Should getting fingered hurt?

Sorry for the awkward question lmao. But anyways my boyfriend and I have been going out only for 2 weeks now and he's been saying that he really wants to finger me. I'm not apposed to it at all its just that when ever I masturbate it hurts if I use more than 1 finger and I'm kind of worried the same thing will happen if he tries to go in with two fingers and he can only get one... That will also be really embarrassing and will most likely crush myself esteem.. Is it supposed to hurt?? Is this normal or am I just like incredibly tight? Please let me know if any of you had/are having this problem