This is an extension we have applied to test multiple (physical) devices (we do it in iOS) in a single Calabash test. You do this by adding to the calabash command line these variables:

DEVICE_ENDPOINT_1=192.168.13.1:3333
DEVICE_ENDPOINT_2=192.168.13.1:3334

And then you can extend your test by writing:

Then on device 1 do:
    Then I see „No connected device"
Then on device 2 do:
    Then touch „connect"
    Then wait 3 seconds
Then on device 1 do:
    Then I see „Device has connected"

Hint: Instead of the command line variable DEVICE_ENDPOINT_1 you can also choose a more descriptive name (e.g. „DEVICE_ENDPOINT_IPAD") and write this name then also in the test („Then on device IPAD do:").