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I Crossdressed and Went Out

Personal Stories, Advice, and Support 487 People

    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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    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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    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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    In my fairly recent past,

    I would go out dressed about 3 times a week. I'd come home from my business, get ready, including polished nails and go out shopping or to the movies. I did it so often that I actually did the 5 minute makeup, lol. After getting together with someone, I stopped because this...
    slipgirl274 slipgirl274 61-65, F Aug 14

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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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    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 2 Responses Jul 22, 2013

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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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    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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    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...
    DonnaSt DonnaSt 66-70, M 4 Responses Feb 19

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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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    I was as fully dressed en femme

    as I could be, wearing 3 inch wedges, an embroidered sleeveless dress, earrings, necklace, and fully underdressed (incl pantyhose). I drove thru town with the windows opened, and even stopped and pumped gas at a remote gas island. It was early, but after the early morning rush...
    BixB BixB 61-65, T 6 Responses Apr 28

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    Sunday Experiences A number of years ago

    when I was dressing and going out on a regular basis, I attended my church as a woman. I was also a member of the choir and did singing as a soloist and in a men's quartet, all as a man. After a choir rehearsal, a female voice teacher came up to me and said, "You know, you...
    slipgirl274 slipgirl274 61-65, F 3 Responses Sep 8

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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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    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 4 Responses Sep 8, 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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    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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    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 2 Responses Aug 11, 2013

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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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    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 2 Responses Dec 30, 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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    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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    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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    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 21 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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    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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    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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    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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    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...
    DonnaSt DonnaSt 66-70, M 7 Responses Oct 18, 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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    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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    Related Experiences

    Well not in the snow but whatever. Anyways I was on the phone with my boy friend. Which is weird because he wasn't my boyfriend at the time and he randomly asks me if I have ever...
    heyitsashley53 heyitsashley53 13-15, F 2 Responses Sep 7

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    We were about 8 years old and my friend Joey and I were playing at a construction sight. There had been heavy rains so the huge square holes were full of water. We took two 2x4's...
    Deedle623 Deedle623 51-55, F 1 Response Sep 9

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    I loved going outside as a child. There were so many trees in need of climbing! So many birds to chase and so many trails to explore with my bike. Outside was where I wanted to be...
    guideme2truth guideme2truth 26-30, F 4 Responses 12 hrs ago

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    Today I'm going out wearing women's underwear. I've got my diaper(nappy). Plastic panties with a pair of pink flowered cotton panties. I also have a pink flowered bra on aswell...
    babyannie57 babyannie57 56-60, M 1 Response Aug 21

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    We would have dirt clod wars. There was a deep unpaved drainage ditch behind the houses across the street from us. After a heavy rain there would be a great deal of debris left...
    Deedle623 Deedle623 51-55, F 1 Response Sep 9

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    I finally did it! Tonight was the first time I went out dressed. It was just a small step but I felt like my heart was going to beat right out of my chest the whole time. So I am...
    Freja14 Freja14 31-35, T 16 Responses Sep 5

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    I wish I could do college over again. My whole life I played sports. I went to a good catholic high school met a wonderful girl my junior year and received a scholarship to play...
    LifeChanges123 LifeChanges123 22-25, M Aug 21

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    I've been with my kids mom for 7 years and have 2 kids,a 4 year old and a 1 year old. We had an up and down relationship because when we first started she didn't have an idea what...
    jay305 jay305 31-35, M 4 Responses Aug 28

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    Bare with me please it's a long story but I do need help! Okay so I worked in a photo studio place and as I love photography I figured I'd finally found a job I could stay in for...
    monstahmash monstahmash 22-25, F 1 Response 6 days ago

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    I just had my first date with a guy I like from school. It took me all summer to work up the nerve to ask him out, but I finally did and he said yes! We went out for pizza and then...
    aaronbernardo aaronbernardo 13-15, M 2 Responses Aug 22

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    A girl I met during CCA sorta charmed me and she gave me subtle hints that she's interested in me. I fixed up a date and we went out together. It's been a week and whenever my...
    KaiWong KaiWong 18-21, M Sep 8

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    It's difficult to let go, even after all the time that's passed by. Alexandria was one of those popular girls, the kind that had many friends and went out all the time, while I was...
    carmeloo16 carmeloo16 16-17, M 1 Response Sep 1

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    I was easily playing when my ******* brother forgot to get the charger, i told him to get it, mom comes and ******* slaps, i could easily shout but i didnt care anymore, she went...
    Crossfire14 Crossfire14 13-15, M Sep 6

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    Great time last night.Seemed to take ages getting ready and a big thanks to my sister who done my hair and make up.I met a man yesterday who i went for a coffee with and he asked...
    girlynicole girlynicole 36-40, F 12 Responses Aug 21

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    Last weekend I had to travel from one city to another. Before I ventured onto the train for a 2 hour journey, I plucked up the courage to change en-femme in the station toilets. I...
    chloesiobhan chloesiobhan 51-55, M 4 Responses Sep 4

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    I had on a black leather skirt that went to my knee and black and white blouse white open bottom girdle tan stockings white nylon panty white playtex 18 hour bra wig make up and...
    Betty9953 Betty9953 51-55, M 5 Responses Aug 21

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    And so does my wife, as do most women everyday. They go out dressed much like a regularly man and no one says a thing, but let a man put on more traditional women's clothing, and...
    onefourfun4u onefourfun4u 61-65, M 3 Responses Aug 23

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    I have been interested in female clothes ever since I was little, but I never acknowledged it much till I was around 18 or 19. I started to sneak into family member's rooms and...
    Eriborn Eriborn 18-21, M 2 Responses Aug 27

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    My wife sometimes lets me out in full femme mode,wig makeup blouse skirt 5" heels ......has let me go to a RSL club,the movies and a casino. I few looks but no one usually cares...
    tranny50 tranny50 41-45, T 2 Responses Aug 31

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    I Love to go out dressed as a tart. All black. Panties, open girdle (with suspenders), panties(usually a thong), bra (silicon implants), t-shirt, fishnet stockings, and mini-skirt...
    debbiestockings debbiestockings 56-60, M 1 Response Sep 8

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