After I returned from a year of living with my Aunt and going to school as a full-time girl, I returned a young teenaged girl. Mom and later my Aunt had very carefully dressed me in clothes that reflected an image of a very young girl. The never let me dress as an adult in party dresses.
The first real time that I went out dressed as an adult was when the owner of the most exclusive dress shop in town asked Mom if she could photograph me dressed in party dresses for a fashion layout she was doing. She wanted me to model for her but that was just an excuse to get me out to her home and play dress up with her.
Halloween was a great time to get dressed up and party. She wanted to dress me up as Marilyn Monroe with her going as Elvira to crash a couple of parties. I did look like a very young version of Marilyn and with the right dress, makeup and wig, plus a lot of padding, I knew I could pull it off.