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  1. #1
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    What was the first time you wore?

    I was eight years old when at last minute went to stay over night at my cousins - I had no clothes with me, but was going going to borrow some old clothes belonging to my older cousin who was also a boy.

    When we got to the house and started preparing to go to bed, my Aunt realised that there were no old pyjamas for me to borrow - In the end she said I would have to borrow something to wear from my other cousin who was a girl - I thought she meant pyjamas , but I ended up going to bed in one of her nylon nighties - it felt so silky compared to cotton pj?s I normally wore.

    The next morning I even had my breakfast still wearing it.

    When I was getting dressed I need some clean underwear and ended up wearing some girls knickers - again felt really nice compared to my y-fronts - I was still wearing them when I got home - unfortunately my mum washed them and gave them back.

  2. #2
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    I don't recall my exact age. I was very young. My mother use to hang her slips to dry on a clothes line in our apartment. The way the clothes hung to dry made it so any person had to duck and go under the clothesline as you went down the hallway. I discovered the lovely feel of nylon as I brushed by the slips. I would caress and fondle them. There was also a drying rack above the bathtub. When she hanged the slips on the rack I ultimately ended up taking them down and trying them on. I loved the feel of nylon. There was no thoughts of being female. There was no sexual stimulation. That did not occur until puberty.

  3. #3
    Female Illusionist! docrobbysherry's Avatar
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    Over 50. It never occurred to me to try on female clothes before then!
    U can't keep doing the same things over and over and expect to enjoy life to the max. When u try new things, even if they r out of your comfort zone, u may experience new excitement and growth that u never expected.

    Challenge yourself and pursue your passions! When your life clock runs out, you'll have few or NO REGRETS!

  4. #4
    Platinum Blonde member Ressie's Avatar
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    My sister's coat on Halloween. I was 4.
    "You're the only one to see the changes you take yourself through", Stevie Wonder

  5. #5
    Aspiring Member Kelli_cd's Avatar
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    I was probably 4 or 5. My grandmother had a petticoat (maybe it was a crinoline?). I remember putting it on, but it was probably over my pants. I don't know if my sister and I were playing some kind of dress up? We used to spend the summers with my grandparents. I know I put it on more than once.

    I also remember being attracted to the feel and swish of nylon. To this day, I love the feel of nylon.

  6. #6
    Senior Member April Rose's Avatar
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    At 4 or 5 my cousin put her kerchief on me. I don't really remember the first time I put something on by myself. I know it was before I was seven. That was the first time I was caught. I know I had done it before then and gotten away with it.
    I am a vessel of the goddess. Let me express my calling to a feminine life through nurturing love and relatedness.

  7. #7
    Senior Member Angela Marie's Avatar
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    I was about 10 years old and tried on a pair of my moms black tights (now called leggings). Hooked immediately.

  8. #8
    Gold Member Lana Mae's Avatar
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    First time I wanted to was at between 5 and 6! A playmate(Lana) threw her dress over her head and I thought that was great and I wanted a dress! Of course,I was a boy and boys don't wear dresses! Early teens was mom's panties! That was the first wearing! Hugs Lana Mae
    Life is worth living!
    "Foxy lady! You look so good!!" Jimi Hendrix

  9. #9
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    First time I dressed (albeit about loose a definition of dressed as you can get) came aged 11. I had developed a fascination with skirts over the previous 3 months and had reached the point of having an overwhelming urge to try one for myself.

    Fortunately, I have a sister (else who knows what I would have resorted to) and on this particular day everyone else was going to be out of the house. I think my dad might have been at work and my mum and sister going to a parent?s evening at school (not 100% on that).

    Anyway, I left it long enough to be sure that no one was going to come back unexpectedly and sneaked into her room to try one of her skirts on. It was a brown skirt with a netted pattern stitched into the outside. Anyway, I knew then that this was an awakening and there would be no going back.

  10. #10
    Aspiring Member Lacey New's Avatar
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    I don?t remember the exact time but I was a young teenager 13, 14 or maybe as late as 15. But back then girls wore miniskirts to school and by dropping a pencil in class and looking backward, I would be rewarded with a peek of panties. And thinking about what was under those panties was sexually arousing. I also had access to Sears and Penny?s catalogs that showed some lovely lingerie. Well, eventually, I found the laundry hamper where my mother and sister deposited yesterday?s parties. At first, I would just hold and feel the panties as I would take care of business and then the inevitable happened and I put on a pair of nylon briefs. I?ve been hooked ever since.

  11. #11
    Junior Member Brandi17's Avatar
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    Depends on your definition of first time wearing. If you mean the first time I wore any female clothes, then that was probably when I was 15 or 16 I started wearing what I called 'Male bikinis' under my underwear. I called them that because it was technically made for a guy, but had a panty like style to it. A short time later. Of course I eventually upgraded to actual panties that I managed to buy at work and sneak home. If you mean the first time I went out FULLY dressed, then that would have been in 2018 some time.
    -Brandi

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  12. #12
    Silver Member Pumped's Avatar
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    I started with my mom's bras and nylons at an early age, maybe as young as 5 years old. I remember dressing up and pretending to be a dancer like one of the Rockettes. I fell in love with the fancy outfits, nylons, sequins, even the large fluffy "tail feathers" they sometimes wore.

