Page 6 of 15 FirstFirst ... 45678 ... LastLast
Results 126 to 150 of 372

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

  1. #126
    Member Jerry's Avatar
    Join Date
    Oct 2004
    Location
    springfield
    Posts
    193

    5 with neighbor girls

    I was about 5 when I played dress up with neighbors up the street. I loved the feel and swoosh of a dress. And the mary-janes! I almost can't remember a day when I didn't think about wearing a dress or skirt.
    Hog hugs. Jerry

  2. #127
    Great Legs Tiffanygirl's Avatar
    Join Date
    Feb 2005
    Posts
    126

    Post Stages

    LOL I went through "stages."

    When I was about 5 or 6 I just wore pantyhose. I was at my Pantyhose stage.

    Then at about 11 I told my sister that I CDed, she took it well she even offered like 4 or 5 dresses. I wish I would have taken the offer then.

    Then at 12 my sister was out of town so I decided I'd just try a dress or two on, I loved it so that's when I moved to Dress/Pantyhose stage.

    Then at 14 my sister found out I was trying her dresses on. So she just gave me the ones that I liked. She also had some shoes she'd out-grown so she just said, "Here take em I can't wear them anymore, why don't ya try em on." So I did they were a perfect fit. So now she gives me hand-me-downs every once in a while. Then i was at Dress/Shoes/Pantyhose stage.

    Then one day she came over with a bag full of wigs and make-up. I said, "Ok now I draw the line at make-up." :mad: but she said, "Oh come onnn just try it." So I did, and not only did I love it but I looked good. So now at 19 I'm at my WEAR IT ALL GIRL!! stage.
    Last edited by Tiffanygirl; 02-14-2005 at 09:51 PM.

  3. #128
    Junior Member
    Join Date
    Aug 2004
    Posts
    41

    well...

    I used to dress up when i was younger, rearly though, but last year sometime when i was 18 I was online to a gg i know and she told me that i might look cute in a dress and to send her some pics of me dressed like a girl for a joke so I borrowed some close and did and sent her pictures and from then on i've just been rather into it she says i look rather girly any way lol. But i have troubles dressing up i don't get much privacy so i have to stay up late to do so.

  4. #129
    Great Legs Tiffanygirl's Avatar
    Join Date
    Feb 2005
    Posts
    126
    Quote Originally Posted by Virtue
    I used to dress up when i was younger, rearly though, but last year sometime when i was 18 I was online to a gg i know and she told me that i might look cute in a dress and to send her some pics of me dressed like a girl for a joke so I borrowed some close and did and sent her pictures and from then on i've just been rather into it she says i look rather girly any way lol. But i have troubles dressing up i don't get much privacy so i have to stay up late to do so.
    I HERE YA THERE SISTER!!! (The staying up late part.)

  5. #130
    woman on the inside Ashlee's Avatar
    Join Date
    Nov 2004
    Location
    Central Mass.
    Posts
    338

    age 6 or 7

    i was visiting a cousin who lived down south. i have no sisters (except here!) i always wanted to wear her pantyhose to bed but my aunt and uncle wouldn't allow. i was caught a few times by them during my visits but no harm done. they just chalked it up to my being a kid. i still love the fell of hose on my legs. they're just my favorite clothing item. i m so looking forward to halloween and hope i can get the chance to go out dressed. pm's welcome . have a nice day all!

  6. #131
    Senior Member Melissa A.'s Avatar
    Join Date
    Aug 2004
    Location
    Brooklyn
    Posts
    1,548
    4 or 5 and my sister's clothes. Mom's were too big.

    Hugs,

    Melissa

  7. #132
    Member
    Join Date
    Jan 2005
    Posts
    219
    I was 12 when I first put on my mothers white panties - she caught me and made me suffer for years.

  8. #133
    gurly girl
    Join Date
    Jan 2005
    Posts
    75
    i was probably around 10 or 11. i can remember my older cousins thinking it would be cute to paint my fingernails. i let them paint them dark red and i didnt want to take it off. of course my mom made me. :mad: she said it was for girls. anyway, soon after that i began sneeking into her room when they were gone and trying on all of her shoes and stockings, and painting my toes whenever possible. im sure she knew, but never confronted me about it. im now 23 and still hide it, although i often wear panties and always have my toes done. she has caught me once but never really brought it up. i cant wait to move out so i can dress more often.

  9. #134
    Sometimes demure.... Anne Charlotte's Avatar
    Join Date
    Aug 2004
    Location
    South Wales, UK
    Posts
    172

    At it as long as I can remember

    I started when I was about 6 or 7, but it never really got going until I was in my late teens and able to get time alone at home.

