1 - 20 of 1,709 Bookmarked Items in Jealous Dean Winchester
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Dean is beyond tired of having to sit back and watch people fearlessly do what he doesn't have the nerve to do: flirt with Castiel.
Jealous Dean is jealous.Series
- Part 11 of 100 Ways to Say 'I Love You'
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It's the weekend before valentine's day and Dean has taken Castiel to a fancy cocktail bar as part of their date. Only some upstart little barboy is hitting on his boyfriend and offering him a 'Screaming Orgasm'...
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- Part 6 of Kiss Prompts
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Original prompt: Dean is still a hunter, his past is the same, he still became a Demon the same way, still got caught by Sam after his fight with Cole but then the cure didn’t work because he's a Knight of Hell. So while Sam and Cas are off talking about what to do next Crowley frees Dean because they've been fooling around but Dean goes off on his own only to turn up again a few weeks later, coming to Cas' aide when he's being attacked. Dean flirts and jokes that he knows how Cas can thank him. Cas of course gets flustered and Dean leaves with a smirk or a smart-ass comment or something else Dean like. Cas knows that he can't have relations like that with a Demon and especially not Dean, he's best friend but he finds the desire has been awoken in him and he's increasingly powerless to stop himself when Dean teases and flirts and touches him.
Or,
The one where we all carry a few demons inside, some to a larger extent than others.
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FxckingJo's Kinktober Soundtrack by fxckingjo
Fandoms: Supernatural (TV 2005), The Boys (TV 2019), The Last of Us (TV), Superman - All Media Types, Fantastic Four, Marvel Cinematic Universe
26 Nov 2025
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These are all the one-shots/drabbles I wrote for Kinktober on my Tumblr @fxckingjo. Compiled for easy reading. I'm more active on Tumblr, and take requests there ;)
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Brittle and battle-worn, Cas looks at him over coffee one morning and says, "I need to go," and Dean instantly knows that he's not coming back.
He's not really sure how he knows it, but he does. It settles into the pit of his stomach, curling hot and tight like something he instinctively wants to tear out with his bare hands. He takes a breath, and it gets stuck in his throat, hitching there. It hurts, hurts, hurts when he finally exhales.
"Yeah," Dean says, "of course you do," and he nods jerkily as he looks down at his phone. He doesn't say goodbye. He doesn't look up from the screen when Cas gets up and leaves the room. He doesn't finish his coffee, or move for a long time.
By nightfall, Cas is gone.
- Language:
- English
- Words:
- 95,090
- Chapters:
- 10/10
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- 4
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- 1,057
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- 6,307
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- 117,921
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Dean Winchester is dead. For decades, he, along with Castiel and Sam, has led a peaceful afterlife in heaven. He has everything he’s ever wanted: a home, his family and friends surrounding him, and a relationship with Cas—and he’s bored as hell. Until, one day, Chuck escapes heaven’s lock up and begins capturing souls to regain power. To stop him, Jack sends Dean, Cas, and Sam back to Earth. After so long away from hunting, will they be able to once again find their place in the family business?
- Language:
- English
- Words:
- 386,936
- Chapters:
- 20/20
- Collections:
- 3
- Comments:
- 1,251
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- 913
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- 560
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- 56,978
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Sam rolls his eyes, "You practically bend over backwards for Cas, Dean. I once saw you physically threaten a guy just because he 'looked at Castiel a mean way.' And Cas, man, he looks at you like you not only hung the moon, but came up with the concept of having a giant rock revolving the Earth, and then hand drew each constellation to complement that rock."
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When he introduces his quiet, sharp-eyed best friend to his little brother Sam, he doesn’t expect Sam to light up every time Cas is in the room—or for Cas to find it so amusing. What starts as a harmless crush spirals into awkward tension, unexpected jealousy, and Dean finally being forced to face what everyone else already knows: he’s in love with Cas
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Raise the Black by emmbrancsxx0, valleydean (emmbrancsxx0)
Fandoms: Supernatural (TV 2005)
30 Sep 2022
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Nassau, 1717. Captain Dean Winchester of the Impala is a born and raised pirate, committed to disrupting commerce and civility on a global scale. After a battle at sea with the Royal Navy, Dean discovers a stowaway on his ship: Castiel Novak, an officer from Carolina with a secret. As their relationship grows, so does England’s determination to end piracy in the New World. This is the story of how men can become legends and how love can ignite a revolution.
- Language:
- English
- Words:
- 246,531
- Chapters:
- 16/16
- Collections:
- 3
- Comments:
- 974
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- 1,097
- Bookmarks:
- 506
- Hits:
- 39,863
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The Seventh Son of a Seventh Son by iregretsigningupalready
Fandoms: Supernatural (TV 2005), Harry Potter - J. K. Rowling
31 Jan 2023
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Dean Winchester is heading back to Hogwarts for his final year. He's the newly assigned Head Boy, alongside his best friends Charlie, Cas, and Benny. This ought to be the best year of their lives as they go through the final stages of school together.
So why does it feel like the beginning of the end? Why does it feel like Dean's best friend, Castiel, has started making all the wrong choices? Why does it feel like Castiel has completely changed?
Dark times are ahead. Dean can feel it. He can only hope that by the end of the year he hasn't lost everyone he's cared about - most importantly, Cas. He hopes he will never lose Cas.
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Bookmark Notes:
The seventh son
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Cas and Dean are broke college roommates who think a good solution to their money problem is to upload gay amateur porn videos to get some extra cash in to help pay for bills.
