I Want To Be Able To Go Outside Dressed As A Woman

Personal Stories, Advice, and Support 312 People

    TinyDickJohn TinyDickJohn
    41-45, M
    3 Responses Nov 23, 2015

    Haven't Done It In A While

    But I have gone to a convenience store in a blue skirt, white top, nylons and heels while out of town on business. It was exhilarating and wonderful. Sitting around my hotel room in a shirtdress and heels, then visiting the lobby for a paper and snacks or coffee. In a far away...
    Josie06 Josie06
    56-60, F
    2 Responses Aug 20, 2010

    I have a trip coming up

    where I will be driving about 4 hours. I am thinking of dressing up for the drive. I have a really short mini skirt, pink camisole, and 5" wedge sandals. Of course I will wear panties (probably a thong) and a stuffed bra. My bra straps will be showing. It will not look elegant...
    submike1234 submike1234
    41-45, M
    2 Responses Oct 2, 2015

    I want to out side in the sun

    and tomorrow I am. Gay Pride Day! At least I. My town we're having a Parade and music. I'm going to dress in a Jean mini skirt. My nails and toes are painted, wig and make up. Oh. And comfy shoes. What else is a surfergurll need to ! Time to celebrate our perfection of...
    sissysurfer sissysurfer
    66-70, T
    1 Response Oct 9, 2015

    I am planning another outing.

    I am planning to wear a pink camisole, black bra where the straps will show, a black skirt that goes to mid thigh, and boots with 3 inch heels that go up mid calf. I am going to a mall about 15 miles from my house. It is a suburban outdoor mall, so I can walk around quite a...
    submike1234 submike1234
    41-45, M
    Mar 29, 2016

    I previously wrote that I have a trip coming up

    that requires a 4 hour drive and I was thinking of dressing up for it. The drive is still a couple of weeks away. I have thought a lot about this recently. I was originally planning to wear a very short skirt, pink camisole, 5” wedge sandals, with a bra and panties. One...
    submike1234 submike1234
    41-45, M
    Oct 19, 2015

    Last Night

    Last night, I was a little more bold than ever.I ventured to one of the local RedBox sites. It's one that is outside one of the local Walgreen's stores. It also happens to be facing one of the towns main streets.Granted it was about 1 a.m., it was bolder than usual for me. From a...
    JosetteLaRoc JosetteLaRoc
    Feb 15, 2013

    Unfulfilled Dreams...

    Well, I go out dressed as a woman regularly, but its still not that way that I want. Going out in jeans or female pants wearing a sweater or t-shirt or a blouse its not fulfill my desires. Even if I wear a high heel, still not, okay its rising the bet, and the thrill and joy is...
    VivienXX VivienXX
    26-30, T
    May 13, 2011

    Take It Gradually

    Hi, folks, yes, don't we all ! I have just come inside from weeding my 1/4 acre section that really needed it. Hard work, but I felt soo nice, wearing a new pair of women's black shorts, and a W.  T shirt that is somehow cut a little different from mens. And a little...
    Moddle Moddle
    70+, M
    Nov 7, 2009

    I Want To Be Able To Go Outside Dressed As A Woman

    And I have gone outside dressed as a woman. It's so much fun dressing up as a woman and leaving the house. And driving off to run errands wearing a dress and heels. The feel of a girdle tugging on my nylon stockings. The feel of my slip over my nylon covered legs. The air...
    jml2000 jml2000
    61-65, M
    2 Responses Jun 9, 2013

    In The Shadows For Now

    My wife accepts that I dress; so long as I keep it in the house (apt).She's away for the weekend. So, early this morning, I took the opportunity to venture out.I took the dog for a walk across the grounds. There are 5 buildings in the complex, with plenty of space between...
    JosetteLaRoc JosetteLaRoc
    Jun 9, 2012
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