Sailor Dresses


Est. Contributor
  1. Sissy
In my thread regarding sailor suits, I did mention that I would do a thread on sailor dresses.

Sailor dresses were very popular and fashionable in the 1980's, probably due to Princess Diana. I remember walking along a street when a young woman walked past dressed in a white sailor dress. I was envious. "I wish that I could wear a dress like that" I thought to myself, with a stirring in my groin.

There was also the time when I saw a market stall selling sailor dresses and I fantasised about purchasing one. (At that time, I wasn't well-off financially).

Another disappointment was when I saw a sailor dress on display outside an antiques shop. Inside the shop I enquired about it, only to be told that it was "For display purposes only" and that maybe I should "Try Laura Ashley instead ".

My sister used to have a mail-order catalogue, and I would drool over the sailor dresses worn by female models. (There was even a sailor playsuit).

I did eventually managed to get the chance to wear one. It was during one of my visits to "Auntie". She would often buy female clothing from charity shops and make me put them on. On one occasion, I had to put on a blue sailor dress.

Hopefully. I will eventually be able to purchase a sailor dress. I can then imagine being under female domination and being thoroughly humiliated by my clothing.
  • Like
Reactions: sissybaby34, Seasonedcitizen and drippydrawers


Est. Contributor
  1. Adult Baby
  2. Diaper Lover
  3. Little
I love dresses, my favorite are Tori Richards.