#boss!dean

Dean Winchester is the CEO of Winchester Co. for the past four years. He’s the oldest son of John Winchester, the founder and owner of Winchester Co., a real estate business. His office corner suite on the top of the floor in the building with floor-to-ceiling windows offering a panoramic view of the city skyline. The décor is modern yet understated, featuring a large mahogany desk, plush leather chairs, and abstract art on the walls. Behind the desk is a sleek bookshelf lined with awards, framed contracts. A smart wall panel controls lighting, climate, and the room’s privacy settings.

On the top floor other than the CEO’s office is his personal assistant’s work space. It’s a sleek, efficient area with a streamlined desk equipped with multiple monitors for scheduling, managing calls, and overseeing the flow of appointments. The space is minimalist, with soft lighting and ergonomic seating, offering both a professional and welcoming atmosphere for visitors waiting to meet the CEO

“Good morning, Mr. Winchester.” Y/n said entering his office. Dean looked up from his computer and glanced at the woman standing in the doorway with a styrofoam cup in her hands. “Got you your coffee.” She said holding it up. The man nodded and she entered the room completely, moving to hand him his daily dose of caffeine, which has been the routine for the past four years.

Y/n reached his side and he took the cup from her hands gracefully and placed it onto the table before pulling her down onto his lap. Y/n gasped at the sudden pull and he grinned up at her.

“Good morning baby.” Dean leaned up to place a soft kiss to her lips. “You’re late.” He commented resting his hands on her hips.

“Sorry boss, my boyfriend is a bit clingy in the morning.” She replied with a mocking smile. “Acts like a baby doesn’t let me leave when I spend the night.” She added with a pout. Dean barked out a loud laugh and it was moments like these that he was thankful for having the whole floor to himself.

“Acts like a baby, you say?” Dean feigned curiosity. “Well tell him you’re my mine and I need you here on time.” Dean mock reprimanded her. Y/n rolled her eyes at his teasing.

Dean Winchester is a private man. He doesn’t like expressing his emotions or talk about his personal life. He’s a workaholic and is married to his work. He had been working at this company ever since he was in college. While perusing his degree in business he did part take in business matters, worked as an assistant for his father. He’d worked hard for this title and four years ago he was appointed at the CEO of the company when his father stepped down.

When Dean was appointed CEO, he clearly needed an assistant too. He confided in his best friend, Castiel. Although Cas also had a degree in business administration he was not interested in taking over his father’s business and was rather interested in charity work and philanthropy. Castiel had suggested Dean to appoint Y/n as his PA, since he knew her from college and she had remarkable skills as well.

Although Dean did appoint her on Cas’ insistence he was a bit skeptical of her skills she needed a ‘recommendation’ to get a job. For the whole year, Dean made her work relentlessly, putting her skills to the test and demanding a high level of performance to prove her worth. And she did. With her hard work and extremely remarkable skills she impressed Dean, more than professionally.

In a typical cliche manner, the grumpy boss fell for his assistant. Though persuading her was a challenge for Dean. She was hell bent on keeping things professional and not wanting to cross the boundaries at her workplace. She was a hard nut to crack but eventually Dean worked his charm on her, showing her beyond his grumpy boss personality and wooing her with extreme gestures.

Now the two had been dating for almost three years and the only person who knew about them is none other than Castiel, the one who introduced them. Even Sam was not in on the secret.

“Can I go back to work, now?” Y/n asked getting up from his lap but he kept his hold firm on her hips, not letting her leave.

“No.” Y/n pouted in response, she hated when he did this, holding her hostage while at work . She really wanted to keep her personal and professional life apart, not wanting anyone to find out or even think for a second she’s sleeping with her boss.

“Dean.” She scolded when he kissed her pouty lips.

“Relax sweetheart, nobody’s coming up here anytime soon.” He shrugged and she sighed loudly, indicating her defeated even if she was reluctant. “Besides, I’ve got news for you.” Y/n raised her brow in curiosity urging him to continue. “We,” he traced her arm with his finger. “are going on a vacation.” Dean beamed at her.

“A vacation? We?” Y/n furrowed her brows. “Who’s we?” She questioned, clearly not understanding the situation. Is this a office vacation or the top officers vacation or just the two of them.

“You and me. A week in Bahamas.” Dean replied casually.

“A week? You want us to take a leave at the same time? It’d rise suspicion.” She whispered alarmingly.

“Baby, if I’m on leave then you’re on leave automatically. Besides, I’ve asked Cas to manage for a few days for me.” Dean replied. “We both have been working our ass off for the past four years, I think we deserve a vacation.” Dean grinned at her and for the first today, she agreed without interjecting. She’s just as much of a workaholic as Dean. She had taken a day off here and there but never a complete vacation. “Besides I’m dying to spend some time quality time with my girl without her grilling me about work.” Dean sassed and she smacked his arm lightly making him laugh.

“I’m not gonna slack off at work just because I’m dating you.” She said matter of factly. “And I do think we could use a vacation.” She finally agreed making his smile broaden. “God, if anyone could you see right now, Mr. Grumpy Winchester.” She giggled when he rolled his eyes. He loved it when she teased him about being a grumpy ass to everyone else except her but he would never accept it in a million years.

The door swung open and sauntered in Castiel in the flesh. Y/n quickly jumped off of Dean’s lap but relaxed when she saw it was Cas.

“Ever heard of knocking, Cas?” She taunted her friend, crossing her arms across her chest.

“Ah lovebirds. Ever the cautious.” Cas sassed back and Dean snorted earning himself a glare from her. “Don’t stop on my account, just wanted to deliver these, personally.” He said holding up two flight tickets to Bahamas.

“Thanks man.” Dean said getting up from his chair and getting the tickets from his friend. Castiel shot Y/n a teasing grin and she rolled her eyes at him, clearly unbothered by his teasing. He thrives in teasing her because she was the goody two shoes in college and the two had become friends after being paired up for an assignment, so seeing a different version of her around Dean, leaves him anything but amused.

“You are a bad influence on the both of us.” Y/n said feigning an angry glare at Cas.

