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Thread: When did you first crossdress?

  1. #101
    Extraordinaire May(be)'s Avatar
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    When I was 6 or 7 I was running around the house in my mom's nightgown, shoes, and earrings and I didn't think anything of it. My mom had to remind me of that memory. I had totally forgotten until she told me about it when I talked to her about my crossdressing.

  2. #102
    Member Leighcdmd's Avatar
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    The earliest that I can remember was dressing in my mother's slip at about age 8. Supressed it during high school and college but reemerged in my twenties.

  3. #103
    Claire Claire Cook's Avatar
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    Quote Originally Posted by Alexandra Santora View Post
    Thanks to all for responding - I've really enjoyed reading everyone's recollections. It's curious that what started at an early age just doesn't go away.
    No, it doesn't, does it? That's why it is so great when we just accept it -- and enjoy it.
    [SIGPIC][/SIGPIC] Proud member of the Lacey Leigh Fan Club

  4. #104
    Member phlover's Avatar
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    Quote Originally Posted by Alexandra Santora View Post
    Thanks to all for responding - I've really enjoyed reading everyone's recollections. It's curious that what started at an early age just doesn't go away.
    I agree.
    My crossdressing started when I got the stockings of my friend's mom at around 10 or 11.
    They were really sheer as if I wore nothing on my legs, and the feeling was really fantastic.
    My wearing stockings moved to wearing thigh-highs, and then pantyhose.
    I became really enamored of pantyhose after lycra was used for pantyhose and I was hooked to the tight feeling of the pantyhose.
    Later, my crossdressing developed into wearing girdles, shapers, short mini-skirts and high-heels.

    Several times I tried to purge my feminine clothes and heels and resolved not to wear girly clothes anymore.
    But the urge returned one after another, and I couldn't shake the desire away.
    I finally compromised with my urge to crossdress, and it develops into deeper stages as time goes by.
    I recently began to shave my pubic area and tuck using sports tape, and I don't know where my crossdressing would go further.
    Maybe makeup and wigs and so on....

    I am typing this reply wearing nude pantyhose, mini denim skirt and grey stilettos with 4.5" heels.
    I LOVE the feeling!

  5. #105
    Flip a coin... Nikki50/50's Avatar
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    Many variables, here.
    Crossdress without acknowledging that it was 'different'? Without knowing even?
    Or willingly pulling on the stockings, skirt, bra, etc...knowing full well that such was
    considered a deviant behavior by most social standards?

    Fist time was 6 or so. Summer dress to be a gift for my cousin, but the hem needed to be taken in so the dress would fit her. I got to be the manequin model for a few hours.
    I remember that it felt...not quite right, but not wrong, exactly either. I didn't question it, I saw the need and accepted it. Besides, I was paid for my time by a huge sack of swedish fish by my Granny.

    When did I willingly and knowingly dress the part of my female side? THAT is an epic stroy yet to be told. I am awaiting permission from the moderators to tell it.

  6. #106
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    It was the mid 60's, I was 10, and my mother used me as her wig stand to comb out and style the short haired wig she had. I hated doing it.

    But she also took in laundry and did sewing and alterations. So when I was 12 I got used as the dress model and protested each time, but I secretly started liking it.

    In the name to get the job done and make money , my mom thought nothing of having me wear a stuffed bra. Or sometimes a girdle and nylons to make the shoes fit better when doing the hem. I enjoyed every bit of it.

    However, I started showing too much interest in the part ( shaved the fuzz off my legs and would stay in the lingerie a little too long after finishing the fitting) and it came to an abrupt halt. One day mom showed up with a dress form from a second hand store and I was done. No more dressing, at least not that she knew about.

  7. #107
    Senior Member Christie ann's Avatar
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    I have been cross dressing or wishing I could cross dress ever since I can remember

  8. #108
    Member katlee's Avatar
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    I didnt start crossdressing until I got a GF, but prior I would sometimes tuck when I got an urge similar to the stories I would read at ss.
    I think I feel more like Natalie than I do Kat. I think from this point I will go by Natalie.

    Part of a recently ended relationship where a reason why it ended was my crossdressing.

  9. #109
    Junior Member FoxxxyBri's Avatar
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    I was about 7 years old and my Mom put a little girl's dress on me as a joke. I have no idea if that influenced me or not. But at the age of 12 I put on her stockings before I masturbated the first time. After that I slowly turned into Brianna...

