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Thread: How did you start dressing

  1. #76
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    I was maybe 7, and my mother borrowed a dress from the girl that lived next door. Against my protestations, that and a wig she got somewhere became my Halloween outfit. At some point I remember feeling comfortable in the dress and wig and liked being pretty. As time wore on, 9 or 10 years old, I became aware that girls underwear felt better than boys underwear. When putting on my mother's underwear, I felt pretty again. Curiosity had me trying on her bras and skirts and looking at pretty me in the mirror. I've been looking for and at Heather in the mirror ever since.

  2. #77
    New Member shimmeryphantasy's Avatar
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    As far back as I can remember maybe 3 or 4 , all my earliest memories are of getting into moms and sisters drawers and putting on the soft things . Mom had a big drawer for her panties and one for her hosiery and one for all her wonderful nightgowns . When I was that little her pantyhose would cover my whole body over my head , I loved doing that . Her slips were so soft and slide over the hose and felt so good . Then I would put a nightgown over all of that and slide around in her bed rubbing the softness all over myself until I was pulsating with pleasure , I loved how it felt so much I would do it every chance I could. I loved how her slip would slide on her black panties if I turned the slip inside out so the softer side was sliding on the panties , I would always wear the nightgowns inside out so the softer side would be against my skin and I started putting on 3 or 4 nightgowns alternating layers so they would be super slippery.. It is 50yrs later and I have many nightgowns and pantyhose and wear them whenever I can.. I live in a small town so I have to keep it all in the closet but what a wonderful closet it is

  3. #78
    Senior Member Maid_Marion's Avatar
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    My wife suggested I start wearing women's clothes when it became obvious that finding age appropriate men's clothing in my size wasn't an option.
    Turns out that women's XS or size 2 clothes fit amazingly well--with a little bit of hunting I can find clothes that fit well right off the rack without any alteration!
    My waist at the time was 28 inches. With some exercise I can get it down to 25. Men's sizes start at 30.

    The first really feminine clothes I bought was VS PJs. She was OK with me wearing them, but she, like many GGs, had issues with VS because nothing sold there fit her.
    We had a talk and set boundaries.

    Marion
    Last edited by Maid_Marion; 05-26-2021 at 09:30 AM.

  4. #79
    Member DanielleCD's Avatar
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    Like many.. with my mom's stockings and then my sisters underwear.. I guess I was about 13 or 14 years old? I was so hard trying to be a boy but girlie underwear felt so different, and felt so nice and right. I spent many years confused, embarressed and hidden.

  5. #80
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    I started with Mom's stockings in the '50s. I was done for at that point. Lifetime wearer.

  6. #81
    Member Gilly68's Avatar
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    My story is the same as a lot of other girls here.

    My neighbours kids when I was seven or eight were all girls, so we would play house together. I remember me playing mum and stuffing things up my shirt to look more like our mothers.

    When I played with action figures I used to pretend that the male ones would get magically transformed into the female ones.

    First experiences of actually crossdressing was with my mum's clothes, like a lot of girls here.

    When I was old enough to stay home alone whilst my parents went shopping, so maybe 12 years old or so?

    I would go rummaging in her drawers and wardrobe, trying on bras, knickers, dresses, and my favourite thing was trying on her one piece swimsuits and stuffing socks in the bra cups.

    I even remember trying on her lipstick and trying to make a wig from her knitting wool!

    And carefully placing everything back exactly as I found it, and the worry she would notice things had been moved around

  7. #82
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    I started when I was under 10 and used to wear my moms heels and dresses to feel pretty. Then later I put socks up my shirt and pretended to be a girl I knew. That was it for me then

  8. #83
    Senior Member MargaretJ's Avatar
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    My earliest memory of cross dressing was when I was 4 or 5, and trying on my mum's open corselette with suspender hooks, and high heels. Since around that age I have been fascinated with stiletto heels and stockings, and I generally will only wear heels. I would usually only wear tights and sometimes panties till I was around 12, then I started to wear my sisters clothes. My cross dressing would come and go, but the last 12 years or so after buying my first wig and breast forms, and using make up, I am well and truly in to it now.
    "She snuck up on me from behind. You'd think women would make more noise with those big high heels, but they don't, they've got this stealth thing going..."

