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Thread: How did you crossdress when you were 4 or 5?

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  1. #1
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    How did you crossdress when you were 4 or 5?

    There's a thread about self acceptance, and many responses say that they started crossdressing at age 4 or 5.

    What did that look like?

    I started dressing when I was about 12. I don't really remember how old I was, but I was old enough to stay home alone. It was during those alone times that I started trying on some of my mother's panties, girdles, bras and stockings. And, everything I tried on fit pretty well.

    I don't know what would have happened if I tried to crossdress when I was 5. Nothing would have fit and it just wouldn't have felt right.

    Discuss.

  2. #2
    Exploring NEPA now Cheryl T's Avatar
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    Well for me it began one day with my curiosity and a pair of my mom's nylon panties.
    I wondered why mine and my dad's were these cotton things and hers were so different (saw them in the laundry). One day I decided to try them on and I just loved how they felt. Something in me clicked and from then on I would try them whenever I could. After a while I tried her bra. Again so different from anything else. It just felt magical. To this day they are my favorite feminine items.
    A few years later I wore her dress and tried her high heels and you know where that brought me.
    It was never about how it fit, but how it felt and how it made me feel inside.
    I don't wear women's clothes, I wear MY clothes !

  3. #3
    Silver Member NancySue's Avatar
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    I believe I was around 6, when next door neighbor sisters, one rainy day invited me to play games which turned into dress up. Initially, I had no interest, until they coaxed me to put nylons on. BAM..it was like a lightning strike. I?ve never forgotten it. Then the journey began as I invaded Mom?s hose, girdle, etc. At that time, not much interest in anything else, but that changed. Now, daily, automatic, panties, hose and bra, skirt, shorts, top and flats with a flit of my favorite perfume, a touch of makeup and flats. It makes my day.

  4. #4
    Silver Member Kris Burton's Avatar
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    I like to think I did not begin to crossdress until well into adulthood. I do remember clomping around in my mothers high heels when I was about 5. She was good about it, she just said put them away when you're done like any of my toys. Some have said that was my first experience, but I'm not so sure since I also enjoyed clomping around in my father's steel toed work boots.
    www.flickr.com/people/194195593@N05/

  5. #5
    Member RoseReve's Avatar
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    Hello,
    it all began for me around 6 to 8 years old, when I was dying to see my mother go out of the house for a few hours and I would rush into my parents' bedroom and put on her panties, pantyhose, bra, shirts, skirts, rocks, make up, jewels...and I was so happy.

  6. #6
    Senior Member Glenda58's Avatar
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    My neighborhood was all girls when I was 3 to 6 years old. And they would have tea parties with no boys aloud. I cried that I wanted to play so the older girls would dress me up in their sister's cloths. After that all I wanted was to be a girl. And now I'm getting my wish.
    GLENDA
    I FEEL LIKE A WOMAN

  7. #7
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    My first memory of trying on feminine undergarments was maybe at age 6 or 7. It was our neighbors brassiere. I don?t know the size but she was well endowed.

  8. #8
    Trans woman BiancaEstrella's Avatar
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    I had a cousin my same age whose shoes were 1 size smaller than mine, and I was heartbroken over it. I wore my grandmother's too-big-for-me shoes around.

    At age 8 there was an aunt whose shoes I fit perfectly and I loved "organizing" her shoe closet (trying them all on).
    "Be yourself; everyone else is already taken."
    Oscar Wilde

  9. #9
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    I started with mom's bra and heels. That is the earliest I remember. The only time i was ever caught I was around 8 or 9. I was wearing my sister's panties, white with yellow ducks. I know I was wearing nylons and dresses by 10 or 11.
    Sara

  10. #10
    Platinum Member alwayshave's Avatar
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    Steffi, my mother stored much of her overflow clothing and lingerie in one of the closets in my bedroom. One of these closets also lead to the attic. I had the chance to try on her lingerie and clothes. I just loved the way the lingerie felt. I was hooked.
    Please call me Jamie, I always_have crossdressed, I always will, "alwayshave".

  11. #11
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    Around 4 or 5 with mom's Hose & Heels,
    Having my ears triple pierced is AWESOME, ~~......

    I can explain it to you, But I can't comprehend it for you !

    If at first you don't succeed, Then Skydiving isn't for you.

    Be careful what you wish for, Once you ring a bell , you just can't Un-Ring it !! !!

  12. #12
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    Around 6 I think. When my mother was working (father was a drunk and never wanted me around anyway) I would stay at my Aunts (moms sister). My cousin (female) and I would play "dress-up". My Aunt was divorced so no adult male clothing. I became obsessed with her slips, still have memories of wearing half slips over my tighty whities. Not clear why then but when I got older,early teens, I "rediscovered" them.... the silky smooth feeling on my skin..... it just went from there, expanding out into other clothing types. Relatives or (shamefully) the neighbor's clothes lines until I started buying my own.
    Last edited by Jeri Rene; 09-28-2024 at 04:37 PM.

