#older dean

[sams-subtext]

Big Brother Knows Best

Sams warnings: Nsfw, very very nsfw. Size difference kink 10000%, incest/wincest. Just overall not for the kiddies. Younger!Sam, Older!Dean

Holy Chuck and all his angels what have I created ;;

Time travel, huh. Felt like a back to the future moment for Dean, but he wasn't here for his father. He was here for his brother.

He thought, maybe if he went back to warn Sam about what was going to happen before it did then, things would change. Sam wouldn't have gotten in to this whole mess, wouldn't have said yes to Lucifer, wouldn't have died multiple, multiple times

Dean wanted to put it all back into place.

Young, fresh into college Sam sat in his grungy apartment, flicking through channels on the TV, yawning as his eyes felt heavy. He was knocked back into his senses when his door was, pretty much, kicked down.

Sam panicked, thinking he was being robbed, grabbing his dagger from the table and running at whatever mysterious thing was trying to get him, only realising the familiar sound of his brothers voice.

"Sammy!"

"..Dean?"

Dean swallowed as he saw his little brothers state, messy hair, half lidded eyes, large t-shirt that basically drowned him and a pair of tight, ohsotight, boxer shorts.

The thoughts of those shorts being flung across the room as he stuffed his baby brother up was floating around in his mind.

Maybe there was going to be a slight change of plans.

The small talk as to why Dean was here was quick, he made up some excuse of "I just wanted to visit my little brother" or some lame family excuse like that. Sam didn't even stop to question on why his brother looked so...old.

He was too busy thinking about Deans' chiseled jaw, and holymaryandjospeh his pecs. God they were like two mountains, two perfectly roundly shaped mountains.

Sam swallowed as Dean grew closer, putting his hand on Sams' shoulder to give him one of those "big brother" talks, but Sam was zoning out thinking about how Deans' hand would squeeze perfectly around his ass.

Eventually, his thoughts became more...noticeable.

It all happened so fast, really really fast, too fast for Sams' brain to keep up with. One minute he was talking on the couch with Dean, the next he was on his hands and knees, face shoved into a pillow as Dean stuck his fingers in Sams' mouth, getting them all slick and wet.

"Fuck Sammy, this is a good look for you, baby brother".

Shamefully, Sam whimpered, arching his back and pushing his ass closer to Dean. "Dean, please, need you—". Sam gasped as two of Deans' fingers were roughly slid into his tight, pink hole. Sam had never experienced anything in his ass before. Sure, he'd thought about it. But he was always too afraid to try.

Dean groaned at Sams' noises, his dick was hard enough to hammer nails, he was going to enjoy this. Filling his poor baby brothers ass up with his big brothers dick. Yeah, thats all he needed. His big brothers dick making him feel so good.

"Oh Dean please, need you so bad, need your dick inside me ple—". Sam was cut off by his own whimper as Dean removed his fingers, soon enough being replaced by something much larger, and thicker.

Sam let out a strangled cry, arching his back, grinding down to get Dean further into him, making Dean groan. Dean didn't give Sam time to think as he started thrusting into him at a quick pace, making Sam crumble into a moaning, whimpering mess.

"Yeah that's right Sammy, fuck. My baby brother, my fucking pretty pet."

"OhOH FUCK DEAN oh god you feel fucking amazing—".

Dean kept pounding into Sams' tight hole, his ass hitting against Deans' hips at every thrust. Sams' small body could barely keep itself up, Dean had to reach his hand around to hold Sam up.

Poor baby, Dean thought, Can't keep himself up as he's being pounded into.

Sam felt his stomach twist, crying out Deans' name as he attempted to form a sentence through his babbles, "Oh god Dean 'm gonna—"

Dean groaned, grabbing Sams' hips, "Go on, baby brother. Cum. Wanna hear you scream your big brothers name."

Sam cried out a moan, arching his back as he came, his voice cracking. "OhOH OH FUCK DeAn". Dean moaned, bucking his hips into Sam as he rode out his orgasm.

"Fuck— Shit, that was—"

"Amazing, I know."

