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Thread: How did you crossdress when you were 4 or 5?

  1. #26
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    I'd like to run AI on this thread to get a summary, but I don't know how to.

    But there are some interesting insights.

    Many of us (not me) played dress up with local girls our same age.

    Many of us (not me) were either let alone at a young age or were (not me) able to rummage around in mom's or sis's clothes while they were still around the house.

    Many of us (not me) started with slips.

    And from the other thread, many of us (not me) were force femmed by being a model for mom's seamstress side business or were actively force femmed by their mom who really wanted a girl. Where was dad when this was happening? I think some of these might be considered sexual abuse of a child today, if the authorities found out about them.

  2. #27
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    I was about 4 or 5, there was this velvet dress that I was just drawn to hung in my sisters room, I remember thinking I have to try this on, but, even at that age I knew this was "wrong", so I waited until the coast was clear and tried it on, it fit perfectly, then I heard someone coming, it was my older sister, so I hid in the wardrobe, unfortunately after awhile I knocked, over some shoes, she heard me and said whoever is in there come out ,(looking back now, I think she was actually afraid), I reluctantly came out, she burst out laughing and ran to get my mum and other sister, I took my chance and crawled in under the bed while also trying to take off the dress, at this stage my sister had returned with my mum and other sister. They tried to encourage me to come out from under the bed while also playfully teasing me, but, at this stage I was so embarrassed I just couldn't face them. I eventually came out and I remember one of my sisters trying to cheer me up as I had been crying. I can't really remember much else, but, I don't ever remember it being mentioned again. Thankfully my dad and brothers weren't home at the time, don't think they were ever told.

    It was the first and last time I got caught, but, apart from putting on heels, clip on earrings and putting lipstick on whenever I got the chance I didn't dress up again until I was around 12 or 13.To this day I still can't explain the urge to wear that dress, it was just irresistible to me.

  3. #28
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    I was not that young. Don't really remember when it started - maybe mid to late elementary school. It started with my mom's panty drawer and eventually into her closet when I was home alone on occasion. I also have a aunt that is only like 6 yrs older than me and when at my grandparents house I would get into her drawers and closet. When I was in middle school to early high school when she went to college she left a lot of clothes at home so I also took advantage of that.

    I always wished I had a sister that could and would dress me all pretty - but I only had a brother.

    When in high school I started buying my own panties and one time my mom found them. She made some pretty snarky comments once but nothing after that time. Really haven't done much with it since college until recently again.

  4. #29
    Silver Member CynthiaD's Avatar
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    I started at age 3 with red nail polish. Mostly panties and slips through grade school. I added bras and dresses in high school.

    I was in fifth grade when I realized that most boys didn’t want to sneak into their mothers’ closets and try on their clothes.
    What do I do on days when I don't crossdress? I have no idea.

  5. #30
    AKA Lexi sometimes_miss's Avatar
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    I was likely about 4 when I first did it on my own; mom always spent lots of attention on my older sister, getting her ready for school. So, one day, feeling ignored, I went to my sister's room, took one of her dresses, put it on, and went to my mom and said, 'I'm ready to go to school, too!'.
    Of course, mom wasn't having it, took me back to my room and changed me back to my boy outfit. We later walked my sister to school as usual. When we came home, she asked me if I really wanted to wear the dress, but said it in such a way as to imply that my answer should be no, so that's what I said. But I still envied my older sister. It would be a few more years before the onset of events which would trigger my lifetime of crossdressing and feelings of expecting to eventually becoming a girl.
    Some causes of crossdressing you've probably never even considered: My TG biography at:http://www.crossdressers.com/forums/...=1#post1490560
    There's an addendum at post # 82 on that thread, too. It's about a ten minute read.
    Why don't we understand our desire to dress, behave and feel like a girl? Because from childhood, boys are told that the worst possible thing we can be, is a sissy. This feeling is so ingrained into our psyche, that we will suppress any thoughts that connect us to being or wanting to be feminine, even to the point of creating separate personalities to assign those female feelings into.

  6. #31
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    My first memory of trying on feminine undergarments was maybe at age 6 or 7. It was our neighbors brassiere. I don?t know the size but she was well endowed.

  7. #32
    Trans woman BiancaEstrella's Avatar
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    I had a cousin my same age whose shoes were 1 size smaller than mine, and I was heartbroken over it. I wore my grandmother's too-big-for-me shoes around.

    At age 8 there was an aunt whose shoes I fit perfectly and I loved "organizing" her shoe closet (trying them all on).
    "Be yourself; everyone else is already taken."
    Oscar Wilde

  8. #33
    Member JesseVF's Avatar
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    For me (I think at age 5) it was the open bottom girdles my mother and much older sisters wore. Then quickly bras stuffed with something soft - with a slip even better. No interest in actual fem clothes until around age 60.

