#fifty shades trilogy

[ribbonsncherries]

The Contract

Warnings: Lots of smut, P in V, Oral (both m and f receiving), BDSM!, Sexual Assault, Stalking, Angst, Alcohol mentions, Dominant and submissive plot, Virgin user, mentions of drugs.

Chapter 2

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.

(4004 words)

Divider credits: @dollywons, @anitalenia, @selysie

“I’m home!” (y/n) shouted as she threw her purse and work bag on the couch, she took off her coat and hung it up, “Jessica come out here I got some good news!” (y/n) heard the ting on her cellphone, she looked at it for a good minute before she began digging through her small shoulder bag to see Dean had texted her. 

‘Let me know any information regarding tomorrow, Goodnight Ms. (l/n).’ 

“God what is it…” Jessica mumbled wiping slobber from the side of her mouth, she looked like she just woke up from a long nap. “Make love to me or something 'cause you’re gonna love me even more.” (y/n) smiled. “So Dean came by my office and-” Jessica’s eyes widened immediately before running up to (y/n) “WHAT! You’re lying! What did he say?!” 

(y/n) laughed “Well he heard about your problem with the photos so, he’s asking you if you want an original photo for Runway tomorrow?” Jessica stayed quiet, “(y/n), If you’re fucking with me you’re out of this house.” She said pointing at her. (y/n) lifted her phone to show Dean’s number. “Just tell me and I’ll let him know right now, he does want to know by today…” she smiled. Jessica jumped for joy while she squealed. “Oh my god! Ok, tomorrow at around 7 AM,” she said immediately running to her room with her computer to prepare for the next day, although it was last minute Runway was more than happy to ask their photographers to take pictures. This included one of their photographers ‘James’. (y/n) got ready for bed and cleaned up her things from the sofa. She collapsed on her bed and covered herself with her sheets. Before she closed her eyes to sleep she texted him. 

‘Hello, Mr.Winchester. Sorry for the late message. Thank you for doing this for Runway, I was I was just wondering if tomorrow at 7 a.m. would be a good time for you to come to our studio.’ 

‘Yes, of course, that’s a good time for me. After the shoot do you want to grab some breakfast?’’

(y/n) didn’t know what to say or think, all she knew was that she was stunned, she took one more glance at the text and saw it was real. He did ask her out for breakfast. Was he interested in her? Or was this a business casual thing? She began typing away at her phone. 

‘Sure, I would love to thank you :)’

‘Good night Ms. (l/n), see you tomorrow.’ 

(y/n) felt like she released a huge breath. She couldn’t believe this at all, the billionaire man every girl wanted, asked her for breakfast. “Holy shit” she sighed out before covering her face with a pillow in disbelief. 

The next day (y/n)’s alarm rang out at 5:00. She was confused, she set her alarm for 6:00. “Wake up! Rise and Shine!” Jessicas shouted out from her door. She came into her room and opened the curtains to the morning dawn. “You’re insane.” (y/n) mumbled as she turned around. Jessica went to her side grabbed (y/n)’s sleeping mask and snapped it back on her face. (y/n) immediately got up and dragged Jessica down to her bed “What the fuck?!” she shouted while Jessica just laughed “That never gets old! C’mon sleepy head get ready, you’re gonna see your rich boyfriend.” she teased. (y/n) threw her stuffed elephant at her. “Shut up,” she mumbled as she removed her sleep mask and ran her hand through her face and hair. Jessica warmed up some coffee for her and (y/n) in their assigned mugs. As (y/n) stood in the shower, she could only think of his rough voice and his biceps that were underneath his flannel when he came into her office. As she washed her hair the warm water made her suddenly flinch as she thought about his rough hands around her waist, and thighs, Kissing her softly. Before she was about to release a moan “(y/n)! It’s 6:00! We have to get to the office by 6:30!” 

“Shit!” she shouted. She quickly washed the soap out of her hair and turned off the shower. She dressed in casual flared jeans, Dr. Martens, and a nice comfortable shirt just enough to barely show cleavage. Jessica made two sandwiches and handed (y/n) her bottle of coffee. They quickly scrambled to their car and made their way to the Runway Headquarters. (y/n) and Jessica looked out the window to see a slick 67’ Chevy Impala parked in the private garage. “Woahh,” they said in unison. As they began getting out of the car (y/n) took a good look at the sleek black car. “C’mon (n/n) James just messaged me he’s here already. 

James began taking pictures of Dean. He was in his usual Black Tux with a gray tie, his hair combed out and messy, just the way he liked it. He was standing normally and looking into the camera while James was taking the pictures but he couldn’t help but look over James to look at (y/n) who was only a mere feet away from him with Jessica. “Thanks again for doing this Mr. Winchester,” Jessica exclaimed blowing her nose in the distance. Dean looked at her for a moment and nodded his head “I’m happy to help.” he said. James looked through his camera and realized Dean had a straight face the entire time. He looked up at him and saw he was looking at (y/n) “Uh..how about we try one with a smile this time?” James said with his smile to try to encourage him. As the flashes continued Dean’s facial muscles didn’t move an inch ‘’right…guess not.” mumbled James. 

Jessica leaned into (y/n)’s ear “You realize that his eyes are literally glued to you. He hasn’t stopped looking at you.” she whispered. (y/n)’s lips slightly curved to a smile “He asked me to go for breakfast after the shoot.” She whispered back and cleared her throat. Jessica smiled and teased her with a slight nudge and giggling. 

