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#dean winchester x reader – @smol-and-grumpy on Tumblr
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I'm too old for this shit

@smol-and-grumpy / smol-and-grumpy.tumblr.com

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Leather & Lace - Ch 09

Pairing: Dean Winchester x Reader

Summary: Dean Winchester, owner, and editor-in-chief of Craze magazine is an enigma, even to his own employees. There are only a selected few from his industry who have had the luck of meeting him. Of course, being mysterious brings rumors. Ones, such as drinking blood, because he’s a vampire, or, that he went vegan because he believes it’s the key to everlasting life. When Y/N joins the company, however, the latest story circulating is that he’s living somewhere on a private island with his much younger boy toy, and five pet tigers. Crazy, right? Still, she believes it all — up until she meets him, because, in person, Dean Winchester is the bane of her existence.

Warnings: welp, we can not resist, can we

Word Count: 2,213

Beta’d by the amazing @deanwanddamons​ <3

This series is already complete on Patreon

She blinks, partly appalled, but mostly aroused.

Dean doesn’t say a word. He sits there patiently, watching her debating with herself. And she knows she could report it, she could get out of this room right now and send in a complaint to HR, but some invisible force is holding her back. Finally, after an inner fight, she takes off her heels and pushes her skirt up before she drops to her knees, which elicits a chuckle from Dean’s stupidly plum and kissable lips.

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Redlight - Chapter Five

Pairing: Dean Winchester x Hooker!Reader

Summary: Dean Winchester is a rich, recently divorced entrepreneur who visits Los Angeles for business. While he was out with acquaintances one night and was waiting on a limousine to get back to his hotel, he witnessed a woman in need, and rushed in to help, only to learn that the woman was a prostitute. Dean should have left, after he made sure she was okay, but there was something about her that wouldn’t let him walk away.

Chapter Warnings: oh no, feelings? 

WC: 1835

Beta’d by the amazing @winchest09​​

Read weeks ahead on Patreon

Dean comes out of one of the quickest steaming showers of his life and picks up his soiled boxer briefs off the floor, holding it up to inspect them. It’s ruined from their mixed cum. His is on the inside, hers on the outside. The fabric is drenched, and it gets his dick to twitch once more knowing how wet she got for him. He tosses it into the bin by the sink, there’s really no need to wash it, and he’d rather spare the hotel’s laundry person from having to witness the evidence of their dry humping.

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Leather & Lace - Ch 08

Pairing: Dean Winchester x Reader

Summary: Dean Winchester, owner, and editor-in-chief of Craze magazine is an enigma, even to his own employees. There are only a selected few from his industry who have had the luck of meeting him. Of course, being mysterious brings rumors. Ones, such as drinking blood, because he’s a vampire, or, that he went vegan because he believes it’s the key to everlasting life. When Y/N joins the company, however, the latest story circulating is that he’s living somewhere on a private island with his much younger boy toy, and five pet tigers. Crazy, right? Still, she believes it all — up until she meets him, because, in person, Dean Winchester is the bane of her existence.

Warnings: Uh-oh... 

Word Count: 2,096

Beta’d by the amazing @deanwanddamons​ <3

This series is already complete on Patreon

Y/N ended up avoiding leaving her desk for the remainder of the day — and the subsequent days that followed. Dean never showed up either. In fact, on the day she walked out on him, he didn’t leave his office at all.

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Redlight - Chapter Four

Pairing: Dean Winchester x Hooker!Reader

Summary: Dean Winchester is a rich, recently divorced entrepreneur who visits Los Angeles for business. While he was out with acquaintances one night and was waiting on a limousine to get back to his hotel, he witnessed a woman in need, and rushed in to help, only to learn that the woman was a prostitute. Dean should have left, after he made sure she was okay, but there was something about her that wouldn’t let him walk away.

Chapter Warnings: Still just pretty tame...

WC: 3247

Beta’d by the amazing @winchest09​​

Read weeks ahead on Patreon

With a trembling hand, Y/N reaches out for the basket, hoping that she’s a convincing enough actor at trying to hide her excitement at the prospect of taking a bath.

