Your earliest memories of cross dressing

[V M]

The earliest I can remember was at about 4 or 5... My mom dressed me in one of my sister's dresses in an attempt to embarrass me for "acting too girlie"

She became dismayed upon realizing that I was very happy about it and wanted to wear dresses everywhere everyday all the time and changed me back into my "boy clothes"

This of coarse would lead to me dressing in secret and afraid to "come out" for several years... Plus I would do rather dangerous things to "prove myself" a man

What is your earliest memory?

[Randi]

I think I am unusual in the respect that I can remember things from before I could walk-but my short term memory is not that good at times (go figure). Anyway, Mama would dress me in the cutest little outfits, sundresses, and shoes. Before I was born the doctors told my parents I would be a girl so everyone gave girls clothing for me to wear. They, not having much money to spend, used them so as not to have to buy any more clothes. The only time I had to wear male clothing (until I was 4 years old) was when we went out in public which wasn't often except for church once a week. I have always felt comfortable in feminine clothing and for the most part detest having to wear male clothes.
Randi

[A]

Uhm, I was about 4, I think. I had been searching the costume box and started to wear around the house that one black skirt I liked. Of course I was talked into stopping by my father and my sister, who, until then, had been actually crossdressing me for fun.

[azSam]

I think I was about 5, maybe 6. Tried on one of my mom's night gowns that was on the floor next to her bed. I was laying on her bed watching TV, then noticed it. Tried it on, it was waaaaaaaaaaay to big, then I got caught 

Fun times.

[Janet_Girl]

I must have been about five, when I found one of my Mom's bras in the laundry room.  I put it on and was prancing around when I heard her coming.  I ditched it real quick.

[ilanthefirst]

When I was a kid, my parents dressed me in neutral clothes and gave me a short haircut, because unisex sweats are cheap and I was too messy for them to take care of long hair.  I had a sense that I was a girl because girls sit to pee, and I was completely unaware of any other differences.  When I went to kindergarten that everyone thought I was a boy; after that, I wanted to grow my hair long (still not taking care of it), but I never went gaga over the color pink or experienced euphoria at the prospect of wearing a dress.  Heh, no wonder my mom wasn't surprised when I came out as genderqueer/transmasculine. . .

[Xakkun]

The earliest I can remember was one day when I was about 13 when a shirt of my sister's got mixed up in the laundry and I decided to wear it to school, under a jacket. I remember loving how the shirt fit me but I didn't really think too much about it.

The first time I wore a full outfit was shortly after my 15th birthday, where one of my best friends (a girl) gave me a pack of panties as a gag gift. I actually liked the gift a lot more than I thought I would, and although I didn't want most of the people there to know, I wore a pair that night. The next day at school, I talked with her about it, and she was quite understanding, and actually a bit happy that her gag gift wound up being more than that. The day after that, she brought me a shirt, skirt, and some stockings to take home, which I put on as soon as I got home and spent the rest of the day wearing, locked up in my room.

[Ashley Allison]

When I was around the age of 5,  I insisted on being dressed in a Belle (from beauty and the beast) dress.  My parents let me, and even put painted makeup over my face.  The family still tries to antagonize me by showing me the picture, and exclaiming how embarrassing it is.  It is more or less a running joke in my family, that from my point of view is out of breathe.  Little do they know, I am not embarrassed at all over it, rather proud for doing something I wanted to do.  It felt really good at the time; a sense of self-expression in my childhood I wasn't enabled to show off otherwise.  I guess that was the first time I officially "cross dressed", though I now realize it was more displaying my true colors    

[rejennyrated]

I suppose it depends on what you mean by cross dressing! LOL. Boy clothes were and always will be true cross dressing for me and oddly I get an strange kick out of occasionally wearing them even now, because I know I'm not a man.

There is something strangely magnificent about the cut of a really good suit... some snappy shoes and a well chosen tie. It's even better because I can't pass properly... 

To answer the question properly I started wearing female clothing from the age of about 4 or 5 and by the time I was at infant school was doing so openly and with my parents consent. My mother even put together a little dressing up box for me with various bits and pieces, and by the time I was 8 and at middle school I was even bending school uniform to a more gender flexible presentation by including a kilt rather than trousers.

[Muffin]

lols that gave me an idea..... to dig out my old suit and wear it around my parents house next time.. just for the lols. actually I might wait a while... actually that could be a bad idea.... ok scratch that >__<

uummmm I never realised how "normal" I am from reading this thread, pretty much the same as SamanthaFLA... I was five and my mum had left her nightgown in the bathroom... I locked the doors and put it on. I remember sitting on the edge of the bath with my head down and feeling sad. I was always so secretive I always locked the doors as we had kinda two bathrooms that connected, I had two older brothers that if they caught me I would of been pinned to the ground with my limbs pointing in every direction they shouldn't twice as much for twice as long :-/