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I Went Out In Public Crossdressed

Personal Stories, Advice, and Support 271 People

    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

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    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 5 Responses May 21, 2012

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    Many Times

    I have been out in public fully crossdressed many times for many years.I also go out partially crossdressed.I don't always wear make-upĀ and my falsies. I only go out during the day.I go anywhere i want to.The hell what others think.
    cindyloulove cindyloulove 56-60, M 2 Responses Feb 19, 2012

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    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

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    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

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    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

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    First Time Out

    Well I finally got the chance and enough nerve to go out dressed as a female. My family left and I rushed home and pulled out everything I bought planning on this day. I started by painting my toes a deep red then put on a thong and a pair of toe less pantyhose almond in colour...
    gdmidd gdmidd 41-45 6 Responses Feb 7, 2012

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    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 3 Responses Jan 18, 2012

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    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...
    glasscitycd90 glasscitycd90 22-25 2 Responses Nov 1, 2012

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    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

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    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 4 Responses Nov 16, 2011

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    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

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    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

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    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 2 Responses Dec 22, 2009

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    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

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    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

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    New Year Celebrations

    This happened a couple of weeks ago. Some friends invited me to a celebrations being held for the National New Year. While talking of going there they mentioned that there was fancy dress involved, and, because of my waist length hair, asked me to go dressed as a girl in...
    shalinigirl shalinigirl 31-35 4 Responses May 9, 2012

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    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

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    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

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    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

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    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 2 Responses Jul 4, 2012

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    Related Experiences

    Been venturing out dressed more and more enfemme over the past couple of years. One day I shopped in a Michaels looking for a pink coat button for a feminine suit coat I have. I...
    debbienc debbienc 61-65, T 2 Responses Sep 28

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    I spent my childhood outside, literally only coming in for food and sleepz. Now I live in a smelly city and I stay indoors all day instead! :(
    papercastles papercastles 22-25, F 3 Responses Oct 9

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    I have 5 sisters, we would be outside from daylight to dark, playing with the neighborhood kids, we had a blast, our parents would have to drag us in at night, I miss those...
    Dixiechic66 Dixiechic66 46-50, F 3 Responses Oct 12

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    I needed very little to entertain myeslf as a kid. I had videogames, but I rarely played them actually when I was a kid; I did play them later, but compared to the great outdoors...
    cbones2010 cbones2010 22-25, M 1 day ago

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    We rented a house in the Mid West for a few weeks a few Winters ago. All 10 of our family were there, parents, and 8 siblings. It snowed, a lot, about 1 foot, which for me is a ton...
    LittleStain LittleStain 18-21, F 1 Response Sep 30

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    I used to be naked in my garden all the time. Although there is a house on one side there were enough trees to offer some protection and I only went out when they weren't there...
    Bartimaues Bartimaues 22-25, M 4 days ago

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    I am so tired. These past few months it has gotten worse. I don't know how to behave around new people or people I barely know, especially those I feel inferior around. That counts...
    haroni haroni 22-25, F Oct 14

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    When I was younger my home environment wasn't the best, and I thought I knew everything that I wouldn't end up in the same scenario. In fact I did start of differently I had a "I...
    lilygeorge12 lilygeorge12 22-25, F 1 Response Oct 5

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    I wear socks outside because it's fun. I'm just making up for fun I didn't have when I was a kid. When I was a kid my parents had a rule that I couldn't go outside in socks...
    Calcetines Calcetines 36-40, M 1 Response Oct 5

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    First of, I love to be nude and I've read alot of stories on outdoor nudity, so I thought to myself, why not try it myself? So, I've done it a couple of times earlier, but I'm...
    snowviking snowviking 18-21, M 1 Response Oct 3

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    I went out to a big Fair my town holds every year, and twice I was hit on by girls.
    TheMourningwhisper TheMourningwhisper 18-21, F Sep 25

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    They went out yesterday and sleeping without a fan is hard...
    YuriXWolfram86 YuriXWolfram86 18-21, F Oct 3

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    I went out on my first date since my boyfriend of 9 months and I broke up. Well, the person I was going to go on the date with stood me up. I wait for about an hour in the cold and...
    EowynElf EowynElf 16-17, F 8 Responses Oct 4

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    I went to have a couple of drinks with my life-long best friend, we go way back. He was having a difficult time with some personal issues and needed some "buddy time". Next thing...
    JessicaDale JessicaDale 51-55 Oct 4

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    Sorry if I misspell something, this is new for me. Okay... So a few weeks ago I was going to get dressed in the morning but I had no shorts to wear that day. I went to the dryer...
    ErickHernandez ErickHernandez 13-15, M 6 Responses Oct 7

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    A followup to my previous post. Here's how I looked out at the second club we went to last night. I'm not sure what made the bigger impression: the hair, the nails, or the 'girls...
    PennySterling PennySterling 51-55, T 1 Response 3 days ago

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    so I came home from a night out once with my girlfriend and happened to look up, before walking through the door. I'd been doing some astrophotography the previous day as there...
    jahosijhs jahosijhs 26-30, M 17 hrs ago

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    My new job has me working weekends, so my days off for the time being are Wednesdays and Thursdays. So I spend some of the time figuring out what I'm going to wear after I get out...
    PennySterling PennySterling 51-55, T 8 Responses a week ago

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    Seeing I dress as a woman 99% of the time, I consider going out as a male to be crossdressing. Last month I wore grey slacks and a blue blazer, white button down, rep tie and brown...
    josilver josilver 56-60 2 Responses a week ago

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    Last weekend I went on a hike up into my mountains. It was great to get back to the woods. There is something so calming and peaceful about the natural patterns of life that we...
    TryingToLoveLifeNow TryingToLoveLifeNow 18-21, F 2 Responses 21 hrs ago

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    Ok so I stayed all night with my 14 year old cousin and that day we went dirt bike riding. We were really muddy and it was almost time for bed. So I told him I wanted to take a...
    Jackson155 Jackson155 13-15, M 1 Response Oct 11

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    For many years I have worn high heels indoors. As a guy, its always been a passion, of how they look and feel when walking. its always been done indoors. Its always been with me...
    blindfoldstacy blindfoldstacy 41-45, T 7 Responses Sep 26

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    This summer, I twice went down to the lake and skinny dipped at night. It was kinda cold, and I didn't have any friends to do it with, but it still felt really good swimming around...
    Nopantson Nopantson 16-17, M 2 Responses 11 hrs ago

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    Went to the dentist and my mouth is still numb I keep biting my cheek D':
    DKG96 DKG96 18-21, F 10 hrs ago

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    Last night, three of my friends and I went shopping at the mall. I, of course, wore my spandex pants, which the girls are use to. Also one of the girls also wore her spandex pamts...
    swimguy0812 swimguy0812 22-25, M 1 Response Oct 4

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    The first thong bikini I bought came in a mixed lot of the clothes I bought on eBay. My family wasn't exactly wealthy when I was growing up so my sister and I had a really tight...
    missbec missbec 18-21, F 3 Responses Oct 12

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    I had this happen just this year. I live in a small Southern town and play baseball every Saturday from June to Sept. with the fire dept. We were playing the local police Dept...
    sportigus sportigus 31-35 2 days ago

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    We have a pool in the back yard I have 7 brother and sisters 3 brothers and 4 sisters with me that makes 5 girls. My parents where always a lot stricter with us girls then the boys...
    housewife4 housewife4 18-21, F 2 days ago