7 Works in Sam Winchester Wears Women's Clothes

Listing Works

  1. Tags
    Summary

    Dean is reminded of how he used to tease Sam about being a girl, only now, he finds it hot.
    (Or, the semi-forced feminization of Sam Winchester.)

    Language:
    English
    Words:
    2,040
    Chapters:
    1/1
    Comments:
    10
    Kudos:
    169
    Bookmarks:
    23
    Hits:
    3,150
  2. Tags
    Summary

    They are taking a break in for hunting after Sam got a spell casted on him to have a vagina and boobs. Sam is attending university and Dean lives with Sam in his dormitory. They are two big sluts who have a lot of fun and kinky stuff up their sleeves. Sam is a complete slut for his older brother and boyfriend.

    Language:
    English
    Words:
    1,802
    Chapters:
    2/?
    Comments:
    1
    Kudos:
    53
    Bookmarks:
    11
    Hits:
    3,203
  3. Tags
    Summary

    Sam loses a bet, but gains a kink.

    Language:
    English
    Words:
    5,426
    Chapters:
    1/1
    Comments:
    6
    Kudos:
    155
    Bookmarks:
    24
    Hits:
    1,549
  4. Tags
    Summary

    “Y-you’re wearing…?” Dean asked and Sam made a soft expression, like he didn’t know what he was talking about. “Panties?” Dean whispered like it was some kind of crime.
    “Do you wanna check?”
    Dean nodded vividly and waited, looking at Sam’s hips, but Sam grabbed his hand once more and put it in his thigh. Dean looked at him, so he just nodded. Dean’s hand slid slowly until it hit his hip, touching the fragile fabric.
    “Lace?” Dean asked, and Sam nodded again. “Doesn’t it… itch?”
    “Yes it does, but I can…” Sam made strength down and moved his hips forward, making the fabric rub his penis. What resulted in him groaning softly. And Dean looked at him like he had been touched too, full of lust.

    Language:
    English
    Words:
    5,086
    Chapters:
    1/1
    Comments:
    4
    Kudos:
    67
    Bookmarks:
    12
    Hits:
    1,804
  5. Tags
    Summary

    Sam feels ridiculous for all of three seconds as he pulls the skirt up his legs.  But then he looks in the mirror and sees the way the too-short pleated skirt makes his long, shaved legs look even longer.  It’s so much effort, but he knows Dean loves calling him his ‘princess’, so as a birthday gift, Sam’s decided to make himself look like one. 

    Series
    Language:
    English
    Words:
    2,276
    Chapters:
    1/1
    Comments:
    1
    Kudos:
    125
    Bookmarks:
    17
    Hits:
    2,395
  6. Tags
    Summary

    Dean has everything he's ever wanted. He's a newly signed forward for the Detroit Red Wings, he's got a house outside of Detroit and most of all, he's got his Omega little brother and mate by his side.

    Sam stands on the precipice of one of the biggest events of his young life. All he needs to do is place at the Figure Skating Nationals and he'll secure himself a spot on the U.S. Winter Olympics team.

    But what will they do when a wrench in the form of a tiny little life growing inside Sam, throws all their plans out of wack? Can Sam and Dean handle not only a pup, but the sudden return of their father into their lives? How will Sam deal with possibly losing his shot at the Olympics?

    Language:
    English
    Words:
    8,603
    Chapters:
    7/?
    Comments:
    4
    Kudos:
    140
    Bookmarks:
    26
    Hits:
    3,889
  7. Tags
    Summary

    Sam is eleven when Mary dies.
    He's thirteen when he tries on one of her dresses for the first time.
    And he's fifteen when Dean shows up to complicate his life.

    'Well, hello there, gorgeous.' Dean smirks and gives Sam a shameless once-over, and Sam hopes he hasn't been staring too much, because that would just be awkward. But then he remembers that he just ran into the kitchen counter and barely avoided smacking his head into a cupboard doing so. It's a miracle he hasn't scared Dean away yet.

    Language:
    English
    Words:
    25,067
    Chapters:
    2/2
    Comments:
    57
    Kudos:
    575
    Bookmarks:
    170
    Hits:
    8,468

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