  9. #34
    Member KrissyTN's Avatar
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    I started when I was closer to 7 ... we had a clothes hamper in the bathroom and my Mom would fold up her bra and leave it on the stack of towel (or in the hamper). I remember looking at it one day and I wondered what it would be like to try it on. After that, I always looked for the opportunity to try on bras, panties and pantyhose whenever the opportunity arose.

  10. #35
    woman on the inside Ashlee's Avatar
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    I remember visiting my relatives in Alabama and rooming with my female cousin, we were 7 and I was always wanting to and was wearing her pantyhose and my uncle removing them. Pantyhose remain my favorite item to wear when I dress, Wolfords are absolutely amazing in how they feel on legs. I'll buy some for my makeover trip in Dec. to wear.

  11. #36
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    Quote Originally Posted by Sometimes Steffi View Post
    or were actively force femmed by their mom who really wanted a girl. Where was dad when this was happening? I think some of these might be considered sexual abuse of a child today, if the authorities found out about them.
    100% it is and its sad and sick.

    It was /is abuse then too ... I hate to say it but a lot of these women are definitely predators that would do something like this. We've had others here tell us the same story ..
    These women normalize their behavior and teach the victims to keep it quiet . So dad doesn't even know ..The victim doesn't see its abuse but instead thinks that it is love . It definitely is not. It messes men up for life .

    Both my fiance that died and my ex-spouse had dressed were victims of women like this also.
    My fiance's mother was angry that his dad/her husband committed suicide and therefore left them. She made sure to drill it into my fiance's head that all men sucked horribly and shouldn't even be on Earth/allowed to live and that women were the be all end all of the entire universe.. she did that from the time his dad died when he was 9.

    My ex spouse was dressed and paraded around in secret by a grandmother when his parents would drop him off there to go out on the weekends . He refuses to tell me which grandmother as well .. she would get him all dolled up started at about age 5-6 and made sure he knew not to tell his parents .

    Fast forward 20 years plus or minus and they become my clients and they want to live out these sick fantasies. I get up to 20 of these people a day sometimes so it's there it is happening..

    I have had some pretty tense conversations with plain feminists and terfs alike about this .. they do not like to admit/or hear about it, that this happens, but it does .
    Last edited by Dutchess; 09-30-2024 at 02:51 PM.
    IG : Knightress Oxide

  12. #37
    Aspiring Member HollyGreene's Avatar
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    At the age of about 3 or 4, all the kids in the street were boys. Then a family with a girl moved in nearby. I'd never really seen a girl and I was enthralled. I loved the long hair and the pretty dresses. And yearned to look like that.
    At age 6 I found a bag of my mother's now unused clothes, and there was a chiffon nightdress that I tried on. I liked it so much I kept it and hid it under my bed and used to sleep in it, quickly changing into pyjamas in the morning.
    By that time, I had a younger sister. As soon as she had grown big enough that I could squeeze into some of her clothes, I was hooked.

  13. #38
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    I got dressed up by a sister when I was quite young(<6). Been at it ever since.

    The interesting part is i have no memory of when I was told it was "Bad/Shameful" and subsequently hid it. (We all know it was different back in the day)

  14. #39
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    I have memories from when I was about 7 or 8 years old watching tv with my mother and I remember it was around back to school time and they were running advertisements for back to school shopping. One of the ads was a JCPenny ad for girls clothing, I looked at my mother and asked if I could get those clothes this year, she said ?no those are for girls?. Little 7 or 8 year old me was disappointed and I felt a little deflated cause at the time this was 97ish and the girls clothes looked better compared to the boys so I didn?t think it would be that much of a difference and I also liked the way they looked. I also asked again at Christmas time that year, when they were advertising winter clothes and was shut down again. After that I felt defeated and didn?t want to try again. Flash forward a year to the summer of 98. A new family had moved in across the street and we became friends. They had 2 daughters around my age, 1 was older by about 2 years and the other daughter was 2 years younger than me. So I was the middle child with them. We all went to the same schools so we all went back to school shopping together to make it easier for all of us. There were times when I had to wait to shop for my own clothes cause we always stuck together. Well while waiting I remember I saw a nice skirt and shirt that I liked and I mustered up the courage to try what I tried last year again. I grabbed the 2 items and asked my mother if I could try them on and get them. Everyone laughed jokingly and my mother was slightly mad and embarrassed at the same time, but little 8 year old me wanted them. My mother then explained 8 year old boys aren?t allowed to dress in 8 year old girls clothing. So once again I was defeated. I gave up and pushed down my feelings and desire for those clothes. I guess the pink fog left me for a bit. When I was about 12 years old I remember being home alone and watching tv. I was watching a show called ?Totally Spies? as I was watching there was a scene then felt similar to my back to school shopping experience with one of the main characters not being able to get the skirt and top she wanted. After watching that scene the pink fog came back and hit me hard. I went to my mothers room and found one of her skirts and tops, I found a pair of panties and a bra and tried them on and I could feel little 8 year old me finally being able to wear the skirt and top that he wanted to wear.

