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  • #259443
    Peggy Sue Williams
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    Registered On: June 26, 2019
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    What is you earliest memory of cross dressing?

    My mother told me I got into her makeup and tried making myself up, when I was around two years old, and I can recall walking around in my mom’s shoes sometime from age three or four and up.  The memories are very fuzzy, but I recall sometime around the same age, three or four, starting to play dress up with the girl my age who lived across the street.  That continued up to my preteen years and ceased only when my family moved away.  She delighted in making me her “girlfriend,” and I loved it!  I recall asking, when I was in kindergarten, if I could sometimes wear girl’s clothes to school but was sternly told no, by my parents.  At seven or eight, I played the part of a ballerina in a cub scout play, and I recall wearing make up and wearing a pretty pink outfit, from head to toe.  That was a watershed event, because I clearly remember how so many adults kept telling me how pretty I was. I was absolutely hooked on wanting to look pretty, often! These are some of my earliest memories, but like most of us, our CD activity continued nonstop throughout our lives.

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    • #372220
      Michelle Bailey
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      Hi girls

      I think I was about ten when I took an interest in mum’s undies ,girdles,panties and stockings, bras came a lot later , I started my own collection of her old underwear and kept it in a cupboard in the playroom in the attic , also tried on my sisters underwear ,eventually my stash was discovered ,what could I say ,I said I used the underwear to pretend to be a spaceman ,don’t think my parents believed me ,so all had to go .What could I do, so started wearing mum’s things when I was alone in the house and putting them back ,I was in heaven ,about that time a family moved in next door ,they had two daughters a little bit older than me ,I used to watch when their mum went off to the shops on her bike and the house was empty ,there was a side window that had no latch ,so I would climb  make for the girls bedrooms and find their underwear draw and borrow some items (no bras) and go onto the landing where I couldn’t be seen from outside and have a lovely dressing up session ,couple of times borrowed some girdles ,panties and stockings took them home and returned few days later ,did they ever notice the missing underwear ? that all stopped when they moved away

      That girls was the start of my CD life     Miche

       

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    • #372207
      Erin Mondale
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      Later in my life 8 years ago.Started with trying on an ex girlfriend’s clothes on.This was when she was gone at work.I loved wearing her clothes and did make mistakes doing it.I didn’t put them back right,she noticed it including stretched a little bit.Finally one day I told her and she wasn’t too happy with me.Argued and she left,broke up the next day.

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    • #372192
      Diane Crow
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      As I think back on my life, in my youngest days I loved looking at my moms Glamor mags and the Sears and Roebuck catalog looking at the cloths, shoes and undergarments. I loved the style and design. I would even try on my moms panty hose. I loved the feel back then. I loved the grandeur of the cloths and well just everything about it.

      Hugs

      Diane

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    • #372178
      Joanne Jackson
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      I was 8 or 9 playing in the attic and found a box of my older sister’s clothes.  Heaven!  My thoughts and feelings had always been female but that box in the attic brought them to full flower.  Hmmn, flowers in the attic?

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    • #337889
      Bettylou Cox
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      I had no mom or any female relatives; but when I was about 10, I had twin girl playmates, who would play Tarzan and Jane, and they changed the script to make me Girl instead of Boy.  They provided the dress, which I didn’t mind wearing, and thought nothing about it at the time.

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    • #337888
      Deborah Sullivan
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      I loved all the disney characters as a child like cinderella and found myself playing with my sisters barbie dolls as much as she did. I loved dressing her in different outfits and arranging her hair. By the time of puberty I was trying on sisters and mothers bras and makeup when home alone.

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    • #337783
      Katie Collins
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      I used to really fancy women on TV or in magazines who had red lipstick and lots of blue eye shadow. I would lock myself in the bathroom with my Mum’s make up and apply it really badly. I was too small to reach the mirror on the wall so had to balance with one foot on the sink, and one on the radiator.

       

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    • #337767
      Amanda Woods
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      For me probably very early teen years, I found a small slip and bra and tried them on and been in love with women’s clothes ever since.  I used to sneak into my mkms makeup and try her dresses on, still not exactly sure why, but all I know is that I enjoy it and thank god I have a wife who let’s me be who I am.

