#john winchester headcanon

[ilovejohnwinchester]

Thinking about early days on the road before John started leaving Sam with Dean and was still going around and talking to hunters trying to learn everything he could. Imagine you’re some hunter and you get a call that the new guy in town wants to meet at the roadhouse and talk demons or werewolves or witches or whatever, then he shows up with a 4-year-old and a baby. He’s real serious and writes down everything you say in his journal but he also has to get up halfway through to sing and bounce a cranky baby to sleep on his shoulder while the kid stares at you with a mouth full of French fries. No wonder every hunter in John’s generation seems to remember Dean and Sam whether Dean and Sam know them or not.

[ant0niepax]

Honestly I love how I upgraded from Wattpad to tumblr, less cringe but still cringe to keep it entering

[castiwls]

"uh-oh, i'm falling in love."

being Bobby's adopted daughter and falling in love with Dean... [requested - anon]

You were around 15 when your parents were killed in a hunting incident and as a result, Bobby ended up taking you in.

You’d spent the first few months sulking around the house, something which began to worry Bobby as months passed and your behaviour seemed no different.

He knew he had to break your behaviour somehow but he was completely stumped. That was until one day he woke up to John quickly shoving his sons in the door before running off to do go knows what. 

Silently cursing the man out he quickly invited the two boys inside before continuing with breakfast (now for 4 people). 

“Who are they?” You looked up from the book you’d been reading, frowning in slight confusion at the two boys who were currently standing in the doorway. The younger of the two smiled brightly before almost tripping over himself to see what you were reading while the older silently gapped in the doorway. Since when did Bobby have a daughter?

After this, you quickly found friends in both the boys. 

While Sam was someone who you could talk to about lore and any other books you might have been reading, Dean was someone who you were able to fully confide in.

Over the three weeks the boys stayed you and Dean quickly became inseparable and for the first time in months, you didn't feel grief-stricken constantly. You actually felt happy.

Over the years Sam and Dean became a constant in your life. As you grew older Bobby began letting you go on hunts with the Winchesters (something which Dean enjoyed more than he would admit.)

Over time though you felt a slight shift in your feelings towards the older boy. Every time you saw him or even heard his voice butterflies would swarm in your stomach and your cheeks would quickly grow hot.

The shrill ringing of your phone pulled you from your book. A small frown played on your lips as you noted the name on your screen. “Hello?” Placing your book down you crossed your legs sitting up properly on your bed. “Hey. I didn’t wake you right?” Dean sounded sheepish almost as he spoke. At the sound of his voice, a small burst of butterflies exploded in your stomach. “no..no I was awake.”

Late-night phone calls quickly became an almost daily occurrence whenever you weren't together, and when you were together these phone calls were exchanged for late-night diner trips just the two of you.

Every day you felt yourself falling harder and harder for Dean Winchester and little did you know he felt the same.��

After Sam had gone to Stanford Dean had showed up on your doorstep only hours later, his eyes red as he’d quietly asked to stay the night.

He’d ended up staying for a few weeks after that. You’d spent every day together over that time simply listening to him talk about what had happened between his dad and brother and how he was scared for Sam being on his own.

As happy as you were that Sam had gotten out it broke your heart slightly to see how Dean was handling the situation.

Over this time you’d found yourself more than once falling asleep beside him (something which Bobby wasn’t too happy about) and you’d also felt yourself grown closer and closer to him.

He’d allowed himself to be vulnerable around you, something which you knew was hard for him. The idea that he trusted you enough simply left your heart fluttering in your chest.

During these few weeks, Dean quickly found himself falling further and further in love with you. He’d known for a while now that he had feelings for you but the way you’d allowed him to unload onto you and made him realise how utterly in love with you he truly was.

One night when you’d both been sat on one of the old cars in the scrap yard he finally felt his feelings bubble over.

The world was quiet as you and Dean both sat watching the stars above. You knew he had to leave soon, his dad had been relentless with his calls saying that Dean needed to come back to his job and that he’d had enough time. Truthfully you didn’t want him to leave. Over the last few weeks, you’d grown used to the warmth of him beside you. “My dad’s coming in the morning.” Dean turned to face you. “He insisted this time.” He frowned, rubbing his thumb over your hand. “What time?” You asked quietly turning to look at him. “He didn’t give one,” Dean answered. You both fell slightly for a moment, simply gazing into each other's eyes. As if being pulled in by a magnet you felt your body move on its own until you met Dean halfway. As his lips pressed against yours you felt his hand cup the back of your head while your own moved to his knee.

After that night your relationship changed. Neither of you actually asked the question but the unspoken promise was there. Dean Winchester had stolen your heart and it seemed you had also stolen his. 

