Welcome to Crossdresser Heaven, a safe and welcoming place for everyone in the crossdresser community.
Join Crossdresser Heaven today to participate in the forums.
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.
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.
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 💋💋
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.
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.
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.
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
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.
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
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
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
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
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
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.
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.
