“Digging Your Own Grave” - Dean x Reader

“Digging Your Own Grave” - Dean x Reader

Rating Teen

Dean x Reader

Tags: Humor, Grumpy Dean, Adult Language, Fluff, Kissing, Reader Insert for “Optimism” Episode 14.6

Word Count: 1,000

Dean’s ego is wounded because of Jack calling him an old man. You aren’t doing anything to help Dean feel better.

I'm participating in @jacklesversebingo and this part will fill my dialogue, "Did you just kiss me to shut me up?" “Nooo?” square.

Big thanks to @zepskies for the chat and prompt that helped me rattle this little drabble out.

Smooth fucker!!! He's a grumpy asshole and I love him for it!!

Something New

Summary: Now that Chuck doesn’t control the narrative, Dean decides to take a new approach to your relationship. The only problem is that you’re not on the same page.

Warnings: angst, fluff, miscommunication, fwb, language. 

W/C: 3.5k

Characters: Dean Winchester. Mentioned: Sam Winchester, Eileen Lahey. 

Pairing: Dean Winchester x fem!Reader (you - no descriptions of body type or ethnicity), Sam Winchester x Eileen Lahey (mentioned).

READ IT NOW: Tumblr // AO3

The Girlfriend Who Remade Christmas

Part Nine: A Babe So Dear

Square: Holiday Miracle ~ spnchristmasbingo (2022)

Song: Carol of the Bells ~BarlowGirl

Pairing: Dean x Nicole {Nico/Nic} OFC

Summary: The investigation to uncover the mystery surrounding the abandoned child is surprisingly uneventful but brings about an interesting revelation.

Warnings: Fluff; A teeny bit of angst; Implied sex; Canon divergence

Word Count: 4,153

Beta: princessmisery666

The Road So Far https://forgottenworld.travelmap.net/ - no update for this chapter

It's always a cute time when Dean has to take care of a baby, because he's ridiculously good at it. 🥰

Loved this chapter.

The Haircut

This will fill the "Stop moving! I'm almost done." space on my @jacklesversebingo card. The prompt will be bolded.

Summary: Y/N is trying to Dean a favor. How can he repay her?

Warnings/Explicit 18+: None really. Kissing. Slightly pouty/adorable Dean. Pretty much all fluff.

Pairings: Dean x Y/N

Word Count: 977

A/N: I got a request from the lovely @k-slla:

I went with Dean. 😊 Loved the idea, hope you like the result my dear! And if anyone has any other requests for the remaining prompts on the card above, please message me or send me an ask. ❤️

The beautiful dividers both below and at the bottom were created by @saradika

Dean’s neck was scrunched into his shoulders as he heard Y/N’s scissors snipping away at the back of his head. Y/N paused briefly to cuff him lightly on the ear. 

“Good god, you’re such a baby. What do you think I’m doing back here?”

Dean straightened up on the wooden chair that Y/N had dragged into the kitchen to perform the task of trimming Dean’s slightly overgrown, light brown hair. He grunted softly and shrugged. 

“I dunno.” He mumbled like a petulant little boy. “Could be doing anything.”

Cute 🥰💜

All In or All Out?

Summary: Dean needs an answer.

Warnings: None really.

Pairings: Dean Winchester x Y/N

Word Count: 625

A/N: I got this very fun ask:

So, the photo above is the one I used. Hope you enjoy what I came up with for it. ❤️

The beautiful divider below and at the bottom was created by @talesmaniac89

"You gotta decide here and now." Dean told her in a low, firm voice. "I know it's not fair."

He looked up at her standing in front of him and tried to catch her gaze, but she purposely wasn't looking. "And you can think I'm an asshole if you want." He continued with a shrug. "That's your right, and you're probably not wrong."

Y/N shook her head, still refusing to look at him, far too aware of the sway those green eyes had over her. But Dean finally reached up to grab her chin and force her gaze back to his.

"Hey." He said quietly. "Look at me." 

She did, and she fell - like she knew she would. She would fall for this man forever. 

"I need to know, sweetheart." He said huskily. "You have to be all in or all out in this life. I know, because I've tried straddling the fence before and it just doesn't work. Live like that and hunters miss things, or they lose focus and they fumble. So, if we're gonna be together, I mean for real, for life," he was the one to drop his gaze this time, "then, Baby, you gotta decide if you can deal with me as a hunter, whether or not you can live this life with me."

