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
The next morning, (y/n) woke up to the sun brushing through the curtains. The sounds of the city burst through the walls. She groaned in pain from the massive hangover that she was stuck with. She turned around in bed to see herself in a hotel room. She doesn’t know where she is, which immediately makes her panic. She sat up and brushed her hair away. She looked on the bedside table to see some Tylenol and orange juice waiting for her with the notes beside them that said “Eat me” and “Drink me.” She took the pill and began chugging the orange juice from wanting something more than alcohol in her system. While chugging the juice, she heard a keypad sound from a short distance, almost as if someone was trying to get in. She got up from the bed and grabbed a vase. Lo and behold, Dean Winchester shows up with takeout boxes in his hand in a casual black tee and jeans. “Good morning (y/n).” He said casually. “It’s you? she asked, still holding the vase. He approached her slowly, “Surprised?” he said with a smirk, “How are you feeling?” He asked, his hand wrapped around her wrist. He brought down the arm that had the expensive vase. “What..?” she responded, still confused and intimidated by how close he was to her. She had to look up at him from how tall he was, his broad shoulders seemed to look down upon her.
“I asked how you’re feelin’ sweetheart,” he asked once more. (y/n) nodded, “A lot better thanks…” She carefully snuck past him and sat down on the bed; she realized her clothes were much different, Her clothes she was wearing yesterday were carefully folded on a chair. She looked down again and saw she was wearing a regular white shirt that was a little too big for her, and when she realized she had no pants, she immediately covered herself with the sheets. “Did you put me in here?” she asked, looking around towards him. She saw him with the takeout box and fork; he started chewing on some bacon and eggs. “Mm-hmm.” he hummed. Dean sat down on a small sofa next to the bed, he began taking a clean fork and put down some toast and eggs on a new plate. “And you undressed me?” she asked confused.
Dean looked up at her while still chewing, “Didn’t have much of a choice, darlin’ it was either that or puke-stained jeans and shirt.” he said. (y/n) immediately had her hands over her mouth in shock. “Oh my god…” she mumbled to herself. Dean then got up from the sofa and carried a plate to her; he placed it on her covered lap, along with a fork and napkins. He sat down on the sofa and continued eating like nothing. (y/n) looked around the hotel room and saw she was in the only bed, and the sofa he was on was way too small to fit anyone. “Where did you sleep?” she asked. Dean gestured his hand next to her; she saw a messy side next to her with the blankets messed up. “Oh god did we…?” she trailed along. Dean immediately shook his head,
“No, Necrophillia's not my thing,” he said immediately. (y/n) took a deep breath, “So we just slept…got it.” (y/n) awkwardly saw the plate of toast and eggs on her lap and picked up the toast Dean got up and went to a different room, he came back a few seconds later with a fresh clean folded clothes, “I asked Benny to bring you some new clothes,” he stated putting them next to her on the bed. “Thank you, you didn’t really have to do that,” she said quietly. She continued eating her toast slowly with a slight hesitation. “I did, you shouldn’t have drank like that in the first place,” he grumbled. Dean began drinking his cup of orange juice when some had spilled onto his shirt. “Shit,” he mumbled, he took off his black shirt leaving (y/n) a whole view of his chiseled toned chest with a unique tattoo. “W-well, I like to test my limits when it comes to alcohol,” she said chewing on her toast.
His eyes roamed at her with a grumble, “Test your limits…you put yourself at risk last night.” He said. He began to place his hands on the bed and began slowly making his way toward her, almost like a lion reaching for a lamb. “I know…” (y/n) said softly, mesmerized by Dean, she couldn’t move or get away, it was like she was trapped. Softly in a low tone, he said, “If you were mine, you would be able to move from the bed, let alone walk…” he got closer and closer to her. “Huh?” she said quietly, not knowing what to say. Dean leaned lower to her hand and bit the rest of the toast off, he looked up at her and held her hand, then began sucking the powder off her fingers slowly. Her breath hitched, and she immediately tried hiding the fact her thighs were clenched together.
