1 - 20 of 46 Works in Dean Winchester Questioning Own Sexual Orientation

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  1. Tags
    Summary

    Shortly after Claire's brief stint as a werewolf, a solo witch hunt in Stockton, South Dakota goes awry, and she finds herself face to face with Dean...in 2002. They work together to get her back to 2017, and hijinks ensue.

    Language:
    English
    Words:
    13,465
    Chapters:
    6/6
    Comments:
    18
    Kudos:
    77
    Bookmarks:
    19
    Hits:
    532
  2. Tags
    Summary

    It all comes down to feelings and how we express them. And oh, Dean Winchester would take any chance he was given to redeem himself from the time he most wished he’d spoken his mind.

    Language:
    English
    Words:
    2,171
    Chapters:
    1/1
    Comments:
    4
    Kudos:
    49
    Bookmarks:
    6
    Hits:
    337
  3. Tags
    Summary

    Castiel runs away from the religious cult in which he was raised. He ends up in a small town in central Arkansas, broke, alone, and hurting. When he meets Dean, however, things seem to be looking up.

    Dean wishes he could run away from his current life...well, mostly, he wants to run away from his father. He hires the new-to-town Jimmy to work in his family's diner. The longer they spend time together, the more profound their bond grows.

    Can the men overcome their pasts and presents with help from each other?

    Language:
    English
    Words:
    79,389
    Chapters:
    25/25
    Comments:
    136
    Kudos:
    115
    Bookmarks:
    29
    Hits:
    2,430
  4. Tags
    Summary

    Dean is supposed to get married in two months. Too bad he's in love with the priest...

    Language:
    English
    Words:
    46,664
    Chapters:
    15/15
    Comments:
    79
    Kudos:
    143
    Bookmarks:
    28
    Hits:
    2,304
  5. Tags
    Summary

    There's something about the new kid, Cas, that made Dean feel things he hadn't felt before.

    That's totally normal... right?

    Series
    Language:
    English
    Words:
    2,261
    Chapters:
    1/1
    Comments:
    14
    Kudos:
    119
    Bookmarks:
    13
    Hits:
    924
  6. Tags
    Summary

    My take on season 5, episode 4 "The End" where 2009 Dean has a very different encounter with 2014 stoner Cas!

    @xPurdyGlambertx on Tumblr and Discord, hmu if you enjoy my works!

    Language:
    English
    Words:
    4,074
    Chapters:
    1/1
    Comments:
    9
    Kudos:
    362
    Bookmarks:
    31
    Hits:
    3,545
  7. Tags
    Summary

    Taking on this Assignment is a road Jimmy Novak has been down before. The fake name he used for most of his life Castiel had been surviving. Drownding slowly for years. Now when Dean Winchester approached him on shutting down the cult once and for all he takes it.

    Dean has no idea that Jimmy Novak, a fellow Alpha, is Castiel, the cult leader's son, or that he's an Omega. These next five months have him questioning if he's falling for an Alpha, which he's not, or why Jimmy sometimes acts strange.

    Language:
    English
    Words:
    5,438
    Chapters:
    2/?
    Comments:
    9
    Kudos:
    61
    Bookmarks:
    7
    Hits:
    677
  8. Tags
    Summary

    Waking up to the smell of something burning usually isn't a good thing, but waking up to Dean standing in your doorway definitely makes up for it. Feelings are hard and Sam forces you and Dean to confront them.

    Language:
    English
    Words:
    1,323
    Chapters:
    1/1
    Collections:
    1
    Comments:
    1
    Kudos:
    52
    Bookmarks:
    2
    Hits:
    692
  9. Tags
    Summary

    Cas and Dean are roommates. When they see a saucy scene on TV, Dean shocks Cas in to offering something he never expected.

    HUGE thanks to Foxymoley for helping find the closest origin of the pic of Misha I used as inspiration for this fic. Please enjoy this 🔥 edit courtesy of MishaInMakeup

    This is pretty much the exact face he makes at Dean from his side of the couch when he says that lol.

    Language:
    English
    Words:
    3,963
    Chapters:
    1/1
    Comments:
    12
    Kudos:
    181
    Bookmarks:
    16
    Hits:
    1,497
  10. Tags
    Summary

    -

    Since Dean is not the greatest fan of traveling for work he just wants to check into his hotel room for the night after a long day of driving and enjoy some peace and quiet.

    What he finds, however, is a naked man in his bed.

    It only spirals out of control from there.

    -

    Language:
    English
    Words:
    13,611
    Chapters:
    4/4
    Comments:
    148
    Kudos:
    784
    Bookmarks:
    124
    Hits:
    6,269
  11. Tags
    Summary

    Nassau, 1717. Captain Dean Winchester of the Impala is a born and raised pirate, committed to disrupting commerce and civility on a global scale. After a battle at sea with the Royal Navy, Dean discovers a stowaway on his ship: Castiel Novak, an officer from Carolina with a secret. As their relationship grows, so does England’s determination to end piracy in the New World. This is the story of how men can become legends and how love can ignite a revolution.

    Language:
    English
    Words:
    246,531
    Chapters:
    16/16
    Collections:
    3
    Comments:
    928
    Kudos:
    1,003
    Bookmarks:
    440
    Hits:
    35,144
  12. Tags
    Summary

    Castiel has been watching Dean's dreams in fear that something is wrong. What's wrong with Dean? Gay panic.
    ------
    Aka: Cas finds himself wanting more after seeing something he shouldn't have, and Dean finds himself accidentally listening from the other side of the door.

