1 - 20 of 32 Works in Crossdressing Dean Winchester

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  1. Tags
    Summary

    This is a place for all my smutty bits and random story pieces. Each chapter is unconnected unless noted. All kinks and pairings will be listed in the chapter titles and here in the summary.

    Chapter 1: Wincest Not!Fic [Pantyhose Kink, Foot Jobs]
    Chapter 2: Scoyd Heacanons [Domestic, Human AU]
    Chapter 3: Ramsay x OFC [Bookstore AU]
    Chapter 4: Wincest Snippet [Bunker Sex, Oral Sex]
    Chapter 5: Sheriff Stilinski has some thoughts about Steter [Internal Monologue]
    Chapter 6: The Winchester Brothers x Two Hellhounds [CRACK, Bestiality, Knotting]
    Chapter 7: Scott McCall x Supernatural Flower [Xenophilia, Sex With A Plant]
    Chapter 8: Vampire!Stiles AU Fic Idea [Steter Potential]
    Chapter 9: Scott x Jackson's First Kiss [Drabble]
    Chapter 10: Khan Noonien Singh x OFC [AU, First Meetings, Neighbors]
    Chapter 11: Robb Stark x Roose Bolton [Modern/Office AU, Unhealthy Relationship]
    Chapter 12: Jonmund [Model/Artist AU, Fragment]
    Chapter 13: Scott x Liam [Human AU, Blowjob, Liam is 18]

    Language:
    English
    Words:
    12,696
    Chapters:
    13/?
    Comments:
    12
    Kudos:
    126
    Bookmarks:
    9
    Hits:
    6603
  2. Tags
    Summary

    On Christmas Eve, freshly-uncloseted Dean is dumped before his first-ever date with another dude. There to lift his spirits is Castiel, a talented mall-kiosk makeup artist with blue hair and a shy smile. But Cas is all that and more: he also happens to do seasonal work for actual, literal Santa.
    Contrary to all plans ever made, Dean is swept away for one spectacular night with Cas and his sleigh-pulling moose, chasing storms, delivering gifts, and talking about Dean’s ideal first time with a guy.
    Okay, cool.
    New plan?
    Date Cas.

    Language:
    English
    Words:
    46,080
    Chapters:
    5/5
    Collections:
    1
    Comments:
    118
    Kudos:
    367
    Bookmarks:
    76
  3. Tags
    Summary

    Castiel enjoys going through Dean's personal belongings, and Dean enjoys letting him. One evening Cas finds a pair of panties in Dean's bag, and assumes the worst: Dean slept with someone else.  
    (Spoilers: He didn't. The panties are Dean's.)

    Language:
    English
    Words:
    5,232
    Chapters:
    1/1
    Comments:
    44
    Kudos:
    715
    Bookmarks:
    80
  4. Tags
    Summary

    Dean and Sam are kidnapped by a giant as gifts for his daughters. Sam want to escape immediately and keeps insisting to Dean to call Castiel while Dean wants to stay for a little bit (his chance to see some gigantic naked girls as much as he could since their cage is in their bedroom). Now the brothers are dealing with humiliating situations that normal pets go through in the hands of affectionate humongous girls.

    Language:
    English
    Words:
    1,262
    Chapters:
    2/?
    Comments:
    15
    Kudos:
    36
    Bookmarks:
    4
    Hits:
    1143
  5. Tags
    Summary

    "Castiel watched his footsteps as he walked down the street toward Dean’s house. It had been a few weeks since they had last had time for him to come over, and they both craved time for just the two of them.

    He quietly walked down the hardwood hallway, hoping that he would be able to catch Dean dancing if he wasn’t heard. The door was cracked open, a small amount of the natural light spilling into the darkened hallway. While he did end up catching him dancing, what he also saw surprised him. Dean was wearing a powder pink, sleeveless dress."

     

    Dean finally has the house to himself and forgets that he invited Castiel over for the afternoon. What happens when Cas walks in on him wearing a dress and makeup?

