Warnings: Lots of smut, P in V, Oral (both m and f receiving), BDSM!, Sexual Assault, Stalking, Angst, Alcohol mentions, Dominant and submissive plot, Drug Mentions, Virgin user, mentions of drugs.
Pairing: CEO!Dean Winchester x inexperienced! User
Summary: When her roommate and work partner gets sick, she is in charge of interviewing famous billionaire businessman Dean Winchester for his new bar's grand opening which leads to a passionate and tumultuous affair where she discovers his dark sexual desires, marked by control and dominance. The one catch? He doesn't do romance.
Based on the trilogy Fifty Shades of Grey.
Divider credits: @dollywons, @anitalenia, @selysie
(y/n) woke up alone once again. She stepped into her kitchen in some random clothes from the laundry that had never been folded because of last night. Although she enjoyed it, well, a little too much, there were some thoughts. The way he just tied her up like that aroused her in such a good way. But when she read the contract once more, there were lots of things she wanted to adjust, such as certain kinks she was not comfortable with. “Alright, two large pepperoni pizzas for the new official editors for Runway!” Jessica shouted while carrying pizzas. Castiel had promoted only a few people for a promotion, so they were moving up another floor, which meant having a high status in the company. Well, according to the workers, that is. There have been fewer and fewer people going up the ranks, so when Jessica and (y/n) found out, they decided to throw their small party. Soon, there will be a work party where a special speaker is going to be talking to ‘encourage’ the newly promoted workers. “Also known as the hottest new editors,” Jessica added while pouring in some wine. (y/n) laughed while she took the wine cup.
“God, I still can’t believe it. I started at Runway as an intern, and now I'm a big-time magazine editor” (y/n), smirked, “I’ll take a sip to that sister,” They clanked their glasses together and drank the wine. “I’ll be right back. Go ahead and eat without me; I need to use the bathroom,” Jessica said. (y/n) nodded, and while Jessica went to the bathroom (y/n), took out her laptop and messaged Dean.
“I’m having issues with the paperwork and need to discuss it with you.”
Dean and Sam were working once again; they had just bought new land for them to produce wine. A new approach compared to their liquor products. They had decided to build a vineyard, barn, and all. “Okay, so for the house, we already contacted our usual contractors and workers. They sent us some blueprints for the barn and the house.” Sam was rambling along about the vineyard while Dean was yawning over it. Sam permitted Dean to help design the house and barn for the land. While planning the different rooms for the barn and house, Dean heard the ping from his computer. He saw the message coming from his laptop. He smirked as he responded.
On (y/n)’s side, she was biting her fingernails in nervousness as she saw the notification in the corner of her laptop. He immediately responded.
I’d be disappointed if you didn’t; let’s discuss this over dinner tonight.
She thought hard about it before responding.
It is a contract, I prefer this to be an important meeting rather than dinner.
Dean responded, agreeing.
Before the dinner took place, Dean had asked what she was wearing to the meeting, wondering if it was professional business attire. All she responded was that she was wearing a trash bag. Which gave him note that this was an actual business meeting and not a game she was playing.
(y/n) came up the elevator with the bright colored envelope holding her contract and the pen she was given when she first met him that still had the bright gold Winchester Elixirs logo on it. As she came up the elevator and the door opened, there he was waiting for her in a classy black on black suit. “Ms. (l/n).” He said. “Mr. Winchester, let’s get this going.” She said. He whispered in her ear when they were walking down the hall. “Ain't that one hell of a garbage bag you’re wearing,” he said. She smiled and scoffed, “Business meeting, seriousness please.” she said. They walked into an empty meeting room where he had just been with his brother earlier discussing blueprints. Now, here he was discussing a sex contract. “Super impressive. You outdid yourself,” she said, hearing the echoes of her heels.
“This ain’t my first rodeo sweetheart.” She stopped dead in her tracks and looked at him up and down with a serious face, thinking he meant he discussed this with other girls. He quickly took note and pushed her hair back. “I meant business meetings.” He said before taking a seat. (y/n) took a seat and opened her contract, taking out the Winchester Elixers pen. She’s done meetings before as well, so she treated it as one. Not taking in his charms or jokes. “If you could open your contract to page three, sections 15-20, “The submissive shall submit to any sexual activity demanded by the dominant and shall do so without hesitation or argument.’ I’m not going to be doing everything you say. I have my voice to weather I conset to whatever you want me to do.”
“Affirmative.” He responded by crossing out certain words and writing down his terms.
“If you turn to page five, section named ‘soft limits’” she ordered. Dean turned to the page “With you.” he said reading over the small section seeing if he made any mistakes of somekind she might be calling out.
“First of all i’m not doing any fisting, anal, vaginal, none. Cross it out.” She said, looking up at him. She looked into his eyes as he tilted his head. He nodded as his pen crossed it out.
