Hi Hon,
I would like to say that as far as #7, go to Glamour Shots. The people there are friendly, and do not make fun of you.
For #9, I have gone into stores as a male and tried on boots. Most of the sales people do not care if they know you are serious about buying a pair. I have also gone dressed, and had no trouble.
For#16, I am no young girl, but I would like to try asking young girls to help me. I also had the experience of asking clerks to help.
For#4, I did not go to VS, but I did go to a large dept. store and asked the clerk for help.
For#19, I went into a restaurant, but it was Halloween, and asked if I could eat in drag. I told them I was to eat my meal in drag, get a receipt, and my girlfriend would pay for it. No problem.
For #23, I was IN HEAVEN! I tried to get the sales people to allow me to try on gowns while I was there. They didn't mind, but the manager was against it. It would hurt business if a customer saw me trying on a gown, and I had no place to do it. I went to David's and J.C. Penny's. I solved the problem and bought them through the catalog. I also got around it by going to a second hand store. I tried on the gowns in the fitting room and came out and asked for advise, help, etc. I LOVED IT!
For#25, the same as above.
I hope that I have given you some help. I had such a great time when I did all this. It was such fun.
You have made a choice of a mistress to lead you. If you follow these tasks, you should be ready to be a "lady"!