Yes I have. many times. Started going out when I was 17. I love it. I feel it’s the ultimate crossdresser experience. it is euphoric exciting and thrilling beyond imagination. But it also very scary. In all honestly, for maybe 100 times I’ve been out, I chickened out 2000 times.
So many times I was dressed, ready to go and all excited about where I was going to go and what I was going to do. Then fear set in and stopped me. Even when I do eventually go out, it is pushing through lots of fear, and only because in some cases, desire becomes stronger. I also find I was much bolder in my teens and early twenties.