If you like going to Madam Lil's you can get one girl free as many times as you want! You have to have atleast 2 pickpocket points and do all the quests until you finish the quest when you have to get Cassie's Necklace. Once you get the necklace give it to Madam Lil. After that when ever you want a girl, pickpocket the necklace back and tell Madam Lil you got the necklace. You can try to get two girls by doing all the quests and pickpocketing the Amulet of Beauty(I don't know how much pickpocketing points you need). If you want to know where to get the Amulet of Beauty look it up in the quests.