Here's what I heard:

TK's original moniker was BB for Bubba's B*tch.
Bubba, being a trustee, made early parole. Ever since then the moniker has been TK for Trustee's Kid. There's a long waiting list to become a trustee as the main perk is to be in the TK rotation. They say he is very good at keeping the trustee's satisfied and very much enjoys being passed around. For 16 years now he's been "counceled" in this fashion and he's best known for the "Monkey Humping" sessions. Prior to being sentenced he had a long term sole source contract with the navy under their Don't Ask Don't Tell policy.