Dean went to pull out before Sam stopped him, managing to swirl round to lay on Dean, "Not yet, wanna— Wanna keep this inside of me."

Dean smiled, running his thumb over Sams' cheek, pressing a small kiss to his beautiful, plump lips. Maybe Dean could stay here for a while.

"Love you, big brother."

"Love you too, little brother. See? What do I always tell ya? Big brother knows best."

#hot damn #sam winchester #dean winchester #oh lawd #they fuckin #wincest #wincesties touch this post pls #older dean #younger sam

[queermania]

You will get older (threat🔫).

#get older idiot <3 #birthday party for dean 2024 #celebrate good times come on #deanedit #dean winchester #spnedit #supernatural #myedit #dw

[scenteddean]

I've had this 90% finished since the beginning of january, but thankfully have been dragging my heels on finishing the rest just to be done on time for a very special day <3 happy bday smart angel

#dean #my art #spn fanart #he's just a little guy... #while drawing this i realized it had a similar compostion and facial expression as another drawing from jan '22 of wrinkly older dean #made me a little emotional

[nimblefoxes]

This started with “Dean totally has orange cat energy” and just kept going and now I’ve lost all control???? Also nobody tells you cat anatomy is WEIRD. Why so bendy???

Special thanks to @lordcrowcifer for his suggestions for Crowley & Gabriel! (He made a strong case with the perfect photo of an angery looking Scottish Fold 😂)

More suggestions are, of course, welcomed because I have nothing better to do than draw dudes in plaid as cats.

#hi welcome to my blog I draw silly cute shit #that one day I hope to draw other things but I can’t control my hand #we just end up here LOL #this is low key a redraw of an older piece that gets dredged up once in a blue moon #supernatural #spn fanart #spn #supercatural #spn au #Destiel #crowley #dean winchester #sam winchester #bobby singer #Gabriel #castiel #BYE NOW

[older-sister-death-match]

QUARTERFINALS - MATCH 2

Propaganda Under The Cut:

GERARD WAY:

prettiest girl in the whole wide world

DEAN WINCHESTER:

i dont even have to explain this one do i

LILITH CLAWTHORNE:

ok she and eda are literally the most precious ever and yeah they are enemies for most of season one but they make up and lilith stops trying to capture her baby sister and instead takes on part of her curse and becomes the most aroace cool aunt historian bad girl of all time

#older sister death match #tumblr polls #fandom polls #polls #tournament polls #gerard way #my chemical romance #dean winchester #supernatural #lilith clawthorne #the owl house #you guys don't know how excited i am for the bloodbath that will ensue

[cinemabuffoon]

If I'm not supposed to have crushes on middle aged men then why are they so hot? Explain that political party of your choosing

#this counts for fictional middle aged men too btw #and men older than middle aged too 🙃 just easier to say middle aged #crushes #actors #tom cruise #gerard butler #mads mikkelsen #idris elba #jon bernthal #etc #benicio del toro #pedro pascal #matthew lillard #patrick dempsey #jeffery dean morgan #antonio banderas #hugh jackman #rick grimes #jason statham #dolph lundgren #bill paxton #kurt russell #henry cavill #jason isaacs

[crocodilenjoyer]

he's our little brother. take care of him.

anne carson - antigone / alec benjamin - if we have each other / dan pearce - single dad laughing: the best of year one / kodaline - brother

#dean winchester voice we're gonna fix you up. that's my job right? to look after my pain in the ass little brother. #[guy who's not over marineford voice] yeah i'm sooo over marineford #tried to read the manga for reference. got sad about ace and luffy again. thus the cycle continues #asl brothers #ace #luffy #sabo #riko.txt #one piece #op spoilers #kinda???? it's been out for over a decade. everyone talks about it #btw you have NO IDEA how much it took for me to not include the spn gif i made for this. or the shinazugawa bros scene. you know the one. #anyway. hahaha. heehee. hohohoho. i'm an older brother. i have a younger sister. and. i get it. #she was having a bad time a few months back and i remember telling her i'd do anything for her. i don't think i've ever meant anything more #so. yeah. i get it.

