Ummm （￣へ￣）Isn't that something they BOTH should have known about already?

Or do the women of the current age not do THAT anymore?

no as in he didnt even watch the videos of the demonstration how to do THAT

Also, their modern day females are different. I just read the latest chapter, and her doctor said that females evolved to not have a hymen anymore like the "ancient females" had. So even if he did watch that video it would not have helped in that situation.