She can’t really help it. It has been a while since she has taken one, back at a time when her world was still innocent and carefree. A world where she resided in the safe home of her aunt and uncle, and where she fell asleep to bedtime stories made up of pretty princesses who got rescued by brave knights on white horses, and end up falling in love and having their own happily ever after.

Of course, the world in her untroubled little bubble didn’t last long.

All good things never do.

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Leather & Lace - Ch 07

Pairing: Dean Winchester x Reader

Summary: Dean Winchester, owner, and editor-in-chief of Craze magazine is an enigma, even to his own employees. There are only a selected few from his industry who have had the luck of meeting him. Of course, being mysterious brings rumors. Ones such as drinking blood because he’s a vampire, or, that he went vegan because he believes it’s the key to everlasting life. When Y/N joins the company, however, the latest story circulating is that he’s living somewhere on a private island with his much younger boy toy, and five pet tigers. Crazy, right? Still, she believes it all — up until she meets him, because, in person, Dean Winchester is the bane of her existence.

Warnings: Dun dun duuuuun

Word Count: 2,551

A/N: I apologize that it took me so long to update! Life has got me by my big metaphorical balls :(

Beta’d by the amazing @deanwanddamons​ <3

This series is already complete on Patreon 

Y/N’s heart rate is at its peak as soon as she stands in front of Dean’s closed office door.

She’s not entirely sure if it’s because she’s turned on or because she’s angry. Quickly, she decides that she’s both. While the anger is dominating her every pore, she can’t really deny that her panties are literally soaked.

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Redlight - Chapter Three

Pairing: Dean Winchester x Hooker!Reader

Summary: Dean Winchester is a rich, recently divorced entrepreneur who visits Los Angeles for business. While he was out with acquaintances one night and was waiting on a limousine to get back to his hotel, he witnessed a woman in need, and rushed in to help, only to learn that the woman was a prostitute. Dean should have left after he made sure she was okay, but there was something about her that wouldn’t let him walk away.

Chapter Warnings: There’s zero warning but it’s good, I promise

WC: 2735

Beta’d by the amazing @winchest09

Read ahead on Patreon

Dean finds himself sitting across from Scarlet as he gets a full view of how she practically inhales her burger and fries. He’s still partial about her dunking them into her milkshake, though, but he tries not to show her how much it disgusts him.

He continues to sip on his glass of whiskey while she talks with her mouth full of food. It’s actually quite comforting to know that even though she has this whole other persona when she’s Scarlet, she doesn’t mind showing him the real her when she gracelessly eats her meal. He’s always been so weak for women with a big appetite; it’s probably a weird kink he’s unable to shake. Dean is still curious, and would really like to know who she really is, though.

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Leather & Lace - Chapter 06

Pairing: Dean Winchester x Reader

Summary: Dean Winchester, owner, and editor-in-chief of Craze magazine is an enigma, even to his own employees. There are only a selected few from his industry who have had the luck of meeting him. Of course, being mysterious brings rumors. Ones such as drinking blood because he’s a vampire, or, that he went vegan because he believes it’s the key to everlasting life. When Y/N joins the company, however, the latest story circulating is that he’s living somewhere on a private island with his much younger boy toy, and five pet tigers. Crazy, right? Still, she believes it all — up until she meets him, because, in person, Dean Winchester is the bane of her existence.

Warnings: They’re still at it

Word Count: 2,517

Beta’d by the amazing @deanwanddamons​ <3

I’m 11 chapters ahead on Patreon in case you can’t wait :)

When her alarm blares, Y/N wakes up feeling like death. It was close to 2.30 AM when she finally arrived home last night and now it’s morning again and she didn’t get nearly enough sleep. As soon as she stepped through her apartment door, she dropped all her things and slipped out of her dress — which was sent to her by fucking Dean Smith. The knowledge makes her nauseous. She can’t stand that fucking dude, seriously.

