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Senior year made Sam Winchester a boy kisser! by maskedbloodymisfit
Fandoms: Supernatural (TV 2005)
15 Aug 2025
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It's Sam's last year of high school. He knew in a 180 days he would cross the stage and be handed the diploma he worked his ass off for. But what he didn't know that within those 180 he would experience one of the weirdest school years of his life he ends up questioning his sexuality all because two boys caught his eye.
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This story follows 12 year old Samantha Winchester and her big brother 27 year old Dean Winchester.
The first chapter starts with a struggle of Sammy getting her first period and Dean needs to get her pads . But soon we will learn of the compromise and deal Dean gives Sam .
If you can find a balance between normal kid life and training to be a hunter then maybe she can be a TEENAGE HUNTER with her protective OLDER BROTHER there to help and guide her.
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After an unfortunate run in with the mafia John's in debt to Dean is forced to work with the apposing mafia that's been trying to take over Hell's Torturers territory for years. The fight becomes personal when Castiel catches feelings on Dean who is always in danger due to his idiotic fathers debts.
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Supernatural mafia AU bc freewill is freewill -
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Derek was doing well for himself and his pack of misfits, until a certain family comes to town.
Someone in particular is out to get this family, and the pack fall for some of the lies and rumours, so they partake in messing with certain individuals, whilst planning something way more serious to harm this family.
Does the realise their mistakes, or are they leading themselves down a warpath?
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Ever since Mr. Gabriel Novak had started teaching at Sam's school, Sam had a crush on him. Several years later, when Sam has become a teacher himself and returns to his former school, he still can't help fantasizing about that gorgeous biology teacher.
Litte disclaimer because I've been asked about it: when Sam dreams and imagines himself being a teenager again, he's ALWAYS seeing/imagining himself as being 18 again because that's the age when he had seen Mr. Novak for the last time. I won't stand for anybody accusing me or assuming that I'm promoting pedophilia.
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Tags will be added with each chapter that is posted. -
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"Here I am thinking I finally got away from my ex from high school but now his toxic ass is standing in front of me in college. I am Castiel Novak and I officially want to throw myself off a bridge."
Castiel thought he was finally done with high school drama his first year of college but he was wrong. Is he going to have to suffer these first few semesters or will this new coffee boy come to his aid?
“Dean Winchester. The name is Dean Winchester.” -
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Dean was what everyone in the school would classify as your ‘typical nerd’. Straight A’s in everything, homework before dinner, no social life besides online gaming, virgin at the age of seventeen, and a senior no less type of nerd.
Castiel was dating the hottest girl in school, who also happened to be cheer-leading captain. He has a ride to his favorite university because of his smarts. Why can't anyone get past the jock exterior and look past it into who he really is? Appearances can be deceiving. He might as well play into it right?
Inspired by the movie "She's All That"
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Got this from a Pinterest Post
Cas as the quiet, unassuming preacher's son who attends mass every sunday and dresses like a middle-aged bible salesman.
Dean as the juvenile delinquent in the too-big leather jacket who becomes interested in him and makes it his mission to seduce and despoil him.
Who is then shocked to find himself pinned against the wall in the confessional booth after everyone else has left, gettin ghis brains fucked out as it turns out Cas is not as virginal as he seems.
Not that he minds. especially not when Cas wraps a hand around his neck and another around his hips, and starts driving into him like a man possessed.
Dean's never come untouched before but he does now, whimpering and pushing desperately back onto Cas' cock. -
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Sam volunteers to help teach six-year-olds how to play soccer, and he learns the real reason why Dean is suddenly all too willing to drive him to practices-- his brother has a crush on Castiel Novak, one of the guardians of the kids on the team.
Title from Taylor Swift's "How You Get the Girl"
Series
- Part 18 of alfie's destiel oneshots
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There once was a man so evil everyone feared him and no one dared cross him. He owned peach orchards where he threatened, coerced, and forced people in town to buy his fruit, and even went on to supply them for the entire state. He was a miserable, horrible person that, upon his death, became a local urban legend, and a test of bravery for the graduating seniors. The dare was to go into the orchard and come back with a piece of fruit. In all the years since the old man had died, not a single person had made it out with a peach.
This time it was Sam who was dared to go into the orchard. He thinks this time he'll actually get out with a peach, chalking the ghost up to vivid imaginations, though he didn't doubt the possibility that one existed. His brother and brother's boyfriend came to be there for him, in case he needed help getting out but he had a plan: Get in, grab the first piece of fruit he saw, and get the hell out. He learns the hard way that some urban legends are real, and they can be quite dangerous.
