1 - 20 of 383 Works in Dean Winchester Has Self-Esteem Issues
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After Charlie's death, Dean can barely stand to even look at Sam. Fearing how dangerous he's becoming as the mark on his arm weaponises his grief and anger, Dean opts to shut himself away in Cain's house, with Castiel his only link to the world.
But Castiel discovers that he can do more than just bring Dean supplies and weather his increasingly bad moods. His touch, it turns out, brings with it the mark-numbing effect of angel grace. With this treatment, Dean can feel something other than pain and rage again.
What he feels for Castiel, though... that scares him almost as much as the mark does.Fair warning that I made the unfathomable choice to write this in 2nd person. I don't know why. I actually do think it works for the fic, though, so I encourage you to give it a try and let me know if you agree!
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Do you really love me that much? by iMiss2012fandomVibes
Fandoms: Supernatural (TV 2005)
29 Oct 2025
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"I just want to love on you," you murmured.
You took one of his hands and lifted it to press a kiss to his pulse point.
“I… baby- You already love on me all the damn time," he said nervously.
You kissed his wrist again, and his breath hitched.
“But you don’t let me do it as much as I want to,” you said. “Let me? Please?”AKA Dean is so used to giving, he almost doesn't know how to receive.
Kinktober Day 29: Body Worship
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- Part 10 of Kinktober 2025 (Supernatural)
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“Dean,” A low voice echoed from behind him, “wonderful to make your acquaintance. We’re very excited to have you join us, as i’m sure you’ve already heard.”
Dean turned around to find that the deep rumbling voice came from a handsome, rain-drenched man in a trench coat.
“T-thank you, I’m excited to be here,” He said, trying to catch the name on the man's ID badge attached to a bee lanyard around his neck.
“My name is Castiel,” He stepped forward, stretching a hand out to Dean, “-but the kids call me Mr.Novak.” Dean met his hand where it was extended, returning the man's strong and sure grip. His striking blue eyes stared deeply into Dean's, so intensely that Dean had to break the contact and swallow.
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Dean is starting a new job as a special education classroom assistant,t and he immediately takes a liking to the teacher he's working for, Castiel Novak. The two become friends outside of work, and navigate trying to figure out if the other feels the same way. Castiel brings with him a world of Dominance and Submission, one Dean has yet to experience. Dean needs to handle his father, an abusive alcoholic set on ruining his life.
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Dean's latest ill-advised bar hookup turns him into a werewolf. Contrite and resigned, he goes to Sam and begs him to kill him. No way is he becoming the very thing he hunts. But Sam refuses. Instead, Sam helps Dean through his cycles, and helps him stay off of human flesh. The problem is that his new wolf instincts are driving him towards an even more profound bond than he already has with his brother.
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Dean managed to hide that he was an omega from his father for longer than he'd imagined. It was all going great until he caught him with another omega and kicked him out to the streets.
He goes to live with his mom and his younger brother now, and can't help but think that his time here will be one beige and boring chapter of his life that he'll need to endure until he has enough money to get out.
A certain blue eyed omega meets him in church, and changes his mind completely.
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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 looks at him, his expression gentle, almost human.
“Your freckles,” he continues, “are like stars. I wanted to be sure I didn’t lose a single one.”
Dean swallows, his voice breaking around a crooked grin.
“You’re such a sap, Cas.”
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Suptober 2025
Prompt for day 16: Freckles
Series
- Part 16 of Suptober 2025
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Just Because by castiels_golden_chariot (cleverunseenviper)
Fandoms: Supernatural (TV 2005)
04 Oct 2025
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Months of hard work have amounted to something beautiful. Dean finally feels proud enough to share it.
Series
- Part 3 of Suptober 2025
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A taste of stars and stormy night by silver stake through the heart (Dusk_Sky)
Fandoms: Supernatural (TV 2005)
28 Sep 2025
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“Your offer. Does it still stand?”
“My... offer?”
“That day, before Raphael. You offered me... I changed my mind.”
Dean should tell Cas it’s not the answer. If he was less selfish, he would. But... isn’t Cas allowed to make that kind of mistake after thousands of years being a perfect soldier and a dutiful son? After having believed even when the whole world turned their back on his dad?
Dean longs to be this mistake. He’d be nice about it.
(It’s the only way he can have him... and it’s okay.)
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Summary: the amulet is very powerful. It is faith. Not faith in God, but Sam's faith in Dean.
After Dean tosses it away, Sam starts losing his memories of Dean.
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Dean never expected much from life beyond the Roadhouse, his sketchbook, and the company of nature. Then a stranger with piercing blue eyes steps in one night, and nothing feels the same again. Castiel Novak is powerful, strong and far too interested in an Omega who’s used to being overlooked. From crowded bars to green parks, and through family and love, Dean learns that sometimes the right Alpha doesn’t just notice you—he changes everything.
