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Thread: What was the first time you wore?

  1. #1
    New Member
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    Jun 2020

    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
    Platinum Member
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    Oct 2010
    Western Washington
    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
    Weirdest woman ever! docrobbysherry's Avatar
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    Sep 2007
    Orange County, Calif.
    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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    Feb 2008
    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
    Member Kelli_cd's Avatar
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    Jun 2018
    North Texas
    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
    Aspiring Member April Rose's Avatar
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    Oct 2017
    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
    Junior Member
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    May 2020
    Bristol, UK
    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.

  8. #8
    Junior Member Brandi17's Avatar
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    Feb 2019
    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.

    Follow me on my new Instagram to follow all my adventures as Brandi:
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  9. #9
    Senior Member Pumped's Avatar
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    Aug 2013
    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.

  10. #10
    New Member
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    Jun 2020
    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!

  11. #11
    Member HelpMe,Rhonda's Avatar
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    Jun 2019
    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.

  12. #12
    Member Michelle_G's Avatar
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    Jan 2015
    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.

  13. #13
    Member Christina89's Avatar
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    Apr 2009
    South Shore, Massachusetts
    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.

  14. #14
    Aspiring Member SaraLin's Avatar
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    Jun 2017
    Central Fla.
    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.

  15. #15
    Member Jemima Stephens's Avatar
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    Feb 2020
    Midlands, UK
    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.

  16. #16
    Aspiring Member
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    Jan 2008
    Southeast PA
    The first time I remember: I was 4 or 5, and I couldn't resist getting into my sister's full white petticoat. This was back about 1957 or '58. I still love petticoats.

  17. #17
    Gold Member Crissy 107's Avatar
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    Aug 2018
    Maryland, USA
    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.

  18. #18
    New Member Sarah Handy's Avatar
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    Nov 2019
    Houston Texas
    I was five and put on my moms panties and bra been dressing ever since.

    [SIZE=1]- - - Updated - - -[/SIZE]

    I was 5 my moms panties and bra been dressing ever since.

  19. #19
    Danielle cdinmd206's Avatar
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    Feb 2007
    Southern Maryland
    When I was probably 5 or 6 years old I found and old one piece bathing suit in the attic and for some reason wanted to try it on. I took it and hid it in the woods by our house. A few days later i tried it on and loved how it felt. When I was around 10 I was spending some time at one of my aunt's house and long story short I spent an entire week with her dressed as her niece.

  20. #20
    Banned Read only Vicky_Scot's Avatar
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    Jul 2006
    Bonnie Scotland
    I was 12.

  21. #21
    Senior Member Tracy Irving's Avatar
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    Aug 2016
    I think I was around 5 when I put on my mothers panties for the first time.

  22. #22
    Sort of a n00b Pixie_94's Avatar
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    Aug 2017
    Costa Rica
    I think I was 10, but if my memory isn't fooling me, 7. The shame crawls on my back.

  23. #23
    Senior Member NancySue's Avatar
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    Jun 2016
    Southern Illinois
    Next door sisters would play dress up. They invited me to join them. I?m 6-7. Nothing happened until I slipped on a pair of pantyhose. Wow..bells, whistles. I then found Mom?s pantyhose and thigh highs. The rest of the story is obvious.

  24. #24
    Platinum Member
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    Jan 2010
    Somewhere deep in the fog of memory. I remember trying on my sister?s slip. Had to have been before I started school (we didn?t have kindergarten). I remember some comments by siblings about being a house-boy...apparently not being masculine enough at that early age. I perhaps overcompensated in subsequent years, but it didn?t help.
    Our only truth is narrative truth, the stories we tell each other and ourselves, the stories we continually recategorize and refine. Such subjectivity is built into the very nature of memory. Oliver Sacks

  25. #25
    Banned Read only
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    Sep 2016
    Phoenix, Arizona
    I was 12 or 13 when I first had the urge to put on a skirt of my mother's.

    Before long I was also into her panties and bras, girdle and nylons, slips, blouses, dresses, the works!

    I'm glad most members responding here are putting their experience into a context or describing their feelings around it. I did try on my mother's nightdress once when I was four or five and it was lying on the bed next to me. And when I was seven my mother dressed me as a woman for a competition--and would you believe, I won first prize! But I don't count those events because they were isolated occurrences and not psychologically significant. The nightdress incident was a mere experiment, done on a whim, and I have no memory of any special feelings associated with it. And it was my mother who instigated the costume incident. More important, neither incident gave me an urge to repeat the behavior in childhood--even if it was rewarded with a prize! But when I put on my mother's skirt at 12 or 13, that's what really got me started crossdressing!

    It's a pity we can't do it on this board because we're all crossdressers here, but it would be interesting to survey how many non-crossdressers have put on female clothing at some time in childhood, or had it "put on them." I'm guessing it would be a large percentage. I think we have to have that inner urge to become a permanent crossdresser, and that "first experience" was either a result of that urge, or else just a "trigger" for what followed.

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