I think I’d approach the question from a different angle.
First, I’d say my proudest moment was summoning the courage for my first session. After years of curiosity and web surfing, it took a lot for me to make the appointment, call from a street corner a block away for instructions, walk up the steps to the dungeon and enter a new world. I was scared to death, sweating like a pig. But overcoming that fear was life changing.
Second, I’m proud for embracing dungeon life and the fact that it makes me fulfilled. BDSM (I’ll use that term to broadly cover a wide array of dungeon activities) is not socially acceptable. We are told it’s for perverts and degenerates and not something in which we should engage. But over the last decade I’ve realized that it’s ok to enjoy crawling on the floor like a dog on a collar and leash and lap pee out of a dog bowl. It’s ok to enjoy having electric current jolt through your balls until you’re screaming and pain and red faced. It’s ok to go to work in lace panties (like I’m wearing right now). It’s ok that my only tattoo was ordered by my mistress. So I’m proud that I’m good with being a slave, a sub, a masochist and a sissy. It’s what I am and there’s nothing wrong with it. It takes some courage to get there.