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Thread: Childhood Crossdressing memories??

  1. #26
    Member Tonya Rose's Avatar
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    For the first time ........ I have to agree with Lorileigh ! Here! She nailed it!!!!!!
    Tonya Rose This is me! (song by camp rock)

  2. #27
    Chick for a Day Tricia Lee's Avatar
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    There exists photographic evidence of me, somewhere between the age of 2 and 3, simultaneously wearing a pajama top, holding a toy rifle, while standing in my mom's red slingbacks with a 3" heel. I need to find that picture.

    I don't remember that specific event, but some of my earliest memories are trying on shoes in my mother's and aunt's closets. This was all well before the age of 5.

  3. #28
    New Member michellechong's Avatar
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    I vividly recalled my first time wearing a red panties picked up from the ground just outside my classmates's flat, the moment I slipped the lingerie on, I had an instant "release" and this kick-start my journey into crossdressing and beyond. From just panties, I progress to bras, panty hose, dresses, make-up, heels,....Initially I wore my elder sisters" lingerie and clothing, eventually I stole from the cloth-line in my neighbourhood. This went on for a few years till I was finally caught by a man who trailed me into a forested area, waited for me to dress up, before approaching me. This lead-up my progression beyond just crossdressing.

  4. #29
    I am me! TrishaTX's Avatar
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    I see your point, usually what we remember is what is reenforced by someone or something over time if it is before the age of 5. I remember very little to be honest before that age. I remember after of course, especially my mothers's night gowns...and that is still my favorite thing to wear.
    No regrets except I should have got dressed & stepped out sooner.

  5. #30
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    Jewelry...that is my earliest memory! I was an oops baby, parents and only sibling were MUCH older and my brother would take me around in his car while visiting his girlfriends (i must had been 5, he bought a car-so he was 17). One of the prettiest , I remember her well, she wore ankle bracelets, lotsa rings, so after a few times visiting her, I wanted to be like her and crafted my own jewelry. Mom saw me wearing it and I think that was stopped by her as she knew dad would have exploded! But within a couple of years things progressed to under garments...naturally! Whether mom knew or not, I don't know-she never said anything.

  6. #31
    Aspiring Member ShelbyDawn's Avatar
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    I have verified memories through other family members of things that happened when I was three or four.

    My earliest crossdressing memories are about five; I would steal my moms slips and panties from the oldest of my three sisters who was a year younger than me.
    Quit wearing my mom's slips in grade school but continued to "borrow" my sisters panties into high school when my mom started buying me men's bikini briefs.
    I don't remember ever asking her to buy them and she continued to buy my brothers tighty-whiteys so I think she knew about my little habit...

    And I will admit that my sisters panties continued to get 'accidentally' mixed in with my briefs until I left for college.
    I am Me and Me is OK!



    Shelby

  7. #32
    Neanderthal in nylons Julie Denier's Avatar
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    I remember clomping around in my mom's heels as a toddler. Later I experimented with pantyhose and other clothing. Once, as a grade schooler, I played dress-up with my younger sister; Mom came by to check on us and I tried to change quickly. I think she saw me partly dressed up but never mentioned anything about it. After that, I made occasional forays into my mom's closet. For a while, her shoes fit (size 11) but I outgrew them quickly ...

  8. #33
    Platinum Member Eryn's Avatar
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    I remember a few things from that age. I remember finding that it was great fun to draw on the side of a bookcase with a pencil and pen until an adult happened by. I also remember being at a community dance at age 4 and making the mistake of asking another boy to dance because I didn't understand gender roles. I clearly remember the lesson I was taught by their ridicule.

    As far as dressing, I did some experimenting with Mom's hose and lipstick, but was always very careful not to get caught. By that point I knew that what I was doing was wrong in the eyes of everyone but me.

    I had no sense of being a girl. I knew I was a boy and that was incontrovertible by the standards I had been taught. It was much later in life that I finally figured out that I could be me regardless of birth gender.