“In the same page “is the use of sex toys accebtable to the submissive. Dildos are a yes, vibrators are a yes, and spanking, whipping, and gags are ok. Cross out any clamps.” Dean nodded and crossed it out. She paused as she saw two women come in with some food, (y/n) covered the contract with the folder that it came in. They placed the plate of food and some wine upon her and Dean. “Thank you,” they both said.
“It’s alright, only a few staff know what’s going on, they know,” he said. “Please continue.”
She took a sip of wine and continued, “Page five, there are some terms I need you to define.” Dean gestured for her to proceed. “Suspension?” she asked. Dean smirked, even thinking about it. “Hanging on ropes.” She made a face.“What reason do you have for that?” she asked.
“For your pleasure.” She scoffed. “Really?” she said. “And also mine, something to consider,” he said.
“Yeah, hard pass. Roleplay?” she asked.
“We each take different roles and act them in the bedroom, such as a monster hunter and damsel in distress.” He explained. (y/n) nodded. “I’m ok with that,” she said. Dean smirked as she wrote down the definition on the contract for herself to keep. She turned to a different page,
“Page 4, Section 2, 'Is bondage acceptable to the submissive?’ Rope is fine, leather cuffs, handcuffs, I’m not using tape, and please give an example what’s other?” She asked. Dean leaned back. “Cable ties,” he said. (y/n) smirked as she wrote down the example. “And can I just say how impressed I am that you take this business meeting very seriously? I’ll throw in a sweetener for you, sweetheart. Once a week, on a night of your choosing, we go on a date, like any other couple, to dinner, a movie, or whatever you want.” (y/n) smiled to herself. “I accept, thank you. That’s all I needed to discuss with you today. Thank you again for meeting with me.” She said, putting the contract in the folder, “I’ll make sure to look through the changes and make my decision by the end of tomorrow.”
“You’re leaving?” he asked, getting up and walking towards her as she was still sitting down. “Yes,” she said. “Your body is saying otherwise, princess.” he came closer to her. “Your legs, the way you’re pressing your thighs together under the table.” His hand came to her arm, softly running over her skin. “Whenever I touch you. I can feel the hairs on your arm stand, along with goosebumps. You’re change in breathing, and you’re flushing…not because of the wine; it’s the adrenaline.” She was surprised she could tell all that. “Surprised you can tell all that,” she said, still looking ahead, not wanting to face him. Dean moved her hair to one side, revealing the skin on her neck. He leaned in “Do you know how hard it was for me to see you in this dress, and not wanting to fuck you over this table right now. Making it all foggy and wet from me fucking you.” He whispered in her ear. “Sweetheart, I already know you like the back of my hand.” She breathed in. “What did you want to do to me exactly?” She said.
Dean removed his tie, making it loose. “I would help you out of that little dress of yours, only to see those white cotton panties with a wet patch from me. The I would bend you over on this table, and fuck the living hell out of you.” He said to her. She turned to him, finally meeting her eyes with his. “Thank you for you’re time, Mr. Winchester.” She said, getting up and walking out the door. Dean got up as well and met up with her outside, thanking one of his employees for bringing her coat and helping her put it on. Dean smirked at the staff while he led her outside to her car. “This is you?” he asked. (y/n) laughed, “Yeah, had her since college.” She said, looking at her beat-up car. Dean laughed straight in her face. “What’s so funny?” she asked. Dean finished laughing and looked at her, “For a new editor for a fashion magazine and classic rock chick, I figured you would drive somethin’ nice, not whatever this is,” He said, gesturing to her car. She scoffed, “Yeah, well, I’ll buy myself a car when the mortgage for my side of the rent is fully paid for, my bills are paid, and my insurance is paid for.” She said. Before she got in the car, Dean stopped her.
“Are you sure there’s nothing I can do to keep you from leaving?” He asked. (y/n) smiled, “Good night, Dean.” She said softly.
“When will you know?” he asked her. “I’ll know soon, by the end of tomorrow maybe.” She shrugged. She leaned in and kissed his cheek before getting in her car. “Why do I think you’re telling me goodbye Sound of Music style?” She laughed at his reference, “Cause I’m getting in my car and leaving?” She said. She waved her hand and said farewell like how the Von Trapp kids gestured it. She got in her car and drove home back to her apartment where Jessica was waiting.
When she got home, she heard a bang in Jessica’s room that sounded like it was against the wall. Her heart dropped to her stomach; she grabbed a baseball bat they had in a corner and (y/n) was ready to strike. She opened the door to see Jessica and Sam in Jessica’s bed. “Oh my god!” Jessica laughed. (y/n) covered her eyes. “I am so sorry! Holy Shit!” She could hear the sounds of scrambling and footsteps. “You’re good now (y/n).” She opened her eyes and saw both of them panting, and their hair unraveled. “I didn’t think you would come home early. I assumed you were gonna stayed overtime at work.” (y/n) was still a little shocked; she nervously touched her hair. “I-I got let out early. I finished reviewing stuff.” She said. “I’m going to bed. Carry on. I’ll have my headphones on.” She said before leaving the room. “I’m sorry, I’ve got to get going,” Sam said to (y/n). Her put on his jacket while Jessica let him out. They both walked out of the apartment building and said their goodbyes.
