1 - 20 of 287 Works in Jock Dean Winchester
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At lunchtime Dean plays Truth or Dare with his jock friends. He stupidity picks dare and is dared to kiss the resident bad boy punk.
Cas is that punk. He comes to school their senior year to hopefully finish. Unfortunately his piercing, tattoos, hair color, wardrobe get in the way. And especially his attitude. He is not there to make friends. He is feared by most, even the bullies.
Series
- Part 10 of Random Thoughts and Bad Ideas
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The Diary of a Popular Jock by AngelOfImpala221
Fandoms: Supernatural (TV 2005), Supernatural
28 May 2025
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Dean-centric Diary that goes through his thoughts and ends up with him being happy.
2025 Edir: ABANDONED!!
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As a kid, Dean’s dreams were pretty straightforward: food, a roof over his head, and maybe – if he really let himself dream big – a family that wouldn’t kick him out the second he became more trouble than he was worth. College? Not on his radar. Suddenly he’s here, though – on a football scholarship and faced with the possibility that this time he might get to stay.
For someone more well-adjusted it would be a dream come true. For Dean it’s a nightmare of desperately keeping up appearances while he’s drowning in other people’s expectations.
At least until a game of Truth or Dare sends him face-first into the arms of Castiel Novak. Senior. Resident (ex-)drug dealer. Obnoxious literature major. Heavily tattooed and everything Dean is trying to leave behind.
Dean needs a favor and Castiel is all too willing to deliver. Unfortunately the offer comes with strings attached that go well beyond the fake relationship that Castiel asks for in return.
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Castiel and Dean were once friends, now rivals. After a game-changing moment, Cas can’t help but think, What the fuck is happening? Neither of them knows, but something’s about to change.
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It was supposed to be a one time thing, Castiel was content to know that he got to see his crush's dick and then he'd never see Dean again, but that first time led to so much more.
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Classic Cars and Post-Impressionist Stars by noirangetrois for Angeleyz4ever
Fandoms: Supernatural (TV 2005)
20 Dec 2024
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Castiel can't believe he's been paired with the school's number one delinquent for the midterm project of his favorite class, art. But Dean Winchester turns out to be more than Castiel expected — much more, in fact. He couldn't be more happy to have been wrong.
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While The Wolf's Not Home by notyourtipicalauthor
Fandoms: Teen Wolf (TV), Supernatural (TV 2005)
08 Sep 2024
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Stiles Stilinski remembers Coach Winchester's offer after his boyfriend Derek rejects his advances because Derek is still scared
Series
- Part 14 of Cheating Stiles Stilinski
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Dean Winchester, the star Quarterback of the Kansas University football team. He's real popular around here, If you haven't envied or crushed on him for his stunning good looks or incredible skill on the field, you haven't met him. You could describe him in many ways: frisky, flirtatious, ..failing one of his core classes. He's in danger of indefinite suspension if he doesn't pick up his grades, and fast. He's desperate.
That's where Castiel Novak comes in, agreeing to tutor Dean for a small price. Nothing to even really consider, it'd work out perfectly for the both of them! Cass has always been a little bit of a sadist, however, and he isn't one to drop a grudge.
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the feelings overrated (but it's true) by mostbelovedrogers
Fandoms: Supernatural (TV 2005)
29 Oct 2023
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Castiel has had a crush on Anael since junior year. He creates a plan the summer before senior year to finally get closer to her, but when new student Dean Winchester moves to town for their last year of high school, Cas doesn't seem to like the way Anael is always with him. He's never been more jealous of anyone in his life.
Dean, on the other hand, thinks Castiel is one of God's greatest creations.
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Dean Makes It His Mission To Befriend The School OutCast Benny Lafitte
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It's senior year and Castiel Novak isn't expecting anything exceptional to happen. He has his friends, his debate team, his family to drive him crazy, and only a vague idea on what the hell he's going to do after high school. When his brother's childhood friend moves back into town, the most Castiel can hope for is expanding his social circle by a person or two.
Dean Winchester didn't think he'd be spending his first year of "adulthood" still in high school and suddenly under his father's thumb again. He's trying to make the best of it, giving his all on the hockey team and looking out for his little brothers while fostering his newfound friendship with his classmate. Only thing is, the full on gay crisis he's having is throwing a wrench in his year.
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Cas has been half in love with the lovable jock Dean Winchester for a while, and Dean fell head over heels for Castiel the moment his sister Anna had introduced them. Cas is a hot pierced and tatted punk who gives no fucks and protests with the loudest of them. Cas is also "out" and Dean is decidedly not... so all that want Dean has.... it goes into the ear of one Charlie Bradbury who tried to help push the two idiots together. Can Pride do what one computer hacker could not?
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Dean has never really hung out with anyone outside of his group. This wasn't something anyone really noticed because he was a pretty friendly person, just friendly enough that no one noticed how little time he spent with anyone. At least he thought no one noticed.
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The one where Dean falls in love with Cas after they meet while hiding from a crowded party
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Music Led Me to You by SoulOfAnArtist, VampireRose
Fandoms: Supernatural (TV 2005), Supernatural
25 Jul 2022
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Castiel and Gabriel Novak moved to Lawrence Kansas to have a fresh start. Having past traumas, Gabriel with relationships and Castiel with friendships, can they adapt to this new place? Will Gabriel ever feel safe again and how will Castiel be comfortable around other people? And what's with that one jock who keeps staring at Castiel?
(Mature because of graphic details of abuse in chapter 23)
P.S-> Story has been put on pause for the past year (or two?) due to *brain fart*. Any critizism, ideas, or anything would be helpful. I really want to finish this story for you guys, but I'm stuck...
Series
- Part 5 of Roleplay Inspired
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After Dean wins a football game, Sam and Dean find a place to celebrate.
Sam is 14 and Dean is 18.
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Castiel Novak is your stereotypical high school nerd and coffee shop employee always overlooked. Then one day, the ever-elusive jock Dean Winchester - aka Cas' bully - follows him to the coffee shop. From there, a strange relationship begins to bloom between the pair, but it is interrupted by a beautiful disaster. What will happen next? All the gay (of course).
To keep it short: All the tropes. All the cliches. All the gays.
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The strange development of falling for what you're against.
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Castiel Novak and Sam Winchester are great friends but Sam's older brother gets under Castiel's skin.
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The Silence Between by charmin365, Yvhvhvtke
Fandoms: Supernatural, Supernatural (TV 2005)
20 Jan 2022
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Due to a family tragedy, Castiel becomes the new kid in town for his senior year. Not only is he the new kid, he’s a nerd, and he’s mute. Nobody pays any attention to him, unless it’s to make fun of him.
Dean starts his senior year a few weeks late thanks to an injury he sustained over the summer. He’s popular, the captain of the baseball team, and in danger of failing. He turns to the new kid for tutoring.
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Dean Winchester is Captain of the football team and Castiel is the new weird kid. Dean and his friends are coming for Cas to make his life a living hell. Everyone of them seem to succeed except for Dean. He never gets the reaction he expects from Castiel, only a small smirk here and there until one day he's had enough and corners Castiel in the shower. Dean didn't realize he was dealing with a masochist until it was too late.
Violent and dirty dirty SMUT. Lot's of Smutty smut smut. Now that I have your attention... enjoy ;)
Series
- Part 1 of Locker Room Secrets
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When student Dean Winchester, Sioux Falls High Schools star football player, gets paired up with the new kid Castiel Novak, friends will be made, people will get hurt, and secrets will be spilled. Will Dean and Castiel get through it together or will it be too much for them to handle?