Sam Winchester + 8, 18, 19, 20 (wincestiel or winjimstiel) pretty please

8) Sex headcanon
Sam may be very dominant in bed but he doesn’t like total and complete submission. He prefers sex to be like a game of tag where he’s the chaser and who he’s sleeping with is the runner. 

18) Favorite possession headcanon
Sam has a lock box full of all of his favorite and most cherished things. It’s got photos of people who’ve passed, brochures from some of the weirder motels he and Dean have stayed in, what remains of his first utility knife, ticket stubs from plays and movies Dean took him to when they were kids, and other little things. The box itself is his most prized possession. 

19) Favorite photograph headcanon
It’s a photo of himself, Dean, and Cas during the apocalypse. He has no idea who took it or when, but it was one moment of levity between the three of them. Dean’s laughing and Cas is smiling. They all look so much younger back then. 

20) Relationship with/thoughts on _____ headcanon
So Sam was actually the one who wound up orchestrating the whole relationship between himself, Dean, and Cas, though it was mostly accidental. He’d finally given up on making any headway with Dean after he came back from Hell, despite their previous dalliances and figured Dean and Cas must’ve had something based on the way they circle around each other all the damn time. Eventually he realized neither of the idiots made a move and wound up harboring a small little crush on Cas himself. After years of nothing happening and no one doing anything about it, Sam finally reached the end of his patience and told Dean that if he wasn’t going to make a move, he was gonna ask Cas out. Dean called his bluff and Sam and Cas started dating. Of course then Dean got all pouty about it and one half-drunken revelation later, the three of them found themselves in a relationship. 

Thanks! Headcanon Asks

You said that ot3 post should be an ask game so now I need to know if you’re with me or against me with wincestiel 😉

Dammit nevermind you had a tag for wincestiel 🤣

Hahaha! I was wondering if anyone reads my tags. But honestly, this one is canon. Like so canon it hurts. If you can’t see Dean just doing something crazy, Sam giving a paltry “no, Dean, don’t do that” before running after him to do the crazy thing and Cas rolling his eyes because now he’s gotta make sure these two goobers aren’t gonna get themselves killed… well I don’t think we’ve been watching the same show tbh. 

oddsocksandstuff:

My entry for @rosemoonweaver’s fic-o-ween writing challenge!

The Same Again (and nothing like it)

Rating: Teen and Up (I think!)

Pairing: Wincestiel

Warnings: No Archive Warnings Apply

Prompt:

22. Character A comes home to their partner after a long day at work. Then they get a phonecall from their partners phone, despite the fact their partner is right there in the other room, making a lot of noise. When character A answers their phone their frantic partner is on the other end of the line, telling them to run.

Link to fic!

Wincestiel + Rockstar and Groupie AU

samanddeaninpanties:

“Holy shit!” Dean slaps Sam’s arm. Hard.

“Ow!” Sam grouses, glaring at Dean. “What was that for?”

“You suck at this.”

Dean turns Sam so he’s facing the front of the bar and then he sees him – Cas. Castiel. Their favorite singer. “Oh my god. He’s actually here!”

Cas’s eyes flicker and he tilts his head, looking right at Sam. He smiles. Well, it’s more of a smirk, which looks delicious on his glossy lips. His bodyguard gives an irritated full body sigh when Cas begins to walk towards Sam and Dean. “Are you okay?”

“Yeah.” Sam bites his lip, taking in Cas’s eyeliner and short checkered skirt. “Maybe a little too okay.”

“Jeez, kid. You’re not subtle,” Dean cackles, slapping Sam’s back. “Taught you better than this. Or so I thought -“

“I’m twenty-two years old, you ass. Not a kid -”

“Are you boys coming with me or not?” Cas says, hands on his hips. “You’re ruining my buzz.”

Cas kisses and nuzzles Dean’s cock through his red panties before pulling them off with his teeth. “Please,” Dean breathes, spreading his legs wide. “Please fuck me, Cas. I’ve wanted this so long, please -“

“Shit,” Cas gasps when he touches Dean’s used hole. “Who did this?”

“Me.” Sam launches onto the motel bed with a too thin mattress and grabs hold of Cas’s hips, admiring the skirt no one bothered to remove. How it compliments Cas’s ass. Draws attention to it. Sam gives Cas’s butt a swat and watches it jiggle. “Do you wanna be where I’ve been?”

“Only if you plan on fucking me, too,” Cas says, eyes full of unbridled mischief as he glances over his shoulder at Sam. “You gonna?”

