If she's awake, the night-crawling scene will cause her mood to drop by at least one level.
To have her look "pleased" requires her "Bad" meter to be at or near zero, and she requires at least one orgasm. For the Ahego, you have to bonk her all night long, where Onii-san goes "damn, I really need to get to sleep" and give her at least 12 orgasms.
If you want to see her mad, end the scene just before you make her cum.
That's pretty much it. The rest depends on her trust, sexual interest, and maybe sensitivity level.
Off topic, but I found another "bad end" for the game. Imouto can get up and leave, asking Mom to have her live on campus in the dormitory. This happens when her trust goes below 0, which is a particular risk for the "bum" occupation, as every time Imouto has to buy a meal, her trust drops 3-5 points, and at the start of the game, that's a loss that's hard to afford.