1 - 20 of 248 Works in High School Student Dean Winchester

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  1. Tags
    Summary

    Dean is aware of the expectation that a boyfriend should give his girlfriend at least one sweatshirt of his for her to wear. He is also aware of just how upset said girlfriend may become when you ask for your sweatshirt back. But he doesn't care. He has one sweatshirt, and he'll be damned if he's going to leave it behind when his dad catches wind of a new hunt. So he stops caring about the expectation. He stops giving it away.

    But now he's sitting on Castiel's bed, and he's supposed to be ready to leave in an hour, and Cas looks damn good in the sweatshirt.

    Language:
    English
    Words:
    14,248
    Chapters:
    6/?
    Comments:
    23
    Kudos:
    166
    Bookmarks:
    15
    Hits:
    4653
  2. Tags
    Summary

    The high school dance was useless in Castiel's opinion; there was nothing to do, people were incredibly annoying, and he would be alone. But, having Charlie Bradbury as his best friend, he had no choice but to go; after all, there was a tiny chance he would get tacos after the party.

    Castiel did not get tacos but he got something a lot better.

    Series
    Language:
    English
    Words:
    2,594
    Chapters:
    1/1
    Collections:
    1
    Comments:
    3
    Kudos:
    34
    Bookmarks:
    4
    Hits:
    529
  3. Tags
    Summary

    Cas needs to make more hard decisions, Dean needs to find his courage, and Sam needs to be a little less smart for everybody's sake.

    Series
    Language:
    English
    Words:
    5,610
    Chapters:
    1/1
    Comments:
    5
    Kudos:
    20
    Hits:
    294
  4. Tags
    Summary

    "Row, row, row your boat gently down the stream, merrily, merrily, merrily I can make you scream."
    Castiel sang as he smirked at his victim that was called Dean Winchester.

    updated summary
    Follow along with Dean being the boy who's life changes thanks to Castiel.
    Reader insert, only in newer chapters.

    Language:
    English
    Words:
    24,984
    Chapters:
    25/25
    Comments:
    33
    Kudos:
    358
    Bookmarks:
    44
    Hits:
    17729
  5. Tags
    Summary

    Dean Winchester is just starting his Jr year of High School and is somehow already overburdened with sky-high expectations and responsibilities. Will he be able to leave the drama in the Drama Department, buckle down on his studies, and focus on his future? Or will Dean give in to his heart and allow himself to become romantically entangled with new kid Castiel, despite mounting concerns over Cas's frequent substance abuse and mental health...?

    Language:
    English
    Words:
    19,308
    Chapters:
    16/?
    Comments:
    3
    Kudos:
    29
    Bookmarks:
    3
    Hits:
    597
  6. Tags
    Summary

    Castiel married the love of his life, Dean Winchester, on a Monday.

    Language:
    English
    Words:
    460
    Chapters:
    1/1
    Comments:
    8
    Kudos:
    31
    Bookmarks:
    2
    Hits:
    493
  7. Tags
    Summary

    Dean smiles, privately, to himself, before looking down at his canvas.
    A rough sketch of a pair of eyes stare back at him, colourless and grey. Dean sneaks another glance, studying from afar, how Cas's eyebrows raise as he speaks, his eyes narrowing and the smile on his face spreading wider.

    (artist! student! Dean secretly draws and paints his crush Castiel's eyes as they sneak glances at each other from across the garden, leading to love confessions. Hehe. ;D)

    Series
    Language:
    English
    Words:
    2,712
    Chapters:
    1/1
    Comments:
    9
    Kudos:
    80
    Bookmarks:
    15
    Hits:
    996
  8. Tags
    Summary

    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"

    Language:
    English
    Words:
    30,212
    Chapters:
    18/22
    Collections:
    1
    Comments:
    137
    Kudos:
    223
    Bookmarks:
    35
    Hits:
    5734
  9. Tags
    Summary

    “Well,” Cas starts, thoughtfully, “I’m glad I can help you like this, even if just for a while.”

    Dean ducks his head to hide the blossoming grin appearing on his face. He picks his blue coloured pencil back up and continues to fill in the lines.

    //

    Or the one in which School Social Worker Castiel gets way more than he bargained for when he can't help but get attached to his new charge: Dean Winchester.

    Language:
    English
    Words:
    1,704
    Chapters:
    2/?
    Comments:
    2
    Kudos:
    34
    Bookmarks:
    6
    Hits:
    439
  10. Tags
    Summary

    there is no heterosexuality in this fic
    don't worry
    i originally made this a reader x crush fic
    then changed it to queliot
    then destiel
    i'm a trans guy but this is not (!!) my life! or how i'm telling you trans boys are!! it's just a fic!! that is hopefully better since i know what having a vagina feels like!! but not a penis!!
    also don't kiss people right after eating them out it's unsanitary and probably spreads stds or smthg i don't fucking know
    no beta we die like men

    Language:
    English
    Words:
    4,708
    Chapters:
    1/1
    Comments:
    2
    Kudos:
    12
    Bookmarks:
    2
    Hits:
    441
  11. Tags
    Summary

    It’s the night of the homecoming football game. The band has been practicing this show for months. The band room is a mess of uniforms, people, and instruments. Everyone is getting ready... except for Castielle. She’s sitting on a table watching Deanna rage around the room trying to find valve oil and trying very hard not to laugh.

