The first time I dressed as a girl was well before kindergarten. I would wear my cousins dresses and dance singlet since we were the same age. My mom and aunt thought it was cute and just silly. Publicly I have only gone out dressed in womens cloths a few times with the first being halloween at age 18.  Not until I really decided to transition at age 30 did I dress as a woman in public again.

Idk, when I was little. My dad would get mad, not that I hold it against him or anything.

This past august at age 51. Trying to figure out whether I might be MtF transgendered. A transwoman friend suggested I try going out and see how it felt. I didn't want to try unless I was at least partially passable, so I made kind of a engineering project out of it.

Before last summer the thought of crossdressing hadn't occurred to me. I didn't want to dress like a woman, I wanted to BE a woman.

I started dressing when I was 5 I remember it was around the time I started kindergarten.

I was probably about 17 - though I certainly would have done it at an earlier age if the clothing and opportunity were available.

I only went out publicly for the first time recently... talk about not making a discrete debut: the moment we stepped out of the Holiday Inn (we were in Dallas for a coupla nights to see a concert) I was asked for a cigarette by one fella while, simultaneously, a group of three young adults (or old teens) asked us if we knew of a store that might be within walking distance of the hotel.

What can you do? Just act normal - lol.

I'd say it went well.

Still haven't yet. Seriously.

I know.

at 10

Before I ever started school back in the '60's. 

The first time I went out in public that way was when I was 12.

The 1st time I put anything on me I was 6 or 7 and put on a girl friends babushka.
This was about 1949

My first time was on my birthday at 4 years old. It was a cute little polka dot pink dress. My Mom borrowed it and more little girls clothes from the family across the stream from us out on the rez. She wanted me to be happy on my birthday, instead of the sad child I was. Because of my body shape even as a child female clothes fit me better than male clothes did, so I wore female clothes whenever I could get away with it. Of course after my adoption I had to hide this from my adopted father, but he was easy to fool with this. I just kept my shorts and tanks in my locker at school, or outside somewhere where he couldn't find them. If it was just shorts and a tank most times he wouldn't notice. Getting away with little things like this is what kept me sane in that awful environment. Though when I got caught, I'd pay for it in blisters.

Allie

First time I dressed in female clothing was back in 1997 (if it weren't for going to see the Lost World: Jurassic Park 2 that weekend I wouldn't have remembered the year this happened, and that made me 23 I guess) when we got invited to a big family reunion, this in Massachusetts where most of the family came from, I didn't go, had to work, couldn't get the time off, so my mom, brother, sister and her only son (still a baby) at the time went. During my time alone at home, I had me a few days to reflect on the things I had been feeling about myself for many years that in recent years had become so strong that I didn't know what the hell was wrong with me, I did some experimenting and some dress-up. I tried on some of my mom's clothes, the ones that fit. There was this very nice dress that I thought I would look pretty in, if only I were a girl. I wore this dress almost the whole time, but taking care not to ruin it or make it so it looked like it had been worn., I also put on a little bit of make-up that I had the guts to actually go out and buy, pretty red lipstick. I was terrified when I went in to pick it out, stopping in at RiteAid on my way home from the mall after getting my ears pieced, and even more so when I brought it up to the counter to pay for it, I'm sure it showed too. Since I knew that I would be alone for several days (the whole weekend), sometimes I would spend all day dressed up in the house, occasionally I'd look at myself and dream, but for the most part I just did what I always did, sat around and watched movies or played video games, but dressed like a woman, I felt wonderful. But after it was all over with and I couldn't be me anymore because family was coming home, I got really depressed because I knew it was time to put myself, the real me, back into hiding (she was put away for a little while, but not long before I'd soon blow up and let it all out, but that's another story). Afterall, how could they accept me like this, I'd be a disgrace, an embarassment, my family would be angry, hurt, disappointed, ashamed, denial (this would be the first reaction), what else, so I went back into my shell.

You look lovely in your new Avatar Megan. And I know how you felt. Every chance I got while growing up I'd dress female letting the real me out. It felt so wonderful the feeling in itself is almost indescribable.

Allie

This may sound warped even for you girls but the first time I felt something was different was not so obvious.  I was about 10 ish (I am 42 memory little foggy on when:)) when I got to wear this bright mustard yellow shirt and yes just a shirt nothing gendered about it.  The but I do remember feeling this is great something that is not drab boy clothes but something special and it did become a favorite shirt.  Normally and even today do not have much of a favorite clothes well ok some secret stash of girly stuff:)  And yet I don't think of the crossdressing as sexual anymore its more put into a different state of mind If you will.
Ha ha does this qualify or should I have put later when I actually wore actual feminine things or am I just stranger then most:)  BTW just at the see therapist questioning self phase if that makes a difference.

As in completely dressed? probably... 9 or 10? not for long though, wouldn't have wanted to get caught.

First time I dressed was around 11 or 12.  I would come home from school, sneak into my mother's room and put on some of her clothing.

I had many experimental experiences with single items of my mother's or sisters clothes I recall from around 7 or 8, but being fully dressed as female and go out, was at age 8, when my Mom dressed me up as a nurse including white hat, and white dress outfit (she made it herself for me) for Halloween, I loved it....

C -

1974 when I first began school. I was interacting with girls my age and I wished I was one. My mother allowed some dressing at home and in public I was often androdgynous,- long hair, some jewelery,jeans,tshirt, girlish cardigan


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0 to 5 years

I wasn't able to wear women's/girls clothes when I first wanted to since my sister was considerably smaller than me and mom was an adult and I was 10-11. However, I could use my mom's makeup, and I liked the change. When I started working, I bought my first panties from Victoria's secret  (1987 or so. the Second Skin style- still love them, still fits, and still are in good shape). Panties were about it until I hit 30 or so, then I started buying clothes. I still don't have much. I have been out in public only twice intentionally and once unintentionally.

Very young, swiping my sister's clothes out of the laundry hamper.