I Went Walking Dressed As A Female

Personal Stories, Advice, and Support 894 People

    I Love Walking In Heels..

    Walking as a female is one of my favorite things. I started wearing my mothers and sisters heels when I was about 9-10. The 1st time I ever came, I was wearing heels! It was a pair of burgandy peep toe pumps. They don't fit anymore but i still have them ! It didn't take long...
    2647Cindy 2647Cindy
    56-60, M
    10 Responses Apr 17, 2010

    Went Farther Than Ever BeforeFirst,

    I want to apologize a little if I wander a bit while describing my experience.  There are just so many thoughts I want to write about, but they cannot be expressed all at the same time!Last night (Wed., 21-Oct) the weather forecast for early this morning (basically...
    wcurnow wcurnow
    46-50, M
    Oct 22, 2015

    Window Shopping

    I can still remember my times walking around a shopping area I'm a beautiful long gown and heels having so much fun nervous about being caught but it was so much fun !
    ladylike30 ladylike30
    41-45, M
    1 Response Mar 1, 2013

    The First Time Outside Dressed

    I will never forget the first time I felt the fresh air on my nylon clad legs and heard the sound of my own heals on concrete. I was in a gay club and it had a long open walkway to the street where only people coming into the club would be, and they were going to see me anyway. I...
    GertieWhite GertieWhite
    61-65
    1 Response Feb 18, 2013

    I'd like to hear about it

    and see some pictures. Message me for my email.
    ar29605 ar29605
    22-25
    Feb 9, 2014

    First And Last Time (For Now)

    Last summer i was left alone at the house for a full weekend and spent the most of it crossdressing which is just fun in itself. One day I bought a new pair of heels and wanted to try them out since i only dressed and walked around the house. So I got dressed wearing my denium...
    deleted deleted
    26-30
    8 Responses May 24, 2013

    All The Time

    I love dressing in women's clothes and walking. walking is great exercise. And doing it dressed as a woman is just natural. It's more pleasant when it is not the dead of winter so will be more fun now that Spring is just around the corner. Try it, you will feel so much better
    jml2000 jml2000
    61-65, M
    2 Responses Mar 17, 2013

    Went For A Walk

    I was around twelve and I got up the nerve one nite to take a walk while I was dresses. It was late and I was going to go to the gas station that was about a half mile away. I put on tan pantyhose, pantys, a tennis out fit of my sisters. It was a pink pleated skirt with matching...
    ammilnet ammilnet
    36-40
    5 Responses Aug 18, 2012

    " Down By The Lake "

    One of my most memorable experience of walking dressed as a woman was one day I went to the lake. I got all ready, did my make-up and put on a sexy bra and matching panties and I very short black and white dress. I chose my strawberry blond wig. I was all ready to go and I looked...
    davis36a davis36a
    61-65
    2 Responses Jan 23, 2012

    Yes I Went For A Walk

    dressed as a female unfortunately  the heel of my shoe broke off and my wig fell off when I bent down and the police saw and took me to the mental hospital called Lakehead Psychriatric Hospital.
    aquarius3 aquarius3
    66-70
    2 Responses Jul 16, 2012

    Its Fun

    i have walked around in rest areas in a skirt and top with my heels on i even went into the ladys loo
    spaz1177 spaz1177
    46-50, T
    Feb 16, 2012

    Next Step

    Love going out driving late at night compleatly dressed up in some of my favorite women's clothing. The next step for me as I just found out there is a Kmart store close by that is 24hrs So I want to get totally dressed Fem & go to the Shopping center shopping for women's...
    debracd debracd
    36-40, M
    5 Responses Jul 3, 2012

    Many Times

    I remember when there was no greater thrill than stepping outside, feeling the breeze on my legs and up my dress and hoping I'd somehow avoid detection.Back when it was daunting. Though over time things change. I became extremely comfortable in my own skin and presenting as the...
    Josie06 Josie06
    56-60, F
    2 Responses Jun 23, 2012