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Redlight - Chapter Two

Pairing: Dean Winchester x Hooker!Reader

Summary: Dean Winchester is a rich, recently divorced entrepreneur who visits Los Angeles for business. While he was out with acquaintances one night and was waiting on a limousine to get back to his hotel, he witnessed a woman in need, and rushed in to help, only to learn that the woman was a prostitute. Dean should have left after he made sure she was okay, but there was something about her that wouldn’t let him walk away.

Chapter Warnings: And so it starts.... 

WC: 2655

Beta’d by the amazing @winchest09

Read ahead on Patreon

Dean reclines in his seat in the back of the limousine as Scarlet carefully watches the streetlights as they are driving along the Boulevard. She’s paying attention to the street signs, and he finds that he likes that she’s wary. It probably saved her from trouble in the past with her being so aware of where people take her. He also finds that he doesn’t like to think about that, doesn’t like to think about her work and what she’s done up until they met.

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Leather & Lace - Chapter 05

Pairing: Dean Winchester x Reader

Summary: Dean Winchester, owner, and editor-in-chief of Craze magazine is an enigma, even to his own employees. There are only a selected few from his industry who have had the luck of meeting him. Of course, being mysterious brings rumors. Ones such as drinking blood because he’s a vampire, or, that he went vegan because he believes it’s the key to everlasting life. When Y/N joins the company, however, the latest story circulating is that he’s living somewhere on a private island with his much younger boy toy, and five pet tigers. Crazy, right? Still, she believes it all — up until she meets him, because, in person, Dean Winchester is the bane of her existence.

Warnings: Uh-oh... Y/N’s walls are crumbling all around her.

Word Count: 2,082

Beta’d by the amazing @deanwanddamons​ <3

I’m 11 chapters ahead on Patreon in case you can’t wait :)

Fuck, fuck — fuck!

Y/N fucking missed the deadline!

Her heart is pounding while the blood drains from her head, which is not really helping her to get rid of the residue of sleep that’s still very much present.

God, she feels like crying too, on top of everything.

She fell asleep.

Right here at her desk while she was drafting up the article she was supposed to send to Dean almost three and a half hours ago!

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Redlight - Chapter One

Pairing: Dean Winchester x Hooker!Reader

Summary: Dean Winchester is a rich, recently divorced entrepreneur who visits Los Angeles for business. While he was out with acquaintances one night and was waiting on a limousine to get back to his hotel, he witnessed a woman in need, and rushed in to help, only to learn that the woman was a prostitute. Dean should have left after he made sure she was okay, but there was something about her that wouldn’t let him walk away.

Chapter Warnings: There’s assault and a tad of violence

WC: 2672

A/N: Here we goooooo! Hope you like the first chapter!

Beta’d by the amazing @winchest09

Read ahead on Patreon

“I’ll see you later!” Ruby, her roommate, calls out while the heels are clicking on the wood flooring.

“Yeah, I’ll see you later, babe!” Y/N replies before she hears the door of their little two-bedroom apartment slam shut, causing her to flinch.

She’s running late to her second job tonight because Missouri was late to relieve her of her shift at the diner, causing Y/N to have to work an hour longer. It was okay, though, because she was walking away from the diner with $43 more in her purse, including tips. But it means that she was running behind on getting ready to walk the streets with Ruby, that’s why her friend already left to get a head start.

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Leather & Lace - Chapter 04

Pairing: Dean Winchester x Reader

Summary: Dean Winchester, owner, and editor-in-chief of Craze magazine is an enigma, even to his own employees. There are only a selected few from his industry who have had the luck of meeting him. Of course, being mysterious brings rumors. Ones such as drinking blood because he’s a vampire, or, that he went vegan because he believes it’s the key to everlasting life. When Y/N joins the company, however, the latest story circulating is that he’s living somewhere on a private island with his much younger boy toy, and five pet tigers. Crazy, right? Still, she believes it all — up until she meets him, because, in person, Dean Winchester is the bane of her existence.