He looked down at her with his piercing green eyes. “I’m gonna go take a nice shower, don’t wait up,” he said before getting up from the bed and gathering his clothes. (y/n) let out a long breath before turning her head towards him. “Dean, why did you bring me here?” she asked. He came out of the other room and looked at her, “You’re here because I’m incapable of leaving you alone.” she looked up at him up and down, “Then don’t…you didn’t want me with you anyways, why did you send me that album and shawl anyways? Pity or something?” she asked. Dean came closer to her “I thought because of the way I acted towards you I owed you an apology.”
“For what,” she stated. Dean sat down on the edge of the bed and looked at her. “For letting you believe that…” he took a deep breath. “Listen, I don’t do romance, I don’t do the hand holding, movies, dinner.” “Why?” she questioned. “My tastes are very particular; you wouldn’t understand if I told you,” he said. “Try me. Enlighten me for all I care,” was all she could say. Dean brushed his rough hand on her cheek and then to her lips. Her eyes try to mimic the stare he gives him.
After a few hours, Dean had already showered and was in fresh, new, casual clothes. (y/n) came out of the bathroom in the clothing that Benny had picked out. “Tell your friend he’s got good taste,” she said. She looked forward to seeing Dean writing some stuff down in his notebook. (y/n) gathered her clothes while Dean stood up and leaned on the desk. “What are you doing later, darlin’?” he asked. “Well, I have to go to my job till either 8 or 9, but besides that, nothing. Why?” she asked. Dean could only look her up and down. “I’ll have Benny pick you up,” he said. He came a little closer to her and softly touched her hair down to her lips. “The way I kill a million monsters to be able to kiss those lips,” he said. (y/n) looked up and stood still “I think I would like that too.” she said softly. Dean backed his hand away “I’m not going to touch you…at least not until I have your written consent.” he said. She tilted her head (y/n). “Written?” she asked, confused. “I’ll explain later, cmon let's get you home,” he said to her.
As they both got on the elevator, (y/n) backed up to the back of the elevator while Dean stood beside her, “fuck the contract.” he said before immediately beginning to roughly kiss (y/n). Her hands were on his shoulders, but he grabbed her wrists and pinned them above her while his other hand was down to her waist. Just as (y/n) was about to softly release a moan, the ting of the elevator alerted them. They both got away from each other and acted like nothing happened. (y/n) released a few short breaths and calmly combed her hair with her fingers before the door opened to businessmen. Dean looked down at her and smirked.
When (y/n) and Dean got to her apartment, (y/n) heard music coming from inside. As she opened the door, they both widened their eyes to see Sam and Jessica halfway naked on the couch. Sam and Jessica immediately looked up from the couch. (y/n) turned her head to look away. “Samuel you dog, he had a good time last night. Clearly.” Dean said to (y/n), who was still looking away. “Dean shut it,” Sam said, picking up his pants. Jessica laughed as she looked at the situation. “Hey, you must be (y/n),” Sam said, holding his hand for (y/n) to shake. She awkwardly shook it “Nice to meet you.” she said. “Yeah, sorry for meeting me like this. I got a little sidetracked,” he said looking over at Jessica. (y/n) smiled “Oh no, it’s ok.”
“Sammy, find your shoes, and let's get goin'.” Sam and Jessica had one more goodbye kiss before telling her, “Later, darlin’.” Sam then walked away from her to leave the apartment. “I’ll make sure to email you if anything comes up. You can also email me whenever you want to. I’ll see you tonight,” Dean said. (y/n) took a deep breath “My computer is acting weird; I can’t use it.” she said. “Alright, you have my number. Call me whenever you can. Later, darlin’,” he said, mimicking Sam, he then left the apartment and closed the door. “So Sam seems like a nice guy.” (y/n) giggled.
“Nooo, don’t even start with that. If you’re seeing him again that means something must’ve happened.” Jessica teased. (y/n) could only sigh and walk slowly to her room tossing her house keys to the small bowl where Jessica’s were. “(y/n) you have to tell me what happened!” She squealed. “We have to get ready for work Jess!” she ignored the questions and kept going. “No, no, no, (y/n), I’m your best friend even if it’s TMI, just spill.” she encouraged. (y/n) smiled “You really wanna know?” Jessica nodded excitedly expecting (y/n) to say they had sex when in reality she said “We just kissed.” She nodded expecting more to come out of her. “Uh huh and then.”
“And then what? That was it,” she said. “That’s it?! Only once?! That's super weird.” (y/n) could only hum a yes. She began walking down the small hallway, “And I can tell that’s a new shirt, You never dress in those colors.” she said.
