In The Elder Scrolls V: Skyrim for the PC, PS3, and Xbox 360, pickpocketing is one of the easiest skills to level up, and can be very lucrative.
Level Pickpocketing With Skill Trainers
A very fast trick to leveling up pick pocketing fast is by spending money on skill skyrim trainers, and then pickpocketing the money back. Any time you spend money on a skill trainer, the money they take from you goes directly into their inventory, which means it can be stolen back. Stealing large amounts of gold gives you a large amount experience for the skill as well, making this process very fast for leveling pickpocketing in skyrim.
Level Skyrim Pickpocketing With Pots and Baskets?
Another great way is to pick up pots or baskets and put them onto the heads of all of the nearby npc’s so you can pickpocket cheat skyrim successfully. To pick up items, you simply hold the button that you would normaly press to take the item.
Level Pickpocketing By Stealing Expensive Items
If you want a less cheating feel, then look into random npc’s pockets until you find rings or amulets worth decent amounts of gold (opening an npc’s pockets isn’t a crime). The higher the value, the more skill you get for successful skyrim fast pickpocket. Follow that npc around until they are alone in order to successfully pickpocket them, or simply find their house and break in at night to skyrim pickpocket them as they are at sleep.