I've found 2 ways to make it work.
1. Your-Freedom + SocksCap
2. Putty, OpenSSH + SocksCap.
The second alternative is more stable and secure. I run a SSH server at home and connect to it from school and I think that it's more "disguised" for the administrators as I think they log all traffic and could easily see those who are communicating with Y-F servers.
Followed a nice guide (google for "surf at work") and got it up and running on my first attempt.
And don't forget to study.