[spn2006]

thinking about the years that sam was at stanford and it was just dean and john alone together, for really the first time in dean’s entire life. do you ever wonder how quiet the car rides must’ve been? how restless dean was, sleeping for the first time in a room with no sam. how many times do you think john almost bought extra supplies for sammy at whatever run down drug store he ran into, just as a force of habit. do you think the two of them ever grieved, knowing their sweet boy was still alive but practically dead to them. and what about the arguments they must’ve had, when the absence of sam got so overwhelming and they had to blame someone and had nothing else to do but shout at each other—but never loud enough for sam to hear.

[nyxiswrites1200]

Muscular!men x Curvy!fem

Slight NSFW, Slight body image issues/insecurities, I'm self-indulging

----

Something about big strong men and soft curvy women just melts my brain ❤️

Large men who are muscular and just have a large presence in the room (dobermans and golden retrievers <3). Very well can win fights and protect their pretty girl. Along with the contrast of this pretty little thing standing beside them. A woman with a soft figure, soft tummy, squishy thighs, the whole works.

These men absolutely adore seeing their girlfriend in any clothes. Especially when it shows that bit of soft stomach. Even if you're standing there all insecure and unsure. He'll be trying his best not to drool. "I love it, princess", "God, you're gorgeous", "Makes you look like a goddess".

The intimacy is top notch. That one day you decided to wear lingerie for once? You'd never seen your boyfriend pop a boner so fast. He didn't even wanna take it off, just pushing it to the side and eating your pussy while holding those squishy hips of yours down.

Treats you like a million dollar work of art. Tells you how pretty you are and reassures every insecurity that you might have. Plus the perk of feeling security and safety anytime he's near.

Slowly erasing any derogatory statements you may have received before about your weight. Getting rid of that feeling that you can't wear certain things because he loves seeing those thick thighs in the shortest skirt you can find (if you're into that sort of style <3).

So yeah, muscular men and curvy girlies have my heart ❤️❤️

Thinking about.... Simon "Ghost" Riley, John Price, Nanami Kento, Toji Zenin, Sam Winchester, Dean Winchester, Leon Kennedy, Miguel O'Hara....and whoever you want <3

[seasonofthenerd]

Pov: You are the oldest Winchester kid

Aka Dean and Sam's Older Sister

PRE SEASON 1!!

Being dean and sam's older sister, John and Mary had you in 1976, 3 years before Dean was born, and 7 years before Sam was born

‌being 7 years old when Mary is killed by Azazel

‌Parentified soon after that as John became cynical with his revenge

‌Not being able to go to college due to obvious reasons

Going to Dean and Sam's ptms because John was absent father ™, and going to yours alone

‌Dropping Sam and Dean to school after passing out

‌Learning to drive and fix the impala at 15 from John because that'll help when you two are on hunts

‌Teaching Dean to drive when he is 16

‌Your relationships never work out

‌ Becoming a mom figure for Sam, and being Dean's support system

‌Being an expert at hunting and research

‌John taking you with him on hunting trips while Dean stayed back to take care of Sam

‌Having a lot of fights with John because of his behavior towards the boys

‌daddy issues™®©

‌Having many opportunities to run away and leave everything and everyone behind but not doing it for the sake of your brothers' future

‌Living in separate places than John after sam leaves for Stanford, providing dean with a safe place when he needs it, but still hunting with him.

I don't know if it's good it's just something I came up with randomly, if anyone reads please lmk if you are interested in more parts, thank you for reading!!

Also this is the first time I've ever written something and posted it on here (cries in panic and anxiety)

[sweetm0uringlamb]

fuck John Winchester. all my homies hate John Winchester.

[underwhelmingalchemist]

I love transmasc Dean headcanons because it implies that John was the world's shittiest father, but still drew the line at transphobia. Like, "of course I'm not gonna call him a girl, I'm not a monster. Now if you'll excuse me, I have a son to traumatize"

[angelsdean]

a very specific headcanon i have that i've just written into one of my longer wips (so you won't see the scene for an age) is that john is kinda a dick abt food and dean's eating habits. and he's just. so oblivious to the amount that his kids are suffering when he's gone. because dean sure as hell is not gonna bring up how the money is never enough, how they're near starving toward the end of some weeks. how they've relied on charity more than once. so when john comes back and gets them big full meals and dean especially practically inhales his food (bc he's hungrier, bc he's given more of his portions to sammy) john chides him to slow down, it'll make himself sick etc etc. but dean struggles. and he's always SO eager for burgers and pie and carb-y filling things. because he's starving. but he gets a reputation for "eating junk." john teases him for it. or berates him for it when he's feeling especially mean. when dean's older, stanford era, and they meet up for a hunt and get lunch dean still digs into his food a little too quickly, he asks the waitress for pie with a little too much gusto, and john shakes his head, laughing, saying it's a good thing dean's a hunter, it's a good thing he's got the grueling work to keep him fit or else all those burgers and pies would've definitely caught up to him by now. laughs at how dean still eats too fast, "you've done that since you were a kid. never grew out of it, huh?" and dean bites his cheek, bites back a remark about why he always ate so fast, why he's still always squirreling away food and jumping at every "free food" "free samples" opportunity even now when money is easier to come by