“Oh dear Y/n, I know.” Cas winked and Dean laughed at his best friends shamelessness. The trio’s camaraderie was a reminder of how personal and professional lives often intersect in unexpected ways.

Tags:

@spnfamily-j2 @galway-girlatwork @deangirl96 @queensilber

@s0urw00lf @monkey-d-hoshizora98 @deans-baby-momma @fullbelieverheart

@riah1606 @xx-spooky-little-vampire-xx @hobby27

@starkleila @suckitands33 @m3ntally-unstable @kanekilovelove-blog @candy-coated-misery0731

@blackcherrywhiskey @ladysparkles78 @goest-and-fuckest-thyself-blog @graywrites5567

I took a deep breath before heading towards the front entrance of the warehouse. It took a couple of pulls for me to realize that the doors were locked.

"Hello, can I help you?" A voice coming from the small box mounted on the side of the door startled me as I took a step back.

"Oh..hello! I'm Y/N, here for my interview with Mr. Winchester." I said, though my tone was a bit awkward, and the butterflies in my stomach were growing intense by the minute.

A quick buzz and clicking sound followed, and I opened the door to see a man sitting at his desk in an office behind a large sliding window. We waved and smiled to each other, and he gestured me to have a seat inside of the empty lobby.

"I'll tell Mr. Winchester you're here." He says as I acknowledge with a nod. I watched him as he rose out his chair and walked out of view. Through the gap of the window, I could hear his voice along with another, much deeper and masculine voice.

"What the hell? I didn't know I had an interview today." Could be heard loud and clear, yet the unprofessionalism didn't surprise me at all.

Suddenly, the door to my left flew open and a man wearing a plaid shirt and boot cut jeans stood there for a moment. He was much better...younger looking than I could've ever expected.

"Afternoon, Ms. Y/N." I stood up immediately and made my way over to shake his extended hand.

"My name is Dean, tightasses like Tim over there prefer to call me Mr. Winchester." He pointed to the receptionist, who shook his head while staring at his computer, "Either is fine."

"Nice to meet you Mr. Dean. No, wait I mean-"

"No, Mr. Dean is great I should go by that from now on." We both let out a chuckle as we walked towards a door with his name horrifically engraved on it.

"Did that myself." He boasts as we both step into his overly decorative office.

"Okay Ms. Y/N, I'll be honest with you. I had no idea you were scheduled for an interview today and I apologize for that." He says as he plops down into what appears to be a gaming chair and starts clicking and typing away at his computer.

"It's alright." I said dishonestly. I was taken aback by the amount of comic book paraphernalia in the room, like sitting inside the room of a teenage boy.

"Are those the Thundercats?" I pointed out a row of figurines in unique positions, all lined up on his desk.

"Hell yeah, I love those guys." He cheered, "You a fan of the show too?"

"I've never watched, but I know what they look like."

"You should totally watch it." He clears his throat and quickly apologizes for the casual conversation.

"Ms. Y/N Y/L/N, welcome to Winchester Bros Warehousing. My brother Sam and I run the place." I listen quietly as he explains what the position I applied for entails.

"Alright, so I'm gonna ask you a couple of questions, just answer them to the best of your ability okay?"

"Ok."

"Tell me about a time when or if you've had a problem with a co-worker and how you went about resolving it." He asked, as he grabbed a pen and paper out of his desk drawer.

My mind instantly took me back to my job three months ago, where I had a shouting match with a co-worker in the middle of the department store for everyone to see.

"Well...when I was working at Food Mart, I had a little disagreement with a fellow cashier named Stacey. I was minding my business at the register and she just came over and asked me if I had a problem with her. I told her no, but she wouldn't leave me alone because of something she claimed she heard from someone else."

"Petty bitch...sorry, continue." He blurted out.

"I didn't even say anything about her either! It got so bad that both of our lines began to pile up, people were pulling their phones out and complaining about us, and she still wouldn't leave my register. A manager had to come over and ask what was happening, and that's when she tried to threaten me."

"Luckily the manager decided to send her home for the threat. I kept my cool the entire time and went back to working like it never even happened."

"Classy move, so much better than a lot of people, including me." That got a giggle out of me.

Fifteen minutes later, we concluded the interview process, and I could tell that most of the questions were improvised. I'm pretty sure I've never had an employer ask me how I felt about the 28 days later franchise before. The biggest thing was the pay rate, and they were offering exactly what I was looking for. As I said goodbye and headed for the exit, I felt like I had made a good impression based on his reaffirming words that I would receive a callback very soon. I shook his hand one last time before walking out the same way I came in. Once I made it back into my car, I sat and took a breath of relief. There were a few things on my mind all at once, most of all, the hope of finally being able to get back on my feet again.

As I sat there in my '09 Impala, I turned to my left and saw an even older model Impala parked next to me. All black and souped up as if it were made brand new, a real beauty. My admiration came to a halt as two men approached the car. It was Dean, and another tall, handsome man on the passenger side. They got in the car and slammed the doors shut, Dean turned to his left and saw me looking at them.

"Lunch time!" He shouted out the window over the roaring coming from his engine.

While both of them were looking over at me, he put his finger up, rotating it in circles. I promptly rolled down my window.

"You got the job by the way. Just talked it over with my brother Sammy over here," He points over his shoulder to the man in the passenger seat, who smiled and waved at me, "We'd love to have you! Come back tomorrow, same time."

I give him a nod and wave back at Sam.

"Thank you!" I shouted.

”Well hello ladies,” said Dean at the coffee machine, wearing a big flirty smile. “Anything left?”

“Just threw on a new pot,” said Kelly, smiling at you as she excused herself.

“She still scared of me?” asked Dean as she left.

“You’re sort of the junior director of sales. Just a tad intimidating to some of the peons,” you said, Dean chuckling as he grabbed a cup. “What are you doing down here drinking our crappy coffee anyways?”

“Just checking in on my supposed peons,” he teased, earning an eye roll from you. “No, actually I need another copy of that presentation.”

“I emailed it to you. Three times already,” you said, Dean shrugging. “You don’t need an excuse to come talk to me you know.”

