Either pay 20+10GP pay 20 and have Charisma 4 or satisfy him with rank 3 of needed skill. How to start: enter the Town Square at daytime in Silajam and listen to the towncryer. Take the white door, others may also “reward” you. Now you can explore rooms in the Brothel. Reward is 100GP, a new girl to hire and a scene.
Again, only the type of enemies that spawns around towns will count. Ask her about jobs, and then get knotted anally from an ordinary Wereslut (or make Trudy fight her).Either choose to wait and read the diary, or beat the Warlock and re-enter the Manor. Or make Trudy take care of it (make sure to not fail stealth check). Travel to the Town of Monsters, enter the tavern (Pub) and take a carriage back to Silajam.
What to do: keep in mind that requirements for stages 2, 3 and 4 can be completed before you get the task itself. Choose your bonus reward - either 50GP or something else. How to start: talk to the Brothel Madame.