[frontseathater]

do you think dean ever saw john on the racks of hell?

do you think they were tortured side-by-side? do you think dean ever looked over at him and reminded himself that this was the eternity he deserved? do you think he reminded himself that he was made in his father's image and that he would never be more than that?

do you think dean faced him? do you think dean let the stench of hell fill his lungs as he tortured his own father? do you think he drank while he did it? do you think he held his weapons wrong on purpose? do you think he cried and screamed too?

do you think that's when he was saved? do you think the word of god wasn't enough to save him because he had made his god his bitch? do you think he needed more to know that he did not belong in hell? do you think he needed someone to look at him and say "i understand. i was made like my father too. let me reshape you with my bare hands and please reshape me with your soul. let me save you, and when you get out please save me too. let me show you what your purpose is. let me show you who you are. let me show you that life is what you deserve. i'll bring you up and you drag me down and let us anchor each other to what is real." do you think he leaned into the touch? do you think he remembered?

[ilovejohnwinchester]

Underrated exchange from 1x10. I think it really adds something to John’s character that for all he’s a hyper-competent hunter with a badass reputation, does what no one else can do, never backs down, never gives up, etc etc, the toaster wins every time.

I want to see more of John being just awful at technology. Can’t make a piece of toast without burning thirty slices of bread and his fingers in the process. Can’t ever figure out the TV remote in a new motel room. Picks at library computer keyboards with his index fingers. Hates to make counterfeit badges because he has to fight with the copy machine. Refuses to use email. Only ever bangs on things to try to fix them. Dean tells Sam their dad’s a superhero and Sam looks at John cursing at the toaster again and thinks, hm, maybe not.

[heliotrope155]

Watching that episode with the Khan Worm amongst others made me realize that Rufus, Bobby, Dean and Sam speak in a highly similar fashion (to various extents) of unique idiom usage or sentence structure (unlike Worst Grandfather of the Year and John Winchester). Is it canon that John used to leave the boys with Bobby and Rufus enough that the pair mostly raised them, taught them to research hunts by letting them help, taught them assorted things like car maintenance, bomb making, and first aid? To various extents. Do I consider it canon? Yes.

[castiwls]

"sacrifice, that's what we do for the people we love"

being the middle child in the winchester family...

I’d imagine you being like two years younger than Dean and two years older than Sam. So like literally the middle child

Your memories of your mum are fuzzy but you can recall a few things

When Mary died you were only two so you didn’t really understand what was going on for a while.

When you all first left Lawernce you spent most of that first night in a motel room crying because you wanted your mom and your bed. (Dean had to comfort you cause John left his two toddlers and baby alone in a motel #dadoftheyear)

When you were like ten your dad told you about what he had been doing for the past eight years. You were terrified but he made you promise not to tell Sam. He also made sure you knew that it was your job to keep Sam safe. 

Basically, you stopped being a child at ten.

You and your brothers were really close.

You and Dean basically trauma-bonded over hunting and also having wayyyy too much responsibility at a young age. 

Out of you and Dean, you were more emotionally available so Sam tended to tell you more.

As he got older he would talk to you about getting out and stuff. While your dad and Dean were very much into hunting you and Sam were more of on the sidelines. 

Sam got his love of reading from you. He’d always tell you about the books he was reading and what he was doing in class.

You’re the mediator for the family. It was always you who broke up fights. You were also able to calm your father down.

Mentioning in a passing comment that you didn’t want to hunt when you were like 15 and John flipped.

“If you don’t want to help kill the thing that killed your mom then you can get out.”

So you did. You left at 15 for 6 months.

In reality, you went to stay with Bobby but you never told your dad that.

Dean begged you to stay and would call every day. So would Sam.

Around this time Sam also started to want to leave. 

“I wanna come stay with you.” You sighed leaning against the wall. The phone rested between your ear and shoulder. “You can't Sam. Dad would flip your too young.” He let out a frustrated noise but let the topic go. (for now)

Dean would also call often and beg you to come home.

“Look he didn’t mean it, alright. It was just a heat of the moment thing.”