    Nothing can be more exciting

    than going out at night, fully dressed as a woman just hoping that you may meet someone who shares your passion. If there is anyone from the Birmingham area UK please do get in touch.
    binair10 binair10
    56-60, T
    1 Response Aug 21, 2015

    Ever have one of those days

    where things were going both wrong and so right? I was about 22 and spending the weekend in a nearby city where I'd left every vestige of my male things behind, well locked in the trunk of my car down in the hotel parking lot, so that even if I chickened out I would have to at...
    amandatrane1 amandatrane1
    51-55, T
    1 Response Sep 4, 2015

    This is a photograph of me in a London hotel

    room a few minutes before I went out for a walk around Charing Cross Road and Leicester Square, including a visit to a bar in Lisle Street.  It was clear that some people clocked me as trans, so I didn't 100% pass, but they seemed happy enough to accept me anyway.  It...
    clairemeredith clairemeredith
    46-50, T
    3 Responses Dec 23, 2014

    I Walk In My Backyard!

    I have gotten all dolled up before in tights, bra, panties, and a black dress with high heels of course. And then I walk in my back yard. I live in a house that has trees right behind it so I can hide myself pretty easily. I have also worn a dress and walked around my block at...
    Natalie121 Natalie121
    18-21, M
    1 Response Jul 21, 2011

    It Was Christmas 1960

    I had only know my best friend sense the start of 8th grade, and yet I had strange feeling for him and I know he had them for me I had been ask to spend Christmas vacation with him and his mother and I knew his grand parents were going to also be there and I was sort of still...
    rickibrat2 rickibrat2
    61-65, M
    1 Response May 24, 2013

    Last weekend May 3, 2014 I went on a walk with

    some friends. It was me, Aidan,Maria, Gavin,Madison, and Ashley. Aidan, Gavin and I were at Maria's house that day and we wanted to get out of the house and go outside. We didn't know what to do outside so we decided to go on a walk. Well we didn't have clothes to walk in. We...
    Sarahismygirlname Sarahismygirlname
    13-15, T
    2 Responses May 12, 2014

    Walking Out

    A couple of days ago I went out dressed with my wife and posted the story in another group. Having enjoyed ourselves so much and having a day off today we decided to do it again - well why not? So early this morning we set off before the neighbours were up and headed away in the...
    wetrev wetrev
    46-50, M
    1 Response Mar 5, 2013

    Mirror, Mirror ... What Makes A Woman?

      I sometimes wonder about many things, one being this question I have posed. Is it only the clothes that make a woman. Dresses, nylons and heels. Is it the doctor's proclamation at birth because of what he sees. Is it how many children she can have. It can't be just...
    Josie06 Josie06
    56-60, F
    2 Responses Jul 7, 2012

    Sometime Is Easy, Sometime Isn't

    I did it a few time. Especially since i member of this site, i became a lot of spiritual support, for be myself, and not hiding. So, i can say, im on the way. I go out more and more dressed as female, but the most of the time only one thing is missing: my high heel shoe, and of...
    VivienXX VivienXX
    26-30, T
    2 Responses Apr 17, 2010

    Skirting At Camden Lock

    This is a copy of the story I posted called "Camden Lock" in "I Went Out in Womans Clothes".  It might fit in here too. I had not long acknowledged to myself that I was CD and I wanted to see what it was like wearing a skirt out. For my trip I chose a black shirt and jacket...
    meganb1 meganb1
    36-40, T
    1 Response Aug 3, 2013

    One evening when I originally start to

    cross-dress and find out about myself I went out dressed as a female. My parents were not at home as they were on holiday. So I decide that late one evening I would go out for a walk dressed as Carrie. All I had to do was make sure I could get out the door without anyone...
    deleted deleted
    26-30
    1 Response Jan 29

    Today's Adventures In A Skirt

    I am having a nice Vanessa day today! I have spent all day as Vanessa, been working in the office. I drove out to see our lady at Transliving to pick up some supplies and came back, then ran out of cigarettes so walked about a quarter of a mile to our corner shop to buy some more...
    deleted deleted
    26-30
    3 Responses Jan 19, 2012

