THE OFFICIAL: What were the first items you wore?

[Kittie]

An all in one of my wife's but I hadn't told her

[Ginny Jones]

Hey Guys!

I am reliably informed by my Mother that bra's were the thing when I was an infant. She'd lose track of me and discover that I'd sneaked off to their bedroom and was now decked out in four or five bra's .... all on my head! I would have been 2 or 3 then. Still - it's a learning curve isn't it!

Ginny x

[Ashley Rose]

My cousins nylon, ruffled white panties. Had an "accident" and mom thought this would "Stop me from that happening again". Sorry mom! All downhill from there.(See post in "My Beginnings")

[Anna]

My first time? Gosh that was a lot of years ago!

I suppose it was one of my mother's nighties, and I got caught wearing it and got a good hiding for doing it! Didn't put me off though. Soon found stockings and a girdle, then a slip. I was hooked!

[Carol Esme]

My mother's silky panties. I wore them to bed instead of my flanelette pyjamas and the feeling was so great I had my first ever climax. Aged about 14 I guess.

[Latanya]

locked in the bathroom putting on silk stockings and attaching to garter belts and like carol had my first sexual experience and i guess hooked ever since!!

[Karin]

Socks.

Even before Karin, I only wore girls socks. White ones, pink ones, any ones so long as they were girly. I had about 600 different pairs of girl socks at the time Karin showed up.

Well you did ask!!

[Andrea]

Wow the memories this brings back... I must have been about 12 I spent the night at a friends house... I got up in the middle of the night to go to the bathroom and noticed a pair of my friends sisters pink bikini panties (silk or satin or whatever that material is) sitting on top of the hamper... I got curious so I picked them up and I liked that soft satin feeling on my finger tips so I started rubbing them all over my body... Then I thought what would it be like to wear them... So I took off my boxers and put on the panties and WOW I was hooked from that moment on... A month or so later I spent the night again waited until my friend was asleep and headed for the bathroom... Dug through the hamper looking for those pink panties that made me feel so good so special so pretty so femme... No pink panties... This time though I found his Moms white bra and a pair of his moms white satin bikini panties that had multi colored polka dots on them... Didn't take long for me to get out of my boxers and into those panties and that bra... I'll share more soon...

[Riley Evans]

The first thing I wore was a red front closing bra that I found one day, I was amazed because up until then I had only seen white and beige, but the red really sparked my interest. I wish I still had it.

[Justine]

The first things I ever wore was nearly a full outfit. All I needed were some shoes and makeup to complete it really. I had on panties, a bra, pantyhose, skirt, blouse, the works really. Curtesy of my mothers closet of course.

But, that was over 10 years ago, and I am barely starting to look back at that moment.

[Susan Fortier]

That's easy and fun to recall; I lost a bet and had to dress as Marilyn when she stood over the subway grate in "The Seven Year Itch" at a Halloween Party.
It was the first time I'd cross-dressed (and I thought the only time) and my GF at the time bought all the right things: Wig, makeup and the white dress, as well as the foundation garments.

[Miss Conny]

The very first item I wore was a white corselette quickly followed up by nylon stockings held up by 6 straps.
Then panties and a black pencil skirt and a white blouse. Then followed 3,5 in high heel black shoes and a black wig and finally a very red lipstick, a pearl necklace and earrings.
Reason? A party with 5 other married couples, where it was proposed/decided (by the ladies) that they should be dressed like men and off course we men should be dressed as women.
My wife worked in a big warehouse wherefrom we got the female underwear very cheap and it was intended to throw it away afterwards - BUT
I kept it secretly and took it on now and then when I was alone.
Why? - I don´t know - it was eventually thrown out and I was busy at work so I had no time or opportunities to continue.
And yet - my work required now and then some travelling beeing away from home 3-4 nights, so I began shopping for stockings, girdless. bras etc and did the CD-ing at the hotel.
My wife pasted away, and after being single I am - almost every day - wearing female underwear, corselette or bra and garterbelt or roll-on and nylon stockings under my male clothes.
I have pair of D-cups breasts - and in the evening I dress up fully.
Nobody knows - I think - and I have nobody to talk with so therefore I joined this forum.

[Angela Newel]

My mom's nylons. I just loved the way they made my legs look. Still do! :-D

[Miss Conny]

Hi Angela
I love nylons as well, but mostly the feeling of them, wherefore I use them almost every day held up by a white garter belt with 6 straps. I wear them now
Using garter belt or girdles, I think starts with my first experience wearing women underwear as I have told about in the above.
Best whishes and a

Connny

[Marie]

What a wonderful memory this question sparked! I was first crossdressed by my older sister. It was only a dress that she put on me over my other clothes. There are pictures in the albums of me smiling away while dressed this way but only dimly remember this as I was 4-5 years old. My father wasn't part of the family at this time of my life, parents were separated for several years before getting back together when I was 10-11 years old, so was raised by mom, sister, and grandmother. Lots of fem identification early on in my life. We moved to a different house after my parents remarried and life was good. The new neighborhood was alright but I was a small shy boy and wasn't into sports like all my classmates since I hadn't been raised to them. I was bullied some and so wished that the boys liked liked me better. I noticed that the girls seem to have a better time of it (know now they can be mean to each other) and sure wished that I could live in their gentle softer world.
I will always remember the day I found in the basement store room the box of clothes that my older sister had outgrown. My mom never threw anything away and there wasn't anyone to pass these on to but nevertheless there they were. Panties with lace waistbands and leg openings, anklets, a pettislip, two dresses, and a training bra were the treasures in that box. I was so fascinated at seeing these and getting to touch them. They symbolized the life I wanted to have. I had to try them on. With trembling excitement I removed my clothes and picked a pair of white satin panties with red lace trim from the box and tried them on. What feelings overcame me! Got aroused and didn't know why or what was happening except that it was a feeling that I'd never had before. I had to keep going so picked up the bra. I figured out how it had to fit and fastened it on to me. I was feeling hot and flushed now and stepped over to a large old oval mirror hanging on the wall. I was red all over because I was so excited. But looking back at me was a transformed me, a girl looking me! I was shocked and so pleased. Running back to the box I quickly pulled on the pettislip and then one of the dresses over it. Back to the mirror I ran, so anxious to see what I looked like. This was the beginning, my escape into girlhood.