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- Part 19 of 31 Days of Halloween 2022
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Sam Winchester wanted a normal life, starting with a normal senior year. Little did he know Smallville High wasn't going to be the place for that.
Series
- Part 1 of Svnatural AU
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At Sam’s insistence, Dean goes to the local hospital to get his COVID-19 vaccine. His nurse, Castiel, is new to town, and Dean enjoys chatting with him so much that he sort of…inadvertently asks him out during the 15-minute post-shot observation period.
Though he reminds Dean that the pandemic makes going out pretty difficult, Castiel is deeply flattered. Ever since moving to North Dakota five months ago so that his brother could shoot a documentary called Halcyon Days, Castiel’s been counting down the weeks until they could leave. Maybe Dean is a reason to stay—or at least a way for him to pass the time.
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“You’re damn lucky I was uptown,” Dean says as Sam ducks into the passenger seat. Sam keeps an extra hoodie in the car, and he tugs it over what he’s wearing, crossing his arms over his chest as if to hide his body. Passing street lamps catch smudged color around his lips and eyes.
It’s when they’re driving across the Queensboro Bridge that Sam says, “You’re not gonna tell Dad, right?”
Series
- Part 1 of I Will Die in This Beautiful Place
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Dean only hears something mumbled in a deep voice that sort of sounds like, “More shots.”
The bartender pours six shots, and Castiel drinks two, pauses to look at Dean with bright blue eyes under a mess of black hair, and rolls his shoulders. He has his trench coat collar flipped up, which hides most of the man’s face. He drinks a third shot, collects the other three in one hand, and reaches out to touch Dean’s shoulder. He leans in and kisses Dean’s cheek, then turns away and shuffles back to his booth, shots in hand.
Dean wipes his face and looks back on the bar. “Interesting guy." -
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Sam is in his first year of college and Dean decides to visit him when he finishes work early one day, in the hopes of some brotherly bonding and maybe some dinner. When he arrives at Sam’s dorm its to find him leaving it for a late afternoon class. Deciding to tag along anyway to see what a college class is like; Dean expects to be thoroughly bored until the TA walks in and his attention is on him the entire lesson.
Series
- Part 1 of A Love Story of Dean and Castiel
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Dean and Bobby miss Sam's graduation for a hunt that goes awry; he spends the next few day's at Rhonda Hurley's house, feeling almost normal.
Series
- Part 3 of Rhondanatural
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ficlet - sam/gangbang, dean walks in by wrenseroticlibrary_archivist
Fandoms: Supernatural
16 Jul 2021
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This fic is three lines long.
Wren's tags: 3 liner, supernatural, gangbang, sam winchester, dean winchester, writing.
Wren's warnings: Highschool Sam, 18 years old. There’s drinking, but not beyond the point of consent.
Archivist's warnings: None.
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Sam is walking home from high school when he falls in with the wrong crowd. The wrong crowd in this case is about two feet tall, fresh from the sulfurous pits of Hell, and incredibly annoying. And they’ve got drugs. Drugs from Hell. ...Hell drugs.
Wren's tags: Supernatural, Sam Winchester, monster sex, gangbang, noncon, come dripping everywhere, I have no idea how else to tag this, sub!sam, sex hex, romnoncon, mindbreak, writing.
Wren's warnings: Monster sex, gangbang, heavily romanticized noncon, drugging. Contains faint traces of wincest. Sam is not a minor.
Archivist's warnings: None.
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"Dean turns seventeen today. We went shooting. Then I sent him out on his first hunt. I've let him take the lead before, but I've always been there to back him up. This time he's on his own. Partly it's a test, and partly I wanted some time with Sammy. Should be no problem for Dean. Ghosts of two nuns haunting St. Stephen's Indian Mission in Riverton, Wyoming. Simple salt-and-burn mission. Nuns in love with each other, then discovered. Killed themselves. We scoped the situation out, figured that something must be left behind that's now a focus for the haunting. Bible, rosary beads, some small article that's hidden somewhere in their room. I figured Dean would take care of it no problem." - John Winchester's Journal.
What if Dean developed a crush on a guy, and subtly implied that he was going out with a guy? This is my interpretation of what happened.
Series
- Part 9 of Febuwhump 2021
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Castiel has always been the obedient son. Losing his parents, and losing himself has made it difficult to find his way out of the cage he's locked himself in. Constantly striving to please, his life has always been the same routine- pray, learn, sleep, repeat. Until one day his life begins to slowly change and he can't understand what's different. Until he can.