(y/n) was typing away once again, focusing sternly on her computer, Jenna her secretary came in with a smile. “Hey (y/n), I made some lunch for myself last night and accidentally made too much. Thought you might want some, it’s your favorite.” she smiled. (y/n) took the container from her hands. “Thanks, Jen.” Before Jenna was about to leave she remembered something, “Oh I almost forgot your mom sent messages.” Jenna began going through the small sheets of paper. “She said ‘(y/n) I hope you’re doing well, Richard and I miss you and we came to tell you that Flora is graduating middle school in June and we would like you to come to the graduation party. Hugs and Kisses Mom and Richard.” (y/n)’s face scrunched, “As much as I love Flora’m not sure how to feel about the step monster” she giggled.
Jenna looked at her with her eyebrow up. “(y/n) I’m saying this as a friend, man up, I get it Richard kicked you out and your mom never defended you but your sister is 13, she needs her older sister, especially at that age, facetime, and text messaging isn’t enough. Besides you’re a badass editor and journalist for the biggest fashion magazine in the nation.” (y/n) smirked and nodded, “You’re right, I just hated that guy with every bone in my body since I was 16.” she said. “Any other messages Jen?” she asked. “Yes, another from Mr. Winchester.” (y/n)’s eyes widened as she got up, closed the door to her office, and dragged Jenna to her desk to sit down. “What did he say?” she asked. Jenna still a little surprised gave (y/n) the paper to which he wrote down the message.
Hello, Ms. (l/n). I wanted to follow up regarding the agenda we discussed during our last meeting. As we agreed, it’s crucial to ensure we stay on track with the upcoming deliverables. I’ve attached the updated project plan, which includes all the necessary timelines and responsibilities.
Let me know if there’s anything else you need from my side before we proceed.
Best regards, Dean Winchester.
“Everything ok (y/n)?” asked Jenna. “Me? Oh yeah yeah, I’m fine. Is that all the messages?” she asked. Jenna nodded rapidly and got up from the chair to the door, “Thanks for lunch by the way.” (y/n) said. “Anytime.” (y/n) looked at the small sheet of paper and smiled.
When she got out of work, Benny was standing next to a black car with tinted windows. (y/n) smiled and walked up to him, “Hi, Benny. Where’s Dean?” she asked. “He will be meeting us at your destination,” he said as he opened the car door. She climbed inside before saying thank you. As they made their way to a corporate office building Benny helped her out as he led her to an elevator. (y/n) ran her fingers through her hair in nervousness. As they reached the top her eyes widened when she saw a helicopter but no Dean. “I thought he was meeting us at our destination.” asked (y/n). As they began walking towards the helicopter Benny leaned a little to her ear and whispered “Don’t tell him I said this but Mr. Winchester is a bit of a wimp when it comes to flying.” He said. (y/n) looked up to him and smirked. “Do you know where I’m going?” she asked him. “You’ll see.” he sighed. (y/n) was being helped by the pilot to buckle in and adjust the headset on her head.
As they flew she was amazed by the sights of the city. The beautiful lights and buildings that look like they are coming up at her. When they landed there he was, Dean, was wearing a casual-looking tux with a white dress shirt with a regular black blazer. When the Helicopter had stopped the engine Dean went up to the doors and saw (y/n) coming down the helicopter, he took her hand as he led her downstairs.
She walked down a dim hallway into a penthouse. Her steps are the only sound echoing along the room. Dean separated from her and went to a wine cellar only a few meters away. (y/n) curiously let herself wander around. She saw rows of guitars, some electric, and lots of acoustic. She ran her fingers softly along the strings. “You play a lot?” she asked turning towards him, he had wine glasses and a bottle of a newly unopened wine. “Yes, I’ve been playing for as long as I can remember,” he said. He placed the two wine glasses down on a glass table. But when she saw him opening and pouring the wine, there were sheets of paper gathered in a single spot on the table, curiosity took over and she came up to him slowly. “What’s this?” she asked. “It’s a nondisclosure agreement,” he said as he finished pouring the wine and sat down next to her at the head of the table. “To summarize it that means you can’t tell anyone anything about us. To anyone.” (y/n) looked up at him as she clicked the pen. “I don’t say anything other than ‘he was alright.” Her eyes looked into his for a quick moment before the sounds of the pen scratching the paper were lilting to their ears. She set the pen down and looked at him “What now..?” she asked softly.