    Language:
    English
    Words:
    3,343
    Chapters:
    2/2
    Comments:
    4
    Kudos:
    111
    Bookmarks:
    8
    Hits:
    1364
  6. Tags
    Summary

    Castiel doesn’t do one-night stands. Once he hit forty, he figured his time was up, his life had pretty much come to a halt, and there was nobody out there for him. He lives in a cute little village, riding his bicycle between his vet clinic and his cottage; that’s his world, and he’s given up on expanding it. But in one last, desperate attempt to find someone, he contacts Rowena, the local witch, and asks her to summon his soulmate. Rowena brings a storm. The storm washes up a trio of ducklings, huddled for shelter inside the rainboots of the new-to-town kindergarten teacher (and retired motorcycle daredevil), Dean Winchester. Ducklings in hand, Dean seeks out Castiel’s veterinary expertise. Somehow, in a flustered, spontaneous burst of attraction, they spend the night together. And just like that, Castiel’s life starts again. With every passing week they become better friends, sharing deeper intimacies, caring for their duck babies as well as each other. But staying together requires taking risks which neither of them planned for. Dean’s risk puts him in extreme physical jeopardy. And Cas? He has to overcome fifteen years of emotional hurt, just to follow where Dean leads.

    Language:
    English
    Words:
    92,927
    Chapters:
    18/18
    Collections:
    3
    Comments:
    398
    Kudos:
    1044
    Bookmarks:
    258
  7. Tags
    Summary

    The bullets hit my chest, tingling a bit. I automatically overplay my reaction a touch to pull off the trickster guise, flinching a little and taking a moment to recover.
    “Ouch,” I tease, “but, y’know? I think it takes a stake dipped in the blood of one of my many victims to bring me down. Have any of those lying around? Didn’t think so.”
    He shoots me in the face.
    I groan. “Seriously? You had to pick the face, didn’t you?”

    Language:
    English
    Words:
    8,309
    Chapters:
    3/?
    Comments:
    1
    Kudos:
    58
    Bookmarks:
    9
    Hits:
    666
  8. Tags
    Summary

    It starts with a hairpin.

    Or,

    The one where Cas notices something seemingly trivial, which leads to an embarrassed Dean eventually divulging his biggest secret, much to both of their delights.

    Series
    Language:
    English
    Words:
    12,009
    Chapters:
    2/2
    Collections:
    1
    Comments:
    66
    Kudos:
    430
    Bookmarks:
    64
    Hits:
    6693
  9. Tags
    Summary

    “YES I KNOW I KNOW! Our armors are skimpy! Could you boys just dropped it and focus on HELPING US BRING THAT DEMON DOWN AND SAVE MY GIRLFRIEND!!!”
    ------------------
    Legends of powerful demonic sentient armor suits called Kamui that will give the wearers invincible strength and swift speed at the price of their blood for every use...and their dignity.

    The Winchester brothers find out that the demon armors are in the hands of two daughters of a pair of skilled wealthy hunters who are well-known for being almost naked when they killed so many monsters.

    Ryuko want to avenge her father while Satsuki want to take her mother’s power but they team up since both of them want their mother dead.

    When the sisters are forced to hide Senketsu and Junketsu, Sam and Dean are forced by the Kamui to wear them so that they can find their original wearers.

    Language:
    English
    Words:
    287
    Chapters:
    1/?
    Kudos:
    11
    Bookmarks:
    2
    Hits:
    286
  10. Tags
    Summary

    Cas and Jimmy's car breaks down one night and they meet a very interesting character....

    (Cross posting from tumblr)

    Language:
    English
    Words:
    249
    Chapters:
    1/1
    Comments:
    7
    Kudos:
    21
    Bookmarks:
    1
    Hits:
    383
  11. Tags
    Summary

    Dean wears his special Cheer uniform to meet his boyfriends after class.

    Language:
    English
    Words:
    2,493
    Chapters:
    1/1
    Comments:
    3
    Kudos:
    247
    Bookmarks:
    31
    Hits:
    5796
  12. Tags
    Summary

    This is not the retelling of "The Wizard of Oz" you wanted, neither is it the retelling you needed, but it doesn't change the fact that Castiel is dying and Dean is wearing a dress, and there are mercifully fewer zombies than originally planned.