Apparently "gay friend fucks straight friend" reels in a lot of money. Who knew?
- Language:
- English
- Words:
- 36,160
- Chapters:
- 11/11
- Collections:
- 1
- Comments:
- 371
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- 3,739
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- 809
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- 62,014
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Bookmark Notes:
Gay x bisexual supremacy 💕
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Bookmark Notes:
90% porn omg. Hot.
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So, Dean’s two favorite people have developed feelings for each other. Great stuff. His little brother and his best friend. What could be better than that.
He probably just needs a little space, to figure out how to – best celebrate, uh, how great this is. Yeah. And hey, it’s not like anybody’s going to miss him.
All he needs now is to find a good hunt …
[With wonderful art by the incredible Threshie!!]
- Language:
- English
- Words:
- 19,804
- Chapters:
- 1/1
- Collections:
- 1
- Comments:
- 29
- Kudos:
- 599
- Bookmarks:
- 110
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- 11,769
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Dean Winchester is an FBI agent living with his high school sweetheart for the past 16 years, and for the past 5 years he has been investigating a serial killer they nicknamed Angel. He’s thankful he has Castiel to go home to every night.
Castiel Novak has been hiding who he truly is from his boyfriend, Dean, for the past 16 years. Everything he does is for the man who holds the key to his heart, the man who he has been obsessed with since he laid eyes on him.
When Dean discovers the true identity of the man he has been hunting, will he be able to arrest him, or will Castiel succeed in getting Dean to join him with a secret captive that has haunted Dean’s dreams since he was four?- Language:
- English
- Words:
- 28,033
- Chapters:
- 9/9
- Collections:
- 1
- Comments:
- 16
- Kudos:
- 72
- Bookmarks:
- 25
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- 1,722
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In the humid haze of Northwest Louisiana, where Creole roots run deep and the bayou whispers forgotten rites, Adrienne Lecompte guards her family’s shadowed legacy—ghosts, hoodoo altars, and blood-bound secrets.
But soulless Alpha Sam Winchester shattered her world two years ago, using her as demon bait and abandoning her to bleed out in the dark.
Now he’s returned, soul intact but feral-edged, alongside his brother Dean—solid, golden, and dangerously attentive. As both Alphas circle her with scents that ignite forbidden instincts, the parish buzzes with old tales: of her ancestor, the Omega who bound an ancient power when two Alpha brothers claimed her in a ritual of bed, bite marks, and bond.
Adrienne feels the pull, the awakening. This isn’t just history repeating—it’s her blood calling it forth, hungry and alive. In a dance of pheromones, mating marks, and Southern Gothic storms, surrender might save them… or devour them all.-
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Dean’s never needed to say much to make a point.
Especially when someone dares to look at Sam like that. -
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Hiatus fic set after the S11 finale. Dean's alive, Sam's alive, they're going to get Cas from wherever he got zapped to, and everything's finally gonna be all right. Dean's on top of the world.
A little voice in the back of his head is whispering "It's never that easy," but Dean ignores it.
- Language:
- English
- Words:
- 352,388
- Chapters:
- 53/53
- Collections:
- 3
- Comments:
- 5,193
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- 7,686
- Bookmarks:
- 2,106
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- 253,202
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Grass is Always Greener by Koraesdoodles
Fandoms: Batman - All Media Types, Supernatural (TV 2005)
26 Jul 2024
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"Jason had already launched himself into the air by the time whatever-that-thing-was latched onto the boy’s leg, nearly yanking it off as it dragged him from hiding.
The kid twisted in the monster’s jaw with surprising dexterity and speed, plunging something into the creature’s throat at short range. Jason couldn’t see what it was, but as soon as the boy pulled back the monster screamed, its entire body writhing in agony before it exploded, knocking Jason out of his trajectory and toward the alley wall. He scrambled to keep himself from being brained on a brick wall, diverting his momentum to spring off the barrier instead of being flattened by it.
“What the hell was that?” Yelling at a traumatized civilian wasn’t very “Robin” of him. Jason needed to keep it together."
Jason Todd wasn't supposed to be patrolling. Sam Winchester wasn't supposed to leave the motel room. But neither of them are great at doing what they're told. Both of their families have a lot of opinions about this.
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Castiel and Dean have been quietly exploring their feelings for a few weeks, keeping it mostly between themselves while still navigating hunts and the road. At a diner in some small town, a stranger flirts openly with Castiel. Dean sees it. Dean feels a mix of irritation, protectiveness, and something deeper. Dean kisses Castiel in the softest, most possessive way possible, leaving everyone else in the diner with no doubt whose angel he is.
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“Oh yeah, there might have been some small details I forgot to mention about the bond,” Gabriel teased.
“What kind of details?” Dean growled uneasily.
“Oh just the Holy Matrimony kind,” Gabriel smirked.
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When Cas's grace is running out for the second time, the Winchester brothers enlist the help of a certain archangel to save his life. Gabriel comes up with the perfect solution: Dean and Cas bond. This seems like a great plan until Dean discovers too late what the bond really means. Gabriel informs him, much to his delight, that he is now Angel Married to Cas with no way of reversal. Little does Dean know, Gabriel is messing with him and the bond isn't a marriage at all. Cue a bunch of embarrassing misunderstandings as Dean struggles with his new "marriage" to Cas.- Language:
- English
- Words:
- 65,047
- Chapters:
- 16/16
- Collections:
- 5
- Comments:
- 595
- Kudos:
- 5,981
- Bookmarks:
- 1,246
- Hits:
- 112,579