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Thread: When did you first crossdress?

  1. #376
    Aspiring Member dana digs sweaters's Avatar
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    4, was wearing a slip and I do not remember this but have a pic of me in it. Was 5 when I took a cardigan from one of my sisters and remember that.

  2. #377
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    The earliest I can remember was maybe five. My parents had a big fight my mother was crying and I was frightened I ran to the bathroom where my mother had left a blouse that I liked because of the patterns and colors. I put it on of course it was too big but the feel of it was something new for me and I did it every chance I got ever since.

  3. #378
    First time for me was when I tried my 3 year olders sister's one piece swimsuit when I was 6. I liked it back then so my mom asked me if I wanted her old cloth. I said no cus I was affraid, regrets regrets

  4. #379
    Paula Siemen Paula Siemen's Avatar
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    I was probably 11 or twelve. I had a sister two years older than I and watched as she developed from a girl to a woman. I was so intrigued with all the girl stuff she had. Panties, bras, pretty dresses and the makeup. When everyone else would leave the house, I'd go into her room and try on her panties and bras. I was heavy, so I really couldn't get into her dresses. I loved the feeling of her clothes. Just everything in her wardrobe was so intriguing to me.
    It set me on my path to the CDer I am today.
    Last edited by Shelly Preston; 12-08-2013 at 11:11 AM. Reason: some subjects are not allowed

  5. #380
    A happy, mature lady! Joy3's Avatar
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    At age 5 a neighbor girl would dress me in her cloths so I could be her girlfriend. I loved it and started wearing some of my moms things. I was hooked and love it to this day!!

  6. #381
    Lacy Lacyfem's Avatar
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    I was ten when I slipped into my mom's panty and bra and was immediately hooked!

  7. #382
    Member Connief's Avatar
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    I was about 5. During the summer, mom would leave me with a babysitter while she went to work. The babysitter's daughter and I use to play dressup then play with her dolls. I loved dressing in her pretty dresses. Sometimes the babysitter would let us wear her necklaces and earrings. After that I was in mom's closet every chance I could get. Loved wearing her peignoir sets and dresses and yes all the under trimmings.

  8. #383
    Member teri222's Avatar
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    Carla, 59 or 60? Unbelievable! You are so feminine and "dress" so well. Hey girl, I just took a look
    at your pictures on flickr. Very well done. Thank you for sharing them with us.

  9. #384
    Senior Member missjoann49's Avatar
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    Quote Originally Posted by Phoebe View Post
    Four and five years old, my mother had me put on dresses she made then have me get on a chair so she could make the hem straight. Sometimes wore those dresses all day long. My father was away in the hosptial then and never knew my mother dressed me in dresses.
    Phoebe, you and I had kimd of the same experience, I was around 3 or 4 years old, an only child and my mom had always wanted a girl...my dad worked alot of nights, so when ever she had the chance she would dress me as a girl, this went on until about my first year of high school then she stopped....It was only a few yrs later while I was on my own that I started doing this again as I had missed it so much....hence after a couple of bad marriages I am well on my way to who I am and who I will be till the end of my life
    Hugs
    Joann

  10. #385
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    I found this particular thread very interesting. The commonality of experience is astounding, though the details vary a lot. I was impressed that so many respondents mentioned that the first dressing experience was so clear and so powerful and erotically arousing. So, I did a count to see which ages were the most common. I divided the replies into bands;<5, 5-10; 10-20; 20-30; and lastly 30+. I could not get a clear age for a few responses and there were several multiple responses that I caught, but I may have missed a few. So, there are some errors of course but not too bad.

    Anyway, 28% of those responding reported a memory of cross dressing at or before the age of 5. The largest group sat between 5 and 10 years--- 45%. There were 24% between the ages of 10 and 20. After that it tails off quickly with about 2% reporting a first experience in their 20's and a similar number for the 30+ group.

    i didn't break it down any finer but of the 5 to 10 group there were many who stated 6 or 7, so the data may actually be skewed toward the early part of that range. I had to go through 16 pages to get this result so I don't feel motivated to go back and regroup the data. Perhaps someone else has done so already.

    So, just as we all thought, the age at which we first experienced that cross dressing thrill, mostly with lingerie by the way, was younger than 10 years old. However, a significant number did not start until they were in their teens.

    Any thoughts or comments from anyone?

  11. #386
    Aspiring Member krissy's Avatar
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    I traded clothes with my sister in a movie house at the age of ten but i use panties at 7

  12. #387
    Member JessMe's Avatar
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    I've got a sister that is four years younger than me... not sure of my exact age at the time, but she wasn't born yet when I started making "dresses" from my bedsheets.

  13. #388
    Junior Member Katy120's Avatar
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    I wonder whether you can draw a direct line from the experience of dressing in your mum's intimates as a youngster and crossdressing as an adult. Is wearing your sister's panties a seminal event? I'm sure I don't know. However, I wouldn't be surprised to learn that many young boys try on bras and panties as a child and never crossdress later in life.

  14. #389
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    My mom's panties were accidentally in a pile of my own laundry when I was about 10. I have no idea why, but I put them on, looked at them on me, and got a huge rush of excitement (metaphorically and unfortunately, literally). The rest is history.