When they were finished Jessica went home on her own since (y/n) was getting driven by Dean’s assistant Benny. James went up to (y/n), “I kinda need to thank you too, This is gonna look great on my portfolio.” (y/n) smiled at him politely, “Of course, anytime for me and Jessica’s favorite photographer.” James laughed awkwardly, “Are you doing anything later?” 

While James was talking with (y/n) he felt his jaw clench at the scene so he went up to them and stood next to her “(y/n), we should start heading out.” (y/n) looked up to him confused “Now?” she asked. Dean nodded his head before he saw her saying goodbye and giving him a friendly hug. “I’ll see you tomorrow James.” She smiled. Dean gave him one last look before catching up with her.

“Is he your boyfriend?” he asked her. (y/n) looked up at him “Who?” 

“The photographer.” 

(y/n) laughed like it was a joke “James? He is a very good friend and long-time co-worker of Jessica and me.” She put it simply as she continued walking with him. “I saw the way he was looking at you,” he said in a rough voice as he began unbuttoning the first two buttons of his dress shirt. “He’s more like a family friend you’d invite to a barbeque.” she scoffed. When they walked to the parking garage (y/n) stopped dead in her tracks as Dean walked towards the Impala. “That’s yours?” she asked shocked as she caught up with him. “Yes, family car that’s been with me and brother for years.” He said. (y/n) smiled at the sight “Wow, it’s a beautiful car.” she sighed. “Thank you.” She was confused when she saw him open the door for her and looked around the garage. “I thought Benny was going to drive us?” She asked. “No, he’s on his day off, I’ll drive you.” (y/n) got in the car and Dean closed the door, walked to the other side, and got in the driver's seat. He whipped out his keys and turned on the car making the engine purr. (y/n) smiled to herself when she ran her hands along the interior of her door. Dean smiled small when she wasn’t looking and began taking the car out of the parking garage. 

“Here you go, is there anything I can get you both?” asked the waitress. Dean looked at (y/n) for a quick second before he shook his head, “No thank you, we’ll call if anything.” he said. The waitress nodded as she walked away. (y/n) smiled before looking up from her food to his eyes, “Thanks for this by the way.” she said as Dean started eating his pie. He noticed that she was trying to pretend everything was good and cool but he could see the small hints of red in her cheeks and ears, and her jaw and shoulders were tensed. “You seem nervous?” he said as he took a bite of his pie. (y/n) laughed a bit. “Well this is my first time with a businessman and you seem intimidating.” Dean scoffed as his lips curved to a small smile. “Not to mention very high struck,” she added on. Dean looked at her and observed more of her body, “I'm used to controlling things and getting my own way.”

“That must get pretty boring easily.” she smiled. Dean scooted her plate closer to her “Eat.” he ordered. (y/n) dug her knife into the small batch of pancakes and drank some orange juice that was beside her. “Tell me more about you. What’s your family like?” he asked. (y/n) stopped chewing for a minute and continued once his words were processed and she swallowed. “My family? Well, My dad is out of the picture in my mom’s life since she doesn’t like him very much. My mom and stepdad live in California, I have a little sister named Flora who lives with them over there, I try to see them at least twice every year. I’m rambling aren’t I?” she laughed softly. “I’m sorry.” she apologized. Dean smiled a bit “It’s alright, I did ask about the topic, didn’t I? Tell me more about your father.” He asked. (y/n) smiled, “he liked music, especially romantic ones, he was always that sappy guy when talking about my mom when they were together.” she smiled remembering. Dean looked at tightening his grip around his cup of coffee. “Are you one?” he asked her. She looked up at him confused “Am I what?” she smiled. 

“A romantic?” 

“Well, I’m a writer for a gossip magazine, sometimes I have to be.” she smiled. His smirk went down a bit. “Thanks again Jessica is so beyond ecstatic and-” 

“I have to go, I can’t do this..” he mumbled, he got up from his chair immediately “What?” she questioned softly. “I’ll walk you out (y/n).” Did she do something wrong? Did she say something that somehow upset him? These thoughts in her head were everywhere, As Dean paid for the bill (y/n) had enough of waiting for him so she just walked out. “(y/n). (y/n), I’m sorry but-” 

“Do you have a girlfriend or something?” she asked. Dean looked at her “I don’t do the whole romance hand-holding girlfriend stuff.” (y/n) rolled her eyes in annoyance as she walked to cross the street. “What the fuck does that eve-” 

“Watch out!” he shouted, a speeding car had almost hit her, he grabbed onto her arm and pulled her into his chest on the sidewalk. She looked into his eyes as his piercing green eyes looked into hers. His rough hand grazed upon her cheek as she rested her face on his hand. “(y/n) You need to listen, I’m not the man for you, you need to stay as far back from me as possible,” he said with a low rumble. 

“Dean wha-” 

“I have to let you go…” he said. He took his hand off her face as she backed away from him. She looked at him one more time with an angry expression. “I don’t understand, but I’m tired of this, whatever this is anyway. Bye, Mr. Winchester,” she said as she crossed the street. Dean’s eyes followed her every move as she crossed the street until she disappeared when she reached the end of the block. 