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Gone either way (and kicked on the way down) by skrongly_Bastard
Fandoms: Supernatural (TV 2005)
19 Sep 2025
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Dean's life can be separated from the before and after in his life. Before, he was free, he wasn't chained down by his secondary gender. After, he was an Omega who disappointed his dad because of his secondary gender. One whose father sold him to the alpha Alistair when he got too far in debt. After a fight with John, Dean packed up everything, stole the Impala and left without looking back. It fine, really, only a blue eyes alpha at the bar he goes to one night seems to know both John and Alistair, neither of which he holds in high regards.
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Dean has to break at some point and he does. Sam tries his best but will it be enough?
Series
- Part 3 of Sunshine Caught in the Rain
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Dad stopped renting from people after this event, from then on it was strictly motels. "Can't risk you misbehaving again." But, yes, back in the day they'd rent from families and boarding houses. It would have been less lonely for Sam he supposes, too late, he messed up. This is what happened at the cobbler's house.
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After the fall of angels, Castiel lost everything, his grace, his wings, and the only home he ever knew. Now painfully human, he's left alone searching for the one person who might still matter: Dean Winchester.
But Dean doesn't want to be found yet. Left alone in the bunker after Sam moves out, Dean drowns in silence, guilt, and memories he refuses to face, especially the ones about Cas.
When they find eachother, their reunion isn’t the salvation either of them imagined. And when an old ghost from Dean’s past returns, it turns out he's not here to heal wounds, he's here to open them.
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Dean has learned lore originating from all over the world. Myths aren’t myths if you find out they’re true. And Dean can’t seem to stop finding his little brother in them.
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Dean loves his little brother and would do anything for him. A story told in parts set in childhood.
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You’re eleven years old and your arm aches as you watch Sammy’s be encased in plaster.
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Dean has a panic attack when Cas disappears on a hunt. When Cas returns, he finds Dean curled up on the floor. Cas hushes him, pressing his grace gently against Dean's chest until he calms.
WRITER SUCKS AT WRITING SUMMARIES!
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It’s not like Dean hasn’t seen the bottom of a bottle before. Honestly, he ends up there more often than he’d like to admit. It’s different now, though. All the liquor in the world can’t get rid of the excruciating awareness that the mark of cain is situated on his arm. He can feel it throbbing under his skin, begging for the attached hands to draw blood. But at least when he’s drunk the urge isn’t quite so strong.
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The Honor of a Herald by blackhorsedances
Fandoms: Supernatural (TV 2005), Valdemar Series - Mercedes Lackey
06 Aug 2025
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Dean really wanted to be a Herald but didn’t believe he deserved the honor. Now here he is with a Companion (A magic horse that talks in his head, and how cool is that?), and the ability to hear anyone’s thoughts and predict the future (sort of). Then he meets a hot guy. Well, the guy breaks his nose and is ready to pound him into the dirt when his Companion Chevvie, and this other Companion, Seraph, show up and start yelling.
Cas wanted to be a gardener, but his father wanted him to get married. Destiny, in the form of snarky Companion Seraph, barged into his engagement dinner and changed that. Then he meets a gorgeous man, and after a rocky start, they become friends and then lovers.
As the magic storms that threaten Valdemar and the surrounding countries increase, so does the activity of a drug-smuggling and human trafficking ring. Dean, because of his skills as a hunter and his Heraldic Gifts of Mindspeech and Foreseeing, is asked to go undercover and get proof and names, so that the bad guys can be brought to justice. There’s just one problem: to save lives–a lot of lives–he has to lie to Cas.
Is their love strong enough to survive the lies, the storms, and Dean’s word of honor as a Herald?
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PROMPT FIC: "Dean Winchester is definitely straight. At least, that’s what he keeps telling himself when he agrees to help Eileen — his brother Sam’s deaf wife — run a kissing booth at the local carnival. The fundraiser benefits a school for deaf kids, and Dean can’t say no when she signs him up as the main attraction. One kiss, five dollars. All for a good cause.
Enter Castiel Novak: quiet, intense, brooding… and Dean’s next-door neighbor. Cas is openly gay, always a little too unreadable, and always just a little too close. Dean swears he’s just being neighborly. Sam swears Dean is an idiot.
So when Castiel sees Dean sitting at the booth, looking uncomfortable and a little pink in the cheeks, Cas just licks his lips — slow, deliberate — and steps into line.
Dean sees him. Swallows hard. And maybe, maybe, starts to wonder if five bucks is really all it costs to learn something he hasn’t let himself ask. 💚💙"
Prompt by Polishmom6521 in Destiel Forever