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I Crossdressed and Went Out

Personal Stories, Advice, and Support 505 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

    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

    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, 2014

    I have been feeling extra Gurlie lately,

    today the wife made me promise to clear a path through the snow to the propane tank in the front yard so we could have it filled. she left for work as well as my two sons.so, here I am, all alone..... what to do????my belly was feeling a little uneasy, I didn't want to have an...
    JessicaMann JessicaMann
    41-45, T
    Feb 21, 2015

    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
    4 Responses May 27, 2008

    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

    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

    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

    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
    5 Responses Oct 18, 2011

    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
    46-50, M
    2 Responses Jul 22, 2013

    Took my granddaughters back home to their mums,

    a 400 mile round trip. Was fully dressed for the whole day, spent time at 2 motorway services and a petrol station. Even got "ladied". Was with my wife waiting for coffee & a gent wanted to pass saying "Excuse me please ladies". What a fantastic feeling. Not sure if this should...
    Monicatg Monicatg
    51-55, T
    10 Responses Apr 16, 2015

    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

    " 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

    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

    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

    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
    2 Responses Jan 6, 2009

    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
    2 Responses May 15, 2010

    It's just great when you go out

    and people genuinely think you're a girl. Someone asked if my girlfriend and I were a lesbian couple. He was just asking a question but to me it was one of the highest compliments I've ever gotten.
    Foxanne Foxanne
    22-25, T
    4 Responses Oct 31, 2015

    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, 2014

    Well gurls.. Here goes nothing.

    Going out today for the first time fully dressed! pretty sure I won't pass but I didn't do too bad of a job. Going to do a little Christmas shopping! Wish me luck!!
    Luv2cross Luv2cross
    41-45, M
    5 Responses Dec 21, 2015

    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

    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

    It might be cold as f€%# tonight

    but I'm going out like this tonight except I'm going to wear pink panties and black stockings
    kelliTxxx kelliTxxx
    36-40, T
    3 Responses Dec 31, 2015

    Been out for the first time

    since NYE. Day off from work so fully dressed , including my new wig. Did normal stuff including shopping at our local Tesco. Nervous at first but soon relaxed :)
    Monicatg Monicatg
    51-55, T
    4 Responses Feb 4, 2015

    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

    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

    I went out dressed for the first time on NYE.

    I was wearing a LBD and 3" peep toe heels. I walked the 1/4 mile to the pub and spent the entire evening as Monica before walking home again. It was fantastic & I can say that Monica WILL be going out again
    Monicatg Monicatg
    51-55, T
    8 Responses Jan 8, 2015

    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
    6 Responses Mar 6, 2012

    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

    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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