It may seem silly, but just telling me your previous advices helped a lot; for example, I was completly sure I couldn't advance anymore in the arachnophobia line, since I was already fucking Alice after killing the spider, BUT then I realized I had a second option after the HJ (usually I only selected On Top, but there's another option, doggy) I'm pretty sure it's been that, because even when the quest is not finished, next morning I had a new dialog line with Lisa regarding Peeping...Not Max private spanking of his sister but mom spanking Max in private, that is the one that you have 19 days left of and you need to stop paying for that so mom will see Max as an adult.
Mom told you to support the family and she would allow Max to spank sisters then Max can ask to spank them in private.
For mom to spank Max in private that was long before Max getting to spank his sisters.
Hopefully it will lead eventually to taking Alice with me to the doctor, and to have sex with Ann Thanks once more.