“Okay, maybe I don’t need another copy but where’s the fun in not teasing you?” he asked with a smile.

“Still the boy from the mailroom,” you teased, shaking your head at him.

“If I recall it used to be you that would come visit me down where the peons worked,” said Dean, sipping on his coffee. “You were such a cute little college intern.”

“You were way too smart for there. You knew how to do my job better than me,” you said. “Swept you up on the fast track after that.”

“I had some help,” he said, scooting out of the way when someone else came in the break room. “I’ll talk to you later.”

“Mr. Smith,” you said, knocking on the door to his office. “I’m here for our meeting to go over those charts.”

“Mrs. Smith,” he said as he stood up, closing his door after you, turning the lock. “You brought your laptop?”

“I at least have to pretend to be having a meeting, Dean,” you teased. “S’been a while since I got a meeting invite.”

“The new guy over in financials was staring at your ass earlier. You know, that’s my ass to be able to stare at,” he said. 

“I do have a real meeting in fifteen,” you said with a giggle. 

“I’ll be quick then,” said Dean, pulling you over to his desk chair and taking a seat. He undid his pants and you pulled down your skirt, climbing on top of him the second he had a condom on. “You’re like, the best wife ever, you know that?”

“Oh, I know,” you said, giving him a chaste kiss as you rolled your hips, a tiny groan leaving his lips. “Sh or I’ll stuff that tie in your mouth again.”

“Like I said, best wife ever.”

“Well hello gorgeous,” you heard as you opened the front door that night, dropping your work bag and kicking off your heels.

“That smells delicious,” you said, walking down the hall into the apartment, Dean working over the stove with rolled up sleeves. You bent over and threw your hair up in a messy bun, skirting into the kitchen to ruffle Dean’s hair into something more natural looking on him.

“And you said that couples cooking class was going to be stupid,” said Dean.

“It was stupid. I burnt soup. Soup, Dean. How do you even do that?” you asked.

“You are a very special girl, that’s how,” he teased, kissing your temple. “How was your day?”

“Eh, same old same old. This really cute guy talked to me in the break room today though. Plus I got to have like a teensy bit of sex with him. Hopefully I’ll score again with him tonight,” you said with a wink, Dean raising an eyebrow.

“Oh? I bet he’s madly in love with you on top of being extra adorable,” said Dean, laughing when you smacked his arm. “You better be talking about me you realize.”

“Well the coffee breaks are the best part of my day, and the occasional last minute meeting,” you said, hugging him from behind.

“Mine too,” he said, wrapping an arm around your waist behind himself. “You guys have better coffee than us upstairs. Plus there’s this hot chick that works in Communications I get to see in these pencil skirts that just...mhm, super awesome part of my day.”

“I hate these things,” you said, reaching behind your back to pull away and pull down the zipper, stepping out of the skirt with a sigh. “Freedom at last.”

“When you’re done you mind watching the stove a minute?” he asked. You hummed, heading into the bedroom to change into one of his shirts and a pair of sweats, Dean back a few minutes later sporting a similar look. “Thanks, sweetheart.”

The duo arrived at Dean's penthouse, it was perched high above the city, a sleek sanctuary of glass and steel, with floor-to-ceiling windows that captured the skyline's every flicker and glow. Y/n watched with an amused look on her face as Dean paced back and forth in front of her, his expression was one of excitement and bewilderment.

“Can you stop pacing?” She giggled gesturing him to come to her. He stopped to look at her but he remained still at his place. He still wasn’t able to wrap his head around the situation. She removed her heels and walked over to him, snaking her arms over his shoulders while he held her by her waist. “Are you not happy?” She bit her lip, looking at him with inquisitive look.

“Are you mad?” He retorted. “I’m ecstatic.” He grinned pulling her closer. “I’m just baffled! What happened? How’d you change your mind? What’s dad gotta do with all this?” Y/n smiled at him and dragged him over to the couch. She made him sit down comfortably before sitting beside him.

“Your dad came to see me a few days ago.” She started.

It was a normal Sunday, Y/n was at home binging a show had to catch up on when the doorbell rang. At first she thought it was Castiel and she didn’t want to be bothered so she remained seated. But a few seconds later the bell rang again. With a loud sigh she pushed herself off the couch and opened the door. There stood none other than John Winchester.

“May I come in, Y/n?” She was quite shocked to hear that he knew her by her name, but then she realised it had more to do with her relationship with Dean than her being an employee at his company. She nodded her head, moving out of the way for him to enter.

Taking a seat on the couch John looked around the space, it wasn’t huge but it wasn’t small either. Decent and spacious enough for one person.

“Can I get you anything?” She asked awkwardly standing in front of him.

“Coffee would be great.” He replied. with small smile. After she prepared two mugs of coffee she gave one to him and sat on the couch opposite to him. “I assume you know why I’m here?” He asks taking a sip from his mug.

“Yeah I guess.” She murmured and he raised a brow wanting her to continue. “Your wife sent you here to ask me to back? I swear it’s not me, Dean’s not letting me resign.” She replied looking at the mug in her hands.

“It’s not why I’m here. I want to ask you something.” His eyes narrowed as he studied her, tracing every line and movement with calculated precision. “I talked to Castiel the other day and from what I’ve gathered you’ve left my son.” He spoke calmly.

“I would never ask him to choose me over his career and he was going to do exactly the same. So I made the decision for both of us.” She replied and John held back a scoff.

“Why don’t you just say that you don’t want to be with broke guy?” John egged her.

“With due respect Mr.Winchester, You’re sitting in my home and I will not let you disrespect me like that.” She glared at the man and he smirked at her. At the change of his expression she tilted her head in confusion.

“Care to elighten me then why did you let go so easily?” John asked leaning back on the couch.

“That company is Dean’s dream.” She started, “he’s worked day and night to be where he is. I have no doubt that if you kick him out he can work at any company and CEO. But this company is important to him, because it’s yours.” She concluded and John looked confused. He asked her to elaborate and she took a deep breath. “Dean looks up to you, he wanted to be CEO of this company so he could make it bigger and better. He’s never told it to anyone but he wants spread it countrywide, he wants to expand your business, to make you proud. And I can’t let myself be the reason, that he can’t achieve his dream.” She clenched unclenched her hands in her lap.

