go SLOW with the stretching. with the smaller gauges [18-12 gauge], you can pretty much buy a captive ring or a normal earring and just slip it in. make sure your ear heals COMPLETLEY before going to the next size.
don't use tapers, you'll just end up with blowouts
the best way to stretch your ears is to wrap electrical tape around your jewellry. Plugs work best. Wrap 1 layer of tape a week around it. Don't stretch more than 2g/month. You want to go very slow. Or this will happen.