She saw the muscle in his jaw flex. "Or, if it's too much for you then…okay. That's," he licked his lips, biting into the bottom one before clearing his throat, "that's okay. I get it."

He captured her gaze again and smiled softly. But his eyes were sad and they made Y/N’s heart ache. "But look…whatever you decide, sweetheart, I’ll always love you. That won't ever change."

Y/N closed her eyes and thought about the future she'd have with him; living in constant fear of losing him, watching him beat himself up when he lost people, knowing there was no way for her to stop him from doing that, putting up with him when he lashed out at her because the weight of the world was bearing down on his shoulders, and even knowing there might be some things he'd prioritize above their love - saving the world tended to be a sacrificial gig. 

She thought about all the bad, and tried to weigh it against the good, as she'd been doing for days since Dean first said that he needed her to give him an answer. She'd tumbled everything around and around in her mind and finally she was coming to the conclusion that there were dozens of reasons, big and small, for her to say no, to bow out.

And only one reason to stay, one reason to sign on to a hunter's life and that was the hunter sitting in front of her now. The reasons all boiled down to one very real, inescapable truth.

If she walked away from Dean Winchester, her soul would stay behind. 

She would never not need him, never not crave him. She was never, ever going to be able to say goodbye to that smile, and those eyes that held enough pain for fifty lifetimes, but that could still sparkle, bright and beautiful.

So, the choice he was giving her, wasn't really much of a choice. She was lost at their first hello.

She leaned forward and cupped his cheeks in her hands, her heart squeezing when he nuzzled into the touch.

"There is no other answer for me, Dean. You are my answer. My only answer." She shrugged and smiled lovingly before she pressed her mouth to his, feeling the heat of his lips sweep across her skin. She pulled back and, pressing her forehead to his, she made her vow.

"I'm all in."

Tags below the cut:

So beautifully executed and sweet 🥰🤩 obviously there’s no other choice 👍🏻

When the Stars Love You

(x)

Summary: Dean belongs in the starlight.

Warnings/Explicit 18+: Nothing really. Implied smut, angst, fluff.

Pairings: Dean Winchester x Y/N

Word Count: 1,028

A/N: So the beautiful @deanwinchesterswitch created the gorgeous aesthetic above as a request, and the original post can be found here. I was very inspired by this amazing piece of art, and with her permission I've written this little drabble in response to that inspiration. Thank you for this, Kym.

I'm placing this story somewhere in the 15th season, I guess. It's sometime after they realize that Chuck has been playing them all along, and that all he wants is one specific kind of ending. It sees Dean questioning everything in his life, and not sure what's real and what's Chuck. Y/N tries to help him through.

The beautiful divider below and at the bottom was created by @saradika

You loved Dean in the starlight. You were pretty sure the stars sparkled brighter when he was beneath them; they winked flirtatiously to get his attention. He'd turn his face up to them and they'd glow. You knew how they felt. When Dean focused his attention on you, you lit up too, bright and happy. 

AMAZING 🤩! Seriously I can’t put into words how much I adore this. It poetry and I loved how you shows the stars loving him to and how they couldn’t watch him fall apart 😢

Midnight Prince - couldn’t think of a better way to describe Dean Winchester.

Perfect 🤩

This is one of those fics that makes me doubt my own writing 💜

reader gender: unspecified

"Dean? Is that you?" His broad-shouldered silhouette appeared in the doorway. You sighed with relief.

"Yeah, it's me." He paced into the dark bedroom and his duffel bag dropped to the floor with a familiar thud. "Oh, God, it's good to be home."

You sat up, rubbing the sleep from your eyes, and watched him pull off his boots. The next second he was crawling up the bed toward you and flopping down with his arm curling around you securely. "I'm beat," he sighed, sinking into the pillow.

You laughed lightly and ran your fingers through his hair. He leaned into the touch and hummed a content noise. "Babe... don't take this the wrong way but‚ you smell like a wet dog."

He laughed, a deep, gruff sound that you felt reverberate in his chest. He rolled onto his back beside you. "Yeah... sorry... I'm too tired even to shower and there may have been an incident with a bog on the case."

You nodded, rolling closer to him again and resting your head on his shoulder and your hand landing flush in the center of his chest. His hand closed over the top of it in an instant and gave it a gentle squeeze. "That's alright. I don't mind," you said with a laugh. "Sleep. We can shower together in the morning..." You leaned up and kissed his lips softly.

