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

Personal Stories, Advice, and Support 726 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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    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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    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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    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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    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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    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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    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 6 Responses Dec 30, 2011

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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 10 Responses Dec 7, 2010

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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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    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 4 Responses Apr 8, 2013

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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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    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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    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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    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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    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 2 Responses May 12, 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 19 Responses Mar 25, 2012

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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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    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

    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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    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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    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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    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 14 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 13 Responses Feb 18

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    Related Experiences

    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...
    QuietDaze QuietDaze 18-21, F 9 hrs ago

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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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    I was in boot camp. I had only been there for a couple days. When they first told us most of us just thought it was a test.. That they were just messing with us. So one of they...
    aquagrl aquagrl 31-35, F 2 Responses 5 days ago

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    I remember my first time with a guy, and also my first time with a girl ;) if you wanna hear the stories just message me :)
    Locachica93 Locachica93 18-21, F 3 Responses a week ago

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    The first time I got properly drunk I was 15 or so, at a work leaving party. I had a part time job at a small theme park. I remember demanding a pudding fork and brandishing it...
    papercastles papercastles 22-25, F 1 Response Oct 10

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    I was seventeen when I first started driving. I was scared, but excited. I knew I'd have my freedom soon. But mom was very impatient. When I got on the road, I couldn't keep the...
    ChelseaMonroe ChelseaMonroe 22-25, F Oct 16

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    I didn't for the first time but I am remembering it. I just got out of a long time relationship so I am thinking about this. Lol. She was blonde, a cheerleader. I was a football...
    Secondtimer Secondtimer 31-35, M 6 days ago

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    The first time I had an actual accident was when I was 15. I had drank a lot of water and had to go pee a little but ignored it and went to bed. As I tried to sleep I could feel...
    scratchgolfer scratchgolfer 16-17, M 1 Response 1 day ago

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    I was 13 and my friend convinced me to try some beer and I agreed,it was Budweiser out of a Carl's jr cup and drank at least 5 cups and got really hammered and fell off a bridge...
    denimman2014 denimman2014 31-35, M Oct 10

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    My first time getting "tipsy" was at my buddy's place in 7th grade and ride my bicycle home for dinner. Good times. Now that I'm 21, I've seen how expensive drinking can be, but...
    PuckDrop PuckDrop 18-21, M Oct 11

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    Hi. I am a 13 year old boy. We live in a apartment with two floors. Both are of us. But the upper one remains locked. Today, I told my mother that I want to take bath. So I took my...
    mylittlebra mylittlebra 22-25, T Sep 28

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    I had sex for the first time Monday night with the new man I am with and I felt him come in me (but when I got pregnant the first time I didn't ) but I was Nervous and it pain...
    Fanteyzhuh Fanteyzhuh 22-25, F Sep 25

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    ... and I am loving it! I feel happy for the first time in a very long time! I feel an overwhelming sense of freedom despite being a single Mum. I am not afraid. I know the...
    Fluurt Fluurt 22-25, F 2 Responses Oct 1

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    My husband and I been having problems just got married not to long ago we'll he has a drinking problem and when he's sober where so happy together n he drinks we still do good...
    Undercoverdarkness Undercoverdarkness 22-25 2 Responses 23 hrs ago

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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 70+, F 1 Response 3 hrs ago

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    Living in a house with 3 sisters two older, one younger, sealed my cross dressing fate. The odds of me being curious about all of their clothing were stacked against me and I never...
    nyloncrush nyloncrush 41-45, M 4 Responses Oct 13

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    It was New Year's Eve a few years back and I was at my then on-off girlfriend's house with some friends. We had gone to Walmart and a liquor store earlier that evening with one of...
    scrtasnman13 scrtasnman13 18-21, M Oct 10

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    I think it was when I was 14ish and it was my first party and I was totally innocent! I really wanted to impress this older guy that was there so I ended up doing shots with him...
    brookmay brookmay 18-21, F 1 Response Oct 11

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    I was in 4th grade and it was a rainy day at school so everyone stayed inside during recess. Some girls were running around the room playing their version of hide and seek tag. One...
    Lookin4Cracks Lookin4Cracks 22-25, M Oct 8

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    I was 15 then. And we were required to use a vodka bottle for our chemistry class. So my parents bought me one. When they were away, I felt the urge and need to try a shot, and so...
    blueisacoolcolor blueisacoolcolor 16-17, F 2 Responses Oct 11

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    I was only 4 then when my dad used his belt to spank me.... It was parent-teacher meeting ( ugh! ) and when my dad got my results and the remark, he was unsatisfied with my B and...
    ObedientWife123 ObedientWife123 36-40, F 1 Response Oct 13

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    I was on the way to school. West Valley College in Saratoga, CA. There was a memorial there for Nicole Miller who was on one of the planes. She was good friends with my girlfriend...
    fiendforlife fiendforlife 31-35, M 1 Response Sep 25

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    it is funny when i look back on what i would consider my happiest time in life and all i can see is my childhood, i struggled to find that happiness that had a a kid and i have...
    detniat detniat 26-30 1 Response Oct 1

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