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

Personal Stories, Advice, and Support 722 People

    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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    I'd like to hear about it

    and see some pictures. Message me for my email.
    ar29605 ar29605 22-25 Feb 9, 2014

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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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    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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    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 4 Responses Jun 28, 2011

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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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    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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    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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    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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    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 17 Responses Mar 25, 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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    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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    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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    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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    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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    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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    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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    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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    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 5 Responses Jun 9, 2013

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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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    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, 2014

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    Related Experiences

    I am a major sissy all because elf one experience. The first time I was put in girl clothes. This happens a lot and no one knows how much I enjoy it. It started on a camp i was...
    TheOneSissyJonny TheOneSissyJonny 13-15, M 1 Response 14 hrs ago

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    once I went in my sisters house who was living alone in Arunachal Pradesh I was going alone and there we two only living in India I was getting a very pleasure there but I didn't...
    in8444 in8444 13-15, M 1 Response Jan 1

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    today is the first time ive ever got high. i dont rite this to be an badass or think im cool or something, 'cause im not. i rite this cause i think i will forget this in the...
    andylovesyou23 andylovesyou23 13-15, M 4 days ago

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    Yeah this was probably one of my recent embarrassing stories. Two days ago, I asked out a girl who I thought was really cute. I didnt think she was in a relationship because she...
    Xychorite Xychorite 16-17, M 3 days ago

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    I ran track in high school, the first year of college, and the first semester of this year. Shortly before I started college, I got into bloating and stuffing. I only did it every...
    BellyFullOfSweets BellyFullOfSweets 18-21 1 Response Jan 6

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    On the 2/1/2015, i tickled my sister for the first time in 2015. This time i used an electric toothbrush. She certainly felt the difference between brush and finger. I used the...
    Delphi111 Delphi111 13-15, M Jan 2

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    We had been best friends ever since we met 10 years ago, but 2 years ago we had a massive, awful fight and hadn't talked since it happened- it was a terrible fight filled with...
    lemonjaide lemonjaide 18-21, F Jan 10

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    During Life, there is always a moment for doing things for first time, the first day you walk, speak, first day at school, work etc.. Sometimes, even if you have learned the...
    mrtt80 mrtt80 36-40, M 1 Response Dec 28, 2014

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    I remember when I was young, I was really fat and had intense anger issues like worse than now, and like my cousins would bully me and treat me like crap cause I was the only fat...
    brownzugar brownzugar 16-17, M 1 Response Jan 5

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    I struggled for years with self harm and depression and in my previous relationship it was a source of conflict and something used against me in arguments and something to make me...
    arirose43 arirose43 16-17, F Jan 9

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    Friday morning I drove for the first time it was amazing best experience of my life I was pretty good for my first time actually
    ashleysokolik ashleysokolik 13-15, F 2 Responses Jan 17

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    I am a first time mom to a beautiful 6 month old boy Emerson. He has been such a relaxed and easy going baby...till now. He seems more clingy and refuses bed time. He was sleep...
    lesleymomof1 lesleymomof1 22-25, F 1 Response Jan 6

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    I've never had my first time but I want it to be special
    Babyblue95 Babyblue95 18-21, F Jan 10

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    I liked an 14 yr old girl called Cathy, she showed me her boobs when I was 9 and I was so jealous. She was so pleased with her new look and I was so jealous. I had been trying to...
    Lin79 Lin79 31-35, T Jan 12

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    I was in my 8th grade english class in New Jersey. the whole class was silent while fox news was showing live footage of what was happening just 40 minutes away from us. When the...
    eggman667 eggman667 26-30, M 1 Response Jan 18

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    I was 18 years old my senior year of high school. I transfer to a predominately white school. White men and some women were attracted to me. Before at my other school that was...
    BrownBeeCa BrownBeeCa 26-30, F 4 Responses Dec 28, 2014

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    it was 3 summers ago and it was a brutally hot summer day. i had on my usual string bikini and I walked up the beach past the crowded area, i dont know maybe a kilometer past. i...
    jennafreespirit jennafreespirit 22-25, F 13 Responses 5 days ago

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    once in 2011 when I went in my sisters home who was living alone there in the table I was reading a book and there I saw two forms of any program that was held I fill up the form...
    in8444 in8444 13-15, M 3 Responses Jan 8

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    Nervous anticipation and fear that I wasn't woman enough for him, and with that first gentle caress so reassuring that not only was I but that he wanted to be with me.
    Mrskatearch Mrskatearch 31-35, F 1 Response Jan 14

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    when I was fourteen once I again went in my sisters house who was living in aurnachal pradesh and there in the last vacation i had to spent my vacation on wearing and living like a...
    in8444 in8444 13-15, M 1 Response Jan 1

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    I was over my friends house, with 3 other dudes and we just wanted to get absolutely hammered. we got fireball which pretty much did the job, because I saw 2 bo burnums as we were...
    figuringitout00 figuringitout00 18-21, M 6 days ago

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    I Remember back when i was young and I couldn't wait to get outside . back in the days when i never had to worry about anything. I was always happy and I couldn't wait to get...
    EnjoyTheSilenceX EnjoyTheSilenceX 13-15, F 1 Response Jan 5

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    8 days ago. I was teary, because of the alcohol in my system. I could hardly walk straight.
    Profweird Profweird 18-21, M 2 Responses Jan 7

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    I was in 8th grade American History. Period 4. I had just walked in the room and the teacher had it on his tv in the back of the room. I thought it was an accident and then I saw...
    HorseGirl21 HorseGirl21 26-30, F 3 Responses Jan 9

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    The international dialling code for Barbados is +1 246 followed by seven digits. When on-island just dial the seven digits. If you're staying in a villa do check to find out if the...
    Darronbanksso0 Darronbanksso0 31-35, M 1 Response Jan 2

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    I was at work in Michigan but had lived in upstate New York before that. After the first plane hit, I said we are under attack but no one believed me until the 2nd plane hit. I was...
    ldehaan1 ldehaan1 56-60, F Jan 4

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    I am lucky that I am able to dress as a woman 24/7. I love the feel of going out wearing panties and stockings under my dress and listening to my high heels clicking against the...
    Amandamichelle Amandamichelle 36-40, T Jan 11