We had one person do the following -
Generate a pdf, about 400 pages.
Print said pdf, single sided.
Put each page in a fax machine, fax to ???
Remove page from fax machine, at least she put the pages in the secure waste bin.
Can you imagine how long that takes? She did it more than once.
We're using MoveIt, we got it for moving files around but it also has a plug in to Outlook. It takes the attachment and stores it on a server in our DMZ, and sends the recipient a link to retrieve the file. I don't use it myself, so I'm not sure what mechanism keeps that secure so that only the intended receiver can retrieve the file, but I'm sure their sales guys can tell you.
https://www.ipswitch.com/moveit/ad-hoc