Like my work? https://ko-fi.com/outoftheashes

Cat’s Cradle – Dragonwithatale, rw_eaden – Supernatural [Archive of Our Own]

Chapters: 3/11
Fandom: Supernatural
Rating: Explicit
Warnings: No Archive Warnings Apply
Relationships: Castiel/Sam Winchester, Dean Winchester/Sam Winchester, Castiel & Dean Winchester
Characters: Sam Winchester, Dean Winchester, Castiel (Supernatural), Max Banes, Jack Kline, Rowena MacLeod, Victor Henriksen, Patrick (Supernatural)
Additional Tags: Alternate Universe – Magic, Alternate Universe – Soulmates, Witches, Familiars, Witch Sam Winchester, Witch Castiel, Familiar Dean Winchester, Cat Dean Winchester, Enemies to Lovers, Hurt/Comfort, Emotional Hurt/Comfort, Hurt Dean Winchester, Emotionally Hurt Sam Winchester, Emotional Whump, Invasion of Privacy, Platonic Destiel, First Kiss, Frottage, Angst, Major Character Injury, Blood and Injury
Summary:

Sam Winchester isn’t your typical witch. Practicing a taboo form of magic is bad enough, but it’s another thing entirely to have his brother for a familiar. He’s always been aware that there are those who would like to ruin both him and his brother by separating the two, either because they feel it’s unnatural for witches and their familiars to be related or because they want to steal Dean’s magic for their own. So when Castiel Novak shows up claiming Dean’s his familiar… well Sam’s not willing to go down without a fight.

Castiel Novak is a loner. It’s mostly by choice, but really, what choice do you have when you can see the threads that orchestrate relationships? He knows he can’t get too close to people, because in his experience they always leave when the people they’re destined to love show up. So imagine his luck when he finds both his familiar and the man he’s destined to have a relationship within the same week! It’s really just too bad he and Sam can’t seem to get along for five minutes. The threads have never been wrong before but damn would it make it easier if they could just hate each other instead.

Chapter three of the fic @trisscar368 and I are working on is up! 

Cat’s Cradle – Dragonwithatale, rw_eaden – Supernatural [Archive of Our Own]

Cat’s Cradle – Dragonwithatale, rw_eaden – Supernatural [Archive of Our Own]

Chapters: 1/11
Fandom: Supernatural
Rating: Explicit
Warnings: No Archive Warnings Apply
Relationships: Castiel/Sam Winchester, Dean Winchester/Sam Winchester, Castiel & Dean Winchester
Characters: Sam Winchester, Dean Winchester, Castiel (Supernatural), Max Banes, Jack Kline, Rowena MacLeod, Victor Henriksen, Patrick (Supernatural)
Additional Tags: Alternate Universe – Magic, Alternate Universe – Soulmates, Witches, Familiars, Witch Sam Winchester, Witch Castiel, Familiar Dean Winchester, Cat Dean Winchester, Enemies to Lovers, Hurt/Comfort, Emotional Hurt/Comfort, Hurt Dean Winchester, Emotionally Hurt Sam Winchester, Emotional Whump, Invasion of Privacy, Platonic Destiel, First Kiss, Frottage, Angst, Major Character Injury, Blood and Injury
Summary:

Sam Winchester isn’t your typical witch. Practicing a taboo form of magic is bad enough, but it’s another thing entirely to have his brother for a familiar. He’s always been aware that there are those who would like to ruin both him and his brother by separating the two, either because they feel it’s unnatural for witches and their familiars to be related or because they want to steal Dean’s magic for their own. So when Castiel Novak shows up claiming Dean’s his familiar… well Sam’s not willing to go down without a fight.

Castiel Novak is a loner. It’s mostly by choice, but really, what choice do you have when you can see the threads that orchestrate relationships? He knows he can’t get too close to people, because in his experience they always leave when the people they’re destined to love show up. So imagine his luck when he finds both his familiar and the man he’s destined to have a relationship within the same week! It’s really just too bad he and Sam can’t seem to get along for five minutes. The threads have never been wrong before but damn would it make it easier if they could just hate each other instead.

The first chapter of mine and @trisscar368‘s sastiel big bang! Check it out! 

Cat’s Cradle – Dragonwithatale, rw_eaden – Supernatural [Archive of Our Own]

FanFic Writer Appreciation Meme

I was tagged by @purgatoan to do a fic rec meme, created by @frozen-delight, in honor of Fic Writer Appreciation Day. Thanks so much!

Tagging: @maliciouslycreative @mrsgabrieltrickster @braezenkitty @trisscar368 @destielonfire @jemariel @wanderingcas @deadlykittenkay @intotheruins @pherryt

Under the cut, because it’s really long.