  9. #34
    Member Cara Lacey's Avatar
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    36-2-29 That was my locker combination in grade school.
    Some people have better memories than others.

    My very first memory was getting caught at my Mother's dressing table, with bobby pins in my hair lipstick on my face . This is very early on in my life. I could not understand why everyone was so upset because I saw my mother do this.

    My second memory is my dad's 49 Studebaker catching on fire. I would have to have been about 3 1/2 years old when this happened, because my dad bought a brand-new 58 Ford in September of 1957.

    When I was about five, I remember getting caught in the basement with the kid across the street, trying on my sisters dresses.

    And from the time I started second grade up to high school, I wore my sisters panties to school on Monday Wednesdays and Fridays, because those were the days I did not have gym.
    Last edited by Di; 02-29-2016 at 02:18 PM. Reason: Read the rules please
    Cara

  10. #35
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    I had an interest in female clothes and the desire to want to be a girl from early childhood. I had a deep interest in stockings and tights. My first crossdressing experience was unsuccessfully trying on my mothers stockings at the age of six. Four years later at the age of ten I was visiting my girl cousin who was four years older than me and I begged her to dress me up as a girl in one of her dresses and tights. She had just started to wear tights/pantyhose and I was extremely envious of her. I don't think she wanted to go down the road of giving me a pair of her tights to wear but she did dress me up in of her dresses and she and a friend put make up on me. As soon as I was dressed I adopted the persona of a girl and loved it. The most significant event came two years later when I at last tried on a pair of my mothers tights. I wasn't sure if any of her skirts or dresses would fit me so I just wore the tights whilst wearing a boys sleeveless jersey. It felt so right I could not believe how girly my legs looked. The following day in school I could think about was my first time in tights. It turned out to be the first of many times. Thereafter I wore my mothers tights whenever my parents were out. Still not confident in trying on skirts and dresses I wore the tights with my football shorts to try and emulate the look of a girl wearing hot pants which were in fashion in 1972. A few months later I experimented with my mothers skirts and found to my delight that they fitted me. When I got to the age of 20 I further progressed to my mum's dresses, the feeling was awesome. When I got to 21 I began to pluck up the courage to buy my own hosiery, which opened up a whole new world for me as the style of tights that I bought was more appropriate to my age group. I loved black tights and also white tights and coloured hosiery was also very much in vogue in 1981.

  11. #36
    Junior Member Jessie29's Avatar
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    When I was really young (3 or 4) I wore my mums heels and fell into a table. Got a scar from it - an ever lasting memory of who I am

  12. #37
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    Having no sisters or close female relatives, the only clothes available to me were my mother's. I was in my early teens before I tried anything on and, by then, my height and weight were not too different from hers. What surprises me is the experience of many contributors who wore their mother's things when as young as three or four. For me it would have been impossible: everything would have been very much too big and wearing her clothes in any meaningful way would have been impossible. Her stockings, for example, would have been longer than I was tall at four years old!

  13. #38
    Junior Member Nine's Avatar
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    Before being 6, Ive received an electric train for Christmas. That was what I wanted and so happy to play with.
    My mother was happy to see me not playing anymore with the dolls of my sister. Happy to have a little dude.
    Some months after I went to the doctor with her. He told me I was not a girl and I had to stop to wear the dresses and skirts of my sister.
    I didn't touch anymore this train after that, but I still get it and I am still what I am.
    I don't have so much memories just I liked to wear dress and skirt. That's what I remember of, not really pleasure.

  14. #39
    Senior Member Jennifer in CO's Avatar
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    photographs help with memories quite a bit...jogging the brain as it goes. My earliest "memory" is a photo of me in a shorts set/romper that was my older Sisters (primrose yellow and very girly). No memory of that event...I was maybe 2 or 3. Do remember even without the movies several Christmas mornings and one particular where my Sister and I come out of the hallway wearing similar flannel gowns. Two seconds later the camera stops and next frame I'm wearing a long blue robe that covered the gown...except the lower 3 inches of ruffle...Several other times I remember being dressed in my Sisters clothes. Don't remember why, but starting at 10 when I went to my Cousins for 3 weeks and spent all of it in her clothes I remember that like it was yesterday. Course, I was writing a diary by then as well so it was easy to remember. When you write something down, it usually becomes ingrained in the mind...the good and the bad...

