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I Have Been Dressing Since Childhood

Personal Stories, Advice, and Support 1,883 People

    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

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    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

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    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 13 Responses Apr 11, 2013

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    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

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    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

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    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

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    Back In The School Dress!

    so since my first time dressing up i had forgotten all about my sisters school dress and the feeling i got while wearing it. i was now twelve,5 years have past and suddenly i remember all about the time i wore my sisters uniform.id been left in the house alone and decide to...
    cdBethany cdBethany 22-25, M 1 Response May 2, 2010

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    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

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    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

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    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

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    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

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    I Don't Really Remember The First Time....

    As I sat here this morning in a diaphanous full nightgown with a fitted lace bodice; underneath wearing a black lace bustier with a matching thong and stockings, reading the stories of others that can date their first time....I got to thinking about the first time I slipped on a...
    meridithmichelle1020 meridithmichelle1020 56-60, T 1 Response Sep 3, 2011

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    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...
    cd4259 cd4259 51-55, M 8 Responses Nov 27, 2012

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    Getting Caught First Time Didnt Stop Me.

    hi im bethy(ben in boy mode) im 25 and have been crossdressing since the age of 7,i can remember that because i remember that the first time i tried dressing was in my sisters pink gingham school dress. id been left alone upstairs playing with my cars when for some reason i...
    cdBethany cdBethany 22-25, M 6 Responses Apr 10, 2010

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    Just Me

    I don't think my story is that much different.Yes the events may be different but the song remains the same.growing up i had 4 sisters and my favorite thing to do was play in there closet.Of course that was taboo.I would have been down to see the priest in a minute if my parents...
    eddytv eddytv 51-55, T 1 Response Apr 5, 2012

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    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...
    glasscitycd90 glasscitycd90 22-25 4 Responses Mar 14, 2012

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    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

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    Yes !

    As detailed elsewhere I just decided to wear girl's clothes from an early age, starting with mum's high heels.....only 3 1/2" high, but every potential T-Girl has to start somewhere right? Wearing dresses was easy...using lots of socks to fill out those bra's was something that...
    TVCassandraSlut TVCassandraSlut 26-30, T 2 Responses May 25, 2013

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    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...
    Joanne0chan Joanne0chan 31-35 1 Response Jul 26, 2012

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    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 1 Response Jul 23

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    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 56-60, M 5 Responses Sep 14, 2012

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    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 51-55, M 2 Responses Aug 5, 2011

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    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

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    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 35 Responses Feb 7, 2012

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    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

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    At School

    used to wear tights and a bra under my uniform
    christinemelody christinemelody 56-60, T 4 Responses Sep 1, 2012

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    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

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    Thought About It

    When I was young I never really thought about it much till I was 8 I saw dude were my car and say the T-girl since that day I have wounder what I feels like to be a man whom dresses as a girl it took 5 years but then I wore my firs panties since then I knew why people cross dress...
    mazzz77 mazzz77 18-21, M Aug 3, 2010

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    Early Influences

    I have seen several stories recently of childhood memories going through old clothing catalogs to look at the pictures of dresses.  For me in childhood it wasn't catalogs but TV shows (appropriate, don't you think? because TV can mean television or transvestite...)Specifically I...
    CDralph2010 CDralph2010 46-50, M 3 Responses Sep 22, 2011

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    I Love What Estrogen Has Done

    I am going to share my experience with using hormones, which had a significant effect on how other people see me. I want to be as frank as I can be about my own experience with hormones and their effect on me. I have been through the counseling process and have come away not...
    Trisha60ts Trisha60ts 61-65, T 6 Responses Dec 1, 2013

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    Early On

    Spring afternoon 2 grade pictures and a cutie sissy girl in lace and satin frilly ruffled panties soft silky tights under that wonderful dress. The playground, the first time I remember trying to look at a girls panties and dress. The first time I touched her dress. The first...
    size7satin size7satin 41-45, T Jun 18, 2011

