It shouldn't ever hurt when you stretch up if you do it right. None of mine did besides my first couple because I didn't really know what i was doing originally.
Remember to always use lube and play with/massage/gently stretch out your ears before your actually stretch for an hour or so. All after waiting at very least 3 weeks (but depending on how your ears are they may want a little longer time). If you destroyed your ears and caused alot of scar tissue to build up should wait much longer.
I spent a little over two years getting to 7/8" (taped all the way from 00g to 7/8").