ribbonsncherries

[ribbonsncherries]

someone you loved just died of mysterious causes and you look out your window..

[ribbonsncherries]

reblog to have him saran wrapped on your blog

[ribbonsncherries]

Cyclone Ranch .°˖⋆ 𓃗 .°˖⋆

⟢Warnings: Mentions of tornadoes and twisters, very bad descriptions of weather and climate, Dean being rude asf, mentions of lost child, fluff at the end! (Not proofread)

⟢ Storm Chaser! Dean Winchester x Meteorologist! Reader (No use of Y/N)

⟢Summary: You have been hired to work as an intern for one of the popular internet storm chasers, little did you know it was not what you expected, especially on your first day.

(2490 Words)

Divider Credits: @strangergraphics, @edensrose

“Alright, we’ve got one up ahead, looks like this one is a small but mighty one.” Sam had been on the computer for a couple of hours now, looking for any sign of a possible Tornado. Dean cracked open a beer and handed one to Dean. Jo had begun ordering new parts for their modified Ford truck. She was a beauty modded with rockets, a surround sound system, and a powerful arching system to dig into the ground. Castiel had begun making the exact map of where the tornado was heading and picking the right estimate of where the rocket should be launched to collect data. Cyclone Ranch was the family business. Dean had begun storm chasing after his father, John, had died trying to protect Sam and Dean from an EMF 5 while they were at the park. Cyclone Ranch had begun to become popular among other amateur storm chasers, and especially college students. Dean had opened up Cyclone Ranch to recent college graduates for paid internships. So Dean had finally gotten one, you. 

Dean was known for driving pretty recklessly around these parts. But the rest of the crew didn’t mind at all. It seemed normal to them.

“Hey, when’s that person coming, the intern or whatever?” Asked Sam while still focusing on the computer, taking a swig of his beer. Dean looked toward his brother, away from the road, “Any minute now, Sammy. Take a look, man, we got a good one.” Dean dragged his hand against the computer and switched the tab to your resume.  Sam took a look at your resume, and he was impressed with the stats you had. A recent graduate with a PHD in Meteorology, good grades, and lots of recommendations from previous jobs and professors. 

You had been nervous but excited. You were a fan of the Cyclone Ranch live streams, you were even one of those fans who had a crush on the oh so handsome Winchester brothers. You had pulled up to a small lot with other tornado chasers. “Excuse me?” You walked up to a man who was leaning against a huge white van with satellites on top of the van. “I’m looking for Cyclone Ranch, I’m an intern,” you smiled. The guy snarked and scoffed. “Cyclone Ranch? Oh yeah, they should be comin’ anytime soon. Serious business, huh?” he laughed. You, however, were pretty confused. “Uh, yeah, I’m looking forward to-” Your words were interrupted by loud music. The sound of Metallica playing through the speakers, you jumped from the sudden hard bass coming from the truck. The other storm chasers gathered around the truck, mainly girls. You took a better look at the truck and saw the famous Cyclone Ranch logo. “Oh god…” You muttered. 

The famous Dean Winchester holding up t-shirts and throwing them to the girls who were screaming and blowing kisses at the brothers, Castiel, hell, even Jo, cause who wouldn’t?

“The brothers are back in town, baby!” he yelled out from the window. When they pulled up, your face dropped. You had thought it was a serious business, but now, looking at their setups and equipment, you weren’t too sure. You walked towards the truck, pushing through the crowd of people trying to get to the front. You held on tight to your notebooks and satchel. You had finally caught up to the front and were face to face with Dean himself.

 “Hi, I'm looking for-” Dean put up his hand in front of your face. “Say no more, babydoll, I’m always happy to sign for a fan.” Dean took your notebook and signed the front cover. Sam came behind his shoulder. “Dean, I don’t think-” Dean took out a box and took a good look at your body before handing you a shirt in your size. “Here, take one, take it as a gift.’ He smirked. 

However, you threw him back the shirt. “I’m not a fan, I’m the intern you hired,” you said seriously. Castiel broke the small tension, “Welcome to the team, I’m Castiel. I work with communications. Sam here is the analyzer, keeps track of the storms.” Castiel then waves at Jo. “That’s Jo, the sane one, and the mechanic of that beauty she's working on.” You looked around, “I thought this was an actual company with actual serious shit,” you asked. 

Dean, however, looked offended, not only had you thrown his shirt back at him, but you ignored his charm, and dissed his company. “Alright, listen here, doll, you either back out or join us. Good luck finding another job out here in the middle of nowhere. What’s it gonna be and make it quick,” He snapped. You eventually agreed to stay and work with Dean on collecting the data. 

“We got one,” Sam shouted. “Let's ride, babydoll, you comin’ or not?” Dean said scoffingly. So this is why the guy you were talking to earlier basically laughed in your face, their company was a joke compared to the others. “Yeah, I'm comin’”

While driving to the sight of a twister, you saw it moving strangely. As you sat in the front seat next to Dean, who had been blasting his sound system, you looked out the window. The skies that had gone from a shiny blue sky had turned almost green. You began growing skeptical, so you turned your head to the computer. The meter had rocked from an orange to a bright red. “Dean, we can’t go into this storm, you're insane!” Jo yelled. “Sweetheart, this is my job, either you jump out and wait this storm or you ride with us.” Dean had always been persistent about his findings. He took Cyclone Ranch seriously and wanted to make it to the big leagues so people like the guys you were talking to would put their money they made into their mouths for them to shut up. The winds were moving a completely different way from what Sam had perceived. “Go the other way,” Sam demanded of Dean. He scoffed, “Alright, you ain’t telling me what to do, dude.” He said. 