    In my last year in junior school (when I was 10 or 11), it was expected that the eldest class in the school would put on a show at the end of the year. Pupils were allowed a free hand in the what they did, and it usually involved singing or dancing etc etc.....

    Luckily for me, the girls in the class decided that would arrange a spoof beauty contest, and get the boys to dress up for it.......HEAVEN !!

    I can still remember the feeling of wearing my sisters green velvet bridesmaids dress and petticoat and a long brown wig and sache'ing across the school stage in front of over 200 teachers, parents and friends.......god knows what my parents thought !!!

    I also remember being bitterly disappointed that I didn't win the contest !!! :mad:

    What got me really into dressing though.....was my absolute and total obsession with shoes and boots.......if it's got a high heel I gotta have it !!!But if you got heels, you gotta dress. If you gotta dress, you gotta look good...that means make-up, posture, deportment.......it's gotta be right.
    Live the high life.......wear 5 inch heels !!!

    LOL Annie C

  10. #135
    Member Nyx's Avatar
    Join Date
    Feb 2005
    Posts
    313
    I don't know exactly what age I was. My guess would be about 5 or so. A friend of mine (guy) had a box of "disguise" clothes. This included a dress, a wig and a 2 piece bikini set. It didn't look very pretty, but everytime we wanted to play disguises, I couldn't resist the urge to put that on. We even went outside with it to show the neighbors. I didn't understand why they looked at me in weird ways back then. I didn't get sexual arousal from it as I had no idea what sexual arousal even was, but I do remember getting an immense thrill from it... I also remember another friend (girl) of mine daring me to put on one of her dresses, and me doing it...

    When I was 6, I remember asking my mom to buy me a girls swimsuit because I really wanted to wear one. I obviously got the explanation that this was not suitable and not possible.

    I eventually found out this all was considered "wrong" and restrained myself from doing it. Tried moms clothes on few rare occasions when I was 11... Decided not to let it become a habit as it felt wrong to try on my *moms* clothes. But here I am now, at 19... I ordered a full set of clothes last week and I am eagerly waiting for it Those will be my first girl clothes ever!

  11. #136
    crossdresser
    Join Date
    Jan 2005
    Location
    new york
    Posts
    51

    Smile

    I was 8 yrs old.started with mothers clothes. as time went on an sister got older used her clothes, an mothers make up, that was 46 yrs ago.loved every minute of it

  12. #137
    Louisiana girl ginagurl's Avatar
    Join Date
    Feb 2005
    Location
    Louisiana
    Posts
    36

    two realizations

    I was living with a friend of mine in Texas and he had two sisters. I had been living there a month, and my friend and I were in bed. He asked me what I would think if he told me he liked guys and girls. I told him that I didn't know. He said it was true and started coming on to me. I found out I liked it, but I also knew that I liked women as well, so I thought I was wierd. Well, anyway, he and I wound up sleeping together every night. Two weeks later I wanted to surprise him by being dressed as a woman, just to see his reaction. At first it was for him, but once I was all dressed up, I knew it would be for me from then on. I will never forget that night. I'm almost twenty-one now ,and since then I have always worn panties at the very least, sometimes wearing a bra. It's not a sexual thing for me, but it does have its memories. Fortunately I know a couple of bi guys and one gay guy who are all clean, and every so often we'll get together. I'm considering dressing for them too.

    ginagurl
    Is it an illusion, or is this girl I see really me?

  13. #138
    It's bigger on the inside alba68's Avatar
    Join Date
    Dec 2004
    Location
    Leigh
    Posts
    586
    [size=3]I was about 11 I think. Wore my sisters tights and was hooked from there. Been doing it on and off ever since.[/size]
    Take care.
    [size=5]Alba.[/size]
    I'm not scared of dying, I just don't want to!

  14. #139
    Member ToniB's Avatar
    Join Date
    Jan 2005
    Location
    NW England, UK
    Posts
    278
    About 11 or 12 I think (nearly 50 years ago now). Tried mother's knickers and bra at first, and that gave me the first erection I can remember. I was trembling with the excitement. Then I found her hook-side girdle. It was really tight to put on, and the pressure on my penis inside it was really exciting. I found the rhythmic bouncing on the floor doing press-ups intensified the feeling until I had my first (accidental) orgasm. I have been hooked ever since, even though it took a long time to clear up the mess well enough for her not to notice.
    Has anyone else got a more bizare "first orgasm" story?

    Toni

  15. #140
    sweetsamanthacd
    Guest

    He was only 13, too young to fall in love!!

    I started when I was 13 it was part of playing truth or dare with my girlfriend at the time she dared to try on her panties and I did...

