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Among the ruins by silver stake through the heart (Dusk_Sky)
Fandoms: Supernatural (TV 2005)
05 Feb 2026
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The Apocalypse happened and the angels won. Humanity is only a memory now.
Castiel is wandering aimlessly when he stumbles upon what may be the last living human. After some hesitation, he decides to save him, not suspecting how much this meeting will change his life and his beliefs.
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At thirty-six, Dean Winchester is the Captain of Lawrence Fire Station 24 — respected, decorated, and trusted with lives when everything is burning down. He runs his crew with precision, authority, and gallows humor, the kind of man you want beside you when the smoke gets thick. He has the house. The career. The scars to prove he earned both.
What he doesn’t have is anyone waiting for him when the sirens go quiet.
Dean tries to explain why Castiel doesn’t fit into his life — too quiet, too gentle, too different from anyone he’s ever dated.
Sam, who’s heard every version of this argument before, gently points out the truth Dean keeps avoiding: maybe the problem isn’t Castiel’s differences — maybe it’s that Dean has spent his whole life choosing what’s safe instead of what he actually needs.
And maybe what he needs is someone entirely unfamiliar… even if that scares him.
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"You've been dating the same type of person your whole life, and where has it gotten you? Alone in a house that's too quiet. You always go for what's easy, what's familiar. But maybe what you need isn't easy. Maybe what you need is different. Maybe what you need is a nerdy beekeeper who talks about feelings."
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Dean is on tour with the band for the holidays and he misses his boyfriend.
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New Year's Eve, 2002 - Dean's cold and lonely in Northern Michigan, until a stranger heats things up.
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At the altar of his family by silver stake through the heart (Dusk_Sky)
Fandoms: Supernatural (TV 2005)
24 Dec 2025
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The angel left. Finally. Jimmy is free. He can go home.
As Jimmy heads back to his family, he meets a boy who cared for the angel.
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Deep in the woods by silver stake through the heart (Dusk_Sky)
Fandoms: Supernatural (TV 2005)
22 Oct 2025
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Dean loves his life at Sonny's boys home. He gets to go to school, have a normal life and not worry about the monsters hiding in the dark. (Well, not too much.) He gets to have friends too. Cas is his favorite, even though he's a little weird.
And maybe Cas is not human.
POVs: Dean (mostly), Sonny (a little)
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“No bringing me back, okay? You know… You know that always ends bad,” Dean had said.
Well, Dean had also said that they always ignored the whole ‘not bringing each other back’ thing because of their deep, abiding love for each other. It was a non-promise, and there was no way in Rowena’s Hell that Sam was going to live out the rest of his life sitting on top of a bunker full of resources and not do something to reverse what had happened to Dean.
Sam doesn’t need to dig very far before he lands on a reasonable idea: use Henry’s time travel spell and finish what Dad never could, and take out the masked vamps before they ever become an issue. That way, Dean wouldn’t have to die—least of all like that—in the first place. Simple.
Except that the spell lands 2020 Sam smack-dab in the middle of a motel parking lot, where a lonely Dean is reeling from 2003 Sam’s lack of communication.
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Don't tell another soul by silver stake through the heart (Dusk_Sky)
Fandoms: Supernatural (TV 2005)
19 Oct 2025
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When John died, Dean drove Sam to Bobby so his brother wouldn't end up in the system. Sam seems to dislike his decision, but Dean can't be sure: they aren't talking anymore, despite living in the same place.
Dean's trying to get used to this new life, but it's hard, especially with people bringing back John's memory every now and then. He wants to move on. Is it too much to ask?
His new friend—his very first friend actually—doesn't think so.
Series
- Part 3 of Things change
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It was far from the first time Dean'd had to choose between food, or in this case beer, and having enough to pay for even a shitty motel. If he was gonna spend another long, lonely night in the car, he was at least gonna enjoy the view first.
For Suptober 2025 Day 13: Star Gazing
Series
- Part 9 of Suptober 2025
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The world ended three years ago and the stars had been his only companion since the apocalypse started.
His world started one year ago and an celestial being became his companion among the stars.
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Suptober 2025
Prompt for day 13: Star-gazing
Series
- Part 13 of Suptober 2025
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Something about heartbreak by silver stake through the heart (Dusk_Sky)
Fandoms: Supernatural (TV 2005)
30 Aug 2025
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Dean and Casey became friends because of their complicated relationship to their better half. They get each other and exorcize most of their heartbreak by writing and singing about it.
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Dean spends a lot of his life wishing for something that seems unattainable.
This is what happens when he gets it. -
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Dean runs into an old friend on a case in Ohio, and it stirs up some bittersweet memories.
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Castiel had bought the stamps with good intentions. He’d thought they might be a gentle counterbalance to the occasional academic brutality of his feedback. A harmless gesture. Encouragement. Positive reinforcement.
Apparently, they’re multipurpose.
Castiel smiles, teeth catching behind his lips. “You’ll get another stamp if you ask nicely.”
Dean exhales, eyes fluttering shut. “Fuck.”
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At 22, Dean Winchester is hunting alone while his dad chases the demon that tore their family apart. When he stumbles into a nest of vampires, Dean becomes their next meal. Outnumbered and cornered, he’ll have to fight to survive.
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Dr. Castiel Novak’s research is falling apart until a young man with signs of a violent psychotic break arrives at the ER. As Castiel treats his patient’s break from reality, he realizes this man may be the only person he can trust.
Written for the Destiel Angst Bang 2025
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when dean first creates the wicker-man, he does so out of loneliness. it watches the door, watches over him. it’s like there’s another person to come home to.
he knows it’s not real. he keeps telling himself that. and then the wicker-man comes to life.
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A little backstory on Dean's life after Sam left for Stanford, how he met Castiel, and opened a bed & breakfast in the heart of Kansas.
Sad boy Dean hours in the earlier chapters. Itty-bitty bashing of Sam and not so itty-bitty bashing of John. Part 4 of my series but you don't need to read the earlier parts.Series
- Part 4 of We fell in love in October
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While everyone else eagerly ate up the land looking westward, Dean had a hard time envisioning much of anything for himself on the horizon. Dad was dead. Sam had left for the stability of Californian settlements. Loneliness was Dean’s steadiest partner now as he carried on the torch of the family business
That is, until a simple ghost hunt in the railway town of Ashland, Oregon, turns into a tangle with a god, and Dean begins thinking he should’ve been looking skyward instead.
‘Cause sometimes, the sky looks back—and it wants.
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Private Dean Winchester finally pulls one prank too many and is about to face court martial when he witnesses a horrifying event that costs him his one and only true friend. But the tragedy proves to be an opportunity when Dean is whisked away to take part in something called "Project Castiel." He's been told it's the only way to get his friend back. What he gets back isn't anything like what he expects.
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The shapeshifter in s1 e6 takes on Dean's shape in order to survive. He quickly realizes that he and Dean have more in common than they reasonably should. After a lifetime of loneliness, could this strange connection he feels to Dean be the answer to his prayers?