“We’re right next to a town,” you said softly as you looked back. “The people in that town have no idea what’s going on if you don’t turn this truck around so we can save those people, don’t even call yourself a storm chaser,” you said. Dean didn’t listen to you. He barely knew you for like 3 hours. Everyone in the truck was telling him to turn around so they wouldn’t go towards the danger. “We do this all the time, you gonna believe a guy you guys knew for half your lives or a fancy college barbie?” The knuckles on his hands grew white from the tension of gripping the wheel. Right when he yelled, something had hit the window. You took a closer look to see ice on the hood. “Hail…” Castiel said in disbelief, “It’s gonna be a big one.” You had enough. You jumped in front of Dean in the driver's seat and pushed the seat back. You sat on his lap and controlled the truck. “Am I good back there to turn?” you asked. Sam held a thumbs up and Yeah. Dean tried to take back control, but you wouldn’t have it. It was like playing footsies with him, but with the wheel of a moving car. You managed to turn the truck around towards the town, but the winds were already growing stronger by the minute. “Guys, alert the town, we don’t have much time,” Jo yelled out before the glass of the rear window had cracked from the string hail. “Some storm chaser you are.” You mumbled to Dean as you took control of the wheel. 

As you reached the town, everyone got down. The townspeople were already alerted when the tornado siren had grown louder. You ran into a small daycare that had a basement inside. You had ordered people who were the closest to you into the basement. “Sammy, take the vendor and bring 'em inside the shops!” Dean yelled out. Jo and Castiel began to bring others into huge buildings without windows and any secure areas. It was only you and Dean in the storm, trying to make sure everyone was ok. Except one. A girl wearing a bright duck coat and bright pink shoes, crying and standing in fear, calling out for her mom. You and Dean immediately ran to her and, with no hesitation, picked her up. “It’s ok, we’re here to help find your mama,” you soothed as much as you could. “Cmon, we need to head to a shelter,” Dean yelled through the strong winds. However, there was nowhere else, every basement was full, and no luck finding the girl's mother. “Dean, a ditch!” you yelled out. Dean jumped in first, and once he did, his hands stretched out to grab the kid, then you. You cradled the girl and put her duck hoodie on her head to protect her from the storm. You put the girl's head in the crook of your neck to protect her face. Dean put his whole body over you, his hand went around your waist and the girl's body as much as he could, while his other hand kept digging into the ground as the twister became stronger. 

The sounds of the little girl crying and the strong winds made Dean groan from the amount of strength he’s using to keep the two alive. He saw the girl's eyes, and it made him think of that day. He was around the girl’s age with his dad, and he made the exact same face she did when he first saw a twister as strong as this. The twister is moving towards them, and Dean laid his head on your shoulder as he kept gripping onto the ground and you. Thousands of random things came flying, wood, glass, even some baseballs from a local game at the park

Eventually, the twister had died down a bit and moved on, but the strong winds were still there. “Is it over?” asked the girl softly. You smiled, “It’s almost done, ok, just stay put, little duck.” You said. You looked at Dean, who was behind you. He looked over to the sky and saw that the clouds were slowly moving away. He got up first and climbed back up. Sam, Cas, and Jo came out of different buildings with people who were still scared to see if the storm had passed or moved away. “We’re good,” Dean said, looking down in the muddy ditch to see you still holding onto the girl. You got up and used your strength to lift the girl up to Dean as he put her back on top. He then took your hand in his rough ones and brought you back up. Both of you were all muddy and dirty, and so was the girl. You looked around the skies before facing Dean, who looked almost distraught. “I’m sorry,” he panted. “I know I’m a joke in this business. I should’ve listened to you guys.” You could only look at him before the girl tugged on Dean’s jacket. He looked down and saw her with a small pout. “Thank you for saving us.” She said softly in her small voice. But he knew now who he was doing this business for. Not for him, not for his dad. But for people like her, for her to be safe. He crouched down softly to her level and buttoned up her last button on her coat. “You’re welcome,” he smiled. 

“Charlotte!” A woman came running from the local shop. “Mommy!” she said, running immediately straight for them. “Oh, thank god you’re safe!” She said, hugging the girl tightly. “You’re not hurt, are you, baby?” The girl shook her head before looking back at you and Dean. “Thank you! Oh, thank you!” The mother said, smiling and crying all at once. “It was no problem, your daughter is very brave.” You smiled, trying to keep everything calm. When the mother and daughter left them alone, Dean placed a hand on your shoulder in reassurance. “You ok? Rough first day,” he softly joked to bring up the mood a bit. You, however, weren’t smiling. “Yeah…just glad everyone is ok,” you said. Dean brought his hand back to himself. 

The gang was together again. However, they began passing around food and water to the townfolk while an ambulance was checking up on all the townspeople to make sure they were ok. “You’re a good guy, Dean,” you said as you were eating your sandwich, still muddy and dirty. “Even for a guy who pastes his face on a shirt,” you said teasingly. Dean smirked as he finished his sandwich. “I guess if you want to, I’d want to keep you in the business, I mean, you're a hell of a gal. And if you managed to take my hands off the wheel, imagine you at your potential.” He said. You tilted your head so he could say what you thought he was saying. “I talked with the rest, they reviewed your resume, and if you want to, of course… stay with us? And if not I’ll send the best damn recommendation you’ve ever seen.” You laughed a bit. You looked forward to seeing the storm chaser you talked to before, the one who laughed at you handing people business cards to buy their property. Then, looking at Castiel and Jo handing people food and extra merch they had in their truck. “I feel like you guys are more fun than those guys,” you said, turning your head towards him. “Why not?” you said. Dean smiled, hoping to fix your rough first meeting. 

“Listen, I don’t do this much, but I’m sorry for the way I treated you before…Can we maybe? Have a fresh start?” he asked. You nodded and smiled. “Of course, but..leave the shirt out.” You said. Dean faked his offended look. “Why?” he asked. You looked away, embarrassed. “Oh my god…you have one already, don’t you?” he smirked. “Shut up,” you said awkwardly. “You are a fan! Hey, you may be my stalker?” he continued to tease while you kept turning your head away. “Shut up before I change my mind.” You said, pushing him playfully. Sam called you guys over to gather around the truck. As you walked,  Dean couldn’t stop looking at you. As you reached Sam, he announced, “There’s a small twister that looks small enough for us to get rid of. We won’t get much data, but it’s something. What do we think?” He asked. Dean looked immediately down at you. Your eyes had already met his as both of you smirked. “Let’s ride, baby.” 