Warnings: Dun dun duuuuun

Word Count: 2,133

Beta’d by the amazing @deanwanddamons​​ <3

I’m 11 chapters ahead on Patreon in case you can’t wait :)

After Dean had stormed out of the break room seemingly angry with his coffee, which he left forgotten on the counter by the sink, Y/N did not see him again that day. She tried not to think much of it, though, and tried not to think about that infuriating man who somehow managed to get under her skin by merely existing.

Finishing her sweets, she continued to work as well as she could, but when she thought she had her thoughts under control, she found that it was almost impossible because no matter how much she tried to avoid thinking about him, she clearly couldn’t completely let it go. Especially not the things he said. How dare he. Eat properly? What the hell is wrong with Reese’s Cups? And what the fuck is wrong with having candy for food? He isn’t her fucking dad!

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Redlight Masterlist

Pairing: Dean Winchester x Hooker!Reader

Summary: Dean Winchester is a rich, recently divorced entrepreneur who visits Los Angeles for business. While he was out with acquaintances one night and was waiting on a limousine to get back to his hotel, he witnessed a woman in need, and rushed in to help, only to learn that the woman was a prostitute. Dean should have left after he made sure she was okay, but there was something about her that wouldn’t let him walk away.

Warnings: Slow build, slow burn (kinda), angst, smut, fluff... basically my own version of Pretty Woman AU 

You can read ahead on Patreon.

Send me an ask if you want to be tagged <3

Chapter Four ... Chapter Five ... Chapter Six

Chapter Seven ... Chapter Eight ... Chapter Nine

Chapter Ten ... Chapter Eleven ... Chapter Twelve

Chapter Thirteen ... Chapter Fourteen ... Chapter Fifteen

tbc

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Afterglow - Epilogue

af·ter·glow | \ ˈaf-tər-ˌglō
a pleasant effect or feeling that lingers after something is done, experienced, or achieved

Pairing: Dean Winchester x Reader

Summary: Running away from her life, Y/N ends up on the doorstep of her boyfriend’s apartment. In this story of heartbreak, survival, friendship, and love; she gets her first taste of the real L.A. and not the city she had often dreamed about. Her first hurdle? Dean Winchester; the grumpy neighbor who becomes more than just a pain in her ass. Yet, as things start to spiral, she soon realizes that the green-eyed resident from next door is a better person than she’s given him credit for.

Chapter Warnings: A whole lotta fluff

WC: 1,838

Series Beta’d by the amazing @winchest09​​​​​​ <3

Support me on Patreon

If you like what I’m writing, please consider leaving me a tip to keep me energized.

Dean’s nervous. Like, really fucking nervous. His hands are clammy and his heart is beating out of his chest. He can even feel sweat beading on his hairline, and he hopes it won’t run down his face because that would probably look very bad on the red carpet.

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Leather & Lace - Chapter 03

Pairing: Dean Winchester x Reader

Summary: Dean Winchester, owner, and editor-in-chief of Craze magazine is an enigma, even to his own employees. There are only a selected few from his industry who have had the luck of meeting him. Of course, being mysterious brings rumors. Ones such as drinking blood because he’s a vampire, or, that he went vegan because he believes it’s the key to everlasting life. When Y/N joins the company, however, the latest story circulating is that he’s living somewhere on a private island with his much younger boy toy, and five pet tigers. Crazy, right? Still, she believes it all — up until she meets him, because, in person, Dean Winchester is the bane of her existence.

Warnings: We’re continuing with the awkward/sexual tension I guess. Because that’s just how I am as a writer.

Word Count: 2,360

Beta’d by the amazing @deanwanddamons​ <3

I’m 11 chapters ahead on Patreon in case you can’t wait :)

Y/N gets woken up earlier than usual in the morning and lets out an ear-deafening growl when her alarm blares. With an automatic swipe of her hand, she shuts off the offending device with a low grunt.

