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I Went Out In Public Crossdressed

Personal Stories, Advice, and Support 297 People

    1st Time

    I decided to go out the other night for the first time. I was wearing black silky pantyhose, daisy dukes a hoodie and some CFM pumps. I decided to go pump a tank of gas i was really nervous but while i was pumping gas an old man and a young man were checking my legs out it felt...
    Hosenheels84 Hosenheels84
    26-30, M
    1 Response Jan 18, 2012

    In The Beginning

    When i first started going out dressed,i would wear something femme underneath my clothes. Just knowing what i was wearing was excitement enough. But the more i went out the more i wanted to show. I came to the realization that i was an exhibitionist. I eventually started...
    mkydwg mkydwg
    41-45
    Jul 21, 2013

    My wife had picked a white with navy pinstripes

    sleeveless pencil dress, just above knees, and a matching solid navy short sleeve bolo jacket for me to wear one spring Saturday. I chose all white undies and navy heels, 3", and my navy clutch. Pearl earrings and necklace, silver watch on one arm and a silver/black onyx slave...
    CdKimmi CdKimmi
    66-70, M
    1 Response Dec 17, 2015

    Millie In The Casino

    When I assume my feminine personality I call myself Millie. Tonight Millie went out, fully dressed. Little black dress, black stay up hose with stripes, undergarments to hold me in and poke parts of me out, a nice curly wig, a ;little makeup, everything. Millie went to the...
    Roscoe75 Roscoe75
    51-55, M
    Mar 21, 2012

    Crossdressing In Public

    Going out in public dressed for the first time is scary and makes one very nervous. However at the same time it makes us very excited also, even just thinking about it makes us very excited. It can take weeks, months and even years to build up the courage to go out in public...
    pantiescouple pantiescouple
    26-30
    2 Responses Mar 6, 2012

    Last Night, Maybe Again Tonight

    I went out for a drive last night, the first time. I put on foundation garments - a girdle and a top, to help hold in all the extra parts, a bra with inserts, a skirt and blouse outfit, and pretty black flats. A curly wig and a hair band the lady in the wig store showed me how to...
    Roscoe75 Roscoe75
    51-55, M
    Mar 21, 2012

    Picked Up In The Parking Lot

    Igot dressed up pretty for an afternoon of shopping. It was mid-day, so I didn't dress TOO slutty, just pretty and sexy--a close fitting brown patterned dress that showed off my figure well over the usual sexy lingerie, black back-seemed stockings and black 4" heels with ankle...
    barbarascampbell barbarascampbell
    41-45, T
    5 Responses Apr 28, 2012

    Did It Again Tonight

    Tonight I had to pick up my roomate. I was already in my leather mini and platform heels so I threw on a coat and walked out to the car. I had to go across town so I had stay dressed the whole time. I drove along worried that somone at a stoplight might see my exposed legs the...
    deleted deleted
    26-30
    3 Responses Oct 26, 2011

    Fun And Disappointment

    Decided to go out and took great care to do my makeup as well as I could given both my limited skills and available items. After an hour of fussing, I thought I had done well enough to feel confident in being seen in public. So into the car I went and off to town where I walked...
    SexyTiffanyCD SexyTiffanyCD
    41-45, M
    1 Response Jun 1, 2012

    I Finally Did It!

    I'm happy to say that not only did I dress up on halloween but, I actually went out in public while still dressed up!!! I'll start from the beginning, I work nights as package handler (please keep the minds out of the gutter people) at a near by FedEx so I already knew I probably...
    deleted deleted
    26-30
    2 Responses Nov 1, 2012

    Going All Out!!!

    I have probably written this story in another group somewhere, there are way to many groups about the same topic, just a different title. Well anyways, I have been "out" several times dressed up completely from wig to heels, including jewelry and nails. My first time was a long...
    davis36a davis36a
    61-65
    1 Response Nov 18, 2011

    Exposed Many Times

    i have been exposed in public many times rather than add stories i have previously posted i would like to refer you to my stories list and photos would love to hear your comments
    sissypolly sissypolly
    41-45, T
    Jan 18, 2012

    My Fishnet Dress

    At one time,i had an ongoing lover. Whenever my gf would go to sleep,i would go out somewhere to dress and meet him. He would drive back to his place, which was a hi-rise apartment with security and visitors had to sign in. The plan wad always for him to pick me up and we would...
    mkydwg mkydwg
    41-45
    1 Response Jul 21, 2013

    I was wearing a lacy breast halter,

    matching garter belt and bikini panties under a sheer serape style nitie with four inch black pumps and midnight blue sheer nylons. My face, hair and nails were done perfectly after I spent the entire afternoon doing them. I didn't stop to think about what I was doing just put...
    amandatrane1 amandatrane1
    51-55, T
    1 Response Oct 29, 2015

    My First Trip Fully Dressed By Myself!

    I put on my lingerie, complete with garter belt, thigh highs, thong and my favorite black bra, and my new sheer dress and heels and ventured out to the adult book store/video theater by myself last night! I have been there before several times, but never in full drag. God it was...
    tulsasissy tulsasissy
    36-40, T
    1 Response Dec 22, 2009

    Halloween

    It was 1981. My then fiance and her sister were going to go dressed as hookers and my friend and I were going to go dressed as cops. My fiance's sister suggested that we reverse the roles and despite my "apprehension," I "reluctantly" agreed. No one knew how I so badly was...
    deleted deleted
    26-30
    3 Responses May 21, 2012

    Crossdressing Is Cool.

    I recently performed music in a skirt, fishnets, and a ton of makeup in front of about 4000 people. Nothing but compliments. Even got noticed the next day in a park about 15 miles away from the performance. In some circles being a dude in a skirt makes you more likeable. I...
    Candace75 Candace75
    36-40, M
    3 Responses Jul 4, 2012

    My First Time Out In Public And It Was A Blast!

    A few months back a couple of friends told me about a bus trip a local lingerie store runs where everyone dresses up in some rather out there adult orientated costumes and go on a booze trip on a bus around a few pubs and have some fun... This sounded like a fun and safe way to...
    undacovachik undacovachik
    26-30
    1 Response Jul 10, 2010

    So Many "firsts"

    The real first was in winter, I had a stuffed bra, panties, stockings all well hidden under my clothes and the thickness of the winter coat insured that the presence of "breasts" would not be noticed. Over the years I gathered more courage and one night went for a drive...
    SexyTiffanyCD SexyTiffanyCD
    41-45, M
    Apr 21, 2012

    1st Time Crossdressed In Public

    This happend many years ago . . . . It was 7am on a spring sunday morning. The sun was shining, there was a slight cool breeze, there wasnt many cars travelling on the busy road i lived on. My house mate had been out the night before and it was quite big night but for some...
    Staceyfoxx Staceyfoxx
    36-40, T
    2 Responses Nov 16, 2011
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