Insatiable desires game
So I have devised a little task to help build your confidence. As you could see from the list of clothes you will be going to a public place. The items your wearing are passbale as your own clothes. Hence why there is no skirt or heels sissy. Although the stuffed bra may be a little embarassing, I wonder how you will get around that one haha.
Your going to insert your buttplug when you get dressed. If you where lucky and rolled a low number then of course you can cover up with your boy clothes.
You can always wear a coat if it's cold.
You will need to replace your buttplug at some point. So either a place with public toilets or a semi-public place where you could switch it discreetley and safely.
I would suggest a park as that will be better fitted to this sissy challenge. I would suggest going to the park (or selcted destination b4 you read on) you will be more likley to follow through with the challenge. If you really have to know then continue. Make sure you are dressed up in your sissy clothes now and any other clothes (e.g coat) before you continue.