Mine is probably going to be very different to everyone as I have just started crossdressing however my proudest moment would have to be ordering my first set of clothes the other week and wearing them for the very first time.
For months (even a couple of years), I have been trying to build up the confidence to buy my first dress, bra and underwear and never had the guts to do it.
Only a couple of weeks ago, I finally had the courage to do it and when I got my first order, I jumped straight into my clothes and felt beautiful and at peace.
Might not mean a lot to everyone however it was the most proudest moment for me (so far).
That will probably change for me (no doubt) in the future but I wanted to share my story.
Lots of Love,