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I Love to Walk the Streets Around My House As a Cross Dresser

Personal Stories, Advice, and Support 213 People

    Done This

    i have done this too many times to count. the most intresting storys was when i was stopped by law enforcement. if you want to  know more please just ask :D
    sissygurlmaidannabelle sissygurlmaidannabelle
    36-40, T
    Dec 23, 2009

    My First Time.

    I remember when I first went outside dressed.  It was after my mom found out that I was into crossdressing.  She wanted me to drop the mail off in the mail box down at the end of the block.  I told her that I had already taken the mail down but I lied as I wanted...
    silkiehosewearer silkiehosewearer
    31-35, M
    2 Responses Jun 26, 2009


     A few years back, I had my first experience of walking the streets near where I lived, dressed in a rather short little black number, black tights and high heeled shoes. I took quite a lot of care to make sure my clothes and make-up were OK - not TOO tarty, but I...
    clairemeredith clairemeredith
    46-50, T
    6 Responses Aug 22, 2009

    My First Time Outside...

    was when I was about 14 wearing my mothers clothes and heels.I remember that night very well, like it was last night.It was a Thursday night and my mother was working back late the the shop she worked at. A woman's shoe shop btw. I was in heaven because she got some very...
    RobynTheBeautiful RobynTheBeautiful
    10 Responses Jan 18, 2010

    A Fun Night

    When I was about 11, my parents and siblings were away, leaving me home alone.  A friend who shared my cross-dressing interests came over and, after dark, we dressed fully as females (putting scarves on our heads to both hide out identities and because we had short hair...
    TBurke99 TBurke99
    51-55, M
    4 Responses Jul 21, 2009

    Often Misinderstood...

    EP has given me the opportnity the last few months to find out more about myself. In particular why I am how I am, why I like what I like, and if I am truly happy. There are many misconceptions associated with some terms/labels used for people like me. I have done a lot of...
    garterbeltgirl19 garterbeltgirl19
    36-40, M
    Sep 22, 2011

    Late Night

    i'd been to the pub near to where i live, iyt was quite breezy as i was walking home, about midnight, anyway my thoughts turned to feeling what it would feel like if i sliopped on my favourite dress when i got home. well i got home, got undresed and put a bra and nix on put some...
    manda1 manda1
    56-60, M
    3 Responses Nov 14, 2010

    My Friend and I

    After a while when my friend and I who both loved to crossdress and loved to wear pantyhose.   Decided to walk around outside dressed up.  As we only dressed around each other a few times and I dressed up around my girlfriend off and on.  My friend was staying...
    sexyblackpantyhose sexyblackpantyhose
    31-35, M
    1 Response Aug 2, 2009

    Walking Around My Neiborhood

    I love to dress up in my mini skirt and nice top and take a walk around my neiborhood. Some times I'll walk down to the school and just find a nice place to sit and enjoy the sun.
    krystals krystals
    46-50, T
    2 Responses Jul 21, 2009

    Outside Dressed

    I have been crossdressing for many years. I love wearing my french maid’s outfit while I do house work. My wife enjoys seeing me working around the house in my maids outfit or my panties. I have even mowed the lawn while wearing panties while my wife is watering the garden in...
    pantiescouple pantiescouple
    Jul 19, 2010

    Forced to Walk Home

    My Mistress forced me to walk home from her place to my home dressed. It was so hot walking home in high heels and short dress and hoping no car would stop to laugh or pick me up!!Once i got home i had to phone my Mistress up and tell her how i had enjoyed the experience!!!
    mandiejune mandiejune
    51-55, M
    1 Response Aug 14, 2009

    "I Would Love to Walk the Streets Around My House As a Cross Dresser"

    Like I say, Darlings, I would LOVE to walk around the streets ANYWHERE dressed in my favourite outfit, but so far I have never had that opportunity. Actually, I'm not so sure that I would have the guts to do it yet. I'm sure it's an absolute thrill that I can't wait to...
    01Chrissie 01Chrissie
    41-45, T
    2 Responses Sep 24, 2009

    Walking While Dressed

    Love to walk around my neighbourhood dressed en femme - always gives me a thrill no matter how many times I do it :-)
    princessnatasha73 princessnatasha73
    31-35, F
    Sep 29, 2009

    Would Love to

    It would be more accurate to say "I would love to walk ... "   I do wear a skirt to go running sometimes, but I usually wear shorts for the first couple of blocks because I'm too scared for my actual neghbors to see me.
    SomeguyinUT SomeguyinUT
    Oct 1, 2009
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