The hardware is fairly simple, do a google search on hot plug.
The problem you will face is the software. Detecting the presence/absence of these devices. An interrupt driven device must be made so on both sides of the plug that an interrupt is not generated when (un)plugging. Another issue is (un)plugging during data transfer. Of course you may want to generate an interrupt when the device is plugged in, that interrupt will come typically when half the pins are connected; it is easy to determine the debounce time for a switch, what is the debounce time for a human inserting a plug and hearing the phone ring.

Yes, it can be done - absolutely. Just make sure the application is worth the effort.

Have fun,

Erik