Summary: She loved him and she watched him go. In a fit of sorrow, she threw herself in the arms of a stranger, not expecting to land herself in the current situation.
Word Count: 2268
Warnings: None
A/N: Thank you for your love thus far and thank you for taking your time to read this series!
PART 1
The breakfast was awkward for the female as she watched her sister and Sam intimately conversing with each other. What distracted her even more was the fact that Dean, her new brother, was brushing his foot against hers constantly. It caused her cheeks to bleed red, to which she tried to hide with her palm.
“Y/N?”
“Hm?” Her eyes trailed over to Sam who seemed concerned by her growing red cheeks.
“Your face is flushed. Are you feeling sick?”
The red on her cheeks grew darker, “No, no! I’m fine. Perfect. Don’t you think it’s hot in here?”
“Must be your imagination. It’s pretty cold in here,” Dean chuckled darkly.
“I hope you aren’t sick,” her sister worried, a frown apparent on her face. “Her colds last forever.”
“Yes, I’m fully aware of that.” Sam smiled at Y/N, “Since we’re all finished eating, I’ll go pay so you can go sleep off that cold.”
She nodded, glancing away from the man as her blush stained her whole face. Inwardly, she was celebrating the fact he remembered a minisicule detail about her that she told him during their rendezvous at the cafe. It meant that he hadn’t forgotten about their time spent together years ago.
The giddy smile that broke on her face didn’t go unnoticed by the older Winchester as he fiercely glared at her with a disgusted look. She didn’t pay attention to him, keeping her gaze on her empty plate, waiting for her blush to die down.
“You guys go on ahead. We’ll meet up by the entrance,” her sister stated as she shooed them off. The two nodded and traveled outside.
Standing ten feet apart from each other, there was an awkward tension between them, but for different reasons unbeknownst to the both of them. Y/N, hoewever, wanted to get to the bottom of things.
“What the hell are you plotting?”
Dean’s eyebrow quirked up, “Excuse me?”
“What are you trying to do? You think it’s funny to embarrass me in front of your brother?”
“Don’t flatter yourself. You’re ruining yourself on your own accord.”
“I know my feelings are none of your concern. Frankly, I could care less about you too, but for the sake of our siblings, we should try to make this work.”
“You don’t care for your sister. This is about you pleasing my brother.”
“...What?” She was beyond stunned by his words, rendering her speechless.
“It’s written all over your face. The only thing you care about is being a Winchester and getting down my brother’s pants, which is why you feel bitter by the fact your sister married my brother.”
“Well shit, you have me all figured out,” she snapped, sarcasm heavy in her words.
“I want to be a Winchester so bad, I’m pissing off the younger one!”
“You’re probably finding some excuse to whine to my brother to steal him away from your sister.”
The hand that connected with his cheek was as loud as a clap and everything around them fell silent. “You’re disgusting.”
His cold gaze locked with her hurt ones, causing his lips to press together in a tight line. He didn’t expect that reaction from her.
“Y/N, Sam wanted to ask you for a favor before you -Oh! What happened here?”
Her eyes averted away from her sister, “I’m leaving. Just drop me a text of what you need and I’ll do it.” Her voice wavered, and she quickly stalked away to the parking lot, leaving her sister in a confused state.
“Dean, your cheek is red. Did Y/N do something?”
Dean directed his attention to his sister-in-law and shrugged, “Don’t worry about it.”
Right on cue, Sam returned from paying the bill, his eyes instantly went straight to the hand-print mark on his brother’s cheek, “I suppose you finally got to know Y/N then.”
Dean exhaled loudly. He didn’t think he would meet such a troublesome girl, let alone, a messed up one like her. But the power behind her slap really peaked his interest.
“I don’t think I read the text right, but you want me to what?” Y/N asked her sister on the phone. She paced around the living room of her medium-sized apartment, dressed in an oversized shirt and elephant printed socks as part of her sleepwear.
“Please show Dean around the city, and where his office will be.”
Y/N grabbed and threw her purse several times onto the counter in anger, then stalking to her refrigerator to look at her calendar. She clicked her tongue at her availability, granted it was her day off from work. “Can’t Sam--”
“We’re family now, so we need the both of you to get along.”
We get along quite well in bed just so you know, she mentally said. Outside the bedroom? Not so much.
“Shouldn’t you take him? He is more of your brother-in-law than he is mine.”
“Y/N, it’s important to me that you get along with Dean. I’m happy you are friends with my husband, it really is great, but I need you to at least be on better terms with Dean.”
A sigh tore through her throat as she rubbed her temple with her free hand. There was still an ongoing debate in her head, but the gnawing feeling of hurt triumphed over her mind.
‘Her husband,’
Thos two words sliced her deeper than what the idiot older brother said.
“I understand Dean can be difficult. He’s just awfully protective of his younger brother, so having another person in their circle makes him more hostile,” her sister explained. “I’m not going to ask what happened between the both of you earlier today--”
“Okay, okay. Fine,” she groaned. “I’ll show him around.”
There was a sigh of relief from the other end. “Thank you, Y/N. I knew I can count on you!”
Glancing at her watch, she huffed in annoyance as the seconds ticked away. It was already past 10 in the morning and far too early for her to be up on her day off.
Unfortunately for her, Dean was still a no-show which further irritated the female. Being an event planner, it was all about promptness, molding this pet-peeve of tardiness in her.
“Jerk,” she muttered under her breath as the hand landed on the 6. “10.30, and he--”
“Is here,” a familiar voice interrupted. Startled, she whipped her head to the side to see Dean smirking at her.