Getting up early is for a good cause, she has to keep telling herself. Namely, it’s to see the face Dean Smith will be making and how he will hopefully be rendered speechless when she struts into the office in a smart outfit instead of a coffee-stained shirt and wet pants.

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Afterglow - Ch. 27 (FIN)

af·ter·glow | \ ˈaf-tər-ˌglō
a pleasant effect or feeling that lingers after something is done, experienced, or achieved

Pairing: Dean Winchester x Reader

Summary: Running away from her life, Y/N ends up on the doorstep of her boyfriend’s apartment. In this story of heartbreak, survival, friendship, and love; she gets her first taste of the real L.A. and not the city she had often dreamed about. Her first hurdle? Dean Winchester; the grumpy neighbor who becomes more than just a pain in her ass. Yet, as things start to spiral, she soon realizes that the green-eyed resident from next door is a better person than she’s given him credit for.

Chapter Warnings: Uh-oh.... 

WC: 3,849

Series Beta’d by the amazing @winchest09​​​​ <3

This series is COMPLETE on Patreon

If you like what I’m writing, please consider leaving me a tip to keep me energized.

Y/N is in the process of packing up her belongings. Not everything, mind you, just her clothes and things of sentimental value she’s not ready to part with. She’s going home the same way she came here, only with one additional cat who’s going to serve as her co-pilot.

She agreed with her dad that she was going to go back to Chicago with him, but it was only going to be temporary. At least, that’s what she thinks, until her broken heart is mended. It might be good to have a change of scenery, to have time to dance and not constantly be reminded of Dean everywhere she looks. He still has his phone turned off, according to Benny, so maybe he really had cut them all out of his life. First, she had wanted to stay for the off chance Dean might have changed his mind and come back, but her father talked her out of it, and convinced her that going back is her best option.

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Leather & Lace - Chapter 02

Pairing: Dean Winchester x Reader

Summary: Dean Winchester, owner, and editor-in-chief of Craze magazine is an enigma, even to his own employees. There are only a selected few from his industry who have had the luck of meeting him. Of course, being mysterious brings rumors. Ones such as drinking blood because he’s a vampire, or, that he went vegan because he believes it’s the key to everlasting life. When Y/N joins the company, however, the latest story circulating is that he’s living somewhere on a private island with his much younger boy toy, and five pet tigers. Crazy, right? Still, she believes it all — up until she meets him, because, in person, Dean Winchester is the bane of her existence.

Warnings: A bit of tension if you squint..

Word Count: 2,446

Beta’d by the amazing @deanwanddamons​ <3

I’m 11 chapters ahead on Patreon in case you can’t wait :)

The meeting started with Sam taking the lead, and he thanked them all for the past month and the hard work they put into the magazine. It honestly makes her smile so bright to see a superior thanking employees so openly, even though it’s a big magazine and they’re all swamped with work. A little appreciation does go a long way and the way people are clapping, it clearly shows that they too, appreciate the acknowledgment.

Meanwhile, the guy from the elevator is still staring her down, a scowl seeming to be the default setting for his face.

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Afterglow - Ch. 26

af·ter·glow | \ ˈaf-tər-ˌglō
a pleasant effect or feeling that lingers after something is done, experienced, or achieved

Pairing: Dean Winchester x Reader

Summary: Running away from her life, Y/N ends up on the doorstep of her boyfriend’s apartment. In this story of heartbreak, survival, friendship, and love; she gets her first taste of the real L.A. and not the city she had often dreamed about. Her first hurdle? Dean Winchester; the grumpy neighbor who becomes more than just a pain in her ass. Yet, as things start to spiral, she soon realizes that the green-eyed resident from next door is a better person than she’s given him credit for.

Chapter Warnings: And it continues with the angst...

WC: 2,960

Series Beta’d by the amazing @winchest09​​​ <3

This series is COMPLETE on Patreon

If you like what I’m writing, please consider leaving me a tip to keep me energized.

He said to tell you that it’s over.

It’s over.

It’s over.

The words still ring in her ear, they are repeating themselves, echoing in her mind, despite her inability to breathe.

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