1 - 20 of 669 Works in Crying Dean Winchester
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A murder attempt brings Castiel face to face with the most profound form of grief: the loss of a child. A strange man that calls himself Batman scrapes Castiel up off the side of the road and takes him on a journey to find his son — a journey that leads to both of them finding much more than they bargained for.
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Everyone is somehow curious to look death in it's eyes and stare at it, while it prepares it's scythe and cuts of your head. Death might be kind to those who are not afraid and who are prepared to die, but does a person like that even exist? If so, Dean is not that person. The death won't be kind to him. But despite that, he opens his eyes.
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Suptober 2025
Prompt for day 7: Surprise
Series
- Part 7 of Suptober 2025
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Two months. Two months the tension has built up. Both Castiel and Dean are frustrated—they needed this. Bad.
Kinktober 2025: dacryphillia
Series
- Part 1 of Kinktober/Whumptober 2025
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What if Season 15 Episode 20 wasn't the end of everything? What if we were given just one more season? What would happen....
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Cas was taken by the Empty on a Thursday.
Chuck is defeated and freedom awaits Dean, but at what cost? Can Dean survive without Cas, and more importantly, does Dean want to navigate life without his best friend?
There is also the small issue of the fact that ‘He didn’t get to say it back.’
Or: The one where Dean wanders the bunker alone and tries to forget he is still alive.
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Dean hurts Cas with his words. Cas believes Dean meant those words and that Dean regrets their relationship. Now, Dean has to use his words to let Cas see that he doesn't regret anything and that he loves him.
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- Part 3 of Angst/Sad/Comfort Stories of my ships
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"And you’re terrified that making love to a man you actually care about would feel too good to keep ignoring."
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It was Dean’s 12th birthday, and John never called.
It had actually been a good day, Dean reflected as he turned the hot water on in the shower. Bobby’d let him have a few friends over, they had pizza for dinner and an ice cream cake decorated with old cars for dessert; Bobby and Sam had even gotten him a handful of presents—things that didn’t come from the 50 cent bin at the drug store, things he actually wanted—and Dean’d had fun.
But John had never called.
Series
- Part 10 of Sicktember 2025
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Cas comes back to the edge of the bed, a hand outstretched. "Dean?"
"Yeah."
Cas touches him, and he feels that sickening rush of mending, skin growing under fresh scabs. Bone grinds in his chest as a rib shifts minutely—he didn't even realize it was fucking broken. The pink and green hotel room snaps into a disgusting level of focus and he's left with cottonmouth and a faint headache but none of that blanketing drunken numbness, his pain both dragged to the forefront and almost completely diminished.
He jerks away from Cas too late to make a difference. "Fucking hell," he starts, then closes his eyes and takes in a few gasping breaths. This is wrong, he's not ready to stop hurting. This is wrong.Cas returns to their lonely hotel room as Dean is picking up the pieces of a really bad night. Set during season four, when Dean and Sam are on the outs. Content warning for brief but specific references to real-world hate crimes.
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Taking place immediately after the end of The Subway, Dean and Cas randomly run into each other on a subway in New York City for the first time in six years and they decide to take it back to Castiel's apartment and have some sex about it
xxx
can PROBABLY be read without part one but i don't suggest it bc part one is so good and so cute and my literal baby but do whatever you want :))
Series
- Part 2 of the subway verse
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Benny shows Dean a little oasis in purgatory where they can unwind for a moment, free of monsters - and their clothes. What starts as a relaxing bath quickly turns into more and Dean is forced to face his internalized homophobia in a very hands-on approach.
- Language:
- English
- Words:
- 7,373
- Chapters:
- 1/1
- Kudos:
- 9
- Hits:
- 84
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After almost a year of talking online, Dean’s long-distance Dom, a taekwondo instructor, finally talks him into taking up classes at his local dojang. As a result, Dean comes face to face with an instructor that threatens to be his undoing: a strict, cold man that is known simply by his title, Sa Bum Nim — master instructor. Sa Bum Nim makes Dean’s life miserable, as does the ‘interesting’ beta that his long-distance situationship keeps talking about.
Dean’s lived stealth his entire life, especially at the gym where he’d have to get an alpha’s permission to participate otherwise. When his meds fail, his carefully constructed veneer threatens to crack and expose him to the world as the thing he’d been taught to hate about himself. Unwillingly off his meds and doomed to endure his natural cycle, his upcoming heat promises to be intense, and leaves him with precious few options for companionship. When a reluctant call for help brings his two worlds colliding together, he’s unsure he can survive the aftermath: the promise of the dynamic of his dreams and an answer to his prayer for independence within a system designed to keep him at the bottom.
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After four months of devastating silence, meant to protect her from the dangers of the supernatural world, Dean Winchester arrives at his girlfriend's door with wilted flowers and ice cream, ready to attempt to piece together the love he nearly destroyed.
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Castiel Novak and Dean Winchester were lifelong best friends until a wedge was driven between them by Dean's homophobic father.
Now, years later, John is dead, and Dean is divorced. To start his new life, Dean moves miles away to a new town where nobody knows his name. Or so he'd hoped.
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La añoranza de sentir, la maldición de extrañar by Supertitanfan47
Fandoms: Supernatural (TV 2005)
02 Aug 2025
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¿Qué pasaría si Dean intenta marcarse una nueva cicatriz de la mano de Castiel gracias a que no puede sobrellevar el duelo?
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Dean was feeling his heat coming closer. The alpha he usually spent his cycles was nowhere near him, and he was the only werewolf in all Washington DC, so he went to a bar to get some butty, or dick, whatever.
Also, Castiel, one of the only twenty-three vampires in the States, went out for a little snack on tuesday night.
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Hold Your Horses: Cutting Cum by destielcorecore, notreallyaroad
Fandoms: Supernatural (TV 2005)
25 Jul 2025
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John Winchester raised his boys doing two things: scammin’ rich pricks and tuggin’ horse hog. When he dies and leaves his boys penniless and horseless, Dean ultimately follows in his dad’s footsteps by combining his two skill sets in order to pay for Sam's schooling and his burgeoning drug addiction, finding love (and a horse) along the way.
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“One, Bert and Ernie are gay.”
“Two, you are not gonna die a virgin. Not on my watch.”
The words came out sharp. But not harsh. Cas looked up slowly, eyes trailing up his body. Meeting his dark gaze. Dean seemed confident, but there was a flicker of something else in his eyes. The hunter pursed his lips, glancing down at Castiel’s tie for a moment. “Just, uh.. if you do end up living after this. Don’t tell Sammy. I’m just doing a favor for a friend, got it?”
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or, dean gives cas his best line, expecting to be the one doing the fucking, when really he was gonna be the one getting fucked
first fanfic dont kill me its probably sucky sorry
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Castiel Novak didn't expect to lose his virginity to some random guy he met at some random party.
And Dean Winchester certainly didn't expect to ever sleep with a man.
They can’t remember the night things went to shit, but they both know this:
Everything is about to change.
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When Cas loses his job, he brings his rage home. He forgets the fragility of the softhearted omega who waits for him, who always believes in him, who holds their love like something sacred. In one furious moment, Cas breaks something beautiful—and then watches his omega bleed trying to gather the pieces. Now, Cas will do anything to fix what he’s shattered, and hold his mate like he should have from the start.
Series
- Part 16 of Pure S³ energy - Short, Soft & Sweet💕🌸🍓