When a man’s glans hits his hymen, he normally does not feel pain under normal circumstances. The first thing to know is that although the thinness of a woman’s hymen may vary from person to person, most women’s hymens are still very thin, so when the male penis is inserted, the hymen is not felt to break. In the case of a relatively thick hymen, men may generally feel a hindering sensation in the glans area during penetration, which will disappear with the rupture of the hymen, but will not be painful either. Overall, men and women usually do not feel the pain that the hymen brings to the penis when they have sex for the first time.