Abstract: A document sending device or system is described wherein the message bearing document contains specific locations for placing information regarding at least first and second addressees. A document container or envelope receives the message bearing document and it has at least first and second windows formed respectively in opposite sides and the windows are in registration one with the other. The locations of the address information on the document are such that with proper orientation and reorientation of the document each one of the address information locations will register with one or the other of the windows in the document container. The document sending device can also be used in conjunction with diverse forms of shipping containers, packages and the like to facilitate movement among multiple addressees.