Well, if she gets knocked up by Bobby, it'll be a bomb. This has not happened in the games.
Bobby is quite naughty and bold. I think that it is logical if at some points of time, Bobby tries to breed Anna (Mom) by cumming inside her when she is fertile. The first attempt will be a failure for sure. And of course he will try it again. How does our MC (Bobby) knows which girl is fertile? Bobby is very naughty and curious. He should find it out. And he can make a plan to do it. I will call it impregnation (action to impregnate) but not pregnancy. I would leave pregnancy for an end of the game story like The Incest Story 2 and other games.
Impregnation without pregnancy makes game very fun to play. Even dirty talk (or thoughts) relating to risky sex is very exciting.
Am I the only guy here think so?