She was still nervous, afraid to say something wrong that might upset him and kick her out. He leaned forward towards her and told her “Two things, I don’t make love…second I make pleasure, I fuck hard and rough to a point you won’t know your name and can only scream out mine.” she swallowed and let out a soft breath, all she could do was nod and look at him. He got up from the seat and offered his hand for her to take. “I’ll show you,” he said. (y/n) looked at his hand for a quick moment before taking it. He led her down the long hallway before stopping at a door. He looks at her and says “It’s important to know you can leave at any time and the both of will never talk of this again.” He said. (y/n) was confused for a moment, “What’s in there?” she asked. “I said I control people, I like it when people do my bidding, what's beyond here, lies upon that statement. Just know the helicopter is on standby to take you whenever you want to go.”
“I can handle it, Dean open the door,” she said sternly. Dean looked into her eyes for a quick moment making sure she was serious, he took a deep breath before inserting a key into the door and turning it for the door to unlock. When he opened the door and stepped inside she was surrounded by darkness before he turned on the lights. The room was red and dim like his bars but inside lay toys..sex toys. “Oh my god,” she said under her breath. There wasn’t your typical dildo or vibrator. More like whips, buckles, and handcuffs, As she began walking around her eyes ran along the red room, or ‘playroom’ as Dean likes to call it. “Please, say something,” Dean said. She stopped at a row of whips lined along the wall. “Do women do this to you or-”
“No, I do this to women,” he said in a low tone voice, “with women, women who want me to.” he clarified. She started making her way around as he followed right behind her. “So what are you?” she asked turning to him curiously. “I’m a dominant,” he said. “What does that even mean?” she asked.
“It means I want you to willingly surrender yourself to me, and follow everything I say, to please me,” he said. (y/n) scoffed in shock, “To please you? Are there rules for this or something?” she said sarcastically, her smile dropped when she saw Dean’s seriousness on his face. “There are rules. If you follow them I’ll reward you, if you don’t you get punished. Simple as that sweetheart.” he said. “So, you’ll punish me, with these?” she asked. Dean simply nodded “Yes.’’
She looked around for one more moment, “So what’s in it for me?” she asked. Dean smiled at her with a grin. “Me,” he said in a low rumble tone. As they got out of the room (y/n) was still concerned yet somehow excited. Dean took her hand as he led her to the back of the hallway he opened another door to a room with a queen-sized bed, a vanity, and a huge window. But she stopped at the record player sitting on the bedside table, it resembled the one her mother broke on purpose since it used to be her dad’s. “Now, if we were to do this…this would be your room, you can decorate it however you like.” She crossed her arms and looked at him “So..you want me to move in with you?” she asked.
Dean shook his head “No, not full-time, only Friday through Sunday. We can negotiate the particulars. You know I don’t sleep with anyone, So I won’t sleep with you, I’ll only be down the hall.” he said. He took her hand in his once more and led her downstairs back to the living room where they sat on a couch. “So what if I decide to back out?” she asked. “I would understand it completely, but as I said, we will never speak of this to anyone ever.” (y/n) looked at him and observed his face before looking back to his eyes, “And…we won’t talk to each other again?” she asked. “No, I don’t do relationships, I told you…It’s just the way I am,” he said. Dean sighed as he looked back at her “I have a contract prepared, it’s all in there, you would review it and we negotiate from there.” he said.
“Well, what if I’m not sure what to pick?”
“Well, was there a time you had sex with someone and there was anything that you didn’t like doing?” he asked. She could only clear her throat and looked away. “We have to be honest princess for this to work,” he said. For years (y/n) was a bit embarrassing for her to say she was a virgin. She's done stuff to herself and masturbated a few times but that was it. She's never had time for love and relationship until now. “Well, it’s a bit complicated cause…I” Dean tilted his head in curiosity. “Cause what?” She looked at him once more and said “I haven’t done..it.” she mumbled. Dean was taken aback, “You’re still a virgin?” I just showed you-”
“I know. I just, I’ve..done some stuff just not that,” she said. Dean leaned in closer to her and took her cheek with his hand. “Men must throw themselves at you, sweetheart,” he said roughly. She looked into his eyes and all she could see was lust. “No one caught my eye,” she responded. Dean leaned forward and kissed her. She had no hesitation to kiss back, Before she knew it Dean helped her up and walked her to his room, “Where are we going?” she asked.
