creating glass in CSS?

I would like to know how to create glass also but not the normal glass, but the type of glasss that makes holes when you shoot it and breaks apart when you run trough it
 
In HL2 this is done by creating a brush and covering it in NODRAW textures, then the 'inside' of the window only you cover in a glass texture. Tie the window to the 'func_breakable_surf' entity and fiddle with the properties, then place an 'env_cubemap' outside it. I imagine its a similar process in CSS
 
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