  15. #40
    Full Geek Status Adriana Moretti's Avatar
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    When I was a kid my one of my favorite places to play was my grandmothers walk in closet in the basement ( it was really its own room) it was loaded with my mothers, and my 2 aunts old clothing, and on the top shelf had a colection of all their wigs from beauty school....I played in this room for hours trying on dresses and bad polyester pant suits LOL....and besides that room..my grandmothers bathroom had about a 10 foot makeupcounter and mirror....i would lock myself in the bathroom and play with the makeup too ! xoxo

  16. #41
    Style Icon Sara Jessica's Avatar
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    What I am able to recall in my mind's eye from before age 5 is like snapshots and there are certainly a handful that relate to dressing up to some extent, whether mom's clothes or my friends (playing house, I was somehow always the little girl). Yet at the same time, the feeling of being transgender was pervasive in my earliest memories, much more so than acting upon those feelings by dressing up.
    Like a corpse deep in the earth I'm so alone, restless thoughts torment my soul, as fears they lay confirmed, but my life has always been this way - Virginia Astley, "Some Small Hope" (1986)
    Sunlight falls, my wings open wide. There's a beauty here I cannot deny - David Sylvian, "Orpheus" (1987)

  17. #42
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    My first memory is at age 4. My cousin who is only 10 months older than I, was having nail polish applied by her mother. I said that I wanted some too. My aunt looked at me and said sorry, we don't have any blue nail polish. I replied "but I want pink, like Jo Jo". I was told very sternly that boys do not wear nail polish. That was the beginning of the shame game for me, and the beginning of compartmentalizing and burying this part of my personality.
    Last edited by Lorileah; 03-02-2016 at 05:39 PM. Reason: no need to quote OP

  18. #43
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    I remember checking out my Mom's lingerie drawer when my parents went out on Wednesday night to play cards. I would put on her bra nd stuff it with socks or tennis balls and prance around the house! She noticed that her things had not been replaced in her drawer properly and one night, I found a new Playtex bra in my size under my pillow with a not that said, Now you have your own, please leave mine alone! Nothing else was ever said, but I still wore that bra until graduating from High School!

  19. #44
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    My earliest memory was watching my older sister at her dancing classes and asking her to dress me up in her yellow dancing tutu which she did - this would have been shortly before my fourth birthday. I remember feeling really pretty as a ballerina and asking my Mother if I could go to dancing classes like my sister. Unfortunately it was "for girls only"!

  20. #45
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    I found a corset belonging to an aunt who lived with us, when I was about 10 it was far to big but it felt good, later I found some nylons the rest is history, the same aunt would polish my nails with a pad thingy and tell me my hands were wasted on a boy

  21. #46
    Member Kiersten's Avatar
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    I was 6 or 7 when i had My first significant memory I recall. If there were any other signs earlier then that I can't recall.

  22. #47
    Member Sister Rachel's Avatar
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    I remember very clearly. I must have been three or possibly just turned four. I looked in a bedroom drawer and found a pair of my gran's knickers, green lace-trimmed (in some kind of artificial silk ?), immediately put them on, felt wonderful, so wonderful I started bouncing up and down on my grandparents' bed gleefully, was discovered by my granny. Definitely NOT wishful thinking, it's one of my clearest early memories.
    It's complicated, then again it's simple ... where did I put that skirt?

  23. #48
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    At about 3yo (1946) my Mum put curlers in my hair. Hated it. She was preggers with what turned out to be my first sister
    She tried to explain that my girl cousins had to do this but I was not impressed. She had made some curtains and had used a few offcuts to make a little dress. I didn't want to try that on either.
    She may of suspected that she was going to have a baby girl and was awash with fem hormones.
    Now.... if only she was here to do it again and I still had the hair to do it with.