There, your adventures started with Cyclone Ranch, with a wannabe Reed Timmer. But you couldn’t be happier in this moment, chasing storms with meteorologists’ biggest heartthrob.

Taglist @applelovesposts @ladykitana90 @cevansbaby-dove @cleacc

A/N: Hello! sooo I'm back? Sorry, I've been gone for a while, just had to take a small lil break for school and funsies. But glad to be writing whatever I want on my blog. Thank you guys for the support you've shown me, I really appreciate all of you. Anyway, here's a fic you guys didn't ask for, but I'll provide happily :D . As for the contract series, I'm having trouble reading the script and making it sound good and adding more plot, so I'm going through a small writer's block. So we may be going on a little break for that series, but let me know what other characters you want me to do. I'm already working on a Sam fic btw *wink wink*. Hope you guys enjoy this small oneshot.

[ribbonsncherries]

Cyclone Ranch .°˖⋆ 𓃗 .°˖⋆

⟢Warnings: Mentions of tornadoes and twisters, very bad descriptions of weather and climate, Dean being rude asf, mentions of lost child, fluff at the end! (Not proofread)

⟢ Storm Chaser! Dean Winchester x Meteorologist! Reader (No use of Y/N)

⟢Summary: You have been hired to work as an intern for one of the popular internet storm chasers, little did you know it was not what you expected, especially on your first day.

(2490 Words)

Divider Credits: @strangergraphics, @edensrose

“Alright, we’ve got one up ahead, looks like this one is a small but mighty one.” Sam had been on the computer for a couple of hours now, looking for any sign of a possible Tornado. Dean cracked open a beer and handed one to Dean. Jo had begun ordering new parts for their modified Ford truck. She was a beauty modded with rockets, a surround sound system, and a powerful arching system to dig into the ground. Castiel had begun making the exact map of where the tornado was heading and picking the right estimate of where the rocket should be launched to collect data. Cyclone Ranch was the family business. Dean had begun storm chasing after his father, John, had died trying to protect Sam and Dean from an EMF 5 while they were at the park. Cyclone Ranch had begun to become popular among other amateur storm chasers, and especially college students. Dean had opened up Cyclone Ranch to recent college graduates for paid internships. So Dean had finally gotten one, you. 

Dean was known for driving pretty recklessly around these parts. But the rest of the crew didn’t mind at all. It seemed normal to them.

“Hey, when’s that person coming, the intern or whatever?” Asked Sam while still focusing on the computer, taking a swig of his beer. Dean looked toward his brother, away from the road, “Any minute now, Sammy. Take a look, man, we got a good one.” Dean dragged his hand against the computer and switched the tab to your resume.  Sam took a look at your resume, and he was impressed with the stats you had. A recent graduate with a PHD in Meteorology, good grades, and lots of recommendations from previous jobs and professors. 

You had been nervous but excited. You were a fan of the Cyclone Ranch live streams, you were even one of those fans who had a crush on the oh so handsome Winchester brothers. You had pulled up to a small lot with other tornado chasers. “Excuse me?” You walked up to a man who was leaning against a huge white van with satellites on top of the van. “I’m looking for Cyclone Ranch, I’m an intern,” you smiled. The guy snarked and scoffed. “Cyclone Ranch? Oh yeah, they should be comin’ anytime soon. Serious business, huh?” he laughed. You, however, were pretty confused. “Uh, yeah, I’m looking forward to-” Your words were interrupted by loud music. The sound of Metallica playing through the speakers, you jumped from the sudden hard bass coming from the truck. The other storm chasers gathered around the truck, mainly girls. You took a better look at the truck and saw the famous Cyclone Ranch logo. “Oh god…” You muttered. 

The famous Dean Winchester holding up t-shirts and throwing them to the girls who were screaming and blowing kisses at the brothers, Castiel, hell, even Jo, cause who wouldn’t?

“The brothers are back in town, baby!” he yelled out from the window. When they pulled up, your face dropped. You had thought it was a serious business, but now, looking at their setups and equipment, you weren’t too sure. You walked towards the truck, pushing through the crowd of people trying to get to the front. You held on tight to your notebooks and satchel. You had finally caught up to the front and were face to face with Dean himself.

 “Hi, I'm looking for-” Dean put up his hand in front of your face. “Say no more, babydoll, I’m always happy to sign for a fan.” Dean took your notebook and signed the front cover. Sam came behind his shoulder. “Dean, I don’t think-” Dean took out a box and took a good look at your body before handing you a shirt in your size. “Here, take one, take it as a gift.’ He smirked. 

However, you threw him back the shirt. “I’m not a fan, I’m the intern you hired,” you said seriously. Castiel broke the small tension, “Welcome to the team, I’m Castiel. I work with communications. Sam here is the analyzer, keeps track of the storms.” Castiel then waves at Jo. “That’s Jo, the sane one, and the mechanic of that beauty she's working on.” You looked around, “I thought this was an actual company with actual serious shit,” you asked. 

Dean, however, looked offended, not only had you thrown his shirt back at him, but you ignored his charm, and dissed his company. “Alright, listen here, doll, you either back out or join us. Good luck finding another job out here in the middle of nowhere. What’s it gonna be and make it quick,” He snapped. You eventually agreed to stay and work with Dean on collecting the data. 

“We got one,” Sam shouted. “Let's ride, babydoll, you comin’ or not?” Dean said scoffingly. So this is why the guy you were talking to earlier basically laughed in your face, their company was a joke compared to the others. “Yeah, I'm comin’”

While driving to the sight of a twister, you saw it moving strangely. As you sat in the front seat next to Dean, who had been blasting his sound system, you looked out the window. The skies that had gone from a shiny blue sky had turned almost green. You began growing skeptical, so you turned your head to the computer. The meter had rocked from an orange to a bright red. “Dean, we can’t go into this storm, you're insane!” Jo yelled. “Sweetheart, this is my job, either you jump out and wait this storm or you ride with us.” Dean had always been persistent about his findings. He took Cyclone Ranch seriously and wanted to make it to the big leagues so people like the guys you were talking to would put their money they made into their mouths for them to shut up. The winds were moving a completely different way from what Sam had perceived. “Go the other way,” Sam demanded of Dean. He scoffed, “Alright, you ain’t telling me what to do, dude.” He said. 