1. AN OLD FIC (POSTED AT LEAST THREE YEARS AGO)

Broadway Musical by Griftings (destiel)

This is one of my favorite fics of all time. It’s got a lot of kudos so I don’t rec it a lot, but it kills me every single time. What I really love is the way that the voices of the angels, God, and Jimmy Novak are presented in the fic. The form of the story is a big part of what sells the fic for me. And it’s funny as hell, so that’s a bonus. 

2. A NEW FIC (POSTED WITHIN THE LAST SIX MONTHS)

Why Does It Have to Be (Wrong or Right) by @samanddeaninpanties (winjimstiel + benny) 

Cas and Jimmy are sexy tattoo artists, Sam gets off on pain and Dean is having a really hard time dealing with it. Need I say more? Seriously, it’s an awesome fic and I adore it. There will never be enough winjimstiel for my needs, but this one hits a lot of great notes. 

3. A FIC YOU WISH HAD GOTTEN MORE ATTENTION (LESS THAN 50 KUDOS ON AO3 OR LESS THAN 30 COMMENTS ON LJ)

Feed Your Eldritch Monsters Regularly, Kids by @trisscar368 (WIP) (Gen)

This is my new favorite headcanon about the bunker. Apparently, it’s alive and hungry and creates lots of inconveniences for Sam and Dean and confuses poor Cas. Check it out, it’s funny as hell. 

4. A GENFIC

Made Manifest by @schmerzerling

This fic made me cry, okay! Like a little weepy baby! It’s painful but happy and it hurts but it’s great and I just wanna wrap myself up in it. It’s ftm!Dean and it literally does kill me because it’s just too good for its own good. 

5. A FIC FOCUSED ON A FEMALE CHARACTER

if your mom doesn’t teach you by 8sword (Claire/Emma) 

I had never considered Claire and Emma as a pairing before this but I really love it. Claire’s kind of an asshole but it fits her character and Emma actually has a character and personality. It’s a really good little femslash fic. 

6. A FIC WHICH MADE YOU SEE A CHARACTER IN A NEW LIGHT

Changes in Lattitudes by @winjennster (wincestiel)

Not so much a change in perspective for me but more of a “huh, I really like Sam and Cas together”. Like, I really appreciate that Cas doesn’t give a rats ass about social taboos, that Sam is a total sneaky bastard, and that Dean is….Dean. (You know what I mean.) But yeah, I think this one was the first fic that gave me a chance to see Sam and Cas teaming up and being awesome and wicked and I freaking loved it. 

7. A FIC WHICH MADE YOU SHIP SOMETHING

Pitchers and Catchers by @unforth-ninawaters (deanjimstiel)

Not only did this fic make me ship a thing, it threw me into this wild tailspin of multishipping. (Deanjimstiel is a gateway ship, I’m tellin’ ya.) I think this has probably been most people’s introduction to Dean/Cas/Jimmy and for good reason. The conflict is amazing, the baseball is a lot of fun, and I really enjoyed how the characters grew. There was only one thing I ever was like “yeah, sure, never gonna happen” about it, but then I was proven completely wrong and I should eat my hat. (I’m not spoiling it, but you’ll know it when you see it.) Read it. It’s been highly influential in the DCJ fandom and is also a damn good fic. 

(Also, it took me forever to realize the title was a gay sex joke…shut up.) 

8. A FIC WHICH INSPIRED YOU TO WRITE

Tell Me the One by wallmakerrelict (dean/cas/inias) 

This one really makes me want to write an endverse fic but I know I won’t be able to do it with the atmosphere this one has. The way the word is presented is just tragic and beautiful and oppressive and sad and I love it. I’d like to be able to write something like this (and I’ve tried with dean/cas/inias/sam) but this one just… idk, it sticks with me. 

9. A FIC WITH A PARTICULARLY MEMORABLE LINE

Put Up Your Dukes by saltyfeathers (destiel)

“Okay,” he announces. “I’ve figured it out. Cas, are you ready to witness the reading comprehension my teachers in school never thought I had?”

“Those teachers obviously didn’t give you the chance you des-”

“Okay here we go. So, it’s a metaphor. Like the bath tub.”

“The bath tub is a metaphor?” Cas asks. “When did that happen?”

“A while ago, don’t worry about it. Anyway, about the hidebehinds. Well, what do they do?”

Cas just looks at him.

“Hide,” Dean prompts, raising his brows pointedly. “And what did I do after the- uh-” he glances at Sam, who he did ask not to listen, but still. There are some things he’s still maybe not ready to talk about when in mixed company, and The Thing That Happened In The Gym is one of them. “The thing?” he finishes. “I hid. Like, literally. Behind walls and everything. Even at the time I knew how pathetic it was.”

