1 - 20 of 816 Works in Kinky Dean Winchester

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  1. Tags
    Summary

    Ever since his mother died, Dean Winchester’s world has been one of revenge and violence. His father, a well renowned bounty hunter, made it his personal mission to kill the man responsible. However, now that Sam is 18, he gives Dean a new mission. Protect your brother at college. So now, the 2 brothers take on Stanford.
    Castiel’s family is one of prestige and wealth. But beneath the fanciful exterior lies a secret dark side. Are they basically the mafia? No one is really certain. Known as the “Angel of Death,” Castiel is the best assassin in his family. For the past 3 years, he’s been mostly out of commission, finishing his degree at Stanford, like his father wanted him too. How crazy could his last year get?

    Language:
    English
    Words:
    38,984
    Chapters:
    12/?
    Comments:
    22
    Kudos:
    60
    Bookmarks:
    16
    Hits:
    1,943
  2. Tags
    Summary

    Some monsters don’t chase to kill—they chase to keep what they’ve broken

    "Run, Little demon."

    Series
    Language:
    English
    Words:
    4,854
    Chapters:
    2/2
    Comments:
    3
    Kudos:
    2
    Hits:
    109
  3. Tags
    Summary

    Dean came for the pool tables. He stayed for Cas, the older, tattooed bartender who never flirts but always steps in when Dean gets in over his head. One night, things go too far, and Cas crosses a line of his own. It could break Dean down… or be his lucky break.

    Language:
    English
    Words:
    8,628
    Chapters:
    1/1
    Collections:
    1
    Comments:
    82
    Kudos:
    349
    Bookmarks:
    87
    Hits:
    2,393
  4. Tags
    Summary

    He went willingly into the hands that carved him open, and found comfort in the ruin left behind.

    “You break so pretty.”

    Series
    Language:
    English
    Words:
    3,600
    Chapters:
    1/1
    Kudos:
    13
    Hits:
    231
  5. Tags
    Summary

    New town, new school for Sam. It's his fifth high school in three years but John promises it's going to be Sam' s last one. Dean and Sam settle into their new routine and enjoy being normal. A few months after school starts Sam meets Lexi. He could tell she was trouble the moment he laid eyes on her but it's the kind of trouble he's always wanted. Dean feels the same way about the new waitress at the diner.

    Series
    Language:
    English
    Words:
    138,121
    Chapters:
    45/?
    Comments:
    18
    Kudos:
    67
    Bookmarks:
    4
    Hits:
    3,641
  6. Tags
    Summary

    Dean can suddenly hear Sam’s thoughts after an incident with Crowley. (This is set in season 9 of SPN) Let’s just say he’s not mad about it, snippet:

    “I’ve been doing some research, something to do about secrets? Wanting to reveal a secret of some sort?” he was flipping through the pages of the book.
    “Here, it says break a bond with a dark secret-“
    “Soooo?” Dean drew it out slowly before taking another bigger bite, mayo dripping down his lips.

    God… my jeans are getting tight, you’re killing me Dean.

    Language:
    English
    Words:
    1,347
    Chapters:
    1/1
    Kudos:
    31
    Bookmarks:
    2
    Hits:
    705
  7. Tags
    Summary

    Three weeks ago Dean had his first heat post-Hell which he shared, against the advice of Sam and Bobby, with a certain Angel of the Lord.

    Newly mated, Dean and the rest of 'Team Free Will' (along with the help of Heaven) race against the Demon hordes to stop them from breaking the 66 seals meant to keep Lucifer in the cage.

    The Biblical Apocalypse looms closer with each day that passes and each seal that's broken.

    And if that weren't enough, Angels, Demons, and every other supernatural creature is on the edge of their seat with the news that a Nephilim has come into being. Each side hoping to either kill the abomination or use it to win the war.

     

    Oh, did Dean mention he’s pregnant.

     

    (An Omegaverse Supernatural Rewrite set in Season 4 picking up on "I Know What You Did Last Summer")

    WIP: CURRENTLY IN PROGRESS

    Series
    Language:
    English
    Words:
    16,210
    Chapters:
    2/11
    Comments:
    12
    Kudos:
    84
    Bookmarks:
    19
    Hits:
    1,678
  8. Tags
    Summary

    Cas has a problem with his wings. They need to be groomed. Typically angel’s groom each other’s wings but he’s not welcomed in heaven aymore to ask other angel’s to groom his wings. SO he decided to ask Dean for help. The thing is, angel wings are extremally sensitive. No, they are one huge erogenous zones for angel’s. It ends with Dean testing the theory if he could make Cas finish just by touching his wings.

    Kinktober Day 31 – Writer’s choice – WING KINK

    Series
    Language:
    English
    Words:
    2,372
    Chapters:
    1/1
    Comments:
    1
    Kudos:
    89
    Bookmarks:
    9
    Hits:
    874
  9. Tags
    Summary

    Dean eyed the creature that stood before him, preparing for the monster to lunge at him.

    But this monster only looked at Dean, it's head titled slightly, it's eyes trailed down Dean's body.

    Dean stayed against the wall, eyeing the monster as it crawled over slowly, its nostrils flaring at it smelled the air.

    Dean's headlamp flickered, the monster's eyes shifting in the light. With the little light on the creature, Dean realized the monster looked a lot different. It was still naked, it's body pale and dirty, but it wasn't completely hairless; its hair was thick, matted, and black, long enough to almost cover the tips of it's pointy ears. A spattering of hair trailed along its chest and stomach, trailing down between its legs.

    Dean blushed, realizing this creature was male, his eyes flickering back up to its face. He noticed it had eyebrows, which were down turned, almost as if it was curious about Dean.

