1 - 20 of 213 Works in Prostitute Dean Winchester

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  1. Tags
    Summary

    Dean Winchester is an omega who was abandoned by his mother at a young age, being left behind with his bitter and abusive father. He’s alone, scared, and developmentally behind, childlike and not even able to read when he’s thrown out on his ass as a teenager. By the time he’s 27 he’s no better off and more damaged than ever, homeless and working on the street. He tries to be happy, childlike mind clinging to hope, but he’s tired. He waits for an angel.

    Castiel is an alpha who’s recently experienced a fall from grace after falling into a psychotic episode at work and attacking a man while on duty. He’s lost his job and now works nights at a run down gas station, living paycheck to paycheck and preparing to go before the board to plea his case for why his credentials shouldn’t be taken away. He’s going to get his life back together, there’s only one problem. Castiel believes he’s God-like, a twisted angel of justice, and takes that belief to violent extremes.

    *watch me write about Cas’s decent into madness and violence/Dean’s tragedy of a life but make it a love story.*
    *All the warnings, this one gets dark friends (but I promise a happy ending).*

    Series
    Language:
    English
    Words:
    223,112
    Chapters:
    33/?
    Comments:
    597
    Kudos:
    544
    Bookmarks:
    75
    Hits:
    17,013
  2. Tags
    Summary

    Dean has dug quite a hole for himself, or maybe he is the hole being dug into.

    Posting that video of a fantastic gloryhole session was a mistake, garnering the attention of not only hundreds of thousands of views but also of the dangerous man who dicked him so good. He easily hunts down Dean, trapping him in one hell of a predicament as he finds himself at the whim of Castiel's will.

    Language:
    English
    Words:
    69,693
    Chapters:
    3/?
    Comments:
    21
    Kudos:
    89
    Bookmarks:
    22
    Hits:
    4,078
  3. Tags
    Summary

    Dean's got a pretty simple schedule, working at Bobby's auto shop during the day, getting back home to make Sammy some dinner, and returning to his « Night Shift at the diner. » Sometimes John is home, and things are good (well, not always, but a win's a win), most of the time he's not, and Dean's gotta feed his little brother with what money he can make. It's simple, not perfect, but Dean's made peace with that.

    On a night that goes fucking wrong, he ends up naked next to a bleeding corpse and staring down the barrel of a 45. And it may be the adrenaline talking, but there's something in the crystal blue eyes staring coldly at him that just seem to resonate in his fucked up mind.

    Language:
    English
    Words:
    33,047
    Chapters:
    9/?
    Comments:
    56
    Kudos:
    157
    Bookmarks:
    21
    Hits:
    2,702
  4. Tags
    Summary

    Part of my Stripper Dean series.
    The first meeting of Dean and Castiel.
    Dean is a prostitute for the Hell Hounds. Castiel is a crime boss trying to take their territory. Maybe they can help each other out.

    Series
    Language:
    English
    Words:
    11,593
    Chapters:
    8/8
    Comments:
    55
    Kudos:
    106
    Bookmarks:
    9
    Hits:
    2,170
  5. Tags
    Summary

    Sam never enjoyed going home for the holidays. It was the most depressing-fucking thing ever- no wonder Jess'd found a way out of it. Oh well, there was always Dean to make fun of. That never got old.

    Language:
    English
    Words:
    1,427
    Chapters:
    2/6
    Comments:
    4
    Kudos:
    37
    Bookmarks:
    6
    Hits:
    834
  6. Tags
    Summary

    Sometimes a vacation changes you forever. Especially a complicated drama filled family vacation.

    Wrote this as a little treat for y’all to read during the limbo between Christmas and new years. Enjoy :)

    Language:
    English
    Words:
    28,175
    Chapters:
    10/10
    Comments:
    5
    Kudos:
    22
    Bookmarks:
    6
    Hits:
    601
  7. Tags
    Summary

    Dean will do anything for Sam.
    Dean will use everything he has for Sam.
    Even if that includes his own body.
    For Sam. He can do it.

    Language:
    English
    Words:
    14,320
    Chapters:
    8/8
    Comments:
    8
    Kudos:
    92
    Bookmarks:
    12
    Hits:
    1,375
  8. Tags
    Summary

    Recently reunited with his brother after their time spent apart, Dean has a hard time keeping his way to make some quick money a secret from Sam, who was never supposed to know.
    When Sam eventually finds out about Dean’s secret activities and sees what it does to him, he tries his best to ease Dean’s pain, in a way that only he is able to.


    Set pretty much right after the pilot, even before episode 2. Dean's POV.

    Language:
    English
    Words:
    5,412
    Chapters:
    1/1
    Comments:
    8
    Kudos:
    135
    Bookmarks:
    17
    Hits:
    1,590
  9. Tags
    Summary

    Standing in a relatively open part of the trail was a sasquatch. The moon hit him like a spotlight, illuminating every wiry hair from the crown of his head to his ankles. Beneath his hairs, stoic muscles kept the creature motionless. He wasn’t nearly as tall as Dean had thought he would be, but he was still massive. And he was naked. Very obviously naked.

