Despite increasing pop culture coverage, anal sex is still heavily stigmatized. While this might be true for some women, assuming it goes for all women is completely unfair. Woman A: It honestly does hurt, be prepared, and use lots of lube if you want an easier time. Woman B: At times, it can be uncomfortable, but I don't recall that it ever really hurt. I've had partners who are very attentive and listen to my needs, so I've never experienced pain. There are times, however, when a larger penis may cause cramping.