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#dean headcanons
THIS IS BASED OFF A TIKTOK I SAW BUT IMAGINE THIS IF YOU WERE THE BOYS’ YOUNGER SIBLING
Dean: Hey kiddo, how was school?
Y/n: it was good i met a boy today!
Dean: …
Sam: …
Dean: oh yeah? what uhh what was this boy’s name?
Y/n: his name was michael and he told me he likes me!
Dean & Sam *panic*: …
Y/n: we held hands and everything!
Dean & Sam: *look to each other* YOU HELD HANDS???!?!?!??
Y/n: yeah :D
Dean: oh no, oh my god, Sam..you know what we have to do…
Sam: agreed.
Dean & Sam: *grab Y/n and carry them to the sink, and stick their hands under the faucet*
Dean: SANITIZE! SANITIZE!
Y/n: *uncontrollable laugher* no! it was only for like five minutes!
Sam: Five whole minutes!!!! This calls for the holy water…
Y/n: *dying laughter with hands still under running water*
RAHARAHARAHARAHARAH im feral for this hc
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alexsoenomel · 1 year
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Jamming with Dean Winchester in the Impala would include:
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“Driver picks the music-”
“Shotgun shuts his cakehole! Yes, Dean I know!” 
You being irritated.
Dean not letting you pick the song you want 
Always bickering over who will play the next song 
“I want Pink Floyd!” You demanded. 
“And I don’t want to get depressed, (Y/N)!” 
Dean putting Zepp’s Ramble On
You rolling your eyes in protest 
“How many times are you going to listen to this one?”
“Oh come on, (Y/N)! You love this band just as much as I do!”
“There are far better songs than Ramble On though!”
“Oh yeah? Tell me Ms. Expert!”
“Living Loving Maid? Black Dog? Rock and Roll?” 
“Living Loving Maid is a nice choice!” 
“SEE? I know a thing or two about Led Zeppelin!” 
You eventually caving in and actually singing the lyrics 
“ Ramble on And now's the time, the time is now To sing my song I'm goin' 'round the world, I got to find my girl On my way I've been this way ten years to the day Ramble on Gotta find the queen of all my dreams.”
Dean joining you 
For a second you both forgetting you’re going on a hunt 
“Can I chose the next one?” You asking nicely once the song is finished. 
“FINE!”
You putting on Heaven and Hell by Black Sabbath 
“OOOOOOH NICE ONE, (Y/N)!”
“Since you don’t want Pink Floyd....” 
You putting your sunglasses on, completely dissociating and enjoying the song 
Dean feeling the dopamine kicking in, jamming with his hands on the wheel 
Both of you singing the your favorite part 
“ And they'll tell you black is really white The moon is just the sun at night And when you walk in golden halls You get to keep the gold that falls It's Heaven and Hell, oh no  Fool, fool You've got to bleed for the dancer”
Yelling the last part of the song 
“Fool, fool Look for the answer Fool, fool, fool”
“Your turn, Dean! And if you put on Traveling Riverside Blues I’m gonna scream!”
“Okay, okay! Metallica?” 
“Sure!” 
Dean choosing Enter Sandman 
“God, I used to have the biggest crush on James Hetfield.”
“Used to?” 
“Yeah still do. That man can make me do anything with that voice.” 
“You’re gross!” 
“And you talk to much!” 
You blasting the volume 
“ Exit light Enter night Take my hand We're off to never-never land “
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trailerprk-princess · 2 years
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—dating dean winchester | dean winchester x fem!reader headcanons
!!!: my work is not to be reused without credit/permission!
request rules
warnings: nsfw & mentions of drugs! minors dni! fluff & not edited
authors note: im really obsessed with him rn🫣 requests are open!