    • #337755
      Erika Jones
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      I was 11 years old. My next door neighbor asked me to come to his house to help him with some chores. I had done this before. I moved a few boxes changed a light bulb for him ( he was kind of old). Then he asked me if I would do one more favor for him. He said he had bought a sundress for his grand daughter. He asked me if I would try it on so he could see how she would look in it. We were about the same size.  I went in the bedroom, took off my clothes except my underpants, put on the dress. It was a little bit low cut, backless and about 6″ above my knee. I walked up to him sitting on the sofa. I got to experience what a girl does. I watched his eyes go up and down my body, focusing on my legs. It was such a turnoff!!  He said his granddaughter couldn’t wear it because she did not have pretty legs. He said I could wear it anytime I wanted. That’s all that happened on that visit, but next visit he took out his penis and masturbated looking at my legs and up my dress.  I loved it!!

      • #337854
        Jennifer McCrennaugh
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        Erika, what you are describing is sexual assault, not crossdressing. Why is this here?

        -Jen

    • #337352
      Susan Dresser
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      my first memorys was looking in cataloges and thinking how much better womens clothes looked, then when i was about 12 years old a family moved close by there was a boy my age and we became good friends but he had a sister who was a year older than me and she would wear these lacy dresses and i thought that she was the most stunning thing i had ever seen and so much wanted to wear her dresses, so one day we were all playing together at there house when there parents said that the family had to go out, i said that if they liked i would tidy up the things we were playing with then leave, they agreed, after i had cleared up the toys and the like i relised that i was in their house on my own so i went to the sisters bedroom and started looking at her clothes and came across the lace dress and i felt that this was going to be the one chance to see and feel what it was like to wear that dress, so i found some of her underwear and put it on and then the dress! i felt so amazing that i knew that i truly wanted to be a girl, after putting the clothes awayand leaving i knew that i prefered dresses so when the chances arose i would buy a dress and hid it in my room and when my parents went out i would put on my dress,

    • #275107
      Paula1
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      My first time that I can remember is when I was about 5 or 6 at my cousin’s house I would always want to play dress ups there and were her cloths, Then as I got older I would grab some of mums cloths and then the first time I went out was when I was 16 on a cruise with my parents we had a dress up night and the two young ladies and one of the other kids dressed me up as a women and I loved it

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    • #275078
      Anonymous
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      My 1st memory is very fuzzy, I used to change clothes wit my sis aged 5 or 6. The clearest memories are dressing in my cousins clothes around 10-11, she caught me in her bra and panties (doing a very teenage boy thing!) but she was accepting and helped me dress and learn how to do make up when we had a chance. Love her.

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    • #274947
      Chloe Helfers
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      When I was in middle school, my two best friends, who were girls, made me dress up. I put on a bra, mini skirt, and a top I can’t remember. I instantly loved it. They did my make up perfect too. When they said “awww what a pretty girl” I loved it ND knew I discovered what was missing from my life. We did it all the time, and through out the years I would always let girls dress me up and take pictures. That was a mistake though, eventually pictures of me posing went all around my high school, everybody just assumed I was gay. I’m over it now, cuz I’m alot closer to being gay then straight, even though I’ve only done things with a guy once. It was exillerating though to feel so pretty, now that I’m older I can dress when I want. When I dress up, I get to be myself.

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    • #269352
      Anonymous
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      First memory very fuzzy. Just remember at tish putting on underwear, skirt and shoes and liking it. Hooked. Continued to do so over the years, all to big but didn’t care. Think I was 13 or so before sizes aligned. Great times. Years later still hooked.

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    • #269340
      Anonymous
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      I was about 7 years old. My sister and I were home alone. She wanted to play dress up and pretend she had a sister. She dressed me in a dress and put clips in my hair. I loved it and have worn woman’s clothes since.

       

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    • #268618
      Lynda Charles
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      My mother sewed and when she sewed, I ended up being her mannequin. For dresses, blouses, skirts, etc.  For dresses and blouses, I had to be outfitted with a bra so the blouse would drape properly.  And as far as I already had a bra on, she would also apply makeup, lipstick, and clip on earrings, to complete the picture.  And now I assume she also had the temporary daughter she always wanted.