He pulled you in more tightly and kissed you back, hungry for the taste of you. "You know, that really does make a shower more appealing..."

"I thought you were exhausted," you said, quirking an eyebrow at him.

He shrugged. "I am but—you, naked? It's like an instant shot of caffeine." His fingers trailed lightly down your back, following the gentle curve of your spine.

"Sleep, Dean. You can have your caffeine in the morning," you said, kissing him softly again.

He sighed and relished the feeling of you settling in against him. "You're the boss..." Soon, he was asleep.

Prompt: "You smell like a wet dog."

Cute 🥰

Something New

Summary: Now that Chuck doesn’t control the narrative, Dean decides to take a new approach to your relationship. The only problem is that you’re not on the same page.

Warnings: angst, fluff, miscommunication, fwb, language. 

W/C: 3.5k

Characters: Dean Winchester. Mentioned: Sam Winchester, Eileen Lahey. 

Pairing: Dean Winchester x fem!Reader (you - no descriptions of body type or ethnicity), Sam Winchester x Eileen Lahey (mentioned).

Challenge: @deanwanddamons 3K Follower Challenge - Three’s A Crowd Prompts: Friends with benefits / Quote #5 - “We going to fight or make out, ’cause I’m getting some real mixed signals here” / Third wheel - Ghost

Notes: Set after season 14.

Betas: @deanwinchesterswitch

Graphics: title card made my be // dividers @talesmaniac89

Master Lists: Supernatural // All The Fandoms (Main)

Something New

Dean scrutinizes his reflection in the bathroom mirror, jutting out his chin, twisting left then right, smooths his hands through his longer hair, traveling to scrub roughly against the growing beard on his cheeks and chin. Though his hands remain on his face, from your perch on the bed, your eyes continue the journey south to roam over him - broad shoulders, muscles of his back, sharpness of his hips, tightness of his ass, beefy thighs, and those virulent, thick fingers.

He is one hell of a man, and you pull your bottom lip between your teeth, remembering all the times that intoxicating body has pinned you down and wrung screaming orgasms from you.

Your relationship is strictly friends with benefits. Sam, Eileen, and Dean were kind enough to let you join their hunting group while trying to take down Chuck two months ago. Inevitably in the first few weeks, you’d fallen into bed with Dean, and after the Winchesters defeated God, it became a regular thing.

A regular thing that has yet to become boring or bland. Dean keeps it exciting and fresh. Honestly, you're not even sure how he’s standing right now. He found some website that posts daily sex positions, and of course, he wants to try all of them. Even if he’s done it before, he finds an innovative way to make it new.

Thank you 😊

Even Better Than Pie

Summary: Y/N knows just how to make Dean smile.

A/N: Saw this post - and this fluffy piece just demanded to be written.

Warnings: None really. Kissing. Implied smut. Smidge of angst. Pretty much, all fluff.

Pairings: Dean Winchester x Y/N

Word Count: 787

The beautiful divider below and at the bottom were created by @talesmaniac89.

Y/N walked into the library, wiping her hands on the yellow apron she wore, and looking for Dean. She found him in one of the padded chairs nestled into the corner of the bookshelves. He had his feet up on one of the wooden chairs, and he looked relaxed. But Y/N knew him well enough to know his mind was somewhere else, by the way his head was tilted to one side, and his rough fingers ran contemplatively back and forth across his lips.

As he noticed her approach, his expression shifted and a soft smile blossomed on his face. “Hey.” He said quietly.

Y/N reached him and climbed into his lap, straddling his outstretched legs and pressing her knees into the chair on either side of his thighs. 

“Hey yourself.” She responded with a smile, reaching out to scrape her long fingernails through the scruff on his cheek. “Penny for your thoughts?”

Dean shook his head lightly. “N’ah, definitely not worth a whole penny.”

This was sweeter than pie 🥧💜 love it 🥰

Something New

Summary: Now that Chuck doesn’t control the narrative, Dean decides to take a new approach to your relationship. The only problem is that you’re not on the same page.

Warnings: angst, fluff, miscommunication, fwb, language. 

W/C: 3.5k

Characters: Dean Winchester. Mentioned: Sam Winchester, Eileen Lahey. 

