Yes it can even if it's more likely to happen if your own lubrication starts to dry up. But any prolonged penetration will put some stress and tear on the tissues even if there is slip in between.
To make matters even more complicated it's a multiple factor system where at least your own lubrication (more slip = less chance for pain), his size (more, especially girth = more chance for pain), what part of your montly cycle you're in (just before bleeding = more chance for pain, at least for me), general state of your system (dry skin, recent previous sex = more chance for pain) and then probably a few more.
