My Best Friends Brother // Supernatural
Jackie-Santana
  • Reads 6,721
  • Votes 261
  • Parts 101
  • Time 9h 11m
  • Reads 6,721
  • Votes 261
  • Parts 101
  • Time 9h 11m
Jackie-Santana
Complete, First published Feb 12, 2023
Mature
bestcastieldeanwinchesterfanfictionfriendslovesamwinchestersupernaturaltexttospeech
Being Sam Winchesters oldest friend must've been one of the best things to have happened to me, growing up together, going to school together, then off to college we went. Practically inseparable. Growing up we only had two rules, never lie or keep secrets from each other and the biggest one, don't ever fall in Love with Dean.
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Table of contents

101 parts

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Chalk & Chainmail by angelwingsandthings
11 parts Complete
At eleven years old, Dean Winchester thinks he and Castiel will be best friends forever. One day, however, when Castiel shatters their friendship in one easy swoop, Dean finds himself fearing nothing will ever be the same between them again. Now seven years later, their paths cross again and together they find themselves figuring out who they truly are and who they were meant to be.
Dean Winchester's Daughter by MarvelousWriter14
13 parts Complete
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Castiel's Lover|Supernatural Fanfiction (The Isabella Series) by HisKoala2003
14 parts Complete
Sam Winchester and Dean Winchester, the two brothers as they hunt demons, ghosts, monsters, and other supernatural beings they also have a bestfriend named Castiel who's an Angel of the lord. One day the brother's meet a 25 year old girl.What happens when they find out her and Castiel are bestfriends?What happens when life becomes a rollercoaster?....Read to find out
You're my monster (Dean Winchester x Werewolf Reader) by anonymous4uthor
16 parts Complete Mature
You are Bobby singers daughter, met Dean Winchester and immediately fell in love. Bobby reluctantly let you come on a case with them, in which you got hurt. Dean however, always believed in you which made you fall in love with him even more.
Reminiscent by idkbaands
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we were just two kids in love ≫ dean winchester a.u.
The life of a hunter (Dean Winchester love story ) by VampireHunter1
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Katelyn Mariah Walker is an incredible hunter. Growing up as the best friend to the winchester's is not an easy task. Kate always felt a romantic pull towards Dean, while Sam was like the brother she never had. When Dean calls and asks for her help finding John, she picks up a pistol and hits the road. Will the relationship of these childhood friends develop into somthing more during this road trip?
No Regrets ~ Dean Winchester by countryqueen20
32 parts Ongoing Mature
The Winchester brothers had been on the road together since their father had gone on a hunting trip and hadn't been home in a few days. They end up seeking the help of a family friend when their father runs into some trouble, meeting a new face along the way. Dean wouldn't know what hit him when meeting this new face, but he would never regret it. Alexandra had heard of the Winchesters before meeting them. She didn't know what she was getting herself into, but she would never regret it.
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A life with winchesters and their guardian angel.
Changes (Dean Winchester X Reader) by irvncap
16 parts Complete
You are an immortal being, not limited to a species because even the Archangels have no idea what you are. Your only friend is Castiel, when he has time to visit. Even though you are over 6 million years old, you have very little control over your powers, so you stay inside to protect the humans from you. Then Castiel lets you meet the Winchesters, and your new life begins. I don't own Supernatural or any of the characters though I wish I did.
Dance With Me {Dean Winchester X Reader} by irvncap
27 parts Complete
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Sam and Dean have a foster sister that is 14 years younger than Sam.
Keeping up with the Joneses by arconrad
23 parts Complete
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How It All Started (Dean Winchester Love story book 1) by Emma_s_21
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Skye and Dean have been best friends since they were kids. John Winchester took her with him and his family after a hunt gone wrong with John Winchester and Skye's Parents. Years later Skye still has been by Dean's side slowly falling for him. Sure she get's jealous when he is always having his one night stands and flirting with women but she can't help it cause she is scared of losing him. She tries to put her feelings aside because they have bigger things to deal with and that's to find John Winchester.
Old Friends by Fitchingoodstories
8 parts Complete Mature
You run into a hunter you had been best friends with and immediately its like no time has passed, as you two catch up Dean becomes jealous of how close you are. Warning of smut content Note: I do not own any characters or prompts that the Supernatural writers created, only thing I claim is my interpretation of the plot :)
The Older Sister by AlexisMaxwell667
16 parts Complete Mature
dean isn't the oldest Winchester their sister Kate is and she just got back from her last tour in the military and while Sam gets back in the game of hunting after college they go on cases together and try to find their father and find interesting things out about Kate's past I DO NOT OWN SUPERNATURAL OR ANY OF THE CHARACTERS OTHER THAN KATE SHE IS MY CHARACTER THAT I MADE so please enjoy
He's My Angel ♡ (COMPLETED) by 1967chevyimpaiws
16 parts Complete Mature
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Freedom of Fate ~ Castielxreader by MishasBadButtv2
20 parts Complete Mature
Castiel is your best friend, but maybe you were always meant to be more. You've been hunting with the boys for years, but when the dynamic between you gets too complicated, you begin struggling to cope. You wonder if it's time go your own way, but there's something - someone - stopping you. Eventhough Cas is the main direction, I'll make sure to include lots of cute moments with the Winchester Brothers too.
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My Cousins Best Friend Dean X Reader by Hannahbanana_xx03
35 parts Complete
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Blood (Castiel X Reader) by Mentally_Unstable101
29 parts Complete Mature
When your mother is mysteriously murdered by demons and you're raised by a hunter from the age of ten, what could go wrong? After Matt is killed you turn to his only friend, Dean Winchester. His brother and his Angel both sense something about your blood. Will they give you shelter or use your blood like a drug?
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Slide 1 of 20
Chalk & Chainmail cover
Dean Winchester's Daughter cover
Castiel's Lover|Supernatural Fanfiction (The Isabella Series) cover
You're my monster (Dean Winchester x Werewolf Reader) cover
Reminiscent cover
The life of a hunter (Dean Winchester love story ) cover
No Regrets ~ Dean Winchester cover
Supernatural cover
Changes (Dean Winchester X Reader) cover
Dance With Me {Dean Winchester X Reader} cover
young and supernatural 1 cover
Keeping up with the Joneses cover
How It All Started (Dean Winchester Love story book 1) cover
Old Friends cover
The Older Sister cover
He's My Angel ♡ (COMPLETED) cover
Freedom of Fate ~ Castielxreader cover
Sage Winchester cover
My Cousins Best Friend Dean X Reader cover
Blood (Castiel X Reader) cover

Chalk & Chainmail

11 parts Complete

At eleven years old, Dean Winchester thinks he and Castiel will be best friends forever. One day, however, when Castiel shatters their friendship in one easy swoop, Dean finds himself fearing nothing will ever be the same between them again. Now seven years later, their paths cross again and together they find themselves figuring out who they truly are and who they were meant to be.

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