your first time :)

[girlyman15]

describe your first time cross-dressing:heehee:

[deja true]

Gosh! Can't remember that far back ... it was even before touch tone phones! :D

But I certainly remember the twin girls next door dressing me up in one of their party dresses. We were about 6 or 7. When we heard their dad coming up the stairs, I ducked under their bunk beds and wriggled out of the dress. He wanted to know what I was doing in their room in my underpants, and covered in dust bunnies!

A bright memory still after all these decades, though it certainly wasn't the first time!

Gee!

[girlyman15]

ha ha thats funny girl

[Danica_7]

My first time was funny.

I had met up with one of the girls in the neighbourhood who I knew somewhat. She was going to a drag show. So, for some reason i suggested that she dress me up in drag and bring me. I was also only 18.

After a horrible bad drag, I drove out there and had a blast!
I felt like i could really let loose, like i wasn'tI confined at all.
So i danced like crazy and had fun!

I really didnt like the fact that i wasnt very passable. It was kind of embarassing.
But what i found interesting was how much I enjoyed it! I really started to play my role, and I enjoyed it.

[girlyman15]

ha ha nice any others ladies

[girlyman15]

Well I will go on and tell mine when I was about 7 my Istayed with my grandmother for a few days and it was sunday and I did not have any extra socks or underwear so my granny puts me in my my cousins panties white with frills and a pair of her socks they were white with puffy frills she tucked them in and it felt great

[tinalynn]

So far back... I think my first time I was dressed up by my older sisters in their bedroom after I was supposed to have been in bed. I remember them laughing and enjoying the hell out of it. I was also smiling and liking it, but don't really remember it too well.

[docrobbysherry]

----------oh CRAP! I can't compete with u CD CHILDREN!:doh:

[Janine cd]

The first time I remember dressing in a real girl's dress was when I was 8 and my mother wanted to know whether a dress she had bought for a cousin in a distant place would be the right size. Since my cousin and I were about the same size, My mom had me take off my shirt and jeans and slip on the dress. I remember that it was maroon velvet with a lace colar and little bows at the waist. I remember the feeling of velvet touching my body and the smooth satin underskirt tuching my bare legs. It was so wonderful that I could not believe it. I never let on that I enjoyed the experience, but I will never forget it.

[Karren H]

I was 7!! That was 50 years ago.... hell I can't remember shat I did yesterday!! but somehow I got into Mom's closet when they were out...... :)

[ArleneRaquel]

My first time was I was 7 or 8, trying my mothers things, among others elbow gloves. My first time attemping to be a full time gurl and going out was a complete disaster, but that is a very long story. :eek: :battingeyelashes:

[BRANDI66]

the first time was just panties. When my wife told me to put them on I said "HELL NO" after a few minutes of her telling me how hot she thought it would be I put them on for her. Well that was fun and things progressed, within 2 months she had brought me home from leather high heel boots to panties and bras ect.. At least at home I really liked the sexi look and feel

[marny]

never admitted this before but i was 9. mom had a strapless push up bra and a pair of falsies. When the cats were out of the house the mouse played.

[Dragster]

I know I've told this story before, but I was about 10 or 12 (55 years ago) with no-one else in the house and decided to try on my mother's stockings; why, I can't remember now! I also needed to put on her hookside, open bottom corset as well, for the suspenders to hold up the stockings. Then her bra to complete the look. I was shaking with excitement at the smooth silky feeling of the stockings, and the corset was so tight that the pressure on my private parts accidentally triggered my very first orgasm. I had a very rapid clean up job to do, but from then on, I was "hooked"! Corsets, bras, stockings and suspenders are still a major source of excitement for me, but there are also many others.

Tony

[BLUE ORCHID]

That was 61 years ago I can't even remember what I had
for beeakfast this morning.
I guess it was the usual getting into moms closet and dresser drawers.

.................................................. ....................thanks..........ORCHID

[Frédérique]

describe your first time cross-dressing :heehee:
I was a lonely boy, no strength, no joy
In a world of my own at the back of the garden
I didn’t want to compete, or play out on the street…
(Neil Tennant)

But in my secret life I am a …….GIRL! :battingeyelashes:

One day I put on a skirt, and my life was changed forever. I just loved how it made me feel, so I went out and began to accumulate all sorts of female clothing and accessories – one day I walked into a clothing store, saw a beautiful outfit, and bought it on the spot. I felt very, very different after that, but I didn’t question my feelings or the direction I was going in…

I kept trying new things day by day, and soon my transformation was complete - I was looking at Frédérique in the mirror, but she didn’t have a name at the time. I wish I could put into words how I felt. The dress suited me, the hose suited me, the wig and makeup suited me, the bra and panties felt nice next to my skin. I looked in the mirror again and smiled…:)

[Denise Lewis]

properly with intent - about the age of 12, my mums pantie girdle and polyester baby doll nightie, both in pink. I felt dizzy with excitement, weak at the knees. Still do to this day when I'm in a ladies clothing store

Dee

[BellaWolf]

My first time was when I was 13...a really good friend of mine talked me into wearing her denim skirt and tank top...and what do you know...I loved it! :p

[Randee]

First time for me was about age 9, coming home to an empty house, and sneaking into my sister's dance bag and trying on her dancewear out of curiousity for the feel of her skintight bodyhugging leotards and tights with silky panties underneath on me. I have been hooked ever since and always loved that tingly titillating sensation pulsing through me at the thought of slipping into the girly world of leotards and tights.

[Vanessa R.]

16 years old, after football practice-we bought a house from some friends of the family and I was over there alone cleaning it up before we moved in. There was a bag of clothes full of my mom's friend's clothes and I found a pair of white, lace and silk string bikini panties and matching camisole. Not sure why, but I eventually slipped them on. My world has never been the same.

[sherri52]

My first time wasn't my doing. My mother made clothes for the less fortunate and I was her model. She had me stand on the chest in fron of the window as she pinned the material together and then again after it was done. I was six then and hated it. I didn't start dressing on my own until I was eight and I'm not sure why I started except that my sisters always seemed to get more clothes than my brothers and myself.

[Hannah_Rose]

The first time i was probably about 7-9 years old, and i remember wanting to dress up in my older sister's clothes...so i did...alot...lol