It sounds like you're trying to achieve two separate goals here :
To implement the bosses suggestion you need a different system to handle each and a way to categorise the blocked sites - or a system that allows more fine grained control.
Stepping back a bit...
More importantly though, your boss should want to demonstrate that he trusts his employees to use their work time sensibly. By blocking websites for reasons other than network security and creating little bureaucratic procedures to unblock them you send a clear signal to the employee that they are not to be trusted with a basic resource like web browsing. Expect them to respond in kind.
Am I missing something here or is this question utterly ridiculous. It says, here is my encrypted buffer encrypted with an unknown "algorithm" which, for all we know could be an XOR with a one time pad that only he has?
You want us to evaluate your algorithm then give us the damn algorithm!
I have only questions
Why do you Americans put up with this awful service? Why is it legal for medical providers to behave in this way? Who is looking after the interests of the consumer to ensure they are not ripped off? Who is regulating the market so that it remains healthy allowing proper price discovery instead of the outright fraudulent practices that you have described? What do you pay your taxes for?
This puts America in an entirely new light for me. I am genuinely disgusted.
How about open wifi over Tor - that would allow you to share but avoid problems associated with liability for actions done on your connection and an ISP would have a job proving you were sharing their network capacity too.
All you need is a router that supports multiple SSID's and segmentation of them, a couple of clever firewall rules and Tor's Transparent Proxy support.
Except often it goes like this:
NEWB: I have . How do I solve it?
List doesn't reply within 10 minutes.
NEWB: Look, I have to have this fixed by Monday. How do I solve it? If you don't solve it for me then I have to move to
List doesn't reply within 10 minutes. NEWB gets angry
NEWB: Its such a simple issue. I can't belive nobody can solve it. (Oh the irony). Bump bump bump.
List: STFU NEWB.
Don't expect support-contract-like behaviour from a list - remember they're volunteers, there's no "SLA" and they don't work for you.
Some simple steps for success: Make the effort to properly describe your problem and the steps you took to try and solve it. Make doubley sure you're posting to the correct list - many projects have development and user lists. And always be polite.
"I have five dollars for each of you." -- Bernhard Goetz