What will breastfeeding feel like?

Not Painful. As a mother of two who breastfed both of my children, i can tell you that the first few days are an adjustment period. The key to remember is that it should not hurt. The initial latching on may be uncomfortable but once the let down happens it not painful. To learn more about breastfeeding try reading: the womanly art of breastfeeding.
Ask a mom who has. As a male, i don't feel qualified to answer this question. Your best bet is to talk to a mothe who has breastfed her children and get her report. You can find mothers willing to share through la leche leauge international. Visit their website and see if there is a group near to you. Even if there is not you can talk on the phone to a mother who has breastfed her children.