I probably was 7 when I tried my sister's dresses, secretly in the bathroom, rescueing them from the laundry bin.   Then, once for a lark in my early 20s for a new year's party. 

Since I went full time in July, I wear dresses all the time.  They're wonderfully versatile and I look good in them.

xxx
J

Somewhere between 8 and 10 when I was privately dressing via the dresses my sister had. The first time publicly I had worn a dress out was late 2005.
Mariah

I never really did it before.  I now have two skirts in my wardrobe as of late September and I think I'll wear them now and then, though I'm still partial to jeans and what I really want is to be able to wear leggings without an unsightly bulge. >.<

Quote from: Rose City Rose on October 17, 2014, 01:12:43 PM
I never really did it before.  I now have two skirts in my wardrobe as of late September and I think I'll wear them now and then, though I'm still partial to jeans and what I really want is to be able to wear leggings without an unsightly bulge. >.<

Totally feel you on leggins! Super comfortable...

The first time I ever went out was this last July 6th. Previous to that, I had only been putting on female clothes  at home a little bit more than 2 months. Never did it before that.

My limited cross dressing in private lasted about 20 years.  After accepting myself as trans in late 2012 I started the New Year right and went public FT and did not wear anything but skirts and dresses for about six months.  Now I find my comfort range includes jeans, capris and scorts.  This freedom to wear what feels good is incredibly liberating and empowering for me.  The rainbow tutu in my pic is for special occasions like gay pride and Halloween.

Never had a second of cross dressing in my life.
The first dress or skirt I ever wore was after I came out and started living full time.

I always fantasized having a full  wardrobe of skirts and dresses from very early on with no male clothes to be found. All I have left to dispose  of is  a suite  and three pair  of work jeans