I have to say it was some time since I last finished the game and now tried out the extra last content after the ending. Might have missed something and remember things wrongly but it felt kinda weird that the two girls the MC can knock up are Erica + Judy, especially with Judy since at least to me it felt like the "main" girls were sort of Chloe, Hannah, Erica and maybe Melissa when it came to a sort of "serious" relationship while the others were mostly just doing it for fun.
Though the MC mostly just seemed to think with his D and not really care for anyone deeply and it seemed like Chloe by the end of it seemed to realize that she sort of didn't love MC as much and just wanted to have fun while Hannah + Erica + Melissa all loved the MC but in Hannah's case she had stepped back because of Chloe for a long time and was now sort of in a weird spot while Melissa had also loved the MC for a long time but because of their positions at work she had kept it hidden. Again it was more then half a year or something I believe since I played through it to the ending.
While in the first game everyone got knocked up and in the 2nd it was the magic daughter + mom duo and maybe the blonde which made sense with the daughter since she seemed like the MC's main fling in that game.