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he is so desperate for your love & attention that its kinda concerning. he never got love growing up or has been involved romantically with anyone for long & he is used to one night stands that dont go anywhere. so its very refreshing to him to have someone being as equally in love with him as he is w u
he is very hesitant to talk about his feelings & past to everyone, including to those he loves. but you really get him to open up to you about those things. which is really good for him bc he learns that his dad was a shit father & he finally gets to know what real love is. & what it actually feels like to have someone be concerned & care for him. & he knows that he doesnt have to hide anything from you bc you wont judge him or think of him any differntly
when sleeping next to him, he finds it very hard to let you go from his grip. hes very touch starved & craves any touch he can get from u. whether it's spooning you, putting his hand on ur thigh, or just holding ur hand
he is a very conflicted person. almost in every episode he thinks something is wrong w him bc he "enjoys" killing. but it really is bc hes pushed aside every emotion he has ever felt & doesnt deal with them. him being with someone who is willing to listen to his vulnerabilities really helps him figure himself out
he is a VERY loyal person & boyfriend.
he likes to give gifts & is very close to being ur sugar daddy from how much money & gifts he gives u bc he thinks that the only way to keep u around is to give u everything u could ever dream of. which is very unhealthy thinking on his part
he needs CONSTANT reassurance. he needs to know that you will never leave him for someone better. believe it or not but hes pretty insecure. hes not insecure of his abilities in bed or looks but insecure of his lifestyle
he gets you little souvenirs from every state he visits! & now u have a whole bookshelf of knickknacks
type of person to tell u that he loves u within a week of dating. im half joking but he falls for people very easily
hes pretty controlling & protective of u, he just doesnt want you to get hurt. he will not let you go hunting with him, anyone, or alone. he needs you to be safe at all times. which yes, is understandable but you have to tell him that its toxic when it gets to the point hes too nervous about you leaving the bunker, your house, motel, anything really. & there's probably a tracking device in ur bra
he never smoked marijuana or says he does in the show. but everytime he sees a bong hes gets weirdly excited so i think hes a pot smoker. which is nice! bc hes very good at getting you strains of marijuana that r good for u & fit ur needs. he rolls ur blunts/joints for u!! & he even lights them for u as well! smoking weed is a huge part of his aftercare for u as well bc it helps to calm u down
he is very casually dominant! he orders for u, ties ur shoelaces for u, takes away ur soda if uve had too much, denies chocolate from u if u have too much cause he needs u to be healthy for him & eat right. he turns off the tv at the same time every night & makes u go to bed. he doesnt like it when u cuss & gets on to u everytime that u do cuss. he likes to pick out ur outfits as well. he also doesnt let u drink due to the fact his father was an alcoholic
he teaches u how to play pool & poker!! & even takes you out shooting every once in awhile!
he has the BIGGEST innocence kink known to man. he literally loves taking virginites
he literally has an angel kink. theres nothing that screams innocence/corruption kink more than that
he likes to dress you up as an angel too!! white lace lingerie & it would get him going more if he could get you to wear a halo headband!
his literal petname for u is, 'angel.' inside & outside of the bedroom. youre just so sweet & precious, how could he not call u angel??
literally just wants to corrupt u everytime he has sex w u. taking your innocence or making you look innocent while doing a not so innocent activity
a lot of people think hes a switch but i dont think so tbh. he literally has no control in his real life which would make him more likely to want control in the bedroom. not saying he tops everytime but theres no chance i can see him giving up his domination/control
but what i do know for sure is that this man is a FREAK
his list of kinks is longer than the amendments on the bill of rights
breath play, bondage, knife/gun play, impact play, corruption/innocence kink, praise/degradation kink, literally anything if youre down
i mean. he is horny 24/7 so it is for certain that he would try anything once or do anything sexually w u as long as u liked it
he LOVES to praise u! youre his 'pretty baby' or 'good girl' but he also LOVES to get praised too. he needs to know how good he is doing
but there are times that hes very degrading, usually when he has had a bad day. because u can be his 'good girl' one day & the next youre his 'dirty slut'
he is also a brat tamer! if your acting too bratty he will bend u over his knee
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dean winchester masterlist
masterlist
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emeraldsummers · 26 days
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Smoker!Dean headcanons (aka if Dean was a smoker throughout the series)
As a teenager, Dean would smoke whenever he could get his hands on a cigarette, but it was pretty rare. Money was too tight to buy them, and it wasn't worth the risk of stealing them, but occasionally, Dean was able to trade for loose cigarettes. He loved the head rush and loved feeling like an adult.