[lambmotifz]

dean is possessive of sam in a way that he’s the only one who can own sam, and sam is possessive of dean in a way that he’s the only one dean is allowed to own. dean can’t stand the thought of someone else owning sam and sam can’t handle not being the center of dean’s attention. they’re both equally possessive of each other but in different ways

#and it becomes more obvious the older they get #wincest #samdean #sam winchester #dean winchester #spn

[zombiegirldean]

What if God told Abraham to kill his son and Abraham was like this is kinda awkward but um God just told me I have to kill you. And then Isaac dragged Abraham up the mountain and said OK. Do it. I'm ready, I've always been ready. Sacrifice me at the altar, I'm BAD I'm WRONG there's some rotten seeping poison in the very center of my being, and you are the only one I trust to cut it out. And Abraham was like wtf no you're my kid I can't kill you and Isaac was like you HAVE to. God TOLD YOU TO. "Well maybe God's an asshole!!!" No you don't understand, You're the ONLY ONE who can do it. Promise me you'll do it, promise me if I step out of line you'll put me down like a bad dog, please please please. Cannot stress enough that this is literally what happens in Supernatural s2 e11 "Playthings".

#supernatural #dean winchester #sam winchester #youve heard of suicide by cop. now get ready for suicide by your crazy drifter savior complex older brother who thinks he's your mom #cant stop thinking about how horrible this is . the way dean says : Dont ask that of me. DONT ASK THAT OF HIM #spn

[whatohitsonfirewelp]

Older siblings in media are so often misunderstood. Either adored or hated, but never an in-between. The pressure is always there, never enough or too much.

It’s the Steven Crain’s who are hated, the Fiona Gallagher’s who are forced onto a pedestal, the Dick Grayson’s who are reduced to nothing but their mistakes and issues, the John Dory’s who is only ever the oppressor and never the oppressed, the Isabela Madrigal’s who are considered vain and self centered.

It’s the eldest child who has no one on their team because they are the leader, and that is either meant to be taken from them or only ever for them.

It’s the Kate Sharma’s and the Anthony Bridgerton’s. It’s the Bill Weasley’s and it’s the Dean Winchester’s. It’s the Eric Matthew’s and it’s the Elsa’s.

The eldest sibling whose mistakes are over analyzed or completely ignored, who are never seen as humans because they are something to claim or destroy. The first born who is never understood in media or by fans, maybe it’s because acknowledging the fact that they’re human means they aren’t perfect is too much. Or maybe it’s because acknowledge that they are human and therefore cannot be defined by their mistakes and the weight they carry is too much.

They are not allowed to be perfect and yet if they are anything but perfect the world would riot.

#fiona gallagher #isabella madrigal #kate sharma #anthony bridgerton #steven crain #dick grayson #john dory #bill weasley #dean winchester #eric matthews #elsa frozen #there’s so many more older siblings that go here but u can’t fit them #all but you guys get the point #just #why can’t we ever let the eldest sibling be human? it’s either they only make mistakes or they never make mistakes #and how is that fair how does that allow them to grow or develop or live #whatoh back at it again

[youchoseeachother]

Sam, getting to know Dean in season 1.

#was there even anything he knew about dean. like... #i wonder if it's because dean has changed a lot during the four years they were apart #or if sam was too young/immature to actually see dean past his exterior before stanford #probably a mix of both. but it's so interesting because the idea he had of him doesn't have anything to do with the actual dean!! #sam winchester #dean winchester #supernatural #spn season 1 #corespnedit #.anna #also psst this is why it's dumb to call dean a creep just because sam once implied that dean would sleep with minors #like sam at times tends to see him as worse than he is! #like when he can't believe dean actually loved cassie or cares about saving a kid's life #so - don't trust too much what he says about him #in particular because all of the women dean actually slept with were roughly the same age as him or older #(aside from the fact that sam was probably joking that time)

[thesmuttyduchess]

#i wish i was joking #older man younger woman #d!lf #daddy's good girl #daddy issues #praise k!nk #pillow princess #older simon riley #simon riley x reader #pedro pascal #joel miller #dennis quaid #cillian murphy #jeffrey dean morgan #patrick dempsey #matthew mcconaughey #oscar isaac #i must be forgetting someone but i cant remember rn #girlblogging #smutty smut smut #but daddy i love him

[superlunar-eclipse]

🌑 ੈ✩‧₊˚ ━━━━━ ACROSS THE COUNTRY

SUMMARY ➤ Dean and Sam, concerned about their missing father, approach their estranged elder sister Y/N, an FBI agent, for help. Despite initial resistance due to past grievances and her current job, Y/N eventually agrees to join them in their search, setting the stage for a journey filled with potential challenges and dangers.