      The first time this happened, I hated it.  The second time, not so much.  I don’t remember exactly when it happened, but I started to look forward to these “sessions”.

    • #267891
      Brittney Andrews
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      I’ve told my first experience with women’s clothing on other posts, and I’m happy to tell my story again.

      I was 8 or 9 years old. I had a grand aunt that I visited often. One day I found 3 pairs of nylon panties in a dresser drawer in her spare bedroom. I asked her if I could try them on, immediately I was hooked. This led me to ask if I could explore the rest of her dressers and closets. She allowed me to choose from her dresses, slips, and panties and we put everything into a large box under her bed. Whenever I’d spend the night at her house, I could get into the box of clothes and we played “dress up”. This continued until she passed away in 1983.

    • #264977
      Sammy Z
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      My sister always wanted a little sister. So when I was about 5 or 6 she started dressing me as her sister. She loved it I loved it.

    • #264957
      Gina Perone
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      And the jcpenny catalog too. My one grandmother moved in with us and she brought a collection of stockings from the 50’s&60’s with real rago girdles. Man was I in heaven!

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    • #264327
      Amber Jamies
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      when I was about 12 or 13 wearing my older sister’s shorty short cut offs and tank top to go swimming at the beach. I was at the age I really didn’t care what anybody thought and I’m at that age again!

    • #262339
      karley delaware
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      My earliest memory was when I was 7 or 8.  I saw a movie on TV with Greek Goddesses and made an outfit for myself from an old remnant bed sheet.  I “borrowed” my mothers black scarf to be my hair.  In my play, I was a little girl and the boys were all so nice to me.

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    • #261590
      Jin Crocker
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      I grew up in girl clothes. We never had any male clothes in the house until I started school. I have always been open about fashion. It would truly be a kinder, gentler, world if everyone dressed by activity instead of gender rules.

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    • #261370
      Val Siera
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      a person knows what is right for there body, when the clothing reveals the inner person then that person was always there, just needed the nudge. thank you so much for your thanks, over time we may be able to share more, please consider me a sister traveling through the trials of being yourself.  I am 61  now and have manage to retain pretty decent shape, I can dress  and dress up with decent appearance, now just trying to maintain my dignity as a mature “girl”. would love to here more from you.

      Val

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    • #261364
      Val Siera
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      7 years old, tried on sheer silk stockings hanging over the shower bar, medium black, got very exited at the idea of being a girl, never looked back.

    • #261310
      Nobody Atall
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      Well my first memory would be trying on my mother’s heels or getting dressed up but one of my favourite first memories i was 17 and left home alone for 3 days while my family were still away. I first went shopping and got myself a lovely dress and a bra, panties as well as a new skirt and some more pantyhose. Once i got home i immediately put on my bra then dress and went to the backyard to paint my nails. After doing my yoes and fingers bright red i started doing my makeup. I just started living as a girl, at one point i needed to go down to the shops so i went dressed as a guy with my bra, pantyhose on underneath. But i did have my bright red fingers showing (for the thrill) while in the supermarket i ran into some people i knew and immediately left the store out of fear haha. I just remember getting home and loving life

    • #261006
      Kimmie
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      Oh. Me too.

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    • #260933
      Peggy Sue Williams
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      Ahhh, yes, so many memories of pouring through the four-inch thick Sears mail order catalog and oogling the women in girdles, bras, and stockings.  As a pre-teen boy, that catalog provided endless ideas on how I wanted to dress up as a girl.  Memories!

    • #260882
      Erica Gutkowski
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      My earliest recollection of CD activity was being intrigued by the pictures of women in catalogues wearing their underwear.  Eventually, curiosity got the best of me, and I had to try a bra and panties myself.

    • #260763
      Anonymous
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      I was perhaps 12 years old visiting family in Switzerland. I nabbed my cousin’s black wool tights and once, while in the bathroom, put them on. It was an interesting experience, combining the taboo with the thrill of something new. I have no idea what prompted me to even do what I did, but I assume it had something to do with exploring sex (not gender) while undergoing puberty. Such events can really shape the way a person thinks about sex, leading to fetishes and the like. Anyway, that was the earliest memory I have, and this event planted the seed that eventually bloomed into my Alex persona.

