1 - 20 of 79 Works in Sassy Dean Winchester

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  1. Tags
    Summary

    After falling in love as master/slave in a slave trading compound - and two years apart after Castiel set Dean free - Dean Winchester finally gives in. He finds himself in Seattle, looking at the man he can't stop loving no matter how hard he's tried.

    Will they be able to manage a happily ever after?

    Or will their pasts come back to ruin it all?

     

    ** picks up directly after Light in the Dark Epilogue**

    Series
    Language:
    English
    Words:
    48,014
    Chapters:
    12/?
    Comments:
    432
    Kudos:
    420
    Bookmarks:
    69
    Hits:
    12563
  2. Tags
    Summary

    A drunk night spent striking out on Tindr and Grindr lead Dean to fill out a questionnaire for a "unique matchmaker".

    Language:
    English
    Words:
    6,723
    Chapters:
    3/?
    Comments:
    6
    Kudos:
    28
    Bookmarks:
    8
    Hits:
    525
  3. Tags
    Summary

    Caught between the lesser of two evils, omega Dean Winchester is thrown into the orbit of Castiel Novak—a gorgeous, older, and incredibly wealthy businessman…and perhaps the only alpha who wants him for his brains, not his body. Castiel has no interest in bending Dean over the nearest surface and fucking his brains out, which is a first. Not that Dean cares about the alpha’s lack of interest. Nope. Uh-uh. He couldn’t care less.

    Language:
    English
    Words:
    165,202
    Chapters:
    22/22
    Comments:
    2171
    Kudos:
    1576
    Bookmarks:
    324
    Hits:
    40786
  4. Tags
    Summary

    You’re unlucky in love when you find a lost wallet outside a bar and are smitten with the photo on the ID inside. Could your luck have turned, or have you found yourself in the middle of something unfortunate?

    Series
    Language:
    English
    Words:
    9,868
    Chapters:
    5/?
    Comments:
    2
    Kudos:
    8
    Bookmarks:
    3
    Hits:
    132
  5. Tags
    Summary

    "You can have all of this, Winchester," Castiel rasps, voice breathless with arousal, as he leans back on the table, stretching his torso, and crooking a finger at Dean, "-and if you want it," He continues, and with a dark, hungry glint in his eyes, spreads his legs wide apart, "-come and get it."
    ~•~
    teacher's-pet!castiel × jock!dean.

    Language:
    English
    Words:
    5,221
    Chapters:
    1/1
    Comments:
    16
    Kudos:
    206
    Bookmarks:
    19
    Hits:
    1562
  6. Tags
    Summary

    Castiel helps Dean with a migraine even though he didn't ask him to.

    "Dean's curses ceased as he looked up from his pillow with squinted eyes before asking, "What're you doin'?"

    Castiel shrugged [...] before mumbling hopefully, "Helping?""

    Series
    Language:
    English
    Words:
    1,330
    Chapters:
    1/1
    Kudos:
    14
    Hits:
    144
  7. Tags
    Summary

    Sam is watching TV in the motel room when Dean decides that his choice of channel is not at all acceptable. And so, he fights to get his hands on the remote control and an argument quickly ensues - along with a whole lot more. But will Dean get his way?

    Language:
    English
    Words:
    3,063
    Chapters:
    1/1
    Comments:
    4
    Kudos:
    88
    Bookmarks:
    13
    Hits:
    1666
  8. Tags
    Summary

    Dean is a proud Mama's Boy.

    His classmates try to shame him.

    It doesn't go well for them.

    Series
    Language:
    English
    Words:
    1,441
    Chapters:
    1/1
    Collections:
    1
    Comments:
    24
    Kudos:
    421
    Bookmarks:
    22
    Hits:
    2373
  9. Tags
    Summary

    Castiel always notices the same guy in designer suits come into the Walmart where he works as a cashier, but he only comes in after midnight. Dean leaves his phone behind one night, Castiel sees the nude pictures he has because he is one nosy boy. That's where it begins.

    Language:
    English
    Words:
    23,357
    Chapters:
    11/11
    Comments:
    37
    Kudos:
    242
    Bookmarks:
    38
    Hits:
    8012
  10. Tags
    Summary

    A young laboratory technician, Dean Winchester, accidentally opens a portal to another universe and is captured by two of the most feared dragons in all the land.

    Language:
    English
    Words:
    6,634
    Chapters:
    3/?
    Comments:
    3
    Kudos:
    44
    Bookmarks:
    10
    Hits:
    768
  11. Tags
    Summary

    Castiel Novak has been running the Novak Slave Trade for over a decade. He's powerful, respected, and ruthless. When training a slave, he's cold, detached, and uncaring. He's the best trainer there is - as he should be, considering his father started teaching Castiel the business as soon as Castiel could walk. In fact, Castiel quit training slaves years ago. It got dull. He'll never take a slave of his own. He's content where he is. His life has routine.

    But what will happen when a new slave comes into Castiel's slave compound that's wild and sassy and impossible for any of Castiel's highly skilled trainers to break? Will Castiel be able to mold Dean Winchester into the perfect slave? Or will Dean Winchester finally be the one to teach Castiel what love is?

