Connecting one 2D shape to another 2D shape at two points at once using the user interface only is not possible AFAIK.
You can connect 1D to 2D at two points at once though (check out the built-in "rack" shape as an example), but not 2D to 2D (why, btw?)
You can also connect one 2D shape to another 2D shape at one point (the connection point they have should have inbound/outbound for this to work, by default they are inbound)
We could discuss workarounds, though, if you could provide a bit more information regarding the shape you are trying to build.
Is there a specific reason you exclude grouping from the consideration? Or, maybe you are just not sure how to use it to build a shape like this?
Would something like a container+list work? (check the "Database" built-in diagram template for example)