    During primary years at an all boys school some of us smaller "pretty" boys had to dress up as girls for an annual concert and
    dance with the more macho taller lads. I remember that my partner had roughish hands. I don't know why he had rough hands. In later years he became a lawyer or accountant or engaged in similar villiany . Definitely a profession for soft hands.
    I was decked out in a mid calf length blue ball dress with a red cherry broach attached. In my memory......... very pretty. Sigh.
    The women charged with our make up didn't seem to notice that we were all wearing our black boy shoes and long dark school socks.
    When we went onstage we wondered why the audience was laughing. It was not supposed to be a particularly funny role. Or so we thought . We had practised the waltz routine for weeks to get it right.
    They, of course, were at eye level with the footwear and our chunky boy legs. Very droll minister.
    The gender change role did not, at the time, seem to be significant but when I collided with puberty a few years later I started "borrowing" items of female apparel.
    Was that the result of the seeds sown back in 46 and 53 and the other chinks in my masculine charade ?

  24. #49
    Junior Member LookingGlass's Avatar
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    I remember when I was young, about 7 or 8, my favorite shorts were these red ones I later found out were actually girls' shorts. We briefly moved into my grandparents' house when we moved to the same town. Lo and behold she had a dresser in the room I used that was full of young girls clothing she saved from when my mom and aunt were kids (the one time her hoarding habits paid off). Bras, pantyhose, stockings, all kinds that were still in good shape from what I could tell... fun nights sleeping in them underneath my PJs!

  25. #50
    Member Petra1's Avatar
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    I didn't start til I was about 12 years old. And it had more to do with my fascination for breasts and wanting to experience different things while wearing them. It started with borrowing my mom's bra and stuffing with washcloths and wearing them under my regular clothes. At that age, there was definitely some sexual excitement from dressing.

    Before starting high school, I spent the summer visiting my favorite aunt. While she was working, I was home alone. That was some fun to be had.

    In my freshman year, I stopped going on the family weekend camping trips because I wanted to stay home and spend the weekend dressed.

    In the beginning of my sophomore year, I joined an organization that had a spirit week as part of its initiation. One of those days, all initiates had to dress in drag. When I asked my mom for a bra, she told me she didn't have one that fit me. I had to keep my mouth shut so as not to disclose that I had already been wearing her bras so I ended up having lopsided boobs all day.

    That was the same year mom got divorced from her second husband. We moved. Mom ended up working nights. After the siblings went to bed, I would throw on a bra and and stuff wth towels (instead of washcloths because I wanted bigger boobs) under my regular clothes and go bike riding in the dark, around 10pm. One night I went about a mile and a half one-way.

    I don't remember if it was that year or the next that I first dressed publicly for Halloween. Mom had an old sleeveless mini-dress, that I stuffed with towels, and a pair of pantyhose. I remember her telling me the boobs were too big so I used washcloths, until she left. Then I went back to the towels. I also took off my underwear and wore only the hose ( the dress was long enough to cover up the boys). Stayed home and passed out candy. Got compliments from a few women. One even said I was the cutest one she had seen. Later took my little brother trick or treating while I was dressed.

    Actually, the only times I ever dressed publicly, and actually allowed people to see me dressed, were for Halloween. The second time was in college. The third time was about 9 years ago, again, staying home to pass out candy. The wife wasn't too keen on me leaving the house and didn't like it when a group of kids came back a second time to ask questions because the first time they thought I was really a woman, albeit an ugly one, until I spoke.

    My wife has seen me dressed several times but I've since backed off dressing in front of her. When we were dating, she thought it was exciting to see me dressed but I think my wish to sometimes be more realistic has turned her off the idea. Once in a while, I'll trot out a new outfit to model but for the most part, I try to be the man. She says she doesn't mind but I'm not sure.

    And now that she's not working weekends anymore, my time is limited. Pretty much only when I stay home while she's working.

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