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

Personal Stories, Advice, and Support 712 People

    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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    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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    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 5 Responses May 26, 2011

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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 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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    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 14 Responses Apr 20, 2011

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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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    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 16 Responses Mar 25, 2012

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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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    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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    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 4 Responses Jun 9, 2013

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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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    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 36-40 2 Responses Nov 29, 2013

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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 4 Responses Nov 12, 2012

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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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    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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    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 15 Responses Oct 26, 2013

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    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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    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 8 Responses Oct 14, 2011

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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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    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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    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 Jan 3, 2013

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    Related Experiences

    I remember the first time I dressed up I had actually was walking home one day and some were bullying me. they were trowing sticks and rocks at me as well as video tapping it. Once...
    Alicetrn Alicetrn 22-25, T 3 Responses Oct 28

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    ....and now it's haunting my life to a staggering degree. I was just turning 21 and living in hell due to a mistake I made involving dropping out of college to pursue the girl I...
    cyclone80 cyclone80 31-35, M 1 Response Nov 10

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    First I Remember at the age of 5 playing with boys stuff and told my older brother and sister my name is John Michael. But the first time I crossed dressed was 10-13 I dressed up...
    thatonegirl156 thatonegirl156 16-17, F Nov 14

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    A girl and her father. I'm not quite sure where to begin. Im twenty. A girl. The youngest of three. I have two older brothers, 24 & 27. My parents are (shockingly) not divorced...
    kmelody kmelody 18-21 1 Response Nov 14

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    The first time my wife dressed me for Halloween and some guy treys to pick me up. She thought it was funny. I had a great time.
    Snowycd Snowycd 61-65, M 1 Response Oct 25

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    So I just need to get this of my chest because it's been bothering me. So I have this major trust issue or rather that's what I believe. I think. I was raped by my brother on my 17...
    DeijiDaze DeijiDaze 18-21, F 1 Response Oct 24

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    I was in the first grade. I walked home that day and turned on the tv. I live in a different time zone, so I don't know what was happening in US at the real time. But all of the...
    PasiklydusiMigloje PasiklydusiMigloje 18-21, F a week ago

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    I think I was taken advantage of but I'm not sure. I blacked out. I don't remember if I was dreaming or it was real life. I just feel weird (not as in spiked drink weird, mentally...
    oceanskat oceanskat 22-25, F 2 Responses 3 days ago

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    My mom had bought them for me when we went school clothes shopping. I remember when I first put one on it was a little uncomfortable but looking in the mirror I like how they...
    Michelle1976 Michelle1976 36-40, T 1 Response Oct 25

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    Remember working at this Boy Scout summer camp in 1973. I was 17. We had access to the kitchen and they had these 1 quart industrial-sized flavoring extracts, like almond, orange...
    nozupr4u nozupr4u 56-60, M Oct 27

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    I got drunk before going to my first date because I was so nervous. Showed up and he was disappointed but he took care of me like a gentleman. First time drunk and my first time on...
    KarinaLin KarinaLin 18-21, F 2 Responses Oct 27

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    When people ask If I remember the first time I got drunk. Haha if u remember that u didn't have that much fun.
    MeganDawnn MeganDawnn 16-17, F Nov 2

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    I was invited out with some friends and ended up going over to one house and ended up sleeping there. When I was undressing I realized I had on my panties and so did she.
    CdHeatherstoneCd CdHeatherstoneCd 46-50, M 2 Responses Nov 14

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    You were always there for me. You inspired me deeply with your words of wisdom and your faith in me. You have never let me down or fall, you were there to support me and guide me...
    MsAviator MsAviator 18-21, F 5 days ago

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    Just had them taken out and now really sore haha
    naturelover111 naturelover111 18-21, F Nov 11

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    So, technically it's not the first time I went commando. But after I took a shower at 1am this morning I realized I was too lazy to find a pair of panties, sleeping without a bra...
    TurtlesAndLlamas TurtlesAndLlamas 18-21, F 17 hrs ago

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    First time with a man I Was wearing a beautiful gown an got down on my knees and took his full manhood deep.
    CdHeatherstoneCd CdHeatherstoneCd 46-50, M 1 Response a week ago

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    The first time I wore pantyhose I looked at my legs and I was thrilled to have them on.y legs looked good but you could see my hairy legs. So I shaved my legs and oh the feel I got...
    Adam59 Adam59 56-60, M 5 days ago

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    Back at school They all thought I was an outcast, car crash "A hopeless fool", They said to me And my girlfriend Said I messed up, will I ever grow up? In the end, I’m not gonna...
    GoodbyeLife GoodbyeLife 13-15, F Oct 31

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    this saturday , i have danced for the first time in my life . I am sure I will have a couple more dances soon. I got drunk after 3 years , thats the worst thing happen to me after...
    HopelessPhilosopher HopelessPhilosopher 22-25, M Nov 11

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    I literally felt as if I was an alien walking amongst 'normal' human life. My first high school was one of the most traumatic parts of my past. It was such a hard time of my...
    1lonelydaisy 1lonelydaisy 41-45 2 Responses Oct 24

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    Before any of this happened, I'm going to explain a story that has taken up one third of my life. In grade 4, a new girl came to our school. For grade 4 and grade 5, I was a but...
    MainMan1999 MainMan1999 13-15, M Nov 15

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    Before any of this happened, I'm going to explain a story that has taken up one third of my life. In grade 4, a new girl came to our school. For grade 4 and grade 5, I was a but...
    MainMan1999 MainMan1999 13-15, M Nov 15

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    On Halloween Eve, I dressed up, did my nails, and went downtown. I went into a bar and ordered a beer from a very nice, attractive girl tending bar. Unfortunately, they were...
    KurtPantyboi KurtPantyboi 56-60, M 2 days ago

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    It was so exhilarating. I couldn't wait any longer. I snuck into mothers room which was strictly off limits, found the pantyhose drawer, took off my clothes and put the pantyhose...
    CdHeatherstoneCd CdHeatherstoneCd 46-50, M 1 Response Nov 14

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