Jessica came back inside, shivering, wearing Sam’s jacket. “God, it’s freezing outside.” She giggled. “Hey…you ok?” She asked. (y/n) was out of it, from the contract to what he would do to her. She was shocked. “Yeah, I’m fine, just kinda tired, Jess.” (y/n) smiled. “Well, we need to see what we’re wearing tomorrow for the work party. So get some rest 'cause we are going shopping.” Jessica smiled. (y/n) collapsed on the couch and scoffed. “With what money?” she asked. “With Sam’s money, he gave me his credit card for me to spend as much as I want. God, I love him.” (y/n) smiled, “Do you love him…like really?” She asked genuinely. “Yeah..I think so…(y/n) I like him. A lot. And I know he’s rich and he’s that single gullible guy, but I don’t care about all that. He’s the most amazing guy I’ve dated; he’s like a gentle giant. A gentle moose if anything.” She giggled. “And trust me, I like it when he spoils me and stuff, but I’m able to communicate with him that sometimes it’s too much. But he told me that he was going to the party and that his brother was gonna speak at the work party and-”
(y/n) was starstruck, one that Jessica had finally might’ve found the love of her life but Dean was the speaker at their work party. “Wait…I’m sorry, Dean is going?” she asked Jessica, who smirked. “I knew you would stop me at that part. Now you can see why I need you to shop with me so I can show off what Sam had, and you can show Dean what he’s missing out on.” She smiled. “I can’t do that. But I’m happy for you, Jess.” She smiled. “Well, I don’t care. We are going shopping because the dresses you have are all mine.” She said.
“Ok, this one?” Jessica said, holding up a red one. “It can remind him of a pretty rose.” She added. (y/n) looked at it from afar. “Hmm, I feel like we need something that can bring out your hair and eyes,” she said. (y/n) grabbed a nice satin black dress with thin straps. “This one can bring attention to your body and a nice updo to show off your boobs to Sam.” Jessica smiled. “And that’s why we are editors to a fashion magazine.” She smiled.
After Jessica tried on a few more dresses and finally chose the black one, it was (y/n)’s turn. She opened the curtain so many times, each dress was either too frumpy, too poofy, too old, too skimpy for a work party, but for a club, yes. “Ok, try this one.” Jessica went inside the dressing room. “God, Jess, I’m naked,” (y/n) said, covering herself up. “Relax, it’s not like I haven't seen you before. Turn around.” (y/n) did what she was told, and Jessica zipped her up. They came out of the dressing room (y/n)and saw the beautiful slick dark blue dress with little detailing. It made her chest pop and her legs look longer. “Dean will be drooling, trust me.” After they purchased their dress and ate some lunch, they began getting ready for the party.
“Don’t put too much blush.” (y/n) warned her after last time. Jessica did a simple makeup look with some elegance to it. Simple eyeliner and lipstick make her face pop. (y/n)’s hair was left down with a small clip in her hair. “There, you’re ready.” Jessica had her blonde hair in an updo with some jewelry to match her eyes. As they arrived at the party, their work friends found them and immediately formed their little group. Sam and Jessica had finally introduced themselves as a couple, and their work friends were excited, especially Castiel. Everyone had gotten served a glass of wine, and before anyone drank it, Castiel came upon the podium.
“Hello, my money makers.” Everyone laughed at his small joke. “First of all, I’m extremely honored and eternally grateful that I am your editor in chief. I’m just as excited as you to welcome our new workers who have been promoted. I’m extremely proud of every one one of you. As a magazine dedicated to the art of fashion, we take pride in shining a spotlight not only on the designers and the high-fashion moments but also on the workers who make it all happen. Your hard work, resilience, and creativity are the threads that hold the entire industry together. Thank you for your dedication. Thank you for your passion. And thank you for making the world of fashion as vibrant, dynamic, and meaningful as it is today. Now, it is my honor to introduce my brother from another mother, my friend, the man who made our October issue skyrocket, Mr. Dean Winchester.”
Everyone began clapping, especially the girls who were fans of him and were clearly interested in him. (y/n) saw how they eyed him down as he came up on the podium. “Thank you, you weird dorky dude with angel wings.” Dean had found (y/n); she was wearing a dress that made his hands grip the podium, which made his knuckles white. “First of all, I want to congratulate all the employees who have been promoted. you have shown great skill and great sensability, and were obviously were able to keep up with everything has to be perfect guy over here.” Dean said, gesturing to Castiel. As he continued talking, one of the girls in front of (y/n) was whispering, “God, I wonder why he’s single. Look at those arms,” one whispered. “Yeah, he could choke me with hands all he wants,” the other said. (y/n) leaned in. “I heard he’s gay,” she whispered. The girl’s eyes widened as they continued to look at Dean, who was still talking.
