I'm wondering if there's a special trick to leveling up pickpocketing? I try to pickpocket every bandit I can and I usually avoid doing so in open cities because everyone gets all pissed.

I'm not (necessarily) looking for an exploit, but there has to be a better way than gaining a couple levels every couple of hours.

I don't know of any special tricks when it comes to doing the actual deed, but there is at least one NPC who will train you: Silda the beggar lady in Windhelm. You may have to give her a gold piece first before she'll offer to train you, I can't remember. There are probably other trainers but I can't recall exactly who, Silda I know for sure does it.

Vipr in the Thieves Guild trains as well, but that doesn't always help.

Mine went up pretty quickly once I focused on it (I only wanted it for Misdirection and Perfect Touch - I don't make a living with it.). I just used Trainers every level and used the Shadow Stone and Pickpocketed NPCs that I dislike and Reverse Pickpocketed better weapons onto NPCs I like. I also had 4 pieces of gear with Fortify Pickpocket on me; I know it didn't make me level faster, but I could PP and Rev PP more expensive items and I think that does help level more quickly.

Wear Fortify Pickpocket enchanted items to boost success rate.

Successfully pickpocketing more expensive/heavier items give you more experience.

Don't get caught. It's annoying. Save before pickpocketing and reload if you get caught.

Or perhaps reloading takes long time for you if you play on Xbox or PS3.

Doesn't take anylonger on 360. I did alot of reverse pp/ training in pickpocketing, the one skill I did alot of training in. I tend to save before and after jobs and before any pp attempt.

I've never really picked a pocket..