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I Am a Life-long Crossdresser

Personal Stories, Advice, and Support 1,059 People

    I started at about 10 years old,

    trying on my Mother's lingerie and stockings and I liked doing it, then I started wearing a satin nightdress to bed and like that as well.
    timothysknickers timothysknickers
    26-30, M
    1 Response May 23, 2014

    My Story

    I started fully cross dressing at the age of 23 after wearing tights from the age of about 14/15, I am now 54 & cross dress all the time when I am in doors
    xdpaul xdpaul
    56-60, M
    1 Response Jun 10, 2011

    The First Time That I Dressed.

    My parents told me that they were going to a show of some kind and would be away over night (I was 6 y/o at the time). They told me that the lady across the street was going to keep an eye on me and to go to her house to talk to her. I went across the street and talked to her...
    sherrynpantyhose2k4 sherrynpantyhose2k4
    51-55, T
    Mar 19, 2011

    My Journey Into Crossdressing!!!

    As most I started out at an early age, trying on Mom's or Sister's bras and panties. I was 8 or 9 when I started and now I am almost 61 and still like to dress up. I don't dress completely much any more, but I do under dress everyday, bra and panties, sometimes pantyhose...
    davis36a davis36a
    1 Response Nov 21, 2011

    I started wearing mascara in my late teens

    and it progressed to more eye makeup, continuing until I was putting my face on almost everyday. Living at home allowed my meager pay check to start buying my own cosmetics. My girlfriend, later wife, liked me with makeup on and my mom was thrilled to have a somewhat daughter, I...
    CdKimmi CdKimmi
    66-70, M
    2 Responses Apr 8, 2014

    I Love To Crossdress As A Sissy Baby Girl And Womens Clothing

    I have alsways like to crossdress as a sissy baby girl and i also love to wear dressess and bras pantyhose i have never dressed up all the way but i have dressed most of the way i especially like it when i am wearing my diapers ubder my dress but i have never been seen in...
    babyjenny67 babyjenny67
    41-45, M
    1 Response Sep 11, 2010

    The Spark

    Looking back it is easy to see the moment in my personal time line that sparked the now raging fire burning in my soul as a cross dressing sissy. I was a young boy and my Dad had a collection of **** movies stashed away in a file cabinet in his home office. I was home alone and...
    TonyaTV TonyaTV
    41-45, T
    1 Response May 20, 2011

    About Me And Dressing

    I have a hard time with the "tag" as crossdresser.  I am just a person who likes to wear clothes designed for other sex.  Women can wear any type of clothes without prejudice, men on the other hand are outcasts for liking to wear women clothes.  I enjoy silk and satin just...
    cdsparky cdsparky
    70+, T
    5 Responses Oct 17, 2012

    Maybe Not Life-long

    I discovered lingerie when I was a horny teenage going through puberty.Even though I enjoyed looking at naked women, I really loved looking at women wearing lingerie. It all started when I was a kid and I would look through Christmas catalogs and I would spend as much time...
    happilymarriedguy happilymarriedguy
    51-55, M
    1 Response Apr 15, 2012

    You Lucky Girl, You !

    You Lucky Girl, You ! I think one of the most important things that I need to do here, and in general, is to talk to others like me, crossdressers, transvestites, sissies, etc. Alright, so you already know you are not alone. Far from it. But, you still feel guilt, shame...
    CherrySissy CherrySissy
    46-50, T
    1 Response Apr 3, 2009

    All My Life

    I can never remember not wanting to cross dress, having two older sisters meant that there were plenty of girl clothes around and I could not resist trying them on. Dressing in their clothes became a secret habit, like many of us trying on sisters clothes was just the start. I...
    wetrev wetrev
    46-50, M
    1 Response Apr 3, 2013

    Moon, Prism, Power!!

    It has been quite a progression since I was 7 or 8 years old. First it was pantyhose, and then sneaking in, sometimes while mom was sleeping, and grabbing lingerie out of mom's drawers and then later wearing mom's or sis's dresses when nobody was around. At first the thrill was...
    iwearsilkiesman iwearsilkiesman
    56-60, M
    1 Response Aug 14, 2011

    Many Years

    I've been cross dressing since the age of 4. It felt natural to dress how I saw myself. Unfortunately I was born in an era where such feelings were not acceptable at all. You were forced to be what you appeared to be.I have cross dressed all my life. It has been an outlet to...
    Becnme Becnme
    56-60, F
    4 Responses Jun 5, 2010

    I'm a Life-long Crossdresser

    A long time ago, I started writing down my recollections of how all my love of all things feminine got started and the influences that formed my personality. I started wearing my mom's bra, nylon panties, garterbelt and stockings early in my childhood, most likely when I was...
    bobbieanne bobbieanne
    4 Responses Aug 6, 2008

    Caught By Older Sister

    By best friend when I was a boy was a girl on my street.  She was two years older, bigger than me and somewhat dominant.  We played “doctor” a lot and though I didn’t know or realize it at the time, the feelings and excitement made me highly sexual...
    TBurke99 TBurke99
    51-55, M
    Sep 10, 2009

    My Mother In Law

    The first time my mother in law noticed something different:do you shave your legs.My answer:sometimes. She is now almost 90 years old but still a lady and she wants to be treated that way. My wife told her about my habit dressing in womanclothes and she wanted to see me that way...
    snelveld snelveld
    61-65, T
    Jul 10, 2012

    Cross Dresser

    started when i was 13 putting on silk panties`from my mother's panty draw and getting fully dressed by girl next door!!i was hooked on being life long crossdresser!still keep my body shaved and dress daily!always wear panties and hose even at work!!
    mandiejune mandiejune
    51-55, M
    Jan 31, 2010

    I Knew That I Had Been Caught.

    When I remembered that my Moms clothes were under my mattress I went to my room, reached under the mattress and felt a bunch of flat packages but no clothes. I pulled out all of the packages in panic mode I didn't notice what they were. I had to find my Moms clothes. They...
    sherrynpantyhose2k4 sherrynpantyhose2k4
    51-55, T
    17 Responses Mar 19, 2011

    Dressing For Wife

    When I met my wife she liked the idea of me dressing up in her clothes. I decided to surprise her and dressed up in some of her clothes one night before she came home from work. When she walked in the door, I had on one of her dresses, some pantyhose a bra with water filled...
    pantiescouple pantiescouple
    2 Responses Jul 19, 2010

    Two Aspects

    Like many, I began crossdressing in childhood with some of my mother's things - a girdle, hose, a leotard. As I got older I built a collection of panties and other garments that I would find along the roadside, wash, and then wear. (For some reason I regularly found panties in...
    MiltT MiltT
    56-60, M
    Aug 20, 2013

    Born This Way

    I can remember wanting dress in girls clothes at about 5 years old. I can remember trying on my cousins panties and really enjoying the way I felt. It just seemed natural. I didn't feel I was doing anything wrong. I didn't really start until I was about 11. I woke up early one...
    randalljones randalljones
    41-45, T
    2 Responses Jan 11, 2010
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