    Series
    Language:
    English
    Words:
    3,532
    Chapters:
    1/1
    Comments:
    3
    Kudos:
    6
    Hits:
    160
  12. Tags
    Summary

    After John Winchester's precious car is vandalized with homophobic slurs, Dean and Castiel exact their revenge, and re-evaluate their friendship.

    Language:
    English
    Words:
    6,070
    Chapters:
    1/1
    Kudos:
    66
    Bookmarks:
    5
    Hits:
    757
  13. Tags
    Summary

    Continuation of Parenting 101. Drabbles about the boys growing up. Must read Parenting 101 first. Includes de-aged Michael, Lucifer, Raphael, Dean, and Cas. Fluff mostly with angst here and there. I hope you like it.

    This work has several squares from the three bingos I have in the process. (Sam Winchester, DeanandCas, and Castiel) I will mention each one in the beginning notes.

    Series
    Language:
    English
    Words:
    9,642
    Chapters:
    11/11
    Comments:
    8
    Kudos:
    58
    Bookmarks:
    8
  14. Tags
    Summary

    Alright, so you know how in movies the friendzoned BFF always gets the girl in the end? Well what if the girl is a dude and you’re also a dude? Do the same rules apply? Or will this clusterfuck end with me losing my best friend?

    Series
    Language:
    English
    Words:
    15,579
    Chapters:
    11/11
    Comments:
    54
    Kudos:
    129
    Bookmarks:
    23
    Hits:
    2128
  15. Tags
    Summary

    Cas and little brother Gabriel live with their abusive mother but with their father chuck every other weekend. They become friends with Dean and Sam while showing them around the school.

    Language:
    English
    Words:
    38,080
    Chapters:
    21/?
    Comments:
    23
    Kudos:
    88
    Bookmarks:
    5
    Hits:
    3218
  16. Tags
    Summary

    Dean is about to meet his girlfriend Claire’s parents for the first time.

    Or,

    The one where Dean’s girlfriend’s dad is Castiel fucking Novak.

    Series
    Language:
    English
    Words:
    2,996
    Chapters:
    1/1
    Comments:
    32
    Kudos:
    188
    Bookmarks:
    10
    Hits:
    2381
  17. Tags
    Summary

    Dean needs a suppository. Sam has to help him.

    Series
    Language:
    English
    Words:
    1,579
    Chapters:
    1/1
    Comments:
    3
    Kudos:
    179
    Bookmarks:
    4
    Hits:
    2261
  18. Tags
    Summary

    Dean has just entered his senior year and is Captain of the Varsity Football team. Him and the guys hear about two new transfer's. They're two of Michael's cousins. Castiel and Gabriel Novak. Dean isn't sure why he's drawn to the blue eyed brother but decides not to over think it too much and make friends with the intriguing guy.

    Cas and his siblings have just moved to Freewill, Kansas. At first Cas thinks his senior year will be just lile every other. Almost no friends and boring outside of sports. That is until he meets Dean Winchester. Hot football player who is just Castiel's type, however the guys becomes quick friends and Cas doesn't want to lose that.

    Complete (Part 1 of a series but can be read on its own)

    -------
    Get ready for some Dean-ial, fluff, angst, athletic boys, sexy cars, A+ parenting, some slow-burn, and smut.

    Some chapters might have drawings accompanying them.

    Series
    Language:
    English
    Words:
    350,063
    Chapters:
    55/55
    Comments:
    956
    Kudos:
    914
    Bookmarks:
    122
    Hits:
    17537
  19. Tags
    Summary

    When John dumps the boys in a small Oregon town for the summer, Dean is happy to have a moment to breathe and time to spend with his little brothers, Sam and Adam. At first, Dean doesn't know what to make of it when Sam strikes up a friendship with Cas, the odd neighbor boy who is always building something in his backyard. But as money starts to get tight and Dean has to decide what's worth fighting for, Cas and his family help him in ways he never expected.

    Language:
    English
    Words:
    67,875
    Chapters:
    19/19
    Collections:
    1
    Comments:
    266
    Kudos:
    672
    Bookmarks:
    155
    Hits:
    9251
  20. Tags
    Summary

    Castiel Novak is a new student from the big city, whose past might not be as innocent as his blue eyes let on.

    Dean Winchester is a rich playboy who's given up breaking the ancient prophecy he was cursed with years ago. When they meet, there's an instant connection between them, but everyone warns Cas to stay away.

    Are they right? Is it too late to save Dean? Just a preview, so please comment and let me know if it's interesting!

    Language:
    English
    Words:
    555
    Chapters:
    1/?
    Comments:
    6
    Kudos:
    17
    Bookmarks:
    1
    Hits:
    349

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