first article of women's clothing that u tried on

Mentioning the one-piece bathing suit... brings back memories.

Pretty sure it was an old bra of my mothers....w-a-a-a-a-ay back a long time ago.

Boots!

High heels, way way way way way back though, and I just did it cause I thought it was a "fun" thing to do.

sisters panties

Bathing suit - ashamed to admit it was "borrowed" from a clothesline and I went for a late night dip in Lake Erie! (I put the suit back reluctantly)

Sisters pantyhose...

my moms panties and stockings/pantyhose and a really pretty sweater she had

It would have to be either my mother's panties or pantyhose. I was so young I cannot remeber exactly.

Hmmm, I must've been about five when I tried on a pair of my older sister's tights. The intent was to play "Superman," But the sensation was so super that I never got over it. Next was a few times in college, but I was just goofing around. I finally got the swing of this hobby in 2006, and Christened myself, "Jillian." And damn, I thought golf was expensive.

Sister's panties...I'm not sure what drove me to wear them but I can still remember how much softer they were than my underwear and how jelous I was.

My mother's stockings at 5yo.

I think I was 12 and I was home by myself. I went into my mom's closet and tried on a few of her dresses. At that time I had no idea what crossdressing was but I knew that I wished I had been born a girl.

I came across a pair of panties that I tried on. For a while thereafter, those would be the only types of women's clothing that I would wear. I fell in love with thongs! Some time, I want to try other types (like bikinis).

Michelle

That would be pantyhose

At age 8 I first tried on Mom's black nylon panties.......The rest is history!!

Pantyhose seems to be a common answer; no different for me, but as I mentioned in another thread there's a picture of me putting them on while I was still in my crib. Now you don't get much earlier than that, do you?

After that it was still pantyhose and nothing else until about 11 or 12 when I branched out into the other underthings. Out of mom's drawer, of course.

That would have been one of my sisters Dresses.

First, I can't believe the ages of the people when they first tried stuff on. Further reinforcing my notion that the propensity for being a TG person is something u are born with. I first tried on my Mom's bra, pantyhose and burgundy leotard. I used other pantyhose to make boobs. Very vivid memory.

Pair of Grandmother' pantyhose when I all of 4 years old...kinda ironic, since I wouldn't be caught dead with anything but bare legs and open-toed heels today!

My now ex-wifes panties and bra.

The first article of feminine clothing I wore was a slip. My mom use to hang her hand washed slips in the only bathroom. At first I tried sliding into them as they hung wet. Ultimately I would put them on, wet or dry, and, then re-hang them. I loved the slinky feel of the nylon. Now I own numerous slips, full and half slips, in a rainbow of colors. I love wearing a lacy slip under a pretty dress. My favorites are lacy ones with shadow panel or double layers. My favorite color remains pure white.

At a very young age me and my sister use to play house and one of the things we did was put on our parents shoes. For some reason I always tended to choose the pair of black stiletto shoes. I could not have been more that 5 and I already knew I had a preference for feminine things. Too bad it took so long to realize what it all meant.

The first item of Woman's cloths I tried on were panties

I talked my mother into dressing me up in a "girl" costume for Halloween.