“We’re right next to a town,” you said softly as you looked back. “The people in that town have no idea what’s going on if you don’t turn this truck around so we can save those people, don’t even call yourself a storm chaser,” you said. Dean didn’t listen to you. He barely knew you for like 3 hours. Everyone in the truck was telling him to turn around so they wouldn’t go towards the danger. “We do this all the time, you gonna believe a guy you guys knew for half your lives or a fancy college barbie?” The knuckles on his hands grew white from the tension of gripping the wheel. Right when he yelled, something had hit the window. You took a closer look to see ice on the hood. “Hail…” Castiel said in disbelief, “It’s gonna be a big one.” You had enough. You jumped in front of Dean in the driver's seat and pushed the seat back. You sat on his lap and controlled the truck. “Am I good back there to turn?” you asked. Sam held a thumbs up and Yeah. Dean tried to take back control, but you wouldn’t have it. It was like playing footsies with him, but with the wheel of a moving car. You managed to turn the truck around towards the town, but the winds were already growing stronger by the minute. “Guys, alert the town, we don’t have much time,” Jo yelled out before the glass of the rear window had cracked from the string hail. “Some storm chaser you are.” You mumbled to Dean as you took control of the wheel. 

As you reached the town, everyone got down. The townspeople were already alerted when the tornado siren had grown louder. You ran into a small daycare that had a basement inside. You had ordered people who were the closest to you into the basement. “Sammy, take the vendor and bring 'em inside the shops!” Dean yelled out. Jo and Castiel began to bring others into huge buildings without windows and any secure areas. It was only you and Dean in the storm, trying to make sure everyone was ok. Except one. A girl wearing a bright duck coat and bright pink shoes, crying and standing in fear, calling out for her mom. You and Dean immediately ran to her and, with no hesitation, picked her up. “It’s ok, we’re here to help find your mama,” you soothed as much as you could. “Cmon, we need to head to a shelter,” Dean yelled through the strong winds. However, there was nowhere else, every basement was full, and no luck finding the girl's mother. “Dean, a ditch!” you yelled out. Dean jumped in first, and once he did, his hands stretched out to grab the kid, then you. You cradled the girl and put her duck hoodie on her head to protect her from the storm. You put the girl's head in the crook of your neck to protect her face. Dean put his whole body over you, his hand went around your waist and the girl's body as much as he could, while his other hand kept digging into the ground as the twister became stronger. 

The sounds of the little girl crying and the strong winds made Dean groan from the amount of strength he’s using to keep the two alive. He saw the girl's eyes, and it made him think of that day. He was around the girl’s age with his dad, and he made the exact same face she did when he first saw a twister as strong as this. The twister is moving towards them, and Dean laid his head on your shoulder as he kept gripping onto the ground and you. Thousands of random things came flying, wood, glass, even some baseballs from a local game at the park

Eventually, the twister had died down a bit and moved on, but the strong winds were still there. “Is it over?” asked the girl softly. You smiled, “It’s almost done, ok, just stay put, little duck.” You said. You looked at Dean, who was behind you. He looked over to the sky and saw that the clouds were slowly moving away. He got up first and climbed back up. Sam, Cas, and Jo came out of different buildings with people who were still scared to see if the storm had passed or moved away. “We’re good,” Dean said, looking down in the muddy ditch to see you still holding onto the girl. You got up and used your strength to lift the girl up to Dean as he put her back on top. He then took your hand in his rough ones and brought you back up. Both of you were all muddy and dirty, and so was the girl. You looked around the skies before facing Dean, who looked almost distraught. “I’m sorry,” he panted. “I know I’m a joke in this business. I should’ve listened to you guys.” You could only look at him before the girl tugged on Dean’s jacket. He looked down and saw her with a small pout. “Thank you for saving us.” She said softly in her small voice. But he knew now who he was doing this business for. Not for him, not for his dad. But for people like her, for her to be safe. He crouched down softly to her level and buttoned up her last button on her coat. “You’re welcome,” he smiled. 

“Charlotte!” A woman came running from the local shop. “Mommy!” she said, running immediately straight for them. “Oh, thank god you’re safe!” She said, hugging the girl tightly. “You’re not hurt, are you, baby?” The girl shook her head before looking back at you and Dean. “Thank you! Oh, thank you!” The mother said, smiling and crying all at once. “It was no problem, your daughter is very brave.” You smiled, trying to keep everything calm. When the mother and daughter left them alone, Dean placed a hand on your shoulder in reassurance. “You ok? Rough first day,” he softly joked to bring up the mood a bit. You, however, weren’t smiling. “Yeah…just glad everyone is ok,” you said. Dean brought his hand back to himself. 

The gang was together again. However, they began passing around food and water to the townfolk while an ambulance was checking up on all the townspeople to make sure they were ok. “You’re a good guy, Dean,” you said as you were eating your sandwich, still muddy and dirty. “Even for a guy who pastes his face on a shirt,” you said teasingly. Dean smirked as he finished his sandwich. “I guess if you want to, I’d want to keep you in the business, I mean, you're a hell of a gal. And if you managed to take my hands off the wheel, imagine you at your potential.” He said. You tilted your head so he could say what you thought he was saying. “I talked with the rest, they reviewed your resume, and if you want to, of course… stay with us? And if not I’ll send the best damn recommendation you’ve ever seen.” You laughed a bit. You looked forward to seeing the storm chaser you talked to before, the one who laughed at you handing people business cards to buy their property. Then, looking at Castiel and Jo handing people food and extra merch they had in their truck. “I feel like you guys are more fun than those guys,” you said, turning your head towards him. “Why not?” you said. Dean smiled, hoping to fix your rough first meeting. 