As another few weeks passed by, The article about Dean in the magazine made a hit making this month's issue one of the biggest ones yet in Runway. (y/n) was working on a few finishing touches on a new article she was working on with Jessica, a small beep rang from her desk phone. “Ms. (l/n).” Jenna rang on her desk phone. (y/n) clicked the button to answer. “Hey, Jenna. What’s up?” “Castiel wants to see you quickly,” she said. (y/n) was a bit in a mood but this was her boss she couldn’t say no. “Send him in, thanks Jenna.” Castiel came in with a big smile on his face. “There is one of my two heroes! Since our department finished the article and the photographers did that photo shoot we are partying tonight at the new Winchester bar and you are one of the VIP guests for making this happen.” (y/n) smiled and shook her head. “I can’t, I don’t do parties or bars; it’s crowded everywhere, and there is always some couple having sex that occupies the bathrooms,” she said putting her pen to her bottom lip from habit. “But this is Winchester Elixers, this is not one of those cheap bars you and Jessica go to. It’ll be fun.”

Castiel could see her facial expressions on not wanting to go, “Listen it’s fine if you don’t want to but, it’ll be fun. Hope to see you there,” he said with a warm smile. He said as he began walking out of her office. The more (y/n) thought about it the more she wanted to go, after this whole dean situation she needed to be let off some steam, even if it was at his bar he opened up. “Cas!” she said walking to her doorframe. Castiel turned around “I’ll go.” (y/n) smiled. Castiel looked beyond happy, “You sure?” he asked. (y/n) nodded her head as Castiel smiled even bigger with his eyes. “I’ll see you and Jessica tonight,” he replied as he walked down the hallway. 

“Ok, you’re putting on too much this is a lot even for me.” (y/n) said, Jessica was putting on a tremendous amount of blush since apparently the amount (y/n) put on was too little. “God Jessica ’m not a tomato.” (y/n) laughed. “Well, I'm sorry it was bothering me it looked like you had just two circles on your cheeks.” She joked, (y/n) grabbed a makeup wipe took off the excessive amount of blush, and left little on her cheeks. They both looked at each other in the mirror as they released a deep breath “We deserve this” Jessica sighed, and their doorbell rang, “Huh, he’s early.” Jessica mumbled assuming it was James who wasn’t going to drink that night and was their driver. While she went to get the door, (y/n) began putting on her lip liner and lipstick to complete her nice basic look. “Package!” Jessica shouted. (y/n) immediately ran to the living room assuming it was Jessica’s. Whenever either roommate got a package they opened it together for fun. “I hope it’s those shirts I ordered a while ago,” Jessica said as she looked at the address. “To (y/n) (l/n).” Jessica took out the note paired with the giant box as she gave it to (y/n). “Echoes of emotion, and the visions of a fool, echoes of forbidden ground’-”

“And it’s too good to be true..’, that’s Fleetwood Mac, Love is Dangerous.” (y/n) said while confused, she opened up the box to reveal an unopened copy of the first print of Rumors that was originally made in 1977. (y/n)’s hands started shaking when she saw a purple and black shawl, this could only belong to the Stevie Nicks. She immediately put it down along with the album carefully. “This has to be from Dean, this is too much, he’s fucking insane I'm sending this back,” she said. Jessica pulled her aside as (y/n) put down the box, “No, (y/n) you’re not sending them back, if he wants to chase you he can go right ahead, don’t feel obligated to send shit back just cause he bought them, if I were you I would fucking keep it, hell if he pulled some shit as he did to you weeks ago I’ll resell it.” Jessica spoke with confidence to her friend. (y/n) nodded as she put the box in a safe space. “Let’s just forget him and go to this bar and have fun 'cause we worked our asses off, we deserve this.” (y/n) nodded once more and smiled. A honk beeped out the window. “That must be James, we should probably get going.” 

The bar was crowded, of course, people were dancing and grinding on each other. People were drunk and just having fun. Castiel welcomed (y/n) and Jessica and offered them drinks. It had a current party atmosphere and was fresh, brand new, and open to the public. (y/n) and a group of her co-workers gathered around a table surrounding shot glasses with Tequila in them. (y/n) had already had a few to deal with the anger she still had for Dean, especially since she was at his bar. “Shots! Shots! Shots!” They shouted. “Drink all of it ya’ll!” everyone in that group drank the tequila shot but still a little lingered in (y/n)’s throat which caused her to cough and laugh drunkenly. (y/n) laughed and laid her head on James’s shoulder “I gotta pee!” she shouted hoping her message would follow through the loud music. She stumbled through the crowd to the long line leading to the bathrooms. She took out her phone to Dean’s contact and as she was about to delete it she smirked to herself and was going to give him a piece of her own mind. 

Dean however was doing paperwork in his office and heard his phone ring. He saw who it was and he was confused. “You ok?” Sam asked who was sitting across from him. Dean looked up to his younger brother and got up from his chair. “I’ll be right back give a second.” He said before walking away. “(y/n)?” he answered. 

“Yup, It’s me (y/n), sooo I have that album thanks and a shawl that works perfectly fine ‘m sendin' them back, actually no ima resell em. But thanks a lot,” she slurred. Dean furrowed his eyebrows confused “You’re welcome, sweetheart where are you?” She laughed through the phone, “Don’t call me sweetheart, ‘n its none of your business to know where I am~ I’ll tell ya anyways ‘m in line cause I have to use the little lady room~” she said. Dean could hear the music and laughter through his phone, “(y/n) have you been drinking?” he asked sternly. She giggled through the phone once again, “Yeah~ so what? You little Mr. Fancy Pants.” she laughed. (y/n) looked over towards the girl next to her in line, “What a bossy guy huh?” she asked. Dean cleared his throat “(y/n) Listen to me, I need you to go home right now.” 

“Oh my god~ you’re so so bossy in the first half it’s “(y/n), do you wanna go to breakfast?” She giggled as she made her voice low and gruff like his, “(y/n), do you wanna got for breakfast? No, sweetheart stay away, I don’t need you, sweetheart. Get away~” she laughed. “That’s enough, tell me where you are right now,” he said sternly. 

