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I Have Been Dressing Since Childhood

Personal Stories, Advice, and Support 1,806 People

    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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    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 May 2, 2012

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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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    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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    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 5 Responses Dec 1, 2013

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    Pretty Dresses And Petticoats

    So have I. Started when I was 5-----nylon panties with lace trim------petticoats with a lacy nylon half slip underneath. The pretty pastel nylon half slip helps to keep the pretty petticoats from scratching
    carolannP carolannP 61-65, M 5 Responses Apr 28, 2011

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    It A Toss Up

    Growing up with 3 sisters or the Flip Willson show I found the joy of dressing up I don't know it was just something I had to try to stand in front of a mirror and say WATCH SUCKER !! just like Greadin and then put on a another dress and pair of shoes . It was the 70s go-go boots...
    notech64 notech64 41-45, M 4 Responses Jan 5, 2010

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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 24 Responses Dec 5, 2011

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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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    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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    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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    Me Vestia De Menina Escondido Desde 5 Anos

    desde meus 5 anos sempre colocava as calcinhas de minha mãe mas sempre fui esperto ate que um dia ele me pegou com um vestido dela ,  me chingol muito, mas en fim o tempo passou a eu continuava me vestindo de menina, ate que um dia ao 10 anos tinha uma prima da mesma idade que...
    josemouraa josemouraa 22-25, M Jun 10, 2011

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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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    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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    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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    I Was Paid To Be A Little Girl; And It Was A Fun Adventure!

     My Life as a Young Boy (Read my 50 plus 'ventures on EP under I LOVED DRESSING LIKE A LITTLE GIRL, and follow me through my wonderful world as a young boy.)         About age six I began a career as a child model, modeling for a local agency with many national accounts...
    theBillyandBudBear theBillyandBudBear 66-70, M 2 Responses Jan 26, 2011

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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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    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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    Yup,since Childhood

    Since around 8 years old.Nothing more to add.
    cindyloulove cindyloulove 56-60, M Jan 28, 2012

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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 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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    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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    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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    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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    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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    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 26-30, T Sep 24, 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 just checked my last story I posted and its almost been a year sense I have been on this site! Maybe its a sign I shouldn't work two jobs?
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    It's My Fault - I couldn't help it, I became a control freak and I tried controlling my friend's character and tried making them do what I wanted. It's just well, i'm a...
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    This past months were not easy at all. I wanted to die so many times. Inside I felt empty sometimes sad. I knew that my problem was because my heart was torn between what was and...
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    It's hard to believe, but I have been. Though not in my present incarnation. Like some old-timers, I've deleted my profile and returned. Several times. Another old-timer that I...
    samedeepwater samedeepwater 46-50, M 2 Responses Apr 1

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    Cause my mums in hospital I been stayin with my friend Keiran an his family an they got a cottage in Wales so we been there since start of the week ((: Monday was nice so we had a...
    HannahRb1999 HannahRb1999 18-21, F 1 Response a week ago

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    I had no crush on any guy ever until one of my close friends (Who we will call Close friend) said "Hay 'My name' (A guy who we will call Guy #1) likes you" and my whole heart...
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    I was dating a girl that I have been friends with and known since elementary school. We even went to the same college. We didn't date until the end of last year and it was great...
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    mermaid27 mermaid27 36-40 Apr 3

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    Just recently i moved up the street from my best friend that i have been friends with since i was 5 and things were going good until he started talking to my girlfriend and started...
    niceguy223 niceguy223 13-15, M 2 Responses Apr 6

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    I have been skinny dipping since my early college days. I do enjoy being a nudist today naked with friends but not with my children.
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    Don't you hate it when you hear yourself talking. Like when someone records your voice..I think I sound ugly only cause I'm not used to hearing myself, since we all sound different...
    conzy112 conzy112 18-21, F 2 Responses 2 days ago

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    My husband and I have been married for 6 weeks now. I've loved him for 19 years though. Still just as much as I did when we met. He's been an addict his entire adult life. I...
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    Every day, I wonder how different things would have been if I never got into that car accident that night, and you were still here. I wonder if I would have been a good mother to...
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    when me and my bff where breaking up cuz her mom found out we had been watchingporn 2gther and i was s*xting guys i met on omegle after my breakup she wouldn't let us hang anymore...
    casssss casssss 13-15, F 3 Responses Apr 2

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    I got my first job as an artist's model as a 19 year old and it was all about the money. Soon I found out how much I loved being a model. I am comfortable nude, but also really...
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