  16. #141
    Aspiring Member Fiona K's Avatar
    Join Date
    Oct 2004
    Location
    Edinburgh, Scotland
    Posts
    837
    Initially younger sister's clothes, I was very small for my age and could just get into them, around 10 years old or so. I loved her Guide (Girl Scout) Uniform. The as I grew I discovered some old clothes of my mums in a trunk in the attic, 50s and 60s stuff, most she'd made herself. As I discovered at 15 I was a perfect size 6-8 petite (not anymore sadly) and was entranced by the full 50s skirts. What was missing was underwear.

    This was solved by the fact my father was a sales rep for a corsetry company!?!?!?!? Teenage CD heaven or what?

    So I "aquired" some samples; Girdles, Corsolettest panty girdles etc. Wore the dresses, stockings corsetry the lot and was over the moon-----------Then got caught!!

    That's another story!
    Fiona
    xx

  17. #142
    Junior Member
    Join Date
    Jan 2005
    Location
    Melb
    Posts
    91
    My own story started when i was such a wee boy. My mum and dad both worked hard to keep a roof over our heads so as children, me and my bro's had to spend all of our time (when we weren't at school) at our grandparent's place. It was there that I had my first ever cross-dress experience. I would have been no older than 6 or 7. I was exploring in the garage and came across an old bag of clothes.... and in it i found (amongst other things) a white dress, lots of frills and lacey stuff..... i don't even quite know why, but i felt driven towards putting this damn dress on. I can remember feeling very sneaky about the whole thing. I knew (or at least i felt like) that it wasn't the right thing to do. But, when i put that dress on, ****wow*** what a feeling. Even a strange squirming in my loins. I kept that dress on for as long as i dared, but eventually (and feeling very guilty) i quickly got out of the dress, got back into my clothes and put the dress back. I quickly forgot about that bizarre incident. In fact, I even completely blanked it out of my memory for several years.

    It was not until my mid-teens that I suddenly remembered that bizarre childhood incident. I had wagged school for the day and was daydreaming on my way home.... when it suddenly dawned on me... I quickly raced home (no-one home during the day) and raided my mum's panty draw..... my god... what a terrible thing to do to my own mother... but at the time... i didn't even think twice about it. In her bedroom she had a massive mirror, i spent quite some time in front of that mirror in various undergarments. And that feeling in my loins was back again.
    Derminator - wishin to be someone else, some of the time!

  18. #143
    roberta cdgirl's Avatar
    Join Date
    Dec 2004
    Location
    blakeslee p a
    Posts
    87

    Smile the happiest day of my life

    hi everyone i was 12 when my curiousity got the
    best of me ,yes i tried moms lycra panty girdle and
    seamed stockings an latex bra on. yes you better
    believe the best time in my life when i decided to
    wear them and from that day on you got it i dont
    want to ever stop wearing them. yes age 12 was
    a good year for me 1963. huggs cdgirl.
    my fem clock is racing and i need to catch up.im not getting any younger.someone please help me.

  19. #144
    Member Claire B's Avatar
    Join Date
    Dec 2004
    Location
    N.E. Florida
    Posts
    104

    How old and whose clothes.

    I think I was around 11 the first time I dressed as a girl. My step sister who is a year older than me. Dressed me fully in her clothes, including her make up also. This was kind of like a payment for keeping her from getting snake bite and I guess saving her life. When i was that age, I wore my hair to just below my shoilders. So the hair wasn't any problems. It just needed styling. From that day on if she was at home and we were alone she would dress me and taught me how to be feminine. If she wasn't at home and knew that I would be. She would lay out clothes for me to wear. I am now 55 years old and dress as often as I can.

    Hugs and Kisses, Claire

  20. #145
    Aspiring Member MonaSmith's Avatar
    Join Date
    Nov 2004
    Location
    Croydon, Surrey, England
    Posts
    765
    Quote Originally Posted by Fiona K
    Then got caught!!

    That's another story!
    Fiona
    xx
    Well!! you can't leave us hanging like that Fiona. Start a thread, anything!!

    Anyhoo, I was about five or six. I used to put on my older (by 2 years) sister's ballerina outfit. I secretly wore her clothes until I was about 14.

    Mona xx.

  21. #146
    "Stephanie"
    Join Date
    Dec 2004
    Location
    SE Va
    Posts
    347
    That's interesting about the ballerina outfit, Mona. My first experience was with my older sister's bedroom slippers, which I fancied for ballet slippers. Age:about 6.
    Love,
    SilkenPrincess

  22. #147
    Aspiring Member Fiona K's Avatar
    Join Date
    Oct 2004
    Location
    Edinburgh, Scotland
    Posts
    837
    Quote Originally Posted by MonaSmith
    Well!! you can't leave us hanging like that Fiona. Start a thread, anything!!

    Anyhoo, I was about five or six. I used to put on my older (by 2 years) sister's ballerina outfit. I secretly wore her clothes until I was about 14.