“‘M not tellin’ you shit, but I’ll tell you I'm far away from you like you wanted~” She slurred out, “(y/n) where are-” she hung up her phone and sighed, she looked to the girl next to her once more and smiled, “I showed him huh?” she asked. His phone rang out again to see Dean calling her. She answered the phone, “Listen I had enou-” 

“I already know where you are I’m on my way.” (y/n)’s giggling stopped “wha- Hello?” He hung up this time on her. She looked at her phone and rolled her eyes. And looked to the girl once more.”People need to stop interrupting me I swear.” When she was done using the bathroom she stepped outside to get some air from the crowded bar. “(y/n).” someone called out. She turned around and saw James holding her sweater. “Here it’s freezing outside.” James helped her put on her sweater. “Thanks,” she said. “You ok?” he asked her. She nodded her head. 

“Yeah just never really been this drunk in a while ‘n it’s cold so~” James grabbed her arms and clung her to him. “Here let me keep you warm.” He said. (y/n) tried pulling away but she was too drunk to “No it’s cool I'm good James thanks.” James looked at her flushed face and pulled her closer, “I don’t know when I’ll be able to do this again, (y/n) I like you.” She was confused and dizzy at the same time “Wha? No you don’t” she said. “Yes, I do, very much.” (y/n) scrunched up her face “No~” James grabbed her arms a little tighter to prevent her from getting away “What are you doing, stop, no, no, no.” James began kissing her while she hit him still drunk. A sudden punch to the face hit James, “She said no!” (y/n) knew that voice anywhere. “Dean?” before she said anything else she puked in the parking lot and crouched. Dean immediately came up next to her and grabbed her hair away from her face as she puked. “Don’t look at me,” she said embarrassed. Dean looked away to James who was backing away inside. When she finished she leaned on his shoulder while he gave her his handkerchief that had his name embroidered to wipe her mouth on. “C’mon sweetheart let's get you home,” he said. She looked up at him and wiped her stray hair away from her face, “But I’m with Jessica~” she said. “Sam will tell her.” He said. 

“Who’s Sam?” she asked. “My brother, he’s inside telling her right now.” Dean took her hand and led her inside to get her things. When they got inside they both saw Sam and Jessica dancing together to the music playing Dean went up to Sam and whispered something, he then bent down a little to Jessica’s height to tell her what was going on, she then whispered something back to Dean before he came back to her, “What did she say?” she asked. Dean smirked “She warned me if I tried something stupid she knows a place to summon a demon.” (y/n) laughed as she started moving back and forth. “The world is spinning…why are you spinning?” she mumbled as she fell back and Dean wrapped his arms around her preventing her fall. He held her head to prevent it from falling back, he carried her bridal style, placed her in his impala carefully, and buckled her up. They made their way to the hotel he had still stayed in for the past few weeks. Waiting for her. 

Taglist: @applelovesposts @ladykitana90

A/N: yurrr, the tag list is open! So am I writing the next one instead of doing my assignments? yeah, I'm doing that. First of all, the love for the first chapter omg, I freaking love you guys. and to the new followers, welcome! I'm happy you're here and already interested in my book I'm eternally grateful for you all! Currently, the tag list for this book is open! So message me or go to my inbox to let me know if you wanna get tagged. Thx so much for all the love and support for this book. Until we meet again!

[who-canceled-roger-rabbit]

C. S. Lewis is like the anti-E. L. James in that James's writing has a core of Virtuous™ trad gender norms hidden under a layer of kink, whereas Lewis's writing has a kinky core hidden under a layer of Virtuous™ trad gender norms

[dakotajhnsns]

Dakota and Pedro Pascal at the Stevie Nicks concert in the UK, July 12th.

[5sosprincess]

I'm just a girl. But honestly I always cover the cover page if it looks a little too obvious or I would rather read it on my kindle.

[danclause]

Is anyone willing to write a Christian Grey x reader smut. I am asking a on my knees begging please anyone write me one. He is my new obsession.

Edit: I'm asking if someone could write

[zeroandvoid]

🫦 Christian Grey moodboard 🫦

[peach-and-cherryblossom]

Sometimes I wonder if there's something wrong with me. Perhaps I've spent too long in the company of my literary romantic heroes, and consequently my ideals and expectations are far too high.

-E.L. James, Fifty Shades of Grey

[annstr]

You're the cure, you're the pain

You're the only thing I wanna touch

[hb-writes]

Let It Be

Summary: Emma is stressed and needs to vent, but all of her siblings are busy. Christian finds the time anyway.

Characters: Christian Grey & Emmeline Grey (OC)

Fifty Shades Masterlist

Comfy-vember 2024 Masterlist

—

Emma wasn't asleep, but she easily could've slipped into a nap while she lounged on a blanket in her parent's backyard. It was a perfect day—unseasonably warm and sunny for the middle of autumn—and she was grateful that her Chemistry professor had taken pity on them, canceling their afternoon lecture so no one had to stay in a dark auditorium on what would probably be the last nice day until spring.

She usually would have stuck around campus to hang out with her friends, but home had been calling her name, meaning the place where she grew up, and not her apartment in the city or Christian's penthouse. Her parents weren't home from work when she arrived, but Emma didn't mind the time alone—or more accurately, time to be alone in Ryan’s presence. She hadn’t seen him since they arrived, but assumed he was watching over her in some manner.

