I have no clue how to find lupa. Am I supposed to go to the question mark? Because it keeps giving me the normal werewolves.

Lupa as normal encounter is marked as Werewolf Blonde, and you can only have it in the 4th location (4th map of a game).

Lupa as a hired girl and participing in the Madame punishments is available in Brothel after finishing the Brothel Madame quests

Yeah, also, if you still see question marks, you probably have to let Werewolves fuck your ass/make Trudy do this.

Talk to Brothel Madame for odd jobs to get hints