What item of clothing got you into cross dressing?

Panties here easy to conceal and hide follow by old dresses I found that where going to the garage sale as a kid 

For me it was my mom's panties when I was 6 yrs old. Felt so right.

For me, it was an open bottom girdle at 9 or 10 yrs. old.

 This is included in the story I told in the thread I started a few weeks ago. 

 It wasn't clothing that got me started, it was jewelry, specifically costume or fashion jewelry. I liked how the bold shiny necklaces and bracelets looked on women and it looked so fun to be wearing them. As a small boy I would sneak into my sister's room and try on her bangles and such. 

I didn't get into trying on women's clothes until later. For some reason, probably so it wouldn't get crushed by the other clothes in my sister's and mother's closets, my mother agreed to let my sister keep her high school prom dress in my closet. I was strictly forbidden to touch it, of course, but with my sister now away at college and me being old enough to be left alone at home, the urge to try the dress on because irresistible. It was a pretty 1960's style dress, long powder blue satin with white floral lace covering the bodice. No sleeves, and a rounded neckline that didn't go low enough to reveal any cleavage. Remarkably enough, I fit into it easily. 

But then I noticed I needed to fill the cups. A white strapless bra stuffed with a pair of my socks rolled into something resembling breasts took care of that. Then I added a three strand faux pearl.necklace from my mother's jewelry box. 

I even found a pair of my sister's mid heel white shoes that also fit me. The style didn't match, but I was too enthralled by what I saw in the mirror to care. 

 I've always felt it an amazing coincidence that the dress appeared in my closet right around the time I was entering puberty. My upbringing was no more and in a few cases less repressive than that of my peers, but these were times when the mere mention of crossdressing and many other "adult" topics was seriously taboo. And yet it's like I was meant to try that dress on. I'm not superstitious but something seemed to be at work there. I'm going to leave it at that but I'm going to take another look back at it. 

Meanwhile thank you for bringing this memory to the forefront. I'm still new here at CDH but obviously not new at dressing up. 

Rayna 

I was young. My brother dared me to put on my moms panties. Then it became put on as many as you can. lol 

I think it was 10 pairs. They must’ve been so stretched.  lol. 

that was it though. 

I remember when I started up again in high school. 

My first time crossdressing was trying on my moms lingerie. It was a white garterbelt and matching stockings then it was a white lace thong,then later it was a black lace tedd. When I was older it was my sister's cheerleader outfit and then her prom dress. It was blue satin with a deep plunging neckline. Then it was my sister's friend's french maid costume. When I hit my twenties it was a red babydoll with matching panties. When I moved to North Carolina i got a job and then i ordered from adore me. After that my collection of feminine gorly things has grown.

Right now as i replying i am laying in my bed in a flower matching bra and panty set under my grinch dress in red ballet flats.

I was a "Mummy's girl", ( I dont have any sisters). I remember trying on her bras, open bottom girdles and an old one piece swimsuit that for some reason lived in our laundry at the back of the house.

As for boobs, tennis balls did it for me, didn't arf", (half) itch on my chest.

Caty

My first recollection - Well it was 53 tyears ago was me being approximately 9 or 10 years old and my sister put her nightie on me in our bathroom. I loved the feel of it - I have mentioned this to her recently and she doesnt remember but for me it was the catylyst to what eventually became Ellie. Since then it was my sisters clothes when possible then my wifes until I told her about Ellie, and from that moment on Ellie became real in our lives and now I have a whole wardrobe of my own clothes. No need to borrow anymore.

As I recall when I was very young I would play dress up with my sisters with costume dresses and heels. When I was around 12 and home alone I tried on my mother's panties, garter belt, stockings and bra. I loved the way they felt and would dress in them whenever I was home alone. 

XOXO
Suzanne

I'm not sure if your question is how did I commence my inventory of clothing items, or what did I first put on "and it was off to the races!"

In my case I did not "catch the bug" after whimsically putting on that first item of women's clothing, but rather, after years of occasional dressing I have now easily transitioned my life to fully dressing en femme as a result of making a decision to "stop fighting it" and no longer trying to subdue my feminine nature.

But for the record, my first worn item was pantyhose during my late 20's.

Dani

It was my older sister's panties for sure.  I just loved they way they looked, so soft and satiny.   I remember as young as eight years old, stealing my sisters bras and panties so I could go try them on in secret.  I never returned them either.  Something tells me my sister must have known, but if she did, she never said anything to me; in fact, when she was old enough and moved out of the house, she left a small collection of clothes behind which of course, very quickly became mine.  In hindsight, I suspect she left those things behind because she knew what I was up to. I guess I will never know, unless I specifically ask her.

Hi Joanna,

When I was very young, 5 or 6, I shared a bedroom with my aunt. When she was out I would sometimes go through her dresser drawers and admire her feminine clothes. I recall wearing a short slip as a dress, having it pulled up to my armpits. Mostly her clothes were way to big for me to try on.

I tried on my mother's things a few times when I was in my young teens. Including pantyhose and a bullet bra.

But I don't really consider those events as the start...

For me that event occurred when I was 48 years old. I was divorced from my first wife, and unattached when I just happened to turn a corner around an aisle in a discount department store, and my gaze gell upon a peg board of panty 3 packs. Something just clicked and felt right. I deliberated for a few minutes over sizing and chose a 3-pack in size 8 with beige, black and an animal print. They were nylon with elastane. Only a little snug and very comfy.

Happy Holidays and Hugs,

Autumn

I was intrigued with my mothers lingerie and would sneak into her room when she was gone to dress up and explore.  I most loved her girdle and stockings (probably because her dresses were too big for me at my age).  I remember trying to wear her heels but way too large for my feet at 6 or 7.   

As a young teen I would wear a vintage corset, when the house was empty

Erika