Emma tried not to think about it. She tried to tune out her security detail's constant presence. Tried to imagine he wasn't pacing the yard or constantly looking over to where she was laying in the sun with headphones shoved deep in her ears, a third Beatles album blasting in her ears as she held her eyes shut, cherishing the feel of the warm sun on her skin. With those things in place, she was just able to imagine she was alone.

Emma jumped when something nudged her bare foot and she opened her eyes to find Christian standing above her. He was dressed as if he had come straight from the office, though he had lost his tie and jacket at some point, his shirt sleeves carefully rolled to the elbow.

"Why are you here?" she asked, pulling an earbud free though the music still loud in one ear as she propped herself up on her elbows.

"I ended my day early."

Emma lifted her sunglasses to study her brother. "The Christian Grey I know doesn't end his days early."

"And yet here I am," Christian offered with a smirk that Emma was certain had reached his eyes even if she couldn't see through the dark tint of his sunglasses.

Emma thought of pushing further, of asking why he was here specifically, but she didn't bother, assuming that he was only here because she was here. Because Ryan had told him, or because Ryan had told Taylor, who then promptly informed Christian.

Emma couldn't properly remember the last time someone hadn't known precisely where she was located, which was part of the reason why she had been laying out in the backyard tuning out the world to Beatles album after Beatles album to begin with.

She lowered her sunglasses. "Well, what did I do wrong now?"

"Something, I'm sure," Christian answered as he glanced around the yard. "Your class was canceled?"

"Yup, Dr. Ellis is my new favorite person," Emma answered. "You should give your employees the rest of the day off. Might improve your approval rating."

"A company can't run if—"

"You're not working and the company seems to be running just fine without you," Emma interrupted before resting her head back on the blanket. "And anyway, I was really referring to your personal employees, ones like Ryan." Emma tilted her head in the general direction of where she assumed her security was standing—or more likely, pacing.

"I already did," Christian answered. "He's inside debriefing with Taylor right now.

"Figured there's no point in making them both work if we're spending time together."

Emma pushed herself up on her elbows again.

"I thought you were busy this weekend."

"I am," he said, "but I could make myself available for a few hours right now. Do you still need to talk?"

A bit of emotion swelled in Emma's chest. She had put the message in the group chat with her siblings, asking if anyone wanted to spend the weekend at their parents' home, or even just visit for a bit. 

Emma hadn't expected her sister to be free. She knew Mia was still in California. And Elliot was apparently working out of town, an unfortunate coincidence. Christian had declined, too. He had some charity thing to attend and work meetings, and yet, here he was.

"Come on." Christian held a hand down to his sister to pull her up to her feet. "Let's take a walk."

"How did you know I wanted to talk?" she asked as she stood and slipped into her sandals, her hands still grasped in Christian’s for balance.

"I'm your brother, Em," he answered. “I just know.” 

It was that simple, and Emma once again felt the warmth of emotion swell within her as they fell into step.

"So, you want to take out the earbuds and tell me what's—"

Christian stopped himself when Emma held out her free earbud.

"Can we listen to a song first?" she asked. Christian accepted the earbud and Emma fished her phone out of her pocket, the intro of "Let it Be" coming through as Emma hit the button to restart.

They were both quiet for the song's duration, walking side by side for the entire 4 minutes and 3 seconds, and Christian waited while Emma stopped to delicately wrap the cord of her earbuds before stashing it away in her pocket along with her phone.

"I think that's my favorite song," she said. "It calms me."

"Me too," Christian agreed. He had half a mind to once again prompt Emma, to ask her what she wanted to talk about, but she spoke up before he could.

"What's your favorite song?" she asked, as she started walking again.

The temptation to lean into efficiency,to steer his sister back to the matter at hand, was strong as ever, but Christian allowed himself to let it be. He knew Emma would come out with whatever was concerning her in due time, and it wasn't as if Christian had any place else to be for a few hours, so he pulled out his phone and began searching through his own playlists, needing only a moment before he pressed play on a new rendition of a classical piece that was his current favorite.

"I like it," Emma said. "It's calming."

"It is," Christian echoed.

"Text me the name," Emma said, and Christian nodded as he copied and pasted.

Emma pulled her phone from her pocket and scrolled through her brother's message, a whole list of songs there on her screen.

"They're all calming. You'll like them," he offered. "It'll help with the stress."

"How do you know I’m—?"

"I'm your brother, Em," he answered as he put his phone away. "I just know."

—

Fifty Shades Masterlist

Comfy-vember 2024 Masterlist

[azrielsbxtch]

The soundtrack of the Fifty Shades trilogy….I’ll forever be obsessed

[raidermomma]

Me: I will never read Fifty Shades of Grey

Tumblr: Someone wrote a Red Dwarf version

Me: God help me I am going to hell.

[ribbonsncherries]

The Contract

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.

Chapter 1

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.

(3473 Words)

Divider credits: @dollywons, @anitalenia, @selysie

 “Please!” her roommate Jessica repeated yelling at her. (y/n) poured hot water into a coffee mug, placed a tea bag in the water, and began mixing with a spoon. “What did I tell you about yelling? Your throat is already damaged from the yelling at this point.” she scolded. Jessica sighed as (y/n) passed her the mug filled with tea. Jessica pouted as she poured in some honey. “I just need you to do this one thing. One thing.” (y/n) and Jessica are partners for a famous magazine ‘Runway’, Jessica and (y/n) were going to interview famous billionaire Dean Winchester who had just opened a new bar in their city. Dean was a longtime famous topic in Runway cause of the girls who swooned over him since he was single, so Runway only thought of the dynamic duo to interview him the next day. If only Jessica hadn’t become a walking disease. 

