I Have Been Dressing Since Childhood

Personal Stories, Advice, and Support 2,067 People

    Crossdressing

    I've been cross dressing since as far as I can remember. Mostly bra and panties, furtively, while my parents were away or on some errand. After I left home, I dressed off and on, mostly as an aid to ************. Lately, I've been doing the while magilla, makeup, wig, femme...
    EllieMayClampett EllieMayClampett
    66-70
    Oct 26, 2013

    Young Crossdressers

    This experience is not about me, but about two different girls I've had the pleasure of seeing during my lifetime. The first was back around 1980 or so. I was at a suburban mall near San Francisco in boy mode. As I was entering the complex, I noticed a woman walking with a...
    dondonna415 dondonna415
    51-55, M
    3 Responses Oct 27, 2011

    That'S The Way I Was Brought Up

    I've worn feminine clothes since I was born. I had three sisters and mother who just treated me as the baby sister and I still am now and I'm 70. I'll obviously never change and have only had a few negative times. My wife of 32 years wouldn't have it any other way. I don't go out...
    deleted deleted
    26-30
    1 Response Feb 18, 2013

    Guilty, Your Honour!

    The classic tale runs something like person gets buy in adult life until mid aged then discovers the joys of dressing younger or even changing presenting gender. That wasn't true for me because I've always had a younger than my chronological age bit going on in my life like I was...
    deleted deleted
    26-30
    1 Response Jul 26, 2012

        I started dressing in my

    mothers clothes when I was 10. To this day I'm not sure why I did it, but one afternoon in the summer I was home alone for a couple of hours, bored or curious I decided to dress up and put on a bra, panties, tights and a long sleeve leotard. The feeling of having my body encased...
    MichelleTiedup MichelleTiedup
    61-65, M
    2 Responses Aug 28, 2015

    How It Started...

    Used to go to cousins during the summer. We were close, she was about my size. I'd stay at the house while they worked a few hours and .... It all started with SHOES, still love shoes...and then swim suits, then clothes.... oh I still love wearing sexy shoes! I was 15 or 16. From...
    MandiLi MandiLi
    31-35, T
    2 Responses Dec 10, 2012

    Sort Of.

    If you, a) count panties as "dressing," and b) count high school as childhood. I started wearing panties in high school, tried on some skirts in college and didn't really start dressing until after I was married and had a job.
    SomeguyinUT SomeguyinUT
    31-35
    2 Responses Nov 23, 2009

    I'm a 15 year old sissyboy

    who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels and definetly make up and I'm secretly attracted to masculine tough hairy men 5 years of me dressing up Yay and many more to...
    deleted deleted
    26-30
    Feb 3

    My First Time

    I guess I was about 8, my sisters where outside playing and I tried on one my older sisters party dress. I loved the feel of it for all of the 10 minutes or so I had it on, I panicked when the zipper got stuck taking it off but I eventually managed to get it off before they came...
    wendym99x wendym99x
    61-65
    3 Responses Feb 15, 2013

    I Started Wearing Mums Panties At 6

    I was only 6 the very first time i tried on my mums nylon panties & could not believe how good they felt on my young hairless skin. Also just loved the aroma of my mum on them too. I wore them to bed almost every night & sometimes to school & at play under my boy clothes. I...
    deleted deleted
    26-30
    4 Responses Nov 27, 2012

    I Have Been Transgender My Whole Life

    I was born transgender, so therefore a crossdresser to wear MY clothes. I was aware of it around age 5 and although didn't understand it, I was wearing my Mother's high heels and dresses and jewelry ... playing dress up. Even through my teens when I dress as a girl, the whole...
    Josie06 Josie06
    56-60, F
    3 Responses Mar 19, 2012

    First Time.

    The first time to have a **** in my mouth was at 14 it was my own I was skinning enough to bend my body to get part of it in my mouth,I loved it I did not think I was queer I did it often after that ,it felt so good feeling it between my lips with my sisters panties hanging on my...
    rosser9 rosser9
    26-30, M
    2 Responses Oct 20, 2013

    At School

    used to wear tights and a bra under my uniform
    christinemelody christinemelody
    56-60, T
    3 Responses Sep 1, 2012

    I was about 5 years old

    when I put on my first dress. I remember it vividly. It was one of my sister's sun dresses with crisscross straps in the back holding up the skirt and a bib front. I didn't know what I was doing very well since I got tangled up in the straps and panic set in and I cried. My...
    phylisst phylisst
    70+, M
    3 Responses Oct 18, 2015

    It Just Felt Right.

