When I was younger I had a babysitter who would dress me in my sisters clothes. It started off as a joke but eventually every time my sister would leave for tennis or piano lessons she would dress me up. I’m talking head to toe. Tights, panties, dresses etc. my sister was 2 years older then me so her things fit well at the time. At first I didn’t enjoy it but after a while I started to look forward to it. It went on for a couple years then my sister got old enough to watch me. After she stopped babysitting I continued to dress up even to this day.
Source: reddit.com/r/gonewildstories/comments/9qf15m/mf_dressed_up_in_my_sisters_clothes