I Remember The First Time I Was Taken Out Dressed As A Girl

Personal Stories, Advice, and Support 839 People

    I have a trip coming up

    where I will be driving about 4 hours. I am thinking of dressing up for the drive. I have a really short mini skirt, pink camisole, and 5" wedge sandals. Of course I will wear panties (probably a thong) and a stuffed bra. My bra straps will be showing. It will not look elegant...
    submike1234 submike1234
    41-45, M
    2 Responses Oct 2, 2015

    I was about 16 or 17

    and had revealed my secret to a middle aged man the night before by dressing up after he had picked me up hitchhiking. I'd spent the night at his place and expected to have to change back to male mode and go to school. Instead he phoned my mother again, ( he'd called her last...
    amandatrane1 amandatrane1
    51-55, T
    2 Responses Sep 29, 2015

    my first time out was

    when i was twelve. i was having a comming out party by going camping with my friends. the morning of at about 6pm my friend hailie came over and dis my hair for me. when anthony's parents arrived to pick us up we jumped in his moms honda while arron brian and anthony rode with...
    tgirlsummer tgirlsummer
    18-21, T
    5 Responses Feb 8, 2015

    First Time

    I do not know if this counts, my first time of being taken out dressed as a girl was last march at the age of 53 to have some photos taken of me dressed in female attire
    xdpaul xdpaul
    56-60, M
    Jun 12, 2011

    I previously wrote that I have a trip coming up

    that requires a 4 hour drive and I was thinking of dressing up for it. The drive is still a couple of weeks away. I have thought a lot about this recently. I was originally planning to wear a very short skirt, pink camisole, 5” wedge sandals, with a bra and panties. One...
    submike1234 submike1234
    41-45, M
    1 Response Oct 19, 2015

    Tonight an old friend came by

    and caught me with my sissy box opened on my bed. She dressed me like the picture, and drove to Walmart. She parked directly in front of the store, and left me buckled into the front seat. I have no idea how many people looked at me during the 20 minutes she was shopping. I...
    sissyrachel48 sissyrachel48
    66-70, M
    3 Responses Oct 29, 2015

    Shopping Trips With Mom.

    My 2 olders sisters started dressing as a girl when I was 5. I was out and about but didn't really know what was going on at that age. When I was 10 my mother took a real interest and started dressing me as a 10 year old girl. I had just finished school and was out for the summer...
    femboy4u femboy4u
    15 Responses Apr 20, 2011

    New Neighborhood

    when i was 7 years old, my family decided to move. i don't remember where we lived before then though. now my dad left before my mother knew she was pregnant so... yeah. and i had a twin sister.As we were moved in, i wanted to ride my bike. my mom said it was ok if they have...
    nicole9000 nicole9000
    5 Responses Apr 8, 2013

    Trip To The Grocery Store

    I spent much of my childhood being raised by my grandmother. My father was in the military, and was a pilot, and was often away. My mother very much liked to just hand me off to my grandmother and let her raise me. I would see my parents often, but spent the substantial...
    ThomasCarroll ThomasCarroll
    3 Responses Nov 29, 2013

    My brother had been letting me dress him

    for about 6 months and a the tender age of 14 he looked good. We had practiced all the walking and gestures. To see him strut around the house was funny. One day my mother came home from work early and caught us. My brother standing there in a dress wearing 2 inch heels ,hair...
    lisaann21 lisaann21
    22-25, F
    6 Responses May 10, 2015

    It was a Friday night

    and I had just arrived to a hotel in New Orleans. I was with one of my friends that knew i wanted to be a girl and she had been planning to take me out as a girl the whole time. She had brought enough clothes and then some for both of us for the week. The previous week she had...
    Kristen72 Kristen72
    22-25, T
    14 Responses Feb 18, 2014

    Aunties Little Sissygirl

    I was 10 years old when my aunt decided to put me in dresses at home. She put me ina yellow dress and lace panties with a training bra.maryjane shoes and knee socks.she took me to a salon and had my hair curled and put a bow in my hair.we spent all day at the mall practicing...
    Tracygellar7 Tracygellar7
    7 Responses Oct 14, 2011

    Did it on a dare. Dress,

    stockings. And shoes
    pardax pardax
    16-17, M
    3 Responses Dec 29, 2015

    As A Child

    even always being told they wish i had died and my twin had lived. i do not remember being dress many times as a girl , but then i do not remeber a lot of earler childhood have seen pictures of me dress as a girl when very little and have seen a trick or treating picture of me...
    rickibrat2 rickibrat2
    61-65, M
    2 Responses Dec 15, 2010

    This One Is For My Leah.....

    I am already female, so going out for the first time in a dress was no big deal. For Leah however going out dressed enfemme is a thrill for him. When I first met him two years ago at a drag show he was dressed very fashionably and even trendy for his age. I especially liked the...
    crsdrsr61 crsdrsr61
    61-65, M
    3 Responses Nov 12, 2012

    Guess This Counts

    Do not know if this counts as being dressed as a girl by someone but here is my story It was the first day of summer school in 1960, and it had been an interesting summer so far and we had both grown a lot over the last month. ( a doctor made choices at her birth that would have...
    rickibrat2 rickibrat2
    61-65, M
    1 Response Dec 31, 2010

    Going Out Dressed Like A Girl Wasn't Necessarily What I Was Planning,

    I was young, probably about 8 or so and I had been playing all day with my sister (10 year old stepsister actually). My father passed away about a year earlier. It didn't seem like a big deal but somehow I let my sister talk me into dressing like her girlfriend to play house...
    deleted deleted
    17 Responses Mar 25, 2012

    The first time I was taken out dressed

    as a girl was to a Halloween party. My girlfriend at the time went as the quarterback and I was the cheerleader. She even made me a pleated skirt to wear and her mom got me an oversized bra to wear. They both got into it by curling my fairly long hair with a curling iron and her...
    ReneeTalley ReneeTalley
    61-65, M
    5 Responses Jan 13, 2016

    It were some of the best days of my life.

