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I Love Dressing Like A Sissy

Personal Stories, Advice, and Support 249 People

    Mommys Little Girl

    I've been wearing girls clothes since birth. my mother wanted a girl , but sorry I was born a boy . she put me pink girly outfits with lots of lace . as I grew she continued to dress me in the frilliest clothes she could find , and even put me in a private school for girls . we...
    sissyboy1960 sissyboy1960
    46-50
    2 Responses Sep 29, 2010

    Serving A Woman

    I have always had a for strong women. I have a high stress job that I always have to be in control. All I want to do is come home ***** off my man clothes and slip into some silky and lacey clothes. I would love to have a strong women to treat me like a ***** when I get home. Not...
    SissiDatti SissiDatti
    36-40, M
    5 Responses Nov 3, 2011

    I Spent The Afternoon Dressing Up As A Sissy Maid

    As people will have read elsewhere, I am relatively new to this game. But in for a penny... I acquired a sissy maids uniform some time ago, but haven't had much chance to try it out. With the family away I had a good opportunity this afternoon. I fished out my various garments...
    jessicasissymaid jessicasissymaid
    41-45, M
    3 Responses Jul 2, 2010

    It Began Many Years Ago

    When I was but 4 or 5  playing in Mom's shoes and hats and jewelry ... I knew.I guess I've always known who I was despite the outward appearance.Once the female starts taking over, well it's very difficult to stop.Why? Because that's where the psyche wants to go, knows it...
    Josie06 Josie06
    56-60, F
    Oct 30, 2011

    Dressed As A Sissy

    being a sissybitch its such a turn on to dress as a sissy so humiliating but such a turn on especially going out dressed as a sissy!love going to a party dressed as a sissy since i expect to have to such **** swallow ***,lick ******* especially those filled with *** and get...
    mandiejune mandiejune
    51-55, M
    1 Response Jan 14, 2012

    Not A Real Experience, But In My Dreams

    It is one of my fantasies to go to bridal shop end be fitted for a custom evening gown. In my dream sequence, the all Girl Staff would welcome me and They would all want to help me play dress-up. Before i could be measured, They would ***** me, remove all body hair and then...
    redlace redlace
    61-65, M
    Jun 27, 2010

    A Day In Pantyhose

    It has been many years that Jessica has been suppressed. She went away to save a marriage and rid herself of all her femme clothes, pics, mags, make up, wigs, and toys. I cannot say why, but this year she is fighting to come out again. Wife does not approve or encourage, and...
    JESSICAKNIGHT JESSICAKNIGHT
    51-55, T
    Jul 23, 2010
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