1 - 20 of 1,230 Works in Dean Winchester Has Self-Worth Issues
Navigation
Listing Works
-
Tags
Summary
Set somewhere in season 3
I subbed the prompt 'lamb to slaughter' for suicide or rather suicidal because it can't be that sad that quick.
Prompts:
Suicidal | "If my days are numbered, why do I keep counting." -
Tags
Summary
in a quiet pool, devils dwell.
Dean Winchester is twenty-four, living alone in New York while Sam is across the country getting his law degree. He’s working guard shifts at a supermax prison, protecting him from the monsters he’ll prosecute one day. He may teeter on the edge of poverty, but he’s doing everything he’s supposed to. Good, honest work that would make John proud from wherever he fucked off to, pay his bills almost always on time, roof over his head, dinner most nights of the week.
He’s content.
He’s miserable.
He’s bored.
Then he’s put on Krushnic cell watch.
The corruption begins at the mouth, the tongue, the wanting. The first poem in the world is I want to eat.
-
as i looked back upon armageddon i cared only for the moment of truth between you and me by quatru_ruv
Fandoms: Supernatural (TV 2005)
05 Oct 2025
Tags
Summary
this is gonna be a sabriel and destiel slowburn. please trust the process, this chapter is just me laying out the groundwork for the whole plot to plot.
dean drops sammy off to stanford, we find out about their basic everyday lives & friends.
-
Tags
Summary
Dean’s Sunday isn’t a day off—it’s a nesting day. Suppressants, concealment spells, and a lifetime of pretending can’t drown out an omega’s instinct… especially when the only alpha he wants wears a beige trench and a crooked smile...
-
Tags
Summary
When Dean has a year left to live (season 3), he finally decides to write his journal. Maybe someone will find it? Or he struggles with many thoughts every day and hopes that it will help him?
-
Don't tell another soul by silver stake through the heart (Dusk_Sky)
Fandoms: Supernatural (TV 2005)
05 Oct 2025
Tags
Summary
When John died, Dean drove Sam to Bobby so his brother wouldn't end up in the system. Sam seems to dislike his decision, but Dean can't be sure: they aren't talking anymore, despite living in the same place.
Dean's trying to get used to this new life, but it's hard, especially with people bringing back John's memory every now and then. He wants to move on. Is it too much to ask?
His new friend—his very first friend actually—doesn't think so.
Series
- Part 3 of Things change
-
Tags
Summary
i don't believe in god, but i believe that you're my savior
when you live a life that never allows you to understand the existence of home, you start to find it in other places. people, too. dean winchester's home is the driver's side seat of the impala, and always with sam next to him. bunny norton's home is across an ocean, and preferably as far away from dean winchester as possible. when sam asked her all those years ago for her help, she'd come running. but dean makes her wish every day that she hadn't stayed.
slow burn, enemies to lovers. someone's got a thing for priests but i'm not saying who. canon is followed whenever i feel like it, tags will be updated as story progresses. slightly OOC dean in the first few chapters bc i like when the pretty man angry…
-
Tags
Summary
Castiel Novak, a special agent is known for being professional, detached and cold. His world revolves around his job— exhaustion is a criminal he cannort catch.
Dean Winchester is a serial killer. A ghost in the night, he leaves no trace behind and vanishes without a sound.
When Castiel is assigned to the case of "The Hanuted Hunter", he wastes no time. Desperate to catch the monster, Dean Winchester, he runs race against time.
But in the middle of the hunt, stolen kisses in motel rooms, whispered confessions and lingering glances blur the line between hunter and hunted. While the secret remains silent, the two men cannot.
-
Tags
Summary
Updates every Saturday evening!
Dean Winchester is just trying to keep his shit together. Being a firefighter keeps him busy, his friends keep him laughing, and no one asks too many questions.
That is until the day he walks into a little bookstore and meets Castiel, a man who has plenty secrets of his own, and seems just as weird as the shop he runs.
Or: A story about finally letting yourself want more, and trying not to run when it actually shows up.
-
The Shadow Guild, Part I: The Beginning of the End by CreeperSpockJr (1stBorn_RalphSpockJr)
Fandoms: Grimm (TV), Supernatural (TV 2005), The Originals (TV), Teen Wolf (TV), Interview with the Vampire (TV 2022)
04 Oct 2025
Tags
Summary
After one of his friends go missing, Elijah Mikaelson enlists Sam and Dean to track her down. From there, they arrive in the city of Portland, Oregon where they meet Detective Nick Burkhardt.
And from there… well… all hell breaks loose. Again.
Series
- Part 1 of The Shadow Guild
- Part 5 of The Chronicles of Olympia
-
Tags
Summary
5 times Castiel found Dean Winchester’s lace panties where they absolutely should not have been, and 1 time he got to enjoy it in all its glory.
