I have, when I was a contractor for a major silicon valley tech firm, the VPN connection meant everything went through the VPN, and no way to disable it (Cisco VPN software). No access to the LAN, printers, etc., and all your traffic through the VPN, as evidenced by the location-aware advertisements on the web changing to $CLIENT_LOCATION instead of $HOME.
BTW, if you have a VPN like that, disable all your network drives, or Explorer will slow down to a crawl. Took us quite a while to figure it out...
Sure, we weren't filtered, because there was no internet to be filtered when we (most of us, at least) where growing up. I was born in the mid-70's, my parents had to worry about me somehow getting my hands on a skin mag or betamax video (both of them non-easy propositions), whereas these days there's more porn you can shake your stick at just a click away on the internet.
Other than the nitpick (this is slashdot, after all), I fully agree on education. I intend to educate my children - I don't want them to go learn by themselves like I did, my parents told me exactly jack shit.
And I will hammer the topics safe sex and birth control like crazy, the horrors of STDs and unwanted pregnancy. I have toyed with the idea of keeping tabs on how much I've been spending on my son to present him a complete report when he gets to sexually active age: "Son, this is how much not stopping for a condom can cost - bear in mind we had good jobs when we had you, how much do *you* make nowadays?".
Despite all appearances, your boss is a thinking, feeling, human being.