Pairing: Dean Winchester x fem!Reader (you - no descriptions of body type or ethnicity), Sam Winchester x Eileen Lahey (mentioned).

Challenge: @deanwanddamons 3K Follower Challenge - Three’s A Crowd Prompts: Friends with benefits / Quote #5 - “We going to fight or make out, ’cause I’m getting some real mixed signals here” / Third wheel - Ghost

Notes: Set after season 14.

Betas: @deanwinchesterswitch

Graphics: title card made my be // dividers @talesmaniac89

Master Lists: Supernatural // All The Fandoms (Main)

Something New

Dean scrutinizes his reflection in the bathroom mirror, jutting out his chin, twisting left then right, smooths his hands through his longer hair, traveling to scrub roughly against the growing beard on his cheeks and chin. Though his hands remain on his face, from your perch on the bed, your eyes continue the journey south to roam over him - broad shoulders, muscles of his back, sharpness of his hips, tightness of his ass, beefy thighs, and those virulent, thick fingers.

He is one hell of a man, and you pull your bottom lip between your teeth, remembering all the times that intoxicating body has pinned you down and wrung screaming orgasms from you.

Your relationship is strictly friends with benefits. Sam, Eileen, and Dean were kind enough to let you join their hunting group while trying to take down Chuck two months ago. Inevitably in the first few weeks, you’d fallen into bed with Dean, and after the Winchesters defeated God, it became a regular thing.

A regular thing that has yet to become boring or bland. Dean keeps it exciting and fresh. Honestly, you're not even sure how he’s standing right now. He found some website that posts daily sex positions, and of course, he wants to try all of them. Even if he’s done it before, he finds an innovative way to make it new.

I love their conversation that keeps being interrupted by the ghost 😆

😜🙃 thank you ☺️

Breaking

Warnings/Explicit 18+: Smut - this is just all smut. Very little plot to the porn here. Rough, intense sex, unprotected p in v, oral (f receiving) dirty talk, it's all Yvette's fault.

(x)

Summary: Y/N and Dean play some pool; who's the winner?

Warnings/Explicit 18+: Smut - this is just all smut. Very little plot to the porn here. Rough, intense sex, unprotected p in v, oral (f receiving) dirty talk, it's all Yvette's fault.

Pairings: Dean Winchester x Y/N

Word Count: 2,510

A/N: @justagirlinafandomworld shared the pic above, and it got me immediately thinking of Dean in his fed suit, and all the filthy thoughts began swirling.

So, here ya go - enjoy the dirtiness! 😁

The beautiful dividers below at the bottom were created by @talesmaniac89.

Main Masterlist || Tag Lists

“What are we doing here, Winchester?” Y/N asked once again as they stepped through the thick wooden door that led them back into the bar they’d been in earlier in the day.

Dean flicked the lights on, casting a pale bluish tint over the room from the neon sign that sputtered to life over the bar. 

“I don’t get it." Y/N exclaimed, clearly confused. "Did Warren say there was still a problem? Is the ghost back somehow? Did he see something?”

Dean shook his head as he locked the bar door behind himself, and wandered up the three stairs leading to the pool tables. 

“Nope. He’s good, very grateful that he can reopen the bar tomorrow without fear of his patrons being taken out by a homicidal ghost.”

Y/N threw her hands up with an exasperated laugh. “Then I’m gonna ask for the fourth time now, why are we back here?”

🥵 okaaaay !! Playing pool with Dean sounds fun 🤩 😝

The Longest Time

Summary: For the longest time, Dean hasn't allowed himself to dream of a future, but Wynter changes things.

Warnings: fluff, flangst.

W/C: 6k

Characters: Dean Winchester, Sam Winchester, Eileen Leahy, OFC (Wynter).

Pairing: Dean Winchester x OFC (Wynter), Sam Winchester x Eileen Leahy.

Notes: the finale didn’t happen; Chuck is gone. 

A/N: @justagirlinafandomworld sent me this request, and the muses loved it. Yvette, thank you so much for the inspiration. I had a blast writing this, I Mary Sue’d Christmas, and I ain’t even sorry. 😍🤣

Betas: @deanwinchesterswitch thank you so much!! // all mistakes are my own.

Graphics: dividers by @talesmaniac89

Master Lists: Main // Dean Winchester

Sam and Dean step out of the Impala in the bunker's garage, tired but happy to be home. Since Chuck’s defeat, it’s been monster-of-the-week type gigs, but it hasn’t made the fights any easier.

