Wednesday, September 13, 2023

Early Heather

By Heather

My earliest recollection of being crossdressed was when I was a very small child.

My mother dressed me in a blue dress with smocking on the front, white socks, white shoes and a hat which I think was made of straw. I remember standing at the top of the stairs while my mother fussed to make sure everything looked just so. That is all I remember, but I know my mother took at least one photo.

Other recollections go back to my childhood when I was probably only four or five years old. 

We had a room called the play room in my parents old house. In it were all the toys that my sister and I possessed and a dressing-up box. I don’t know where the clothes came from, but I do recall there were a few child’s dresses.

The game was to march up and down the room a few times and change dresses pretending to be witches, princesses, brides, etc. I don’t recall pretending to be anything masculine. I don’t recall making any conscious choices about this or thinking that there was anything wrong with dressing up. It was just something we did.

When I went to prep school, the games came to a natural end and I seemed to forget about them. One day, however, I returned from school and saw a girl’s full-skirted petticoat with shoulder straps on my parents bed. It was obviously something of my sisters.

All reason or thought of being caught went out of the window. I stripped there and then and forced myself into it with a great sense of excitement. As quickly as I had put it on I took it off, but the sense of excitement and of having tasted forbidden fruit was there. 

This I think was the real beginning as the previous experiences gave rise to no such sensations.

Source: Ted Baker
Wearing Ted Baker

Yours Truly


  1. Is this a female impersonator?

  2. For many there always seems to be a "gateway" piece of women's attire that sparked or released the girl within us. For me it was my mother's full nylon slips that she hanged to dry in the hallway to the bedrooms. I love the feel of the silky nylon and could not resist the urge to take them down and slip into them. I had no thoughts of wanting to be a girl. It was strictly the love of the material.

  3. There are a 1,000,000 stories in the "T-Community". They are told by us individually, however, all the same exciting story. Heather thanks for sharing "our" story.


  4. That leather dress and gloves are wasted in that bar, she should be grocery shopping!

  5. Thank you so much Heather for your story .

  6. My cousin Cindy and I were born just a few months apart, and my family and hers lived in the same two family house. Apparently, my Mom had been told ( via some "old country" traditional method ) that I was going to be a girl, just like my cousin ( other than anatomically speaking, the tradition was, in fact, correct ! ) . Anyway, Mom decided that it would be cute to dress me up in my cousin's frilly girl clothes from time to time . Sadly, I have no recollection of any of this , but I can honestly say that I crossdressed before I could walk !

  7. Heather, did you ever find out why your mother dressed you as a pretty little girl?

    The clothing box game you played with your sister was fun! When I was little, in grade school, the kids in the neighborhood had such a box. One of the moms was an expert seamstress, and had a ton of clothes that were ours for the taking. So we kids would grab something from the box and make up a game or story. Before long, one of the girls -- Sue -- objected to having to always be a girl and that the boys needed to play those parts from time to time. As I recall, the boys didn't put up any objection, so we would occasionally be the girls. It was great fun, especially for this little boy who had discovered my mother's lingerie in the wash basket!

  8. The before-after photos are interesting this time. Doesn't the cis female look uncomfortable in the photo on the left? Contrast that with her obvious comfort with the pretty blond in the photo on the right.