John let out a chuckle and she looked up at his face. He rubbed the back of his head before speaking,

“I’m sorry for accusing you, dear. I knew Dean’s choice was impeccable but I had to see for myself. You’re fierce and I can see you’re willing to give up your happiness for his’. But the thing is I don’t want you to. I want son to be happy.”

“What do you mean?” She looked at him suspiciously.

“Well, I’m assuming you’re invited to the wedding?” He didn’t let her reply before he spoke again, “Even if you’re not, I want you to attend. And object to this wedding as his rightful fiancée.” John said passing the small box he brought along. She gasped as she saw what was inside. The Winchester heirloom. “You deserve it.” John smiled at her.

“How’d you know—about the engagement?” She asked clearly taken aback. He chuckled in response.

“My son trusts me more than he lets on. He told me and I’m here to keep that trust intact.” He looked at her with almost pleading look on his face. “Don’t give up on him. He won’t lose his dream, I’ll make sure of it. But he won’t lose his love is something that you need to take care of.”

“So that was it.” Y/n smiled filling Dean in. “I’m sorry I didn’t try harder but that push was all I needed.” Dean shook his head at her words. He grabbed her hand and intertwined their fingers together. He placed a soft kiss on the back of her hand.

“You rescued me and that’s enough.” He grinned at her which made her laugh. “And I can’t believe dad went against mom for me. That man is the definition of whipped.” Dean thought out loud.

“But I guess that’s why he understands the situation so well. He knows what it’s like to love.” Dean nodded.

“True. I gotta thank the old man.” Dean stated. “But first, I need to make sweet love to my fiancée.” He added picking her up and carrying her into the bedroom.

Four months later Y/n and Dean decided to get married in an intimate setting with their close friends and family. Mary had refused to attend but Dean didn’t care. He was done with his mother’s antics and was fine with having his Dad, Sam, Jess and Cas by his side. And of-course the love of his life. Y/n had her family and close friends and it was perfect. The wedding took place in a cozy, candle-lit venue, adorned with soft florals and warm lights that cast a gentle glow over the small gathering of close family and friends. As the couple exchanged heartfelt vows, their closest loved ones watched, each tearful smile and quiet laugh creating an atmosphere of love and genuine warmth. The evening was filled with shared stories, laughter, and quiet moments, making it a deeply personal celebration of their journey together.

“After the wedding, the couple went off to their honeymoon to Paris, the city of love. It was an extremely enchanting experience, filled with moonlit walks, cozy dinners in hidden bistros, and breathtaking views from the Eiffel Tower. And lots of love making, Dean couldn’t keep his hands to himself. Every moment felt like a scene from a romance novel, as they wandered hand-in-hand through charming streets, explored art-filled museums, and shared quiet laughter in quaint cafes, making memories that would last a lifetime. Frankly Y/n didn’t want to come back home but they had to obviously.

Y/n was working at her desk, as Dean had suspended her notice period and completely disregarded her resignation. He didn’t want to spend a second away from her so he wanted her to continue being his assistant. He called her inside his office numerous time solely for the purpose of asking kisses. He called her in again and Y/n huffed walking inside. He beckoned her with his index finger, puckering his lips.

“You can’t be serious. I’m working.” She half glared at him, he smirked knowing she was trying to be intimidating but she enjoyed it as much as he did. A knock on the door resounded and Dean yelled a ‘come in’. It was Kevin, an intern.

“I got these files you asked me to Miss L/n, I was gonna leave them at your desk but I thought I’d check boss’ office.” He said sheepishly. Before Y/n could reply Dean spoke.

“It’s Mrs.Winchester.” He smirked proudly. Kevin quickly apologised and she dismissed him by telling him to leave them at her desk. He nodded and left. “Now Mrs.Winchester, a kiss please?” Dean pouted leaning back in his chair. She walked over to him shaking her head. She leaned to peck him but he pulled her onto his lap deepening the kiss.

“You’re lucky I love you, Mr.Winchester.” She muttered against his lips.

“Damn right I am.” He kissed her again. “Just so you know I love you more, Mrs.Winchester.”

Tags:

@spnfamily-j2 @galway-girlatwork @deangirl96 @queensilber

@s0urw00lf @monkey-d-hoshizora98 @deans-baby-momma @fullbelieverheart

@riah1606 @xx-spooky-little-vampire-xx @hobby27

@starkleila @suckitands33 @m3ntally-unstable @kanekilovelove-blog @candy-coated-misery0731

@blackcherrywhiskey @ladysparkles78 @goest-and-fuckest-thyself-blog @graywrites5567

@thelittlelightinthedarkess @enamoredwithbella @winchesterwild78 @myuhh8

@10ava01 @n-o-p-e-never @itsdesiree86

"I'm sorry Dean." Y/n pushed him away slightly, creating a distance between the two. "I can't do this." She said before leaving him alone in his office. Dean let out a breath that was half a growl, half a sob, and slammed his fist into the wall continuously. The pain flared through his hand, but it felt insignificant compared to the agony twisting inside him.

"Dammit, Y/n," he whispered, leaning his forehead against the cool surface. His knuckles ached, bruised from the relentless impact against the wall, and he stared at them, flexing his fingers slowly. The burn felt better than the storm in his chest, better than the helplessness swirling inside.

Outside the room, Y/n pressed her back against the wall, barely holding it together. Her breath hitched as she listened to the dull thud of Dean's fist hitting the wall, the muffled growl of his frustration carrying through the thin barrier between them. She squeezed her eyes shut, biting down on her lip to stop the sob that threatened to escape, but it was useless. It felt like her chest was caving in, like the weight of everything she'd been holding in finally shattered her.

Her hands trembled as she covered her mouth, trying to silence the gasping sobs that broke free, tears spilling down her cheeks. She slid down to the floor, knees pulling to her chest, head resting against the wall that separated them. She wanted to scream, to burst into the room and take all his pain away. But all she could do was cry.

