1 - 20 of 846 Works in Dean Winchester Being an Asshole
Navigation
Listing Works
-
Tags
Summary
Hazel Sinclair's life is built on the quiet things. A library she loves, a second cup of coffee (always), and a wardrobe full of cardigans.
Dean Winchester's life is the opposite. A new town every week, greasy burgers, and more blood on his hands then he knows what to do with.When a slew of disappearnces draws the Winchesters to Everhollow, what begins as a simple case turns into something neither one of them wants to let go of. He is danger wrapped in leather with a smile that could ruin her. She is sunlight, and slow days, and everything he believed he could never have.
But as vengeful spirits rise and old oaths demand to be kept, Hazel and Dean are forced to choose between the lives they’ve always known and the one they never expected to find.
Promises aren't meant to be broken. But some were never meant to be kept.
-
Tags
Summary
Demon Dean hunting Sam in 10x03 but instead of Cas appearing, it ends differently
-
Tags
Summary
A witches curse turns Cas into a child with a spell meant for Sam. Dean makes the worst decision possible trying to protect his brother, but Sam won't stand for it and will do everything he can to save his friend who saved him. Cas!whump
-
Tags
Summary
“We just need time to fix this. We need to go somewhere safe, somewhere where no one can find us.”
After "Jack in the Box" and beginning of "Moriah". Castiel convinced Jack and took him on the run from the Winchesters and the Apocalypse world hunters, who were actively planning to hunt Jack down and kill him.
It wouldn't be easy. Because of all the pain and trauma both had endured. Because both of them had been so isolated, they had no friends and allies left.
But forget all that. The most basic, most urgent threat they faced, if they wanted to start a new life out in the world?
They had no identification papers. -
"The blood flows out like a river" - Kinktober Day 15 (Semi-Public + Object Insertion) by cosmic_caden
Fandoms: Supernatural (TV 2005)
16 Oct 2025
Tags
Summary
Demon Dean decides to kidnap Sam for his own pleasure. Fortunately for him there's a super easy way to get Sammy addicted to his mere existence.
Or: Demon Dean force feeds Sam his own blood so Sam will stay with him foreverSeries
- Part 17 of Kinktober 2025
-
Tags
Summary
Kinktober day 5, prompt is dacryphilia.
Dean became a demon after being killed by Metatron. Castiel just wants to help him turn back human, so when Dean decides to collaborate, the angel is very trusting, perhaps too trusting.
Dean easily leads his best friend into a trap and Castiel has no way out except by surrendering to the demon's will. -
Tags
Summary
Sam and Dean have moved on from the rockiest years of their relationship, only to be wrenched apart again by the best and worst of news- their mother is alive.
Series
- Part 2 of Separated at Death
-
Tags
Summary
Day four of kinktober, prompt is voyeurism.
Endverse, Cas is a human now, but he still likes to watch the fearless leader while he sleeps and if he catches him doing something else... He's not opposed to keep watching.
-
"As we dance to the masochism tango" - Kinktober Day 2 (Kidnaping + Coming Untouched) by cosmic_caden
Fandoms: Supernatural (TV 2005)
02 Oct 2025
Tags
Summary
'Now lets go take a howl at the moon'
Expect Crowley decided to kidnap demon!Dean and tie him up in hell instead. Both of them turn out to be happy with this scenario.
Or: Crowley makes demon!Dean watch as he tortures someoneSeries
- Part 2 of Kinktober 2025
-
So You Remember How It All Went Wrong by swishydetective
Fandoms: Supernatural (TV 2005)
30 Sep 2025
Tags
Summary
The year is 2014, Castiel and Dean are living in Camp Chitaqua and the world is infected with the Croatoan virus. The Apocalypse is here. Castiel, barely an angel, barely human, is reading his journal entries from when it all started to go wrong five years prior and reminiscing on the key moments of his and Dean's relationship.
-
Tags
Summary
"Dean—" Sam began, but dean cut him off.
"No, Sam! This—this took us days to put together, and now it's ruined because of this fucking useless being!" He turned back to cas. "What the hell were you even doing?"
Cas hesitated before answering. "I was researching about... bees."
Dean blinked. "Bees. You were researching about bees instead of fixing the damn papers?"
Cas nodded slowly. Dean let out a humorless laugh, his frustration boiling over. "Get out."
-
Tags
-
Tags
Summary
Awkward and quiet Castiel is working on getting his PHD and living with his older brother Lucifer when he meets someone who changes his whole life. Sam Winchester is the best thing to ever happen to him, but their bliss is interrupted by controlling family members.
-
Tags
Summary
Sam has endured years of Dean's homophobic bullying, slurs cutting deep, while he hides his own desires. But when Sam uncovers Dean's secret side hustle—stripping at a gay club for cash—the tables turn with brutal precision.
-
Tags
- Language:
- English
- Words:
- 280
- Chapters:
- 1/1
- Kudos:
- 2
- Hits:
- 123
-
Tags
Summary
When Dean is a Knight of hell, he happens to create a daughter who is half demon/half human who appears on his front door just a short time later. And she is aware that she is an asshole, but in her defence, she got it from her father.
-
True Colors Shine In Darkness (And In Secrecy) by mr_fybraghbty
Fandoms: Supernatural (TV 2005)
01 Sep 2025
Tags
Summary
Cas swallows again, selfishly holding a bit tighter around the hunter as he mumbles, “I’m just worried about Jack,”.
Lie, Dean detects immediately. He can tell that it’s a lie. He just came in and found Cas crying with the page about himself—that Dean earnestly wrote—in the Bestiary open on the table; what the hell would Jack have to do with that?
Dean next speaks with a gentle suspicion in his voice, sounding not like he’s accusing the angel but instead like he’s opening the floor for him to tell the truth without judgment. “That’s all?” he says softly, voice comforting and familiar by Cas’s ear.
“...Yeah,” Cas says, lying again.
(TLDR: Cas dealing with his secret of the Empty deal, until he can't anymore. Lots of angsty hurt/comfort, tears, feels, and softness.)
-
Tags
Summary
As his nightmares get worse, Dean realizes he’s turning into something he’s terrified of; he needs his girlfriend’s help. The corruption of the Mark of Cain leads to a heart-wrenching promise. Can the curse be lifted or will it leave scars?
Series
- Part 2 of Jacklesverse Bingo 24
-
Tags
Summary
Your life was simple. Ordinary. Lonely.
Until everything changed. Until a monster, straight out of your favorite TV show, attacked you.Turns out, the world you escaped to for comfort... is very real.
***
She wasn’t part of the plan. A stranger who somehow landed in the middle of the Winchesters’ world. But with a past she doesn’t fully understand and a kind of magic they’ve never seen before, she might be the key to more than just surviving the trials ahead. And for Dean, she might be the one thing he never saw coming.Series
- Part 1 of Ordinary
-
Tags
Summary
In S9E6: Heaven Can't Wait, Dean doesn't drop Castiel off at the Gas-n-Sip until the next morning, after the case with the Angel of Mercy, Ephraim. Since Castiel is human, he has to sleep, and so does Dean. So, where do they go during this unexplained amount of time? What were they doing that night, and where did they stay?
This is my version of the events of that night. Explicit content lies within!