More or less... Bob made great progress by giving Lucy dresses. It's not exactly torture! haha. At one point in the living room, Lucy is drunk and he puts a necklace on her, and they're very close. Bob kisses the back of her neck, which she apparently likes, but she quickly returns to normal and runs away.
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I know many people like BBS because of the rape and psychological violence, etc., but I find it more interesting that the player can choose how he'll corrupt them. And of course, it doesn't have to be a straightforward path... sometimes he'll take advantage of an intimate moment, sometimes he'll use blackmail, sometimes punishment, sometimes gifts... it's more interesting that way.