    • #260326
      Kimmie
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      At a young age, I began playing “doctor” with a girl on my street who was my best friend and two years older. We played like that for a couple of years and, over time, became more and more daring. Once, one of us suggested swapping underwear when we went home and change back the next day.

      I don’t remember any special feelings from doing that, but once we stopped playing those games with each other. I discovered my mother’s lingerie drawer. I think I started trying her things on and got the same type of “feelings” as I had playing doctor. From there, I was hooked.

       

    • #260272
      Patty Phose
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      I was 4 and wearing stockings my mother gave me with a pair of heels I borrowed from her. I was having trouble keeping the stockings up. My grandmother tried to tie up the stockings to keep them from sliding down but they still did. I don’t remember if it was my other or grandmother who suggested pantyhose would be better for me.

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    • #260268
      Lee Ann Rakers
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      Easy. I was maybe 8 or 9 and wearing my mother’s stuff. I ALWAYS had her permission.

      I have never had any guilt or shame about dressing. I owe my mother a huge thank you. Someday Mom.

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      • #260858
        Bobbi
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        Mine too! Bless our mothers! Daddy was a little slow to come around, but he did.
        Now, I’m a total “Daddy’s Girl”! Nobody dared to mess with me when I was a teen.
        (Daddy would have killed them!).

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    • #260213
      Peggy Sue Williams
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      Thank you Cindy, and I see from your profile that we are sister Georgia girls!

      I live in Marietta, Cobb county.

       

      Hugs,

      Peggy Sue

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    • #260137
      Cindy Jones
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      Hi Peggy Sue,

      Thanks for bringing up this topic.  For me, the first time was Halloween when I was 10 years old.  How appropriate, right?  On our crossdresser’s national holiday!  It is so vivid in my memory.  I had never shown any interest in girly things up to that point, but for some reason my mom thought it would be a hoot if she dressed me up as a girl.  So…  she dressed me up in a short skirt, pantyhose, go-go boots, tight sweater (with boobs that were way too big), wig, and makeup.  Of course I protested vigorously, but secretly I was loving every second of it.  We went out, house to house, walking the neighborhood… it was exhilarating.  I was hooked!!  It was even better when several of the neighbors didn’t recognize me and commented on what a pretty girl I was (maybe they knew, but I didn’t care because I was loving being complimented as a girl).  Again, I was double hooked!!  And…  I’ve had our shared desire to dress ever since.

      Luv, Cindy

      PS – Like any family, we took pictures of the costumes that night.  I consider myself very lucky that I still have one of the photos.  How many CDs have a picture of the very first time they dressed?

    • #259855
      Anonymous
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      My dressing goes back probably as far as I can remember. I remember wearing my sisters bright shiny satin dance costumes and just loving it at probably age 5 or 6. There was never a shortage of clothes for me having 3 sisters.

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    • #259773
      Jillian Walker
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      Wow, so many stories!  When I was 11 or 12 I became fascinated by vampires, Barnabas Collins in particular. I would raid my grandmothers closet, dress up and pretend to be a “damsel in distress”.

      Jillian

    • #259763
      Caty Ryan
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      I dont think I was more than 10 and there was a trunk full of women’s clothes in our garage. I used to love to try on the dresses and then graduated in my early teens to “the full bit” of my mothers bras, girdles and dresses. This was almost always in the winter, when I refused to go to the “family holiday cottage by the sea” for the weekend, cos there was “nothing to do”.

      That all came to an abrupt halt one night when some relatives came to check on me…My father being “the Aussie pub drinking male of the 60’s” told me that if I did not stop, “the boys in the pub would call me a queen”…

      Shock…. horror…. a fate worse than death….

      My mother also had a one piece swimsuit that seemed to reside full time in the laundry. So on warm days when “home alone” that would be donned with tennis balls for boobs. (They were’nt “arf scratchy on my chest….)

