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  1. #1
    Discovering the Gurl Xandra's Avatar
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    When did you first crossdress?

    Do you remember the first time you tried on an item of women’s clothing?

    I remember putting on my mum’s fake fur coat around age 7 and getting a thrill from my appearance in the mirror. I knew at once that this was part of my future. How about you?

  2. #2
    Gold Member ~Joanne~'s Avatar
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    I remember having an pantyhose fetish at an very early age. I think I was 10. I loved The way they looked on women, how "see through" they were, The shine they gave off and how cute they made feet look. It was within that same age that I wanted to know how they felt on me so I stole a pair of my mom's. They didn't look as good as they did on other women (to find out it came down it brand and such) yet they felt amazing! There was little turning back after that.
    Flip Flops were made for Beaches & Bath Houses, We have neither in 2017. Lose the flip flops!

  3. #3
    Junior Member artofbalance's Avatar
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    I used to be dressed up in ballerina outfits my sister had as she was growing up... about 4 years old I think. I remember about age 4 trading underwear with a girl my mom babysat for. They were white with strawberries on them.

  4. #4
    Member Jamie Christopher's Avatar
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    As I remember, I was about 11. We had a big house, 8 kids, 3 girls and 5 boys, the girls all my elder. I went up in to the attic one day, and was going through some boxes of stuff, and found a white full slip. I remember taking off my shirt, and pulled that slip over my chest and pulled it down....the feeling was intoxicating...and the eventual result is what you might imagine; a first for that little boy...lightening! There was no turning back after that, I was changed forever! After that my mom started finding me hiding one of her bras between my mattress, oye! Still one of my favorite things: pick out a pretty white bra, insert my breast forms, and pull a nice lacy full slip over and down over my body...heaven! I always wished I could look down at my chest and see female boobs.....
    Last edited by Jamie Christopher; 12-17-2013 at 12:37 AM.

  5. #5
    Aspiring Member ShelbyDawn's Avatar
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    I can remember being five or six and sneaking into my moms dresser and stealing her slips.
    I still love satin and lace...
    As I got older, I started "borrowing" things, panties, bras, dresses, etc., from my sisters.
    Once I moved out on my own, it became more opportunistic; i.e., I would get lucky enough to have a pair of panties mixed in with my laundry in the apartment complex or a girl friend would leave something at my place.

  6. #6
    New Member Sophie Hogletta's Avatar
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    Ballerina outfits. Nice.

    Quote Originally Posted by Joy3 View Post
    I was about 5 yrs old when a girl neighbor dressed me up in her clothes so she could have a girlfriend to play with. I loved it very much she and I played many times and i was hooked!
    My best friend when I was five or six was a girl, but we never did that. You are very lucky! Innocent times . . .
    Last edited by Lorileah; 05-19-2015 at 12:37 AM. Reason: merged several responses. You can add to your reply using the edit

  7. #7
    Junior Member Rebecca Cross Bracer's Avatar
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    Quote Originally Posted by ~Joanne~ View Post
    I remember having an pantyhose fetish at an very early age. I think I was 10. I loved The way they looked on women, how "see through" they were, The shine they gave off and how cute they made feet look. It was within that same age that I wanted to know how they felt on me so I stole a pair of my mom's. They didn't look as good as they did on other women (to find out it came down it brand and such) yet they felt amazing! There was little turning back after that.
    Almost the same story for me, but I loved the look and feel of the pantyhose and progressed from there. Slowly at first, mostly just pantyhose for a few years, then my sisters' bras and dresses, now all out when possible.

  8. #8
    Member Karen_the_Cutie's Avatar
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    i wasnt even in kindergarten yet, so i guess like 3 or 4. first thing i wore was my sisters pantyhose. also my moms bra (which was waaaay too big for me being so young. lol) and my sisters nightgown shortly after, but not same day. I wish I had been open about it then, I even knew I wanted to be a girl then. I remember playing with my grandpa and asking him to call me tiffany, cause that was the cutest girl in my class and i wanted to be like her :3

  9. #9
    Member monica.missil's Avatar
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    I was 12. Put on mom's bra and girdle. Then put on her nurse uniform.

  10. #10
    Discovering the Gurl Xandra's Avatar
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    I love the progression!
    Quote Originally Posted by monica.missil View Post
    I was 12. Put on mom's bra and girdle. Then put on her nurse uniform.

