Begin by washing your hands, and make sure your new jewelry and taper are clean and ready. Massage some of your lubricant into your ears, and begin to push your taper (small end first!) through one ear. Pay attention to how your ear feels! If you encounter any type of pain or strong resistance, stop immediately..
To properly stretch your ears, you should first determine what size you are currently at. Never ever skip sizes! Skipping sizes can result in extreme painful stretching, including piercing blowouts and infections. Jewelry sizes are typically referred to in gauges ranging from 22GA to 00GA, with 00GA being the largest, and 22GA being the smallest.