20 Works in Self-Deprecating Dean Winchester
Listing Works
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Dean mourns Castiel in the only way he knows how; sitting vigil beside his body until he can't bear to look at him anymore
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- Part 27 of Kayden's Whumptober 2025
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Dean has to break at some point and he does. Sam tries his best but will it be enough?
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- Part 3 of Sunshine Caught in the Rain
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I’m Losing Myself in the Mirror, Darling. Don't You See? by serrawn
Fandoms: Supernatural (TV 2005)
05 Jul 2025
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Dean Winchester-Novak keeps the floors spotless, the laundry folded, the smile rehearsed. That’s what perfect omegas do. That’s how they stay wanted.
He calls it love—this routine, this silence, this ache tucked under perfect sheets. But something inside him is unraveling, and no matter how tightly he grips the edges, it keeps slipping through.
Castiel Novak, his alpha, sees the cracks. Tries to reach through them. But Dean has built walls out of obedience and fear, and even love can bruise when it knocks too hard.
Maybe healing is possible.
Maybe not.
Some people break loud.
But Dean is breaking quietly.Series
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The one where Dean Winchester, a thirty-something years old mechanic, discovers, for better or for worse, that those old tales about an angel and a demon sitting on your shoulders, messing with your choices, were actually real all along.
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After months of bad coping mechanisms, John finds out about Dean's self-harm.
Years later, so does Sam.
Eventually, Castiel does, too.
Series
- Part 2 of Sunshine Caught in the Rain
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As Dean struggles to bear the Mark of Cain, Katrina seems to have a grounding effect... but Dean worries at what cost
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- Part 5 of Long Winding Roads
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Season 15 finale never happened and Jack brings Cas back from the Empty.
Jack smiled. “Take him.”
The little wings had sagged. One of them flapped and twitched and then fell limp again. And then they both disappeared.
“Bye bye wings,” said Jack to the tiny Cas. “He’ll learn to control that soon. Take him, Dean.”
Dean found himself with two arms full of little boy. Little angel. He was wrapped in Cas’s trenchcoat. He looked up at Dean with clear blue eyes. And he smiled.
“Dean! Heyo, Dean!”
All of the circuits in Dean’s brain shorted out completely.
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Sam might be immune to the demon virus, but he’s still convinced Dean shouldn’t have stayed with him. The conviction prompts an argument, which turns into a fight, which turns into something else—something long suppressed getting out into the light at last.
It’s not a tender thing, but then again, neither are the two of them.
Missing scene from S02EP09 Croatoan.
Series
- Part 4 of Meta's Wincest Fics
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Standing in a relatively open part of the trail was a sasquatch. The moon hit him like a spotlight, illuminating every wiry hair from the crown of his head to his ankles. Beneath his hairs, stoic muscles kept the creature motionless. He wasn’t nearly as tall as Dean had thought he would be, but he was still massive. And he was naked. Very obviously naked.
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Dean has been looking after Cas's daughter for three years now and loves her as his own. In a fit of anger, she claims Dean isn't her real Dad, and it nearly breaks him. Cas comes home to comfort his daughter and his lover, bringing them closer together than ever.
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Dean thinks that his brother wouldn't save him like he would do for him. This makes his thoughts run wild and only think of the worst things he can.
What path will this lead the older brother down?
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Dean Winchester has defeated Amara and the Darkness that came with her, but not without some injuries. Left disabled, unable to hunt, he spends his time in the bunker, trying to avoid Castiel who is only worrying more and more as the days go on. Castiel has devoted his time to pushing Dean out of his comfort zone and has taken on the task of remind Dean he is worthy again. After a decade of pining and queer baiting- Destiel is now Canon!
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"Truth is, he’s winging it and faking it and hoping he makes it. If there was anything he could do to take back everything that culminated in the most important person in his life feeling like he’s not even on a "loved ones" list, he would, in a heartbeat. But they haven’t exactly made a card that read “Sorry I repeatedly left you and betrayed you and mistreated you, I do totally love you tho”. Distantly, Sam wonders if he’s the only human being on the planet to have fucked up this badly this way before, and sincerely hopes so."
Dean gets hit with a truth spell, at a moment where both lies and honesty have shaken his and Sam's relationship to the point neither feels safe and secure in their bond as brothers, let alone lovers. Will a dead witch with a chip on her shoulder succeed in breaking apart what neither heaven nor hell could separate?
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Dean has lived under the pretence of being a switch since he presented as a teen twenty years ago. He gets by, but his body makes ignoring his true designation harder and harder the older he becomes.
Enter Castiel, a dom so different to everyone Dean has ever been with. Can he help him embrace his submissive side in a healthy way?
Series
- Part 1 of The Decision series
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Dean should have told his dom that he was feeling under the weather in the morning. But he didn't, and now he's dropping with Castiel still on his commute home.
[Can be read as a stand-alone.]
Series
- Part 61 of Destiel <10k Collection (smut-free)
- Part 2 of The Decision series
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Y/N and Dean are planning their wedding, but a reminder from the past gives him doubts about his relationship and whether he’ll ever actually be good enough for her.
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- Part 7 of Life's Lessons Saga
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Y/N’s family is coming to Lawrence to visit her, making this the perfect opportunity for Dean to meet them. Despite his nerves, Dean knows he has to bite the bullet and take the next step in order to have the future he wants with Y/N.
A time stamp in the Life's Lessons Saga
Square Filled: Handjobs
Created for SPNKinkBingo
Series
- Part 3 of Life's Lessons Saga
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Maintaining the facade of a normal life while hunting was harder than Dean had imagined.
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Prompt from the FB group Destiel Forever by Nayna :
I need a fic where Cas is openly bi and constantly flirts with the captain of the football team, Dean . Dean always shuts him off and tells him to stop but Cas keeps trying his luck. One day Dean insults Cas infront of the whole school which breaks Castiel’s heart and from that day he just stops. He doesn’t even look at Dean’s way anymore. Dean should be happy about this but it bothers him way too much now and he kinda misses all the flirting even tho he’ll never admit it...
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Guilt gnawed its way into Dean’s stomach, twisting up inside it, and consuming him. His fingers clenched around the Impala’s steering wheel so tightly that it hurt, and his foot pressed down on the gas petal sharply, moving the car along at speeds far past unsafe and that maxed out the old car’s capabilities. Not again. Never again.
Dean could not—would not let Cas be hurt or die again. Not ever and especially not for him.
10x23 coda