I Take A Trip Wearing Only Dresses And Skirts

Personal Stories, Advice, and Support 221 People

    Because I Was Living A Transitioning Life

    It was necessary, that I start living and going about my normal life in dresses and appearing female. One of the biggest things that I did was to go and visit an internet buddy in Alaska (I lived on the east coast). Because this friend only new me as the woman (she did know that...
    JoanieNewHampshire JoanieNewHampshire
    61-65, T
    16 Responses Jun 10, 2011

    Trips Wearing Dresses And Skirts

    Uswually my trips wearing a dress are local within a few towns of where I live.  Dressing and going out shopping or to dinner is so much fun. Years ago I would drive from northern New England to the Boston area but wore womwn's jeans and a girlie top.  No one really looked as...
    jml2000 jml2000
    61-65, M
    Nov 9, 2012

    Sorry Girls I Lived It

    It is true I live and passed for a woman many years. I hate myself for not staying that way but I freak out when I get too emotional. it was for that reason I stopped. I know who I am but my family wanted nothing to do with me. But I still loved them and I really could not stand...
    solarregeneration solarregeneration
    41-45, T
    Jul 22, 2010

    Taking A Trip With Donna!!!

    Donna has been out on several trips. some were local, some were long drives, both were very exhilarating for her. Shortly after I moved to my present location. I spent the morning getting ready to go shopping at the local Goodwill store. I had checked it out before dressed in...
    davis36a davis36a
    61-65
    Nov 15, 2011

    Small Trips

     Mostly I just take small trips around the city.  To go shopping and the like.  The best trip however was to Virginia.  I drove from my city to just outside of Washington, D.C. to visit my brother.   He wasn't at all pleased with my appearance, but...
    bobbie13 bobbie13
    56-60, T
    2 Responses Aug 14, 2010

    Back Out!

    A couple of weeks ago my wife and I escaped to our country cottage in Wales. Due to my job, we live "over the shop" so to speak and it is is impossible to be seen around the parish dressed as a woman. Our short break began with my wife giving me a leather dress for my birthday...
    wetrev wetrev
    46-50, M
    Feb 15, 2012

    At @ 20 yo I needed to gain confidence

    when dressed. I had been dressing for 6 or 7 years and had an older gay BF who I'd revealed my desire to crossdress to by dressing for him the second time we met. I'd been out dressed with him to go shopping, meet some of his friends, even served as a French maid at some of his...
    amandatrane1 amandatrane1
    51-55, T
    1 Response Nov 15, 2015

    Back Out!

    A couple of weeks ago my wife and I escaped to our country cottage in Wales. Due to my job, we live "over the shop" so to speak and it is is impossible to be seen around the parish dressed as a woman. Our short break began with my wife giving me a leather dress for my birthday...
    wetrev wetrev
    46-50, M
    1 Response Feb 15, 2012

    It's A Regular Thing

    Taking a trip as AnneMarie is a regular thing for me. I don't think I could bear to lose these trips. I always go to see my therapist en femme. It's a 150 mile drive, I always stay overnight in a family run hotel where I am always welcome as a lady guest. It's a fantastic...
    RoseViolet RoseViolet
    46-50, F
    Jul 31, 2010
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