Y/n took a deep breath, steeling herself against the waves of sorrow that threatened to drown her. She wiped her tears with the back of her hand and moved to her desk. She has to hold her ground, if Dean saw her break down he'd convince her to run away with him. And she'd be damned if she let him destroy his whole life just for her. With her head held high she turned back to her work although her soul was ripping apart inside.

The next few days were quite. Dean had been avoiding Y/n, although it hurt her to see him act so aloof but she knew it was necessary for them to maintain a distance. She saw the pain in his eyes every time he walked by or how avoided looking at her whenever they discussed work. She saw his hand wrapped in bandages and refrained from reprimanding him for hurting himself. She reminded herself that it wasn't her place anymore to say anything to him. Besides she was partly the reason he was hurt.

Y/n was engrossed in a mountain of reports at her desk when Rachel stepped out of the elevator with an air of confidence that made Y/n's skin crawl. She could practically feel the tension crackling in the air. Rachel was wearing that smug smile again, the one that said she was about to stir the pot.

"Y/n!" Rachel chimed, her tone almost too sweet. She placed a stack of glossy wedding magazines on Y/n's desk with a flourish. "I'm so excited to share my plans with you! I know you and Dean are close, and I could really use your insights." Y/n forced a smile, the familiar pang clawing at her chest.

"About what?"

"Oh, just some ideas for the wedding!" Rachel said, her eyes sparkling with mischief. "Dean and I have been talking a lot about our future, I'm glad he's finally accepting this relationship. I thought it would be nice to get your take on some things. Another girly input you know." She faked her enthusiasm clearing trying to hurt Y/n on purpose. Rachel leaned in, her expression feigning sincerity. "I just want to make sure it's perfect for him. He's had such a complicated life, and he deserves someone who can give him stability." There was a pause as she watched Y/n's reaction, clearly enjoying the effect her words had.

"Right," Y/n said, her jaw tightening. "You're definitely the one to provide that."

Rachel tilted her head, the smile never leaving her lips. "Oh, yes I am! I know you two had a... unique connection. But let's be honest, he needs someone like me who can really support him in his career. I wouldn't want him to get distracted."

Y/n felt her stomach twist at the thought, but she forced herself to smile. "Sounds... about right, Rachel." As Rachel continued to chat on about floral arrangements and guest lists, Y/n's mind raced. She felt trapped in a web of tension, with Rachel deliberately playing mind games and tugging at the threads of her heart. Her heart was pounding in her ears and she felt the need to throw up but she held it in.

"Just let me know if you think of any other ideas," Rachel said, her tone dripping with faux sincerity as she got up to leave. "I really value your input. After all, it's not every day you get to help plan a wedding, right?"

As Rachel walked away, Y/n felt the weight of her words settle heavily in the room. She turned back to her desk, the bright magazine covers staring back at her like a mockery. She buried her face in her hands for a moment, battling the swirling emotions, frustration and hurt colliding within her.

Dean walked out of his office to head to his meeting, his gaze landed onto Y/n clenching and unclenching her hands on the table top, her eyes fixed onto the magazines that littered on her desk. He could see hear breathing harshly and the tears pooling her waterline. He wanted to reach forward and kiss her tears away. He wanted to hold her and throw those stupid magazines out of the window. His jaw clenched as he held back. It should've been them, it should've been their wedding, their plans. He cleared his throat gaining her attention. She looked up at him with an emotionless expression on her face.

"Mr. Winchester." She cleared her throat, ignoring the lump that had formed. The tremble in her voice was obvious to them both.

"May I ask Miss. L/n, why is your desk littered with magazines instead of the reports you're supposed to be working on?" Dean asked, his tone was professional but gentle at the same time.

"I'm sorry, sir." She paused when Dean made a sound at her calling him 'sir'. He hated it with a passion and she knew it too. "Miss Rachel wanted me to help her plan the wedding." She replied looking at him. She wished she didn't know him well enough to read his face, but she did. He was crumbling on the inside, but at the same time anger surged through him, a dark haze clouded his vision.

"This is a real estate company Miss L/n, not a wedding planning service. Next time Rachel asks you do something like that, you inform me!" He said sternly. "Nevermind. I'll let her know myself." He spoke through gritted teeth. She nodded biting her lip, the lip that Dean wanted to pull between his own. He dismissed those thoughts and went on his way to his meeting.

"Fuck my life." Y/n whispered dropping onto her chair. "You made this decision for the both of you, you don't have anyone else to blame, Y/n." She mumbled to herself.

"I knew you were crazy but talking to yourself takes the cake, darling." She heard a voice say and she looked up to see Castiel standing in-front of her. She said his name in a soft whisper. He gave her a once over and his face morphed into a sympathetic expression.

"De-" she cleared her throat. "Mr.Winchester is in a meeting."

"I'm not here to see him." He said leaning over and placing both his palms on her desk. “I’m here to see you. C’mon, let’s go somewhere to talk.” He offered, he could see her debating so he added. “If it’s about not leaving work, you know I can deal with it.” She nodded her head gently and wrapped her work while he went to Dean’s office and wrote something on a sticky note and stuck it to Dean’s monitor. Castiel offered his arm to Y/n and she took it gladly, finding some sort of comfort in the presence of her friend.

Dean came back from his meeting and his brows furrowed at the absence of Y/n at her desk. Her bag was gone and the usual clutter on her desk was clean as if she was done for the day. He made his way inside his office and dropped on his desk chair, his gaze landed on the note stuck to the screen.

Took your girl out. Will try to convince her to change her mind! -Cas

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“It’s alright I’m his fiancée.” Y/n really wanted to scoff at the woman’s claim but then her gaze fell to the woman’s left hand. Her ring finger was adorned with a ring, a single sapphire gleamed at the center, encased by tiny diamonds. That was the kind of ring she’d seen in Mrs. Winchester’s finger. That was same kind of ring that she’s seen in Sam’s fiancée, Jess’ finger on multiple occasions. It was the Winchester family’s traditional heirloom, passed down through generations, a symbol of their legacy. She then looked at her own and realised that any one would believe this woman over her, if she ever claimed to be Dean’s fiancée. Y/n felt a lump forming in her throat but she took a deep breath and cleared her throat before speaking,

“I understand, however I can’t let you go in without permission, it’ll risk my job.” She forced a smile. “I’ll let him know you’re here.” She added gesturing to the door and to her relief the woman nodded in agreement.

