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I Crossdressed and Went Out

Personal Stories, Advice, and Support 468 People

    Bike Ride!

    I got up this morning, what a beautiful day!!! showered, put on my panties, nylons, tight jeans, and my riding boots. then a padded bra that adds a size or so, a clingy tank top, some fresh lipstick and my mesh riding jacket. fired up the bike and hit the open road!!! i'd never...
    JessicaMann JessicaMann 41-45, T 2 Responses Jul 5, 2013

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    Enfemme Dinner &Amp; Shopping

    I usually only go out enfemme, if dress, shoes, or lingerie shopping. I met an old female highschool friend, I hadn't seen in many decades, and she's a hair stylist. On a whim, since my wig needed styling, I took it, and my bag of clothes with me, in case I decided to confide my...
    JillXD JillXD 56-60, M 2 Responses Jul 5, 2013

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    A very fine evening- Hi my friends,

    it has been quite awhile since I have written a new story but then it has been awhile since I have been able to do some serious dressing. Over the last five days I have been able to dress en femme for all but three hours this morning. In addition I have been reading the...
    deven44 deven44 66-70, M 3 Responses Feb 19

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    Did It Once For Halloween

    I dressed totally glam one Halloween about 10 years ago - turquoise satin bridesmaid's dress, and underneath that, my sexiest maroon satin bra and panties, slip, and pantyhose, plus black patent pumps, long wig, earrings, jewelry, full makeup, perfume and nail polish. I went...
    JenniferSometimes JenniferSometimes 51-55, M 12 Responses Jan 1, 2010

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    A Bit Tipsy

    i'd been out one saturday night at my local, and had one over the eight. i'd recently bought a new dress  from tk maxx, and decided i needed a pair of shoes to go with it, ana handbag ...... oh and a new coat. anyway, when i was walking back home from the pub i was...
    manda1 manda1 56-60, M 1 Response May 15, 2010

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    Driving Dressed Up

    i love to dress up skirt sweater set full makeup wig heels and go for late night drive . find a place to park and go for a walk to hear the sound of my high heels.
    kate6262 kate6262 36-40, T 8 Responses May 27, 2008

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    when I was a teen I had a paper rout.

    every month I had to collect the money by going house to house. One time I got all excited with the idea of wearing my sisters panties, bra and slip under my boy cloths. I wen into the bathroom and slipped them on while my family was watching TV .The TV room was just outside the...
    jenifer6 jenifer6 56-60, M Dec 30, 2013

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    For over 12 years I crossdressed

    and went out almost nightly and many times in the day to do my "business" See the short skirt I wore to draw attention to my smooth White body. 
    CarolinaGayProstitute CarolinaGayProstitute 41-45, M Jan 19

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    When I Crossdress And Go Out

    im 16 and all i do is put on a bra and panties pantyhose and a dress and high heels then go sit out front or back yard
    addguy3455 addguy3455 18-21, M 1 Response Oct 3, 2011

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    Out Once More Feels Like The First Time

    I was able to get dressed up and go out this would be my third time fully dressed up with make up. I started with a shower and shaved my face, then proceeded to paint my toes with a deep dark purple polish. While waiting for my toes to dry to put a second cost on I put concealer...
    gdmidd gdmidd 41-45 2 Responses Sep 8, 2013

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    Meeting At A Bar

    Many years ago, I met a guy who wanted to meet me at a gay bar. After sharing a drink or two, we went to a motel and we both dressed in drag. I had a cheap black wig on. He was a blonde. He ordered me to lift his skirt and give him oral while in my nylons, mini-skirt, and sexy...
    pantiescouple pantiescouple 26-30 1 Response Jul 20, 2010

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    Leather Thong And Tight Dress

    I've dressed before but only to adult book stores and I had lots of fun. I wanted to branch out and see if I could really turn some ones head. I in the past could not stay dressed and not get hard, so I found this leather thong that I could used to keep my meat in check. I...
    Swingbang Swingbang 41-45, M Oct 9, 2013

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    It's My World Too Out There

    I guess it's an upside to being out of work. Redundancy came and I've decided I deserve a bit of a sabbatical. This is my window of opportunity to find, be, and establish my whole self, confidently in what can be an alien world. Just that bit of time to have the house to myself...
    Fullcircle Fullcircle 51-55, F 3 Responses Feb 4, 2011

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    Hello Everybody

    Hello everybody…how are you all…I have just joined this forum…well i am here to have fun and sharing some useful information. Hope I will get warmly welcome from all members…
    ZenFranklin ZenFranklin 26-30 1 Response Jan 4, 2012

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    Humiliated While Crossdressing

    I was on a business visit abroad and returning from a shopping spree after having purchased a whole lot of feminine accessories which I had carefully tucked in a leather bag that I carried with me. I am driving back to my service apartment late at night dressed in black...
    AnandChopra987 AnandChopra987 41-45, M 1 Response Jul 22, 2013

