1 - 20 of 274 Works in Dean Winchester Has Self-Esteem Issues

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  1. Tags
    Summary

    Living in the small city of Lebanon, Kansas there is one highlight to your simple and quiet life. You call him Officer Sexy...but to his face it’s Officer Dean Winchester. He comes into the bakery you work at every morning and makes you blush like a schoolgirl. But you don’t take his flirting seriously since he does have a reputation. Why would he be interested in you of all people anyway? Little did you know Dean does actually have a mutual crush on you. When he finally works up the nerve to ask you out there’s a misunderstanding and he thinks you’re dating a coworker.

    Meanwhile your irresponsible older sister needs a place to stay. Not having the heart to turn family away no matter how much she aggravates you, you agree to let her stay with you for a while. Much to your dismay she starts dating none other than Officer Sexy. What happens after a series of events result in your true feelings for each other coming to light? Things get messy and complicated before they get better, that's for sure.

    Language:
    English
    Words:
    8,977
    Chapters:
    4/?
    Comments:
    6
    Kudos:
    9
    Bookmarks:
    8
    Hits:
    165
  2. 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:
    23,232
    Chapters:
    14/?
    Comments:
    194
    Kudos:
    483
    Bookmarks:
    81
    Hits:
    19255
  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:
    130,742
    Chapters:
    8/10
    Comments:
    128
    Kudos:
    86
    Bookmarks:
    18
    Hits:
    2056
  4. Tags
    Summary

    Dean has participated in the yearly zombie apocalypse thrown by the college for the past two years and he’s perfected the art of evading zombies. This year, he convinces Cas to join but has to make a bet to do so. Who will win the bet?

    Language:
    English
    Words:
    25,997
    Chapters:
    6/7
    Comments:
    29
    Kudos:
    44
    Bookmarks:
    2
    Hits:
    472
  5. 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:
    38,456
    Chapters:
    21/?
    Comments:
    235
    Kudos:
    348
    Bookmarks:
    56
    Hits:
    9602
  6. Tags
    Summary

    "Listen, Cas. I, uh... I've got somethin' to say."

    "Well, I'd be a little put out if you didn't."

    "You might be a little put out regardless," Dean muttered under his breath.

    OR

    Dean has got to let Cas know how he feels—so he can get past it. But how will Dean's best friend, an angel of the Lord, react to Dean's dirty little secret?

    Language:
    English
    Words:
    1,724
    Chapters:
    1/1
    Comments:
    7
    Kudos:
    47
    Bookmarks:
    5
    Hits:
    430
  7. Tags
    Summary

    “Hm.” Nicky’s clearly dissatisfied with that answer. “So no mentions of immortality at all? What about other gods? Pre-Abrahamic religions?”

    “Habibi,” Joe says, resting a hand on his shoulder. “Don’t overwhelm them.”

    Sam starts answering, talking about Gabriel double-timing as Loki, all the other gods they’ve met, the theological implications of one god creating many others, angels impersonating other gods, and Dean almost cares, but he can’t hear any of it. It’s white noise, blood rushing in his ears, all he can see is the slow caress of Joe’s thumb on Nicky’s shoulder, Nicky’s hand coming up to clasp at Joe’s.

    OR: Sam and Dean meet the Old Guard. It awakens a few things in Dean.

    Language:
    English
    Words:
    4,454
    Chapters:
    1/1
    Comments:
    21
    Kudos:
    244
    Bookmarks:
    24
    Hits:
    1282
  8. Tags
    Summary

    It took ten years to fix his soul. One month on earth.
    “You are good.” The angel whispered, pushing torn edges together and hoping, praying that somehow it would work when nothing else had. “You are a good man. You are the Righteous Man.”

    Language:
    English
    Words:
    647
    Chapters:
    1/1
    Comments:
    4
    Kudos:
    21
    Bookmarks:
    1
    Hits:
    143
  9. 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:
    5,431
    Chapters:
    7/?
    Comments:
    12
    Kudos:
    44
    Bookmarks:
    8
    Hits:
    1048
  10. 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:
    3
    Kudos:
    21
    Hits:
    242
  11. 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:
    77
    Bookmarks:
    14
    Hits:
    581
  12. 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:
    135,818
    Chapters:
    25/25
    Comments:
    130
    Kudos:
    276
    Bookmarks:
    65
    Hits:
    9689
  13. 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:
    11
    Hits:
    176
  14. 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:
    114
    Bookmarks:
    11
    Hits:
    1488
  15. 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:
    251
    Bookmarks:
    37
    Hits:
    5594
  16. 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:
    116
    Bookmarks:
    8
    Hits:
    903
  17. 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:
    28
    Bookmarks:
    2
    Hits:
    267
  18. 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:
    10
    Kudos:
    148
    Bookmarks:
    16
    Hits:
    1176
  19. 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:
    20
    Kudos:
    304
    Bookmarks:
    22
    Hits:
    2854
  20. 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:
    70
    Bookmarks:
    5
    Hits:
    1217

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