WARNINGS ➤ injury’s, injured Y/N, stabbed wound (to the shoulder), small shard of glass on Y/N’s face and the back of their head, and slight arguing.

CHARACTERS ➤ Dean Winchester, Sam Winchester, Y/N Winchester, mentions of John Winchester, and Adam William (added character)

WORD COUNT ➤ 1,180 words

OTHER ➤ Y/N is a FBI agent, small mention of Y/N being 32 years old, set in season 1, episode 1.

AUTHOR’S NOTE ➤ first fanfic! hopefully dean and sam don’t act too OOC, but lmk if they do!

"Dad hasn't been home in a few days."

Sam took a deep breath before responding, "So, he's working one of his usual overtime shifts on a 'Miller Time'. It's nothing to worry about. He's bound to stumble back in sooner or later."

Dean glanced down at the cold, hard ground, allowing his eyes to linger there for a moment before looking back up at Sam. His voice was full of concern as he said, "Dad’s on a hunting trip, and he hasn’t been home in a few days."

Sam’s expression remained stoic, giving away nothing of the worry that was slowly starting to creep in. Jess, who had been quietly observing the exchange, glanced up at him.

"Jess, excuse us. We have to go outside."

"I mean, come on. You can't just break into my place in the middle of the night, and expect me to hit the road with you," Sam said, his voice echoing in the silence of the night as he followed Dean down the stairs.

"You're not hearing me, Sammy. Dad's missing. I'm not just asking you to hit the road with me. I need you to help me find him." He looked back at Sam, his eyes pleading for understanding.

"I- I don’t understand, why couldn’t you have called Y/N? Isn’t she an FBI agent or something like that?" Sam questioned, his hand reaching out to grab Dean’s shoulder in an attempt to halt his progress.

Dean sighed loudly, a sound that echoed throughout the quiet night. He bounced on the balls of his feet, a nervous habit he had whenever he was troubled. "Well I… kinda don’t know where she is…" he admitted shamefully.

Sam’s eyebrows furrowed, a clear sign of his confusion. "What do you mean you ‘don’t know where she is’?"

Dean pursed his lips and rubbed his hands together, his gaze dropping to the ground. "Well I don’t know her exact location but I know she’s somewhere in Washington DC or something like that!"

Sam scoffed in disbelief and shook his head. "That’s all the way across the country."

"Well did you want this to go quicker?" Dean shot back defensively.

Sam simply rolled his eyes at Dean.

"Look, are you coming with me or not?" Dean asked, his patience clearly running thin.

"I’m not." Sam said, his tone leaving no room for argument.

"Why not?" Dean questioned, his frustration clear.

"I swore I was done hunting. For good."

"Come on. It wasn’t easy, but it wasn’t all bad."

Dean starts heading down the stairs once again, with Sam quickly on his trail.

"You know, in almost three years I've never bothered you, never asked you for a thing," Dean tried to reason, his voice softening.

Sam looks away and sighs, then looks back.

"All right. I'll go. I'll help you find the both of them."

Y/N, a 32 year old FBI agent, sat in the back of the ambulance as the woman cleaned up her many cuts. Her shoulder had been stabbed by the unsub and her head was smashed into a sheet of glass.

"Alright, you're done." The woman finished cleaning her cuts, placing a bandage on her forehead and applying gauze tape to her wound.

Y/N smiled at the woman and hopped off the ambulance truck.

"Y/N!" someone shouted from the distance. She turned to see her great friend Adam, who was the first one to welcome her to the FBI.

