1 - 20 of 269 Works in Dean Winchester Has Self-Esteem Issues

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  1. Tags
    Summary

    In which Dean is a subby masochist but Cas is vanilla as fuck so they have Problems ™. And Dean being as good at communicating as frogs are at brain surgery, well that isn't helping either. Bonus: Sam banging his head against the wall in frustration because he has to witness the #drama.

    Language:
    English
    Words:
    4,998
    Chapters:
    6/?
    Comments:
    12
    Kudos:
    34
    Bookmarks:
    8
    Hits:
    668
  2. Tags
    Summary

    I really don't know what this is, the two chapters are kinda related but I got a little off topic with the second one so yeah.

    Dean feels love and he feels it hard.

    Language:
    English
    Words:
    1,398
    Chapters:
    2/2
    Comments:
    2
    Kudos:
    14
    Hits:
    137
  3. Tags
    Summary

    Cowboys from all over the American West travel to Abilene, Texas, just to get a taste of Dean Winchester, one of the only—and best—male prostitutes out there, and he makes good money from them, too. Unfortunately, most of that money goes toward his family, who he’s not even allowed to see on account of his no-good piece of shit daddy who kicked him out.

    When tenderfoot cowboy Castiel rides into town, Dean starts to crave something he hasn’t had in a long while— a real home.

    Together, Dean and Castiel have to navigate the inhospitable world of the American West, and discover for themselves what family means, when family pushes you away.

    **Previously titled "A Boy Whore From Abilene"**

    Language:
    English
    Words:
    99,753
    Chapters:
    6/10
    Comments:
    87
    Kudos:
    70
    Bookmarks:
    12
    Hits:
    1230
  4. Tags
    Summary

    Where does an Angel of the Lord go during a pandemic?
    He stays next to the Righteous Man.
    Like always.

    Language:
    English
    Words:
    6,376
    Chapters:
    1/1
    Comments:
    4
    Kudos:
    64
    Bookmarks:
    8
    Hits:
    433
  5. Tags
    Summary

    Castiel owns The Garrison, a popular club in a midsized Midwest town. He also has a dark past he can’t quite get away from and a darkness within, a dark, oily sludge, he's never quite been able to rid himself of.

    Dean is in yet another new town, his brother just left for college on the other side of the country and his dad just up and vanished in the middle of the night without warning. He’s alone, angry, and bristling with a recklessness that mimics the untamed inferno raging behind his ribcage, something he’s fought to tame his entire life.

    Does darkness always equate to evil? Does light always allude to purity?

    Or do both extremes consume entirely, simply in different ways?

    Can Castiel and Dean help contain the others demons before they become too much?

    Language:
    English
    Words:
    135,814
    Chapters:
    25/25
    Comments:
    119
    Kudos:
    238
    Bookmarks:
    53
    Hits:
    7813
  6. Tags
    Summary

    "And by some twist of fate or other mystical forces unknown, Dean’s birthday wish does come true after all. Though for many years to come, he will think back over the events that followed and wonder what might have been different had he wished for a dirt bike instead."

    Series
    Language:
    English
    Words:
    1,796
    Chapters:
    1/1
    Kudos:
    6
    Hits:
    116
  7. Tags
    Summary

    They had gotten Cas back. He was safe, he was himself, he was almost human and he was here. Chuck was gone, the kid was back to being a kid, albeit in an adult's body, the world was saved. It was too good to be true, really. And under normal circumstances, Dean would be waiting for the other shoe to drop. This time he didn’t need to. Wait, that is. Because Cas was in love with him, which - great! Awesome! If it weren’t for the fact that that was exactly what had gotten the angel killed.

    Even after saving Cas from the Empty, Dean blames the fact that Cas is in love with him for Cas's death. And because he loves Cas too and wants to keep him safe, he pushes him away.

    This story does have a happy ending, there'll just be a bit of suffering until we get there.

    Language:
    English
    Words:
    5,719
    Chapters:
    5/5
    Comments:
    40
    Kudos:
    103
    Bookmarks:
    10
    Hits:
    1370
  8. Tags
    Summary

    No one would love a Fat Nerd like Dean, at least that's what his ex would tell him. But maybe the blue eyes angle who works at the bookstore can change that

    (September 18, 2020)
    Hi everyone. I hope you’re all safe and healthy. I know it’s been a LONG time since I’ve updated but I just wanted to let you all know I’m still here and I do have plans for this story. I don’t know when I’ll be able to get back into it; but I’ll keep you all updated
    LOVE YOU ALL

    Language:
    English
    Words:
    27,864
    Chapters:
    16/16
    Comments:
    55
    Kudos:
    240
    Bookmarks:
    34
    Hits:
    5402
  9. Tags
    Summary

    Dean took Sammy and ran away from their abusive dad. Dean's worked as a mechanic his entire life in order to support Sam's dream of becoming a lawyer. Then someone catches Dean doing advanced math and wants to know more about Dean's life and who he is.

    Something bad happens and Dean needs help. He needs to face his fear and go to court again. He doesn't want to burden Sam, who can he call? Will Dean be able to stay sober?

    Language:
    English
    Words:
    37,178
    Chapters:
    20/?
    Comments:
    221
    Kudos:
    323
    Bookmarks:
    53
    Hits:
    8696
  10. Tags
    Summary

    Dean comes out to Sam after a little pep talk from Bobby.

     

    Recommended to read the other work in this series first, but it's not compulsory and this fic should make sense either way.

