I'm trying to imagine my perfect spanking game and I think I'd like one where rather than having fully predetermined scenes at specific points in the story you would accumulate misdeeds through your actions, so for example stealing something is one infraction, lying to another character is another, and so on. Different types have a different severity and your total punishment accumulates. If you get caught by someone you could try to talk your way out of it or plead for a less severe punishment, which might also end up making things worse for you depending on the misdeeds committed, whether it's your first time, the relationship between you and the person confronting you, what they know about what you've done wrong, etc. Rather than any random character spanking you, they would maybe have your guardian or girlfriend pick you up and take care of you. If you have no one, or you're a repeat offender, perhaps you would be sent off to something like a workhouse where more severe punishments are common.
The game would be an open world affair with you being able to work on either solving quests that you can tackle either through socially acceptable means or "illicit" ways or go off doing various other activities. Maybe the latter could mean things like becoming a freelance thief breaking into buildings at night or working at, say, an inn where you can get in trouble if you mess up or are lazy. If you play well you could get by never getting caught or characters being more forgiving since you're well-behaved usually. Maybe they could become aware of crimes without knowing that it was you who committed it but once they find out that you are the master thief that has been hitting the local shops you would be in for a severe, possibly public punishment.
