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I Went Walking Dressed As A Female

Personal Stories, Advice, and Support 871 People

    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

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    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...
    Vanessacd1957 Vanessacd1957 51-55, M 5 Responses Jan 19, 2012

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    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

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    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...
    glasscitycd90 glasscitycd90 22-25 7 Responses May 24, 2013

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    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

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    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

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    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 1 Response Jun 23, 2012

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    Shopping Dressed As A Girl

    A few years ago, I felt confident enough to go to a local shopping centre dressed as a girl. It was late when I got there, around 8.00pm, and although I had really dressed down, girls jeans, girls tshirt over a tshirt bra and low heeled boots, it still took me a while to convince...
    KimBuffySummers KimBuffySummers 46-50, T 6 Responses Jan 9, 2012

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    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

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    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

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    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

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    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 95 Responses Jan 4, 2012

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    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 56-60, M 2 Responses Mar 17, 2013

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    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

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    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

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    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 8 Responses Oct 17, 2011

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    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 4 Responses Aug 31, 2013

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    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

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    Because It's Just Natural For Me To Do So

    Yes, I "got there". I believe in myself. Andie is me, not a secret agent. You want to know about Andie - you want to know why? Then I'll tell you if you really want to know. But don't patronise and don't treat me as a curiosity. I'm just walking, OK? Doing the shopping like you...
    Fullcircle Fullcircle 51-55, F 2 Responses Mar 19, 2011

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    I Went Walking

    only place i go out walking is accross the street from my house when my parents are gone or in the back ally
    addguy3455 addguy3455 18-21, M Oct 14, 2011

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    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 3 Responses Apr 17, 2010

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    I'd like to hear about it

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

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    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 2 Responses May 24, 2013

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    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 61-65 2 Responses Jul 16, 2012

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    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 6 Responses Aug 18, 2012

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    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

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    " 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 3 Responses Jan 23, 2012

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    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 4 Responses Aug 14, 2012

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    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 3 Responses Mar 11

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    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 5 Responses Dec 23, 2014

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    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

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    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

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    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

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    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...
    Vanessacd1957 Vanessacd1957 51-55, M 3 Responses Sep 11, 2011

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    Related Experiences

    My first time I went was in Milwaukee. I just seperated from my wife and had just recently had my first adult gay sex with a guy who picked me up at a bar. I went in, very nervous...
    lapsteel lapsteel 41-45, M 8 hrs ago

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    This group is about all fabulous females of size.Those big girls,those large wonderful full-figured women.Those BBW and SSBBW's .the thicker,the more curvaceous,the big chest sized...
    thebustierthebetter thebustierthebetter 46-50, M 21 hrs ago

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    Why do I love the female body? There's not enough words to describe all the joy it brings to me to worship and adore them.The softness of their skin,the twinkle in their eyes,the...
    thebustierthebetter thebustierthebetter 46-50, M 21 hrs ago

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    I hate getting dressed every morning cause I hate putting on clothes. I wait till the last second to put them on the I take them off the first thing when I get home.
    Nakedtoday Nakedtoday 26-30, M 2 Responses 1 day ago

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    I can't stop myself from dressing femininely! I've tried to but couldn't, literally ( see other posts ). All I really know is that when the compulsion, obsession or whatever it is...
    amandatrane1 amandatrane1 51-55, T 1 day ago

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    At one point I lived in a duplex and there was a woman about my age who lived in the downstairs apartment. We shared a basement with laundry facilities. I occasionally looked at...
    iwishmichelle iwishmichelle 31-35 3 Responses 2 days ago

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    I am a middle-aged female, age 56, who is looking for people, male or female to connect with. Don't know who I am anymore! Maybe it's the "mid-life crisis"! I don't feel attractive...
    rhondalutz1 rhondalutz1 56-60 1 Response 3 days ago

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    I am a female switch, In need of a female sub to Dominate in order to stop flexing my Dominant side when I am supposed to be submitting
    247slave4u 247slave4u 36-40, F 2 Responses 3 days ago

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    ****, I was so scared to hit this button. This is something that I've always wanted to do. I guess since I already where males clothing I already am to an extent. But just for the...
    DriftingLeaf DriftingLeaf 18-21 1 Response 3 days ago

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    Why do I love the female body? There's not enough words to describe all the joy it brings to me to worship and adore them.The softness of their skin,the twinkle in their eyes,the...
    AfanOfbigNaturals AfanOfbigNaturals 46-50, M 2 Responses 5 days ago

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    I came out to a co-worker (friend) today, I knew she would understand because we have talked to great length about transgender issues. I took the opportunity to show her how I look...
    Idare Idare 51-55, M 14 Responses 5 days ago

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