I believe you have to have completed the "Special Jobs" for the cities to bribe in the respective holds.

I wondered about that, I checked UESP but couldn't find anything that specified it. It just refers to being a TG member, not having done particular quests to get additional influence in the various cities and holds. Maybe the options get better after the special jobs for a city?
I only did the TG once and I honestly can't remember for sure if i bribed a guard before completing the City Influence quests, but I think the incident I referred to in my first reply was before doing them. I was really disappointed that it didn't clear my entire bounty.