Websense (depending on the license your school district has purchased) is an enterprise level Internet filtration system. In most scenarios, it's deployed district-wide, not just at one particular school, or so it is in our case. I would highly advise against abusing your school or school district's Acceptable Use Policy (AUP) as your Internet activities are still being logged and reported whether or not you're being filtered. Staff and faculty computers are also being logged, even though they may not carry any Internet restrictions.
As I mentioned, Websense is deployed district-wide for schools. The way this is made possible is by routing all network traffic through their Websense service and whatever other firewalls and security systems might be in place. You'll have a very difficult time explaining to professionally trained (and sometimes unprofessionally trained) IT personnel and your principal if they find themselves with nothing else better to do than to look through the logs and see who's been where. Additionally, other deployment solutions such as Altiris (another remote administration software we deploy) help to enable a system or network administrator in tracking one or more user's activities across multiple computers and physical locations (e.g. the same student using the same proxy sites in the Library, Computer Lab, Lounge, etc to access the same filtered sites of the same nature).
After that, there's very little to prevent them from pulling up your name in a student database software, (e.g. Schoolmaster) along with your mommy and daddy's contact information, giving daddy a call at work to tell of Jr.'s unacceptable behavior. Little Jr. then comes home after a weary day of doing victory dances for all the little network filtration circumventions he's done in the past couple of hours to find a thick, long leather belt in his daddy's hands ready to receive his due reward at the end of the day. Oh, and probably a side of crackers and salt water for dinner.
Personal recommendation from experience? As an IT employee, I'd really encourage you not to do what you're doing. Believe me, I've been there as a high schooler and now work for the school district that I tried to get around for months on end. Generally speaking, if an enterprise level network management or filtration software like Websense is put in place, your district's invested a good chunk of money to license it for every workstation in your district - it would be highly unlikely they wouldn't make it worth their while by having already considered and integrated multiple ways of seeing who's getting around their costly software.
Hope that makes some Web-sense ;-)
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