      It was also in these early days I read an encyclopedia entry on period women’s fashion. A fascination that still holds today… (See my CDH profile photos for proof!!)

      Also over 60 years later, I still reckon there was a “line up” for parts in school play where I just missed out getting a female part.  It still feels like I dreamt that, but I can see the location clearly in my mind to this day.Not to mention the old Australian “upscale private schools” of the 60’s casting boys in female roles in the school production.

      To this day any male playing “Lady Bracknell” in Wilde’s “The Importance of Being Earnest”, (that’s you Geoffrey Rush), has me green with envy.

      Which brings me to these folks costumes. Do they just sew some padding into the “boob” bits of the dress or if not that the bra, or do we go “for realism” with breast forms??

      Another topic, another time??

       

      Happy dressing

       

      Caty

       

       

       

    • #259756
      DeLora
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      My first inkling was I grade 1, I was fascinated by how the girls had their hair done and wondered what it would be like to have my hair like that. Soon after that I started to notice the clothes. It was a few years later that I found a pair of blue wool tights in a bag of kids socks we had been given. I have been seeking clothes and opportunities since that day over 30 years ago.

    • #259728
      Lily 96
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      I always wondered what it felt like to wear women’s clothes. So one day when I was home alone I got a pair of tights and a skirt and put them on and they felt so good. I spent all day in them as I had the house to myself for a few days.

    • #259714
      Dana
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      I was in kindergarten. There was a playhouse for the girls. There were pull over dresses that the girls would wear for tea time. I loved wearing them as well. I played dress up until I was told to get out and play with the boys. So sad😢

       

      Dana

      • #259748
        Bobbi
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        I’m so sorry that happened. Really, what harm would it have done to let you play with your girlfriends?? That upsets me so much when I see people trying to force others to follow like sheep!

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    • #259703
      Bobbi
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      I was about 5 years old, & it just felt right! I was wearing my grandmother’s things, & she caught me, & asked me if I liked wearing them. I told her “Yes, because it makes me feel right”. The next day, she bought me the prettiest dress I’d ever seen!
      After that, she was always buying me pretty things. She took me out shopping & to lunch with her friends & introduced me as her granddaughter. She made me feel so special.
      My mother gave me one of my sister’s old Catholic school uniforms.
      (I wasn’t allowed to go to school in it, but she let me do my homework in it).
      After 3rd grade, we moved away & I attended public school. My wardrobe got “softer & softer”, as the years went by. finally, in my second year of High School, I just went stopped wearing boy clothes altogether, because I was growing boobs & couldn’t hide them anymore.
      Oh dear, you asked for my earliest memory, & I’ve given you my life story! Sorry! LOL

    • #259696
      Peggy Sue Williams
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      Registered On: June 26, 2019
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      Stephanie,

      IMHO, I think many boys confirm their desire to cross dress, while participating in a cub scout play, costume party, show & tell event, etc.  I jumped at every chance to play a girl part, and I do recall many other boys doing the same thing.  The mothers would do our make up and pick out pretty outfits for us to wear.

       

      Peggy Sue

      3 users thanked author for this post.
    • #259638
      Autumn Valiant
      Participant
      Registered On: July 14, 2019
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      Hi Peggy Sue !

      My Aunt came to live with us for a while when I was very young. Maybe 4-6 years old. She shared my bedroom and we shared a dresser. I remember her being out (most likely dating the man who became my uncle) and I went through her things in the dresser. I was fascinated by silky underthings and recall wearing what must have been a half slip as a dress. She never said anything to me and probably not to my parents either.

