Does't seem possible with Windows Terminal Service but *might* be possible with Citrix:
...Use the Shadow button to start shadowing one or more users...
Quoted from:
Viewing User Sessions with the Shadow Taskbar - Citrix eDocs
http://support.citrix.com/proddocs/topic/xenapp-w2k8-tp/ps-sessions-shad-us-shad-tsk-bar-v2.html
Google: simultaneous|multiple session|terminal|remote shadow
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