1 - 20 of 743 Works in Soft Dean Winchester
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You're on a long hunt with Sam and Dean, and Dean's been acting strangely. You can't quite put your finger on it...
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They’ve been texting for weeks and Cas is more than ready to meet in person. Until Dean tries to cancel their date because of insubstantial reasons like not having time to go home to clean up after work. Cas considers it very much a non-issue. Even more so when Dean turns up looking… like that.
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Max just needed out.
Dean just needed a reason to run.
A car. A road trip. Two people pretending not to fall apart.He’s trying not to ruin it.
She’s trying not to beg.Slow burn Dean x OC, with grief, guilt, filth, and everything Dean is not allowed to want.
If you want Dean Winchester wrecked and reverent, you're in the right place ;) -
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Castiel is back, but broken—silent and unreachable, even to Jack. When Dean enters his dreamscape, he faces Cas’s trauma, the Empty’s lies, and his own regrets. To bring Cas back, Dean must battle not only the darkness but the weight of everything he left unsaid.
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When Dean comes home from work he finds his neighbor Cas and a baby, both upset and crying, waiting for him.
Cas's sister died in an accident, leaving little Claire in his care. It's a good thing his neighbor Dean knows a thing or 2 about babies because Cas has no idea what he's doing.
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You are a psychic medium that decided to team up with the Winchester brothers on a hunt, only to find yourself adopted into the group. Things are good, until your heart starts to misbehave.
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Crowley always has a trick up his sleeve and the Winchesters always have a demon on their trail, so when they not only open the Gates of Hell and let Lucifer out his cage, killing a surprisingly beloved demon, they end up with an unexpected enemy, Zanora, Crowley's daughter. But when Sam and Dean realize the importance of Zanora's existence, they must decide whether she can be trusted or if she is just as cunning as her father.
- Language:
- English
- Words:
- 2,737
- Chapters:
- 1/?
- Kudos:
- 1
- Hits:
- 21
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One night, when the Winchesters show up on Bobby Singer's doorstep, Dean gets confronted with the harsh reality of his father's disapproval when the latter finds out about Dean's obvious feelings for you.
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Here we go again folks, Suptober 2024. We're back with a whole new list of prompts by the amazing Wigglebox!
Series
- Part 4 of Suptober Challenges
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Dean never had many choices, but he never wanted many, either. He would have chosen this, anyway.
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Dean's on his way to a motel for the night, and he's exhausted as hell. Truly, he's barely staying awake, and in a moment of distraction, he runs over someone. He's quick to get out of the car and check on whoever he just hit, but shock hits him when he realizes that he knows this person. They were once good friends.
The guy has changed a lot in the years they've spent apart, but Dean instantly recognizes the height, the peculiar clothing style, and, of course, the incredibly sharp yet delicate facial features that the Winchester barely ever sees in other people. Dean manages to convince the man to be his friend again, but he's dodgy and on edge and doesn't speak much. Clearly, Dean's old friend isn't exactly what he was as a teenager, but Dean wants them to be close again, and maybe they'll be more than what that they used to be.
But when Dean finds out that his old friend is a supernatural creature — a monster — a conflict arises, along with a lifetime of past hurt and trauma that the tall man has never vocalized.
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True Colors Shine In Darkness (And In Secrecy) by mr_fybraghbty
Fandoms: Supernatural (TV 2005)
01 Sep 2025
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Cas swallows again, selfishly holding a bit tighter around the hunter as he mumbles, “I’m just worried about Jack,”.
Lie, Dean detects immediately. He can tell that it’s a lie. He just came in and found Cas crying with the page about himself—that Dean earnestly wrote—in the Bestiary open on the table; what the hell would Jack have to do with that?
Dean next speaks with a gentle suspicion in his voice, sounding not like he’s accusing the angel but instead like he’s opening the floor for him to tell the truth without judgment. “That’s all?” he says softly, voice comforting and familiar by Cas’s ear.
“...Yeah,” Cas says, lying again.
(TLDR: Cas dealing with his secret of the Empty deal, until he can't anymore. Lots of angsty hurt/comfort, tears, feels, and softness.)