Sam opens the back door for Eileen and helps her out, kissing her when she’s on her feet, and Dean smiles fondly as he passes to the trunk. 

For the longest time, Dean had given up on a future. He wasn’t living. He had been surviving, taking one breath after the next, going through the motions. Seeing his brother happy causes a flutter of restlessness in his chest, and he thinks of Wynter, likely sound asleep in her bed, and it grows into a bubble of excitement that wants to erupt, but he holds it back.

It’s almost midnight, so Dean doesn’t expect Wynter to be waiting up to greet them, but she was expecting them home, so he’s hopeful there are at least some delicious leftovers waiting in the kitchen.

“I hope Wynter made pie,” Dean muses aloud as they walk the corridors from the garage. 

Sam rolls his eyes, “she always makes you pie when we’re gone longer than a day. She puts her anxiety into baking.”

“Well, her anxiety is delicious,” he jokes. 

“Y’know,” Sam says, holding the door to the library open and motioning for Eileen to enter first while focusing on Dean. Before Sam even inhales to continue, Dean knows he’s about to start a lecture. “Eating this late is bad for…” 

Eileen freezes with a loud gasp a few steps inside the room, interrupting the lecture. The boys hurry to follow, echoing her gasp of wonderment.

*SWOON* (There's literally no words to express how wonderful this is, so I'm just over here swooning to death.)

Thank you ☺️ I swooned the entire time I was writing it 😂

The Longest Time

Summary: For the longest time, Dean hasn't allowed himself to dream of a future, but Wynter changes things.

Warnings: fluff, flangst.

W/C: 6k

Characters: Dean Winchester, Sam Winchester, Eileen Leahy, OFC (Wynter).

Pairing: Dean Winchester x OFC (Wynter), Sam Winchester x Eileen Leahy.

Notes: the finale didn’t happen; Chuck is gone. 

A/N: @justagirlinafandomworld sent me this request, and the muses loved it. Yvette, thank you so much for the inspiration. I had a blast writing this, I Mary Sue’d Christmas, and I ain’t even sorry. 😍🤣

Betas: @deanwinchesterswitch thank you so much!! // all mistakes are my own.

Graphics: dividers by @talesmaniac89

Master Lists: Main // Dean Winchester

Sam and Dean step out of the Impala in the bunker's garage, tired but happy to be home. Since Chuck’s defeat, it’s been monster-of-the-week type gigs, but it hasn’t made the fights any easier.

Sam opens the back door for Eileen and helps her out, kissing her when she’s on her feet, and Dean smiles fondly as he passes to the trunk. 

For the longest time, Dean had given up on a future. He wasn’t living. He had been surviving, taking one breath after the next, going through the motions. Seeing his brother happy causes a flutter of restlessness in his chest, and he thinks of Wynter, likely sound asleep in her bed, and it grows into a bubble of excitement that wants to erupt, but he holds it back.

It’s almost midnight, so Dean doesn’t expect Wynter to be waiting up to greet them, but she was expecting them home, so he’s hopeful there are at least some delicious leftovers waiting in the kitchen.

“I hope Wynter made pie,” Dean muses aloud as they walk the corridors from the garage. 

Sam rolls his eyes, “she always makes you pie when we’re gone longer than a day. She puts her anxiety into baking.”

“Well, her anxiety is delicious,” he jokes. 

“Y’know,” Sam says, holding the door to the library open and motioning for Eileen to enter first while focusing on Dean. Before Sam even inhales to continue, Dean knows he’s about to start a lecture. “Eating this late is bad for…” 

Eileen freezes with a loud gasp a few steps inside the room, interrupting the lecture. The boys hurry to follow, echoing her gasp of wonderment.

Christmas Eve Reblog

The Longest Time

Summary: For the longest time, Dean hasn't allowed himself to dream of a future, but Wynter changes things.

Warnings: fluff, flangst.

W/C: 6k

Characters: Dean Winchester, Sam Winchester, Eileen Leahy, OFC (Wynter).

Pairing: Dean Winchester x OFC (Wynter), Sam Winchester x Eileen Leahy.

Notes: the finale didn’t happen; Chuck is gone. 