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    Often

    i have gone out awhile cross dressed on many occasions but not around where i live. i have gone out with relatives and a couple of female friends miles from home where i was unlikely to meet any one i knew. i would often get dressed and then wear baggy clothes over my dress and...
    Cyclopes66 Cyclopes66 51-55, M 1 Response Oct 1, 2012

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    All Dolled Up For A Nice Slutty Summer Drive Home

    I fortunately get to spend alot of time in my alter ego as Kimmie,and I'm all too happy about it.For 11 years I have lived as a woman,and work in a large finacial institution in loss prevention.The attire for work is strictly proffesional.Loving my legs,as over time I have...
    Kimmie1321 Kimmie1321 36-40, T 3 Responses Feb 15, 2012

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    At The Mall In Womens Clothes. Thursday 22/3/2012.

    This week I bought some womens slacks and blouse so I could walk around in womens clothes and not be obviously seen as a crossdresser. I put on a bra and panties, my waist cincher, a pink cammie and black pantyhose under the womens blouse and slacks. I went to a busy shopping...
    KarenStm KarenStm 61-65, M 9 Responses Mar 23, 2012

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    My First Experience, "I Crossdressed And Went Out"

    If you have read any of my previous stories you would know that I love wearing female clothes and have been in the closet for many years. When I was young my parents would go out and when they did my three older sisters would dress me up in their clothes, yes in the begining I...
    2wzh7i1t0h 2wzh7i1t0h 56-60, M 22 Responses Mar 6, 2012

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    Everyday

    I live as a woman so I feel it is not crossdressing anymore. Before I went full tome I would go out as a woman and would be ask out on real dates.  I never accepted as my wife thought it was nasty I would be ask out and she wouldn't many times.  She made it possible for me to...
    RunAroundSusan RunAroundSusan 22-25 May 1, 2013

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    Andie Looked So Lovely!

    Those who have traveled with me over recent months will know that I have looked forward to going out as my femme self, and have carefully worked on doing it as well as I can. All I wanted was to be free to claim my world, dressed as me, but without turning too many heads in the...
    Fullcircle Fullcircle 51-55, F 13 Responses Feb 18, 2011

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    Sooooo Much Fun

    I love going out dressed and love all the looks i get and if i wear something sexy and short and flash a little of my panty thats even better so to all you gg's out there now i know why you do it .
    deleted deleted 26-30 4 Responses Jan 6, 2009

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    My Halloween

    I'm not new to dressing, but recently went out dressed for the first time. I went to a TG club in the Chicago area on Halloween. I got to dress as a cheerleader. I went all out too. I wore panties, bra w/breast forms, midriff, tights and cheerleading briefs. Of course I had...
    mender12 mender12 26-30, M 1 Response Nov 19, 2013

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    " Goin' Out "

    I have gone out, in public several times. The first time was long ago. I put on a pair of pantyhose and a bra under short shorts and a tight top and went to a gas station in early evening. I had long hair them, so I kind of looked like a girl. Back then a young guy would come out...
    davis36a davis36a 61-65 1 Response Jan 28, 2012

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    Daylight

    I have been cross dressing for a lot of years now. Since I'm closeted my dressing occurs only a few times each year and then only for a few days at a time. Going out has been a part of the dressing for the last 10 years or so but often it is a very tentative sort of outing. Like...
    deven44 deven44 66-70, M 7 Responses Oct 18, 2011

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    Went Around Town

    Walked around town, a few years ago now around Glasgow and then Nottingham in a long pencil skirt.  Very scary, but felt great.
    deleted deleted 26-30 1 Response Jan 17, 2011

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    I Love Going Out Dressed

    ive been out many time dressed in my female clothes,usually i go to the supermarket on a sunday morning wearing a cute dress or skirt with full makeup,wig and heels.ive also been out dressed as a maid to a fetish night and plan on either dressing in a corset/skirt combo or...
    cdBethany cdBethany 22-25, M 3 Responses Apr 11, 2010

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    Driving Home!

    I do a lot of traveling for work and this is when I get to dress in my hotel with the occasional night trip out to get a little bit of a thrill and risk getting caught. Well this past weekend I had a unique opportunity for me.  I had a client dinner on a Friday night out of...
    alexhawke alexhawke 36-40, M 1 Response Aug 11, 2013

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    Related Experiences

    I went and drive around in my car dressed up today it felt good
    sexyaime sexyaime 26-30, M 1 Response Mar 21

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    Went to dunkin and got myself a carmel latte today mmm!
    Meegghan Meegghan 18-21, F Apr 3

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    I spent most of my life outside or pining to be outside. The tree in my backyard is more familiar than the walls of my bedroom. The woods were always better than any playground or...
    BleedingOrchids BleedingOrchids 13-15, F Apr 5

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    Still do! To this day my favorite way to spend my time is outside :)
    kaye23e kaye23e 22-25, F Mar 23

