A: I am assuming you are pregnant or have a newborn. When you are first starting out, it may take a few hands to make this work. You can lift your breast up if it is pendulous and position your nipple so the baby doesn't have to work too hard to find it with his mouth. With your other hand (or your partner's) hold the baby's head and support his body in a semi-reclined position near your nipple. Ideally, the baby's mouth should be wide open so he can take a significant portion of the pigmented area and not just the nipple. If he needs coaxing to begin suckling, gently stroke his cheek with your finger or your partner's finger.
If you are just starting to nurse, you may feel a momentary discomfort on the initial latch. But, in general, if it hurts or hurts for a prolonged period of time, it isn't a good latch and you will need to reposition. There are several positions you can try, but I would suggest getting the "Brest Friend" pillow to make nursing more comfortable and support the baby's weight. It does no one any good to be in pain while nursing--as it will only get worse and make the experience very unpleasant. It's best to seek help from a certified lactation consultant.