  10. #110
    Senior Member Sarah V's Avatar
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    Putting on me mums pantyhose that she would hang in the bathroom after taking them off. I was around 6 ys old at the time. Shortly therafter I tried on one of my sisters body suits. That was it, I've been hooked on womens clothing ever since. (Sorry Nancy Reagan, I could just never say "No" to ladies things!!)


    Sarah[SIZE="3"][/SIZE]

    "Sport is for men.......But Ballet is for women" ---- George Balenchine

  11. #111
    Member adrienner99's Avatar
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    I was 8 or 10 when I started to pretend to be sick and stay home from school. My mom didn't work but she'd often go out and I would have time to dress..I believe the first outfit of hers I tried on was a yellow silk evening dress with a bow in the back. She also had a champagne cocktail dress I would wear with a petticoat. I wore her black patent three-inch heels (way too big) and her clip on diamond earrings. Then I would sit at her vanity and put on her Revlon's Cherries in the Snow lipstick. Sometimes I would put on her short, white gloves...Even today it is hard to describe how blissfully happy, peaceful and excited I felt. I also pored over her women's magazines, particularly the shoe and lipstick ads....Ladies Home Journal, McCalls and Redbook...now of course I like Vogue, Elle, Allure, InStyle, Glamour...

  12. #112
    Lacy Lacyfem's Avatar
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    My first time dressing was when I was 10 in my mom's panty, bra, hose and heels and it was also the first time I tasted alcohol and got drunk. Parents had a cocktail party before going out to dinner with friends and as soon as they were out of the house I started to try my Dad's bourbon. As I got tipsy something clicked in my mind and I went to the hamper and put on Mom's full cut nylon panties and bra, pulled out some nylons and slipped into a pair of her heels. It was a feeling that I can remember till this day. I so enjoyed being dressed and walking around our yard in the evening feeling fem but very drunk and excited. I ended the evening throwing up from the booze which wasn't fun and my mom knew about that the next morning but don't think she knew I was in her lingerie and nor did she for the rest of my years at home till I went to college.

  13. #113
    Member Kalista Jameson's Avatar
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    When did I first crossdress?

    Last week. I was actually looking for a World of Warcraft PvP guide for my Blood Elf Rogue, redirected here and got inspired.

    Lol, joking. Bad humor...

    The first time I remember was playing with my sister, three years younger than me, I was around ten or eleven, and putting on her ballet tights and leotard so we could be super heroes. I stuffed a pillow case down the back of the neck for extra effect. Then I discovered pantyhose....

    Life has never been the same. I blame the Super Friends for this.

    Cheers,

    Kalista

    I'm a TGirl, yes it's true! I'm a TGirl, through and through.
    I love nylons and high heels, mini-skirts and shopping deals!
    I don't care what others say, life's too short, it's time to play.
    I'm a TGirl, yes it's true! I'm a TGirl, how 'bout you?

  14. #114
    Of Course They're Real! Buxom Fella's Avatar
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    On purpose?

    Twelve or thirteen, don't remember exactly when. I know I was 14 the first time I went out like that.

  15. #115
    Discovering the Gurl Xandra's Avatar
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    Quote Originally Posted by Nikki50/50 View Post
    Many variables, here.
    Crossdress without acknowledging that it was 'different'? Without knowing even?
    Or willingly pulling on the stockings, skirt, bra, etc...knowing full well that such was
    considered a deviant behavior by most social standards?

    Fist time was 6 or so. Summer dress to be a gift for my cousin, but the hem needed to be taken in so the dress would fit her. I got to be the manequin model for a few hours.
    I remember that it felt...not quite right, but not wrong, exactly either. I didn't question it, I saw the need and accepted it. Besides, I was paid for my time by a huge sack of swedish fish by my Granny.

    When did I willingly and knowingly dress the part of my female side? THAT is an epic stroy yet to be told. I am awaiting permission from the moderators to tell it.
    I hope you get permission to tell your story; I'd love to hear it.

  16. #116
    One Nerdy Bitch CarmenSkye's Avatar
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    I first tried on my cousins dress when I was 7, but I didn't fully dress until about a year ago.
    Done crying.

  17. #117
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    There's a photo of me, about 5 or 6 wearing my mom's one piece swimsuit. In my early teens I used to be jealous of the girls I knew and wondering what it was like if I was born female. Then in high school I started wearing my sister's clothes and experimenting with hers and mom's makeup. And thus Savannah was born.

    Cheers.