    Series
    Language:
    English
    Words:
    2,848
    Chapters:
    1/1
    Collections:
    1
    Comments:
    15
    Kudos:
    9
    Bookmarks:
    1
    Hits:
    237
  13. Tags
    Summary

    Castiel is a bad influence on Dean. Okay, they’re only six years old – but when they join forces, they’re Mary Winchester’s idea of a parenting nightmare. In theory, Dean and Cas live in hotel rooms opposite each other. But in actuality, Castiel lives with Dean. Shares his clothes, his food, his bed. That sort of thing. Dean might like the colour pink more than society says he should, and Cas has the same problem with petty crime, but there’s one attribute they have in common: neither take well to being apart.

    Language:
    English
    Words:
    29,069
    Chapters:
    1/1
    Collections:
    1
    Comments:
    108
    Kudos:
    1180
    Bookmarks:
    232
  14. Tags
    Summary

    It’s Castiel’s favorite part of these nights, seeing him in low cut dresses, fringe framing his thighs, imagining that one day Castiel will get to touch all that pale, freckled skin.

    Language:
    English
    Words:
    6,032
    Chapters:
    1/1
    Collections:
    1
    Comments:
    11
    Kudos:
    148
    Bookmarks:
    23
    Hits:
    2437
  15. Tags
    Summary

    While waiting on all of these fics I am reading to be updated (and updating my own), I have taken it upon myself to draw out scenes / other things that stick out to me. These are the drawings from 'Smoky Kisses', by: Setaeru.

    Series
    Language:
    English
    Words:
    0
    Chapters:
    1/1
    Comments:
    17
    Kudos:
    31
    Bookmarks:
    3
    Hits:
    1518
  16. Tags
    Summary

    They left town the day after and Dean never knew how to feel about that librarian.

    Then or ten years later, Dean didn’t know if it had been a horrible molestation that led him down the path of depravity to self-medicate or if it had been a glorious awakening that let him become who he really was.

    It depended on the day mostly.

    Series
    Language:
    English
    Words:
    26,049
    Chapters:
    1/1
    Collections:
    1
    Comments:
    171
    Kudos:
    2381
    Bookmarks:
    495
    Hits:
    127944
  17. Tags
    Summary

    Dean wanted to be deanna for a night and what better opportunity than a Halloween party.

    Language:
    English
    Words:
    2,223
    Chapters:
    1/1
    Kudos:
    52
    Bookmarks:
    2
    Hits:
    2066
  18. Tags
    Summary

    This high-steppin' 1930's comedy has the Winchesters dodging insults, bullets, and insinuations of homosexuality, without ever missing a chance to dance and sing like vaudevillian darlings.
    Sam Winchester is about to make it to the big time as a velvet-voiced singer. Dean is the ever-supportive older brother with a few mostly harmless secrets hanging in his closet. But there's danger afoot that can only be foiled with the help of a wry PI and his mute cousin, Gabriel.
    All that, plus hot dames who know their weapons!

    Language:
    English
    Words:
    36,917
    Chapters:
    13/13
    Comments:
    44
    Kudos:
    41
    Bookmarks:
    12
    Hits:
    1129
  19. Tags
    Summary

    Dean was standing in the kitchen looking through the window, watching his small family playing some sort of game, where Gabe was pretending to eat the kids and Cas was just standing there listening to Sam and Jess ramble about something. When suddenly their eyes met and his breath hitched just like the first time he had laid eyes upon the beautiful creature that was now his husband, he smiled to him, took the snacks, arranged his dress and went to the garden where he would wait for the rest of his family to arrive. After all it was the annual Novak-Winchester (Singer-Harvelle, etc.) barbecue. It all had started with a hunt.
    It was 12 years ago when this story began.

    Language:
    English
    Words:
    3,481
    Chapters:
    2/?
    Comments:
    7
    Kudos:
    46
    Bookmarks:
    7
    Hits:
    1577
  20. Tags
    Summary

    Castiel wanted to be useful, so Castiel decided to do the laundry. He ends up finding more than he expected.

    Series
    Language:
    English
    Words:
    6,462
    Chapters:
    2/2
    Comments:
    9
    Kudos:
    216
    Bookmarks:
    24
    Hits:
    2890

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