OR
A Laundry AU nobody asked for, featuring: ✨magenta lace✨, ✨Dean in panties✨, ✨Castiel spiraling into a bi crisis✨, and ✨fluorescent lighting that witnesses too much✨.
-
Tags
Summary
Dean Winchester fixes things. Keeps his head down. Follows orders, mostly. Doesn’t ask questions. He can’t afford to, not with a father watching his every move, a brother he’s desperate to protect, and a past sealed behind a NDA.
So when a repair job sends him to a brothel on the edge of town, he tells himself it’s just work. Just another job.
But the android he’s sent to fix doesn’t behave like the others. It looks at him too long. Hesitates before it speaks. And when it touches him, Dean forgets—for a moment—that machines aren’t supposed to feel.
He knows better than to get involved. He does it anyway.
Now he’s tangled in something bigger. Secrets, loyalties, and everything Dean thought he understood about free will and humanity.
He’ll have to decide if being human is about what you’re made of or the choices you make.
Updates every Friday with smaller bonus chapters now and then mid-week!
-
Tags
Summary
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.
-
Tags
Summary
The Bunker's immaculate pantry is Dean Winchester's most sacred ritual (\, a silent guarantee that scarcity will never touch his family again. But when a minor domestic disruption shatters that control, he’s dragged back to the devastating moment he realized his vulnerable charge was a sacrifice in a world with no margin for error.
Series
- Part 1 of Whumptober 2025
-
Tags
Summary
If the universe needs a punching bag, let it be him.
Set during 5x18 Point of No Return, when Dean tries to give himself over to the angels and Cas stops him.
day two + day six prompt fill: taking accountability / pinned to the Wall
Series
- Part 2 of whumptober 2025
-
Tags
Summary
Dean can feel Cas' exhale on his lips and his eyes almost cross. He wants to taste those lips so badly. He feels like a starving man who has been lost in a desert for few days and finally lies his eyes on an oasis. He is starving for them. He is starving for Cas.
Oh.
Oh.
----------------------
Suptober 2025
Prompt for day 1: Pumpkin
Series
- Part 1 of Suptober 2025
-
Tags
Summary
Three weeks ago Dean had his first heat post-Hell which he shared, against the advice of Sam and Bobby, with a certain Angel of the Lord.
Newly mated, Dean and the rest of 'Team Free Will' (along with the help of Heaven) race against the Demon hordes to stop them from breaking the 66 seals meant to keep Lucifer in the cage.
The Biblical Apocalypse looms closer with each day that passes and each seal that's broken.
And if that weren't enough, Angels, Demons, and every other supernatural creature is on the edge of their seat with the news that a Nephilim has come into being. Each side hoping to either kill the abomination or use it to win the war.
Oh, did Dean mention he’s pregnant.
(An Omegaverse Supernatural Rewrite set in Season 4 picking up on "I Know What You Did Last Summer")
WIP: CURRENTLY IN PROGRESS
Series
- Part 3 of Aftercare
-
Please Don’t Be Long, ‘Cause I Want Your Love by saturny27
Fandoms: Supernatural (TV 2005)
29 Sep 2025
Tags
Summary
Some days are harder than others, and now that the world’s not ending, the growing pains are catching up to Dean. He’s not used to allowing people to help — he’s not very good in recognizing he needs help —, but he’s allowed love to come its way, what’s wrong with being vulnerable around his angel?
Or: Cas noticed Dean’s taking too long in the shower.
-
Tags
Summary
Dean Winchester's childhood died in the same fire that killed his mom. With a mean Drunk as a dad and having to take care of Sammy, will he ever get a break?
AS OF SEPT 19TH AND CELEBRATION FOR OVER 1000 HITS, THIS IS GETTING A FEW NEW CHAPTERS AND A SEQUEL STORY THAT WILL COEXIST
-
Tags
Summary
Castiel comes back, human, and suddenly the world feels different. Dean calls him Castiel at first for fun, to mask the weight of everything, but it doesn’t stay a joke. With every repetition, it becomes something else—tender, binding.
OR
A story about finding each other, quiet mornings, stumbling into domesticity, farmer’s markets, paint stains and coffee rings, maybe one last case, and the raw intimacy of learning each other without walls. In small rituals, they discover what it means to live without blood and fear, and to love without it.Or
A quiet love story about humanity, healing, and the way a name can mean everything.or
they get together, kiss, and have filthy sex, too.--
"The first time Dean says his full name, it startles him, deep, hits him like a thunderbolt. His eyes widen before he can stop it, and the word strokes something ancient in him, as old as the last wisps of his grace holding his skin together, and yet, embarrassingly human. It lands somewhere deep in his chest, somewhere to the top of his lungs, igniting him like a dropped match in dry grass. And something—heat or want maybe—flickers to life.
Dean doesn't look away. Then he says it again, slower."