How did you crossdress when you were 4 or 5?

around age 11 alone at home i open my mother's underwear drawer and within minutes had on her girdle and nylons, the next time i added her bra to the equation and
and stuffed it with other nylons. I think my mom suspected(runs in her nylons?) but never called me on it.
Soon after my mom brought home a dress for me to wear on Halloween and asked me if i wanted to try it on?
I refused( in hindsight a huge mistake?) After that somehow knowing i stopped raiding my moms underwear drawer.
Throughout puberty i always had the urges but repelled them so i could fit in with the boys.
But as we all know the urge/compulsion never goes away!

Like you I started about age 12 with pantyhose, bra, and a dress all from the Goodwill or thrift store. Been hooked ever since!

I wanted to ride my sister "big 2 wheeler girls bike" (instead of my trike), but didn't want anyone thinking I was a sissy, so I wore my sisters pink leotard, so anyone seeing me would think it's just a girl riding a girls bike - nothing to see here.
Unfortunately, instead of people on the empty country road some 150 meters away, my whole family saw me from 30 meters away :)
I would have been 4 and a half
After that, my family let me wear my sisters pyjamas if I wanted to and she wasn't wearing that pair.

Think I was 7. And it was basically moms nylons, high heels, long line girdle, padded bra and a frilly pink baby doll nightie. Probably looked horrid but felt amazing!

Wow, going back a long ways to be sure. Not exactly the first time dressing but at the age of five or six I can remember going Christmas shopping with my mom. We went to the department store in Scranton Pennsylvania. It was Chrismas and the store was so beautiful. Toys were on five at the Globe store, THE department store back then. On the second floor was the Women's Lounge. I thought it was so unfair that I could not go in to the lounge with Mom. The women back then dressed so beautifully! Not like today. They were dressed to the nines for sure, especially with the holidays coming. I like a bunch of other boys had to wait out front of the lounge. I remember how wonderful the women looked. I thought to myself that I wanted to join them. Maybe if I were dressed as a girl they would let me visit. The women, dressed elegantly in their finest sat in wonderfully comfortable chairs, Mom stopped in every time before heading up to the toy section. They sat and chatted, had a cigarette and made small talk. I was enthralled and thought that is what I want. I think it was after that I sort of thought I too could join them. I think I went into Mom's dresser and tried on stockings and a girdle so I too could feel like them.

I didn't start till I was about 9 or 10. And honestly starting that early made figuring out how to hide the bits after puberty harder. When I started I could put a tight swimsuit on and squish everything flat without much effort because it hadn't started growing yet. Which is generally what I did. Then I could put on a sisters dress or shorts and walk around feeling feminine. Truly didn't learn how to tuck till I was about 20. Before that and after puberty I just folded everything back. Which worked for when I looked down or in a mirror but made outfits fit odd let alone the discomfort when I sat down or tried to drive or ride a bike dressed under my public clothes. Once I learned the proper way to tuck things got a lot easier

My first experience at age 4 was on Halloween. We were going trick or treating. My mom said that I didn't have a costume so she had me wear my sister's coat.

By age 7 or 8 I found a pair of silky panties that fit perfectly. I wore them for a few days until my mom noticed what I was wearing. I also remember playing dress up at one of the neighbor's houses and trying on high heels.

Without getting into a very long story, my experience did start very young around the age of 4 or 5. I was an only child, and my mother had always wanted a girl. My dad had worked a lot of nights, so whenever he wasn't home she would dress me as her little girl and started calling me Joann. I am now into my mid 70's and well into my journey of who I was meant to be

Well, at 4 or 5 I didn't crossdress - we were so poor I was lucky to dress at all. However, that did not change that strange feeling I had that somehow I would prefer to be a girl. In part, even girls from poor families dressed much better and prettier than the boys. So in that sense, I felt that if I was a girl I wouldn't have to wear the almost rags I did. Yet there was much, much more to it than that. Remember, in 1949 and 1950 nobody had much as we were still coming out of the poverty that gripped the nation after WW II. But the feeling that somehow I was a lot like the girls in my mind obsessed me. Didn't know what to do about it - I didn't have a sister, but I sure wanted one. Still though, I behaved like an acceptable boy even though inside there was a great war brewing that would explode two or three years later. Definitely trans characteristics, but without any fine definition.

I was about 8 or 9 and my parents had dropped me off at my aunt?s house while they were taking a long weekend vacation. That afternoon, I spilled tomato soup all down the front of myself. All of my clothes were soaked with the red tomato soup, even my undies. My aunt said to go to the bathroom and take my clothes off, wash up, and get into a new pair of clothes. That?s when I realized my parents had driven away with my little duffel bag of clothes for the weekend.
To solve the problem, my aunt gave me one of her cotton nightgowns to wear while my clothes were being washed and dried. When I came out of the bathroom, my aunt started giggling when she realized I was going to need an additional piece of clothing. A bit later she handed me a pair of her panties to put on. They were so soft and satiny! And the feeling I got wearing them under the cotton gown was euphoric. Bam! That was it. I begged to wear them the rest of the weekend. I was infused with the desire to wear women?s clothes.

I don?t remember having any interest in crossdressing until puberty set in around 12 or 13. Then I started noticing girls and the changes in the shapes of their bodies and the clothes they wore. Especially interesting was their underwear. I spent quite a bit of time looking at the pretty lingerie in the Sears and JC Penny catalogs. Eventually, I just had to try some on a d here I am on this website years later.

Sister dressed me as her dressup doll.