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Thread: How old were you when you started and who's clothes?

  1. #1
    forever in pantyhose Jill's Avatar
    Join Date
    Apr 2004
    City of the Salt, Utah

    How old were you when you started and who's clothes?

    I was about 11 or so when I started my dressing. My sister dared me to try on one of her old dresses one day and I did. I was hooked after that and continued to dress through my teenage years. I had three sisters so I had quite a variety to choose from. How old were you when you started and who's clothes?

  2. #2
    pantyhose freak PrettyPolly's Avatar
    Join Date
    Mar 2004
    Alberta, Canada
    I was 12 when I started. Stayed at a friend of my parents and I always used her lingerie as she was dead sexy. I didnt think that she new about it but I was wrong. Was visiting when she suggested to my parents that I saty over cause she needed me to move some furniture for her in the morning. I had no spare clothes with me but decided to stay. After a shower I walked into my usual bedroom that I stayed in only to find a pair of sheer white panties, a bra, sheer nighty and a pair of pantyhose neatly laid out on the bed. When I turned around she told me that the thought of me wearing her lingerie was driving her mad and that my secret would be safe with her. Needless to say I loved staying there as she was single with no kids. She allowed me to use all her clothes and I loved it. When I was much older we would have some very nice dressing sessions which normally ended in a night of passion......

    I'm married now but still see her once a month or so....

  3. #3


    I started out at school! My infant school had a dressing up box which we used every week. I always wore the same slip. Apparently the teachers didn't know quite what to do so they let me get on with it. Well if they want you to dress up you might as well do it properly! Later on I graduated to tights before starting to borrow my mum's clothes. She is from a generation which specialised in denial and although she knew what I was doing, and even once found my own stash of clothes, she preferred not to face up to the issue. I think that she hopes that I grew out of it. No chance!

  4. #4
    Member Jenny's Avatar
    Join Date
    Apr 2004
    I was about 9 years old when I tried on my sister's dress and panties. Unfortunately I got caught by my mother who explained very carefully that dresses and panties were for little girls not little boys and that I shouldn't ever do that again. So I followed my mother's directions and never ever put on girl's clothes again. (Not!!!)

  5. #5

    Smile How old were you when you started dressing girls clothes, and who's were they?

    i started dressing up like a girl when i was in grade 2. The clothes belonged to my sister. i think that we were having a tea party, and i was to dress for the part. As i got a little older, and self concious, i would sneak some old clothes from the laundry room, and secretly wear them in my bedroom. i would wash them with my clothes and no one ever found out.
    From sisy_p_wimp[COLOR=DeepSkyBlue]

  6. #6
    I was around 9. Found some of my sister's panties on my bed and tried them on. Immediately hooked. Didn't really become active in 'finding' clothes until my early teens, then I was into my sisters and mothers clothes whenever possible.

  7. #7
    i remeber when i was little, i would always wish upon stars and wishing wells that i could someday become a girl.
    my dream is starting to come true now.
    everytime im alone in my house, moms closet is open and her dresses, hose, and shoes come on.

    i have three brothers, 1 dad, and 1 mom
    my selection is very limited.
    and my moms stuff just isnt sexy enough these days...but...still

    i LOVE being a girl!
    Last edited by simpsonfan; 04-28-2004 at 12:32 AM.

  8. #8

    My First Panties

    I started when I was 15, for some reason I went to my sisters room, and looked in her pantie drawr. She was 19 a bit overwieght, but had large tits. I looked in the drawr and saw lots of panties most cotton white dull, but I saw a pair of sexy sheer briefs, white. I pulled off my pants, and put them on, I got so hard, but I hadn't yet hit puberty. I wore them all day. Later I would dress in my moms panties and bras, I was abused by afriend of the family, who liked to dress me, I felt guilty but liked it.

  9. #9
    CDer lookin 4 Fun Michelle Jo's Avatar
    Join Date
    Apr 2004
    Southern Kansas City, KS side

    Always a Little femme :)

    I was 7 ... caught my older brother using some of my older sisters lingerie to JO with ... he didn't know I saw him .. later that day I stole some of them from his hiding place and tried them on ... been dressing ever sense ... 40+ years and I am sure I will never stop ...