    Series
    Language:
    English
    Words:
    1,687
    Chapters:
    1/1
    Comments:
    3
    Kudos:
    88
    Bookmarks:
    6
    Hits:
    692
  11. Tags
    Summary

    Thinking about it made him feel like a goddamned girl, but at some point, the truth became unavoidable: Dean was lonely.

    Sam was off in school, making something of himself, too busy for the dwindling, already-distant phone calls of his first days in Stanford. Dad checked in every now and then, bouncing from hunt to hunt with the same single-minded zeal he’d always had. When he called, he’d say something like, “I’m in Nevada hunting a wraith,” and Dean would ask, “Want me to come by?” and Dad said no every time.

    Series
    Language:
    English
    Words:
    7,335
    Chapters:
    4/?
    Comments:
    9
    Kudos:
    27
    Bookmarks:
    2
    Hits:
    236
  12. Tags
    Summary

    An AU where Bobby takes in the Winchester boys after realising how much of an asshole John Winchester is towards his kids.

    Series
    Language:
    English
    Words:
    8,376
    Chapters:
    1/1
    Comments:
    4
    Kudos:
    119
    Bookmarks:
    13
    Hits:
    934
  13. Tags
    Summary

    Omega Dean is interviewing for a job, Alpha Castial has a different position in mind for the omega though after meeting him, that of a breeder hanging off his knot. Castiel quickly makes it reality. (Old prompt from the kink community, when I find the link I'll include it).

    Dean's desperate for a job since his hours at the bar got cut. He's got bills to pay and doesn't want to be a burden to his younger brother. Then suddenly he finds the perfect, ideal job working in his field fall into his lap. Working for the Novaks is a dream, except Castiel Novak turns out to be another asshole alpha who just wants a sweet, naïve omega to play with. There might be more than meets the eye but Dean can't think about that right now.

    Language:
    English
    Words:
    18,904
    Chapters:
    12/?
    Comments:
    175
    Kudos:
    432
    Bookmarks:
    73
    Hits:
    16125
  14. Tags
    Summary

    John finds out that Dean has been cutting himself and dumps him and Sam at Bobby's.

    Series
    Language:
    English
    Words:
    8,494
    Chapters:
    2/2
    Comments:
    18
    Kudos:
    227
    Bookmarks:
    16
    Hits:
    2237
  15. Tags
    Summary

    Castiel Novak and Dean Winchester have been dating for 5 years, two of which have been rough, particularly on Dean.

    Language:
    English
    Words:
    4,089
    Chapters:
    2/2
    Comments:
    14
    Kudos:
    66
    Bookmarks:
    4
    Hits:
    1179
  16. Tags
    Summary

    Dean Winchester knew three things for certain.

    One. Just because he served customers didn't mean he actually liked doing it.

    Two. He was absolutely in love with his best friend.

    Three. He wasn't even supposed to be here today.

    Language:
    English
    Words:
    16,084
    Chapters:
    4/4
    Comments:
    17
    Kudos:
    134
    Bookmarks:
    20
    Hits:
    1583
  17. Tags
    Summary

    Dean had dreamed of Castiel climbing into his bed, on more than one occasion.

    Of course, in Dean's dreams, Castiel had been awake...

    Language:
    English
    Words:
    5,871
    Chapters:
    1/1
    Comments:
    253
    Kudos:
    1150
    Bookmarks:
    133
    Hits:
    4266
  18. Tags
    Summary

    Dean’s been taking care of everyone else for as long as he can remember. Is it so wrong for him to want someone to take care of him for a change? If so, sue him. When smooth-talking alpha Michael shows up at Dean’s job and promises him to do just that, Dean wants to believe him. Instead, Michael leaves the hard-working omega alone and pregnant. Refusing to go home and deal with John’s abuse, Dean finds a little studio apartment and buckles in for the long haul.

    Enter handsome alpha Jimmy Novak, who Dean finds himself drawn to regardless of the lack of physical attraction between them. When an emergency calls Jimmy back to his family home, Dean goes along to support him. Tragedy strikes along the way, leaving Dean in the care of Jimmy's family. Here Dean finds himself drawn to Jimmy's twin brother, Castiel, in all the ways he and Jimmy weren't drawn to each other.

    Language:
    English
    Words:
    32,012
    Chapters:
    13/13
    Comments:
    61
    Kudos:
    218
    Bookmarks:
    46
    Hits:
    3029
  19. Tags
    Summary

    When Dean gets hit by a spell/curse/whatever the hell it was that happened back in that alley, that turned him female, saying that he was not dealing with it well was a vast understatement. Because there are things where there shouldn't be, and things not there that should be, and it's just an upsetting and unpleasant experience all around (basically, panic attacks, identity crises, all that fun stuff). So when he's pretty much forced into taking Cas along with him as a babysitter on a freaking cake walk of a vamp hunt, one that was supped to help distract him and try and get some of his aggression out, the already short fuse on his rage explodes. Although sometimes, talking out your problems and actually exploring your feelings helps, believe it or not. Especially when some of those feelings involve a certain angel, who also has a few feelings himself.

    Okay, maybe the spell was only 99% terrible.

    Language:
    English
    Words:
    5,941
    Chapters:
    1/1
    Comments:
    5
    Kudos:
    87
    Bookmarks:
    10
    Hits:
    847
  20. Tags
    Summary

    What started as a collection of drabbles exploring the idea that Dean and Cas had a sexual relationship prior to 15x18. Now has a plot of its own. Very angsty due to canon-compliance.

    Not every chapter is explicit; they are tagged individually. Each chapter is around 2k words.

    Language:
    English
    Words:
    38,521
    Chapters:
    12/12
    Comments:
    115
    Kudos:
    329
    Bookmarks:
    77
    Hits:
    5518

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