Pre-series, Dean didn't start smoking in earnest until he started doing hunts without his father. John didn't like the smoking, so Dean hid it from him. Still, money was tight, so Dean only smoked a few cigarettes a day at most. His favourite thing in the world was being whiskey buzzed and sharing a cigarette with a girl.
Dean never, ever smoked inside the Impala.
Seasons 1-2 Dean is still smoking a few cigarettes per day, properly addicted at this point, and irritable when he isn't able to get a smoke break. Sam is constantly bugging him to quit, and Dean pretends he could quit any time he wants to. Sam gets non-smoking motel rooms whenever he can, which annoys the hell out of Dean.
Season 3, with the demon deal looming, Dean starts smoking more now, and by the end of the season, he is fully chain smoking regularly. Sam finds it gross but generally allows it to slide because he knows Dean needs it.
Season 4, Dean comes back from Hell with zero physical dependence on nicotine and decides to treat it like a fresh start. He doesn't smoke. He uses his experience with smoking to try (and fail) to empathize with Sam's blood addiction.
Season 5, Dean starts smoking when he's drunk, which turns into smoking when he's stressed, which by the end of the season, when he almost says "yes" to Michael, turns into him smoking all of the time again.
When he lives with Lisa and Ben, he tries to quit for their sake, but he still sneaks a cigarette outside on really bad nights. Lisa pretends not to notice.
Season 6, the smoking continues, but not as heavy as season 5. Sam is actively annoyed about it at this point, and Dean has long stopped finding smoking to be fun.
Season 7, as Dean spirals downwards after Cas' betrayal, he smokes much more heavily. It's starting to affect him physically, especially without Cas to heal him. He starts saying things like, "I'm getting too old for this." Since he isn't able to drive the Impala for most of the season, he smokes in the cars they steal, which really bothers Sam.
In Purgatory, Dean has no choice but to quit cold turkey, which is miserable, and once he's home, he continues that streak into seasons 8 and 9, his longest smoke-free period.
Unfortunately, demon!Dean picks up smoking again, and even when he's cured, smoking becomes one of his coping mechanisms for quelling the Mark.
Seasons 11 and 12, he struggles with trying to quit, going anywhere from days to months at a time without smoking before falling back into it. When Cas dies at the end of season 12, he begins chainsmoking again along with regularly getting black-out drunk, and Sam really worries for his brother's health.
After Cas returns in season 13, Dean begins working to quit again in earnest, creating a system with Sam, Cas, and Jack's help. This time, it sticks through the end of the series, but Dean does heavily consider starting up again as he spirals towards the end of season 15.
Post-series Dean is trying to maintain being smoke-free, especially since Cas is gone and Jack is hands-off. He knows any damage he does will be permanent this time, and he doesn't particularly feel like dying of cancer. But it turns out the boredom of the world not ending is worse for his cravings than the stress was. He starts smoking weed, trying to convince himself it's a proper substitute, but eventually, he just smokes weed because he likes it.
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iliketoydinosaurs · 1 year
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If Dean isn't trans then why "I had to be a mother to keep him safe. And that wasn't fair."
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softhazyalone · 5 months
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There has never been and will never be again a man that has me kicking my feet, foaming at the mouth, delusional like Dean Winchester.
The self loathing, the repressed emotions, the caring older brother, grew up too fast, never had a chance, his best is never enough, devoted to a cause, standing for nothing dying for anything, yearning for something he will never let himself have, giving love in the small details, the weight of the world on his shoulders, unwavering dedication to a fatally flawed father, self-sacrifice to the point of self-destruction, bone-weary, never enough, too much, a broken promise to never be vulnerable again, “you can have mine”, he would do anything to save you but he cannot save himself, thinking he is a means to an end, hands reaching out to grab with closed fists, stubborn, flawed, righteous, devoted, re-born, self-made, risen, human…………
I could quite literally go on forever, I have clinical Dean Winchester brain rot and there is no cure.