“Listen, I don’t do this much, but I’m sorry for the way I treated you before…Can we maybe? Have a fresh start?” he asked. You nodded and smiled. “Of course, but..leave the shirt out.” You said. Dean faked his offended look. “Why?” he asked. You looked away, embarrassed. “Oh my god…you have one already, don’t you?” he smirked. “Shut up,” you said awkwardly. “You are a fan! Hey, you may be my stalker?” he continued to tease while you kept turning your head away. “Shut up before I change my mind.” You said, pushing him playfully. Sam called you guys over to gather around the truck. As you walked,  Dean couldn’t stop looking at you. As you reached Sam, he announced, “There’s a small twister that looks small enough for us to get rid of. We won’t get much data, but it’s something. What do we think?” He asked. Dean looked immediately down at you. Your eyes had already met his as both of you smirked. “Let’s ride, baby.” 

There, your adventures started with Cyclone Ranch, with a wannabe Reed Timmer. But you couldn’t be happier in this moment, chasing storms with meteorologists’ biggest heartthrob.

Taglist @applelovesposts @ladykitana90 @cevansbaby-dove @cleacc

A/N: Hello! sooo I'm back? Sorry, I've been gone for a while, just had to take a small lil break for school and funsies. But glad to be writing whatever I want on my blog. Thank you guys for the support you've shown me, I really appreciate all of you. Anyway, here's a fic you guys didn't ask for, but I'll provide happily :D . As for the contract series, I'm having trouble reading the script and making it sound good and adding more plot, so I'm going through a small writer's block. So we may be going on a little break for that series, but let me know what other characters you want me to do. I'm already working on a Sam fic btw *wink wink*. Hope you guys enjoy this small oneshot.

[ribbonsncherries]

my lazy ass after writing one sentence while writing a fic:

[ribbonsncherries]

hey girl I've seen we like each other's work a lot, I was wondering if we could be moots?

Ummmm DUHHHHH I love your work 💕💕

[ribbonsncherries]

I’m late to the party and just watched Twisters I NEED a fanfic with a Twisters AU! ima have to write for myself at this point 😭

[ribbonsncherries]

If yall can donate please do so! If you can’t, repost to spread the word! Kindness and generosity is our best friend!

🌍 A Letter from Gaza: Your Kindness is Keeping Us Going

Hi, my name is Mosab, and I am a survivor from Gaza. I have lost 25 members of my family, and I carry their memory with me every day. Our home is gone, our lives have changed forever.

But thanks to you, we are still holding on. We have now raised $3,300, and I am beyond humbled. Every single dollar has helped us find food, water, and a small sense of stability in a world that has been turned upside down.

Even $5 can change our reality. If you can’t donate, please reblog this post.

Your kindness is not just charity—it is survival. Thank you for standing with us when we needed you the most.

With all my love, Mosab & Family ❤️

[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 5

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.

(3818 Words)

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!

[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 5

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.

(3818 Words)

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!

[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 5

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.

(3818 Words)

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!

[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 5

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.

(3818 Words)

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!

[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 4

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.

(4530 Words)

Divider credits: @dollywons, @anitalenia, @selysie

(y/n) had woken up, She felt something warm next to her only to realize when she adjusted her eyes a sleeping Dean. She relaxed on her respective side worrying if she even touched him he might jolt awake. Her thoughts were winding over the memories from last night, the people were right. He is a sex god as people assumed. She quietly got up from bed and put on his dress shirt to cover everything up, she buttoned up the buttons halfway and rolled up her sleeves. As she began walking out the door the bright light made her squint. She looked down her legs to get her face away from the light, when she looked down she saw many Hickeys on her inner thighs. She didn’t even want to think about that. Her heart began racing the more she saw on her lower chest. She took a deep breath, adjusted her eyes to the bright sun, and walked to the kitchen. (y/n) wasn’t much of a cook but she sure knew how to make a “good breakfast” as Jess calls it. 

It took a while for (y/n) to look for the proper things she needed to make the food, like pans, utensils, and all that junk. When she opened the fridge she saw many ingredients for cooking. She smirked knowing she had everything she needed. When gathering all the items she found a radio so she didn’t hesitate to turn it on and lower the volume so Dean wouldn't hear the ruckus going on down in the kitchen. The only thing (y/n) knew from this house was that she was poor. He had so many mechanical uses in the kitchen it felt like deciphering a code. It couldn’t be this complicated. She took her phone and looked up the certain uses for the stove. This stove to her looked like the fucking space shuttle for all she knew. Then she began cooking, cutting up some chilies for spice, and adding some seasonings for that nice flavor. She turned on the radio and began tapping her feet to the beat and swaying her hips softly to the rhythm while humming. 

Dean heard some clattering in the kitchen and the smell of fresh breakfast around the room. He looked to next him and saw the empty side, he silently frowned. Why did he have this sudden urge last night that he was almost looking forward to waking up next to her? He put on some sweatpants and a random shirt he had lying on the floor. He came out of the room and heard some slight clattering and music. “Whole Lotta Love” By Led Zepplin was playing softly around the kitchen, he saw her putting the vegetables in a glass bowl while she was shaking her body softly. Dean smirked and sat down at the kitchen island with his arms resting on the table. She turned around and jumped. “You’re awake?” she asked still a little shocked he suddenly showed up. He smirked and scoffed, “You seem very energetic this mornin’ sweetheart.” He said. “Sorry to intrude, just wanted to make you a nice breakfast.” she smiled hoping he would be okay with it. He nodded while looking up and down her body only wearing his dress shirt with nothing underneath. 

“It’s alright, I don’t really make a lot for myself anyways just diners, especially the ones that look like are hanging on by a thread and looks like it hasn’t been certified by the FDA are the best in town.” He smiled. “So what are you makin’?” 

(y/n) smiled, “Well I’ve just finished making omelets, sausage, and bacon. What did you want?” she asked holding up an empty plate with one hand and a utensil in the other. Dean was almost starstruck, no woman he’s ever had this contract with has ever really done this for him. He smiled with his green eyes and told her he wanted everything. She immediately took note and began serving his plate, Once she put it down in front of him she poured some orange juice in a cup and placed that next to him before she served for herself. As they sat side by side together they never spoke about last night. As amazing as it was she couldn’t say anything. What was she even to say after he basically signed her to be his personal submissive and took her virginity? Thank you?  “How is it?” she asked him while chewing on her bacon. 