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Castiel feels deeply connected to music — as a Cherubim, later turned Seraph, praising the Lord came naturally to him.
However, there’s a different kind of music he learns to appreciate more each second more. The way human music reaches him makes him yearn for the comfort of it every time he’s away.
Dean learns about this side of Castiel, and he’s eager to see it more.
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Dean finds more of Cas's sketches.
When Dean brings one of the drawings to Cas, the truth slips out in pencil lines and soft confessions: love that’s been there for years, sketched in silence long before either of them knew how to say it out loud.
Series
- Part 5 of Something Just Like This
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The End Is Nigh… Please Proceed to Checkout by icouldgowithyou
Fandoms: Supernatural (TV 2005)
22 Aug 2025
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Another day as a demon, another apocalypse to prepare for. Unfortunately for Dean, instead of racking up more crossroad deals, he’s stuck at Costco with a shopping list as long as his leg.
It should be the most boring task ever – and it is, until he bumps into one extremely intense angel in the toiletry section. A tug-of-war over toilet paper spirals into something neither Heaven nor Hell could have prepared for… and Dean gets the sinking feeling that the end of the world isn’t the only thing about to get complicated.
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Sam is so unstable. His self-harm gets worse and Dean notices, and it comes to a head one day. Sam can't be fixed.
(This is a part two in a series.)Series
- Part 2 of weirdcest sammy sh
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Cas opens his mouth to speak as soon as he watches the younger Winchester hold the kitten up towards his face to look at it up-close, immediately warning, “Sam, wait, that's—”
“Ow!” Sam startles, pulling the kitten away from his face right as Cas sighs out the word, “—Dean,” to finish his sentence.
“He scratched me!” the younger accuses in shock, lifting his free hand to hold overtop the small scratch on his cheek.
(TLDR: Dean gets cursed into a kitten for 24 hours. He's obviously not the happiest about it...but it does give the typically guarded, gruff man an excuse to finally be as affectionate as he pleases. Chaos and fluffiness ensue.)
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all lights turned off can be turned on by clementine_emeralds for Xyyz22, pRawn_eateR
Fandoms: Supernatural (TV 2005)
03 Aug 2025
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A figure was tucked into the corner, murmuring incoherent things. Dean could have sworn he heard his own name amongst the nonsensical ramblings. He shone his flashlight on the moving silhouette, tense and trembling. Dean's shoulders dropped immediately. There was his trenchcoated friend, knelt against the wall, staring at his hands, darkened by..by something. His face was slick with blood, fingers bent in all the wrong angles. Simply breathing audibly rustled his ribs. Dean could tell something terrible happened.
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Dean finds Cas after months of absence—brainwashed, mind controlled, and injured.
August of Whump Prompts: brainwashing (day one), mind control (day twelve), found (day twenty-five)
Series
- Part 6 of a cruel, cruel, capricious god
- Part 1 of Supernatural August of Whump 2025
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I Didn’t Know It Needed Fixing Until It Broke by blueeyedseraphim
Fandoms: Supernatural (TV 2005)
03 Aug 2025
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Castiel shows up with a deathtrap on wheels and a blinking light he’s convinced is an “oil genie.” Dean’s not sure what’s more terrifying — the state of the truck or the fact that Cas has been driving it like that for months. But as the two of them get elbow-deep in oil and engine grease, it starts to feel suspiciously like a date. A very, very messy one.
But this truck is basically Castiels only possession, so, obviously Dean is helping.
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Can Your Love Make the Withered Flowers in My Heart Bloom? by serrawn
Fandoms: Supernatural (TV 2005)
02 Aug 2025
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Dean Winchester is a single mom, café owner, and the center of his daughter Claire’s small but steady world. He bakes like it’s therapy and loves like it’s war—especially after everything Lisa left behind.
Castiel Novak is a philosophy teacher, a single dad to Emma, and the kind of Alpha who makes Dean forget how to breathe. Gentle, steady, infuriatingly handsome—he shows up like clockwork, and somehow always sees too much.
Their daughters are already dreaming of endgame. But ghosts don’t stay buried, and Lisa’s shadow still knows where to find them.
Can Dean and Cas build something real—or will old wounds tear it apart before it begins?
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