1 - 20 of 786 Works in Kinky Dean Winchester
Navigation
Listing Works
-
Tags
Summary
Kinktober 2025:
Chapter 1. Dean and Cas get dirty in the garden
(orgasm control [first time writing that!], finger sucking, outdoor sex) -
Tags
Summary
Devil walks the earth and the apocalypse has started. Both heaven and hell have been messing with the Winchester’s heads, and Sam and Dean don't know if they can trust this woman claiming to be the Winchester Oracle.
Worse, it's not clear if knowing the future can actually help them escape their fates. Is Prophecy a noose that can be slipped? Or will Sam and Dean be caught in the cruel trap of destiny?
This is a friends to lovers story with lots of twists and turns set in a universe nearly exactly like the one we know. Season 5, Baby!
(This is a supernatural rewrite with added girl and romance. I don’t know why I started this anymore, but I am committed. This is a Sam forward slow burn, spicy m/f romance, though all characters get love. Dean is also now in a slow burn with Castiel. This story follows the cannon plot of SPN. This is absolutely an indulgent Mary Sue work. But don't we all need to be a Mary Sue occasionally? Come and hang out.)
Series
- Part 4 of The Winchester Oracle
-
Tags
Summary
When Sam gets all the glory from their latest rescued damsel in distress, Dean gets grumpy. Luckily, Sam knows how to turn Dean's frown upside down.
-
KINKTOBER/DAY1/INCEST_MASTURBATION_ORGASMCONTROL/WINCEST by mybloodycavity
Fandoms: Supernatural (TV 2005)
06 Oct 2025
Tags
Summary
How do the Winchester boys pleasure themselves in their cramped motel rooms? Masturbation is a given, and rubbing a quick one out during the times far and few between in which the two strangely erotically codependent brothers are apart, isn’t very feasible. Dean can’t really reach his full climax on mute, so he tells Sam to stop by the library, do some research over there, or something, just to get him out of his hair. Sam, being so inquisitive, just can’t leave without knowing what Dean gets up to, and he learns something about his big brother.
Those dirty, dirty boys.
Series
-
Tags
Summary
Dean plans a quiet date night for himself and Castiel. Castiel can't help but shower him with affection.
Series
- Part 6 of Kinktober 2025
- Part 5 of Kinktober 2025 same canon
-
Tags
Summary
Ever since his mother died, Dean Winchester’s world has been one of revenge and violence. His father, a well renowned bounty hunter, made it his personal mission to kill the man responsible. However, now that Sam is 18, he gives Dean a new mission. Protect your brother at college. So now, the 2 brothers take on Stanford.
Castiel’s family is one of prestige and wealth. But beneath the fanciful exterior lies a secret dark side. Are they basically the mafia? No one is really certain. Known as the “Angel of Death,” Castiel is the best assassin in his family. For the past 3 years, he’s been mostly out of commission, finishing his degree at Stanford, like his father wanted him too. How crazy could his last year get? -
Tags
Summary
Dean: Hey, Sammy. Missin’ you. Check these out. Hurry home, yeah?
Attached were two files: an image and a video. Sam’s pulse quickened. He shouldn’t open them here, not in the middle of class with fifty other students around him, but the temptation was a living thing, clawing at his restraint. He adjusted his position, angling the phone so the screen was hidden from prying eyes, and tapped the image first.
The photo loaded, and Sam’s breath caught in his throat. Dean was in a jacuzzi, the water bubbling around his broad, muscular frame. But it wasn’t the setting that made Sam’s mouth go dry—it was Dean’s ass.
-
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.
-
Tags
Summary
probably my longest kinktober one-shot so far 😭
another favourite fandom of mine🙂↕️ christ this kinktober has some variety.
we have bottom dean winchester chat!! crying his pretty eyes out!! destiel for life raahh
lmk if supernatural is a random we want to see more of 😋 enjoy!!
Series
- Part 5 of KINKTOBER 2025!!
-
Seeing Through the Webcam and Into His Soul (Day 5, Prompt 8) by the-gaudiest-of-vpns (3emo5you)
Fandoms: Supernatural (TV 2005)
05 Oct 2025
Tags
Summary
Dean is on a case but Cas can't wait, so they try something new. All is going well until the insecurities start to drift in.
Series
-
Tags
Summary
Castiel Novak is a priest who essentially hates his life and is riddled with horrendous nightmares.
One night, to ease the pain, he stumbles to the Chapel and comes across a creature that just might make his restless nights easier, or might just calm his nerves forevermore.･*:.｡.
Dean is a blood-hungry beast, roaming the streets, while narrowly avoiding the many police trying to locate who is behind all the strange deaths culminating in Lawrence.
One night, to ease his hunger, he stumbles into what appears to be a tiny church (?) and meets a man looking at him with just as much hunger as he feels in his own rattling bones. -
Tags
Summary
Castiel uses a remote control vibrator on Dean
-
Tags
Summary
Dean and Castiel experiment with some new toys. Dean finds out Castiel thinks he's beautiful when he cries.
Series
- Part 5 of Kinktober 2025
- Part 4 of Kinktober 2025 same canon
-
Sweet Bark, Sweeter Bite (Day 3, Prompt 23) by the-gaudiest-of-vpns (3emo5you)
Fandoms: Supernatural (TV 2005)
03 Oct 2025
Tags
Summary
Cas just can't get enough of the taste of Dean, and Dean can't get enough of Cas taking a taste.
Series
-
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 gets frustrated when he doesn't get much alone time with Cas; it had been thirteen days since they had last had sex. So Dean makes the time, and to his surprise, Castiel brings his wings out to play.
Series
- Part 2 of Kinktober 2025
-
Tags
Summary
Dean drunkenly asks Castiel if he can make him come with "angel mojo". They decide to give it a try.
Series
- Part 1 of Kinktober 2025
- Part 1 of Kinktober 2025 same canon
-
Tags
Summary
Dean's an expert at eating ass. Sam wants the chance just once to reciprocate.
-
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
-
Tags
Summary
Every time Dean had been on his knees for Cas, someone's life was on the line. Every time he had gazed up at him, lips parted and eyes pleading, their relationship just grew more and more complicated.
This time, however, was different. Pleasure rushed through his veins instead of pain, his eyes shined with unshed tears that stemmed from euphoria rather than grief, his lips that were once swollen from unforgiving hits were now plump and red from rough and unyielding kisses. Being on his knees for Cas, like this, was deliciously uncomplicated.
Dean had never considered himself a worshipful man, but being on his knees in front of a flushed and wanting Cas might just be what changes his mind.
Series
- Part 2 of You're My Religion