    Mona xx.
    No big deal Mona, really!!
    Mum found my stash when cleaning my room when I was around 15, she never said a word to me but my dad summoned me for a private talk. In those days I thought I was the only one and had no idea how to describe what I was doning or why. I just promised that it would stop.

    A promise well and truly broken within a couple of months, I just got much better at hiding stuff!!!

    Fiona
    xx

  23. #148
    Junior Member Monique_Lynn's Avatar
    Join Date
    Jan 2005
    Posts
    60
    I started at around age 4,(BACK IN THE MID 60s) At the time my next younger sibling was diagnosed with cerebral palsey and my parents spent many week ends away from home in search of help for in caring for him. I always went to my widowed aunts house to stay while they were away. Ended up living with her almost full time as things went on. My aunt had no children of her own. At night she always wore very pretty silky night gowns and would cuddle me in next to her while she read to me till I fell asleep. There were never any sexual advances on me by my aunt but as time went on I found the feeling of the nylon to be a soft warm well you know a good feeling. Well my aunt caught me several times in her lingerie drawers and eventually bought me my own night gown and panties that I was allowed to wear to bed but I had to promise not to tell and to stay out of her stuff. I suspect perhaps she my have always wanted a little girl of her own because as time went on the guest bedroom was turned into my bedroom and was decorated in a feminine decor. Also along with my boy clothes, there were also girly clothes and I was allowed to play dressup when ever I wanted as long as I didn't go outside (RAINY DAY FUN) As I got older I started to notice other things as well, watching my aunt getting dressed, rolling her stockings up her legs and the shoes!!! So of course I had to investigate and found the feeling of stockings and heels, Incredible!!
    When puberty started to hit, Oh boy couldn't get enough of the feeling of dressing but also felt weird (OMG) I bet I'm the only one!! I was like 11-12 at this time. (EARLY 70s) Also about this time a new family moved in next door, 2 boys , one my age and his older brother by five years, well the two of us soon became best friends and were pretty much inseperable, sleep overs at each others house etc. My friend and I discovered his brothers stash of penthouse magazines one day (HEAVEN) , one thing lead to another and another. I eventually confided in him about likeing to dress up and wanting to be a girl. My friend ended up being my first sexual partner (NO REGRETS).
    Abandoned crossdressing in my late teens as much as I could??? Dated, married, divorced,returned to crossdressing(MID 80s), remarried and still am, Was very up front and open with my wife early on (NO SECRETS). She is very supportive and understanding and knows ginger and I are one. neither can live with out the other.
    Sorry about the long post, hope this helps others to maybe understand.
    ginger lynn

  24. #149
    New Member Rui_Bristol's Avatar
    Join Date
    Feb 2005
    Location
    Bristol, UK
    Posts
    24
    i started dressing when i was about 10-11 years old.

    i was round my friend's house but he had to go out and left me on my own there and i decided to go into his sister's room and just found myself trying ona pair of ankle boots and a tight dress from her wardrobe.

    ive been dressing ever since.

    im 18 years old now

  25. #150
    New Member
    Join Date
    Feb 2005
    Location
    Western AZ
    Posts
    14
    I started at age 12, out of idle sexual curiousity....tried on mom's panties and bra, and was enormously aroused - even at that age I knew it was 'taboo'! After that, I dressed in her undies whenever I had a chance, and she never knew (at least that I know of).

    I had a huge crush on my best friend's mom, and absolutely lusted over her more-than-ample breasts as my teen hormones raged within me. I used to house-sit for them all the time when they went on vacation, which left me many summer vacation afternoons alone with her lovely bras and underwear while they were gone. It was a tremendous rush for me to see and feel 'her' big boobs on my chest! He (my best friend) and I spent a lot of time masturbating while looking at his dad's girly mags, and one thing inevitably led to another - with the result being that we "experimented" sexually with each other all through our early to mid-teens. I dressed in his mom's bra, panties and high heels a few times during those 'sessions', and I've never been quite sure which one of us enjoyed it more!

Posting Permissions

  • You may not post new threads
  • You may not post replies
  • You may not post attachments
  • You may not edit your posts
  •  


Check out these other hot web properties:
Catholic Personals | Jewish Personals | Millionaire Personals | Unsigned Artists | Crossdressing Relationship
BBW Personals | Latino Personals | Black Personals | Crossdresser Chat | Crossdressing QA
Biker Personals | CD Relationship | Crossdressing Dating | FTM Relationship | Dating | TG Relationship


The crossdressing community is one that needs to stick together and continue to be there for each other for whatever one needs.
We are always trying to improve the forum to better serve the crossdresser in all of us.

Browse Crossdressers By State