    OR

    Dean Winchester is an experienced caver and while down in a cave, he runs into some creatures and one particular creature sparks his interest.

    Language:
    English
    Words:
    34,317
    Chapters:
    3/3
    Comments:
    22
    Kudos:
    47
    Bookmarks:
    12
    Hits:
    885
  10. Tags
    Summary

    You meet Dean Winchester at a bar, and he takes you back to his motel, where you show him who's truly in charge.

    Language:
    English
    Words:
    1,756
    Chapters:
    1/1
    Comments:
    1
    Kudos:
    42
    Bookmarks:
    2
    Hits:
    677
  11. Tags
    Summary

    Dean and you are training when he has an unexpected reaction to you pinning him down. You take it in stride - and Dean gets more than he bargained for.

    Series
    Language:
    English
    Words:
    1,958
    Chapters:
    1/1
    Comments:
    4
    Kudos:
    63
    Bookmarks:
    1
    Hits:
    872
  12. Tags
    Summary

    Dean had been working the bar for a few nights, cheating pool, looking for something to take his time before he had to move on after finishing the job he'd been sent to do.
    However when someone catches his eyes across the bar, he can't help but find a way to spend his night.

    He got a lot more than he signed up for though, because Castiel wasn't just an easy lay, he was everything Dean ever wanted.

    Series
    Language:
    English
    Words:
    4,135
    Chapters:
    1/1
    Comments:
    7
    Kudos:
    119
    Bookmarks:
    14
    Hits:
    1,197
  13. Tags
    Summary

    (Formerly named Submission or Starvation)
    (Name change after song by The Mamas & the Papas)

    Castiel Novak is a priest who essentially hates his life and is riddled with horrendous nightmares.
    One night, to ease the pain, he stumbles to the Chapel and comes across a creature that just might make his restless nights easier, or might just calm his nerves forevermore.

    ・*:.。.

    Dean Winchester is a blood-hungry vampire, roaming the streets, while narrowly avoiding the many police trying to locate who is behind all the strange deaths culminating in Lawrence.
    One night, to ease his hunger, he stumbles into what appears to be a chapel and meets a man looking at him with just as much hunger as he feels in his own rattling bones.

    Language:
    English
    Words:
    16,664
    Chapters:
    8/8
    Comments:
    18
    Kudos:
    58
    Bookmarks:
    14
    Hits:
    1,008
  14. Tags
    Summary

    This is part of a series called "Weird Together," so it's clearly filled with super normal stuff.

    Dean being Cas' adorable pet human, Cas tasting tears for the genetic material they contain, Dean crawling across a meadow, under stars his boyfriend made, for a crumb of dick.

    Nothing weird here!

    (There are, in fact, many weird things here.)

    - This can be read by itself.

    Series
    Language:
    English
    Words:
    5,582
    Chapters:
    1/1
    Collections:
    1
    Comments:
    14
    Kudos:
    73
    Bookmarks:
    7
    Hits:
    908
  15. Tags
    Summary

    Dean has a stalker.

    He doesn't really mind, though.

    Language:
    English
    Words:
    1,292
    Chapters:
    1/1
    Collections:
    1
    Comments:
    10
    Kudos:
    112
    Bookmarks:
    8
    Hits:
    782
  16. Tags
    Summary

    Dean gets pumped full of eggs on a hunt gone wrong… Or does he?

    Series
    Language:
    English
    Words:
    815
    Chapters:
    1/1
    Collections:
    1
    Comments:
    6
    Kudos:
    23
    Hits:
    724
  17. Tags
    Summary

    Castiel only meant to walk his sister down the aisle. He never expected that the best man's take on “something blue” would be his undoing.

    Language:
    English
    Words:
    9,829
    Chapters:
    1/1
    Comments:
    10
    Kudos:
    78
    Bookmarks:
    6
    Hits:
    590
  18. Tags
    Summary

    Dean may or may not have said something stupid and unnecessary.
    He's tried apologising.
    Except Cas won't talk to him now, and Dean's starting to get annoyed at his behavior.

    Cas is done. He's given everything to this man, and still it's not enough. Still he gets treated like he doesn't matter. He can't do it anymore. Can't handle loving from afar. He needs distance.
    Perhaps ghosting Dean was all it ever took.

    Language:
    English
    Words:
    13,617
    Chapters:
    1/1
    Comments:
    6
    Kudos:
    114
    Bookmarks:
    15
    Hits:
    1,581
  19. Tags
    Summary

    “It fits, right?” Dean asks nervously when he feels Cas’s hand slide down the back of his leg overtop the sheer, hot pink fabric. This is his first time wearing stockings, so he wouldn’t know.

    The mattress dips between his legs as Cas crawls on for a moment, and he swoons beneath a kiss being pressed to his temple.

    “Perfectly.”

     

    (TLDR: Sequel to Read-Aloud. Destiel slow and sensually getting Dean all dolled up in an outfit of full lingerie, and then obviously having some fun in it. Adorable, pretty kinky, and very healing. Yay!)

    Series
    Language:
    English
    Words:
    44,470
    Chapters:
    1/1
    Comments:
    14
    Kudos:
    95
    Bookmarks:
    11
    Hits:
    1,856
  20. Tags
    Summary

    Kinktober 2025: Dean and Cas get dirty in the garden

    Chapter 1: orgasm control [first time writing that!], finger sucking, outdoor sex

    Chapter 2: oral sex, come licking, hand cuffs, kneeling, possessiveness, rimming, anal fingering and fisting, coming untouched

    Chapter 3: Watersports, anal fingering, anal fisting, outdoor sex

    Language:
    English
    Words:
    4,143
    Chapters:
    3/3
    Comments:
    4
    Kudos:
    49
    Bookmarks:
    6
    Hits:
    1,608

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