  13. #13
    Senior Member Fiona_44's Avatar
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    I was around 9 or 10 when I first got interested in women's underthings including girdles and slips. And I have had that interest all my life.
    "Care about what other people think of you and you will always be their prisoner" - Lao Tzu

  14. #14
    Platinum Member kimdl93's Avatar
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    I wore my older sisters slips one a few occasions. I was very cautious, because I had already gotten the impression that this was not allowed!
    O wad some Pow'r the giftie gie us
    To see oursels as ithers see us!

  15. #15
    Aspiring Member Michaela Jane's Avatar
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    I don't believe that I ever did crossdress at that age. As the eldest of a family of five, the only female was my Mum, it actually never crossed my mind to try on her stuff.
    I knowingly tried on my first ever panties at age 52, when I was looking for a thong to replace my old black one. All the mens stores sold gross looking thongs & I found a nice one in the womens section. Wifey said I could get it and the rest is history.

  16. #16
    Gold Member bridget thronton's Avatar
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    Probably only high heels at 4 or 5

  17. #17
    Aspiring Member Brynna M's Avatar
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    My oldest crossdressing memory is playing dress up with the girls in daycare when I would have been in prek or kindergarten. I remember trying on my mother's clothes where in the house we lived in from 3rd grade. I think it's interesting that among the flashes memory I have from very young are instances of CDing with favorite family vacations etc.

  18. #18
    Aspiring Member Bea_'s Avatar
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    I have vague memories of my older sister and one of her friends dressing me up as a girl when I was about five years old. It really had no influence on me to continue. I remember being mesmerized by all the bras in the sears catalog but not as something for me to wear. it wasn't sexual but there was major fascination.

    Other than a couple of random opportunities to try feminine items out of curiosity, I had no real inclination to dress until my fifties after some major trauma. Not sure if the dressing would have taken place without the trauma.
    To be loved but not known is comforting but superficial. To be known and not loved is our greatest fear. But to be fully known and truly loved is, well, a lot like being loved by God. It is what we need more than anything. ~ Timothy Keller

  19. #19
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    When I was five years old, living with my grandparents, I was an inquisitive little fellow who would ask just about any question without thinking much. I liked to swim but the brief nature of little guys swim trunks left a lot exposed. I remember asking my aunt, who was age ten at the time, why I could not wear something more covering, as she did. Because you are a boy and you wear what boys wear was the only answer I could get.

    There was a pair of fraternal twins my age at the church. I hung around with the twin boy. I remember his twin sister and the beautiful dresses that she wore, again asking my aunt why I could not look so pretty. Same answer.

    The pink fog dissipated for a few years, though I read the girls sections of the big catalogs that my family received. I knew my size though we had no money to get clothes, new or otherwise. I wore the castoffs of several of my slightly older cousins, all boys. Without girl relatives in that age range, there was no opportunity for raiding the clothes bins.

    At age nine, the pink fog returned. I was back with my nuclear family by then. I asked my mother to dress me in a floor length skirt, an off the shoulder blouse, and a kerchief to cover my hair. She dutifully did as I asked. My sister two years younger accepted me enthusiastically. I marched in a Halloween parade dressed that way and went trick or treating with friends and family with little trouble. Even at that age, I could compartmentalize well and I ignored any comments. Nothing further came of it.

    It was age 12 when the pink fog returned. I assembled a stash that I kept for my teenage years until joining the Army at age 17.

  20. #20
    Silver Member Marcia Blue's Avatar
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    At the age of five, when left alone. For very short periods. I tried on my mom's clothes and her lipstick. I know I tried on her bra and tops. All that were too large. The lipstick I liked the most.
    Marcia (LOVES) Blue

  21. #21
    Senior Member Christie ann's Avatar
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    I remember putting on lipstick while quite young. I also remember my dad’s reaction

  22. #22
    Aspiring Member
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    My sister's petticoat was like a Siren calling me into a trap. I haven't escaped yet.

  23. #23
    Member Richelle423's Avatar
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    I remember being 5 or 6 years old and walking around the house with a towel wrapped around my waist with a clothes pin to hold it wearing it like a skirt.

  24. #24
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    We are all different! I didn't have a sister and didn't have any interest in wearing female clothes until I entered my teens - by which time some of my mother's things fitted reasonably well. Had i tried wearing those hings when much younger, they would have fallen straight down to the floor!

  25. #25
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    I was about four, and it was the days when women wore furs, and girdles, and wigs.

    Like it was yesterday, I vividly recall looking out the window, my family was in the front yard. My Mother's fur stole was on a chair. It was left there from when she had come home the night before. It smelled like perfume and cigarette smoke. I was overcome by a strong desire to wrap it around my shoulders, and I did...I remember its lining felt cool, as it sat on my skin. My next dressing memory was reaching into my Mother's dresser, [How was I alone at that age? Was I? I don't remember] and trying on a pair of her bras and panties...I recall placing her fake pearls around my neck, and liking the look so much, I then ran to her closet where I tried on one of her many frosted blonde wigs. Young as I was, I was driven to wear her lipstick. I picked a shiny golden tube of coral pink, a popular color back in the day, I remember my hand shaking as I nervously traced my lips as neatly as I could. I walked around the upstairs of our home. Staring at myself in every mirror we owned. I loved what I looked like...And, to be honest, today, when I dress and give that final shake of my wig, I still see that same young woman looking back at me today.

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