“Second of all, I’m very proud and honored to be one of the reasons why Runway is skyrocketing, and I believe you owe this party to the two employees that made it happen.” Dean looked at the table (y/n) he was at with Jessica. He saw (y/n) clench her thighs while she bit her nails. “Ms. Moore and Ms. (l/n), you have done a wonderful job with the article and managed to keep Cas sane.” Jessica and (y/n) smiled as the people clapped for them. Dean could only stare at Dean and not pay attention to the people around them. Castiel was persuaded to come up to give them a small part adoration. So when Jessica shook Dean’s hand, it was (y/n)’s turn. As she shook his hand with a grip, she nodded. “I’ll do it,” she whispered. Dean gripped her hand a little tighter as he smirked and let the girls on their way. As the party erupted in a small dance, outside were cameras and paparazzi wanting a photo of Castiel or the Winchester brothers. “Mr. Winchester, can we get a photo?” Dean had dragged (y/n), who was in the corner and had his hand on her waist, and they took the photo. He positioned her to a right angle, and the picture was taken.
Jessica was taken to Sam’s nearby penthouse in the city while (y/n) and Dean went back to her apartment to have a little celebration of their own.
(y/n) immediately moved away from the champagne bottle popping. The sounds of Led Zepplin and Metallica rang throughout the small apartment. Dean and (y/n) giggled at her reaction. He poured in the glass of champagne. “To celebrate your promotion and other things,” he smirked. (y/n) rolled her eyes playfully. “Yeah, other things,” she joked. Dean looked at her “roll your eyes at me again and I’ll smack that ass of yours.” (y/n) was taken aback “Oh.” she smirked. They clinked their glasses and drank the champagne. There was a buzz at the door. (y/n) wondered who it could be at this hour?” Dean took the glass from her hands and placed it on the table.
“Come, I have something to show you.” He said, taking her hands. He led her outside, and a man had handed him the keys to a beautiful car. It was a nice, sleek black car and one of the newest models he could find. “Wow, it’s nice. Doesn’t seem like your style, you know?” She smiled, looking at it a little closer. Dean giggled. “It’s not sweetheart,” he said. He took her hands and placed the car keys in her palm. “Congratulations on your promotion (y/n).”
She looked away from him and at the car in shock. “Dean…Dean, that’s a car.” She pointed out. Dean looked at the car, then back at her. “Congratulations, you just passed. That is a car.” He joked. “Dean..I-I can’t.”
“Do you like it?” he asked.
“What are you talking about if I like it? Dean, it’s beautiful. But I have a car.”
“Benny is lookin’ to get a price on it.” Allison rolled her eyes in frustration. Her car was taken away, and now she gets a whole new one. It was a lot to process at once. “Did you just roll your eyes at me, sweetheart?”
He took her in the house and locked the door. He sat on the couch and dragged her body across his lap. “You know why I’m doin’ this?” he asked her. (y/n) who was aroused, giggled, “Because I rolled my eyes.”
“And is that polote to do to me?” he asked, gripping her hips. “No.” she chuckled. “Excuse me?”
“No, sir,” she responded. Dean immediately pushed her dress to her waist and brought her underwear down, which made her whimper from the sudden cold air. He smacked her ass once. And again. She whimpered and moaned, very much enjoying this. He brought her underwear back and helped her up. She got on his lap and kissed him, which he immediately responded to by putting his hands on her waist and kissing her back. But he stopped and looked up at her. “What’s wrong?” she asked. “Nothin’ remembered that I need some stuff to do in the office.” He said. He slowly took her off his lap and put on his coat.
(y/n) sat on the couch as he put on his coat. “You ok?” he asked, touching her face. “Yeah… I just thought…” she went quiet. Dean made her look up at him. “I enjoyed tonight, I really did. I’ll see you at my place tomorrow, alright, sweetheart?” he said. (y/n) looked up at him and nodded. He kissed her forehead and let himself out. As he left, she looked down at the window as he drove away. She took a deep breath in and out before going to bed, wanting to forget how he had left her and to also remember the kiss they shared.
Taglist: @applelovesposts @ladykitana90 @cevansbaby-dove @cleacc
A/N: Hey guys! So, first of all, thx for the support for the last chapter. I really appreciate y'all so much! Thank you for your understanding with my busy life. So right now, this chapter is kinda sucky cause I tried to make it for y'all in time. Anyways, I hope you guys enjoy this chapter. And I'll see you guys next time!