Y/n knocked on the door while the woman sat on the waiting couch, Dean’s voice was heard from behind the door as he gave permission to enter. She went inside the room and Dean looked delighted to see her, but his smile faltered when he noticed her expression.

“Mr Winchester, there’s someone waiting for you outside but she doesn’t have an appointment. Shall I send her in?” She said monotonously and he furrowed his brow.

“Who is it?” Dean asked curiously.

“Your fiancée.” She said calmly and his eyes widened in surprise. He opened and closed his mouth multiple times unable to form a coherent reply. He understood the look on her face when she first entered the room. When he didn’t reply for a few minutes she added, “I’ll send her in.” With that, she left.

Dean was quick on his feet and followed her out the room and his gaze landed on the woman sitting on the couch. The woman stood up and swiftly made her way towards him.

“Dean!!” She exclaimed happily throwing her arms around his neck.

“Rachel? What are you doing here?” He asked and Y/n watched the scene unfold in front of her eyes. So he did know her. She wanted to look away from them but she couldn’t tear her eyes away from the couple and she desperately wished she did when she saw Rachel peck his lips. She grimaced before turning back to the computer screen holding back the tears that were threatening to spill.

"I thought we could get lunch together," she said, her voice soft with a hint of hope.

“I’m busy!” Dean replied tersely. He didn’t want to have lunch with her, he wanted her to leave as soon as possible so he could explain to Y/n. So he could gather her in his arms and tell her she’s the only one and this a misunderstanding.

“Some other time?” Rachel asked and Dean nodded not wanting to create a scene. He was expecting her to throw a fit and demand his attention but he was surprised that she agreed so easily. Rachel turned to leave but then she stopped at Y/n’s desk, “Oh, you’re engaged too?” She said to Y/n excitedly pointing to her ring her. “Congratulations.” She smiled.

“Oh this?” Y/n replied showing her hand to her, “I’m not engaged.” She said softly and Rachel’s face turned to one of confusion. “I deal with businessmen on a daily basis and rich men think they can make me their mistress because I’m just a secretary. So this keeps them away.” She explained, glancing at Dean who was seething beside Rachel. Hah take that Winchester.

“That’s so inappropriate and just unacceptable. Dean, You shouldn’t do business with such people.” Rachel told Dean and he nodded, clenching and unclenching his fists at his sides. “I’ll get going but—” She looked at name plate on her desk, “Y/n, don’t hesitate to tell Dean if anyone does it again.”

“I won’t. Thank you.” She smiled at the redhead. Y/n wished this woman was a cunning bitch, it would’ve been easy to hate her. But at this moment this moment the only person she hates is someone she swore to Love for the rest of her life. Rachel reciprocated the gesture and kissed Dean on the cheek before taking her leave.

“Inside. Now.” Dean growled at Y/n and turned on his heels to go back to his office. Y/n rolled her eyes before following him inside. She watched him pace back and forth, his jaw clenched. “What the fuck was that?” He asked in a dangerously low tone.

“She’s beautiful. Perfectly matches with you.” Y/n commented.

“What the hell is wrong with you? Why are you behaving like this?” Dean snapped.

“I’ve never been a mistress before. I don’t know how they act.” She replied crossing her arms and Dean was sure he’d have steam coming out of his ears. He was fuming. He grabbed her arm and pulled her to him.

“Call yourself that one more time and I’m not sure what I’ll do.” He challenged making her scoff.

“Drop the act Dean. I can’t believe you went this far to keep the ruse.” She said gesturing to the ring on her finger. She went to remove it from her finger but he pulled her hand away.

“Don’t you dare.” Dean growled. “She’s not my fiancée, you are.” He yelled not caring if anyone heard.

“Really? And who knows that except you and me?” She asked rhetorically and Dean didn’t have an answer because she was right. “One look at the ring on her finger and anyone could tell she’s a Winchester woman.” She exclaimed.

“That’s.. it’s complicated.” Dean looked away breathing heavily. He didn’t want her to find out this way. He had hoped to handle the mess before she found out, but here he was now, in an even deeper disaster. She glared at him and moved past him to leave but he stopped her. “Baby please don’t do this.” He said softly.

“You have a meeting in five, Mr. Winchester.” Was all she said before she left.

Y/n beelined towards the women’s room and broke down finally. She leaned against the sink, her reflection distorted by the tears streaming down her cheeks. Her usually immaculate appearance was in disarray; her blouse was wrinkled, and her carefully styled hair was now a tangled mess. Her eyes, red and swollen, stared vacantly at the mirror as if trying to make sense of the shattered image before her.

Her breath hitched as she tried to steady herself. She clenched and unclenched her fists, the sharp edge of her engagement ring digging into her palm, a small distraction from the overwhelming hurt, but a stinging reminder at the same time. She quickly removed it from her hand and pocketed the ring. She really wanted to flush it down the toilet but it was expensive and she wanted to return it to Dean. She’d decided that she’d only talk to him if he comes clean about the situation or it’s the end of whatever they had.

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Castiel brought Y/n to a cafe near Winchester and Co. The cafe glows with warm light, inviting people from the chilly evening outside. Inside, soft chatter and the gentle hum of an espresso machine fill the air, which smells of fresh coffee and cinnamon. The space is cozy, with dark wood tables, vintage chairs, and shelves lined with books and plants. A barista calls out names, handing out drinks with a friendly smile. In the corner, friends laugh over hot chocolate, while a couple leans in close, deep in conversation. Nearby, a few patrons quietly work on laptops, creating a calm, intimate atmosphere.

The cafe was a stark contrast of Y/n’s mood, she felt gloomy and dark. Inside, people laughed and chatted, but she felt distant, wrapped in a cloud of gloom that even the smell of fresh coffee couldn’t penetrate. The soft glow that filled the room only seemed to highlight the cold emptiness she felt, a reminder of the lack of warmth within her own heart.