“It’s just one interview without me you can do this. Besides I’ve already got some questions written down, just press play on the tape recorder and ask away,” she said. (y/n) rolled her eyes as she drank her tea, “I’m only doing this cause Castiel is going to beat us up if we don’t get this article in.” she agreed. Jessica smiled as she lifted her arms. “Yes! (y/n) saves the day again!” she said before coughing up a storm, “ow.” Jessica thought for a moment and grabbed the laptop sitting across from her on the coffee table, just as she was about to reach out (y/n) grabbed it before she did, “Not a chance. You need to stay and rest, that means no working until you feel better.” Although Jessica groaned she agreed. “Night roomie,” she rasped getting up from the couch and to her room. 

The next day (y/n) got up early and did extra research since she was doing this alone. She quickly called Castiel to inform him that she would be able to do this alone and quickly for the article to get posted and submitted by next week. She dressed up professionally yet comfortably since this was a grand opening at almost 9 in the morning. She dressed up in black dress pants and boots, pairing it with a basic black shirt and sweater. She grabbed what she needed and met Jessica in their living room who was blowing her nose into her tissue. “You're so lucky you get to meet the Dean Winchester,” Jessica complained. (y/n)’s lips curled into a smile as she heated a bagel. “You’re a dork, Jess,’’ she laughed. Before she left (y/n) packed her bag with her media pass, notebook, and tape recorder. As she was putting on her boots Jessica immediately got up. 

“I almost forgot” she rasped. Jessica dug through her work bag and gave (y/n) a piece of paper with questions to ask Dean. “Ask him these would ya.” (y/n) looked up to Jessica while she offered a sheepish grin. “Good luck.” (y/n) thanked her before starting her car. As she headed to the bar nerves were kicking in. She’s always had Jessica by her side so this was strange going to interview someone famous without her. When she pulled up into a parking garage she put on her media pass around her neck and grabbed her bag. As she began getting closer to the bar she saw a crowd of people, especially paparazzi and girls screaming his name. She took a deep breath in and began squeezing her way to the front. “Excuse me!” she called out to the event worker. She flashed her media pass. “I’m here with Runway magazine I think I’m supposed to be-” 

“Media cannot pass this barrier.” The man said. (y/n) puffed her cheeks in frustration. “Yeah, I know I work for Castiel Novak, the editor-in-chief. I know he’s a good friend of Mr. Winches-” 

“Don’t care stay behind the line.” (y/n) groaned out anger and clenched her teeth in annoyance. When Dean Winchester came by the Paparazzi began crowding amongst each other. Everyone shoulder-to-shoulder. She tried to get past through but there was no way around it. As Dean cut the ribbon he saw the commotion going on beyond the bright flashes of the camera pointing at him a woman with a large camera pushed (y/n) to the ground. Dean whispered to his assistant Benny, As (y/n) got up she looked over to the entrance where a man in a suit was looking straight at her. Benny went up to the barrier of media, “Hey, girl in the sweater.” (y/n) looked up and pointed to herself, Benny nodded his head as he made a signal with his hand for the reporters and paparazzi to move, (y/n) now had a clear path and was invited inside by Benny through the back. As she was invited inside she was told to stay there until Dean was available to talk to her. When Benny left she took in her surroundings. It was dark, the light sources only being from the warm lights of the fake candles and rustic chandeliers. She saw many pool tables as well as booths next to it. A bar in almost every corner of each room she was surrounded by. She began walking around slowly clenching her bag, everything was quiet besides the commotion of screaming girls and paparazzi, and the slow clacking of her boots. She approached the pool room where there was a row of 5 pool tables and a bar. Her fingers ran through the smooth green velvet and smooth brown wood. 

“Do you play?” said a deep rusty voice. (y/n) jumped and turned around only to be face-to-face with Dean Winchester. He was tall and intimidating from his broad shoulders down to his dress shoes, His emerald eyes gazed upon her as he asked the question, and she quickly took her hand away from the table. “I’m so sorry, they just told me to wait here.” she smiled awkwardly. Dean could only keep a stern look with a slight smirk while (y/n)’s smile went down as she cleared her throat, “If it’s ok with you, Runway would like to interview you about the grand opening.” she said quietly. 

“I asked if you play,” He said. (y/n) glanced at the pool table, “sometimes, I’m not very good at it.” she uttered. “Let’s take a seat,” he said before leading her to the bar near the pool tables. She sat on the stool, put her hands on her lap, and looked down nervously. ‘Damn he is hot’ she thought. As he came around the bar he said “Cas told me there were supposed to be two of you.” (y/n) almost forgot. “Oh yes, well Jessica came down with the flu and it’s pretty bad so I’m alone for a moment.” she smiled. “Want anything?” he asked as he began grabbing glass cups with the bar logo on them. (y/n) was taken aback, “drinks this early?” she asked him. Dean looked at her while he poured whiskey for himself. “Doesn’t hurt to drink early once in a while,” he said looking up at her with his offer still standing. “Sure, I’ll take red wine if you have it please, and thank you,” she said.

“We can begin with that interview if you want,” Dean said as he poured her wine and slid the cup toward her. (y/n) nodded once more as she began taking out the voice recorder and notes to write along with Jessica’s questions. She began digging through her bag in search of a pencil or pen she had forgotten to pack. “Fuck” she muttered to herself. Dean dug through the inside pocket of his suit and handed her a pen with his company name on it. ‘Winchester Elixirs’. She saw the pen handed to her and gently took it. “Thanks” she mumbled. She pressed record on the voice recorder and set it down between them. She cleared her throat “Um, so, this is for the special article for Runway Magazine, You are young at the age of 26 to have made a popular chain of bars, to what do you owe your s-” “To what do I owe my success?” he interrupted and scoffed. She looked at him awkwardly and nodded “Yep…” 

“Seriously?” 