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    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 13-15, M 2 Responses May 2, 2012

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    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 10 Responses Feb 14, 2013

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    My Beginning

    When I was a kid small towns, like the one I lived in, didn't have large department stores and subsequently when the seasonal catalogues arrived they would be read from cover to cover many times over. It was while thumbing through one of the spring issues that I first noticed the...
    JacquieTG JacquieTG 46-50, T 13 Responses May 15, 2011

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    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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    Crossdressed For Friends

    I was 7 years old we moved to a new town, I couldn't find any boys my age near our house to play with, so I hung out with my much older brother and his friends They usually did the rough house type of activity which always resulted in me running home in tears from one thing...
    keptproperty keptproperty 18-21, M 6 Responses Mar 28, 2013

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    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

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    Petticoat Your Dress

    I saw this on line at Etsy dot com. This shop has all kinds of vintage clothes for the 40's thru today's style of dresses. I'm going to get a skirt handmade similar to this dress to wear over all my pretty petticoats. Just check it out. Its exciting just to look at this one. http...
    bobbylee111 bobbylee111 36-40, T Sep 24, 2013

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    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

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    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

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    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 4 Responses Feb 17, 2013

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    Attracted To Tights

    It started for me when i was 8 or 9, i was (for some reason, still don't know why) really attracted to tights. The look, colour and feel was fascinating. It was my sisters school tights and dance tights i first wore, but also her and my cousins white school socks. It progressed...
    SaskiaIreland SaskiaIreland 31-35, M 3 Responses Jun 27, 2011

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    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 2 Responses Feb 18, 2013

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    A Decision I Made... Years Ago.

    To have and to hold from this day forward. Sept 15, 2001 on this date I informed my spouse and said "I was going to transition into a woman, many thoughts came into both of our minds as well as a flood of feelings. It was overwhelming to sift through it all and sort my...
    Trisha60ts Trisha60ts 61-65, T 3 Responses Mar 24

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    Mom , Did She Want A Daughter?

    I wonder why mom wanted me crossed dressed at home so much, could it be she wanted a daughter? It is true she had only 2 sons, she could have told dad she wanted another baby and take a chance on it being a girl, or she could cross dress me Dad might have been against...
    keptproperty keptproperty 18-21, M 2 Responses Mar 29, 2013

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    Wife's And Crossdressing

    It has always been an unhill struggle to crossdress and wish i could of done so alot more often in my life.I do find it's hard to balance relationships and crossdressing, unfortunately after telling my second wife a couple of years ago i had to decide beween her or Katharine (my...
    katharine25 katharine25 56-60, M 23 Responses Dec 5, 2011

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    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 3 Responses Dec 10, 2012

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    Related Experiences

    The day is ending and what can I say? I don't feel much better, honestly. I'm still fearful, sad and feeling the injustice over my family. I'm still trying to understand God wishes...
    Fernandotavares Fernandotavares 22-25, M Sep 4

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    So since i was little i have had depression problems,i didn't actually noticed until it got really bad in high school.I can't tell anyone in my family cause they won't actually get...
    flproblems flproblems 18-21, F 3 Responses Aug 20

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    I have always been depressed sence I could remember I always act ok and never let on how I truly feel I don't take meds for it though I probably should but I just find the fact...
    Toyx Toyx 22-25, F 1 Response Aug 27

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    the sad part is the people who are "blessed" wouldnt understand because they dont have to go through the same things you have to go through.
    unlovednbroken unlovednbroken 18-21, F Aug 25

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    I feel empty, lonely, worthless, in pain I have personified my feelings into a person that I think about and right about sometimes, tonight is an especially bad night. I saw my bf...
    Zezebabe Zezebabe 18-21, F 2 Responses Aug 31

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    I spend most of my time sitting on the internet and not leaving my house, or attending parties people invite me to. Some days I can't even dress myself. I can't leave the house...