1 - 20 of 23 Works in Annoying Sam Winchester
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Somewhere Between the Crossroads and the Righteous Man by whiskeydays
Fandoms: Supernatural
25 May 2025
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Hunter Dean Winchester is used to flying solo and he has been hunting alone since his father died couple of years ago. But a particularly difficult case with a lot at stake forces him to rely on some unwanted help. Not only is the demon, Sam, really annoying but his presence makes Dean feel uneasy with his sexuality for the first time in years. Then things start to unravel and Dean is forced to face the fact that not everything in life is black and white. Not even demons.
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‘Til death do us part… yeah, not likely when you’re Dean Winchester and Castiel is your husband.
When Cas passed away Dean didn’t handle it well, that is until he starts seeing his ghost around the house. Now he has him back and everything is fine, or it would be if everyone would just leave them alone.
This is not a story about letting go, its about hanging on tight.
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Sam is sad that his older brother, Dean is leaving for college with his besties. Sam doesn’t want his big bro to leave but Dean adds him to group chat with his friends.
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The haute-couture world is rocked when the supreme brand Cupid lures the Angel Castiel out of retirement. He emerged for one reason alone, the up-and-coming model Dean. Co-starring in a fragrance campaign, the pair are slow-burning their way through Monaco, perhaps raising the Mediterranean Sea to a boiling level, but how couldn't they?
A WIP with so much more to cum... that's what he said.
*** Now complete ***
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After being called ‘weird’ by the kids in town, Jack asks his dads whether they think it’s true or not. Various musings on why they’re all weirdos in their own right.
Based off of a Tumblr post where Jack kept a lot of his devily type powers.
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They got back from their midterm break, a new show hits Amity Park too.
Dash is also acting strangely,
Danny shouldn’t care but he does.
They started getting closer because of it, like what the hell is he thinking?So, “It’s a typical bully love story Danny.” -Jazz Fenton
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There are a million little ways to say I love you. Here are 26 moments from Dean and Castiel. From A to Z and everything in between.
A is for Angel. Dean would do anything for his angel, even kick his stubborn ass into place when he needed it.
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Dean gets dosed with magic LSD. It’s not his first time at this particular rodeo, well, the magic part is new. And man was this sure a different show when he was a teenager. Now all he can think about is the fact that he feels like he’s either about to throw up or fall off into oblivion. Oh, and the faces. Everyone’s fucking faces. Zooming in and zooming out. Sam looks ridiculous. The characters on his TV look terrifying. Cas… Cas is just a bunch of eyes and rings and glowy shit. It’s honestly hard to focus on anything but Cas on a good day. When he’s high as a fucking kite, tripping balls on an unexpected psychedelic experience? Forget about it.
Series
- Part 1 of Destiel Month 2022
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This will be an ongoing series, re-writing the office using our favourite supernatural characters.
There will be eventual Destiel.
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They've been together for a hot minute, and have yet to do anything...of a certain sexual nature. Castiel is starting to wonder why. He's not fragile. He won't break. Now he just has to get Dean to see that too.
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the rocks we fell in love with (while learning to fall for each other) by ClassyTomboy9327
Fandoms: Supernatural
21 Nov 2021
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After a hunt, Sam and Dean return to the bunker and there is huge surprise that awaits them. Especially for Dean. Maybe something more than he expects.
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The Dean grows his hair out, starts feeling more comfortable in his sexuality and relationship with Cas, and slowly quits hunting fic; because I have to do everything myself.
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He doesn’t think much about it at first. At its base, it’s just a nickname. A nickname for someone he’s dating, sure, but a nickname nonetheless.
He expects to throw something out and just have it stick. Happy boyfriend with minimal effort.
When has anything- especially in regards to Castiel- ever gone that easy for Dean?
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In which Sam is a typical annoying little brother, Cas is picky with his pet names, and Dean just loves his boyfriend.
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“What, you don’t think this warrants any kind of discussion?"
Or: Sam is nosy, Dean is uncooperative.
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In many fanfictions we noticed the repetitive prompt of a homophobic ghost with the : " BUT DEAN , all the victims are gay , why did it come after you ? "
" Because I'm Bi Sammy "They're good . BUT .. how about ...
the ghost is gay , and it haunts abusive homophobic people . including John Winchester . so for a change
" But all the victims are abusive homophobes , why did it go after Dad . " Sam asked his brother .Edited
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You and Castiel are sick of being teased by the brothers, so you plot your revenge. It doesn't turn out quite as you had expected.
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“Dean, what’s this?” Sam asked, a knowing smirk to his face as he pointed out the notebook he had given his brother.
“Oh that?” Dean asked. The book was open on the first page and had something written in it. “It’s my to-do list,” He shrugged, almost uncaringly.
“That’s great Dean!” Sam exclaimed, excitedly. All this nagging was finally starting to pay off! He picked the book up to give the list a read; maybe he could help his brother achieve some of the goals he’d set himself. “I’m really glad you’re starting to…”
Sam stopped. He had to re-read the list a few times before he could speak again.
“This just says ‘Castiel’.”
~THE TO-DO LIST~
Sam keeps bugging Dean to get more organised, until Dean decides to write a to-do list and leave it right where his brother won't miss it. -
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College AU in which Cas is the little fucker messing with his professor's head. Hope you enjoy!
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This started out as a one-shot, but it's obviously a multi-chapter now, so it's a little bit more complicated than what it says above. But, if you just want a one-shot, the first chapter can stand alone, and you don't have to read past there. Thanks, everyone! Enjoy!!
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Chloe, Nadine, and Sam went out for dinner on the last night they were all together. Sam was going to his brother’s residence to tattle on Nadine; Nadine and Chloe didn’t have any plans for their next adventure. The restaurant’s food was much tastier than MRE’s, even though the freeze-dried beef stew was growing on Chloe. Maybe tonight would kickstart her five senses; they’d dulled from the constant pain of treasure hunting.
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Dean just wants to make the rundown house they’re squatting in look cool for Halloween, but Sam isn’t so excited about strangers in corny costumes knocking on the door for candy. Not when there’s a gang of ghouls wreaking havoc in the neighborhood, anyways.
Series
- Part 4 of wincest one-shots