Yes, I've played several kender, all with the same DM who loved playing kender as much as I did.
Whenever he ran a campaign with any kender in it, he would roll the pick pockets but never tell me (or whoever else was playing the kender) what they got til the kender actually sorted out the pockets. To be honest, it just made more sense that way since they end up with all sort of weird stuff in their pockets, most of which tends to be unintentional.
Klaatu