1 - 20 of 422 Works in Dean Winchester and Sam Winchester and Original Female Character are Siblings
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It starts with a life she can't remember. Raised a hunter, Gracie is convinced she wants to be normal. But that's not something a Winchester, let alone an empath, gets to choose.
Or, on May 2nd, 1983, Sam and Gracie, the Winchester twins, are born. Sam has been marked from infancy for a dark destiny that could destroy the world, while Gracie’s strange powers and odd visions make her wonder if she’s really who she thinks she is, or even human. Together along with their brother Dean, it’s the Winchesters against the world, out to rewrite “fate” or die trying.
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When the Levee Breaks, It's All My Fault by green_tea_bag
Fandoms: Supernatural (TV 2005)
02 Oct 2025
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Summary
Dean comes home with Sam in tow and throws him into the panic room in Bobby's basement. Their little sister is scared, confused, and angry. She doesn't know what's going on, she doesn't know what to do. And her brother is screaming for her to let her out.
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Sam and Dean's little sister let's Sam out of the panic room and it all goes sideways.
Series
- Part 27 of Celeste Winchester
- Language:
- English
- Words:
- 1,948
- Chapters:
- 1/1
- Kudos:
- 7
- Hits:
- 154
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After storming SucroCorp and ganking Dick Roman, Dean Winchester wakes up in Purgatory and Mercy finds herself in Crowley's custody.
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"Dean had survived a childhood with John Winchester as his father... Purgatory was a different beast entirely." & "It was then that Mercy realized she was in trouble. However safe she’d felt, she was still in enemy territory. However comfortable the hotel room was, it was still a place she was not allowed to leave."
(aka, the year between season 7 and season 8 told in a consolidated story as opposed to a series of flashbacks)
Series
- Part 5 of Quality of Mercy
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Katie lies and gets herself into trouble with some vamps. When Dean drags her home, she tries to refuse the spanking she knows she has coming to her. Dean, of course, will not abide. He drags her over his knee and gives her what she's got coming.
Katie is about 18 and the deal is that when she lies, disobeys, or puts herself in danger recklessly, she earns a spanking from Dean. Those are the rules Dad left them with, and Dean obeys dad's rules.
Series
- Part 4 of Oldest Son
- Language:
- English
- Words:
- 1,895
- Chapters:
- 1/1
- Kudos:
- 5
- Hits:
- 183
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Summary
Part 4 of the 'Quality of Mercy' series
“I'm glad you made it, Sam, Mercy. But the angel blade won't work, because I'm not an angel anymore. I'm your new God. A better one. So you will bow down and profess your love unto me, your Lord. Or I shall destroy you…”
(a rewrite of season 7)
Series
- Part 4 of Quality of Mercy
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Rūta is digging further into a reckless path and is up to Sam and Dean to stop her, even if that means putting the young sister over their knees.
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Celeste pushed past him into his room and looked around, gathering courage. “I’m sorry if this is…I’m sorry if you don’t want to answer. You don’t have to. But I just…wanted to know…I mean, you were going to marry Jessica, right?”
Sam Winchester's little sister ponders about marriage. Feelings ensue.
Series
- Part 23 of Celeste Winchester
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Summary
Everything in Ellie’s life has been normal for the six years she’s been alive—all six years of it, and yesterday wasn’t supposed to be an exception, but it was far from it. It was significantly worse than normal. She herself didn’t want to believe it, hoping that this was one of her nightmares and that she would wake up any minute.
Ellie was shaken back to reality when John Winchester spoke up. He had saved her life. So there she sat, at the back of his car while he drove to someplace that Ellie didn’t even care to know about right now, because even though her mother taught her not to talk to strangers, much less go with strangers– this man was very much not a stranger.
John Winchester saved her life.
Series
- Part 1 of Second Chance
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Summary
Reader is Dean and Sam's Sister. 2 yrs younger than Dean and 2 yrs older than Sam. Stuck in the middle. You were only 2 when your mother died. So your memory of her is very limited. Just certain things, the way she smelled, her smile. You've been brought up to hunt Just like your brothers. But Dean was Dad's little soldier, and Sam was the rebel. You were just there. That's how you felt anyway. So When Sam calls you to say that Dean is in trouble a part of you wants to tell him so what. But the Winchester in you says You don't turn your back on family.
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Dean, Sam, and Katie reunite with John in Lovelock, Nevada to look into a series of grave robbings. Dean is just trying to keep everybody level - keep Sammy from losing it with John, keep Katie from losing it with both of them. But when the boys leave Katie alone in the motel room, a stranger comes knocking. John doesn't like how Katie handles it, and he blames Dean (of course.) Dean has to take a belting in front of his siblings. It's traumatic for all of them.
