1 - 20 of 102 Works in Desperate Dean Winchester
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Summary
Dean and Cas decide to try the Kama Sutra book they got a few years back.
Or,
The one where their physical abilities are put to the test but it’s all good fun!
Series
- Part 5 of The calendar fics!
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Summary
Dean can suddenly hear Sam’s thoughts after an incident with Crowley. (This is set in season 9 of SPN) Let’s just say he’s not mad about it, snippet:
“I’ve been doing some research, something to do about secrets? Wanting to reveal a secret of some sort?” he was flipping through the pages of the book.
“Here, it says break a bond with a dark secret-“
“Soooo?” Dean drew it out slowly before taking another bigger bite, mayo dripping down his lips.God… my jeans are getting tight, you’re killing me Dean.
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WARNING: VERY EXPLICIT SEXUAL CONTENT THAT PROGRESSIVELY BECOMES DARKER & MORE EXTREME AS THE STORY UNFOLDS. If you’re looking for something light/easy/vanilla/etc., this ain’t it!
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“Sam couldn’t seem to manage to do anything but gasp for air and gaze up at him like he was the damn messiah (fuck…just like that), just the way he wanted.”
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Denial, tension, guilt, confessions and confrontations culminate in the tumultuous beginning of a new kind of relationship for the boys when Sam is seventeen.Keeping their secrets, navigating their sexuality together, deeply-codependent obsession, Dean’s lust for total control and dominance over his little brother, unconditional love, pain, power, and something evil and ancient at their heels that has even Dad scared.
These are just a few of the things in store for Sam and Dean as they hold on tight to the unbreakable bond that’s always connected them, a force of nature ultimately proving stronger than either of them could have ever imagined.
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Many Treats of Anguish and Ecstasy (Day 22, Prompt 28) by the-gaudiest-of-vpns (3emo5you)
Fandoms: Supernatural (TV 2005)
23 Oct 2025
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Summary
Cas decides that Dean deserves a bit of a reward for cleaning the kitchen. Dean isn't sure if it totally counts as a reward.
Series
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Real tough cookie with the whiskey breath by sorryitsmyfirstdayonearth
Fandoms: Supernatural (TV 2005)
23 Oct 2025
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Summary
Dean and you try something new, and his reaction is surprising.
Series
- Part 13 of Sorry's Smutober Spectacular 2025
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Summary
Every secret will swim to the surface and it's only a question of when, not if. And when it does, Castiel won't stop, until he knows every single thing Dean Winchester has been hiding from him.
He doesn't trust him, but he can't say that there isn't something alluring about the man.
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Suptober 2025
Prompt for day 22: Undercover
Series
- Part 22 of Suptober 2025
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Plugged With Pleasure (Day 19, Prompt 15) by the-gaudiest-of-vpns (3emo5you)
Fandoms: Supernatural (TV 2005)
20 Oct 2025
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Summary
Cas' suggestions are starting to get risque, and Dean is reaping the benefits.
Series
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Learning to Ride (Day 13, Prompt 11) by the-gaudiest-of-vpns (3emo5you)
Fandoms: Supernatural (TV 2005)
13 Oct 2025
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Summary
Cas pulls out a new toy and Dean gets quite the wakeup call.
Series
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A Public Solution to a Private Humiliation (Day 12, Prompt 6) by the-gaudiest-of-vpns (3emo5you)
Fandoms: Supernatural (TV 2005)
12 Oct 2025
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Summary
They're both getting pent up waiting for Jack and Sam to give them some alone time, so Cas takes things into his own hands.
Series
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Sweet Bark, Sweeter Bite (Day 3, Prompt 23) by the-gaudiest-of-vpns (3emo5you)
Fandoms: Supernatural (TV 2005)
03 Oct 2025
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Summary
Cas just can't get enough of the taste of Dean, and Dean can't get enough of Cas taking a taste.
Series
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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
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Summary
Dean's on his way to a motel for the night, and he's exhausted as hell. Truly, he's barely staying awake, and in a moment of distraction, he runs over someone. He's quick to get out of the car and check on whoever he just hit, but shock hits him when he realizes that he knows this person. They were once good friends.
The guy has changed a lot in the years they've spent apart, but Dean instantly recognizes the height, the peculiar clothing style, and, of course, the incredibly sharp yet delicate facial features that the Winchester barely ever sees in other people. Dean manages to convince the man to be his friend again, but he's dodgy and on edge and doesn't speak much. Clearly, Dean's old friend isn't exactly what he was as a teenager, but Dean wants them to be close again, and maybe they'll be more than what that they used to be.
But when Dean finds out that his old friend is a supernatural creature — a monster — a conflict arises, along with a lifetime of past hurt and trauma that the tall man has never vocalized.
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Nightmares and panic attacks have been Dean Winchester's constant companions since returning from Hell. Now Dean has to experience his first Heat since being Alastair's mentee on the rack. While Sam attempts to drive Dean to a safe haven, Dean makes an unexpected social call to a certain Angel of the Lord. And... well. Dean has a hard time keeping his hands to himself in the backseat.
I promise it's good. (No Wincest, Sam is not involved in any way other than to be scarred for life)
Series
- Part 1 of Aftercare
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Summary
Castiel Novak and Dean Winchester were lifelong best friends until a wedge was driven between them by Dean's homophobic father.
Now, years later, John is dead, and Dean is divorced. To start his new life, Dean moves miles away to a new town where nobody knows his name. Or so he'd hoped.
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Summary
Dean accidentally gets into some sex chocolate (courtesy of his brother “forgetting” to mention what they were). Thankfully, Sam is off on a solo-mission and Castiel… well, what can he say? He’s only an angel of the lord.
Or
I give you 6.5k words of porn. I hope you are sated.
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Summary
Dean tries to get his brother back after he disappears, and when he does, his brother brings back a stray home.
Series
- Part 10 of Archived Tumblr Fanfictions
- Part 4 of Samboy Chronicles
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After a brutal hunt, Dean’s angry, raw, and too wired to sleep. A motel phonebook and bad impulse control lead him to a midnight sex line. He expects a woman.
Instead, a man answers.
His name is Castiel. His voice is deep, calm, and in complete control. He knows exactly what Dean needs and how to take him apart without ever touching him.
Dean tells himself it’s just a call. Just one night. But when Cas ends the call with “I’ll call you next time,” Dean realises he might’ve just let something far bigger than desire in through the phone line.
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Summary
Original prompt: I have nothing specific your work is amazing
Or,
The one where Dean only wants his baby brother to do good at uni! He can’t help it if one of the Professors is also his wet goddamn dream. That’s just a perk.
Series
- Part 3 of zation's 10-year anniversary
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Summary
Even the Wild West doesn't make Dean happy, he wants another world.
- Language:
- English
- Words:
- 492
- Chapters:
- 1/1
- Kudos:
- 6
- Hits:
- 87
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Summary
Those who have been reading me for a while know that I hate the fact that Dean is dead. 15x20 who?
And yet...one way or another we have to deal with it. In TW we see that the Impala that Dean finds in heaven is able to transport him, safe and sound, between dimensions, through time, and even into the world of the living. Spasmodically hoping for a S16, I like to think that that Impala is equipped with extraordinary powers, and that she takes him where he needs to go, even if he doesn't realize it.So for this special day I'm re-proposing one of the oneshots published in December. Dean travels with the Impala, hoping to be able to reach Cas in the Empty. But Baby knows that's not the right way. So, Dean arrives where he never expected, in a barn, in Pontiac, Illinois.