1 - 20 of 49 Works in Cheerleader Dean Winchester
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Dean Winchester was lucky enough to get a free ride to college due to his cheerleading scholarship. However, he had to postpone his college experience until he turned 20, as he was too busy working in order to attend college. After two years of minimum wage and long nights, he has saved up enough for Sam to move out and go live with a close family friend, Bobby Singer. Dean fits right in on his first day and quickly becomes the talk of the school because of his charming personality and stunning looks.
Castiel Novak, an aspiring artist, is also one of the students who gets mesmerized by Dean Winchester. Unfortunately he's too shy to talk to the man and tries to convince himself he's content with staring at him from a safe distance. Until he isn't.
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Dean liked cheer. He was good at cheer. He loved his teammates, the sports team seemed to like him fine too, and there was –
Well, there was their mascot. -
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Dean Winchester is not your average cheerleader.
He doesn’t wear the sexy outfits. He doesn’t do the flips or the dances. He is one of those aggressive cheerleaders.
But damn, can you hear him over everyone else.
He gets the crowd riled up. He gets them to cheer and scream.
That’s his little brother on the field. Dean will make sure that EVERYBODY knows who Sam Winchester is.Castiel moves to the small town of Lawrence, Kansas and meets the asshole Dean Winchester. Nobody has gotten on his nerves more.
It doesn’t help that his brother Gabriel decides to sign him up for the cheer squad.
He doesn’t get it. He doesn’t understand why someone would scream so loud for a goddamn football game.Dean’s pissed off about this. He doesn’t like the way Castiel acts. So what does he do? He puts on his signature cocky smirk and cheers on Cas.
With EVERYTHING. -
Senior Year (destiel) by Aurora_del_artico
Fandoms: Supernatural (TV 2005), Senior Year (2022)
30 Mar 2025
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Basada en la película del mismo nombre que salió en 2022.
(...)
Dean es un omega, capitán de los animadores, sale con Michael Shurley, el alfa más popular del instituto y su único sueño es conseguir su vida perfecta. Y el primer paso es ser el rey del baile. Pero un día antes Dean sufre un accidente quedando en coma por 19 años. Al despertar deberá encontrar una forma de superar lo que paso.
¿Qué mejor forma de hacerlo que volviendo al instituto? -
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Taking care of people was always Dean's job, and he took it very seriously. When he left for college, he wanted to take care of himself too.
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- Part 2 of Mary Lives AU
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Dean and Sam Winchester move to Sioux Falls for good. The only down side is Dean’s rocky relationship with the school punk Castiel Novak. After a fight and some first aid, just maybe these two can stitch together a relationship they both want
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Original prompt: Russian, possessive, jealous, socially awkward, alpha Castiel who falls super hard for freaking genius, popular, constantly hit on omega Dean in a high school setting
Or,
The one where Lawrence High School gets a new student and Dean’s curiosity is immediately piqued.
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- Part 1 of When Alpha met Omega
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High School AU where head cheerleader Dean welcomes his quarterback boyfriend Benny back home.
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Dean wears his special Cheer uniform to meet his boyfriends after class.
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In which Sam is a junior and the football star, and Dean is a senior and one of the cheerleaders. And after every game, once the others have left and they have the locker room to themselves, they fuck so hard that it’s a better workout that either of them got during the game.
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This is less of a Christmas fic, and more of an excuse for Cas to fuck Dean in a cheer leading skirt set relatively close to Christmas. If you like Dean in panties and needy bottom!Dean, this is the fic for you.
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When the hottest girl in school gets together with one of the nerds of course everyone thinks it's about homework and all that... but it isn't.
(This is basically where I dump all the fluff I can come up with so get ready for pointless happiness)
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- Part 24 of Fluff
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Ever heard the saying, bad things happen in threes? Well, Dean's unfortunately learning that the hard way. Only problem is Dean is just too tired and emotional to deal with this all. Dean thinks he's pretty strong but... this actually might break him.
Relationship level: Hopeless
(AN//: Make sure you read the first TWELVE, or you will be so terribly lost. ))
Series
- Part 13 of I'm NOT your boyfriend!
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Castiel has a lot of unresolved issues with his father, and Castiel for one, doesn't think he deserves to be forgiven. This isn't that kind of story, where everything's just...fixed. Some things can't just get better, some people can't just be forgiven. Some people have to live with their guilt. Anyways, enough about Chuck. Dean exists and he's super adorable.
Relationship level: It's negative?
(AN//: Make sure you read the FIRST eleven, or you will be so terribly lost. ))
Series
- Part 12 of I'm NOT your boyfriend!
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After a lovely and surprising kidnapping by his boyfriend to the worse place imaginable aka his family vacation, Dean is learning there is another side to Castiel he's not sure he likes, with issues he's not sure he can handle. Dean's starting to wonder where the liquor cabinet is...
Relationship level: It's complicated.
(AN//: Make sure you read the FIRST ten, or you will be so terribly lost.))
Series
- Part 11 of I'm NOT your boyfriend!
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Castiel may have things going his way with his fiancé Dean, but at home there's another story. It's not that he doesn't have a family or they are too irrelevant to the plot. Castiel's...just never gotten along with them. Like oil and water, they are able to touch but never combine. When a opportunity arrives for Castiel to come clean about things, he finds out the meaning of kidnapping.
Relationship level: a ROCKY two.
(AN//: Make sure you read the FIRST nine, or you will be so terribly lost.))
Series
- Part 10 of I'm NOT your boyfriend!
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My favorite flavor of bubble gum tastes like self-loathing by Nachsie
Fandoms: Supernatural
13 Feb 2016
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Dean's been having a hard time lately...Don't get him wrong, he's been the happiest he's ever been but..He's been finding himself lonely. Castiel's been a lot more busy lately, which is fine. Dean's pretty sure it's his whole silent angst over something unrelated to Castiel that's causing him to be down in the dumps. Just...seeing Castiel less isn't helping. When Castiel surprises him on their day off school, Dean's days about to get a whole lot better.
Relationship level: a SOLID two.
(AN//: Make sure you read the FIRST eight, or you will be so terribly lost.))
Series
- Part 9 of I'm NOT your boyfriend!
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First day of school for senior year, and things are looking up. He ate a filling breakfast this morning, didn't struggle to get up this morning, and Castiel had matching socks this morning...A Average perfect day. Balthazar keeps saying things are going to change now that he's officially on the football team. Castiel on the other hand doesn't think so...
Relationship level: One point five.
(AN//: Make sure you read the FIRST SEVEN, or you will be so terribly lost.))
Series
- Part 8 of I'm NOT your boyfriend!
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Full pack of smokes and to quote Britney 'oops I did it again' by Nachsie
Fandoms: Supernatural
09 Feb 2016
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With the summer almost over, the cheerleaders all end up going upstate to compete for the last month of summer. With how things are going with Castiel and Dean, Dean is finding it hard to leave. Also Castiel's really digging this summer camp after all.
Relationship level: One.
(AN//: Make sure you read the FIRST SIX, or you will be so terribly lost.))
Series
- Part 7 of I'm NOT your boyfriend!
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Drowning in love (or in revenge...no one's keeping score) by Nachsie
Fandoms: Supernatural
08 Feb 2016
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Castiel's got a lot of growing up to do if he wants to get his omega back, however Balthazar's rather homicidal ways may not be the best way of doing that.
(AN//: Make sure you read the FIRST FIVE, or you will be so terribly lost.))
Series
- Part 6 of I'm NOT your boyfriend!