“This is delicious,” he said with a full mouth of eggs. She laughed at the scene and used her napkin to wipe some egg off the side of his mouth, “You know for a multi-billionaire you are pretty messy.” she said giggling. When Dean swallowed the rest of his food he smiled. When breakfast was finished and (y/n) was gathering up the dishes Dean stopped her. He took her hand and led her to the bathroom “Let’s get you cleaned up.”. Dean took off his shirt and sweatpants, (y/n) immediately took the signal slowly unbuttoned the shirt she had on, and stepped into the tub of warm water. Dean stepped in behind her as took a clean sponge and began cleaning her back slowly. His hand came upon her waist. Hi shand went lower and lower till his fingers were at her core. She gasped from the sudden sensation, Dean put the sponge down and leaned her against his chest. Her head laid back on his shoulder as his fingers began going in and out of her pussy. Her hand went to his wrist but he immediately grabbed it and pinned her hand behind her. “Oh fuck, don’t stop, don’t stop. She moaned quietly. He went faster and curled up his fingers to hit her G-spot. Her eyes rolled to the back of her head as he released his fingers before she was about to cum. He got up from the bathtub and gave her a towel before getting his own. He led her to his bedroom and told her to wait. He went to his closet and opened a drawer. This drawer had cubicles that stored his ties, one particular one struck out. It was a nice grey tie with a few dark blue stripes coming down the tie. He came back to her only a towel wrapped around her. “Do you trust me, Princess?” he said to her roughly. 

“Yes,” she breathed out. He took the towel off her and laid her down on the bed, “Give me your wrists.” he demanded. She did what she was told and tied his tie around her wrists making them bound. He got on top of her and placed her hands above her. He began nipping at her ear down to her collarbone while his other hand was groping her tits. His open mouth kisses went down to her breast and he started sucking her nipple. Her gasps from the sudden pleasure echoed in the room. She began twitching her hands wanting to grab something, his hair or his back. “Be a good girl and stay still,” he whispered in her ear. “Okay.” she moaned out. 

“Dean!” yelled out “Dean get out of bed I know you’re still asleep!” Yelled out women from the distance. (y/n) was confused, “who’s that?” she asked panting as Dean grabbed her wrists and began untying the bound. “Ellen, a family friend,” he said. She began giggling at the situation, “I’m here on your bed naked.” she whispered. Dean smirked at her while he softly threw his shirt and her jeans from last night. “Get dressed,” he said before kissing her forehead. (y/n) quickly threw on a bra and buttoned up the shirt like she did this morning. As she put on her jeans the voices were getting louder. “

Ellen was waiting at the entrance of the penthouse looking for Dean, she knew damn well he was probably sleeping, especially at this hour. “Ah, good morning sleeping beauty.” She joked. Dean smiled and hugged her, “Hey Ellen, what brings you by?” 

“I can’t stop by? Your father’s brains soaked into that pretty head of yours or what?” she said. (y/n) walked out of the hallway and into the room, “Hi.” she smiled politely. Ellen looked almost shocked to see a girl in Dean’s house. “Oh my god…” Back when Dean was a teenager he would hook up with every girl in town whenever he moved schools, but when he became serious about his business and had a reputation to uphold he stopped and hasn’t introduced the Winchester family to any women in years. Not since… 

“I didn’t know you were seein' someone, Dean you dog. And you didn’t say she was pretty.” (y/n)’s smile widened, “Oh thank you so are you.” She said shaking her hand. “Well I really just stopped by 'cause I was in the neighborhood,” Ellen began walking out while Dean followed her. “Well, Sam just got a promotion and we’ll be havin’ a celebratory dinner at your dad’s house. You’re more than welcome to join us.” Ellen said to (y/n). (y/n)’s phone rang in the middle of the conversation, “Go ahead take it, Ellen I’ll walk ya out.” he said gesturing to her phone. (y/n) nodded and mouthed ‘thank you’ before walking into the hallway and answering the phone. “Hello,” she answered. 

“So, you stayed the night, how’d it go?” Jessica responded smugly. (y/n) laughed, “I can’t talk about it right now Jess,” She said, “I’ll call you back ok?” she said before hanging up. As she walked down the hallway, she walked into the room that was ‘hers’ like Dean had mentioned last night. As she sat down on the vanity, took her thumb, and licked her finger, she then began taking away the mascara that was under her eye and began fixing her hair which was still a bit damp from the bath and activities earlier. She saw Dean in the reflection of the mirror. (y/n) kept a straight face as he came up behind her. “Tell me the truth…how many women have been in this room?” she said looking at herself in the mirror. 

“15,” He said, “I can understand if you want out-” 

“I don’t want out.” she clarified. “It’s just, not looking forward to getting smacked and whipped in your red room of pain,” she said quietly looking at him through her reflection. “The room is more about pleasure…I promise. Try to keep an open mind sweetheart.” He took her chin and turned her away from the mirror to face him, “If you agree, then I will be fully devoted to you…no one else. This is what I want And I want it with you.” he said. (y/n) got up from the vanity and began pacing the room from thinking, “But what about sleeping together, we slept in the same bed last night what makes other times so different?” she asked, Dean took a small breath, “Try not to get so beat up with the sleeping arrangements, if you do this you’re gonna want your own room.” He said. (y/n) looked down and scoffed, “Why? Cause I’ll just be used for sex?” she said. Dean pinched between his eyebrows in frustration, “Let’s not talk here, let’s discuss downstairs.” he said taking her arm which she immediately snatched back. “I would like to use the rest of my freedom thank you,” she said before walking away. “Actually no, I want to go home. Take me home.” she smiled before getting her jacket and walking out. Dean secretly smirked. She was feisty, she was not all the way submissive to him. He liked the game she was playing and wanted to play more. 