      Hugs
      Autumn

    • #259576
      Boots Deville
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      Registered On: November 20, 2018
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      I would sneak stuff out of my younger sisters hampers and drawers. I was probably about 12, late developer, small and skinny. This would have beem late 70s, so pastel colored nylon panties, mid length skirts and fuzzy sweaters & leg warmers… I loved the feeling… later her prom dresses, satin lined and felt like heaven

    • #259565
      Stephanie Kennedy
      Participant
      Registered On: March 15, 2019
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      I have two early memories .I loved wearing my sister’s nite gowns to bed .It always felt comfortable. One early morning my mother woke me and told me to get out of that nity before my father got up and saw me. She asked me what I was thinking .She told me only sissy boys wore girls clothes. That was a defining moment in my life. That was the beginning of a life time of anxiety trying to understand who I am. and why I enjoyed dressing as a girl. I was about six or seven. The second time was wonderful . I went to a costume party for cub Scouts dressed as Goldie locks. I won first prize.I was in heaven. I walked all the way home in my cute costume. The woman that lived next door saw me and  said I looked like a cute girl in that outfit.. Thank you for the question I enjoyed the memories luv Stephanie

    • #259559
      Emily Alt
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      Registered On: August 24, 2019
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      I remember shopping with my mother and aunt when I was 4 years old. My aunt caught me trying to put on a bra in the dressing room. She took it away and gave me a stern warning. AFAIK she didn’t tell my mother.

    • #259528
      Amy Myers
      Participant
      Registered On: February 11, 2019
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      The first time that I remember dressing up, and also this is a bit fuzzy too, when I was about 12 or 13 years old. I cannot remember why, but for some reason I took some of my Mom’s undies out of the laundry hamper and put them on. It was so thrilling to be wandering around the house in her underwear. I did this as often as I could, and I honestly can’t remember how often that was either! At this point we lived in a small house, and didn’t have privacy unless everyone was out, but at this point in my life I was old enough to be left at home alone, and I was an only child.

      It was always underwear, I never used cosmetics, or put on her outer clothes.

      This went on for some time, till we moved, and didn’t have the privacy anymore. Besides, by then I was just getting my driving license, and had discovered the wonderful world of teenage girls!

      Amy

    • #259472
      Jenny Thigh High
      Participant
      Registered On: August 10, 2019
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      Around 12 or 13, I would stay home “sick” from school so I could have the house alone.  I put on my sister’s pantyhose and would read her Cosmo mags.  I loved the feel (duh!!) and loved reading Cosmo tips  intended for women at the same time.

      I don’t really remember what drew me to them in the first place, but even then I was having gay feelings and it seemed like a natural progression of what I was feeling, even if I didn’t fully understand them.  I made me happy and comfortable to just be more like a girl.

       

    • #259455
      ChloeC
      Participant
      Registered On: November 5, 2019
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      I’m thinking it was probably age 5, I asked my mother if I could wear a dress.  She made one out of kraft paper and I remember her making it in the living room, and then wearing it outside in our side yard on a warm summer day.  My next full memory is probably age 8 or 9 and I was into full damsel in distress mode imagining my ‘knight in shining armor coming to rescue me’. In this case I was Maid Marion and it was Robin Hood.  And I was far more discreet in letting sharing my feelings with anyone which now included my mother.  From there is was sneaking in and trying on some her lingerie, a party dress, etc.etc.etc.

    • #259450
      Anonymous
      Inactive
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      For me, the urge to express myself as a woman came very late in life at 64. I suspect that there are older memories that I suppressed. Looking back at pictures of me as a preteen boy, I would have looked very much like a girl with longer hair.

    • #259449
      Anonymous
      Inactive
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      that’s an easy one for me girls I remember it like it was yesterday I was five years old and I went into the bathroom and I saw a pair of my mom’s panty hose laying on the counter and I pick them up and looked at him and I always wanted to put on a pair of them watching my mom get ready for work all the time and pantyhose high heels dresses etc so I picked them up and slid them on and I just looked at myself in the mirror and I love the way they look till my legs the way they felt and I sat on the edge of the tub and cross my legs just as dainty as I could and I just sat there for about a half-hour just in a crossdressers euphoria I guess you could say after that any time I was alone when I was a youngster I was wearing pantyhose and to this day I still love wearing pantyhose even under my jeggings or pair of leggings I’ve always got on a pair of sheer pantyhose alright just another little tail from me thank you ladies Jasmine kiss kiss 💋💋

    • #259444
      Gigi Mathews
      Participant
      Registered On: July 16, 2019
      Topics: 9
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      My earliest memory was wearing lipstick at age 12 or 13. I could have easily passed for female when I was younger and was sometimes mistaken for a girl Peggy Sue.

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