Hi!
I have recently been at a loss at how I can start to have masculine/feminine stuff with Mom and Dad. It always says my Femininity is too high or too low :(
So, if you are going for femininity you need to have at least 5 femininity then it will trigger a small side thing you have to do when you are in the house where your mother has you try on underwear. You have to go through this sequence all the way until you have a run in with your dad's co-worker and then confront him about it. This sequence should be in your Objectives page.
For masculine stuff, you just need to be further than -5 femininity and you will just have repeatable interactions with the parents that build relation with them.