How to create a context menu with submenus that will insert text

What's the best way to create a context menu that can be triggered by a keyboard shortcut, that displays a menu (with submenus) such that selecting an item inserts or pastes the name of the element?

I'm trying to organise access to about 50 text items, so I'm thinking that seven menus each of which links to seven or eight subitems might work.