“How’re you feeling?” Castiel asked gently after ordering for them both.

Y/n remained silent, her gaze fixed on the table. Another wave of silence settled between them, thick and unyielding, as she refused to answer. Castiel watched her, his eyes full of quiet concern, but he didn’t press, letting her have the space she seemed to need.

“It hurts.” She said after minutes of silence, her voice low and almost in audible. “Cas, it hurts really bad, and I know I have no one to blame, it was me who decided to not give in to his advances, he asked me to run away with him, but could you really blame me? How can I let him throw away years of hard work, his dream that he worked so hard for.” She spoke looking at him and gave her a sympathetic look.

“I understand, but you shouldn’t have broken up with him.” Castiel tried to reason. “He could’ve talked to his parents, he would’ve found a way. But you gave up and he’s torn, he’s not himself Y/n/n.”

Y/n bit her lip knowing, Castiel was right. At least to some degree. But deep down she knew she didn’t have it in herself to bear an upfront rejection. She knew at the end she would’ve been the one left behind. She left him before he could. The insecurity, of not being enough, of not being the one who could provide him the stability he deserves, ran deep. Rachel’s words echoed in her mind, how she taunted her that she is the one that could provide Dean with stability and strengthen his career. How he’s finally accepting the relationship. The thought struck and she interjected, she scoffed before speaking.

“He’s fine. He’s accepted the relationship. They’re getting married, the preparations have started.” Castiel furrowed his brows, unaware of the said preparations or Dean’s acceptance. Her eyes glistened, a hint of unshed tears catching the light as she looked away, blinking quickly to keep them from spilling over. Her expression remained steady, but there was a softness there, a quiet vulnerability she couldn’t quite hide. It was the look of someone holding it together, just on the edge of breaking but determined not to let it show.

“And how’d you know that?” Castiel asked. With a sigh she replied that Rachel told her making Castiel shake his head incredulously. His eyes widened in disbelief. “You can’t seriously be trusting her word on this. She said it to get under your skin.” He added, but she was having none of it. Before either of them could speak further the bell on the door jingled indicating a new arrival.

It was Dean, with Rachel on his arm. She clung to him like a koala, and he didn’t seem indifferent to it either. The tears that she’d held in for so long, flowed freely down her cheeks, unbidden and unstoppable, each one carrying a weight she could barely hold. Her vision blurred, and she took a shaky breath, but the pain in her chest only seemed to grow, raw and relentless. The cafe’s warm light felt too bright, too indifferent, as though it didn’t see the storm raging inside her. When Castiel noticed what she’d seen, he cursed under his breath.

Y/n excused herself to the ladies’ room and Dean noticed his best friend sitting alone in one of the booths. The couple approached Castiel, Dean’s gaze was questioning as he knew his friend was here with Y/n but she was nowhere to be seen.

“Castiel.” Rachel’s high pitched voice resounded in his ears and he turned to her with a bored look. “What’re you doing here alone?” She asked. “Care to join us?” She added before he could reply.

“I’m not alone, I’m here with Y/n. She just went to the bathroom.” Castiel smirked throwing in Y/n’s name to irk her.

“Unbelievable.” She turned to Dean. “She moved on pretty fast huh? One rich man to another.” Dean’s jaw clenched in anger as she berated his woman. Before he could speak Castiel’s voice boomed.

“Rachel, you speak about my friend like that ever again and I’ll make you regret it. I’m not afraid of your father or mine for that matter. So consider this as a polite reminder.” Although he was anything but polite. He really wanted to smack her painted face but he was raised to be better than that.

When Y/n came back the air was tense and to say it was awkward would be an understatement. Rachel glared at the said woman but she didn’t even spare her a glance. Instead, she asked Castiel if they could go back, the man didn’t need to be told twice.

“I know how it looks darling, Rachel’s words and running into them at the cafe, but you should know Dean only loves you.” Castiel tried to encourage her not to give up so easily as he dropped her off in front of the office building.

“Bye Cas.” She whispered completely shooting the conversation down. She stepped out of the car leaving a dejected Castiel behind. He really wanted his friends to be happy, he wanted Y/n to be happy. But the way things are going made him want to rip his hair out. He watched her disappear into the building and drove off with a sigh, in hopes of thing getting better.

Forty five minutes later, the elevator bell dinged and Y/n looked up from her desk to see her boss walking over haphazardly as if he came running and tumbling. He rounded her desk and pulled her chair so she was facing him. With a determined look on his face he kneeled in front of her, cupping her face in his large hands.

“Baby, it wasn’t what it looked like I swear. After you left with Cas, she came in here… she came onto me, she tried to..” He spoke too fast as if he was running out of breath. “She tried to kiss me and I didn’t want to. She wouldn’t leave, so I suggested to take her out so she would stop trying to…-” he pulled her closer, resting his forehead on hers he begged. “You have to believe me.” He whispered.

Despite the chaos around her, she remained stoic, her expression unchanged as the storm inside her brewed. With a monotonous tone she replied,

“Mr.Winchester your relationship with your fiancée is none of my business you don’t have to explain anything to me.”

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Dean and Y/n arrived at their destination and Y/n was sure of one thing; A romantic getaway to the Bahamas is the epitome of paradise. Dean had booked a private beach house for their stay. The beach house was nestled along a secluded stretch of shoreline, offering unparalleled access to the ocean and breathtaking views of the horizon. The house design was seamless with its natural surroundings, with large, open spaces that invite the outdoors in. Expansive glass doors and windows frame panoramic views of the beach, allowing sunlight to flood every corner of the home. A spacious deck extended from the house, leading directly to the soft, white sand.

“You really went all out huh?” Y/n questioned as they both entered the beautiful house. Dean smiled proudly as she took in all the luxurious designs of the place.

“The best for my baby.” Dean said closing in on her and pulling her into his chest. She leaned back with a contented sigh, dropping her head on his shoulder, her arms resting on his’ at her torso.

“Thank you, Dean.” Dean shook his head at words, pressing his lips to the column of her neck, leaving soft kisses in his wake. His lips moved upwards, he placed a kiss below her neck and moved to her jaw.

