If your a first timer yes
Depends, it didnt hurt at all for me the first time
Going to depend on you. For me, my first time was more uncomfortable (at first) than painful. Yes, there was slight pain, but not enough to detour me and as I further relaxed into it, it felt great. After the first couple times? Nah, not at all.
Other women have different experiences on their first time, however. So, it really will depend upon a mixture of your body, how much you trust your partner, how comfortable you are with him, if you're relaxed/into it, if if he's going to take care of you and give you a fair amount of foreplay and be gentle, etc.
For me it doesn't hurt at all but of course my first time did. Second was better