You did eventually come back. (Bobby wasn’t happy but let you go)

Your brothers were overjoyed and you actually got an apology from your dad (shocker.)

Things were ok for a few years and then Sam got a bit older and started talking about school. He’d only talk to you about it though. It wasn’t that Dean hated the idea but he didn't understand.

One day when you were 18 and he was 16 Sam asked to talk in private. So you took him to a dinner near the motel and he told you about Stanford.

“One of my teachers thinks it's possible.” He pushed the pamphlet towards you. “I just need a signature from an adult and I know Dad won't sign it.” You quietly looked over the pamphlet for a moment. A sense of pride washed over you as well as relief. This was his way out. “Of course, I’ll sign it.”

You both kept it quiet for the next year and when his acceptance letter came in you both kept it to yourselves but you were so proud

#proud parent moment.

Though eventually, Dean found the letter. 

“Did you know about this?” He asked holding up the letter. You felt your blood run cold as you grabbed the letter from him. “Yes. I did know.” You admitted. “It was me who signed the papers.” Your brother's eyes widened a look of betrayal crossed his face. “Why would you do that?” His voice began to rise as he spoke. ��Because Sam deserves a future Dean.”

You two didn’t speak for a while after that. Dean got over it though.

When it came time for Sam to leave that's when all hell broke loose.

You’d never heard your dad yell so loud. He and Sam went back and forth for hours until your younger brother just walked out. You and Dean both followed him. After calming him down you went with him to the bus and said goodbye.

Dean was kinda non-plussed (inside he hated it and was worried sick). You were worried but happy that he was getting out.

When you and Dean went back to the motel John was furious. He blamed you (of course)

“This is your fault. You're the one who put all those ideas in his head and look what happened.”

Dean jumped in front of you and told him to back off. 

“Sam’s his own person you can’t blame her for this!”

After this, you and Dean get closer. John starts taking more hunts alone meaning that you and Dean spend a lot of time just driving around.

You would probably class this as the first time in your life you felt truly happy. Hunting with Dean was easier and there were fewer arguments.

Sam would call u often to update you. When he told you that he’d met a girl you were so happy for him. (it really seemed he got out)

But then your dad went missing and Dean insisted on getting Sam to help.

You were glad to have both your brothers back but at the same time felt insanely guilty as you watched Sam fall back into hunting.

[smollkittykat]

Sam sits on the edge of the hotel bedroom, his entire body is shaking, as he silently stares at the door, Dean had slammed closed after shoving him into the off-bedroom.

"Let me handle him. I am the one who screwed up. Just stay here, till I open the door, alright?", his older brother had said. And Dean was ten already, and always watched out for him, so Sam nodded, not quite trusting his voice.

And now there's shouting. muffled by the wooden door but still crystal clear. Sam carefully reached to cover his ears, terrified that the movement would cause any sound that might shift the attention to him.

It didn't help. No matter how hard he pressed his palms against his ears.

"Dad, please, he was just worried about us-"

"Boy, you better move from the door. now."

"listen, it's my fault he even caught wind of it, okay?

The recoil of the gun still ached in Sam's lower arms, his elbows stiff. He had just tried to protect Dean.

He saw him when Dean lost his gun. And the deer had heard and snapped up at Dean and it was so big and scary and fast and it terrified Sam that it could hurt Dean and so Sam had scrambled for the gun, while his big brother was still distracted and shot at it.

Once, twice ? Sam wasn't even sure.

Dean's voice picks up again, this time, Sam can't make out what.

Whatever Dean said, must've been the wrong thing, because the next thing he hears is a loud slap and something collides with the door Sam sits behind.

Dad keeps yelling.

Sam hates him. He hates him so much.

his grip shifts and he clings to his short brown hair as he hears the first crack of a belt.

Dean doesn't scream, doesn't cry.

"I'm sorry, sir." He hears him instead.

Sam will never be as brave as his older brother, he thinks as tears run down his round face.

[marunene]

Ok, since most of the time neurodivergences like autism and ADHD are hereditary, I thought about a headcanon for the Winchesters

Autism: John → Sam

ADHD: Mary → Dean

[supernaturalkickparty]

Speech Delay Sam who didn't start talking till he was 4 or 5.

His stuttering was worse when he was younger and he had the hardest time pronouncing certain words.

I'm thinking of when they were teenagers, Dean and him arguing and John is just kinda over it. He's letting them fight it out when Sam's stuttering over some words when Dean laughs and tells him that he ain't got all night to argue with him and Sam's just so frustrated he swings at Dean knocking him flat on his ass.

Dean's is caught off guard and John's just sitting there like