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Dean: "Has anyone seen my flannels? I just bought three of them and they're gone"
Sam: "Don't look at me I have my own I know how you get when someone touches your stuff"
Castiel: "I do not know what flannel is"
Y/N walking in wearing only a flannel with the top buttons open, dancing listening to music
Dean smirking: "Cutest thief ever"
Y/N totally oblivious: "What?"
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habrabbit · 10 months
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literally!!!!!!
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peanutmcqueen · 11 months
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Im fascinated by dean's love of Ramble On and * parallels *. The way it starts cool and easy, the domestic life dean really wanted.
But now its time for me to go - he comes back to reality, his life as a hunter,
Now i smell the rain and with it, pain And its headed my way - all the horror and struggle with hunting, still haunting him,
Ive been this way ten years to the day - the way this life took away crucial years and more from him,
Got no time for spreading roots - never had the time or freedom of setting down, getting what he really wanted,
But i know ive got one thing ive got to do Ramble on -
"Dean's very focused on the task at hand because thats what he can do" -Jensen Ackles
Ramble on Dean.
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given that he grew up a normal life…
also these jobs are general examples, i dont know entirely enough if they are accurate
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marcskywalker · 1 year
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headcanon for writer/lyricist dean is that his writing style relies heavily on metaphors, parallelisms and subtexts. Because homeboi is incapable of saying what's in his heart as it is.
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peachyaliien · 2 years
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Had this idea for a while so I wanted to share it (even if i’m sure it has been done already but heh). I just felt like doing something cute and wholesome (in a Dean way)...
Also tagging the amazing @all-alone-he-turns-to-stone​ ♥
Reblogs and comments appreciated!!
Going on a roadtrip with Dean Winchester would include...
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Feeling like you are finally free from the hunting, away from all the deaths and torture you both endured. Feeling like two teenagers deeply in love, free to do whatever they want during summer break and just enjoying life.
Singing at the top of your lungs old songs together, going from Guns n Roses, to Led Zeppelin and Survivor.
Stopping at convenience stores to get supplies, food, drinks and snacks. 
Stopping by touristics spots all around the country, like the Roswell UFO Spacewalk, and enjoying the urban legends around some of them.  
Flirting with each others like the first time you’ve met, telling each others bad jokes and puns, making each others laugh and enjoying each other’s presence like it’s your last days together.
Laying on the top of the impala to look at the clouds or the stars together. Your bodies close to each others, fingers intertwined together as you’re holding hands.
Camping together. Dean stopping the Impala in a quiet peaceful spot, making a little campfire so you can make s’mores and rosting marshmallows. Him putting his leather jacket around your smaller frame, his arm around your shoulder, holding you close against his chest while telling you stories about his childhood. As well as wanting to hear more about your interests, your hobbies, your dreams, you. Because even if he doesn’t always say it outloud... you are his light of hope in this damned world.
A whole lots of kissing. Kissing your knuckles while driving, blowing you kisses while glancing at you, kissing his cheek when he’s driving more slowly on the peaceful road, passionnate kissing when he can finally park his car...
As well as long passionate love making sessions in the back of the impala, allowing the both of you to take your time to enjoy the feeling of your warm hands on each other’s body. Some times even making love on the top of the impala, depending on your moods and needs...  
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Supernatural Masterlist: here!
Main Masterlist: here!
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destiel-wings · 22 days
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the craziest thing about the mixtape is it sets up a precedent, we had no idea dean gave it to him because it didn't happen onscreen, we only knew about it because we saw castiel trying to return it.
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so how many other gifts may dean have given castiel that he just kept?? whose gifting or returning wasn't crucial to the main plot and so we didn't get to see??
how many destiel scenes happened offscreen during all those years?? another example of this is them watching tombstone. so many little throwaway lines or moments here and there that basically confirm that for as much insane couple behavior we saw onscreen, there was a whole other level of offscreen insanity going on
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strawlessandbraless · 1 month
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Possessive Castiel with a marking kink makes me feral
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