1 - 20 of 154 Works in Dean Winchester Has a Sexuality Crisis

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  1. Tags
    Summary

    For five years Castiel Novak was CEO Dean Winchester's perfect bodyguard and assistant. Novak, the only man the powerful leader trusts. But one day, Castiel Novak quits his job all of the sudden because he wants to marry his girlfriend and have a normal life, leaving Dean speechless.
    Dean realizes he knows nothing about the best employee he had. As his world turns unexpectedly upside down, the famous CEO decides become Novak's friend to keep him close again.
    But try to become a "good selfless friend" is something new for Dean... and even more when he discovers through that path he may have feelings for Castiel.

    Language:
    English
    Words:
    7,870
    Chapters:
    3/8
    Comments:
    24
    Kudos:
    54
    Bookmarks:
    14
    Hits:
    599
  2. Tags
    Summary

    Dean thought his feelings, especially towards Cas, were a secret. He also thought he was straight, too, though, so maybe his judgement isn't exactly the best about matters of the heart.

    Suptober, Day 4: Secrets

    Series
    Language:
    English
    Words:
    2,135
    Chapters:
    1/1
    Collections:
    1
    Comments:
    3
    Kudos:
    63
    Bookmarks:
    8
    Hits:
    486
  3. Tags
    Summary

    Dean and Sam are planning to spend Christmas alone this year, just like every other year since Dad died. They have their miniature fake tree with the few gifts underneath that the two of them can afford on Dean’s bartender wages and Sam’s campus job. They have a “plant-based roast” in the fridge for Christmas dinner because, to Dean’s chagrin, Sam went vegan over the summer. It’s a pretty uneventful end to 2015, all things considered.

    Then, the morning of December 23rd, a pipe bursts in the apartment of one of Sam’s friends, and he comes over to stay until his landlord gives him the all-clear to return. Dean meets him at breakfast on Christmas Eve, and…crap. He’s buff. And hot. And flirty. And he speaks all sorts of languages in that deep, sexy voice of his.

    But Dean is straight! There’s no way he’ll make a total fool of himself and embarrass his brother. He’s got this.

    Language:
    English
    Words:
    3,004
    Chapters:
    1/3
    Collections:
    1
    Comments:
    5
    Kudos:
    39
    Bookmarks:
    7
    Hits:
    254
  4. Tags
    Summary

    Feeling shoved aside by the lack of progress in their relationship, Dean struggles with accepting that Sam is also dating Castiel. When a case sends them investigating a festival of love, Dean reluctantly attends, letting Sam and Cas be the undercover couple. When they run into people they know, Cas and Sam are found in a compromising position. Meanwhile, this feeds further into Dean’s uncertainty as he pretends to be single, as he struggles with accepting what he wants from his brother and his own insecurities.

    //

    In the wake of their newly discovered relationship, our boys figure out the finer details.

    Series
    Language:
    English
    Words:
    24,535
    Chapters:
    6/6
    Comments:
    48
    Kudos:
    48
    Bookmarks:
    5
    Hits:
    1065
  5. Tags
    Summary

    “Cas is coming home. I just thought you should know.”
    It’s those words from his best friend, Cas’ brother Michael, that unleash memories and feelings Dean Winchester hasn’t confronted in years. The way they parted thirteen years ago was terrible, there’s no other way to phrase it. Dean knows Cas has every right to be angry at him, yet the cold attitude still hurts. The fact that the adorable, pudgy nerd he once knew has turned into this smoking hot man doesn’t make it any better. And as if his own sexuality crisis isn’t enough, Dean’s daughter Grace seems to have found a new friend in none other than the man that makes Dean question his entire life as he knows it.

    Dean’s PoV of Angel Cookies.

