Are you using Visual Studio 2008 or 2005? I'm running this same code in vs 2008 and it's working...
I ran this code in default.aspx
Dim lc As New LoadedFile("test.jpg", 1)
lc.addProperty("prop", "value", "type")
lc.addProperty("prop1", "value1", "type1")
Session("test") = lc
Ran this code in default.aspx and was able to access the file properties:
Dim lc As LoadedFile = CType(Session("test"), LoadedFile)