Earlobe stretching.. How long does it take?

I've been having the worst time with my normal earrings and now I want gauges. I know I need to move down to a 16 gauge, and I've been looking at different sites about it... will there be any serious pain with the stretching or will it be a slight pinch? Also, the gauge tapers I was looking at were very long, can you or are you supposed to remove them when you're sleeping? And how do you keep them in your ear during the day? Can basic 16 gauge earrings be worn instead of using the taper?