Dean is 20, Sam is 16, Katie is 12.
Series
- Part 5 of She Rides Shotgun
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Summary
“No.”
That was the only word out of Dean’s mouth before he ran a hand over his face, grabbing his duffel. “You’re staying here, in this motel room. If you so much as a step one foot out of here-”
“I know, Dean.” June rolls her eyes, twisting her leather bracelet around her left wrist. “You’ll find out and ground me. I’ve got it.”
Dean just stares June down for a moment longer, June refusing to be the one to break eye contact first, before he shakes his head, nodding for Sam to head to the Impala. Sam pauses at the door, catching June’s eye, and with just one look she knows what she has to do. “We’ll be a couple of days, max.” Dean gestures to the wooden bedside table where her Blackberry lies, the battery flat. “Keep your phone on.”
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June tries to find a way out of Dean’s deal. It doesn’t go to plan.
Series
- Part 5 of june
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Summary
Sam comes back to the motel room drunk. Dean and their little sister Celeste share a worried conversation about Sam’s state of mind.
Series
- Part 22 of Celeste Winchester
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Just little fluffy scenes of different birthdays throughout Celeste's (Sam and Dean's little sister) life. Sam and Dean are amazing siblings and Celeste is finally happy????
Series
- Part 21 of Celeste Winchester
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Summary
Born of Heaven. Haunted by Hell.
Raena Winchester has been trained to be a hunter since she was a kid—to protect her siblings and save lives. But the world is changing, and there’s more to deal with than just monsters. When her brother returns from the grave after being dead for months, everything she thought she knew begins to unravel. Now, Raina finds herself in uncharted territory: fighting angels, striking deals with demons, and standing toe-to-toe with the devil himself. If that wasn't enough, something is awakening within her—powers that could shift the fate of the world.
As her connection to Castiel grows and Lucifer closes in, Raina must face a choice: remain the protector she's always been, or embrace the warrior she was fated to become. Because in the end, she might be more than a sister. More than a hunter.
She might be something divine.
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The Name is y/n Winchester. (But every one just calls me Sweets.) Twin sister to one Sam Winchester, Little sister to Dean Winchester. When my mom died I was just a baby. I don't even remember her, or a life outside of hunting. I can't say I enjoy hunting monsters, but hey it's the family business so what are you gonna do?
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An unexpected run in with a djinn sends Crowley into the life of his dreams married to one Y/N Winchester. Will the King of Hell wake up in time to save himself? Will he want to wake up even if remaining in his ideal dream life kills him? Waking up and facing reality just might mean confronting the complicated status of whatever has been happening between him and Moose and Squirrel's lovely sister. Crowley has never done well with feelings given his demonic nature and Y/N's brothers aren't quite accepting of his fondness for their beloved sister. Perhaps a dream where he gets to have the woman his heart desires is worth it even if it's not real? Is facing reality a risk the King of Hell is willing to take? Not all in this fantasy world is as it should be, but is Crowley willing to risk facing the truth?
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Summary
Sam and Dean's little sister gets hurt on a hunt and has scars. She’s self conscious and Sam and Dean try to make her feel better about it. Her girlfriend helps, too.
Series
- Part 20 of Celeste Winchester
- Language:
- English
- Words:
- 1,813
- Chapters:
- 1/1
- Kudos:
- 5
- Hits:
- 181
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Summary
With the death of the love of his life, Sam Winchester fights to get revenge on the thing that killed his girlfriend while protecting his 18-month-old daughter. Luckily his brother, Dean, and best friend, Cameron are along for the ride to help him out.
Supernatural-Season 1-3
Book 1 of the Charmaine Winchester seriesSeries
- Part 1 of Wings of the Abyss
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Summary
Frankie Pearce has been through Hell. Literally. It was a struggle to go through the aftermath without her family, but she had her best friend Castiel by her side through all of it. Now, she has decided that the time has come to reunite with her brothers, Sam and Dean, to help them defeat Michael and Lucifer and stop the Apocalypse.
But Frankie soon finds that the path back to her brothers is not one easily tread. Powerful foes are determined to use her for their own gain. Frankie must find a way back to her family, no matter the cost.
Series
- Part 8 of Two and a Half Winchesters
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It's nothing but some feelings by ablatheringblatherskite
Fandoms: Supernatural (TV 2005)
18 Jun 2025
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Summary
Sam and Dean's younger sister, Ettie, quickly discovers the injury Sam has been hiding and confronts him about it.
Series
- Part 2 of June of Doom 2025