Ok for anyone who hasn't beat this game, like I did on my 3rd play through this is how you can do it.
Move her arm first, then wait for sleep gauge to go up then removed skirt.
Then rub her nipple almost to a nipple stand, and rub her to almost wet panties.
Do both to get to red aka one right after each other, buy sleep pills, use them and rub her wet panties, and done.
THIS is to help everyone who hasn't beat this yet.