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I Remember My 1st Time Dressed Up As A Girl

Personal Stories, Advice, and Support 331 People

    That First Feeling

    I've been crossdressing in some form ever since I tried on panties and pantyhose. I was immediately fascinated by the look and feel of them on my legs. After that, I would wear my moms or sister’s panties and pantyhose whenever I could. The first time I came, I was wearing my...
    pantiescouple pantiescouple
    Jul 19, 2010


    My first time dressed as a girl was for Halloween. It was the early seventies, and my Mom and my aunt decided that they would dress my cousin and I up as girls for Halloween. We both wore bodysuits, pantyhose, miniskirts, go go boots, and wigs -- we were adorable! I was eleven...
    driver88 driver88
    46-50, M
    3 Responses Dec 13, 2010

    The Very First Time

    I suppose I was about 10 years old and wondered what it would be like to wear my mum's clothes. I locked myself in the bathroom and opened the washing hamper and there were all her used clothes waiting to be washed. I helped myself to some panties, a bra, a pair of tights and a...
    LouisaTV LouisaTV
    56-60, M
    Oct 1, 2013

    Long Time Ago, But Still Remember Every Detail

    My first time was when I was 14, "cat-sitting" for a neighbour. They where on holiday, I went around and let myself into their house. They had two kids, one was a girl the same age as myself. I went straight to her room, drew the curtains and started to have a good root...
    abscater abscater
    46-50, M
    Mar 27, 2010

    First Time Passing

    I don't remember my first time putting on girls clothes; I started at a very young age and it has always been an integral part of my life. But, I do remember the first time I got completely dressed and made up, new wig etc. wearing my favourite perfume and realized that I could...
    RoseViolet RoseViolet
    46-50, F
    1 Response Jul 10, 2010

    A World Of Fun, Not Fantasy

    My love of cross dressing began when I was 12, I was left alone for the day because my parents were at work and I was on a school holiday. I had no intention of doing it, but when I was doing my chores I came across the laundry basket. I opened it to get the washing and put it...
    lejjie lejjie
    18-21, T
    4 Responses Feb 15, 2010

    Older Sister

    I was 10 years old and remember it being a snow day from school.Mom hadnt had a chance to do laundry in about a week so I was kinda running short on clean cloths.Having an older sister mom just decided it would be ok to dress me in some of heres that day)INCLUDING UNDERWEAR )my...
    bfbb19 bfbb19
    46-50, M
    1 Response Dec 7, 2011

    A Birthday To Remember

    From the age of 6 I knew instinctively that I wanted to be a girl. That’s when I started asking my mother questions such as why I couldn’t wear dresses like her and why I couldn’t be like my mommy, etc. I just can’t explain why I wanted to be a girl; I just knew that I...
    betty3100 betty3100
    51-55, T
    1 Response Dec 9, 2012

    Dressed As A Girl

    the girl next door was 16 when i was 13 and she got me to dress up for the first time!first had me in a dress she was making just could not stop my **** from tenting it!She said it was not a **** but only a sissyclitty since it was too small to **** her she gave my a hand job and...
    mandiejune mandiejune
    51-55, M
    Sep 3, 2010

    Baby Mandy

    My adventures in cross-dressing began at a very young age. My earliest memory is of being around 6 years old and the older girls in the street would play at being mums with their dolly’s. One day I was in a back garden playing happily and wanting to be part of their group, but...
    spankmandy spankmandy
    41-45, M
    1 Response Nov 4, 2011

    My First

    Don’t remember all the details; I was around 5 or 6 years old. We lived in small town, knew all the neighbors. Over one summer, the older lady that lived across the street, had her grandson come spend his vacation. He was around 11 or 12, much bigger than me, blonde hair, blue...
    Bambiluvs Bambiluvs
    41-45, M
    1 Response Sep 9, 2010

    The First But Never The Last

    Well it all started really young. I don't quite remember the very first time fully dressing up as a girl, because at the age of 5 I was taking my mothers pantyhose and putting them on. Later as i got a little older, around 8 to 12 is when I would then finally get the chance to...
    deleted deleted
    Jul 13, 2010

    Very Young

    For holloween my mom dressed me up as a girl when I was 6yrs old. At first I didn't like it but after she showed me off to a lot of people and they all looked under my dress and held me I wanted to dress like that every holloween.
    SissyTony SissyTony
    61-65, M
    2 Responses Mar 8, 2010

    For Fun And Laughs

    When i was 6th grade my brother decided we would put on a show for the family.  We went into my parents room and there was some of my sister's clothes and my mom's.  My brother informed me would dress up and do a song like girls do.  We both dressed quickly and...
    Biraninpink Biraninpink
    41-45, M
    2 Responses Apr 9, 2010

    Was 13

    This is about the first time I fully dressed as a girl not just panties and bra full thing , so I have been wearing panties for 2 weeks and decided to see what other femm clothes felt like so I found a nice tank top purple , and some tight girls jeans I put on a red thong and a...
    mazzz77 mazzz77
    18-21, M
    2 Responses Nov 10, 2010

    My First Time Fully Dressed

    I have always had a fantasy about fully dressing in female clothes, but never had the chance until I was 17, my parents were going away for the weekend and taking my sisters with them, I had lied and told my mom, that I had to work that weekend, so I stayed home. I knew that...
    mistresscathy mistresscathy
    46-50, T
    4 Responses Apr 27, 2010

    First Time Outside - Dressed.

    I can remember like it was yesterday. I was about 15 and in the house alone one evening, my younger sister and parents were going to be out for hours.  It was dark and snowing lightly and I lived in a peacful neighbourhood so it was quiet outside with no...
    teather teather
    7 Responses Feb 21, 2010
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