I've just spent roughly an hour following Ahkari from Riften To Dawn star stopping her at random intervals seeing if she will teach me how to pickpocket, she did not. You can imagine how I'm feeling right now... Please tell me how I get her to teach me.

From UESP

Although the Official Game Guide lists Ahkari as an adept-level trainer for the Pickpocket skill, the game guide is incorrect. She does not actually provide any training.

Does anyone teach adept level pickpocket?

http://www.uesp.net/wiki/Skyrim:Trainers.