A/N: @justagirlinafandomworld sent me this request, and the muses loved it. Yvette, thank you so much for the inspiration. I had a blast writing this, I Mary Sue’d Christmas, and I ain’t even sorry. 😍🤣

Betas: @deanwinchesterswitch thank you so much!! // all mistakes are my own.

Graphics: dividers by @talesmaniac89

Master Lists: Main // Dean Winchester

Sam and Dean step out of the Impala in the bunker's garage, tired but happy to be home. Since Chuck’s defeat, it’s been monster-of-the-week type gigs, but it hasn’t made the fights any easier.

Sam opens the back door for Eileen and helps her out, kissing her when she’s on her feet, and Dean smiles fondly as he passes to the trunk. 

For the longest time, Dean had given up on a future. He wasn’t living. He had been surviving, taking one breath after the next, going through the motions. Seeing his brother happy causes a flutter of restlessness in his chest, and he thinks of Wynter, likely sound asleep in her bed, and it grows into a bubble of excitement that wants to erupt, but he holds it back.

It’s almost midnight, so Dean doesn’t expect Wynter to be waiting up to greet them, but she was expecting them home, so he’s hopeful there are at least some delicious leftovers waiting in the kitchen.

“I hope Wynter made pie,” Dean muses aloud as they walk the corridors from the garage. 

Sam rolls his eyes, “she always makes you pie when we’re gone longer than a day. She puts her anxiety into baking.”

“Well, her anxiety is delicious,” he jokes. 

“Y’know,” Sam says, holding the door to the library open and motioning for Eileen to enter first while focusing on Dean. Before Sam even inhales to continue, Dean knows he’s about to start a lecture. “Eating this late is bad for…” 

Eileen freezes with a loud gasp a few steps inside the room, interrupting the lecture. The boys hurry to follow, echoing her gasp of wonderment.

You already know how excited I was about this when you shared the idea. You already know how I gushed in the doc and on Discord while reading it.

BUT... I'm gonna do it again!

I love this SO much. From her cute, very fitting name to Dean being adorably clueless, this is a sweet and fun fic for the holidays. I’ve already re-read twice since you posted it. Two delightful idiots dancing around their feelings.

That last line will always make me smile, and my heart swell. Did I tell you I adore it? Because I ADORE it.

Couldn’t have done it without babes 💜

The Longest Time

Summary: For the longest time, Dean hasn't allowed himself to dream of a future, but Wynter changes things.

Warnings: fluff, flangst.

W/C: 6k

Characters: Dean Winchester, Sam Winchester, Eileen Leahy, OFC (Wynter).

Pairing: Dean Winchester x OFC (Wynter), Sam Winchester x Eileen Leahy.

Notes: the finale didn’t happen; Chuck is gone. 

A/N: @justagirlinafandomworld sent me this request, and the muses loved it. Yvette, thank you so much for the inspiration. I had a blast writing this, I Mary Sue’d Christmas, and I ain’t even sorry. 😍🤣

Betas: @deanwinchesterswitch thank you so much!! // all mistakes are my own.

Graphics: dividers by @talesmaniac89

Master Lists: Main // Dean Winchester

Sam and Dean step out of the Impala in the bunker's garage, tired but happy to be home. Since Chuck’s defeat, it’s been monster-of-the-week type gigs, but it hasn’t made the fights any easier.

Sam opens the back door for Eileen and helps her out, kissing her when she’s on her feet, and Dean smiles fondly as he passes to the trunk. 

For the longest time, Dean had given up on a future. He wasn’t living. He had been surviving, taking one breath after the next, going through the motions. Seeing his brother happy causes a flutter of restlessness in his chest, and he thinks of Wynter, likely sound asleep in her bed, and it grows into a bubble of excitement that wants to erupt, but he holds it back.

It’s almost midnight, so Dean doesn’t expect Wynter to be waiting up to greet them, but she was expecting them home, so he’s hopeful there are at least some delicious leftovers waiting in the kitchen.

“I hope Wynter made pie,” Dean muses aloud as they walk the corridors from the garage. 

Sam rolls his eyes, “she always makes you pie when we’re gone longer than a day. She puts her anxiety into baking.”

“Well, her anxiety is delicious,” he jokes. 

“Y’know,” Sam says, holding the door to the library open and motioning for Eileen to enter first while focusing on Dean. Before Sam even inhales to continue, Dean knows he’s about to start a lecture. “Eating this late is bad for…” 

Eileen freezes with a loud gasp a few steps inside the room, interrupting the lecture. The boys hurry to follow, echoing her gasp of wonderment.