“We are going to fix this problem.”
He led her to a dark room, it was a regular bedroom, and no sign of the toys in sight. Dean’s hands slowly caressed her body, the lower she went the more he started bending down. His fingers unraveled the buttons on her jeans and brought them down slowly to show her lace panties. He kissed her thighs one at a time, the more he kissed her the closer he got to her wet core. He stood up and slowly lowered her down to sit on the edge of the bed. (y/n) looked up at him as he was doing the work, His fingers looped around the seam of her shirt pulling it up to take it off. As they kissed once more Dean moved his fingers to her back to unclasp her bra that was trapping her breasts underneath the white lace. He pulled the bra forward to take it off her, with her, her breasts now spilled out for him to see. He growled under his breath when he saw them, He leaned into the crook of her neck kissing and nipping at her neck, and (y/n) moved her head away for more access to skin. She moaned at the sensation of him kissing her sweet spot. He backed away and slowly pushed her down to the bed. She lay on the bed as Dean kissed her inner thigh and kissed her cloth-covered puss, his hands running up and down her thighs.
She moaned out his name softly and tilted her head back as she closed her eyes. Dean stood up and removed his shirt showing her once more his chest. He took off his pants and boxers and climbed onto the bed on top of her. He kissed her once more as his hands traced down to the valley of her breasts, to her stomach, then to the edge of her panties. He slowly took them off her and threw them to the floor where their clothes were lying. His hand went up her waist and cupped her breast slowly teasing her nipple. He leaned closer to her, trapping her against him and the mattress, his cock was running along her wet folds and finally, he pushed himself inside her. He let out a sharp gasp from the pain of his thick cock stretching her out. But she couldn’t help herself, she wanted more. Her hands went to his shoulders but he quickly took them off and pinned her hands above her. The sounds of sex were filling the room, “C’mon sweetheart you can take it.” he groaned out. Her back arched in pleasure and the new sensation she was so desperate for. Dean began sliding in and out of her pussy filling the room with squelching sounds from her pussy making contact with him balls deep. “So fucking good f’me.” His hands began tightening around her wrists which were still above her. He began going a little faster which made her tits bounce and her moaning rapidly.
His tip was hitting her g-spot just right she felt a knot in her stomach wanting to unravel. She could feel his cock twitching inside her as he felt her walls tighten. As her orgasm finally let go, liquid came out of her like a faucet. He let go of her wrists before pulling out to spill his cum all over her stomach. His neck leaned back in pleasure before looking down at (y/n) who was panting. He leaned down once more and kissed her softly. “You ok sweetheart?” he asked. She looked at him and nodded. He quickly got up and grabbed a wet towel, cleaning her stomach and her thighs. Quickly she fell asleep.
She was awoken by the strumming of a guitar. (y/n) looked to her side to see no one but unraveled blankets and sheets. She grabbed a blanket and covered herself before heading outside to see where the music was coming from. She took a peek and saw Dean who was only in sweats strumming a guitar in the middle of the night. (y/n) came up behind him and kissed his neck slowly before going up to his jaw. Dean smirked putting down the guitar and taking off the blanket. He led her to his lap where his hands went up and down her body, he kissed her roughly before picking her up and fucking her once more. The sounds of moans and yelling out his name were all they heard for the next hour before they both fell asleep.
Taglist: @applelovesposts @ladykitana90 @cevansbaby-dove
A/N: @steviespookie here damn don't chop chop me. (Im jk ilysm!) ok for once I focused on my school work instead of writing this so that's why it came out a little late today. But yay it's done, I'm already starting for the next chapters ahead so I can just post and write. The comments thoughhh omg yall are so sweet you're making me kick my legs. Hope you guys are staying safe and thank you for the notes and reblogs, and to more followers hello your first a/n on my blog! also if you have some advice on how to spice up my smut scenes PLZZZ LET ME KNOW. other than that thanks for reading and I'll see you guys next week!
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