  15. #390
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    Quote Originally Posted by Katy120 View Post
    I wonder whether you can draw a direct line from the experience of dressing in your mum's intimates as a youngster and crossdressing as an adult. Is wearing your sister's panties a seminal event? I'm sure I don't know. However, I wouldn't be surprised to learn that many young boys try on bras and panties as a child and never crossdress later in life.
    Perhaps they do not go on to become a cross dresser but for me and the several hundred others on this site and hundreds of thousands of cross dressers around the World, it must have been a life changer.

  16. #391
    Senior Member dawnmarrie1961's Avatar
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    "It all began such a very long time ago...." Actually I haven't the faintest idea. I'm still working on that one. Ask me again later. OK? I might have an answer then.
    CANCER IS A BITCH SO YOU HAVE TO BE MORE OF A BITCH TO BEAT IT.

  17. #392
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    My first time was when I was around 4 or 5 years old. I used to find my mothers pantyhose and put them on and really liked the way they felt. Then, at around 12 or 13 years old, I really got into nylon panties and loved wearing them and pleasuring myself with them. As my teen years went on, it kept getting more intense. When I was around 17, I started buying my own clothes, usually from thift stores and such. By the time I was 20 I had a full wardrobe and became who I am now.

  18. #393
    Aspiring Member Susan.'s Avatar
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    I barely remember my two little sisters and I dressing up while playing in a pile of dirty clothes. I was probably 6 or 7.

  19. #394
    New Member Kelly Anne's Avatar
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    I don't remember how old I was however I remember wearing my mother's thongs and bras and even though I was very careful (I thought) at putting them all back where I got them they disappeared out of her drawer after about a year of me doing this. So when I turned 16 I started wearing men's thongs and told my mom that I wanted to wear thongs which she supported and even went shopping with me to buy them. I told her there wasn't much selection so we could always go look in the women's department to find some since they're basically the same thing... She said there was no way she was buying womens underwear for her son. She never said I couldn't but she wouldn't buy them. So after I left for college I started buying... not I have a lot of lingerie to make me happy

  20. #395
    There's that smile! CarlaWestin's Avatar
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    I was an astronaut. While listening to the final 10 seconds of the countdown, I used my smartphone to order a leather corset and six inch heels from ebay.

    Not really. At age ten or so my mother's bras called to me from her lingerie drawer.
    I've waited so long for this time. Makeup is so frustrating. Shaking hands and I look so old. This was a mistake.
    My new maid's outfit is cute. Sure fits tight.
    And then I step into the bedroom and in the mirror, I see a beautiful woman looking back at me.
    Smile, Honey! You look fabulous!

  21. #396
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    I was probably 4 or 5 years old... I used to like to play in the freshly dried laundry because it was nice and warm out of the dryer. One day I found a pair of my mom's trouser socks in there and loved how smooth and comfy they were so I would sneak them on and wear them around the house. One day I was caught and got pretty embarrassed so I stopped for a while.

    I started again in my early teens, but was much more careful about being caught. I got progressively more and more into it through high school and college and started buying my own things...much more fashionable than my mother's clothes!

  22. #397
    Martini Girl Katey888's Avatar
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    This is a really interesting thread and question (and answers!) - really made me think too. I would have been about 6 or 7, and girls' fashion at the time (this was late 1960s) was for fluffy, acrylic hats that tied under your chin. At school, I would ask to use the toilet (restroom...), go into the cloakroom that was outside the classroom and try on the girls hats. It's weird now thinking/writing about this, but there was obviously something sensual happening about both the feel of the clothing and the fact that it was 'disguising' or transforming me. I've only thought about this now, but that desire was overtaken very rapidly by coming in contact (literally) with my mother's nylons which were obviously lying around the house. I can remember the thrill of trying on different styles and colour stockings in my bedroom and loving the sensation - it's still there today. That progressed to illicitly obtaining my first pair of fine grey tights/hose a few years later and wearing them with a wraparound skirt - the combination was quite explosive... Wow...
    "Put some lipstick on - Perfume your neck and slip your high heels on
    Rinse and curl your hair - Loosen your hips, and get a dress to wear"
    Stefani Germanotta

  23. #398
    New Member karens70's Avatar
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    I dont remember exactly, I think it was around 9 or 10, I just remember that the sensation of pantyhose did something to me that I could not explain but I really liked. I do then remember moving into trying other clothes that belonged to my sister/mother and found that adding a dress/shoes etc enhanced those feelings.

  24. #399
    Member Marla's Avatar
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    Loved wearing my Moms lipstick.

  25. #400
    Member laciewhite's Avatar
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    it was very early for me, not sure exactly what age but pre-school, trying on my mum's shoes and stuff like that. i always felt it was a naughty thing to do and always did it in a very secretive way.

    and when i started school i remember wishing i could wear knee-high white socks like all the girls did.

    i got interested in nylons and lingerie pretty much from puberty onwards. started trying on my mum's things. and my dad's girlfriend's stuff (my parents were divorced by then).

    got into make-up and buying my own clothing in my twenties.

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