  13. #13
    Aspiring Shopaholic BTWimRobin's Avatar
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    Growing up we didn't have a cloths dryer so mom would always hang the laundry up in the basement to dry. Since the basement was also my playroom, I had access to bras, girdles, slips .... all hanging there just begging for me to try them on. And try I did and was completely addicted. Mom used to dry her stockings in the bathroom and I would slip them on every chance I got. Absolutely love the feeling.
    - Robin


    Because life is too short not to.

    It's ironic ... I finally found a group of guys I fit in with. Funny how they all enjoy being one of the girls.

    Wife: Why do you fold your panties? Me: I don't like my panties in a wad!

  14. #14
    Member Denice's Avatar
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    I was maybe 10 or 11 when I slipped into a pair of fishnet stockings.
    I'm a man. I like being a man. I also love wearing women's clothing. It's my way to show honor, respect and solidarity with them.

  15. #15
    Senior Member BrendaPDX's Avatar
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    I was a freshman or sophomore in high school, I was at a thrift store and ran across a dress. I liked it so much, hands shaking I stepped up and bought it. I tried it on that night, it had a side zipper (I hand never seen that before), the dress pulled around me as I zipped it up and fit me perfectly! I looked at myself in the mirror for several minutes, I was hooked!

  16. #16
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    I was maybe 12 or 13, my mom's shiny red briefs. Don't know why I first tried them on but I was going through her panty drawer one day and it just felt so natural to take off my clothes and slip into them. It was the first time I masturbated wearing women's clothes. It was an amazing turn on and I was hooked!

  17. #17
    Member HelpMe,Rhonda's Avatar
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    My standard answer is that I remember putting on mom's earrings when I was too young to remember anything but there was a big reaction to that and then I didn't do anything like that again until I was old enough to be left home alone.

    I always read the stories of people who didn't need to do it until they were 40 or 50 and wonder if that was better or worse? Of course I should have taken more pics when I was younger and maybe cuter but polaroids sucked and digital cameras were hard to come by for some reason.

  18. #18
    Platinum Member Crissy 107's Avatar
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    I was around 11 or 12 and it was at least my moms panties but soon progressed to trying everything and of course loving every minute. Fond memories for sure.
    Crissy

  19. #19
    Lady in waiting Peggie Lee's Avatar
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    As far back as I can remember around 4 I would play dress up in my mother?s clothes when ever my parents were not around until about 9 then stopped after being caught but at 12 I had a girlfriend that would let me wear her clothes as we were the same size, my happiest memory was dressing in her Girl Scout uniform with her selling Girl Scout cookies door to door. It all ended with my brothers death when one of my dad?s customers after seeing me said To my dad he liked the cookies my sister sold him ( I don?t have a sister).

  20. #20
    Member Michelle_G's Avatar
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    I do not remember an exact age but I was probably 8 or 9. My mother's old dance leotards, one piece swimsuits, and pantyhose.

  21. #21
    Member Christina89's Avatar
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    i was about 12 or 13 when i first wore one of my mothers old 2 piece bikinis.
    I'm just a simple someone trying to figure life out.

  22. #22
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    I was 13 when I started. Wore a beautiful foral print dress which felt wonderful.

  23. #23
    Senior Member SaraLin's Avatar
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    Around 5 is the earliest I remember.
    I was staying at grandparents' house for the night (unplanned) and grandmother gave me one of her house dresses to wear as PJ's.
    I'm not sure that this ACTUALLY the first time, since I have a history of 'borrowing' things from my sister all throughout my childhood. Too many to remember when I started, so I can't say which came first.

  24. #24
    Member Charlotte Haynes's Avatar
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    I was 10. It was during the school Summer break. We usually stayed at my grandparents, but as I was doing some cycling course in the mornings, I stayed home alone. This was a first.
    I was obsessed with tights/pantyhose, and during this time I can recall rummaging through my Mams drawers for some. I liked to touch them. This particular time I pulled them over an arm, then over a leg, then panicked. I put them back and went downstairs. A few minutes later I was back up there, and the urge took over, and there I was standing in front of the mirror wearing my Mams black pantyhose. An electric feel. Over the next few days I repeated this, and also wore a tan pair with heels. I remember wearing a girdle and a slip, but never panties. They seemed a step too far.
    Last edited by Charlotte Haynes; 07-09-2020 at 07:32 AM.

  25. #25
    Member Jemima Stephens's Avatar
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    I used to go to a Child-minders after school and she had 2 daughters, one 1 year below me, the other 2 years younger than that.
    I was about 8 when I got a drink spilled all over me and had no change of clothes, so the Childminder stripped me off and dressed me in pink panties, brown girl's trousers and a pink T shirt. I remember the surprise on my Mum's face when she picked me up and I also remember looking at myself in the full-length mirror when I got home - I stayed in the clothes for a while until just before my Dad got home.

    Of course the girls would 'accidentally' spill things on me occasionally after that, those clothes were put aside for me to wear if it happened...Of course I had no real understanding of what was going on inside my head at that time other than it felt good but wrong at the same time.

    Just remembered whilst writing this, I stayed overnight once, my parents must have gone away, and I ended up spending all day wearing those clothes for some reason.

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