Wednesday, July 19, 2023

Angela’s First Time(s)

By Angela Booth

I was four-years-old and my mother dressed me for a fancy dress competition for a small village fete. I recall wearing one of my sister’s dresses, which was to my feet, a fur stole, heels, beads, floppy hat and a bit of makeup. The theme for me was “Lady Muck” – a haughty or socially pretentious woman as an expression of the early 1960’s. 

I won and rather liked being dressed – the trigger had been pulled. 

When I went to school, the girls wore such nice dresses, as did my sisters, so any opportunity to try on dresses was taken. There was the play box of old clothes that I would delve into and there will be no guessing what I wore. It was fun and my family went with it. In secret, I discovered that girls wore more than dresses!

I dressed again for fancy dress competitions and my mother made me a rather lovely fairy dress to wear for a school play when I was about eight-years-old. 

I always felt more comfortable in girls clothes and in the company of girls, contrary to the social norms of the time, I never thought it was wrong – it was the others. The only time I recall an issue was when I kept wearing a dress for the day. My eldest sister commented to my mother, although it wasn’t anything harsh, but I did continue for fun and also in secret. Growing older, it became getting fully dressed up, looking the complete girl, even with boobs.

The last time I dressed fully for “fun” before puberty was to enter a beauty competition where I was dressed up by mum and elder sister. I was about thirteen-years-old. Wearing a lovely blue dress of my sisters, that I had sneaked on many times before, with padded bra, loving every minute parading around the floor. So many people didn’t realize that I was a boy and then gaining a win with a nice cash prize was icing on the cake

Then came puberty and having to conform to social norms. Having grown out of my mother’s and sister’s clothes, this became the dark ages. Of course, the desire never went away and would come out on occasion until the time was right to blossom once again.

Source: Rue La La
Wearing Hale Bob

Helene avant aprés
I welcome all Femulate readers to submit Before and After photos for publication here.
Just send your photos to stana-stana at-sign


  1. That's a beautiful story and having such an open-minded Mother and sisters must have been amazing.

  2. You looks splendid... so femme

  3. AnonymousJuly 19, 2023

    Angela, I loved your story. You look lovely in your pretty dress. Such a lady!

    My first time involved my sister and older cousins. I was about five years old and my sister and I were at their house. The girls started excluding me from their play, but finally one of my cousins said that if I wanted to play with them I'd have to wear a dress.

    Next thing I knew being put into one of my cousin's dresses. It was powder blue with puffy sleeves and a white kind of apron. I wore one of their petticoats and ankle socks along with a pair of black Maryjanes.

    At the time my hair was kind of longish with this Dutch Boy look. The girls put a little butterfly clip in it and took me outside where they introduced me to neighbors as their cousin Suzy.

    I don't know if people really thought I was a girl or not, but at the time I believed that they thought I was one. I liked it.

    After some time of being cousin Suzy my uncle and dad came back from wherever it was they had been. Dad looked shocked and my uncle said, "looks like you have another girl."

    Dad didn't like that and demanded I take off the dress.

    On subsequent visits with my cousins, they dress me up as a girl, but we were careful not to let the grownups see us.

    The last time I dressed up with my cousins and sister I was about 12. They stuffed a bra for me to wear under a nice dress along with nylons and a slip. They made me up and kept telling me that I should have been a girl.

    Now many years later it come up every so often and girls comment about how much fun they had playing dress up with me. I loved it too.

    1. AnonymousJuly 20, 2023

      Love both stories. I wish my childhood would not have been so repressive.

  4. AnonymousJuly 19, 2023

    Angela, What a lovely story and a lovely photo.
    Penny from Edinburgh.

  5. AnonymousJuly 20, 2023

    Dear Angela ,
    I have read your wonderful stories on another cd site a couple of years ago and they still give me so much to think about .
    Thank you, 𝓥𝓮𝓻𝓪

  6. AnonymousJune 29, 2024

    Oh for the old days

  7. AnonymousJune 29, 2024

    I can relate