Suggest Treatment For Painful Intercourse

I've recently began a sexual relationship with a man similar in age to me but much less experienced as me. In general, his touch receptors seem to be overly sensitive on his whole body. It also seems to be a problem with the penetration portion of intercourse. During initial penetration of my vagina he experiences a great deal of discomfort or pain in his glans penis. So much so that he almost decides he can't take it and wants to stop. With encouragement I am able to get him to continue. Once he has penetrated me, he is fine and we proceed as normal and have no further issues. He has commented to me on more than one occasion that I am "really tight for someone who's had two children". He is also much larger in size than my last partner and have been sexually inactive for a good length of time. His sexual partners in the past were few in number and only one or two encounters with each so he's not a lot of experience. I just want to know if this initial sensitivity will decrease as we have more contact, thereby "toughen" up the glans. He has a lot of pre-ejaculate and I am very aroused and have naturally been lubricated myself. Should we add extra artificial lubricant too? Or is this something he should see a urologist about?