  18. #118
    Flip a coin... Nikki50/50's Avatar
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    Quote Originally Posted by Alexandra Santora View Post
    I hope you get permission to tell your story; I'd love to hear it.
    I hope so too...I approached the moderators about it, and I was asked to private message the first draft to get the OK...but every which way I try to encapsulate it, it ends up being damn close to novel-length. Still whittling it down...

  19. #119
    New Member Julia Stevens's Avatar
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    I tried on my sisters black high heeled boots (she was 9 years older than me, they were up to the top of my thighs!) when I was about 8. I used to put her bangles over my ears as earrings and carry her shoulder bag. She thought it was cute. Not long after in secret I tried on her engagement dress, which was also far too big for me. After that it went on to my mothers clothes, bras, lipstick etc (I loved my mothers lipstick), this was also in secret.

  20. #120
    Discovering the Gurl Xandra's Avatar
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    Hi Nikki,

    Any news on your story?

    Alexandra.

    Quote Originally Posted by Nikki50/50 View Post
    Many variables, here.
    Crossdress without acknowledging that it was 'different'? Without knowing even?
    Or willingly pulling on the stockings, skirt, bra, etc...knowing full well that such was
    considered a deviant behavior by most social standards?

    Fist time was 6 or so. Summer dress to be a gift for my cousin, but the hem needed to be taken in so the dress would fit her. I got to be the manequin model for a few hours.
    I remember that it felt...not quite right, but not wrong, exactly either. I didn't question it, I saw the need and accepted it. Besides, I was paid for my time by a huge sack of swedish fish by my Granny.

    When did I willingly and knowingly dress the part of my female side? THAT is an epic stroy yet to be told. I am awaiting permission from the moderators to tell it.

  21. #121
    My name is Carol Julogden's Avatar
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    Probably 3 or so. My mom had an old net petticoat that she gave me to wear, and I wore it a lot and I also got into her makeup and tried to put it on whenever I got the chance. I also clumped around in her shoes a lot when I was very little.

    I didn't try on other stuff of hers that I can remember until I was old enough to be left alone at home for a short time, probably 8 or 9. I remember the first time I tried on a pair of her nylons when I was way too small to fill them out, they were very baggy on me, but I still thought they looked great. I used to try on her nightgowns too. By age 11, I was too big to fit into her clothes, and I was very unhappy about growing so tall at such an early age.

    Carol
    My name is Carol.

  22. #122
    Aspiring Member Stevie's Avatar
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    The first time I remember was in my teens trying on my moms boots, but disinterested really start until my college days and the temptation grew slowly from there.

  23. #123
    Member Helen 2's Avatar
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    In my case , Mom. in 1961, my sister died when I was 9, she 11. Tore my mother to pieces because it was her fault...she miss-diagnosed what was pneumonia as a slight cold, by the time my sis was diagnosed, it was too late. Mom spent weeks in a mental institution and was in bad shape for many months. About two years later, once day at home Mom asked me to dress in my sisters' clothing and I of course said no, which made Mom cry in huge, heart-wrenching sobs, so...very concerned form her mental state, I grudgingly said she could -and I loved it. Spent the day in a frilly dressy, training bra and one of mom's girdles to give me some shape - and I loved every minute of it...it was so different, so much a discovery so......natural.
    Two weeks later, she asked me again and I did not argue. A couple weeks after that I asked her and she beamed with happiness. From then on, as long as we were alone, I could be Helen as much and as long as I wanted to.

  24. #124
    Flip a coin... Nikki50/50's Avatar
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    Quote Originally Posted by Alexandra Santora View Post
    Hi Nikki,

    Any news on your story?

    Alexandra.
    It was suggested that I should tell it in fragments, over several posts. 'Chapters', if you will...
    I am currently writing out my crossdressing origin/history in longhand, and as soon as I chop it into segments (and and spell-checking...and grammar checking...lol), I will begin typing and posting them. One every other day should do it. No worries, it is coming...

  25. #125
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    I was 13 the first time. I found one of my sisters skirts in the hamper and had wondered what it felt like to wear a skirt for a long time,I figured it is now or never and put it on. After only a few minutes I thought it is not normal to be wearing boxer shorts with a skirt and went to find a pair of panties, then relised my boys shirt looked awful with the skirt so had to find a blouse. I was fortunate to have the house to myself for an hour or more every day at this time, so I got to dress up for an hour after school for at least an hour. But that wasn't enough for me I started wearing panties to school everyday as well.

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