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

Personal Stories, Advice, and Support 731 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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    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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    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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    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 2 Responses Jan 3, 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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    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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    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 16 Responses Feb 18, 2014

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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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    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 3 Responses Nov 29, 2013

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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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    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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    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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    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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    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 18 Responses Oct 26, 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 3 Responses Nov 12, 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 8 Responses Oct 14, 2011

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    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 4 Responses Feb 8

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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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    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 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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    Related Experiences

    Babysitting slumber party Part 2: quick recap, I was being babysitted by 2 siblings for the first time. These two had dressed me up as a girl and we spent te rest of the night as...
    Boygirltime Boygirltime 18-21, M 4 Responses Mar 31

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    Babysitting slumber party part 4: read parts 1-3 for context. I had just aquired freedom from the babysitter's house but there were a few problems though, first of which was the...
    Boygirltime Boygirltime 18-21, M Apr 3

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    My first crossdressing was when I visited my sister at her house she is 25 years old and I was 13 years old today she was out so I was by myself I got bored so I went up to her...
    cutewolf197 cutewolf197 16-17, M 1 Response Mar 29

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    It was my 16th birthday party and it was basically my first time drinking. Now I've drank wine a few times with my family, but at my party we played beer pong but with vodka and...
    16gsavino 16gsavino 18-21, F Apr 19

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    I was 15, my bf suc*ed it first time in his room. He suc*ed it hard and kissed me too. That was the first time i became totally nude in front of any guy. But he was not the first...
    babbydoll12 babbydoll12 26-30, F 9 Responses Apr 9

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    A couple weeks ago I got together with an old friend of mine whom was kicked out of our school for being caught with weed. I was great friends with her before all of that and I had...
    ali1200 ali1200 16-17, F 5 days ago

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    To be more specific...my partner and I are getting our first house. I know home buying is supposed to be one of the most stressful life experiences you can go through...but I didn...
    tuyetmeo tuyetmeo 22-25, F Apr 7

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    So last night i was swimming some laps in the pool, then i heard my cell phone go off, so i got out of the water and covered up with my towel, and went to see who was calling me...
    kimheart1992 kimheart1992 22-25, F 1 Response Apr 17

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    I was home alone today and depressed about life.I heard cutting helps people who are depressed.So I got a new razor and cut my upper arm 5 times.This is when I realized my...
    ironpack ironpack 13-15, M 2 Responses Mar 30

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    That I work so hard but never have money to enjoy myself. It was casual observation and I thought I played it off when she bought so much and the only thing I could afford was a...
    lucialulu lucialulu 22-25, F 2 Responses Apr 4

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    I remember when I was happy 2 years ago but I was so caught up in someone who didn't care about me and now lost the person who did :(
    mzgirl mzgirl 22-25, F 1 Response 2 days ago

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    I've thought long and hard about my first time. I want it to be beautiful. Not romance film beautiful or storybook beautiful. My beautiful. I want to have it with someone I would...
    becki1 becki1 13-15, F 1 Response Apr 7

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    I wish I wasn't attractive to girls. I feel like my depression comes from desperately wanting a girlfriend. I feel like I can have a better life not worrying about having a...
    ForeverALoser ForeverALoser 22-25, M Apr 8

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    I was 14 at the time and was going to be home alone all day. My mother had this beautiful red nightgown hanging in the bathroom. It was soft and silky. I tried it on and it felt so...
    Stephaniegirl226 Stephaniegirl226 36-40, M 3 Responses Apr 1

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    This happened when I was in the fourth grade. We had our traditional new year festival. It was a only boys school and I was one of those in my class chosen to dress as a girl for...
    Nilooshi Nilooshi 26-30 1 Response 16 hrs ago

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    As a sub, I had to do as i was told. She enjoyed seeing me dressed as a girl. I wasn't sure at first but soon I began to feel good because i know she was pleased with me and i...
    Justwill39 Justwill39 26-30, M 6 Responses Apr 1

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    I remember it and i am a guy. it was my first child at about 4 months old boy did it hurt from cuddle to excruciating pain in 2 seconds flat. boy I don't know how you girls do that...
    peefun2528 peefun2528 56-60, M Apr 10

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    I was 16 and on vacation in the beautiful city of Morelia, Mexico. I was invited to a New Years wedding and was offered drinks everywhere I walked to. Who can say no to free drinks...
    adriit adriit 18-21, F Apr 17

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    I was inside of a car and i was telling a person i new not to smoke weed with me inside. And well, because i know she didn't care weather it was a ****** up plan or not who knows...
    Autumnflowers Autumnflowers 18-21, F 1 Response 3 days ago

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    i remember when i first started wearing pantyhose . i even went further and started to wear panties and skirts as well sometimes wearing makeup also it was a great feeling and my...
    palerider002 palerider002 51-55, M Apr 9

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    I was in school pre-k I remember heading out with my class. We were heading out outside. I didn't know but today I do lol. My teacher rushed us out the room. If you didn't have...
    lorrena19 lorrena19 18-21, F 3 Responses 5 days ago

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