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

Personal Stories, Advice, and Support 724 People

    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 12 Responses Feb 18

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    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

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    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...
    jane1976 jane1976 31-35, T 13 Responses Oct 26, 2013

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    18 Years Old ...

    Although I had been frequenting my mum's clothes and stuff when I was younger, as detailed in other stories, I had not tried makeup or 'came out' as a tranny when I was 15, I spent my first few years just dressed at home....not having the guts to go out..... Come 18 and mum was...
    TVCassandraSlut TVCassandraSlut 26-30, T 1 Response May 27, 2013

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    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 26-30 6 Responses Apr 1, 2012

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    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 31-35 2 Responses Nov 29, 2013

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    At My Grandma's House

    I was only twelve at the time when my grandmother became ill. My mother had packed my suitcase and when I came home from school I was told we were going to my grandmothers. She lived out of state in a rural area as she did not like the city life. Soon we were driving to her...
    Melodie13 Melodie13 61-65, M 9 Responses Dec 7, 2010

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    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

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    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 56-60 1 Response Jan 3, 2013

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    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

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    At 14

    At the age of 14 I was dressed as a girl by my mom for a costume party. I loved every minute of it. Here I was walking into a room full of people I knew wearing a dress and 4 inch heels. I was dressed from the panties up in moms clothes. They actually thought I was a girl just...
    Adam59 Adam59 56-60, M 5 Responses Feb 26, 2013

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    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 18-21 3 Responses Apr 8, 2013

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    The Dentist

    I doubt this was my first time taken out by mom as a girl ,but it is a time I remember, I now feel free to share and let others know what I did ,it is okay to share. Mom dressed me in a old faded print dress ,it once kinda pink, but it looked aged,I wore hose with a runs in...
    Kristen4 Kristen4 18-21, F 1 Response May 12, 2012

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    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...
    outdoors49366 outdoors49366 36-40, M 5 Responses Dec 30, 2011

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    Halloween

    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

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    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 41-45, F 3 Responses Nov 12, 2012

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    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 22-25, M 6 Responses May 26, 2011

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    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

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    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 36-40 6 Responses Jun 9, 2013

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    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...
    kayleew2000 kayleew2000 18-21 18 Responses Mar 25, 2012

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    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 22-25 16 Responses Apr 20, 2011

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    I'd like to hear about it

    and see some pictures. Message me for my email.
    ar29605 ar29605 22-25 Feb 9

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    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

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    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 22-25 11 Responses Oct 14, 2011

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    The Sweet Memmories

    OH those sweetmemmories I have of the smock type little cotton dresses and the excitement of having on those sweet little girlie panties are non to compare when i had to fallow along behind grandma when we went to get the cows from the pasture, or go with my wagon to get fire...
    karriefalon karriefalon 46-50, T Nov 27, 2011

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    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

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    Related Experiences

    I was alone that day got bored at home I was watching from window on road one girl was walking I saw her in salwar she was so feminine there was no one on road suddenly she makes...
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    I've had a day to think about it. And the more I think about it, the sicker I feel. I feel like sharing it here will help. That's all I can hope for at least. Last night I was...
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    When I was seven years old and in first grade, I had my tonsils taken out. I had sleep apnea and got strep throat often, and in class, I'd often be tired and hyper from not...
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    So the first time I got high was the summer of junior year into senior year. There was a beach day for one of the clubs I'm in at school. So my friend, her friend, and I went to...
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    i just lost my future wife. To some ******* muggers in the park.....i swear to god i will murder them if i find out who did this...i will kill them x'(. Anyways......Her name was...
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    My mom told me I was just a baby when this was going on. My dad worked at the World Trade Center during the time. He remembers that he was at the bottom floor of the building so...
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    I was 3 years old and in preschool at the time. Even 13 years later, just the thought of 9/11 brings tears to my eyes. The videos of people jumping from the towers just make me so...
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    My girlfriend is engaged to another man. I just found out, but she doesn't know that I know. The whole situation is ****** up. I'm not innocent either. I'm married, but she has...
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    I had a quiz in math class that day, I finished early and left. I stopped at a deli on my home for a pastry and chocolate milk for breakfast. On the tv at the deli I saw that one...
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    But for the first time in 1985 the team was crowned the Spanish Super Cup, "linen legion" up and down still maintained a humble caution. The team's midfield commander Gabi told...
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    I was on the way to work and had the local NPR station on the radio. Years earlier I had lived in New York and had even been in the World Trade Center about a 100 floors up. While...
    profsci profsci 61-65, M Sep 12

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    This was way back in freshman year, I'm a senior now. Since about 8th grade I wanted to smoke weed, I actually wanted to become a pot head. It's kind of sad but I was in 8th grade...
    Anonymous446 Anonymous446 18-21, F Sep 11

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    Hiiyyaa, Kayle here :D The reason I loved it was because I had no regrets about it, I see every day more and more people who complain because they wasted their first time and...
    Kaayyllee Kaayyllee 22-25, F 2 Responses Sep 8

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    For the first time, ever. Going on 2 years, we've been together. Nobody can possibly break that happiness. Perhaps they're jealous, I don't know. But all I know is that I am happy...
    Inherownwords Inherownwords 31-35, F Sep 9

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    I just did a full shave of my pubes (including balls) my *** and the tops of my legs of the first time at 14
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    I was 8 and we were in a summer camp with all of my class mates. I slept in a room with two others girls. The bathroom was maybe 300 metres away on a hill. At night I woked up...
    malacka92 malacka92 22-25, F 4 Responses Aug 23

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    ok heres the story my sister just recently decided to pursue exhibitionism. so she has been recently exposing her naked body in Public in a way that looks like it was an...
    district20 district20 22-25, M 2 Responses 10 hrs ago

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    I get this most of the time even in drab as i am slim and have long hair but feel much more comfortable dressed as a female
    girlynicole girlynicole 36-40, F 2 Responses Aug 22

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    i keep passing over this experience as i feel embarrassed or maybe ashamed that this is even a part of me. i was good at hiding this side of me from the time i was seven years old...
    trailsonrails trailsonrails 51-55, M 2 Responses 4 days ago

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    It was a few years ago. My mum went into the store to get some things since we just moved here, I told her I had to pee but she told me I would have to hold it. I never pee outside...
    ilovehalo ilovehalo 13-15, M 3 Responses Sep 1

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