    It all started when I was around the age of 5 years old. My parents had bought our family a swimming pool. We were all excited! About a week later, I went looking for my swimming shorts but couldn't find them. My mom invited my friends and family over to the house so I was...
    deleted deleted
    26-30
    11 Responses Apr 11, 2013

    I To Have Been Dressing Since Childhood

    Mine started when I was 10 at a friends house. We were playing house and I was going to be there sister.  I was asked to put on a black nightie and wear it while playing.  Well I felt a strange feeling like this is meant to be.  Every time we played house that was my outfit...
    deleted deleted
    26-30
    1 Response May 7, 2013

    Desires Can Go Farther Back Than You Think

    I was thinking back today about my earliest experiences. The one that is most vivid in my mind is when I was about 9 years old and I got my first chance to play dress-up with my sister. That was the most thrilling experience I ever had and I never stopped from that day forward. I...
    silkydrawers silkydrawers
    46-50
    3 Responses Mar 8, 2013

    How I Became A Crossdresser

    when i was about 8 my sister used to always have sleepovers and i always hungout with her and would sleep in her room one night one of her friends got all upset that a boy was going to sleep in the same room as her and then my sister said then lets make him a girl then they put...
    JulieCakes JulieCakes
    16-17, M
    3 Responses May 2, 2012

    since before the 6th grade.

    as Long as I can remember.
    Therealjason Therealjason
    31-35, F
    1 Response Mar 16, 2015

    Why

    I was born in 1940 and I can remember as early as around five years oil that I wanted to be a girl and wanted to dress in girls clothing. At that time I could only dream about it but wasn't old enough to do anything about it. I didn't have any older sisters to "borrow" their...
    VivianV VivianV
    70+, T
    1 Response Jul 24, 2012

    Started With Panties!

    It all started when I was around four or five years old, when I noticed and couldn't keep my thoughts off my older sisters panties. I had your typical boy underwear of the time, boring old "tighty whiteies". She had these very simple, but very cute satin panties, and what really...
    CHRISSY28 CHRISSY28
    46-50, T
    1 Response Jul 16, 2013

    My Adolescent Years

    My previous writing was how I started dressing when I was 6 years old. My adolescent years through my teenage years were very trying also. Throughout my adolescent years I learned that getting caught dressing up meant severe ridicule and punishment. I learned to be careful and as...
    francenemarch francenemarch
    66-70, F
    9 Responses Feb 14, 2013

    My Teen Years

    My teen years were mostly turmoil. Having been what I considered brainwashed to be a macho boy and grow up to make babies had many thoughts going through my head. I tried to be a “boy” by playing baseball and hanging around with other boys. Even though I wasn’t dressing it...
    francenemarch francenemarch
    66-70, F
    3 Responses Feb 17, 2013

    I have been dressing new born baby clothing ever

    since I was 12 years old. I have dressed this way 24-7 ever since I was 18 publicly. It just feels right and natural. Over the past 2 years there have been several tv shows where other adult babies have come out and I find a whole new attitude where I am being welcomed for...
    timmyp3 timmyp3
    46-50, M
    Dec 2, 2013

    Hello,my name is jacob

    but i like to go by zoey. I have spent the last seventeen years of my life alone because I am a girly-boy. Now I have the Internet and sites like this. i am now seeking help from someone who lives near me. i live in Virginia and am looking for some one I can meet, i love EP...
    zoey764 zoey764
    18-21, T
    2 Responses Jul 23, 2014

    A big help in transforming a boy into a girl is

    the testosterone blocker cypreterone acetate. You can google it to find out more. Once the boy has his testosterone reduced he will become more feminine and well behaved.
    TeachingRespect TeachingRespect
    51-55, F
    1 Response Jun 20, 2015

    Early Memories

    When I was a little boy, may be about ten years old, I dressed the first time in clothes from my mother or my sister. I used the bathtime to lock the door and took everything out of the hamper which I liked. I put it on whenever I could. Unfortunately I never had the guts to tell...
    gretatv gretatv
    46-50, T
    2 Responses Dec 22, 2008

    My Sisters Closet

    The first time that I crossdressed, I put my sister's clothing on.  Back then, the panties were 100% nylon!  Better made as well!  My first dress was a baby pink play dress.  I hated to take it off.  I wore a training bra, nylon briefs, a full nylon slip, and her baby pink...
    OhioSissy OhioSissy
    56-60, M
    1 Response Aug 5, 2011

    First Memory.

