1 - 20 of 120 Works in Dean Winchester Has a Sexuality Crisis

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  1. Tags
    Summary

    Dean took care of the nuns just like I thought he would, but I don't think I'm going to be sending him on any more solos soon. That one was a little tense.

    Dean goes on his first ever solo hunt. He is seventeen.

    Language:
    English
    Words:
    2,066
    Chapters:
    1/?
    Comments:
    4
    Kudos:
    2
    Hits:
    2
  2. Tags
    Summary

    Dean is both stubborn and scared. Thanks to years of trauma, he's terrified to confront his feelings for Castiel. But surely a profound bond such as theirs and a chance at legitimate happiness can break or at least rattle the veteran hunter's resolve.

    Language:
    English
    Words:
    10,549
    Chapters:
    4/5
    Comments:
    4
    Kudos:
    35
    Bookmarks:
    6
    Hits:
    388
  3. Tags
    Summary

    Sam and Dean are working a case in New York City. Dean gets confronted with the past and the guilt about his own emotions.

    Language:
    English
    Words:
    6,693
    Chapters:
    5/?
    Comments:
    10
    Kudos:
    26
    Bookmarks:
    4
    Hits:
    386
  4. Tags
    Summary

    Thirteen-year-old Dean is looking forward to going back to school after Christmas Break because of the arrival of his new neighbor, Anna. Already completely infatuated, Dean and Anna gravitate toward each other quickly. Yet, throughout their years of school, he finds himself more and more interested in her bizarre and a bit offbeat younger brother.

    Language:
    English
    Words:
    7,350
    Chapters:
    2/?
    Kudos:
    2
    Bookmarks:
    1
    Hits:
    66
  5. Tags
    Summary

    Sam and Dean have a little chat about Cas. Dean tries not to gay panic.

    Series
    Language:
    English
    Words:
    630
    Chapters:
    1/1
    Collections:
    1
    Comments:
    3
    Kudos:
    18
    Bookmarks:
    1
    Hits:
    103
  6. Tags
    Summary

    “Never?” He asks. He just can’t understand it. He’d wanted to have sex pretty much since he went through puberty. Cas was older than life on Earth, and he’d never been tempted?

    “Well.” Cas’s eyes drop from Dean’s face to the table. “Not never.” Dean barely gets a chance to be vindicated before Cas says “Over the last several months, I have realized that I am attracted to you.”

    How the scene in Free to Be You and Me would have gone if Dean had been a little less oblivious and Cas had been a little more open about why he didn't want to sleep with Chastity the prostitute.

    Language:
    English
    Words:
    4,259
    Chapters:
    1/1
    Comments:
    23
    Kudos:
    138
    Bookmarks:
    9
    Hits:
    661
  7. Tags
    Summary

    "Okay, let's be clear on one thing from the start. This is not a lifetime movie and I'm straight, so no falling in love, get it?"

    "I get it, Dean," Castiel nods.

    Well, that's it then, apparently Dean is going to a fancy engagement party with his new fake boyfriend. What a weird day.

    Language:
    English
    Words:
    48,019
    Chapters:
    8/8
    Comments:
    147
    Kudos:
    401
    Bookmarks:
    68
    Hits:
    4337
  8. 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:
    100,357
    Chapters:
    22/?
    Comments:
    498
    Kudos:
    781
    Bookmarks:
    134
    Hits:
    19112
  9. Tags
    Summary

    When Rowena bets the Winchesters they can't go a single month as women, Dean thought it'd be the easiest favor they ever won, Sam's just reluctantly along for the ride, and with the Book of the Damned at stake, there's no backing out.

    31 days in a girl body? What could possibly go wrong?

    OR

    Sam and Dean Smash the Patriarchy

    Series
    Language:
    English
    Words:
    46,898
    Chapters:
    14/15
    Comments:
    83
    Kudos:
    328
    Bookmarks:
    66
    Hits:
    5763
  10. Tags
    Summary

    Dean Winchester is what many would consider a hopeless cause.
    With sticky fingers, a below c average and a mouthy attitude, even Dean cant see his life changing around. Not that he cares, considering his only plan in life is to make sure his twelve year old brother is okay.
    Of course that is until one to many slip ups with the cops and he's sent to a boys home in Hurleyville, New York; where he meets Castiel Novak.
    Rich, slightly stuck up, and with every aspect of his life planned out, Castiel might as well be night to Dean's day. Of course there's more then meets the eye, and maybe him and Cas have more in common then Dean would ever guess, starting with their music taste.

    Language:
    English
    Words:
    6,872
    Chapters:
    5/?
    Comments:
    13
    Kudos:
    38
    Bookmarks:
    5
    Hits:
    602
  11. Tags
    Summary

    mourning the loss of his brother Sam (he's fine, he just ran away), Dean Winchester is transported to Brakebills, a magical school for magicians.

    Series
    Language:
    English
    Words:
    358
    Chapters:
    1/?
    Kudos:
    2
    Bookmarks:
    1
    Hits:
    41
  12. Tags
    Summary

    New at being human, Castiel doesn't know a lot about Christmas traditions, but when a case involves them infiltrating a couple's only Christmas party, Cas wants the full experience.

    Including mistletoe.

    Language:
    English
    Words:
    7,265
    Chapters:
    1/1
    Collections:
    1
    Comments:
    8
    Kudos:
    51
    Bookmarks:
    6
    Hits:
    497
  13. Tags
    Summary

    So I set it up as 15x19 did happen, but 15x20 did not. After they defeated Chuck, Jack opened a portal and Sam and Dean stole Cas out of the Empty (the Empty thanked them for it and promised to separate them on a quantum level if they ever returned) by taking his grace, and they settled back down in the bunker.