“So… you’re the hidebehinds in this metaphor?” Cas asks.

That’s all I’m gonna say because it just gets worse/funnier from there and I don’t want to spoil it. 

10. FREE CATEGORY

I’m gonna use this as an opportunity to give a shout out to @pherryt and @deadlykittenkay . @pherryt is currently writing a work called Order of Protection that’s marvelous and you should check it out and @deadlykittenkay wrote a fic called What Happens in Hawaii that painted a beautiful picture of the island and provided a wonderful dose of fluff. 

intotheruins:

rosemoonweaver:

rosemoonweaver:

You can always talk to me about aro!Dean, jsyk.

Clearly the lack of interest y’all seem to have means I need to get more obnoxious about this particular headcanon.

I have a wincestiel headcanon where Dean is aro and always leaves Sam and Cas to their date-nights (they’re both total saps and he loves them but he just doesn’t want anything to do with that), and Sam and Cas felt weird about it at first until they realized Dean really just doesn’t feel that kind of attraction. So they get super sappy with each other, and then show their love for Dean in other ways (like pie and blowjobs in the kitchen and letting him show them how to work on the Impala).

There’s also this whole thing with sleeping arrangements, like they have one room with a big king-sized bed for when they’re all together at once, but they still keep separate rooms in case someone (usually Dean) wants to sleep alone.

Yes! Good!

For the ship thing, Wincestiel?

I’m so sorry this took me so long! I went to bed like 10 minutes before you asked! 

who’s the cuddler: Dean. He’s a hugger by nature, and when he’s most comfortable when he has Sam and Cas wrapped up together with him.
who makes the bed: Dean. Sam gets the corners wrong and Cas doesn’t care so it’s up to Dean.
who wakes up first:  Sam. He likes to exercise in the morning. Dean’s next, usually up to make coffee and breakfast and Cas eventually rolls out of bed last. 
who has the weird taste in music: Sam. He likes the weirdest stuff, 90% of which Dean has no patience for. 
who is more protective: Dean. It’s kind of ingrained into him to protect Sam, so when Cas was added to the mix it was natural to protect both of them. But of course, Cas is willing to do anything for Sam and Dean and Sam’s pretty damn scary when Dean or Cas need him.
who sings in the shower: Dean. And poorly. 
who cries during movies: Again, Dean. Though, there was the Steel Magnolias incident in which all three of them cried like babies. I suppose it depends on what they’re watching. 
who spends the most while out shopping: Cas. Sam and Dean never had a lot growing up so they’re pretty tight with their money (even if they don’t really have to worry about it). Cas is much more willing to buy them all things they want but don’t need. 
who kisses more roughly: Sam. He knows both Cas and Dean can take it, and he’s more than a little demanding at times. 
who is more dominate: Personality wise, it’s Dean. He’s louder and much brasher than either of them. In the bedroom, it’s Cas. He’s bossy. (Though there are times when Sam gives Cas a run for his money.)
gets jealous the most: It’s not that Cas is jealous, it’s just that he feels insecure a lot of the time. Sam and Dean are bonded in a way he’ll never hope to replicate with anyone. Sam sometimes gets a little jealous of how Dean and Cas always seem to be on the same wavelength even when they butt heads. Dean is a little jealous of all Sam and Cas have in common. (He did try to express interest, but some of the podcasts they listen to him make him want to tear his hair out.) 
one headcanon I have: I think one of my favorite headcanons/tropes is that Cas is the whole reason it happens. Like, Dean and Sam have had entirely unbrotherly feelings for each other for years, but they don’t say or do anything about it until Cas decides he’d like to sleep with both of them. So then it’s threesomes with strict “no touching” rules and then maybe coincidental touching is okay. And then, okay, it’s not really that bad if it’s just kissing, right? It’s just kissing. And well, if it’s DP it’s only coincidental that Dean and Sam’s dicks touch. Right? That’s not incest or bad, right? Then… well, maybe Dean can’t help it if Cas is giving him an order to touch Sam, right? He could say no but he maybe doesn’t want to. And then somehow Cas walks in one them making out in the kitchen with a smug as fuck smile. Then everyone’s happy! 
Sorry, that got NSFW. Ooops. 
nicknames: They’re not really “for” nicknames, just more snide terms of endearment. (”bitch” “jerk”) But I would bet that Dean only calls Cas “sunshine” when he’s being a grump and Cas usually enjoys calling Dean “asshole”. Sam doesn’t usually get passive aggressive nicknames thrown at him from Cas. 
my rating of the ship from 1-10: 10