1 - 20 of 78 Works in Underage Dean Winchester
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Dean is caught in the middle of a dispute between the Russian Mafia and a biker gang. How will he get out of here alive, especially since he's seen the boss' face and knows his name?
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Cas Novak doesn’t do feelings. He’s got a good job, a luxury loft, and a steady rotation of hookups that never stick around long enough to expect more. That’s exactly how he likes it—until he meets Dean Winchester.
Dean’s seventeen, still in high school, and way too smart for his own good. What was supposed to be a one-time thing becomes complicated when Dean refuses to be another nameless man in Cas’ bed. He’s not afraid to call Cas out, push his buttons, or dig into the emotional disaster area Cas has spent years pretending doesn’t exist.
Cas never thought he wanted this kind of connection, but when there’s a violent attack, he is faced with the reality of what Dean really means to him.
Queer as Folk rewritten and reimagined.
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My prompt fill for Dadfuckerfest's Fun In The Son event, AND prompt fill for the Daddycest Discord Server's Moodboard Madness event! Took out two birds with one stone on this one!
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Finally getting a few summer days of reprieve from hunting, John treats his boys to some alcohol before they play around in the motel pool. And as night creeps in, John's perverse desires for his eldest son only grow stronger. Dean has complicated emotions about it all, and Sam is completely oblivious to the dark depths of his brother and father's twisted relationship.
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HEED THE TAGS.
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@xPurdyGlambertx on Tumblr and Discord, hmu if you enjoy my works! -
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Sam longs for Castiel but Castiel yearns for Dean.
Sam is 12, Cass and Dean are 16
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Two teenage brothers sharing a bed. What could go wrong?
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HAPPY BIRTHDAY TO THE BESTIE Ladygizarme!!!!
some teenchester wincesty goodness for you today on your special day, love you hun🖤🖤🖤🖤
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My dark rewrite of the season 1 finale, "Devil's Trap."
"That's the funny thing about rot - you can cover it up, hide it, bury it, tell so many lies that you turn purple in the face. But all along, it festers beneath the surface, and will inevitably come to light in one form or another."
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Azazel possesses John, and Sam learns some ugly family truths.
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@xPurdyGlambertx on Tumblr and Discord, hmu if you enjoy my works! -
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Dean Winchester, an omega who has suffered years of abuse as a slave, believes he's beyond saving. Sold by his own father, he’s spent years in chains, both physically and emotionally. When Castiel Novak, an alpha, purchases him, Dean expects more of the same cruelty. Instead, Castiel offers him safety, freedom, and kindness.
As Dean struggles with his trauma, Castiel's patient and protective nature helps him heal. Over time, their bond deepens into love, and Dean learns to trust again. Together, they build a life of safety and love, leaving behind the pain of the past.
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Sam wondered what would have happened if he didn’t listen to his gut feelings that day. If he went over and licked and sucked his big brother’s dick. Would he be on his knees today, his brother standing over him… He knows he’s completely fucked in the head. He knows that what happened between them, what Dean started was just plain inappropriate and no one normal would ever want it to continue, to escalate. But Sam craved it, he thought about it every day, and he wanted his brother all to himself…he wondered if Dean remembered.
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Prequel to His Green Eyes.
Dean Winchester is eleven years old when he meets Castiel Novak, the man dating his father.
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Dean throws his bad across the room, falling on the hard and uncomfortable mattress with an annoyed grunt. In front of him, a long mirror reflects a figure of himself he doesn't recognize. On his arm, the burn and solidity he got used to coming from the Mark of Cain, gone.
This was gonna be a bitch of a situation to solve.
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Part 2 to Inhale. Sam and Dean are both underage. Dean has been smoking for a while, Sam just starts.
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- Part 2 of Unhealthy Coping by the Winchester Boys
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Dean is Sam and John's kid. He develops a weird obsession with his mom, Sam, that goes beyond platonic.
or Dean wants to fuck his mommy who is Sam.
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Only Real When I’m With You. by WhiskyBoys for Saltandburnboys
Fandoms: Supernatural (TV 2005)
21 Aug 2022
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At sixteen Dean was exceptionally pretty. Even for an omega. Fair hair, pale skin, big green eyes and wholesome freckles. And he was a virgin. The training officers, always smirking, said that was a good thing. Told him that was why his pathetic omega life was valuable enough to pay off all his father’s debts.
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Mary has searched high and, admittedly, very low, for a decent babysitter to watch her sweet, eight year old Dean. She doesn't understand why each potential sitter practically moves mountains to escape her beautiful home! When all hope has seemed to run away (with the babysitters), someone new moves into their small, shared cul de sac. Could this polite stranger possibly be the answer to all her problems?
or the one where Cas is most likely going to jail.
( on hiatus until further notice )): sorry )
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John decides to share Dean with some buddies from work
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- Part 6 of Sins of the Father
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Alpha Mary comes home from the grocery store to find her ten year old daughter, Deanna in her first heat.
WARNING: This is not a happy story. Deanna will be treated simply as a breeding bitch. Mentions of multiple future forced abortions.
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- Part 1 of Alpha Mary
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Dean Winchester recalls the many times he told Sam he loved him, and the one time Sam definitively said it back.
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When Dad’s gone and money is tight, Dean finds ways to make ends meet.
Wren's tags: supernatural, dean winchester, dubcon, prostitution, underage.
Wren's warnings: Prostitution, dubcon due to financial desperation, 15 year old Dean. This is an unrealistic, romanticized depiction of a teenager prostituting themselves for money, meaning that Dean is waaaaaaaay less scarred by it than a real person probably would be.
Archivist's warnings: I'm gonna slap a noncon tag on this, things are very bad with the consent from multiple directions.
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On Christmas of 1991 (shown in the flashbacks in season three, episode eight, A Very Supernatural Christmas), twelve-year-old Dean and eight-year-old Sam give each other hand jobs for the first time. Sam has his first ever orgasm.