same here then. I've got no one," You said and sighed. He smiled, "Cheers to being loners then." He put his drink near your beer bottle and you clinked his glass. You smiled happily.

"You're a very interesting person [y/n], I'm surprised you aren't in a relationship," Mr. Ackles said and you shrugged. "I thought you'd have someone Mr. Ackles but-"

He put his hands out and shook his head. "It's Jensen. We're not at work, we're just two people talking and who want to know each other better right?" He explained and you nodded.

"Okay Jensen..." You felt really weird when calling him by his first name, "I thought you, being an owner of one of the largest companies in the country and perhaps the world, would return home to a woman... or man, I don't judge, every night."

He chuckled. You'd never heard him do that, which was surprising for you. "Well... That person will come along when the time comes," He said, "It'll just click."

You looked at him with fascination. Sure, he was kind of informal with you at work but right now, he was so casual and you wouldn't imagine him being your boss of all people.

"I think we're going to spend more time here talking to each other," Jensen said, "Can I buy you a drink?"

You smiled, "Sure Jensen, I'd love that."