  9. #84
    Silver Member Maria 60's Avatar
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    I shared room with my sister and she was a slob, and I remember that morning like it was yesterday. There was a pair of pantyhose on the floor next to my bed, my sister had left the house early and I put them on and went to town with them. From then I started staying in bed later then her and just would sneak more and more things under my sheets. I could still remember the rush that morning I put on her pantyhose and a white slip, the feeling was unbelievable.

  10. #85
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    I went back and forth from a youger age ( around 6 or 7), with my mom and aunts clothes. Later I bought myself some lingerie but it never stayed. It always come in waves, sometimes i dont feel like it, other time I do. But now i am well equiped ! 😄

  11. #86
    Junior Member NewSally's Avatar
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    Similar story for me, as I began by rummaging through Mom's dresser of the laundry hamper, and trying on her pantyhose and bras on occasion when I was entering puberty. From then on it was very hit and miss, and later in life when I had girlfriends I would sneak some of their lingerie to play with. Always on the DL, though. Never had the courage to tell anyone I was dating (including my now wife) about my desires in that regard.

  12. #87
    High heeled lady GiovannaBotta's Avatar
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    I had an aunt that I stayed a lot that was a boot lover... high heeled boots mostly. Don?t know why around 8, 9 years old started wearing them while alone at her house. Then it was mom?s clothes and shoes (always the shoes) and soon makeup, dresses, clip-on earrings... and there goes 30 years!

  13. #88
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    Depends on what counts as the beginning. My earliest inklings trace back to mental images from when I was perhaps three or so, very young, remember trying on an older sisters slip, and around that time, some recollection of being teased for doing things girls did?not sure what those things were, but the message was clear. I suppressed that as much as I could into my teens. Then I spotted a younger sisters pantyhose. Then some 30 years of little more than a pantyhose fetish, with the usual denial, attempts to quit, and repeat.

    Somewhere along my mid 50s I found myself curious about venturing further - prior to that I had always assumed I just could never dress fully and presentably as a woman. I tried on a few things that belonged to my then wife?and wasn?t appalled by how I looked. I got some make up, a wig and some breast forms?and it just clicked, I could do this. And I wanted to do this.

  14. #89
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    I was born in the mid 60?s and one of the first things I remember being truest enjoyable was the streaking fad of the late 60?s / early 60?s. Fast forward a few years and I was going to take a shower and found mom?s pantyhose hanging to dry. Well, I tried them on and that was it I was hooked.
    In high school, for a Halloween party senior year, I borrowed a girlfriends cheer leading outfit. It was a great time. I should say one year I wanted to go out trick or treating as a girl and mom was firmly NO.
    Anyways, junior high and most of high school was the streaking thing, it from the early 20?s I would ?borrow? my girlfriends lingerie.
    Then thinks went quiet for several years (maybe 10 years or so). No dressing.
    Then about 10 years ago it came back full force.

  15. #90
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    Being raised by women, I think I always wanted to be a girl. Started wearing heels when I was 7 and then dressing around 12. I?ve gone through long times without being Olivia, but now I know we are the same person, I am Olivia, I just only look like her sometimes but I can feel like her in my imagination in those times where I can?t physically transform. Now I?ve come so far with breast forms and beautiful wigs and a wardrobe with some heels that I am the best version of me I?ve been even though it?s been decades!

  16. #91
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    I've thought a lot about this. I grew up with 2 sisters but they didn't have any influence on me. For example, they never dressed me up and I never wore any of their clothes.

    It was my mother. Her and my father were swingers. She had all types of sexy lingerie And my dad had all the magazines like Hustler, Playboy and Penthouse. I found women in stockings and garters hot as hell. I'd masturbate to their pictures all the time in my teens. At some point, alone in the house, I snuck in to my mom's drawer and got her stockings and garters. At 13-14, I was too young to have a girl and I suppose the idea was just to put them on myself.

    But it never went further than lingerie until I was divorced in my 40s. I finally had money, a place to my own and one thing led to another until I was a full blown CD with thousands of dollars of clothes, makeup, shapewear, silicone breasts, wigs, jewelrly, shoes, etc.
    Last edited by char GG; 09-16-2021 at 10:14 PM. Reason: Some topics are not allowed/please read the rules

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