She smiled softly as he gave her a comforting hug, "Ow, my shoulder." Her nose scrunched up in pain.

"Sorry," the corners of his mouth turned up as he let go of her.

Other agents of the FBI walked up to her, thanking her for her bravery. "Thank you for saving that girl's life."

"No problem." She gave them a comforting smile.

The agents walked away to discuss matters with other departments.

Y/N and Adam talked about the case for a little while, before Adam turned his attention to something behind her.

"Hey, do you know those people over there?" He asked.

She turned around to look at the people Adam was pointing at. She tilted her head to the side, squinting slightly as she tried to recognize them.

Why did they look so familiar?

Her face paled when she realized who they were.

"Uhm, yea- yeah I do, I’ll be right back," she stuttered, patting his shoulder reassuringly before she walked away.

"What are you guys doing here and how in the hell did you guys find me?" Y/N whispered-yelled at the two boys, her eyes wide with surprise.

"We need your help," Dean replied simply.

Y/N furrowed her eyebrows and put her hands in the back pockets of her jeans, "Oh, so all of a sudden you both need me after what, three years of not talking to me?"

Dean, with a dramatic flair that was all too typical of him, let out an exaggerated sigh. "Listen-" he began, a note of desperation creeping into his voice.

But she cut him off, her frustration palpable. "Dean, please, I really don’t have time for this," she said, waving a hand dismissively.

Sam, practically silent until now, took a step forward. His eyes critically scanned over her face and body, noting the signs of recent distress. "What happened to your shoulder?" he asked, his voice filled with genuine concern.

In response, she lifted a brow and shot him a sarcastic look. "Take a guess, Sam. I’m in the FBI," she said dryly.

He rolled his eyes at her retort. Typical Y/N, he thought, not for the first time.

Dean, who had been silent during their exchange, finally spoke. "Dad’s been missing for a few days, and we… we need you," he stated, his eyes narrowed and serious.

Her reaction was almost immediate. Her jaw tightened, her eyes darkened, her whole demeanor turned defensive. "And why would I want to find him?" she shot back, her voice icy.

He faltered, at a loss for words. He turned away, his gaze landing aimlessly on the nearby crime site.

Now it was Sam’s turn to speak up. He stepped forward, his eyes pleading. "Y/N, please, we really need you right now," he implored, giving her a puppy-dog look. It was a tactic he used to use all the time when he was younger to get what he wanted.

She looked away from him, her lips pursed, her face screwed up in thought. After a long pause, she finally voiced her question. "How- how long is this going to take?"

Dean was the one to answer. "Four days."

She sighed out loud, a wearied sound that echoed in the silence. "You do realize I have a real job, right?" she asked, a note of exasperation in her voice.

Dean rolled his eyes, a retort already forming on his lips. But before he could speak, Y/N interrupted him.

"Fine, I’ll go with you two," she said, her voice resigned.

Dean smiled lightly, relief flooding his features. "Thank you, Y/N."

And so, they walked together to Dean's car, unaware of the challenges and dangers that lay ahead of them.

#supernatural #supernatural fanfiction #dean winchester #dean winchester x reader #dean winchester x you #dean winchester x platonic reader #dean winchester x sister!reader #dean winchester x female!reader #dean winchester x older sister reader #sam winchester #sam winchester x reader #sam winchester x you #sam winchester x sister!reader #sam winchester x older sister reader #winchester!reader #Y/N winchester #dean winchester fanfic #sam winchester fanfic

[secondbeatsongs]

when you're into the Big Ship™ in a Big Fandom™, you have the luxury of having an OTP - a real One True Pairing, where you can read about just them for ages, and you will never run out of fics, and everything is perfect and beautiful and nothing hurts

but when you go to a smaller fandom, you'd better pray to whatever god you worship that someone else in this room ships the same thing that you do, and that if they do, they're writing more than late-night crackfic, because you're on thin fucking ice!

and how small is your small fandom? is it less than 100 fics? maybe even...less than 20 fics?

welp, then it's time to make peace with that god and either open up a text document or learn how to ship everything, because it's swim or drown babey! and your ship is sinking fast

anyway all of this is to say that after hanging out in small fandoms and shipping less-common pairings for a while, going back into a Big Huge Fandom™ is wild because suddenly it's like...wait, why didn't I ship these people again? I don't remember. why was I only sticking to one ship in this fandom?? boring of me, honestly. these guys should make out.

