We all know that VB\'s Nothing is similar, but not equivalent, to C#\'s null. (If you are not aware of that, have a look at this answer first.)
The first answer I gave missed some points, but this should do it:
Dim o As Object = If(myBool, 5, DirectCast(Nullable.GetUnderlyingType(GetType(Integer)), Object))
This uses the fact that Nullable.GetUnderlyingType will return a null reference if you pass it a type which isn't a nullable value type - which Integer isn't. Other alternatives exist, such as Type.GetElementType(), or perhaps GetType(Object).BaseType.
I've checked that this works with multiple different types for the second operand.
It's slightly annoying that you have to cast to Object... I'm still working on alternatives for that...