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    We did play first person shooters,though-with small rocks.One time we played Tron deadly discs-one of my neighbors got into their parents record collection...ah-good times.
    webalias3 webalias3 41-45, M 1 Response Mar 22

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    Who remembers those days????? Well, now six-year olds are on their iPhone5. An I'm working and going to college! STOP THIS PEOPLE!!!!
    KALELat17 KALELat17 18-21, F 8 Responses Mar 29

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    When I was a kid, my sister and I used to spend every summer vacation until junior high, to our grandparents house in the village.I returned there last week after almost 25 years...
    pois0nivy pois0nivy 36-40, F 3 Responses Apr 9

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    I wore a shirt that did not cover my skin grafts, from burn. He already knew about the scars but I usually cover up. The topic of scars never came up, I acted confident and by end...
    Badina Badina 46-50, F a week ago

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    I went out running today. I made this music playlist with awesome random music. I couldn't help but to think about love and what it's like. I see it in movies and I fantasize about...
    AugustAeonsworth AugustAeonsworth 18-21, M Mar 24

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    this happened when I was 6 years old one day me and my 2 friends were at day care when we asked if only we could outside in the backyard and go in the (vary small) pool. the...
    boynudist13 boynudist13 70+, M Mar 27

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    I used to have a social life. I used to go to clubs with friends and dance the night away with random strangers. And I used to drive everyone home safely too. I even found a club...
    Sinjintiger Sinjintiger 41-45, M Mar 29

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    Soo I'm back! I went out of state and now I'm back from my trip so your sexy asian chick is back c: did you miss me?
    ThisAsianLovesYou ThisAsianLovesYou 16-17, F 3 Responses Apr 7

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    Everyone if you haven't you should read my first story as this follows on. Well Karen and I talked to late and we decided we needed sleep so she gave me a nightie and gave me a...
    CDresser2 CDresser2 18-21, M 7 Responses 5 days ago

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    On Monday I put on a pair of black jean jeggings and a fushia colored peasant top. Underneath I wore matching black panties and a bralette. I completed the look with a black...
    Brandie1960 Brandie1960 41-45, M 4 Responses 3 days ago

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    Last night I went on another date :) it really was a fantastic night out. I was wearing a purple dress, nude tights and black heels. I felt really good in the outfit and had some...
    LucyTG LucyTG 26-30, T 1 Response Mar 27

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    Last night I went on another date :) it really was a fantastic night out. I was wearing a purple dress, nude tights and black heels. I felt really good in the outfit and had some...
    LucyTG LucyTG 26-30, T 2 Responses Mar 27

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    Today I went on a bit of a shopping spree for living as Lucy full time. I got a few skirts, dresses, tights, some heels and flats and some bra and panties. I came out with quite a...
    LucyTG LucyTG 26-30, T 1 Response Apr 1

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    Today was my first appointment at the Gender Clinic and it all went very well. The staff there were very welcoming and I was put at ease straight away talking to them. I made...
    LucyTG LucyTG 26-30, T 3 Responses 4 days ago

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    Im starting a Ki.K group chat ANY full time cross dressers under the age of 30 This is a chat for crossdressers to show off their outfits talk about shopping clothes and post like...
    lovevspink16 lovevspink16 18-21 1 Response Apr 5

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    I love to go out dressed as a woman. I wish I could do it every single day! Every year, my wife asks me what I want for my birthday. As my birthday is just a couple of weeks...
    SweetRhonda SweetRhonda 51-55, T 6 Responses 2 days ago

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    Last night for my date at the local t girl friendly club I was wearing a Red dress, black tights and heels. Felt wonderful being out fully dressed and the outfit looked lovely...
    LucyTG LucyTG 26-30, T 3 Responses Mar 22

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    Well that's me ready for my date, I'm so excited about meeting Alex at the local T Girl friendly bar :) I am wearing a royal blue dress, nude tights and nude heels. Underneath it...
    LucyTG LucyTG 26-30, T 6 Responses Apr 2

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    Well that's me ready for my date, I'm so excited about meeting Alex at the local T Girl friendly bar :) I am wearing a royal blue dress, nude tights and nude heels. Underneath it...
    LucyTG LucyTG 26-30, T 3 Responses Apr 2

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    Today I'm heading out to meet some friends at a local bar for lunch and a few drinks. I'm wearing a nice red dress, black tights and some flats. Gone for the sensible option on...
    LucyTG LucyTG 26-30, T Apr 12

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    Well I'm back from lunch and drinks with friends and had to write this to fill you all in :) I was having a wonderful time when I excused myself to go to the toilet. On my way back...
    LucyTG LucyTG 26-30, T 1 Response Apr 12

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    Well I'm back from lunch and drinks with friends and had to write this to fill you all in :) I was having a wonderful time when I excused myself to go to the toilet. On my way back...
    LucyTG LucyTG 26-30, T 2 Responses Apr 12