    My Ventures

    I've been dressing at home in our apartment off and on for very brief moments for the last couple of years. My wife tried passing it off as a phase. She says she doesn't mind, so long as I keep it inside our home. My wardrobe has only expanded slightly. I started out with...
    JosetteLaRoc JosetteLaRoc
    36-40
    May 13, 2012

    My Car Breakdown

    A few months ago I had to borrow a car from a friend because I was going to a horse race course and it was ladies day and there would be lots of glam girls and their super outfits there . I was wearing all white lacy undies and a short silver white pleated dress and all...
    pleatedgirly pleatedgirly
    36-40
    3 Responses Aug 14, 2012

    My Outdoor Adventures In A Skirt

    I used to drive my land rover back from jobs late at night. Put on a black pleated mini skirt about 17" with black tights and knickers. It was a wonderful feeling. I once did the same when I did some night time heavy goods driving for a friend. I also spend some time in my...
    deleted deleted
    26-30
    2 Responses Sep 11, 2011

    Wearing a mid thigh dress,

    three inch heels and a slightly longer coat I calmly walked out the door, down the apartment hallway and out into the night. It'd taken me an hour and a half to get ready between showering, shaving my body, setting and styling my hair, doing my face and polishing my nails; not...
    amandatrane1 amandatrane1
    51-55, T
    1 Response Sep 1, 2015

    First Time I Went Out Fully Dressed Up

    Up until June, I never got to go out in Public while Dressed up. All that changed when my friend wanted to take me up to a restaurant up in a more open minded part of town. To add, her boyfriend worked the kitchen, and was thinking on helping me find a job there, so I decided to...
    converselover110 converselover110
    26-30
    Oct 3, 2013

    First Time Wearing A Skirt In Public

    As an on again off again cross dresser from my early teens it was a big fantasy of mine to wear a skirt in public. But I let my fears prohibit me from doing it until I was about 30 yrs old. I was in Vancouver for a few days and i had some femme things with me so I decided that...
    0hBrandie 0hBrandie
    41-45, M
    74 Responses Jan 4, 2012

    Mine Is Going Walking In Another Sense.

    We all have fantasies and sometimes we live our fantasies as well. Yes mine is a fantasy but I have lived part of it as well. I enjoy playing sports especially golf and I have always wanted to go out fully dressed as a women golfer. I would luv to go out completely wearing...
    deleted deleted
    26-30
    Apr 15, 2013

    The Thrill Of It All...

    There is a very definite thrill that I experience whenever I wander out dressed in a skirt and blouse with my 3" heels and jewelry. My outings have generally been at night when most are sitting in front of their TV. I head out for a drive and find a spot where I can park and...
    DonnaSt DonnaSt
    66-70, M
    7 Responses Oct 17, 2011

    I went for a walk this morning at the Walmart

    in one of my dresses. It is just so freeing to wear what I want to wear.
    mat2Robin43 mat2Robin43
    51-55, M
    2 Responses Mar 11, 2015

    I enjoyed going out to the local Mall dressed

    as a female. I think some knew I was a transvestite, but it was fun when a 50 year-old woman just nodded a woman-to-woman "hi" as we passed in the doorway to Dillards. For her, I was just a fellow lady.For me, the finishing touch would have been nails. (Polish or artificial...
    brigittavt brigittavt
    56-60, T
    2 Responses Feb 25

    Trips To The Mailbox

    When I was in high school I had alot of free time during by myself in the summers, I would spend the mornings getting dressed up in some of my mothers old clothes Ithey were saved from the 60s and early 70s), if I could work up the courage I would take a quick walk down the...
    ashleigh83 ashleigh83
    41-45
    2 Responses Jul 27, 2011

    Walk In The Park

    Thinking back I now understand how dangerous it was, but it was so much fun at the time! I got the urge one night while dressed up, to go for a walk in the main park in Chicago. I was in knit top and plaid skirt, 3 inch pumps, and my cape. I hid a key in one side of the park not...
    Rheta Rheta
    61-65, T
    2 Responses Aug 31, 2013

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