  15. #40
    Member Richelle423's Avatar
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    I remember being 5 or 6 years old and walking around the house with a towel wrapped around my waist with a clothes pin to hold it wearing it like a skirt.

  16. #41
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    We are all different! I didn't have a sister and didn't have any interest in wearing female clothes until I entered my teens - by which time some of my mother's things fitted reasonably well. Had i tried wearing those hings when much younger, they would have fallen straight down to the floor!

  17. #42
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    I was about four, and it was the days when women wore furs, and girdles, and wigs.

    Like it was yesterday, I vividly recall looking out the window, my family was in the front yard. My Mother's fur stole was on a chair. It was left there from when she had come home the night before. It smelled like perfume and cigarette smoke. I was overcome by a strong desire to wrap it around my shoulders, and I did...I remember its lining felt cool, as it sat on my skin. My next dressing memory was reaching into my Mother's dresser, [How was I alone at that age? Was I? I don't remember] and trying on a pair of her bras and panties...I recall placing her fake pearls around my neck, and liking the look so much, I then ran to her closet where I tried on one of her many frosted blonde wigs. Young as I was, I was driven to wear her lipstick. I picked a shiny golden tube of coral pink, a popular color back in the day, I remember my hand shaking as I nervously traced my lips as neatly as I could. I walked around the upstairs of our home. Staring at myself in every mirror we owned. I loved what I looked like...And, to be honest, today, when I dress and give that final shake of my wig, I still see that same young woman looking back at me today.

  18. #43
    Junior Member Myra Thomas's Avatar
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    I cannot remember how old i was when i started, but it was with my mother’s help, and in full with my older sister’s underwear and velvet dresses and shoes. My recollection is that i would dress regularly when my father was not around!, and it felt so natural. When a little older at around 10, i wpuld underdress in my mother’s corset and stockings and on occassions her swimsuit, oh such bliss. The earliest photo i have of me dressed is at the Queen’s coronation fancy dress party, pushing a doll in a pram! Those were the days.

  19. #44
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    It was my mother's hosiery for me.

    I remember sneaking into her drawers and trying on her stockings and pantyhose before trying on her lingerie and a dress.

    I must have been about 10 when this started.

    I don't remember doing anything at an earlier age although my mother would gaily recount the time I came down wearing her lipstick and walking like I was in heels. I don't remember any of that.

  20. #45
    Silver Member Maria 60's Avatar
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    I don't remember my age but it started with my sisters pantyhose and then her and my mothers slips. For some reason I felt like the bra and panties were a very personal item and never wore my sisters or motherss. The first time I wore a bra or panties was when my wife bought me a pair when I told her about my habit. For me it was mostly pantyhose and the occasional wearing a slip.

  21. #46
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    Mom had a "rag bag" upstairs in my closet and I found an old pair of her panties in it. I tried them on when I was probably about 8 or 9 and I was hooked. I almost wonder if maybe she wanted me to find them. I almost bet she knew I was wearing some of her items. Memories!!!

  22. #47
    Silver Member Pumped's Avatar
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    It wasn't unusual for my mom to run over to the neighbor's for a while. I figured out that meant an hour or so alone. I would grab one of mom's bras from her dirty clothes and stuff it with socks or what ever I could find. I remember using a towel as a skirt.

  23. #48
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    Interesting responses.

    As the OP, the reason I asked is that nothing that I could have borrowed from my mom would have come close to fitting me when I was 5. Not that my mom was big, but that I was 5.

    Furthermore, I have very few actual collections of anything that happened to me before I was 5, except some really traumatic events like my emergency appendectomy. I guess you girls have better memories than me,

  24. #49
    Mannequiniste ! Stacy Darling's Avatar
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    What happened back then?
    I was a boy? in a military suburb surrounded by women and mainly girls.
    All the men were =, out.
    So I played with the girls, dressed up and didn't tell about Mummies hoping in the bath with me.

    Guess I was content at the time and quite happy in a frock,
    still am.

  25. #50
    Member JustineFallow's Avatar
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    When I was a baby, the day I grabbed a pair of pantyhose and put it on was an occasion of great hilarity. My mom even took pictures! A seed was planted.

    Fast forward to four or five: It was a pretty dry period for CDing. I was never left alone at that age, so sneaking a pair of pantyhose was out of the question. Around that time Mom caught me trying on a pair she had left on the bathroom floor, and told me not to do that anymore because people would call me crazy. That was rather distressing to hear back then! But the urge never went away, so I'm sure I tried again once or twice.

    It wasn't until I became a latchkey kid that I knew I could indulge until one of my parents was due to come home. By that point, I was trying on *everything*: hose, panties, bras, dresses, and heels. (Never did makeup, though, because I was afraid I'd stain something or leave behind a trace after taking it off.)

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