“Yep…” 

“Okay um… We know that you are a business man but do you enjoy doing things outside of work?” She asked pressing the pen to her bottom lip and looking up at him to answer the question. 

Dean had his hands on the edge of the counter, his grip tensed with his knuckles going white. “I enjoy many physical pursuits as well as managing cars.” (y/n) nodded as she went through Jessica’s questions “You're unmarried- wait no. um… you had a mother that died- oh my god, I’m sorry I didn-” 

“Do you have an actual question Ms…?” 

“(l/n), but you can me (y/n)” she said. 

“Give me an actual question,” he said. She rapidly nodded and brought it down to look at Jessica’s notes. Her head came back up to look at him, and her eyes dropped with sadness. "Um, what is it like being a successful businessman and having to be a family man with your younger brother?"

Dean smirked thinking of his younger brother Sam, "To answer your first question, yes, my mother did die when I was very young. and my brother was only 6 months old. It's hard but. this is our harsh reality, what better way to just drink through it, why else do you think this empire is up and up, causing people to need to drink their thoughts away. Life, death, lousy interviews." he mumbled. (y/n) looked at him with sadness on her face. "Mr. Winchester, I'm so sorry it wasn't my place to ask that," she said. Dean could only look at her, he could tell she was biting the inside of her cheek and gripping her notebook from embarrassment, "Ask another question, go ahead I'm not gonna kill you." he scoffed, (y/n) smiled softly at him as she looked through Jessica's notes once more.

Are you gay?” she asked him with direct eye contact, her eyebrows furrowed and her eyes widened, she just asked a personal question which he answered and now it's led to this ridiculous answer. As she looked back at her notes, she chuckled awkwardly “It’s written here I’m so-’’

“No, (y/n). I’m not gay,” he said with a small smirk and chuckle. She smiled “I’m sorry Jessica can be a little.”

“Intrusive?” 

“More like curious.” 

He saw her, the way her lips were in contact with his pen. He looked up and down at her taking in her curves, her hair, her eyes. “Mr. Winchester, you’re meeting is about to begin in an hour.” Benny interrupted. “Cancel it, I’m a little busy here,” he said to him before he left. “No, it’s ok I can leave if you want me to,” she said softly. 

His emerald eyes looked into hers, “I want to know more about you.” his voice rumbled. She drank a bit of her wine slowly, “There’s not much to know besides this.” she said glancing at the recorder and notes. “What do you like?” Dean asked. (y/n) was thinking for a second before saying “I like music. Especially old 70s Rock, my dad used to play a lot on his record player all the time when I was a girl.”

“Let me take a good guess, You look like a Led Zeppelin gal to me…” he said observing more of her features as he thought. (y/n) looked down for a minute before she laughed softly. “Well I like Fleetwood Mac mostly, and Derek & The Dominos. Those are what I’m listening to the most right now,” she said. Dean hummed. 

“Let’s continue,” he said. (y/n) nodded once more and began asking more questions Jessica had written down even though she was skipping most of them. By the time they were done (y/n) cussed at herself for not asking many questions and even the ones she did ask were dumb and stupid almost everybody knew the answer to them before they even saw his response. “Thanks for the drink,” she said smiling. “I hope you got everything you needed sweetheart.” He said to her. Though she knew he said that to other girls it made her stomach flutter. “Thanks, I think you only answered about five questions,” she said before leaving. “Thank you for your time.” she smiled before leaving the bar. Dean looked down at her bag to see the slip of paper halfway out, so when she turned her head he quickly grabbed the piece of paper from her bag and pocketed the questions, it was then he realized she accidentally took his pen with her. 

When she got in her car she sighed to herself and let out a deep breath. “Holy shit,” she muttered in her head all she could think of was how hot Dean was. The pictures the press took of him were no match for how he looked in person.

When she got home she saw Jessica on her computer with tissues surrounding her. “Jess, what did I tell you about worki-” 

“I fucking love you so much (y/n),” Jessica shouted as the sounds of clicking surrounded the living room. “What?” (y/n) asked in confusion. Jessica looked up at her and smiled big “Dean just emailed me and he answered every question, this is perfect.” She exclaimed. “So…” She said with mischief. (y/n) took off her sweater and threw it on the couch, she looked at Jessica with confusion, “So what?” she asked. 

“What was he like?” Jessica asked with her whole body moving toward her as (y/n) sat down on the coffee table. “Well…he was fine I guess,” she said. Jessica looked at her skeptically, “Fine? Just fine?” she said in confusion. (y/n) scoffed as she began taking off her boots. “Well, he was nice he gave me some free wine. He was very formal…and clean,” she said. Jessica laughed “Clean?” she asked. (y/n) thought about him more oblivious to Jessica laughing. “He was nice, Intimidating…very intimidating. I mean I can understand the hype around him,” she said looking up at Jessica who was grinning at her. “Jess… Why are you looking at me like that?” (y/n) smiled. 

