I am a senor in highschool and have been working to penetrate my schools firewall repeatedly but now the game has changed because they have a software on the server itself that filters all web request that they do not approve before hand. If i was you, don't install shit on that computer. For skype, go to your skype installation on your pc at home and copy the phone folder onto your USB. You should be able to actually open skype and login although im not sure because if they have the shit i do at my school now then theres really few ways you can get around the firewall which will block you from connecting to anyone else. I would recommend doing this with all your programs.
Go to
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to see if you can find anyone to your interest that should run.
As for booting from a live disk, there is a chance that it won't work either for getting around school internet restrictions. Some schools have the restrictions on the server itself which processes all the web request that is within the campus.
I use to use Hotspot Shield and Tor. Both worked up until they blocked the connections. Hope this sheds some light on your delima. Good luck and don't get caught.
- Leroy