Wearing a black tshirt that clung onto his body nicely, a red plaid flannel over it, and dark blue jeans. This man was too handsome. He had the kind of face that stops you in your tracks. I guess he must get used to that, the sudden pause in a person’s natural expression when they looked his way.
“I’m doing you a favor, and you’re late.”
The plastic bag he held onto was ushered into her hands, “I was told you like this.”
She sent him a suspicious glance, but the way he crossed his arms meant that he was unhappy about something. She pulled the bag open and peeked inside.
“I do like this type of snacks, but why are you giving me this”
He didn’t want to say anything, but her persistent silence refused to let it go.
“I was harsh on you last Monday.”
He wasn’t going to apologize, that much she was sure of. If she demanded an apology, she felt he would create another war between them both, which would undo the thoughtfulness of the present him. Plus, all she wanted to do was please her sister and Sam.
“Thanks for this,” she mumbled.
He shrugged, “Let’s get this over with.”
Shaking her head softly, Y/N guided Dean away from the plaza and into the subway. When they arrived at their destination, she pointed at one of the tallest buildings in the city, citing that this was his building. She refused to enter with him while he inspect his office and speak to the man he was taking over for.
It took less than an hour for him to return, all the while she waited patiently at a nearby fast food restaurant.
“Typical,” Dean muttered as he joined her in an isolated booth. He faced her with a scowl, arms crossed as he eased into the comfort of his seat.
“You didn’t enjoy your time with your boss?” the female hummed as she took a sip of her beverage. The remnants of her lunch were scattered around the table, evidence that she had eaten without him.
“You enjoyed your lonesome lunch?” he roterted.
Her eyebrows twitched, though she noticed his discomfort. “You must he angry that I ate a delicious burger while you had to endure with those business people.”
“For starters, that man is not my boss,” he corrected her, his hands reaching over to grab a fry, throwing it in his mouth.
“Secondly, I think you make a bad tour guide. You failed to feed me. No wonder your event company is so low-leveled. It has incompetent employees bringing it down.”
“Oh sure, go ahead, make fun of my job too. There’s a lot about me that can’t match up to the Winchester’s name, that I agree, but at least I have the decency to shut my mouth when I’ve crossed the line,” she replied acidly as she referred to what happened last week.
He remained silent, analyzing her angered expression.
“So you’re a person who owns three cats and loves her job.”
“...Is that an insult?” She cracked a smile, “That has to be the dumbest thing I’ve heard you say.”
“You’re laughing now?” He scoffed.
She attempted to stifle her laughter, but his words replayed in her mind.
“Cats? Freaking Cats? Here you were, insulting my family and me, and then pull that lame insult out of your ass? It’s hilarious!”
Her laughing was contagious, even to Dean. His narrowed eyes softened up as a small smile formed on his lips. “You’re weird. I bet you don’t have any friends.”
“And you’re very childish, also an asshole. You probably only have enemies,” she stated between giggles. “But at least I’m the best at my job.”
“Yeah right,” he chuckled as he glanced away. There was amoment of silence as Dean pondered over her statement.
“Hey, wanna test it out?”
“Test what?”
“How good you are at your job.”
Her eyebrows rose with interest. “Go on, I’m listenng.”
“The Winchester firm is celebrating the retirement of the man I’m taking over. I’ll recommend you to be the event planner. If you don’t fail, they’ll probably hire you as a permanent planner.”
“That sounds like the perfect challenge.”
“If you fail, which I’m 99% sure about, you’ll be left in the streets for sure and the Winchester family will ruin you.”
“...My brother is an asshole.”
“I’m not your brother.”
Their eyes met, and she could feel his heated state burning through her. The sexual tension proved they couldn’t consider each other as siblings even if their own siblings married each other. Not even that marriage could hold back the connection these two owned.
“It’s a deal then.”
His smirk grew, plagued with his permanent cockiness. However, she was ready to prove him wrong.
The next few days, Y/N anxiously waited any phone call from the Winchester company regarding her employment. She was completely wrapped up with the challenge that Dean proposed, she hadn’t noticed how large scale the party proved to be; she hadn’t realized that Dean’s position was so far up in the company ladder that they could in fact ruin her.
She only found out an hour upon her return from the excursion, googling the name of the retiring man. Apparently, he was third in command, and for Dean’s young age of 25, it was a huge accomplishment for him to be presiding over that job.
He wasn’t lying when he warned her how the Winchester company would ruin her if she happened to fail.
“Y/N, can you come to my office?” her bass called, gaining the attention of all the employees on the floor. The middle-aged woman signaled her over with two fingers with a stern gaze.
“We need to talk.”
That’s never a good sign.
Her heart sped up as she fumbled out of her work space, her feet hastily traveling towards the grand office her boss occupied.
“Y-yes?” She quietly closed the door behind her and sat in the chair across her boss’ table.
“I don’t know what, why or how, but we are going to be the event planners for an event hosted by the Winchesters.” Her eyebrows rose, intuitively guessing it was she that arranged this.
The marriage between her sister and Sam was no secret in the business world as it caught quite the attention; a no-name engineer marrying the soon to be CEO of Winchester Enterprise? Yeah, that was an eye-catcher.
“That’s great!”
“You definitely had something to do with this since they asked for you to be the head planner.”
“W-what?” Now that came as a shock to her.
She had expected Dean to request a more experienced person to be in charge, but it was apparent that he was taking this challenge far too seriously.
“I know you are more than capable, but you have never done an event this large scaled. This is an important company we want to impress, so I expect no mistakes. Do I make myself clear, Y/N?”
“I won’t let you down!” Y/N replied determinedly.
Challenge accepted, Dean Winchester.
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