1 - 20 of 41 Works in Prostitute Sam Winchester

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  1. Tags
    Summary

    Another AU - Castiel is older, Russian, and has frightful power and connections. Sam is just a dirt poor club kid and occasional hustler that happens to catch his eye.

    Language:
    English
    Words:
    99,431
    Chapters:
    29/?
    Collections:
    1
    Comments:
    1850
    Kudos:
    1213
    Bookmarks:
    220
    Hits:
    44145
  2. Tags
    Summary

    Sam is the star prostitute of "The Harem," a fine, reputable establishment run and owned by Crowley, seller of bodily pleasures. Sam has everything: Instagram fame, fans, gifts, and adoring clientele. He has a good life for a slave and a whore, but something is missing. In all the opulence, pleasure, and comfort, Sam finds himself lonely and wanting something he's never really had: love. The only thing he's ever seen of love is between lovers who invite him into their bed for a threesome and money.

    This is a story of a man who has lost everything and yet has everything still to gain. Who started out as a slave, climbed the ranks at "The Harem," and overcame all the life has thrown at him so far. His future will be brighter than his past-- it has to be. It's a story of how much a human spirit can survive and eventually thrive. It's also a story of learning how to love and be loved in return.

    Language:
    English
    Words:
    21,358
    Chapters:
    14/?
    Comments:
    67
    Kudos:
    84
    Bookmarks:
    20
    Hits:
    2467
  3. Tags
    Summary

    Dean Winchester works in the human trafficking unit for the Vice Control Section of the Chicago PD. While undercover, Dean meets "Baby Boi" aka Sam, an underage prostitute with a strange fascination for the macabre. Sam has cast himself as Bonnie in a real life reenactment of the infamous outlaw duo, insisting that Dean is his Clyde. When Dean finally agrees, they run off to fulfill each other's deepest, darkest fantasies. For Sam, it's a dream come true; until Dean starts to spiral out of control.

    Language:
    English
    Words:
    71,595
    Chapters:
    18/21
    Comments:
    512
    Kudos:
    811
    Bookmarks:
    158
    Hits:
    17369
  4. Tags
    Summary

    Sam is fourteen and now the stunning image of sweet temptation.

    Language:
    English
    Words:
    597
    Chapters:
    1/1
    Comments:
    6
    Kudos:
    54
    Bookmarks:
    2
    Hits:
    1701
  5. Tags
    Summary

    kinktober day 29 - Glory hole | Double (Or more) Penetration | Sleepy Sex | Massage

    It takes a lot of money to keep the Winchesters moving around like they do, and why not cash in on Sam's oral fixation? Glory holes are a plentyful resource scattered through the entirety of the US, and Sam's knees have seen plenty of them. We join him (and his bodyguard/pimp/brother) at the end of a long shift.

    Series
    Language:
    English
    Words:
    3,295
    Chapters:
    1/1
    Comments:
    19
    Kudos:
    131
    Bookmarks:
    12
    Hits:
    2779
  6. Tags
    Summary

    On this day Gabriel had just turned thirty-give, and it was a day to celebrate. Not with his family and friends… that, he kept for later. No, what Gabriel truly wanted was company of another kind. The kind of company with which he could explore his sexual fantasies. And as a bonus, the escort he had ordered had been a gift from his good old friend Balthazar. ‘Happy birthday, Gabriel, have yourself one of my best workers, my treat’. Who was he to refuse such a generous offer?

    Language:
    English
    Words:
    5,298
    Chapters:
    1/1
    Comments:
    3
    Kudos:
    76
    Bookmarks:
    8
    Hits:
    909
  7. Tags
    Summary

    Dean cruises down the street looking for some fun.

    Language:
    English
    Words:
    2,789
    Chapters:
    1/1
    Comments:
    12
    Kudos:
    46
    Bookmarks:
    1
    Hits:
    833
  8. Tags
    Summary

    Dean is a high-ranking demon in the Order of Azazel but due to a dead torture victim he is shunned and has to work as a ‘glorified babysitter’ for a young boy the Generals tell him is ‘valuable to the cause’. Dean is baffled. He can’t think of a reason a 15-year-old male hooker could be valuable to them. But Dean accepts the work nevertheless because he doesn’t want to lose the advantages living with the Order gives him. But what happens when the boy, Sam, turns out to be an insufferable brat whose throat Dean can’t wait to slit?

