Hmm, I've never heard of this. I know you can pickpocket your gold back from trainers. Extremely helpful for raising skills at no cost. At least check him and see how much gold he has now. Depeneding on how much gold you take and how high your pickpocket level is dictates the percentage of chance to steal the gold back. I have a high pickpocket level so it's ususally easy to get gold back from trainers. You can speak to a trainer in pickpocket to raise your skill then steal your gold back. Everytime you steal your gold back it usually raises your skillanother level. If the trainer didn't want that to happen she shouldn't have been training to pickpocket then, lol. The trainer I went to was a woman begger in Windhelm.
What's your level in speech at the moment?