    Series
    Language:
    English
    Words:
    139,807
    Chapters:
    31/31
    Comments:
    623
    Kudos:
    973
    Bookmarks:
    160
    Hits:
    26834
  6. Tags
    Summary

    u know exactly what this is

    Language:
    English
    Words:
    11,501
    Chapters:
    6/8
    Comments:
    23
    Kudos:
    67
    Bookmarks:
    13
    Hits:
    603
  7. Tags
    Summary

    Dean Winchester and Castiel Novak were childhood best friends. Then they were (sort of) lovers, and then, finally, enemies. Before that happened, though, they had made a pact that, if by the time they both turned thirty and hadn't found someone to marry, they'd marry each other. That was all a joke, though. They were only eight, it meant nothing. Dean hasn't even seen the dude since his senior year in high school.

    But then, of course, Sam has to go and canoodle with Gabriel, Cas's younger brother, and now they're engaged. Dean's happy for them, really. It's just that when they drag him along to spend holidays with the Novaks, and he has to see Cas again, he begins to resent them. Especially when they won't stop reminding him of that stupid contract.

    (It's going to be a long Christmas.)

    Language:
    English
    Words:
    14,111
    Chapters:
    3/?
    Comments:
    8
    Kudos:
    51
    Bookmarks:
    6
    Hits:
    556
  8. Tags
    Summary

    “Right. Of course. Even though everyone with eyes has already picked up on our dirty little secret, we mustn’t ever acknowledge it or speak of it, lest you spiral into a gay panic.”

    The King of Hell crashing at the bunker comes with questions from Sam and conversations with Crowley that Dean would very much rather not face. Both just want him to admit that something happened between Dean and Crowley during their Summer of Love. Crowley is somewhat more effective at eliciting a response.

    Language:
    English
    Words:
    3,888
    Chapters:
    1/1
    Comments:
    9
    Kudos:
    42
    Bookmarks:
    8
    Hits:
    303
  9. Tags
    Summary

    Fact: there’s some kind of spook or creature terrorizing couples at a hotel in Independence, Ohio.
    Fact: Sam broke his ankle, and is not up to playing husband with anyone.
    Fact: Dean’s gone and realized that he’s in love with Cas, and he kinda wants to do something about it. He— okay. He really wants to do something about it.

    Conclusion: Dean has a distinct opportunity, here.

    What could possibly go wrong?

    Language:
    English
    Words:
    5,016
    Chapters:
    1/1
    Comments:
    10
    Kudos:
    160
    Bookmarks:
    17
    Hits:
    950
  10. Tags
    Summary

    "Ordinary" has never been in the cards for the Winchester brothers, and this experience is definitely no exception.

    After a string of events - Sam, Dean, Cas, and Jack are suddenly forced to share the bunker with their female (alternate dimension) counterparts - Samantha (Sami), Deanna (Dea), Cassiel (Cassie), and Jane.

    With 8 people in the bunker, things go downhill quite quickly.

    Dean is extremely attracted to Cassie (Castiel's Female Counter Part) and when Cas walks in to find Dean kissing the female angel his jealousy overtakes him. Thankfully Deanna is more than willing to assist Cas in letting out some of his sexual frustration while in turn making Dean jealous. Dean knows he shouldn't care that Cas and Deanna hooked up, Cas is his best friend and only his best friend... right? But if that's the case then why exactly is he envious of Deanna's "interactions" with Castiel?

    Language:
    English
    Words:
    9,033
    Chapters:
    2/10
    Comments:
    10
    Kudos:
    24
    Bookmarks:
    10
    Hits:
    322
  11. Tags
    Summary

    Dean was supposed to be working backstage, not taking over one of the biggest parts in the play.

    Castiel was supposed to be walking Gabriel through his lines, not the school's golden boy who had no idea what he was doing.

    When the two boys start working together, assumptions are made and defied, minds are changed, and the magic of musical theater works a couple miracles...

    Language:
    English
    Words:
    4,142
    Chapters:
    1/1
    Comments:
    4
    Kudos:
    38
    Bookmarks:
    4
    Hits:
    324
  12. Tags
    Summary

    After defeating Chuck, and everyone is okay because I say so and fuck the finale, to avoid brewing tensions in the bunker, Team Free Will 2.0 goes bowling! Dean is gay and has a crisis good for him.

