Hey dollar,
Sounds like I'm you're man. I work in a school on the content filter doing things just like that.
If you're in a large school, it may be worth looking at a large content filter appliance like the one we use called ContentKeeper, it is an Australian product (I'm in Australia). But we use it and I believe they have some overseas dealers too. It is a very powerful product though.
If you want something cheaper, look at a product called AB Tutor, we use this for remote connections to provide support to staff, and also remote logins to update/troubleshoot/install software. But it also has the fuctionality to block words from being searched, or alert you when done so. And will log it and screenshot it for you, give it a date and username in the screenshot.
Content Keeper does search filtering, you can add the word "pr0n" or "warez" to a list, and apply that to any search engine you wish. When they search "warez" in Google, it will give them a blocked screen.
I just saw this today as well, a set up guide on Makeuseof.com with some proxy software allowing you to control what users see.
http://www.makeuseof.com/tag/c.....-part-one/
Give that one a try as it's open source!