I started wearing my sisters dresses when I was 4 years old. I use to do it when the lights went  out. I continued  through grade school , high school college. and after, I stopped for a bunch of years . I thought I had put it to rest. I started up again last year. I'm on HRT now , so I probably won't stop again.

I didn't wear a skirt or dress privately until last year and did not publically until February or so this year.   I wanted to since I was 4, but had no real access to something that fit, even if I would have allowed myself to go there.  My mother is tiny and nothing of hers would have fit me by the time I was 11!

I started doing it at night, too (privately, never tried publicly), but I was 6, I think. I've been doing it ever since, with only a short break of a couple of years during the early 90's. It has always felt natural. I don't even like men's suits, I've never liked wearing them. They just seem wrong some how.

I've been thinking this year about telling people in my family about it. It's better than trying to hide it all the time.

Chris

In private? Earliest memory was four years old, I dressed up as a princess with my friend. I've had a history of stealing my mother's and older sister's clothes, I don't think they ever found out (And I'm never telling them).

About two years ago I started wearing skirts, I stopped wearing pants. I wasn't trying to pass either.

Seven years now, I first put on a dress at 45. Hugs, Devlyn

Very early.  I can't remember the age.  My sisters always dressed me up and put me in makeup when I was young.  The first time I did it on my own was probably about 4 or 5 when I wanted to dress like a "fairy princess".   Also, I would occasionally dress up and pretend to be female celebrities when I was young.  The first time I did it in private without family knowing was probably around the age of 10.  By that time the cute young gender bending phase had ended, and I knew it was something that I was "supposed to hide".   

Quote from: Phoenix_2812 on December 09, 2013, 02:03:13 PM
I started doing it at night, too (privately, never tried publicly), but I was 6, I think. I've been doing it ever since, with only a short break of a couple of years during the early 90's. It has always felt natural. I don't even like men's suits, I've never liked wearing them. They just seem wrong some how.

I've been thinking this year about telling people in my family about it. It's better than trying to hide it all the time.

Chris

I have a problem with men's suits too, they do feel wrong

Quote from: evecrook on December 09, 2013, 03:54:54 PM
               I have a problem with men's suits too, they do feel wrong

I always hated having to wear a jacket and tie and dreaded the tuxedo more than anything.  I thought it was all because I just wasn't a suit person and didn't like dressing up, but now I realize it was a manifestation of gender dysphoria.  Manly man clothes made me anxious and uncomfortable, when you're supposed to "love the way you'll look- guaranteed."   Now I LOVE getting dressed up and looking my best, and I look forward to events where I have to look nice with hair done, makeup and jewelry.

I've only worn a dress once, and a skirt a couple times (in public) and that was years ago. The skirt was nice, very comfortable, and maybe if I wear long skirts it'll cover my huge calves lol. So skirts are a maybe, pants or pant-like bottoms are preferable, and dresses? Well, maybe on special occasions. Though, I have friends that are dying to see me in a sun dress for some reason. xD

my dad says my mom and oldest sister started dressing me up a 3? but i remember asking my sisters to really start doing around 5-6 till ,y dad said no more. then in secret until i got busted at 11

I dressed up in frilly dresses till 4 when my dad forbid my mom from letting me get into her makeup, jewelry and a bag of little girl clothes I'll never know why was there, other than my mom wanted a girl. I only had one older brother. I started again at 13 off and on into my mid thirties, then quit completely for nearly ten years, dressed a little, and stopped again till 2012. I've worn dresses or skirts every single day for nearly a year and can't see myself ever going back to pants more than one or two times a week. I love the look, feel and male response of wearing dresses. Men always open doors for me in a dress and I hated being told by society I wasn't supposed to wear feminine clothes and I'm catching up on lost time! Mira

I have been wearing dresses and skirts in private for the last 20 years I still have a little way to go before I venture out in public with them but I look forward to the day when I can.

Emily.T xx

I wore a few back in high school (in private... "borrowed" from my sister).

I don't wear them often now, but I don't dress up that often. I prefer a more blended look while I transition, since I'm not too passable in the face. I have worn a purse out, though... once. That was quite the experience.

Right now I'm on the look out for a gray or black maxi skirt. No need to freeze or show too much leg this time of year!! I have a red one, but it's enormous and probably isn't worth taking in.

Privately when I could for 44 years, publicly for 7 months.

By choice in private since I was six or seven, but I have a baby picture of me when my aunt had put a dress on me. So I guess you could say my whole life ,but I still haven't gotten the courage to wear either in public yet.

I can't say I borrowed any dresses or skirts from my sister. When I was about 10 or younger I use to sneak her jeans and shirts when no one was home. When one day I almost got caught I stopped and haven't done it since.

I have been wearing dresses or skirts for as far as I can remember.  However,  I did it privately without anyone knowing.  I haven't come out to family and friends yet.  But it has been nearly a year and half since I have slept in yikeee male clothes.  When I do go out its more of an andro look wearing girls jeans with solid color tops...

i forget how old i was, very young though, when i put on my sisters skirt while everyone was gone for the night and i was home alone, it was just a simple blue skirt,  and i had it on for about 5 minutes before i look in a mirror just break down crying and crying, next thing i knew it was the next morning, i was still in the skirt and still all alone, after that i didnt do so for a while.

Quote from: gowiththeflow on December 09, 2013, 05:36:25 PM
my dad says my mom and oldest sister started dressing me up a 3? but i remember asking my sisters to really start doing around 5-6 till ,y dad said no more. then in secret until i got busted at 11

I almost got totally busted when I was in high school. My dad came home from work unexpectedly . I had my sisters prom dress on. He kind of half heatedly chased me around the upstairs rooms but gave up chasing after me and went down stairs , never said any thing again.

I used to wear long skirts in high school. I had a "goth" phase that included make-up, skirts, fishnet shirts and bondage straps as well as knee high 4" platform boots. Oh and an over abundance of safety pins. Lots of fun times back in high school. Between my stepdad and the kids that tired to pick on me I stopped because it wasn't worth it at the time. Thank god I hated my picture being taken because I was mess as a teenager.