Next day reblog…

The Longest Time

Summary: For the longest time, Dean hasn't allowed himself to dream of a future, but Wynter changes things.

Warnings: fluff, flangst.

W/C: 6k

Characters: Dean Winchester, Sam Winchester, Eileen Leahy, OFC (Wynter).

Pairing: Dean Winchester x OFC (Wynter), Sam Winchester x Eileen Leahy.

Notes: the finale didn’t happen; Chuck is gone. 

A/N: @justagirlinafandomworld sent me this request, and the muses loved it. Yvette, thank you so much for the inspiration. I had a blast writing this, I Mary Sue’d Christmas, and I ain’t even sorry. 😍🤣

Betas: @deanwinchesterswitch thank you so much!! // all mistakes are my own.

Graphics: dividers by @talesmaniac89

Master Lists: Main // Dean Winchester

Sam and Dean step out of the Impala in the bunker's garage, tired but happy to be home. Since Chuck’s defeat, it’s been monster-of-the-week type gigs, but it hasn’t made the fights any easier.

Sam opens the back door for Eileen and helps her out, kissing her when she’s on her feet, and Dean smiles fondly as he passes to the trunk. 

For the longest time, Dean had given up on a future. He wasn’t living. He had been surviving, taking one breath after the next, going through the motions. Seeing his brother happy causes a flutter of restlessness in his chest, and he thinks of Wynter, likely sound asleep in her bed, and it grows into a bubble of excitement that wants to erupt, but he holds it back.

It’s almost midnight, so Dean doesn’t expect Wynter to be waiting up to greet them, but she was expecting them home, so he’s hopeful there are at least some delicious leftovers waiting in the kitchen.

“I hope Wynter made pie,” Dean muses aloud as they walk the corridors from the garage. 

Sam rolls his eyes, “she always makes you pie when we’re gone longer than a day. She puts her anxiety into baking.”

“Well, her anxiety is delicious,” he jokes. 

“Y’know,” Sam says, holding the door to the library open and motioning for Eileen to enter first while focusing on Dean. Before Sam even inhales to continue, Dean knows he’s about to start a lecture. “Eating this late is bad for…” 

Eileen freezes with a loud gasp a few steps inside the room, interrupting the lecture. The boys hurry to follow, echoing her gasp of wonderment.

In case you missed it…

The Longest Time

Summary: For the longest time, Dean hasn't allowed himself to dream of a future, but Wynter changes things.

Warnings: fluff, flangst.

W/C: 6k

Characters: Dean Winchester, Sam Winchester, Eileen Leahy, OFC (Wynter).

Pairing: Dean Winchester x OFC (Wynter), Sam Winchester x Eileen Leahy.

Notes: the finale didn’t happen; Chuck is gone. 

A/N: @justagirlinafandomworld sent me this request, and the muses loved it. Yvette, thank you so much for the inspiration. I had a blast writing this, I Mary Sue’d Christmas, and I ain’t even sorry. 😍🤣

Betas: @deanwinchesterswitch thank you so much!! // all mistakes are my own.

Graphics: dividers by @talesmaniac89

Master Lists: Main // Dean Winchester

Sam and Dean step out of the Impala in the bunker's garage, tired but happy to be home. Since Chuck’s defeat, it’s been monster-of-the-week type gigs, but it hasn’t made the fights any easier.

Sam opens the back door for Eileen and helps her out, kissing her when she’s on her feet, and Dean smiles fondly as he passes to the trunk. 

For the longest time, Dean had given up on a future. He wasn’t living. He had been surviving, taking one breath after the next, going through the motions. Seeing his brother happy causes a flutter of restlessness in his chest, and he thinks of Wynter, likely sound asleep in her bed, and it grows into a bubble of excitement that wants to erupt, but he holds it back.

It’s almost midnight, so Dean doesn’t expect Wynter to be waiting up to greet them, but she was expecting them home, so he’s hopeful there are at least some delicious leftovers waiting in the kitchen.

“I hope Wynter made pie,” Dean muses aloud as they walk the corridors from the garage. 

Sam rolls his eyes, “she always makes you pie when we’re gone longer than a day. She puts her anxiety into baking.”

“Well, her anxiety is delicious,” he jokes. 