    Who will break first?

    THANK YOU to my lovely main beta reader Chelsy, as well as Maddy!

    ***Disclaimer: this is NOT a BDSM relationship, it is MASTER AND SLAVE from an illegal slave trading perspective. Don’t expect healthy things like aftercare/safe words (though they will come into play later). Castiel is not a complete sadist, but he’s not a very great guy, especially at the beginning. This story does have a happy ending!

    Series
    Language:
    English
    Words:
    112,914
    Chapters:
    35/35
    Comments:
    1593
    Kudos:
    1433
    Bookmarks:
    248
    Hits:
    42161
  12. Tags
    Summary

    As requested on Tumblr: a beach day fic!

    A fluffy, beach vacation one-shot with Team Free Will

    Language:
    English
    Words:
    1,505
    Chapters:
    1/1
    Comments:
    2
    Kudos:
    22
    Bookmarks:
    1
    Hits:
    323
  13. Tags
    Summary

    From my kink/bdsm ABCs event I did on my Patreon. Figured since this one goes with a work on here, I'll break a rule and post it for you all (;

    Enjoy some Orgasm Control <3

    Series
    Language:
    English
    Words:
    2,038
    Chapters:
    1/1
    Comments:
    16
    Kudos:
    153
    Bookmarks:
    8
    Hits:
    2760
  14. Tags
    Summary

    as expected, i failed.

    Language:
    English
    Words:
    6,578
    Chapters:
    11/32
    Collections:
    1
    Comments:
    3
    Kudos:
    48
    Bookmarks:
    1
    Hits:
    748
  15. Tags
    Summary

    (Y/n) is trying to patch Dean up.

    Series
    Language:
    English
    Words:
    437
    Chapters:
    1/1
    Kudos:
    35
    Bookmarks:
    2
    Hits:
    681
  16. Tags
    Summary

    Castiel simply cares for Dean's health and one certainly shouldn't take aspirin with beer.
    ---
    Pre-Slash/Implied relationship if you squint really hard

    Language:
    English
    Words:
    819
    Chapters:
    1/1
    Kudos:
    26
    Bookmarks:
    1
    Hits:
    441
  17. Tags
    Summary

    Dean and Cas finally decide to take a vacation together, away from monsters and saving-the-world-duties. Thirty days together in a cabin, they've earned it.

     Destiel 30 Day OTP Challenge, april 2019.

    The drabbles will be between 500 and 1000 words. I will change the warnings if/when needed. Warnings will also appear before each drabble. Enjoy! This work will be a series but some drabbles will be read as stand alones.

    1. A selfie together
    2. Sharing a milkshake
    3. Grumpy morning heads
    4. Picknicking
    5. Bake together
    6. Ice skating
    7. Wedding day
    8. Building an IKEA-cabinet
    9. Under an umbrella
    10. 1950's version of them
    11. Silly snapchat photo
    12. Ballroom dancing
    13. Lazy Sunday morning
    14. Princess and knight
    15. Movie night
    16. Clothes swap!
    17. First kiss
    18. Something sad
    19. Gaming together
    20. Pocky game
    21. They fight/argue
    22. Water fight
    23. Playing Twister
    24. Something NSFW
    25. Stargazing
    26. Ugly sweaters
    27. Romantic movie kiss
    28. Death
    29. Karaoke night
    30. DO WHAT YOU WANT

    Language:
    English
    Words:
    28,440
    Chapters:
    30/30
    Collections:
    1
    Comments:
    97
    Kudos:
    102
    Bookmarks:
    20
    Hits:
    2200
  18. Tags
    Summary

    Sam and Dean have been Omega's in hiding for most of their lives. Pretending to be Beta's hasn't been easy but at least they have each other. Everything changes with an unexpected heat and a new blue eyed Alpha comes into their lives whether they like it or not.

    Language:
    English
    Words:
    9,091
    Chapters:
    3/?
    Comments:
    46
    Kudos:
    142
    Bookmarks:
    39
    Hits:
    3582
  19. Tags
    Summary

    “So Dean, why exactly were you digging up a grave?”  

    Dean shifts, leaning forward to give Castiel a smile that’s undoubtedly charming. “Would you believe me if I said it was to save someone's life?

    “Not even a little bit,” Castiel says, smiling in return.

    Series
    Language:
    English
    Words:
    13,336
    Chapters:
    3/3
    Comments:
    59
    Kudos:
    371
    Bookmarks:
    44
    Hits:
    3582
  20. Tags
    Summary

    Sam is an overworked Alpha as the young new lawyer at his law firm. The last person he expects to see while working a case is his Omega brother Dean. Forced together they will have to deal with their unresolved feelings for one and another. Can Sam come to terms with what his big brother really means to him? and can he make his stubborn kind frustrating brother see the truth as well? That they were made for each other?

    Language:
    English
    Words:
    5,829
    Chapters:
    3/3
    Comments:
    62
    Kudos:
    318
    Bookmarks:
    49
    Hits:
    4647

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