A bit disappointed. It was a very plain dress, not sissy-like at all. He wears his street sneakers, no girl's stockings, no makeup, no hair done, & underneath he wears plain plaid boys boxer underpants. But I bet it was a lot like our first time we ever tried on a dress.
I did better my first time in a dress. I was about 7 one summer when everybody was busy outside the house. I went upstairs & put on a pretty little girls red sailor dress with blue trim, & puffed sleeves. I even put on matching red tights. It was beautiful. With everybody just outside the house, I had quickly put it all on & took it off in about only 10 minutes. But I still remember it in full detail.
I started wearing girls stuff before then, with girls tights. I loved the look & feel of them on me. Later I tried on some old fashioned little girls ruffled bathing suits (1960s). Back then my baby sister was actually a little taller than me even though she was 3 1/2 years younger. So at 7, her girls stuff, made for a 3 or 4 year old fit me fine.
But when I tried on a dress for the first time, I was hooked, & wished I had pretty dresses every day. As the youngest boy out of 5 of them I never had any nice boy clothes. They were always old, out of style hand-me-downs that never fit well. So I grew to hate my boy clothes. My sister was the only girl in the family. So she always had nice new pretty things.