Hint: Please DO NOT start with 5" heels. your calves will quickly tell you of your error. Start with maybe a 1 inch heel so that you start to slowly stretch the calf. Add a half inch about every 6 months of wear of at least 60 hours per that period. Also some of us will never master those stilettos. It took me 4 years to really master those things.
Want a challenge?
Try walking on soft earth with/without grass in high heels. If you tend to walk with your heels (long steps do that) they will quickly sink into the ground. take shorter, more lady like steps, and keep most of your weight on your toes.
HINT: if you are going to wear hose, do NOT use any nail polish with a rough surface. i.e. large glitter chunks. They can and normally will put holes and runs in your hose.