#sbs rambles #fandom #fandom stuff #ao3 #basically. I hung out in superwholock for so long back in the day #but then I got weird and cool and moved on to smaller and older and stranger fandoms #and decided to throw a party and have fun and enjoy all of the small and weird in those fandoms #and now rewatching media for a big fandom I'm like. huh. sucks to be everyone else I guess. they're missing out on some wild dynamics here #because I'm havin a blast #and like. when I mean small fandoms I mean SMALL #my one fic I wrote for one tv show makes up 25% of that entire fandom on ao3 #(double checks) #oh!!!! new fic in the fandom!!!! #my one fic only makes up 20% of that entire fandom on ao3!!! #time to throw a fuckin party! 🎉🎈🎊🥳 #anyway it's really funny because based on this some folks are going to assume what ship I'm into in a Big Fandom now #but buds. you can laugh at me #I'm thinkin about sam and cas #what's up with those guys? #fucked up actually. they should hold hands about how much they love dean #:') #but also supernatural is way more fun if you watch it out of order #that's what I've realized #now if only the RNG would give me something in season 1 or 2 T_T #also if you're at the point of reading fic on livejournal or wattpad in the year 202X you've reached ''small fandom'' status #that's the rules

[older-sister-death-match]

ROUND 3A MATCH 4

Propaganda Under The Cut:

DEAN WINCHESTER:

i dont even have to explain this one do i

LILITH CLAWTHORNE:

ok she and eda are literally the most precious ever and yeah they are enemies for most of season one but they make up and lilith stops trying to capture her baby sister and instead takes on part of her curse and becomes the most aroace cool aunt historian bad girl of all time

#older sister death match #tumblr polls #fandom polls #polls #tournament polls #dean winchester #supernatural #lilith clawthorne #the owl house

[hensel-x]

I HAVE SOME OPINIONS ABOUT SUPERNATURAL GENDERBENDS.

Listen. I love that image of fem dean that most people in fandom have, with her being like a really cool masc woman with an undercut who is confident in her bisexuality and has no problem sleeping with both men and women. I love her dearly.

BUT. Realistically speaking. Look at john winchester (and tell me there’s god). and the amount of INSANE toxic masculinity bullshit that goes on in canon dean’s brain that actively makes his life worse.

Imagine what kind of GIRL would john winchester raise.

Fem dean would have contradicting roles she needs to fit in. on one hand there’s this image of picture perfect mother/wife that mary was in john’s eyes and that he forces on deanna. On the other theres Family Business which you Can Never Escape. She should be daddy’s daughter, good older sister, future mother and wife but she can never achieve that, so she is ultimately Fails as a Woman. Insert canon dean’s thoughts about being a freak. Worst case of “not like other girls” mentality. Mary as unachievable ideal of traditional femininity which is totally alien to deanna.

And talking about fem sam in my mind Jessica stays her Girlfriend

And that is the core of deanna and sam’s conflict actually because in dean’s eyes sam escapes Family Business so surely she can now be the Right Woman even if deanna herself cant have that?

WRONG, sam doesn’t give a shit about johns views on gender roles, she wants to be a lawyer of all things and lives with another woman. A fucking slap in the face.

John the kind of father to forbid sam from painting her nails in high school cause The Hunt but also gets mad at her for cutting her hair short over a sink.

ALSO I think it would be INSANELY COOL for sam to have hoodies with those 2000s graphic crosses/angel wings prints as sort of foreshadowing

 And Rowena is a dilf witch now yeah.

#my art #supernatural #supernatural fanart #dean winchester #sam winchester #genderbend #dean winchester is an older sister #gender thoughts #when sam is in hell deanna becomes a soccer mom #oh and also gabriel's fem vessel is inspired bt bridget jones