I don’t know if this counts, but it feels like it was my first time out in public as a woman. Other than Halloween where I dressed up as a female pop star at a small company event, I’ve never been in a public venue in obviously female attire (dress or skirt, female hair, not just tight pants). In this case two days before Christmas I donned a “girl elf” costume, with green and red striped leggings, modest amount of “boobage”, blonde bob wig, cute bows on my shoes and on the back of my head, and surprised my female friend who lives nearby with this outfit. After her initial shock but also approval, we took a short walk through a neighborhood shopping district. The cute thing is, and actually a telling thing, is that she was concerned if I was going to walk home, even though I had an overcoat (which I didn’t wear during the neighborhood walk) that covered everything but the legs and hair. Basically she felt I looked so much like a young woman that she was concerned for my safety! (I did drive over, though).
I don’t think I could have done this had it not been for the pandemic which as others have noted gives us an easy way to cover those features which are most difficult to transform. During the walk I noticed several heads turning from cars and along the sidewalks which was quite delightful! She encouraged me to stop off at a store to go shopping before going home, and I almost did but I chickened out. Oh well, maybe next time.