    Language:
    English
    Words:
    1,275
    Chapters:
    1/1
    Comments:
    13
    Kudos:
    145
    Bookmarks:
    10
    Hits:
    2,288
  13. Tags
    Summary

    Dean is straight. As straight as they come. Sure, he has guy crushes, who doesn't (Dr. Sexy and Harrison Ford amiright?)?

    Until he meets Castiel, the new mathematics teacher. Dean begins feeling things that he's not used to feeling...like longing.

    After a day of no blockers, the two men realize they're True Mates. But Dean isn't gay. He's not. Right?

    Enter internet quizzes, denial, best friends, denial, talking, denial...did I mention denial? But then there's acceptance...and love.

    Language:
    English
    Words:
    33,015
    Chapters:
    26/26
    Comments:
    88
    Kudos:
    552
    Bookmarks:
    107
    Hits:
    9,865
  14. Tags
    Summary

    This SPN Fanfiction story takes place in an alternate reality where Dean Smith and Sam Wesson lead two totally separate lives. Those two lives converge when each is having their own psychological meltdown through alcohol and drug dependency. Dean is forced into rehab while Sam enters it of his own accord. Supernatural occurrences lead the boys to solve a mystery as well as one of their own. This story was inspired by the FFDP song “The Tragic Truth.” These characters belong to Eric Kripke. I’m only playing in his sandbox. If this subject matter offends you, please feel free to move on. Thanks

    *This SPN Fanfiction story is complete.

    Series
    Language:
    English
    Words:
    19,227
    Chapters:
    8/8
    Comments:
    6
    Kudos:
    78
    Bookmarks:
    3
    Hits:
    625
  15. Tags
    Summary

    Castiel is back in the bunker after months on his own as a newly human, but he comes back with his own troubles. Lacking in proper sleep and comfort, Dean tries to help his friend while wondering if it was just comfort Cas wanted or something more.

    Series
    Language:
    English
    Words:
    23,355
    Chapters:
    7/7
    Comments:
    7
    Kudos:
    137
    Bookmarks:
    22
    Hits:
    4,110
  16. Tags
    Summary

    Dean Winchester isn’t having a good day. So, what’s new? His day only spirals further downwards after he discovers that his girlfriend’s been screwing around with his boss. Dean Winchester does what he does best. He gets shitface drunk. With inhibitions thrown to the wind, he hooks up with a guy for the first time in his young life. It’s only a kiss. One little kiss, but it sends John Winchester over the edge as he disowns his son. Dean’s left out in the cold, homeless. He finds out about the local homeless shelter in town. There, he meets a kind blue-eyed stranger who runs the shelter. Maybe one-winged doves can find love and happiness on the edge of seventeen?

    Series
    Language:
    English
    Words:
    30,691
    Chapters:
    21/21
    Comments:
    6
    Kudos:
    43
    Bookmarks:
    10
    Hits:
    1,240
  17. Tags
    Summary

    Dean Winchester’s day starts off badly. It goes downhill from there. The next day really isn’t any better. He wonders why these things keep happening to him until Sammy reveals certain things that he’s never heard. Maybe things aren’t as bad as they seem. Maybe everyone has days like these. If there’s one good thing about him, it’s that he’s resilient. He’s unsinkable. He’s like a bull in a China shop and nothing’s gonna get in his way.

    Series
    Language:
    English
    Words:
    4,890
    Chapters:
    2/2
    Comments:
    5
    Kudos:
    27
    Bookmarks:
    1
    Hits:
    608
  18. Tags
    Summary

    Dean Winchester tries to be the perfect son, brother, and hunter until he’s interrupted by a series of events that are beyond his control. Now, after refusing to rat out his family after a hunt gone sideways, he finds himself taken away from them. He’s remanded over to a Mental Hospital all due to some things he’s said while coming to after a concussion. He misses Sammy. He finds friendship in a mysterious blue-eyed man. Dean has to sink or swim if he wants to survive. He decides to swim.

    Series
    Language:
    English
    Words:
    20,327
    Chapters:
    7/7
    Comments:
    2
    Kudos:
    99
    Bookmarks:
    13
    Hits:
    1,692
  19. Tags
    Summary

    Dean Winchester is doing his number one job. His number one job is to take care of his baby brother, Sammy. That’s what he’s always done. That’s what he will forever do. But, what will happen when Sammy does things on his own without telling his older brother? Sammy finds out the hard way when Sammy does the crime, but big brother, Dean does the time.

    Language:
    English
    Words:
    11,635
    Chapters:
    4/4
    Comments:
    5
    Kudos:
    30
    Bookmarks:
    2
    Hits:
    655
  20. Tags
    Summary

    Ever since he’d dragged Cas out of the Empty, Dean had been making a point of being more open with Cas about his thoughts and feelings. Even if it took him a while to get there sometimes, he’d still try. All that Cas had to do in return was give Dean the time he needed to do it on his own terms

    And it was looking like something was bothering Dean right now, and Dean was ready to talk about it right now

    Series
    Language:
    English
    Words:
    1,533
    Chapters:
    1/1
    Collections:
    1
    Comments:
    18
    Kudos:
    244
    Bookmarks:
    20
    Hits:
    1,389

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