    Your Sister-n-Panties from Kansas,
    Michelle Jo

  10. #10
    Join Date
    Apr 2004

    Wink Very young

    I started when I was first able to dress myself. I'd wear my sisters clothes. We'd play dress up all the time. It began to taper off when I was in first grade. I still wanted to dress up but her interest seemed to be waning. I tried different ways to get her interested again but most didn't work. It's always been a part of my life for as far back as I can remember.

  11. #11
    New Member lara_myklund's Avatar
    Join Date
    Apr 2004
    NW UK
    I was about four, at nursery school. We had a dressing up box, and I used to always go for the dresses, they got me exited in a way I didn't quite understand.
    When I was about six, I anounced to my mum that when I grew up, I wanted to be a checkout-girl in Asda (I loved and still do the idea of being part of an all-female or all-feminized collective).
    My mum tried to take it in her stride, and told me a story about a man who had clinbed Everest, then at some point later had tablets and an operation to make look like a woman.
    For several years after that, I thought that climbing Everest was a pre-requisite for a sex-change.
    Didn't try dressing at home till early teens, when my parents started to leave me in the house unaccompanied.

  12. #12
    New Member jodyR's Avatar
    Join Date
    Apr 2004
    Northern Utah
    Hi Jill, I to am from Ut. I started dressing when I was 8 for the first time. Got caught by mother at a friend of hers. She really embarresed me in front of her friend. But didn't stop me. Emil me lets chat, we are so close. Luv jodyR

  13. #13
    Quote Originally Posted by Jill
    I was about 11 or so when I started my dressing. My sister dared me to try on one of her old dresses one day and I did. I was hooked after that and continued to dress through my teenage years. I had three sisters so I had quite a variety to choose from. How old were you when you started and who's clothes?
    wow goregeous legs baby... are those your legs?

  14. #14
    Hi Jill: I was 7 years old, when I found a bag of old lingerie in our basement. I, tryed it on, and I was hooked. I, kept going back to that bag for a long time, untill one day is was gone. When I was a teen ager, I started to buy panties which I wore quite offen. Today I wear womens lingerie all the time, including when I go to work

  15. #15
    I like most started at a young age, in my case 6 when I first strarted wearing my mommies panties and then very sheer and fragile nylons with the seam down the back.
    Could'nt wait till she went to work and I could get into her pantie drawer, she was a nurse so I loved the the white nylons too. Later I would steal the neighbor ladies panties and nylons off their clothes lines and hide them under my mattress. I haven't worn mens underware since was 17, I always wear panties and nylons under my regular clothes, and I buy them as small as I can so I can tuck my tiny .... between my legs so that there is no unsightly bulge. Wearing black lace panties, black lace thighhighs, bra 38B and my panties are wet as I am also gay and love it. Love Infante (which means child) my alter ego is Tina Marie. Well until next
    Last edited by Tamara Croft; 05-17-2005 at 09:26 AM.

  16. #16
    Shelley J.
    Jill - I was 5. My parents dressed me as a girl for halloween-I-ve been hooked ever since. I started wearing my mother's lingerie and moved to my sister's. In high school,I
    would totally dress in complete outfits. Today, i sneak my wife's lingerie.

  17. #17
    New Member Ivana's Avatar
    Join Date
    Mar 2004

    Thumbs up

    I started to crossdress when I was 12 or 13. My parents were pretty liberal when it came to nudity and sexuality. My mother used to let me watch her in the bedroom as she dressed. She would strech out her legs one at a time on the bed to put on her thigh-highs. That posturing to bring up the hosiery to her girdle for the final hooking into the garters really turned me on. So I knew that I had to do it too. She also let me hook-up her bra for her too so I learned at an early age to do it as well. My mother lured me into being a crossdresser

  18. #18
    I started when I wa 4 or 5. I clearly remember playing with friends (both sexes) in an old farmyard and coming across a basque (as I would call it now) pushed behind some timbers in a barn. We pulled it out and made yeuch noises then one of the girls said why dont you try it on? and I looked at her and for the dare of it did. And it felt so good....

  19. #19
    I was around 11-12 when I started and it was with my sisters clothes and luckily she never found out.
    Have been dressing up off and on for many years since.

  20. #20
    its always been the moms closet.
    today i snuck in there to take some nylon pictures...
    i cant wait till i can move out and have a closet full of feminine clothes.

  21. #21
    i was about 6 went i first started wearing my sisters leotards from her calisthics and my mum would allow me to wear them but over the years she thought i grew out of it and stopped wearing them , how wrong she was cause i still wear them and i love them, now all i have to do is started wearing dresses
    Last edited by Matilda; 05-03-2004 at 02:44 AM.