    Language:
    English
    Words:
    35,542
    Chapters:
    11/?
    Collections:
    1
    Comments:
    63
    Kudos:
    379
    Bookmarks:
    46
    Hits:
    6961
  9. Tags
    Summary

    The Winchester Brothers, a pair of honest hardworking brothers who are well-known bakers in the town and loved by everyone there...however, nobody knows they used to be prostitutes.

    (Inspired by Evillious Chronicles: Flower of the Plateau)

    Series
    Language:
    English
    Words:
    380
    Chapters:
    1/1
    Comments:
    3
    Kudos:
    13
    Hits:
    462
  10. Tags
    Summary

    Sam's pretty sure his family will be better off without him.

    Chuck Shurley disagrees.

    Language:
    English
    Words:
    2,889
    Chapters:
    1/1
    Comments:
    1
    Kudos:
    55
    Bookmarks:
    6
    Hits:
    959
  11. Tags
    Summary

    Sam has feelings he can't let go.

    Language:
    English
    Words:
    1,545
    Chapters:
    1/1
    Kudos:
    20
    Hits:
    491
  12. Tags
    Summary

    Dean leaves with Sam. It's the only choice.

    Language:
    English
    Words:
    606
    Chapters:
    1/1
    Kudos:
    27
    Bookmarks:
    1
    Hits:
    538
  13. Tags
    Summary

    It’s late and rainy and he’s finally at a rest stop with six hours to spare, and all Dean wants to do is collapse on a bed that isn’t the one inside the cab of his truck.

    Series
    Language:
    English
    Words:
    1,553
    Chapters:
    1/1
    Collections:
    1
    Comments:
    5
    Kudos:
    105
    Bookmarks:
    6
    Hits:
    2363
  14. Tags
    Summary

    Dean's been turned down by Sam for weeks. He finally figures out why.

    Language:
    English
    Words:
    1,930
    Chapters:
    1/1
    Collections:
    3
    Comments:
    9
    Kudos:
    336
    Bookmarks:
    29
    Hits:
    6481
  15. Tags
    Summary

    “I wanna see them fuck each other,” the bride stage whispered.

    Dean caught the corner of Sam’s eye and winked. He extricated himself from beneath a leopard-print dress, just far enough to lick his lips and purr, “We can do that.”

    Series
    Language:
    English
    Words:
    1,765
    Chapters:
    1/1
    Collections:
    1
    Comments:
    28
    Kudos:
    102
    Bookmarks:
    6
    Hits:
    3214
  16. Tags
    Summary

    15 year old Sam is desperate for his brothers love. Dean craves Sam, but both are too scared to admit it, what happens when Sam runs from his feelings?

    Language:
    English
    Words:
    5,375
    Chapters:
    1/1
    Comments:
    4
    Kudos:
    85
    Bookmarks:
    9
    Hits:
    1993
  17. Tags
    Summary

    There's always someone looking, no matter where hunting takes them. Lonely housewives, horny businessmen. Anyone with enough money and inclination.

    Tonight is a bachelorette's party. Dean helps Sam prepare.

    Language:
    English
    Words:
    2,071
    Chapters:
    1/1
    Comments:
    55
    Kudos:
    168
    Bookmarks:
    17
    Hits:
    2618
  18. Tags
    Summary

    Sam as a tall, toppy prostitute and Cas as his best friend and/or roommate who is hopelessly in love with him

    Language:
    English
    Words:
    129
    Chapters:
    1/1
    Comments:
    3
    Kudos:
    11
    Hits:
    696
  19. Tags
    Summary

    Sam as a tall, toppy prostitute and Cas as his best friend and/or roommate who is hopelessly in love with him.

    Language:
    English
    Words:
    129
    Chapters:
    1/1
    Kudos:
    5
    Hits:
    197
  20. Tags
    Summary

    The money has run out again. Sam does what he has to, just like he always has.

    Language:
    English
    Words:
    1,065
    Chapters:
    2/?
    Comments:
    3
    Kudos:
    27
    Bookmarks:
    1
    Hits:
    630

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