1/2 an Inch to 9/16ths Stretch

Hey! So, I just bought some lovely wooden tapers for my ears (they're pretty lightweight, too). I plan on wearing just the tapers and MAYBE I'll get plugs, but idk. 
Just a few questions for those who have stretched ears:
1. Will wearing these tapers fuck up my ears? 
2. How long should I wait to stretch them from 1/2 an inch to 9/16ths? 
Thanks!