    Language:
    English
    Words:
    4,287
    Chapters:
    1/1
    Collections:
    1
    Comments:
    2
    Kudos:
    15
    Bookmarks:
    1
    Hits:
    387
  10. Tags
    Summary

    Dean left behind the life of high society and a pre-determined marriage to carve a life out for himself. Working at the salvage yard by day, and an in-demand high end prostitute by night, he's mostly happy.
    Castiel Novak graces the center of a popular magazine as "Most Eligible" Alpha. He's running the Detroit branch of the family company, but his dating life is lacking.
    Balthazar suggests visiting a local brothel.

    Language:
    English
    Words:
    21,133
    Chapters:
    17/17
    Comments:
    89
    Kudos:
    600
    Bookmarks:
    72
    Hits:
    13,114
  11. Tags
    Summary

    Kinktober 2023 #9

    Prompt: Prostitution
    Pairing: Castiel/Dean Winchester (Sub!Top Cas, Dom!Bottom Dean)

    Synopsis: Castiel gets dragged by his brother, Gabriel, to a strip club. While sitting inside, Gabriel leaves to go along with some girls, and Castiel is convinced he’s going to have an awful time– that is, until an attractive male stripper catches his eye.

    Language:
    English
    Words:
    3,103
    Chapters:
    1/1
    Collections:
    1
    Comments:
    3
    Kudos:
    127
    Bookmarks:
    8
    Hits:
    1,285
  12. Tags
    Summary

    Dean is on his own, Sam is at Stanford, John is fucked off somewhere... and Dean's actually miserable but trying to act like he's not. He gets a solo case from Bobby and has to focus on that. But weird happenings cause him to be stuck in this town for a lot longer than he anticipated...

    Language:
    English
    Words:
    3,686
    Chapters:
    3/?
    Comments:
    2
    Kudos:
    8
    Bookmarks:
    1
    Hits:
    208
  13. Tags
    Summary

    PodFic version of Sweet Sixteen by Edge_of_Clairvoyance

    John was going slowly enough to get a glimpse of the hookers' faces. Some of them looked old and worn, and others looked no more than goddamned kids.

    And then his heart gave a lurch in his chest and he nearly slammed on the brakes, remembering at the last moment to ease off so the car wouldn't veer. His hands trembled so badly he had to tighten his fingers on the wheel to keep them steady. He crawled along the curb, then slowed to a stop. The boy who had been standing there came around to the driver's side and leaned over the foggy window, one hand braced on the roof.

    "Lookin' for company?"

    Series
    Language:
    English
    Words:
    13
    Chapters:
    1/1
    Kudos:
    7
    Hits:
    773
  14. Tags
    Summary

    Dean is a courtesan and the star of a nightclub longing for a normal life and a chance to find his brother again. Castiel is an angel living in the shadow of his siblings, wanting a chance to make his own choices for once. One night their paths cross.

    This story is about truth, beauty, freedom but above all things, this story is about love.

    Language:
    English
    Words:
    10,377
    Chapters:
    2/2
    Collections:
    1
    Comments:
    8
    Kudos:
    52
    Bookmarks:
    11
    Hits:
    647
  15. Tags
    Summary

    Nowhere man, give me your hand
    Let me save you, let me save you
    Faithless man, give me your hand
    Let me save you, let me save you

    Language:
    English
    Words:
    34,462
    Chapters:
    28/?
    Comments:
    233
    Kudos:
    426
    Bookmarks:
    54
    Hits:
    10,073
  16. Tags
    Summary

    It takes some time, but Dean learns that maybe it doesn't hurt to let people help shoulder the burden for him.

    In which Dean's a whore who barely talks and Cas is a depressed undergrad who thought blinker fluid was a thing for longer than he'd care to admit.

    Language:
    English
    Words:
    12,582
    Chapters:
    4/4
    Collections:
    1
    Comments:
    30
    Kudos:
    338
    Bookmarks:
    48
    Hits:
    2,429
  17. Tags
    Summary

    Johnny and his crew just ripped off one of the biggest gangs in the area and are ready to celebrate. Luckily a hooker they know, Nicki, and her friend Sweetcheeks, are there to make it a night to remember.

    This is a prequal in the Stripper Dean series. Dean is 15 in this story.

    Series
    Language:
    English
    Words:
    6,452
    Chapters:
    5/5
    Comments:
    10
    Kudos:
    92
    Bookmarks:
    4
    Hits:
    1,223
  18. Tags
    Summary

    They say doomed species always fuck the hardest. Dean's ready and willing to test that theory.

    Or: Castiel needs someone to carry his eggs so he can save his species. He finds Dean.

    Language:
    English
    Words:
    15,463
    Chapters:
    1/1
    Comments:
    14
    Kudos:
    110
    Bookmarks:
    17
    Hits:
    6,441
  19. Tags
    Summary

    Sixteen year old Dean Winchester is forced into prostitution as a last restore to take care of his younger brother. Things, including his self worth, steadily go downhill until a particular angelic client shows him that he is more than just a body.

    Language:
    English
    Words:
    21,656
    Chapters:
    9/?
    Comments:
    28
    Kudos:
    172
    Bookmarks:
    33
    Hits:
    5,294
  20. Tags
    Summary

    Sam was severely sheltered from various aspects of his childhood.
    Dean shielded him from it all, taking on many traumatizing dilemmas.
    Thus, at times, Sam’s words maintain a greater effect than he realizes.
    Effects that send Dean spiraling into unwanted memories.

    Language:
    English
    Words:
    948
    Chapters:
    1/1
    Comments:
    1
    Kudos:
    82
    Bookmarks:
    6
    Hits:
    1,465

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