Keep context menu after user clicks on button?

I also asked this question here in the Chrome Chrome group.

I would like to be able to keep the context menu open even after the user checks or unchecks the box. My plugin allows users to check which devices they are using when testing and when testing multiple devices, it is inconvenient to open the context menu multiple times to mark each device.

Does anyone know how to do this? It doesn't seem to be supported. I really don't want to use any magic to reopen the menu, if possible, after the user has checked the given device, hence the question here. If this is the best (but hacky) way, then it is fair. I hope not! I think the menu flickering will look bad too.