    Language:
    English
    Words:
    2,415
    Chapters:
    1/1
    Comments:
    4
    Kudos:
    52
    Bookmarks:
    1
    Hits:
    537
  13. Tags
    Summary

    "Go out with me," Dean says, and Cas's eyebrows disappear into the flop of his tousled hair.

    "What?"

    Dean clears his throat, that's the only part of him that he can move at this point. He’d meant to say something eloquent. Something like: I’d let you destroy every bit of me if that would make you happy. Something like: Try to kiss me, I don’t think I’d stop you. Because I never fought you, even when you were beating me to death, and kissing is so much gentler. He opened his mouth again, about to say something closer to those things, but all he can say is, "Please, Cas. Please."

    "Where?"

    "I don't know, just come."

    COMPLETE Destiel

    Language:
    English
    Words:
    3,911
    Chapters:
    1/1
    Comments:
    15
    Kudos:
    236
    Bookmarks:
    32
    Hits:
    1637
  14. Tags
    Summary

    Twitter prompt: kissing each other to prove there’s nothing there, even though, it’s a lie, and the kiss proves it

    Series
    Language:
    English
    Words:
    1,770
    Chapters:
    1/1
    Comments:
    14
    Kudos:
    203
    Bookmarks:
    21
    Hits:
    1020
  15. Tags
    Summary

    The Winchesters hop the pond to investigate the dead being brought back to life and collaborate with Jack Harkness and the Torchwood team. Meanwhile, Jack notices the connection between Dean and Castiel and decides to help Dean deal with his denial.

    Language:
    English
    Words:
    21,655
    Chapters:
    15/15
    Comments:
    53
    Kudos:
    178
    Bookmarks:
    31
    Hits:
    2767
  16. Tags
    Summary

    Everyone around them heard songs they were never meant to listen to. Bobby used to tell them how strange it felt, not hearing his wife’s humming in his head anymore after she died. Charlie always talked about her songs with a glint of excitement in her eyes, absolutely thrilled to one day meet this soulmate who listened to movie soundtracks and anime openings.

     

    Everyone they ever knew heard the songs.

    Everyone, except themselves.

    Language:
    English
    Words:
    2,761
    Chapters:
    2/?
    Collections:
    1
    Comments:
    4
    Kudos:
    20
    Bookmarks:
    2
    Hits:
    287
  17. Tags
    Summary

    Dean has planned the night days ago. He is ready to propose but it's missing the certain je ne sais quoi. When the carnival comes into town everything seems to fall into place.

     

    This is a prompt ff because someone on Twitter mentioned that Dean should have proposed to Cas with his silver ring and the thought didn't leave my head, so here we are.

    Language:
    English
    Words:
    4,712
    Chapters:
    1/1
    Comments:
    2
    Kudos:
    39
    Bookmarks:
    10
    Hits:
    331
  18. Tags
    Summary

    And now at age 42, Dean's happily married with a handful of kids that are his in every way that matters, living in the suburbs with a big kitchen and a deck out back, and it should make those moments feel like a lifetime ago.

    But he's still somehow there. They're still fresh in his mind as if they happened a few days ago, the feeling of fear still fresh. And even though he's come so damn far, he's gotten farther than he ever thought he would, he still feels like that terrified little kid again.

    All because of some stupid, flimsy piece of fabric.

    Language:
    English
    Words:
    2,429
    Chapters:
    1/1
    Comments:
    5
    Kudos:
    121
    Bookmarks:
    10
    Hits:
    650
  19. Tags
    Summary

    See title ^^^

    Language:
    English
    Words:
    2,224
    Chapters:
    1/1
    Collections:
    1
    Comments:
    15
    Kudos:
    229
    Bookmarks:
    27
    Hits:
    1954
  20. Tags
    Summary

    The Dean grows his hair out, starts feeling more comfortable in his sexuality and relationship with Cas, and slowly quits hunting fic; because I have to do everything myself.

    Language:
    English
    Words:
    11,004
    Chapters:
    4/4
    Comments:
    14
    Kudos:
    141
    Bookmarks:
    20
    Hits:
    1070

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