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I Was Caught Outside Dressed As A Girl By Boys

Personal Stories, Advice, and Support 158 People

    A Walk In The Park

    It was one of those warm summer nights with a full moon that made it as bright as day. I couldn't sleep so I snuck out to the garage where I hid my female clothing and found a short skirt with a white lace blouse to put on. A real female would have gone bare legged but I couldn...
    amandatrane amandatrane
    1 Response Feb 14, 2012

    I Plan On It

    IU think it would be so hot to get caught dresses as a girl by anyone. As long as I don't know them, can get the thrill, and then escape back to my "normal life"
    deleted deleted
    1 Response Jan 16, 2012

    I was about seventeen at the time.

    Small and short for a guy my age but that made it easier to blend in as a girl when I was dressed. ( I was only about 128 pounds and had a 28" waistline with shoulder length brunette hair I could style femininely.) I managed to get dressed and do my make up and nails in the...
    amandatrane1 amandatrane1
    51-55, T
    Dec 13, 2015

    The Power Of The Petticoat

    He, our Harry had a very inquisitive mind from being a small child wanting to know how thing’s worked and why, what effect things would have on him like mud, salt, pepper, water, sand and oil. As he got older things developed into being interactive with cats, dogs and horses...
    Jeanettestudent Jeanettestudent
    56-60, T
    Jul 31, 2012

    When I was about 14 living in the country I had

    a friend that new all about my secret. Anyway my parents were away and I was ment to be at home with my older sisters but swing as I had a friend over they left us to our own devises and went off to another friends house. Anyway my friend and I used to love dressing up and...
    SophieSeal SophieSeal
    26-30, T
    2 Responses Sep 2, 2014

    The Victorian Dress

      My Wife’s a teacher, in a Junior School top grade, 11year old’s, it was their end of term outing/jolly to a stately home that would entertain them to a Victorian Day i.e.  School, Church and Play, to learn first hand what it was like in Victorian times. All the...
    Jeanettestudent Jeanettestudent
    56-60, T
    1 Response Feb 7, 2012

    In Galaxy Far Far Away

    The firsr time i was caught dressed up by boys was a very long time ago. It was at the time i was 14. My parents used to go out on a thursday night and as my sister was away at uni i would have the run of the house to myself. As soon as my parents went out if not before i would...
    louisetv louisetv
    1 Response Jun 24, 2013

    Caught Punished Humiliated

    My wife enjoys humiliating me and I have had lots of public humiliation over the years a regular one on a dark winter night is we go out for a drive I am dressed under a loose sweatshirt and training bottoms in a nearby car park I get my outer clothes ******** off to make it less...
    rachelusissy rachelusissy
    31-35, M
    Jun 29, 2013
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