Oldest memory of your crossdressing

[Estefania]

If you consider yourself a crossdresser, how old were you when your first experience of VOLUNTARY crossdressing occurred? Nope, not if somebody dressed you up, but when you remember that out of your free will decided to try on an article of women's clothes? Many have posted that in their own "my beginnings" thread, but I think it will be interested to see the combined results...

Only fair I get started...

My oldest memory of my crossdressing I would have been 3 or 4 years old. I remember taking the red knee socks from my aun'ts school uniform and wearing them under the bed covers. Not sure if that was first or second to my getting inside her closet and wearing her school jumper.

So, no, no sexual component to how my crossdressing started. I wonder if the fact that my "beginnings" were not lingerie related have shapped (npi) my dressing, as of why it has never been "my thing".

Hugs,
Gaby

[Requal Jo]

I still recall my sisters dressing me as a girl when I was 3 years old. Whether that is through stories told I do not know.

However I remember taking dressing seriously at age 14 years when I then consciously dressed in my sisters clothes. There was nothing sexual about the dressing, it came naturally.

I am now over 65 years and Requal has been making very frequent appearances for the past 4 years.

[DonnaT]

I had the desire at age 6, but didn't get around to it until 9 or 10.

[Martha G]

I had the desire from a young age.

But it took a costume party and me dressed in a beautiful hoop skirt as Charley's Aunt to make the desire to become a reality. I was 59.

I am now 74 and have enjoyed 15 years of dressing and acting like a woman when I can.

So sorry that I missed so many years.

Dressing as and acting like a woman is just great. I love to explore my feminine side.

[Berta G.]

I was the 2nd and last child and my brother was 6 years older than me. Everything I've been told is that my Mom wanted me to be her "baby girl" and my name was to be Roberta. She made sure that all our relatives and her friends were aware that she only wanted baby shower and any other gifts to be for a baby girl. (I was born in April, 1940 so none of today's electronics were available back then to pre determine gender.) Every baby picture I have I'm wearing lovely satin baby girl outfits and know I was dressed this way until I entered kindergarten when she was forced to start dressing me in little boy clothes.

As I look back at that time of my life I feel that my love of satin caressing my body today and for 30+ years was probably instilled within me during my infancy and being dressed in those 30's early 40's fine vintage satin outfits, slips and panties! One of my weekly chores was to help my Dad with the laundry on Sat. mornings. These were the days of the wringer washers and 3 set tubs for the 1st rinse, bluing rinse and the final rinse. It was my task to hand the laundry items to my Dad from the machine and set tubs so he could put them through the wringer. I did this again when we'd taken a load out to hang up to dry. While doing this I loved the feel of my Mom's lingerie items, mostly satin or the super silky nylon tricot prevalent in the 40's. On one occasion my adolescent fingers touched something like I'd never felt before. When I pulled it out of the water to hand to Dad I realized it was one of her nightgowns that I'd never seen before. It was made of the silkiest satin I'd ever put my hands on even though soaking wet. Dad spoke up and said be careful of that as Mom just bought it and you should hand it to me. When I felt it again at the hanging up and then got a complete look at it in all its silver satin glory and huge flowing skirt I had feelings like I'd never felt before. (NO, not sexual! I had not yet reached puberty!)

On Sunday after noon time Sunday dinner my parents asked if they could speak to me about something. (Now again remember I'm talking the mid 1940"s here. Those were the days when most families went to Church in the morning and then came home to a family Sunday dinner and after clean up did family things together like visit relatives or friends. There was no TV, no Professional Football or other distractions from family togetherness,) So I told them that would be OK. This had me a bit worried as I had no idea what was on their minds and just what I might be getting punished for. Finally all the dinner clean-up was done , dishes washed, wiped and put away in the cupboard. We went into the living room and Dad began by asking if I'd mind being home alone for 3 or 4 hours after school was over. I replied that since I was starting the 4th grade and the school was only a block away from our home I didn't see any problem with being there alone. I followed this by asking why this was being asked of me because Mom was always home to greet me when I arrived home from the school I had been attending which was a 45 min walk away. They explained that Mom had been offered a full time job and they needed the money as my brother was getting close to college age plus other expenses of home ownership. I told them this wouldn't be a problem and when would it start. They thought in a week or so as Mom had to call on Monday and accept the position,

Now I hadn't had any other thoughts about this change in my adolescent life and figured I'd get home, have a snack, change clothes and go out to play with the neighborhood kids. That all changed that September afternoon when I'd walked home in the pouring rain which meant there would be no going out to play this afternoon. Once in the house I realized I was soaked to the skin so I headed to the bathroom to get out of my wet clothes and dry off. On my way to my bedroom I had to pass my folks bedroom I noticed Mom had a pile of her silky slips and nightgowns on the chair by her bed!! Oh, oh there was that strange feeling overcoming me again. I reached down and ran my hands thru that exquisite pile of sensuous feeling fabric. I picked up a handful and rubbed them against my bare skin. I decided this wasn't enough and selected one of her floor length satin nightgowns. When I slipped this over my head and felt that fabric embracing me as it cascaded down over my 8 year old smooth bare skinned body with its extra length puddling around my feet I thought I was going to collapse. I stayed in that nightgown for the rest of the afternoon, having my snack and doing my homework. From this day on many of my after school afternoons were spent in the house no matter what the weather outside was.

So there you have my super long story of how Berta "crossdressed" voluntarily on her own for the first time. There is a lot more I can share and hopefully will have the opportunity to do that at some future time as "Berta" doesn't get out of "her closet" very often anymore.

Berta G.

PS: Happy Valentines Day, 2017 (that's when I started this post.)

[Estefania]

Berta,

Thank you very much for sharing with us!!

Gaby

[Angie G]

Hi Gaby my first dressing was very now and then some as a teen and after geting married. Really got into it in the past 11 years after telling my wife who is great abuot it and even buys things for me. I remember trying shoes that were always to big.
Angie