Pickpocketing is the second ability under the Nasty Deeds category. It allows you to steal items from merchants and other NPCs. To pickpocket anyone you need at least 1 point in the ability. Higher level targets will require a higher skill in pickpocketing. Any one target can only be pickpocketed from ONCE during the entire game. If, however, you check his inventory and decide to steal nothing, you can come back to pickpocket him later. Even after pickpocketing your target, you will be able to target him again with another character, provided they have a high enough Pickpocketing skill.