  11. #11
    Junior Member Sami's Avatar
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    For me since 8 or 9 years old and have done ever since

  12. #12
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    First time was around 8 or 9, during a summer break from school while being left home alone. Tried on some of my mom's panties and a nightee, the feel is what hooked up. I even tried some of her lipstick as well and spent as much of the day as I could like that. Sadly, I've not discovered how much a part of me it is until just recently

  13. #13
    Discovering the Gurl Xandra's Avatar
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    I remember "borrowing" my mum's lipstick when she was out and seeing how my lips looked. So much better!

    Quote Originally Posted by Jasmyne View Post
    First time was around 8 or 9, during a summer break from school while being left home alone. Tried on some of my mom's panties and a nightee, the feel is what hooked up. I even tried some of her lipstick as well and spent as much of the day as I could like that. Sadly, I've not discovered how much a part of me it is until just recently

  14. #14
    New Member billy419's Avatar
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    when I was about 17 I would wear panties sometime, in the last year I have been dressing up some

  15. #15
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    I first crossdressed when I basically started walking!!! I can't remember a time when I wasn't a xdresser... that's why I feel like I'm a girl although that doesn't effect my masculinity.

  16. #16
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    Probably about the age of 10. Those pantyhose just hanging there in my grandmothers bathroom were just too much to resist.

  17. #17
    New Member kayla316's Avatar
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    My mom held dress up to me when i wa 5 to check the size for a friends bday gift and I thout it would look nice on me. Didn't get to try it on though. A few years after that found a dress that would fit and tried it on and been hooked ever since.

  18. #18
    Silver Member I Am Paula's Avatar
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    My sister and I were very close. She'd dress me up starting around 5 or 6. Alot of kids play dress up like that, but I liked it too much. By my early teens, at pajama parties I was my sister's make up manequin.-Celeste

  19. #19
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    As early as I can remember...probably around 4 years of age.

  20. #20
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    Probably as a single digit midget. I fondly remember taking my mother's nylon slips off the clothesline and trying them on. I loved the feel of the material. I had no conscious thought that I would like to have been born a girl. I had no sisters or female playmates. No one dressed me up. Maybe, if my mother wore cotton slips I would have turned out differently????

  21. #21
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    I might have been 4 or 5, I would go into my moms closet and put on her girdle,
    Then try walking around in her heals.
    That was OK for a while, but when she caught me wearing her girdle and
    nylons in bed when I was 10, I got the "TALK".
    Had to hide stuff better, Under the mattress was no good anymore; so I went
    to work and built a false bottom to my built in dresser drawers. Worked like a charm.
    Then when I went off to the Navy, I had to purge everything, That hurt.
    I left a note in the hiding space saying, "HA, I caught you looking at my Hiding Space"
    The old house is still there, all though we moved out 40 years ago; I wonder if anybody
    found the note.
    Rader

  22. #22
    Gender Outlaw! vikki2020's Avatar
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    about 4 years old---slipped on some nylons, and never looked back!
    "And if you want some fun, sing Ob-Bla-Di-Bla-Da!"

  23. #23
    Member cdtraveler's Avatar
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    I was 6 and about to go on stage to sing at the high school for a holiday show and this well endowed teacher with her cleavage showing leans down and says wait honey you haven't had your stage makeup put on yet then proceeds to apply red lipstick. I can still smell her perfume and see her lace camisole. She then tells me how pretty I look and sends out on stage. On ride home I can still taste the lipstick. I'm mesmerized. Next day I'm standing in front of Mom's dresser reach for her lipstick apply it and well I've never lost the desire for feminine finery 45 plus years later.

  24. #24
    Discovering the Gurl Xandra's Avatar
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    Quote Originally Posted by cdtraveler View Post
    I was 6 and about to go on stage to sing at the high school for a holiday show and this well endowed teacher with her cleavage showing leans down and says wait honey you haven't had your stage makeup put on yet then proceeds to apply red lipstick. I can still smell her perfume and see her lace camisole. She then tells me how pretty I look and sends out on stage. On ride home I can still taste the lipstick. I'm mesmerized. Next day I'm standing in front of Mom's dresser reach for her lipstick apply it and well I've never lost the desire for feminine finery 45 plus years later.
    What a lovely memory...

  25. #25
    New Member Nicky63's Avatar
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    The first time for me I was maybe 12 - 13 and I found an old blouse presumably belonged to my sister. I remember it was pretty wih lacy edges and I liked how it felt on me although I had no concept of cross dressing, it was just a bit of fun. It wasn't until my late teens I was staying at a freinds house his girlfreind had just left him and I found in his garden shed a bag full of her clothing, knickers bras etc. I just had no hesitation in trying them on and I've been hooked ever since.
    Nicky
    xx

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