A couple minutes later Dean took her to the garage. It looked like a parking garage you would find in those shopping malls. It was lined up with beautiful Classic Cars, including the Chevy Impala he drove her in. “All these are yours?” she said in disbelief. “Yes,” he responded. He took her to a 67, Mercury Monterey and opened the door for her, she got in the car and Dean began making the long drive back to (y/n)’s apartment. After a few hours (y/n) was asleep peacefully, Dean looked to his side and found her leaning on the window. So he decided to tell her someplace special. He took her to a small pit stop, He took some hair away from her face and she began moving and opened her eyes. “C’mon, let's go for a walk,” he said. (y/n) stretched out her arms and legs and got out of the car. As they began walking through the small trail she smiled, “Is this the place where you’re gonna kill me or something?” she joked. He didn’t say anything so her smile went down. After a few minutes of quietness she spoke up, “Why did you decide to do this anyways?” she asked. 

Dean became tense, “My father was always controlling of my brother and me. When my mom died he treated us like soldiers when I was 6 and it never stopped, all I wanted for once was to tell him what to do, tell people to do my bidding like he did, He was my father, and I looked up to him. So…apple doesn’t fall far from the tree. No one, not even Sam knows about this part about me” (y/n) was a bit shocked yet afraid. “So he introduced to be a leader? Mr. Sergeant.” she half-joked. Dean chuckled, “I'll tell him you said that.” he said. They stopped walking when they found a small river and a bench. (y/n) sat down on the bench and looked out the view. Dean sat down next to her. “He still sometimes treats me like a mini him, but I’m sure he did it only to protect me and my brother. Listen (y/n), I know this plan is very intimidating I understand.” 

(y/n) looked at him, “I’ve never asked Benny to take anyone in the Helicopter, never had sex in my own bed, and never slept next to anyone…but you.” She looked at him and smiled softly. “Well isn’t that comforting.” she sarcassed. Dean pushed her strands of hair back behind her ear and kissed her lips softly. When they broke apart her eyes were still closed and opened them up slowly for Dean to look at her and kiss her head. He took her hand and led her back on the trail and into the car to take her home. 

An hour later they finally arrived, Dean went to her side, opened the glove box, and took out a yellow file slip filled with a packet. “Here is the contract, read it carefully. E-mail me if you have any questions.” He said. “Dean I already told you my computer is acting all weird.” 

“Just consider it ok. I genuinely hope you say yes,” he said. (y/n) nodded and got out of the car.  “Thanks for everything,” she said. “Later’s darlin’” (y/n) smiled whenever he mimicked it brother. When she opened the door to her apartment. “Alright, and you are all set.” a male voice echoed the apartment. (y/n) immediately walked into the living room and saw a man in a polo shirt on her laptop, “Your roommate let me in.” he smiled 

“I just figured you forgot to tell me someone was coming to fix up your computer, do I look okay?” Jess said. “Wait Jess hold on, I’m sorry I think you may have the wrong apartment,” she said. The man looked into his clipboard “(y/n) (l/n)?” (y/n) looked a little shocked yet confused. “Sign here please,” he asked. She took the pen and signed the paper. “Thank you enjoy,” he said walking out the door, 

“So, another gift. Whatever happened to flowers, teddy bears, and chocolates?” Jessica laughed. “Tell me, I’m dying to hear about last night. And this time let's speed this up because Sam is taking me to dinner in 10 minutes and then we’re seeing a movie” she smiled. “Oh I almost forgot, James called you like three times yesterday and one time this morning.” (y/n) let out a breath.” Hey, you got a package or something?” she asked looking at the yellow folder in her hands (y/n) panicked but kept it smooth. “Oh no, Castiel wanted me to go over a few articles before we publish them so he sent me a sample for this month’s issue,” she said. Jess had a worried look on her face, “That seems like a lot. Want me to help you?” she asked. (y/n) shook her head. “Oh no, no, it’s ok I got it.”Jess smiled, “Well anyways here’s yesterday's mail.” she said gesturing to the small pile of envelopes for (y/n). (y/n) began going through them while Jessica just smirked at her. (y/n) looked up and laughed, “What? Why are you looking at me like that you weirdo.” she said. “I’m going to ignore that insult. But you look different, in a good way,” she said genuinely. The girls turned their heads to the window when they heard a car horn. Jessica went to the window and saw Sam waiting downstairs for her. She smiled and gave him a small air kiss. She immediately got her purse and ran to the door. “I’ll see you later (y/n), I might stay late so don’t hold up,” she said before closing the door. (y/n) saw her laptop on the table and went to it. It was fixed and looked almost brand new. Until she found out it was new, the box for it was underneath her chair. A ping from the laptop went through. It was from Dean. 

Thank you for a very interesting weekend, This laptop is yours and yours only. I’d like you to use it for research. 

 -Dean

(y/n) bit the inside of her cheek trying to think, she began typing back. 

So this is how it’s going to work out? You order me around?” 

After a few minutes, he responded 

Yes, and there’s more, you’ll like it. 

(y/n) smiled to herself. She looked to her side and saw the folder. She pushed the laptop away and opened it. It was a small packet which was the official contract. As she was reading it she got undressed and onto her bed. 

The following are the terms of a binding contract between the dominant and the Submissive. The fundamental purpose of this contract is to allow the submissive to explore her sensuality and her limits safely. The dominant and the submissive agree and acknowledge that all that occurs under the terms of this contract will be consensual, confidential, and subject to the agreed limits and safety procedures set out in this contract. The submissive will agree to any sexual activity deemed fit and pleasurable by the dominant excepting those hard activities outlined in Hard Limits. The submissive agrees to procure oral contraception from a physician of the dominants’s choosing. The submissive will not enter into sexual relations with anyone other than the dominant. The submissive will eat regularly to maintain her health and well-being. The submissive will not excessively drink, smoke, or take any recreational drugs. The submissive shall always conduct herself in a respectful manner to the dominant and she’ll address him only as “sir” or “Mr. Winchester.” or such other title as the dominant may direct. The submissive may not touch the dominant without his express permission to do so. The safeword “yellow” will be used to bring to the attention of the dominant that the submissive is close to her limit. When the safeword “red” is spoken, the dominant’s action will cease completely and immediately 

Does the submissive consent to being restrained, with hands bound in front?

