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sorenmarie87 · 3 years

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Be my date to this wedding?

Summary: After a long day of work, you go out to eat with a few of your employees.

Square Filled: CEO AU (Mixed Bingo)

Pairing(s)/Character(s): Dean/Reader, Sam/Ruby

Word Count: 1,223

Warning(s)/Rating: Teen+ | Reader wears glasses, Dean has a major crush on his boss. Ruby is an author (it’s how her and the reader bond), Talking about having sex on your bosses desk.

A/N: This was created for @spnmixedbingo and my aesthetic pictures were found and Pinterest. Beta’d by the lovely @iflostreturntosteverogers

—

“Boss?” Your entire body jolted awake as you raised your head from your desk. You glanced around your office in confusion as you readjusted your glasses, and realized that it was later than what you expected. “I know you’re still in there, c’mon open up!”

“It’s unlocked.” You muttered as you stepped out of your office chair and stretched out your sore muscles. A satisfying crack echoed throughout your office as your door opened and Dean stepped through, with Sam trailing behind him.

“Thought you’d be home by now Ms. President.”

“Dean it is after hours, please call me Y/N.” You chuckled and knew that he’d call you anything but your given name.

“You know better than that,” Sam chuckled and made a beeline for the empty corner by the window. You watched as he stretched out on the sectional and pulled his laptop out. “He gets all flustered when you pay any form of attention to him.”

You smiled and watched as pink dusted his face. “Oh yeah?”

“He really likes it when you yell at him.” Dean glared at him but didn’t say a word to deny it.

“Okay, I know this isn’t a social visit boys. What can I do for you?”

“We talked to HR earlier but we’re going to be taking a few weeks off. Sammy here, he’s gonna be tying the knot soon.”

You frowned at the thought of not seeing them for a few weeks. It confused you though. It made sense why Sam was taking time off, but not Dean. What was he planning on doing? “I was hoping that you’d come to the wedding Y/N.”

“You actually want your boss to come to your wedding?”

“You’re more than a boss to me Y/N, I don’t know how to explain it honestly.” The look on Sam’s face said it all. You were family to him and that made your heart flutter.

“This is very last minute Samuel.”

“I know, I’m sorry.”

“Promise me you’ll text me all the details so I can arrange something, I don’t want to show up empty handed.”

“You don’t have to get us anything - “ You glanced over your glasses at him, and Sam held up his hands in surrender. He knew how you were about gifts.

“Now that that’s settled, you guys wanna get a late dinner?” Sam asked and right on cue, your stomach growled loudly. “I’ll take that as a yes.”

"You'd be starving too if you had to work through your lunch." You grumble quietly.

"You could've texted one of us, and we would've gotten you something…"

"Could have but I didn't." You sighed as your stomach growled again.

"Sammy, call in an order from that pizza place we like." Dean smiled and the two of you watched as he pulled out his phone. You started to reach for your purse, to give them your card but Dean stopped you in time. "This is on us."

"If you're not letting me pay, can I make a suggestion? Can we go there and eat? I'm tired of being in this office." Dean grinned and the two of them nodded in agreement.

"That's perfect actually. You'll get to meet Ruby, that's Sam's fiancé, she'll be joining us."

"That's fantastic."

—

Sam opted to wait outside on Ruby, and you repeatedly asked if he was okay by himself. You heard Dean chuckle as he grabbed a hold of your wrist and tugged you inside the restaurant. As you slid into the booth it hit you. Sam was still kind of shy about PDA even though his older brother thrived on it.

"You know how I can tell you're thinking too hard? I've been standing here for a couple minutes, asking if you wanted your drink and I got bupkis."

"Sorry." Your face heated and you tried your best to avoid looking at Dean.

"Now boss, what were you thinking so hard about?" Dean asked as he placed the plastic cup in front of you and handed you a straw.

"What if Ruby doesn't like me?"

"She'll like you, I promise."

"Not many people do…."

"Give me names." You take a small sip from your cup.

"Tracy from Accounting, Ryuji from 2F and my assistant Emma." You put a finger down for each one you named off.

"Emma likes everyone!" Dean chuckled as you quietly muttered to yourself.

"Maybe a little too much. I mean, I get the appeal of boning in your bosses office. God knows I’ve read enough stories about it.” You know you’re blushing heavily at this point and by the look on Dean’s face, you caught his attention. “It's a power play for sure, but shouldn't you wait until your boss is gone to try?"

"If you wanted to try something like that, sure. Not that I've ever considered it." That's a bold face lie and you know it Dean. He had a dream about that exact scenario a couple weeks ago with you in it. He couldn't look you in the eye for a full day after it.

“Well this conversation seems like one I wanna be a part of.” You could hear the smile in her voice without seeing her face.

Dean peered over his shoulder as his brother and fiancé approached the booth. "So Ruby, what's your take on boning in your bosses office?"

"I'll try anything once."

"You would." Dean muttered into his drink as you looked between the two.

"I just think it seems uncomfy." Ruby nodded and smiled at you.

"People love reading about it though."

"Ruby, if you can't tell, is an author. She's published a few books under the name R. Winchester." There was no way, you dug through your bag and pulled out the latest book you bought. Ruby's face lit up when she saw the title.

"With that book alone, this is telling me more than I could ever need to know about you. If it's okay, would you wanna be friends?" Ruby smiled and there was no way you could say no.

"I'd love that."

"To celebrate our newly budding friendship, what would you say about being my maid of honor?" She watched you carefully as you took a sip from the cup in front of you.

"That's a lot for someone you just met Rubes."

"If I had any friends, I would've asked them by now."

"I'll do it."

Your ears were assaulted by different responses ranging from really? to a high pitch squeal from Ruby as she took the seat next to you and wrapped her arms around your shoulders.

"Thank you so much!"

"If I would've known the two of you were gonna hit it off, I would've introduced you sooner." Sam grinned. "Will you be able to find a dress that fast?"

"I don't -"

"I'll help you." Dean interjected and you looked at him in confusion.

"Oh really?" He knew Ruby was teasing him but Dean shrugged it off.

"Yes really, I've been present for a majority of the wedding planning so I can help her pick out something nice." Your face flushed again.

"Thank you Dean." Your face was still warm but you had to ask. "Wanna help me out with one more thing?"

"Sure, why not?"

"Be my date to this wedding?"

"I thought you'd never ask."

Forever Tags - @lovetusk @coffee-obsessed-writer@artemisthebadger @littlehotmess26 @mirajanefairytailmage @kazosa @wings-of-a-raven @docharleythegeekqueen @clockworkmorningglory @lefthologramdeer @ellen-reincarnated1967 @holyfuckloueh @buckyscrystalqueen @ilovetaquitosmmmm @n3rdybird @super-fan-of-all-things @disneymarina @sandlee44 @babykalika2001 @mrswhozeewhatsis @mariekoukie6661

Dean Winchester - @idreamofplaid @thing-you-do-with-that-thing @akshi8278 @deans-baby-momma @onethirstyunicorn @jensengirl83 @anaelsbrunette @lyarr24

#spnmixedbingo #ceo au #Dean/Reader #Dean Winchester & Reader #Sam Winchester/Ruby

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