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deanjess / jean headcanons i wrote at 4am
jess goes to all of dean's games, even though he hates strongly dislikes his teammates
dean makes ridiculous orders at luke’s just to tease jess
“i want a tiny pancake house with a chimney.”
“does it look like i'm a fucking architect to you?”
jess pushes dean to explore, dean prevents jess from accidentally getting arrested
dean always defends jess during the town meetings, even if he doesn't think jess did the smartest thing
jess watches the lord of the rings trilogy with dean when he’s sick
“you know the books are way better though, right?”
dean thinks that he’s too boring for jess, but jess couldn't imagine himself with anyone else
jess can’t stare too long at dean while he's working on a car. (dean knows exactly why jess gets stuck on the same page whenever he’s there)
dean keeps jess motivated enough to graduate high school
jess takes dean to his first gay club (in new york city)
“don’t you chicago people have boystown?”
“jess i haven’t lived there since i was like 14!”
dean makes short jokes all the time (jess makes tall jokes even more)
jess tutors dean at the diner, but uses that as an excuse to make out with dean upstairs sometimes
every year, taylor begs them both to help lead a pride parade for the town, they always find an excuse though
"sorry taylor, but dean's aunt's friend's daughter's coworker's pet goldfish just died, and we just have to go to the funeral, you understand right?"
they call each other at night just to talk about mundane things as an excuse to hear the other's voice
dean loves the look in jess' eyes when he talks about his favorite albums
jess feels trapped in stars hollow, but feels free whenever they're together
dean builds jess a car for one of his birthdays
“promise me that you won’t crash this one?”
“you know i can’t do that.”
“jess i’m serious!"
what truly piques my interest with winjess is when hate-fucking is involved…dean referencing jess as sam’s sloppy seconds…dean referencing sam as jess’ sloppy seconds…dean viewing them both as anatomical instruments to fulfill sexual gratifications
hes just so tiny all the time …
deanjess collar time

Anya is live and ready to show you everything. Watch her strip, dance, and perform exclusive shows just for you. Interact in real-time and make your fantasies come true.
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New fic is live!
"John and Mary Winchester have three children: Dean Michael, Jessica Lee, and Samuel William.
Still, you can't spell Winchester without incest."
Very loose season one with Jess as a Winchester sibling!
An Archive of Our Own, a project of the Organization for Transformative Works
I have so many thoughts about DeanJess, Jean dare I say
Hey, I wanna try writing some short Dean Forester x Jess Mariano fics/drabbles, so if you have any ideas/prompts/etc. you want to throw my way please either reply to this post, message me on here, or reblog this post with your idea.