    My older sister Lily, would always complain to my parents that she wanted a baby sister. She wanted someone to share her girl toys with and play with and I guess having a year-younger brother and baby brother didn't help that for her. She would cry that she was the only girl in...
    TimMatthews TimMatthews
    18-21, M
    4 Responses Jan 25, 2016

    My Gf 21st Birthday

    the first time i went out dressed as a girl was for my girlfriends 21st birthday we had been dating for just under 2 years.about 2 months after we started dating i told her that i had always wanted to dress in womans clothing and that i had done it a few times when i knew that i...
    deleted deleted
    3 Responses Dec 30, 2011

    I'd like to hear about it

    and see some pictures. Message me for my email.
    ar29605 ar29605
    Feb 9, 2014

    And at about age 16 I tried it myself,

    "what a train wreck !" Went to a thrift store buying a wig,girls jeans,high heel's and a frumpy sweater,borrowed mom's pantyhose and bra..."no one was home" did a clownish make-up job and took walk.....dead of winter,heels too tight,stuffing falling out of bra and frozen. It was...
    deleted deleted
    2 Responses Sep 2, 2015

    Halloween '09

    The first and last time I went out as a girl was Halloween of 09. It was my last Halloween before boot camp and my friends had always teased me that I should dress like a girl because when we would play D&D (Dungeons&Dragons) I would often play female characters. So that...
    CDX21 CDX21
    26-30, T
    4 Responses May 26, 2011

    I can remembering having a similar experience a

    few years ago. I always had to travel a long distance your business and will driving I always felt what it would be like driving it in my femme self. So I started planning my trip keeping in mind stops going to the restrooms and if needed gas stops as well. I also had to plan...
    deleted deleted
    1 Response Oct 3, 2015

    The Time I Enjoyed Best

    it started in 8 th grade when the person i loved want to go to schools as she had been born not how she had been forced to live in the past we were sitting in a big resteraunt eatting dinner and talking about summer coming up in just a week and we knew it was going to be busy...
    rickibrat2 rickibrat2
    61-65, M
    May 13, 2012

    I Learned From Day One To Hate It

    but then again most would if you got the idea you were only be dressed as a girl for some one to use as a girl
    rickibrat2 rickibrat2
    61-65, M
    May 13, 2012

    First Time Out Dressed As A Girl

    Well, I finally did it a couple of weeks ago, after seeing an event on Transtastic.com, I got up the courage and mentioned it to my girlfriend. I have never been out of the house dressed up and she dared me to do it. Of course, I didn't need much persuasion and we were soon...
    algina algina
    7 Responses Jun 9, 2013

    I was 13 and went out on Halloween dressed

    as a girl. I had on a hot skirt, panties, garter belt and just a bike on to keep my junk close to me. It was a night I never will forget because I looked like a hot blond model and picked up two teen boys out for candy. We kissed each other with tongue down past my tonsils...
    Ronan12 Ronan12
    18-21, M
    2 Responses Dec 26, 2015

    I am planning another outing.

    I am planning to wear a pink camisole, black bra where the straps will show, a black skirt that goes to mid thigh, and boots with 3 inch heels that go up mid calf. I am going to a mall about 15 miles from my house. It is a suburban outdoor mall, so I can walk around quite a...
    submike1234 submike1234
    41-45, M
    1 Response Mar 29, 2016

    My First Time

    I was ten my first time. I had been dressing for about two years but aside from a few quick forays on the back porch I had never really been out in public. On this day father had some papers for a guy in a nearby town. Normally he would have mailed them, but on this day he...
    deleted deleted
    5 Responses Apr 1, 2012

    I Do Not Remember The First Time I Was Taken Out Dressed As A Girl

    i do not remember the first time i was taken out dressed as a girl as i had always been dressed as a girl from when i was born. i remember the first time i went out dressed as a boy as it was after two weeks after first starting school the school had sent me home with a letter...
    PoppyAnn PoppyAnn
    56-60, T
    3 Responses Jun 28, 2011


    my first time actually out and about as a girl was on Halloween. I decided I wanted to be a belly dancer. ask and I shall receive so thats what I went as to my friends party. at first no one recognized me, untill I spoke of course. well I had lots of complements on my costume and...
    loveme368 loveme368
    18-21, T
    3 Responses Jul 18, 2011

    When Daddy Is Gone

    I am among many of those who were little boys during WW II. All of the men, including my father, had gone to war, and the women at home idolized their little boys, above all. As is well known, many of the mothers, who had been left alone, found solace in letting their sons...
    BobbiJo2 BobbiJo2
    1 Response Jan 3, 2013

    My First Halloween

    My first memmory of being dressed like a girl was at halloween, i was about 4yo and i wanted to go out trick or treating as it was a last minute thing i did not have a costume to wear so my mother said she would borrow one frm my cousin, at that point i was happy, until she came...
    deleted deleted
    17 Responses Oct 26, 2013
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