“Y’know,” Sam says, holding the door to the library open and motioning for Eileen to enter first while focusing on Dean. Before Sam even inhales to continue, Dean knows he’s about to start a lecture. “Eating this late is bad for…” 

Eileen freezes with a loud gasp a few steps inside the room, interrupting the lecture. The boys hurry to follow, echoing her gasp of wonderment.

STAAACEYYYY!!! I LOVE EVERYTHING ABOUT THIS!!!!!

The pining, omg you did it so well, they're such idiots and I love them. LOL and I love that you went with the name Wynter, it's like a callback to the fic of our youth. And her decorating the entire bunker was awesome!

I'm going to try to address all the things that made me smile, which is going to be hard to not just copy and paste the whole fic, because I was smiling while reading the whole thing! But here we go!

Sam rolls his eyes, “she always makes you pie when we’re gone longer than a day. She puts her anxiety into baking.”

“Well, her anxiety is delicious,” he jokes. 

She bakes him pie when he's gone, she stays in his room when she has a nightmare, and reads his books because they remind her of him. Ooooooh, this is so good already!!!

“It smells so good in here,” Dean says, announcing he’s ready to be spoken to. 

I really love how much Dean is not a morning person, and that right there made me laugh out loud. Don't speak to him unless spoken to, it's hilarious. 😆

Hanging mistletoe had been a stupid idea. She sees it now. Sam and Eileen played along, kissing her cheek every time they were under it, but clearly, Dean was uncomfortable, and she never wanted that.

You know what, I love how adorable Sam and Eileen are in this. Not just with each other - though they are so sweet and smitten it's fluffy as hell💕; but with Wynter too. They didn't have to play along but they did and that's so sweet of them! But, no, baby, don't think that it was a stupid idea! It wasn't!! 🥺

He stares at her for a moment, wondering how she hasn’t figured it out yet. That’s his love language or whatever sappy saying the kids use nowadays. Everything she just said is how he shows her he wants to explore their relationship. Perhaps he does need to say it.

Yesss, that is his love language and he is telling her every day and every way he knows how!! And yes, maybe maybe you should try saying it out loud Dean!!

Still, she’s never been a shy woman, and she just went on a date with another guy. If she wanted him, Dean’s sure she’d have said something.

Noooooo!! I'm laughing and crying because this is all in the same paragraph which is suiting because this train of thought is definitely what he would do!!! 'Hey maybe I should - nah, if it was something she wanted she'd tell me.' Winchester, you're killing me!!😩

That twists a knot in his heart. She shouldn’t be lonely. He’s right there. He puts down the last chunk of his burger, suddenly feeling nauseous. “You’re lonely?” He doesn’t quite stutter, but the acid in his stomach churns, and he has to work to keep it from rising. 

It was the "He's right there." that squeezed my heart. 😭 This whole conversation was so honest, and I love that they were both saying it without actually saying it - it was perfect and exactly what I was hoping for!! I mean look at this one!!! ⬇️😭😭😭

Wynter fixes her eyes to his, and he can see how much she’s willing him to understand. He does - more than she realizes.

They understand each other, they know each other and love each other on every level outside of intimacy. And yet that last level is something they both want and I'm flailing over it!!!

I'm so, so, so unbelievably happy with this story, Stace!! That last scene in the kitchen was absolute💓 heaven!! 💓The pining, the misunderstanding, the slight jealousy - omg, did I not mention the part where he tries to talk her out of going on that date??? And then when he watches her on the date??? And she knows but doesn't tell him she knows until the very end????!?!?! 🥲💓💓💓💓💓💓

I love it, I love it, I love it, I LOVE YOU THANK YOU FOR THIS BEAUTIFUL CHRISTMAS STORY!!!

Yay 🥳 I’m so so so so so happy you loved it 🥰

She seeks him out whether he’s there or not, he’s her comfort blanket 💜

I am very much like Dean in that I am NOT a morning person 😝

Hanging Mistletoe is either a very good idea or a really bad one, there’s no in between, at least all the stories I’ve heard 🤷🏼‍♀️

Actions speak louder than words but sometimes the words need to be said!!

He’s a confident man, but he’s still got his doubts.

The kitchen scene was my favorite bit 🥰💜

Thank you for the request and inspiring the muses 💋 I’m hoping the muses are happy to move on to the angsty one with Steve now…