1 - 20 of 957 Works in Emotionally Hurt Dean Winchester
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After losing his adoptive parents in a tragedy that never made sense, Cal starts chasing ghosts—both real and imagined. A single photograph leads him to the name Winchester and the possibility of a family he never knew. But finding them means uncovering the truth about what it really costs to belong in their world.
This story follows an original character, Cal Winchester — the younger half-brother of Sam and Dean. It’s about finding family, losing it, and learning how love can hurt just as deeply as it heals.
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Dean has a rough night twice. Castiel interrupts. Twice.
Series
- Part 23 of Kinktober/Whumptober/Fictober 2025
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When Dean has a year left to live (season 3), he finally decides to write his journal. Maybe someone will find it? Or he struggles with many thoughts every day and hopes that it will help him?
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(Let Him Suffer) It All Ends The Same Anyway by Jupiter_Inkwell
Fandoms: Supernatural (TV 2005)
18 Oct 2025
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After a devastating diagnosis, Sam decides to call his brother, Dean, after not talking for two years. With his best friend, girlfriend, and brother at his side, Sam fights cancer. But not everything ends the way we hope.
Castiel has always been seen as an outcast; something of bad luck. The mistreatment never makes him sour; instead, he learns to love his father's creation even if that means his heart breaks as he is forced to watch a boy die when he could heal him.
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Dean kicked human Cas out of the bunker.
He didn't expect that watching him go would rip his heart out.
Now Dean has finally tracked Cas down - and he is determined to get his angel back. -
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A seemingly ordinary case in a bank takes an unexpected turn when it becomes a hostage situation. Dean is ready to do anything to protect Sam, but Sam is the one who makes the sacrifice. Amid bullets, explosions, and prayers Dean has never spoken before, the two brothers discover just how far they’re willing to go to save each other.
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Dean's been nesting with Castiel’s trenchcoat every night, ever since he pulled it out of the lake. Sam doesn't know what to make of it.
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The Distance Between (Dean Winchester + Reader) by magneder
Fandoms: Supernatural (TV 2005)
17 Oct 2025
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Some people aren't meant to stay - only to leave you changed.
He was supposed to be another right swipe.
A quiet man with sharp eyes and too many walls.
You weren't supposed to fall for someone who disappears for months, only to come back like nothing happened.
Their story was all smoke and silence - hookah haze, half-finished texts, and nights that felt like promises.
But when you finally walk away, it's not the end.
Because some people aren't meant to stay.
They teach you, change you, and leave - quietly, without closure.
And somehow, that's enough.
A dark, slow-burn psychological romance with AU Dean Winchester + Reader
Soundtrack: "Bowery" by Zach Bryan & Kings of Leon.
- Language:
- English
- Words:
- 652
- Chapters:
- 1/?
- Hits:
- 6
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Through every death, hunt, and homecoming, the Impala endures—the silent witness to the Winchesters’ story. It was never just a car. It was their home, their history, and their heartbeat. Baby remembers everything—the love, the loss, and the family it carried through all the fires.
It remembered what the living forgot.
What the dead had buried.
It remembered it all.(Set during the last scene of 2.02.)
Series
- Part 5 of The Stanford Series
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Não estou mais sozinho - DeanSpencer by Jupiter_daughter
Fandoms: Criminal Minds (US TV), Supernatural (TV 2005), Harry Potter - J. K. Rowling
16 Oct 2025
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Dean estava sozinho.
Ele sabia que em algum momento ia terminar daquele jeito, mas não esperava que fosse se sentir tão mal, tão sozinho e tão abandonado. -
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The second volume in my series, How To Fix A Winchester, a series of prompt and episode based one shots/standalone chapters. Just the boys saving and taking care of each other. Alway happy endings, lots of comfort and fluff!
Series
- Part 2 of Brothers On A Road Trip
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John's dead, and Dean skips right over denial into anger
Series
- Part 14 of SPN 2025 Inktober Drabbles
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The morning begins in laughter and ends in silence.
One spark, one explosion, and the bunker turns into a tomb. The air tastes of blood and ozone. Dean and Cas run through crimson-lit corridors while shadows crawl where light used to be.
It’s not a ghost, not a demon — something older, something colder. It doesn’t whisper, it doesn’t roar — it waits.
And when it finally moves, the walls themselves seem to flinch.
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Suptober 2025
Prompt for day 10: Power Outage
Series
- Part 10 of Suptober 2025
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Dead Weight II by WritingWithTheWinchesters for Koraesdoodles
Fandoms: Supernatural (TV 2005)
10 Oct 2025
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"Take your brother and don't look back"
Series
- Part 9 of SPN 2025 Inktober Drabbles
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Exactly what it sounds like. Hurt and comfort stand alones. Cannon compliant. No smut, no slash, no bashing. Just brotherly love, concern and comfort. Prompts accepted. Sometimes they are episode tags, other times I'm freewriting bashed on my prompts. Every chapter is it's own prompt and can be read on it's own
Series
- Part 1 of Brothers On A Road Trip
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Dean is in Heaven, living out his days with little worry in his own home with his friends.
Castiel is back from the empty, saved by Jack, and installed as the commander of a dwindling angel garrison.
Sam is alive, married with his first child on the way. A young boy he plans on naming after his brother to keep his memory alive. He has retired from hunting.
When a Norse Goddess, Freyja, manages to gain access to heaven she has a proposal for Dean and Castiel. Regain their lives by helping her stop Ragnarok, a coming apocalypse that could wipe out the universe, or spend the rest of eternity suffering in hell and the empty.
Seeing they have no choice, they help her. But as they start to work on the case, not everything is as it seems.
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“Tell Me That You’re Okay, and I’m Fine.” by DestielIsCanonToMe
Fandoms: Supernatural (TV 2005)
07 Oct 2025
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When a routine hunt ends with Castiel trapped under Naomi’s control again, Dean finds himself locked in a narrow elevator with the one person he trusts most — and the one person who’s been turned against him.
As Naomi uses Castiel’s body to dig into Dean’s deepest insecurities, both of them are forced to confront the truth about what they mean to each other, and how far they’re willing to go to protect it.(Or: Dean Winchester gets pinned, bruised, and broken open — not by fists, but by words that sound too much like the truth.)
No. 7: “Tell me that you’re okay, and I’m fine.”
Trapped with the Enemy | Elevator | Pushed Beyond Breaking PointSeries
- Part 7 of Whumptober 2025
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Dean is caught in a demon’s enchanted net, pinned to the wall and straining against magical bindings that cut into his skin. Every muscle screams, every breath burns, and panic claws up his throat. Cas can’t free him directly—but with steady hands and careful guidance, he holds Dean in place, grounding him until the trap releases.
No. 6: “No grave can hold my body down.”
Caught in a Net | Medical Restraints | Pinned to the WallSeries
- Part 6 of Whumptober 2025
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Hell wants its king. Dean wants his brother. And somewhere between the two, an angel is willing to burn the world to keep them both alive.
Series
- Part 2 of The Throne and the Shadow
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Dean wakes in the bunker, drenched in sweat and shaking, face down on the carpet as panic claws through him. His buried-alive phobia, triggered by years-old trauma from Hell, has him gasping and quivering. Cas stays by his side, grounding him with patience and quiet presence, while Dean slowly learns that he’s safe—and not alone.
No. 5: “My panic’s at the ceiling, but I’m face down on the carpet.”
Quivering | Dream Journal | PhobiaSeries
- Part 5 of Whumptober 2025