“Like what?” (y/n) rolled her eyes before going to the kitchen to make herself a sandwich. “Whatever Jessica.” she sighed. Jessica was curious one last time and looked him up online. She clicked on images and began scrolling, “But (y/n) you’ve got to admit he is so hot.” (y/n) scoffed “Well, he could be when you're into that…kind of…human.” she said finishing making her sandwich. “By the way, I asked if he was gay. That was so embarrassing. He looked at me like I was a freak.” (y/n) laughed. Jessica apologized. “I'm sorry but hey, whenever we see photos of him he has never been photographed with a woman before so I just thought-”

“Jessica have you ever thought that maybe this guy wants to keep his life private I mean he’s already in the media so much.” (y/n) said. Jessica smirked “Awwe look at you defending him.” she teased.

“I’m going to my room.” (y/n) said with a mouthful of her sandwich. Jessica immediately got up and coughed a bit before jumping in front of her. “Wait, (y/n) I'm sorry. Can you make me some of those too?” she asked politely. (y/n) rolled her eyes before going back to the kitchen to make her a sandwich. “Thanks (y/n). I’ll be right back Mother Nature calls,” she said. (y/n) looked over at Jessica’s computer and saw the images of Dean and his dark blonde hair and emerald eyes, She closed Jessica’s laptop before making the sandwich to try and get her mind off him. 

“(y/n)!” (y/n) turned around to see one of her friends, she smiled as he continued walking next to her. “Hey, James.” she smiled. “So, a couple of friends are going to this photography exhibition and going to dinner afterward. Wanna come?” he asked hopeful she would say yes. He has liked her since she got promoted to their floor with Jessica. “Well that sounds fun but I can’t I’ve got a lot of writing to do for the new Winchester article. So I’ll be in my office all day.” she sighed as she stopped dead in her tracks. James’s face went down slightly “No, it’s fine we can hang out some other time.” he said bringing his arm behind his neck and rubbing it awkwardly. (y/n) smiled “I promise I’ll make it up to you guys, we can hang when Jessica feels better so the whole group can hang. Ok?” she said oblivious to what he was trying to do. James nodded before she walked off to her office. She closed the door and sat down on her desk. She opened her laptop and began writing away. 

It had been a few hours until one of her secretaries called “Hi (y/n), Dean Winchester is asking to see you. Do I send him to your office?” she asked. Her heart skipped a beat, and her stomach fluttered once more. (y/n) picked up the phone “Yeah, Jenna send him in, thank you.” she said. She heard the door knock. “Come in!” she said. Dean Winchester came into her office and looked around. He was dressed in a casual red flannel and jeans rather than his usual tux. “Hey, Please have a seat if you want.” (y/n) said, smiling at him. He continued looking more and saw autographs from celebrities and pictures of her and friends. "Did you want a drink? I have some water and apple juice?" She asked politely, Dean pulled out a chair and sat down "No thanks, sweetheart." He said casually

“What can I help you with?” she asked. Dean looked at her like he was observing her. She was worried if she had something on her face or her teeth. 

“Just wondering if you got the email I sent to your partner?” He asked. (y/n) glanced at him from her laptop “Um. Yes she did thank you for that by the way I know her questions were a bit invasive.” she said with her eyebrows up in sympathy. “No, it’s fine I was more than happy to answer them,” he said to her. “Is that it?” she asked politely. “Did you grow up in this town?” he asked her. (y/n) nodded “Yep born and raised.” she said smiling. Dean smirked “I need to pick up a few things, do you know a grocery store near here that sells whipped cream and zip ties?” (y/n) looked at him curiously “Well there’s a grocery store nearby that sells most of those things, it’s actually around the corner of Rose Street,” she smiled “What on earth are you planning? sounds like a torture device” she joked. “Are you baking something?" she asked curious and oblivious.

Dean smirked at her and tilted his head. “Yeah, what would you recommend I get?” he asked. (y/n) thought for a moment leaning back on her chair. “Well, maybe an apron to cover yourself to protect your clothes.” She said gesturing to his flannel. His smirk grew bigger “I’ll just take off all my clothes.” he said in a low rough voice. (y/n) could almost choke from his statement. “Ok…no clothes– I mean no apron…” She smiled and cleared her throat and began taking a sip of her water. “Thanks, how is your roommate feeling by the way?” 

“She’s a little better, right now she's working a little from home but she's having trouble finding a good photo especially the permissions and stuff so-” 

“If she’d want an original I can swing by here tomorrow,” he suggested (y/n) was taken aback. “You would do that?” she asked softly. “Yeah.” It was as simple as that. He agreed and (y/n) was feeling ecstatic inside. Dean took out his wallet to pull out his business card with his number “I’m staying at the Pacifica Lux Hotel call me anytime.” he said before walking out. “Ok bye…” she waved awkwardly. She leaned back against her chair, she mentally smacked her head from how embarrassing that whole conversation was. She took a deep breath before continuing with her work. She decided to wait until she was home to surprise Jessica.

A/N: Hello! I'm already having fun planning this. Fifty Shades is honestly so bad it's good. Trust me, besides the sex scenes, the plot is kind of good, lmao. I hope you enjoy this chapter. Thank you for liking and reposting the announcement, especially to my followers! Again, my suggestion box is open for writing new stories between this book's waiting chapters. Thanks for reading. I'll see you all next Friday!

[malfoyx]

Jamie Dornan

[dakotajhnsns]

Dakota photographed by Justin Bettman during the 2024 Tribeca Film Festival in NYC.

[celeb-fettish21]

Dakota Johnson

[fiftyshadesofhotmess]

C California Style Photoshoot (March 2024)

Loewe Fall/Winter 2023 Campaign

Loewe Spring/Summer 2024 Collection

The Sunday Times Style Photoshoot (January 2024)