    So see, everything was perfect and nothing was awkward! Because, see, one thing Dean and Cas are absolutely fucking GREAT at is not talking. So that, jack save their immortal souls, is what they did.

    Language:
    English
    Words:
    1,581
    Chapters:
    1/1
    Comments:
    16
    Kudos:
    90
    Bookmarks:
    14
    Hits:
    554
  14. Tags
    Summary

    CODA 15x18 - TW flashbacks for Cas, mentions of self injurious behavior, panic attacks, references to Cas's d**th

    Castiel has confessed his love for Dean and been taken to the empty (because the CW is homophobic). A heartbroken Dean, a desperate Sam, and a longing Jack need to come up with a way to get back the angel and save the world. They always find a way, but this is going to be difficult...

    Meanwhile, Castiel is subjected to reliving his nightmares and regrets for eternity. For once, he's the one who needs saving. An empty casing, will Dean be able to break down his walls and give him some much needed comfort?

    **I wanted this story to be as in character as possible, in an attempt to give us all some closure. That being said, I kind of projected my feelings onto these characters. Oops. I just wanted to give Cas the love he deserves from his family, while finishing the SPN story as best I could.

    Language:
    English
    Words:
    1,790
    Chapters:
    1/1
    Comments:
    2
    Kudos:
    103
    Bookmarks:
    11
    Hits:
    821
  15. Tags
    Summary

    Maybe it’s the cynic in him. The hunter, always under the surface of any quietude he ever found. Or maybe it’s just that he has always had trouble with blind faith. But after a while (a blink? A decade? A century?), Dean raises his eyebrows, looks around, and says—

    “Uh. No.”

    It’s so close. Just so slightly imperfect. And maybe, he analyzes, maybe that’s the final knell of this bell called contentment. Dean’s experience with happiness has always been that last rise in the road, right before it turns. Right before fate comes barreling around the corner head on.

    He turns in his spot on the bridge, and suddenly Sam is like a cellophane film through which he can see the light streaming, and the taste of cheap beer on his tongue is much, much older a memory than it should be.

    “Oh, you’re good,” he says, and means it.

    Language:
    English
    Words:
    7,865
    Chapters:
    1/1
    Collections:
    2
    Comments:
    156
    Kudos:
    1071
    Bookmarks:
    308
    Hits:
    6140
  16. Tags
    Summary

    When Castiel still hadn’t moved after Dean had changed into his pajamas his worry started to eat at him almost painfully.
    “Cas?”
    Finally, the angel turned around. His eyes were red-rimmed and for a second Dean thought Cas had cried but there were no trails of tears on the cheeks and he otherwise didn’t look like he had cried either.

    Collection of onseshots based on dialogue prompts. Destiel.

    Language:
    English
    Words:
    7,398
    Chapters:
    6/?
    Comments:
    2
    Kudos:
    16
    Bookmarks:
    1
    Hits:
    564
  17. Tags
    Summary

    Castiel hates his job as a personal assistant. And because not too many people seem to need the help, with the exception of little old ladies who are in need of a maid to reach the high places, he's in need of better paying clients. Luckily for him, his brother, Gabriel, has friends in high places.

    Dean Winchester is one such friend. Dean is a model, and his frantic schedule has his other priorities slipping through his fingers. He's been in need of live-in help for a while, someone to take care of the house while he's away. But he's either too proud or too stubborn to ask for it.
    Of course Castiel wants the job! He'd be making a considerable amount more than he was making before and he'd be living in a large house. And so what if his new client happens to also be gorgeous, that only makes it more tempting.

    Nothing bad could happen, right?

    Language:
    English
    Words:
    4,201
    Chapters:
    1/?
    Comments:
    1
    Kudos:
    9
    Bookmarks:
    1
    Hits:
    141
  18. Tags
    Summary

    The last time Cass died, it had destroyed him. Weeks of drinking, locking himself away in the bunker binging shows and eating crap when he even bothered to eat at all. It had left him a wreck. But a wreck who didn’t know.

    Now, there wasn't any hope left. He was seconds away from shattering, and Sam wasn't any better. There was nothing to hold them together—no tape, no glue strong enough to piece together their losses.

    He just never thought that at the end of the world, Cass wouldn't be there.

    //

    Filling in a moment we should have gotten in some form in 15x19. Or: Dean Winchester actually considers his emotions.

    Series
    Language:
    English
    Words:
    2,963
    Chapters:
    1/1
    Comments:
    23
    Kudos:
    181
    Bookmarks:
    16
    Hits:
    1357
  19. Tags
    Summary

    The strange development of falling for what you're against.

    OR

    Castiel Novak and Sam Winchester are great friends but Sam's older brother gets under Castiel's skin.

    Language:
    English
    Words:
    45,196
    Chapters:
    17/?
    Comments:
    111
    Kudos:
    555
    Bookmarks:
    73
    Hits:
    14844
  20. Tags
    Summary

    He should be so much more weirded out and upset by these… feelings than he is.

    Gabriel’s voice shocks him back into his body and his eyes snap open. “You need some help with that?”

    Dean stares at him, uncomprehending, then looks down when Gabriel nods in the direction of his waist. He hasn’t been doing a good enough job of hiding his boner, evidently.

    or

    There's apparently a security camera system in the Bunker. Dean is not putting it to good use. (Or he is, depending on your definition of 'good use'.)

    Language:
    English
    Words:
    4,458
    Chapters:
    1/1
    Comments:
    6
    Kudos:
    64
    Bookmarks:
    5
    Hits:
    906

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