Does the submissive consent to being blindfolded? 

Does the submissive consent to being gagged?

(y/n) put the packet away in the folder, she took a deep breath and decided she would think about it. A few days later she and Jess were cleaning up and packaging boxes in their offices to move to the floor up. “So have you been speaking to your little friend,” Jessica asked. (y/n) smiled, yes I have, it’s been casual mostly.” Jessica smiled, “Well I'm going to the cafe to get us a small break coffee.” (y/n) nodded and took out her phone to text Dean. 

Dean was with his brother and John at a shooting range. He felt the vibrations in his pocket and saw the message, 

“Currently busy packing for that new office. Missing that tie.” Dean smirked and liked the message. But there were no other messages for (y/n) accepting the contract. “Dean let's go!” John ordered. He put his phone away and pulled out his gun to shoot some rounds. 

After a few more days, Dean was in a business meeting and saw no other messages from (y/n). Later that night (y/n) was in bed watching a movie while Jess was out with Sam. 

“I’m not getting any younger. Have you read the contract yet?” (y/n) liked that he was impatient, and thought she would give him a taste of his own medicine. Although she was pleased she wanted to search up more of the submissive stuff. So she looked it up online and saw the many examples. She immediately blushed and closed the laptop.

The next day at work she got a new email. 

“Growing impatient. Have you thought about it?” (y/n) smiled. 

“Yes. It was nice knowing you,” she responded in a teasing manner. When Dean saw the message his jaw clenched.

When (y/n) went home Jessica was gone. She and Sam have been going on so many dates she basically lives with him. (y/n) decided to do a little spring cleaning and clean her room. She was humming a song while she was bringing in a basket full of laundry. Dean came in with a bottle of his own wine brand and two glasses, wearing his regular getup of flannel and jeans But when she turned around she gasped out in fear putting her hand on her chest, “God Dean you scare me. H-how did you even get in here?” she smiled. 

Dean had on an angry look, “It’s been knowing me?” He said in a low voice clearly angry. He put down the cups took her wrists and pulled her close to him. His hands went to her hair and down to her back. “Let me just remind you how nice it was princess,” he said slowly.

He pushed her onto her bed and climbed on top of her. He pulled out the same grey tie. “This is what you wanted, I’ll give you what you want,” he growled. (y/n) put her wrists out for him and tied the tie to her wrists and onto her headboard. He began getting off her and took off her leggings and panties in one go. “Don’t even make a sound,” he said. She looked at him and nodded. He climbed back on her and lifted her shirt up to her face to cover her eyes. He began massaging her tits and kissing her collarbone. He got off her and took off his shirt and pants. He took some wine and drank some before getting back on top of her. He began kissing her roughly before grabbing a piece of ice from an empty wine glass and holding it in his rough hands before putting it in his mouth. He dragged the cold ice from her collarbone to the nipples of her tits. She gasped at the sudden sensation trying to keep quiet like he told her to. He continued dragging it down to her lower stomach before stopping. “Is this nice?” he said. 

Before (y/n) could answer he flipped her like she was nothing, and smacked her ass hard before grabbing her hips and lifting her legs making her arch. He grabbed a condom and ripped it open with his teeth and put it on himself. His rough hands smoothed over the skin of her ass before he inserted his dick through her glistening wet folds. He began going rough, his thrusts were like he promised, it was quick. She moaned out loud but she covered her mouth with the pillow underneath her. Dean fanned out his hand and placed it on her back to push her more into the mattress which made her arch even more from pleasure. “‘M fuck, go harder.” she pleaded. Dean smirked giving her what she wanted, It was almost primal the way he fucked her. The sounds of skin slapping against each other echoed echoing her small bedroom

"fuck, sweetheart," he rasps, voice thick. Her legs were shaking unable to hold onto herself much longer. He was relentless at this pace she begged for. She couldn’t say anything anymore except for broken whimpers and half moans she could barely let out. Dean pulled out, took off the condom, and cummed on her back and her ass. He let out a groan as he saw the ropes of cum land on her lower back. She let out a moan once more as Dean cleaned her up. He flipped her on her back and untied her. 

A few hours later Dean was in her bed at night, their legs were entangled together as his hand was on his chest. They just were looking at each other not making any small talk. It was a comfortable silence. “That was nice.” she smiled. Dean could only smirk and look at the features on her face. “I don’t know what you’re doing to me,” he said softly. (y/n) put her hand on his cheek and ran her fingers through his messy hair. Dean put his hand on her wrists and put her hand down. She looked down for a bit. “Sorry,” she whispered. She looked at his chest, it was sweaty from a few minutes ago, besides the flashy tattoo on his peck she saw scars on his body, they looked like burn marks and scratches. “Are you ok?” she asked touching his chest in worry. Before she could even put her full-on hand on him he stopped her. She gasped at the sudden movement. “I’m sorry, is it breaking the rules?” she asked. Dean looked at her softly, “Have you made up your mind yet.” he asked. 

“I-I don’t know yet” he didn’t let her finish, he got up and took her legs off him before getting dressed. “You’re not staying?” she asked covering herself up. “I told you I don’t sleep with anyone.” He said. “I’ll negotiate that.” She responded. Dean smiled and kissed her cheek before walking out the door. When she heard the door closed she immediately sighed and fell back on her bed. She had a plan.

Taglist: @applelovesposts @ladykitana90 @cevansbaby-dove

A/N: First of all, my bad for keeping this chapter hostage. I promise I'm writing it's just lots of stuff going on right now so I've just been putting this off. Forgive me lol. Anyways, yay new chapter, so fun. Hope you guys enjoy this one, and once the first book is finished I will be posting a master list of all my stories so you guys have easy access to find them. bare with me yall. Hope you guys enjoy this chapter let me know if you like it! :)

[ribbonsncherries]

Hi everyone! Sorry for the small delay! Hopefully yall can forgive me😛 but I promise a new chapter should be out at least by the end of tomorrow. And if not plz bombard my comments and request box. Thank you for your patience <3

[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 3

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.

(4500 words)

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.” 

“I’m a 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!

[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!

[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!