“You don’t have to thank me sweetheart.” Dean replied tenderly. He is just happy to be here with her, to be able to spend some quality time without being interrupted by anyone. He turned her around to face him, bringing his hand up to rest on her cheek “What do you wanna do today?”

Y/n titled her head to the side, her lips turning into a little pout as she mulled over what she wants to do today. Dean found her extremely adorable when she was lost in thought and all he wanted was to kiss her senseless.

“Lunch then rest. A dip in the ocean in the evening, dinner and then stargazing?” Y/n listed off the day’s plan.

“Careful baby, your PA is showing.” Dean chuckled earning a swat on the arm. “I’m kidding. Sounds like a plan to me.” Dean leaned forward brushing his lips against her ear before adding, “Does the evening dip involve swimming without clothes?” Y/n smirked evilly at his question.

“Well you’re gonna have to wait and find out.” She replied making her way into the large spacious bedroom, with plush bedding and direct access to outdoor spaces, to enjoy the sounds of the waves at night.

Dean groaned at the image his mind conjured up, not being able to stop the dirty thoughts occupying his mind. He quickly followed behind her into bedroom, picking her up and throwing her onto the soft mattress making her bounce lightly. “Slight change of plans, sweetheart. I’m having dessert first.” He said pulling his shirt over his head, leaning down to crash his lips against hers.

“God, you’re insatiable baby.” She murmured against his lips making him grin. The two of them spent quite a few hours making sweet love to each listening to soothing sound of the waves crashing.

After a leisurely and quite late lunch with fresh seafood and tropical fruits enjoyed on the deck, overlooking the ocean, the two of them laid in the hammock enjoying the calm.

As the evening approaches and the heat softens, clad in her bikini and his swim trunks, Y/n and Dean step down to the beach for a refreshing dip in the ocean. The water was warm, the light golden as the sun started to descend. The two of them float in the gentle waves, feeling utterly connected to the beauty around them.

Dean splashed water at Y/n, a mischievous grin forming on his face as he declared for a friendly battle. She wiped her face, removing the water from her face before splashing him back. They continued to dodge each other’s playful swipes. Laughter fills the air as they wrestle, trying to pull the other off balance while feeling the cool rush of water against their skin. Dean managed to push her head underwater playfully drowning her. Y/n got back to to surface glaring her boyfriend who was busy laughing.

“I win.” Dean exclaimed doing an awkward victory dance in the water. She narrowed her eyes at him before an evil thought creeped in her head. Grinning mischievously she grabbed the strings of her bikini top and pulled it off completely, throwing it at his face, rendering him speechless. Dean’s eyes turned dark and lustful, although she was hidden by water from below her neck. “You little minx, come here.” Dean growled reaching for her but she swam away before sticking her tongue at him. Needlessly to say he caught her and the dip in the ocean become even more interesting than anticipated.

Later, as the sky turns to twilight, they had dinner—paired with a bottle of wine, savored under the open sky. The evening culminated in stargazing from the beach, lying side by side on soft blankets as the stars emerge, twinkling like diamonds against the velvet night. The peacefulness of the scene made it feel as if the entire universe is theirs to enjoy in this perfect moment of togetherness.

“Did you have fun today?” Dean asked looking at her. She teared her gaze away from the stars to look at him, she supported herself on her elbow, her head on the palm of her hand.

“This is best day of my life.” She whispered in the stillness of the night.

“Can I make it even better?” Dean asked sitting up and looked at him curiously. He looked at her expectantly and she nodded lightly urging him to go on. “Wait here, I’ll be back.” Dean said getting up from where he sat and disappeared into the house. A few minutes later he came back and he looked slightly nervous than he was before he left. He stopped in-front of her and held his hand out for her, which she grabbed without hesitation and pulled her up to her feet.

“Y/n,” Dean took a deep breath before continuing, “I never thought I'd find someone like you. From the moment I met you, I knew you were special. You made me feel things I never thought were possible. Every time I'm with you, I feel my heart race, my soul sing... and I know that I never want to be without you." Y/n let out a gasp as she realised what was happening. “You're my partner, my other half. Your laughter, your intelligence, your kindness... I could go on forever about how wonderful you are. Honestly I can’t even work properly without you, the company would’ve gone to shit if it weren’t for you.” Y/n chuckled wanting to tell him he’s exaggerating but refrained from interrupting him. “You make me the happiest man alive. And nothing in the world would make me happier than you agreeing to spend the rest of your life with me.” He retrieved a velvet box from his pocket, the box open to reveal a sparkling engagement ring. Lowering himself down on one knee he asked, “Will you marry me?”

“Yes! Yes, Dean I will!” She exclaimed with tears streaming down her cheeks. He quickly slid the ring in her ring finger. The engagement ring showcases a single, exquisite round brilliant diamond set in a sleek platinum band. Getting to his feet he smashed his lips to in a searing kiss, pulling her into him.

“I was gonna wait till the end of the vacation you know, incase you said no. But laying here with you, beside the ocean, under the stars, you were just looking absolutely breathtaking and I couldn’t help myself.” Dean said after pulling away.

“You really thought I would’ve said no?” She asked and he rubbed the back of head.

“Yeah, I mean I haven’t been the best boyfriend to you, we haven’t even been public-“ she quickly stopped him.

“It doesn’t matter to me, darling. As long as you love me I’m good. Though I think now might be the best time to tell your family.” She said showing him the ring on her finger. They’re engaged now, even if they don’t go public they should at least tell his parents.

“Absolutely, sweetheart. The first thing I’m doing when we get back home is telling mom.” Dean had decided to tell his mom about their relationship the minute he bought the ring. He was done hiding their relationship and he doesn’t give two shits what people might say about them. She’s his fiancée now and he’s going to show her off to the whole world. “For now, I just wanna make love to my beautiful fiancée all night long and spend this vacation with her.”

“You’re lucky she loves you.” She replied giggling softly.

“Damn right I am.” He said picking her up and throwing her over his shoulder making his way back to the house. “And she best believe I love her too.”

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