How can I improve my pickpocketing?
Join the thieves guild and either level up pickpocketing from one of the guys there or go around pick pocketing the members of the guild. They won't try to fight you and it leveled me up from 20 to 50 within minutes.
I used to level pickpocket, sneak, and speech at the same by trying to steal from guards. Just sneak behind them for a bit, then pickpocket an easy item and repeat until you get caught. Now just opt to persuade them. Once your speech is high enough to persuade, you will be able to do this exactly once for each guard. They will however remember you and arrest you when you try to steal again from that exact guard.
Also if you're heavily into pickpocket, I'd recommend a mod to increase the maximum chance to 100%. In the vanilla state, Skyrim caps the maximum chance at 95%, which will leave you getting into problems regularly even as a pickpocketing master. There are plenty of mods available to achieve this, I'd recommend this one: Pickpocketing Chance Caps, as it does just that and nothing else.
I gained 50 pick pocketing levels in half a day by doing this:
Only works on guards... also you have to gain some king of respect that applies to the area your in. For example, pick pocketing in Riften using this method means first joining the thieves guild. For me, everywhere else was fine because I've completed the Stormcloak quest first. Basically, you can't get away with bribing thievery unless your a local "someone" to the guard.
Steal everything they have that's easy enough, like 90%, if your lucky enough not to get caught, re-place it on them, and anything else you stole and don't care about. Keep giving and taking items until your caught.
When they catch you bribe them.. In my experience, they all demand 420 septims (ish), except for the Riften area, where it's only 12 septims. When this happens, wait for "HIDDEN" to appear and take back the money you bribed.
I've never been caught taking back the money... DO NOT carry on taking items after this. If your caught after bribing there's no option to bribe again. Only hit each guard once, I THINK after a period of time you might be able to hit the guard again.. Do so at your own risk, and by period of time I mean at least a few days.
I did this to all guards in Markarth, Whiterun, Riften, and a couple of other places. Meanwhile, pickpocket every civilian, but only take things like money, lock picks or arrows, seriously. After a pick or 2 I'd stop, they seem to catch me even with 100 PP, and there's never a bribe option. If a guard is near by and says "stop!" then the fight stops. Attacking the civilian is a bad idea, and the guard is only handy if you can bribe them.
Hope this helps!!!