What was the first item you wore?

[BLUE ORCHID]

It was probably the little white gown my mom put on
me when her and my dad first brought me home from the hospital
67 years ago next month.
So my crossdressing probably started when I was a couple days old.
.
.................................................. ...............thanks........ORCHID

[shirley1]

I think it was my moms shoes, stilettos, I could get them on at 12/13 years, must admit it was a thrill, I now identify as pre op transsexual, but there was a brief time as a kid when I did get a buzz from trying certain things on.

[victoriamwilliams1]

My mother red high heels

[benny68]

My mother's black nylon slip and french knickers.

[curious5752]

My first time was at age 11 mom and dad had to go out for a while so I went into their room and found a pair of mom's nylon stockings. As I put on the first one the feelings swept over me the only thing I can say was WOW and as I put on the other I was hooked on my mothers clothes. I wore her clothes every time I was alone at the house. They were to big for me because she was a a plus size but the feelings were awsom all the same.

[Alix]

Some of my friend's sister's lingerie

[bridget jones]

I was 6 or 7 years old when I went into my neighbors laundry room(they were outside back then).I wore panties and a camisole and have been dressing off and on ever since.

[Didi]

My older sister's girdle and stockings

[Carole Cross]

My sisters beige skirt suit, I was 3 years old, my sister 5. I later weny on to try many of her clothes. I now buy my own and will never buy male clothes again.

[kymmy008]

would have to say it was my mothers white silk G-String and since have been in the closest up until 3/4 months ago

[KIM SLIMS]

My sisters lei jeans .still have them

[brassieres]

Officially it was my mom's bra when I was only 8 or 9 but did not know how to hook it in the back. Within 2 years, one of my mom's friends daughter, who was just slighter older than me secretly put my hair in rollers. We quickly took them out before my mom could find out.

I also wore a pair of my moms best friends high heel leather boots too. This was in full permission of both my mom and friend. Those were my first experiences.

[Jacqueline Vasquez]

I sneeked into my moms bedroom and put on her bra and i stuffed the d cup bra and had huge boobs! it felt so good, i felt so sexy!

[Melissa1111]

My moms lingerie! LOL

[renneeists]

My first wifes things. Then she got bigger then me and I had to start buying my own. Thats also about when I started dressing in front of her. Didn't go over well at first

[Danielle76]

For me it was a black dress of my mother's. I was around 13 or 14, I think. It was hanging in the bathroom, and everyone was home at the time. I looked at it, and I was horny at the time, and thought of how good that silky material would feel, so I tried it on in a flash. My heart was about to leap out of my chest, I was so nervous...half expecting someone to walk in and find me. I wore it for about 5 seconds, then hurriedly took it off and prayed no one would ever find out what I did. It wasn't long after that that I was home alone and went through my sisters drawers, curious as to what I'd find. I found a black silk slip and stockings...holy crap. I felt like I struck gold. I tried it on and got an instant boner. Almost 20 years later, and I still absolutely love dressing up.

[diapersissy]

What was the first item you wore? A nappy

I still do

[BonnieJG]

well for me it was a bra

[try something new]

My first items were sexy panties and a Teddy. Didn't get interested in makeup until later. Then it was my wife's panties and a real shot dress that I would use when I drove a delivery van with a sliding drivers door.

[Michelle_Anne]

My mother's bra

[Caity]

We spent the holidays with my cousins while growing up and during Christmas when I was eight years old, I tried on my cousin's white panties.

[Nicola2876]

I wore a pair of tights and white panties at my Aunties house when I was five. Started wearing tights and stockings regulary at about ten.

[Bailey_in_Mansfield]

My very attractive cousin's bikini, when I was about 11 or 12. That first feeling of smoothness was so arousing.

[Crossjoerg]

At 16 a white panty-girdle of my sister, followed later by Playtex Rubber girdles.

[Ugly Michele]

Was my sister's nylon bikini panties, and white slip. Now I like wearing it all.