  22. #22
    oysters = kneecaps Abraxas's Avatar
    Join Date
    Apr 2004
    In your saddlebags, messing with your weight distribution.
    Wow-- lots of Utahns here. Surprising, I must say.

    I don't really remember the first time I wore mens clothes. I've always been erratic when it came to clothing. When I was about 3 I stole one of my little brother's diapers and wore it. So I suppose that was the first time technically...
    I've always had a little bit of a tie fetish (not a sexual fetish, I just love ties) and when I was about 5 or 6 I asked my stepdad to teach me to tie one. I used to (and still do) wear them all the time. By the time I was eight or nine I decided I would gradually start having my mum buy me more boyish- looking clothes. I eventually got her to let me shop in the boys department sometime that year. By ten I was wearing strictly boys outerclothes. I also began getting boxer shorts and putting them on over my womens underpants.
    That year my mum decided it was time for me to start wearing bras. I fought with tooth and nail against this. I despised the idea and would sneak off to school without one, or take it off in the bathroom once I got there. Once I was about 12 I decided it wasn't all that bad. When I started getting my periods (age 11) I hated the idea of wearing pads, and fought it but eventually of course gave into it. I passed well as a guy until the age of 15 or so. Now I'm 18 and I pack but don't bind. So that's pretty much my story.
    Yes-- socks! Run out again! Why is it that no matter how many millions of pairs of socks I buy, I never seem to have any? They just... disappear. Honestly, you'd think someone was coming in here, stealing the damn things, and selling them off. . . For me, socks are like sex: tons of it about, and I never seem to get any.

  23. #23
    An interesting question, I am not sure what I consider constitues my first experience, being made to crossdress, or choosing to, wearing clothes or cosmetics.

    I was in infant school when I first "crossdressed", it was for the school play and I had to wear tights, a leotard, makeup and wig. I made a big fuss cos I didnt want to be like a "Girl", but this may have been the start of things to come.

    At a young age I used to watch my mum bathing, shaving legs, dressing and doing her hair & makeup. I must have really wanted to do a makeover just like my mum did and started by getting a load of talcum powder and spreading it all over my face like mums foundation. I wonder what she must have thought, I guess it was a case of "oh he's just imitating what he sees".
    Definitely a deliberate attempt at changing my appearance and a sign that I may have have changed my mind about being a girl.

    Around age 11 the family went camping and when my parents were out of the tent and I was supposed to be reading I found my mums knickers and swopped them for the ones I was wearing. Even though barely different from my kids briefs they felt so good, I didnt know what I was doing or why, but I loved it and aside from some guilty occassions continued my exciting naughty dressing now and then when we got home.

    My mum started part time work as an "Avon Lady" (door to door cosmetics sales rep.) This lead to there being lots and I mean lots of make up around. I especially remember a lipstick tester case which must have had 200 different colors and shades. One lunch break, I and a mate had two girls from our class come over to my house. After some adolescent games we got dared to wear some of the make up. Never to wimp out of a dare, we were soon both wearing lipstick applied by the girls. As much as I acted like the fool I really enjoyed it.

    I guess I really started when I wore my mums knickers but there are many things that happened when I was younger that have lead me into my favourite hobby.

    luv Rhiannon

  24. #24
    New Member
    Join Date
    May 2004
    I was about 40 and it was just a few years ago. I had done my regular morning task of cleaning the house, showered and was looking for some underpants in the linen basket. I saw a pair of my wifes black lacy thongs and decided to try them on. i hadn't planned it, don't know why i did and had never even considered it before. Result - instant erection. I wore them as I walked to the shops and remember feeling so fantastically horny, especially as it seemed so wrong. I couldn't wait to get home to relieve the 'tension' and needless to say I didn't last long. I have been hooked ever since.

  25. #25
    Velvet Crossdresseruperer ~Tammy~'s Avatar
    Join Date
    May 2004
    Middle of England
    I've already mentioned I started when I was about 10 when I secrectly 'borrowed' (stole?) my sisters frilly skirt (she never got it back by the way!).
    But I have seen pictures of me as a baby wearing what is quite obviously a girls dress. Now with me being the first of my generation, I know it wasnt a hand me down, so....?
    Maybe they thought I was going to be a girl and bought some things or maybe they had hoped I would be a girl?... Well they weren't far wrong!

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