    My earliest memory about dressing is from about the age of 3 or 4. It was bedtime and my mum was in the bathroom with my sister, who had taken her clothes off in the bedroom. I was undressed and waiting for my time in the bathroom when I noticed my sisters underwear on the floor...
    throb42 throb42
    41-45, M
    2 Responses Oct 7, 2012

    My Begining

    For me my story as a straight crossdresser began around the age of 5. I was always fascinated by tights, the way they looked on girls and me , the way they felt on my skin, and the overall hugging feeling they had on my legs. I started out with just wearing tights under my pants...
    deleted deleted
    26-30
    3 Responses Mar 14, 2012

    I Started When I Was 7

    I started dressing when I was around 7 years old. I was in my parents bedroom alone (of course) and noticed a pair of my Mom's panties and how soft they were to touch. I wondered how they would feel if I put them on, so I thought why not, I'm home by myself so I quickltook my...
    karen42 karen42
    66-70, M
    10 Responses Oct 20, 2010

    Teen Years - Meeting MY Girlfriend

    Well, I made it through high school but after reading about Christine Jorgenson and wearing out that tabloid all I could think of was getting more reading material. I got a full time job at a local car dealer in the city close to my home. (Just a side note, I love cars and I love...
    francenemarch francenemarch
    66-70, F
    7 Responses Feb 21, 2013

    I Have Been Dressing Since Childhood

    I have been dressing since childhood. When I was around 11 or 12 I remember going to my moms dresser drawer and finding her bra and panties.  Oh, it was such a wonderful feeling to put on her clothes.  I would wear her underwear for a while and put it back in her drawer. In...
    jml2000 jml2000
    61-65, M
    3 Responses Sep 14, 2012

    I can appreciate what males

    who like to cross dress experience throughout our lives. I too have been dressing since I was about 5 and find it frustrating to be a guy with a strong desire to be feminine. As I approach my more senior years I can look back and think about the few times that I wore dresses in...
    phylisst phylisst
    70+, M
    1 Response Oct 18, 2015

    I'm not sure when I first put on ladies

    underwear but I do remember being at nursery school and a boy said he had to wear his sisters panties because all his were in the wash, he showed me halfway up the climbing frame and I remember thinking how lucky he was because they were much prettier than mine and made of nylon...
    Lingerielover2110 Lingerielover2110
    56-60, M
    9 Responses Oct 14, 2014

    Hooked

    After I first tried on my mother's and sister's panties, pantyhose, and tights, I just kept sneaking back to wear them again and again. I really liked my mom's panties and pantyhose best, but the pantyhose were too big for me, even though they felt so silky, soft, and smooth. The...
    samctv10 samctv10
    36-40, M
    33 Responses Feb 7, 2012

    My Dear Cousins &Amp; Freinds

    we always wanted a niece...since age 3 my cousin babysitters and their girlfreinds dressed me in little girl clothes, but not until age 4 did i know the differance between boys and girls...and i prefered girl clothes, i loved wearing panties and a frilly dress,and hated boy stuff...
    northerngirl2 northerngirl2
    56-60, T
    2 Responses Feb 17, 2013

    I've been crossdressing

    since I was 6. I got started by playing dress up with my teenage baby sitter and her sister. Its still fun and a real turn on!!!
    Christymariegirl Christymariegirl
    51-55, M
    Dec 30, 2015

    Even Before I Can Really Remember

    I must have always had a facination with girls clothing, panties in particular. My wife was telling Mom how hard it was potty training our oldest child. Mom told her it could not be anything like training me. I would not go on the potty, but I would if I had pretty panties like...
    thisismeisthisyou thisismeisthisyou
    41-45, M
    2 Responses Feb 9, 2012

    Five Years Old

    i have been dressing since i was five years old and will be cross dressing untill i die.
    Cyclopes66 Cyclopes66
    51-55, M
    1 Response Oct 1, 2012
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