I Want To Walk Down The Street In A Dress

Personal Stories, Advice, and Support 354 People

    Out And About In Dresses And Skirts

    I love going out for walks in a dress or a skirt. It feels so freeing to be who and what I am outside the confines of my apartment. I can't count the number of times I've been honked and whistled at! I've walked up the street from my apartment to the drug store, walked in and...
    CDLynn CDLynn
    46-50, T
    2 Responses Apr 1, 2013

    Man In Skirt

    At Dennys last night I was surprised when a man walked in wearing what I first thought was a kilt.  Then I realized it was a man's skirt.  It was khaki with two large button down flap pockets on each thigh.  He also had a purse, large soft leather black bag slung over his...
    maculotteb maculotteb
    3 Responses May 26, 2012

    I have dressed and gone out secretly mostly at

    night, it would be so great to be accepted completely by everyone in society and at all businesses and work places to dress and walk on the streets all the time
    alexiswcd alexiswcd
    56-60, T
    1 Response Dec 20, 2015

    I Have Walked Down The Street Wearing A Dress

    I had gone to the Inn at Essex all dressed up in a long flowing black dress, heels, black slip, girdle with stockings, and bra with breast forms. Over the dress I wore a soft 3/4 length jacket.  I wore my ladies watch, bangles and long necklace.  I had a black bag to match my...
    jml2000 jml2000
    61-65, M
    Sep 14, 2012

    Looking Forward To The Adventure..

    To someone that hasn't braved enough courage to step outside, walking down the street sounds like an incredible liberation! I keep thinking about it, and inching closer and closer but struggle getting past the door. Last week my wife was out of town for an evening and spent all...
    Jaclyn9 Jaclyn9
    36-40, T
    8 Responses May 21, 2012

    I Can't See It Differently

    I have come to realise in all my progressive wearing of feminine things, that once you do it, love it, repeat it, you can no longer see it as others do. When I see myself in the mirror "all dressed up and nowhere to go" I think I look normal and lovely! It's hard to imagine...
    Fullcircle Fullcircle
    51-55, F
    5 Responses Jan 15, 2011

    I Have...

    walked around a few streets in a dress in the 'tolerant' part of my local city all done up sexy and showing lots of leg and totaly made up with makeup.Wow.I still cannot believe I did that.
    RobynTheBeautiful RobynTheBeautiful
    5 Responses Mar 10, 2011

    Just Had To Get Out

    This summer has been hot, humid & quite rainy...conditions which lead me to "dress down" for comfort's sake. Recently, though, I was just about to explode with a need to be gurly & go out. Fortunately, I live near a fairly well known medium size city which attracts many tourists...
    janusatv janusatv
    61-65, T
    1 Response Jul 29, 2013

    Reader, I Did It!

    Having DECIDED to do this some while ago I eventually had an opportunity. I have recently had occasional study days in London away from any family. I bought some leggings, as shaving my legs was not really an option. I knew I was going to do it, I knew I was going to look silly...
    purecotton purecotton
    51-55, M
    2 Responses Jan 10, 2011
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