How to select multiple items from contextMenuStrip

I'm working on a C# winForm project that use a contextMenuStrip. I'm trying to figure out how to disable/override default behavior of allowing only one toolStripMenuItem at a time for selection. I've been working at this for the last 2 days and I'm making 0 progress.
 
Does anyone know of any links or how to do this?
 
Thanks in advance, -DA

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dee allen