This week's book giveaway is in the OCPJP forum. We're giving away four copies of OCA/OCP Java SE 7 Programmer I & II Study Guide and have Kathy Sierra & Bert Bates on-line! See this thread for details.
I have never tried to do a file transfer over Telnet and I'm not sure it is possible but since Telnet is insecure I would never even consider using it. In fact I wold never consider using Telnet ever for anything.
If your remote machine is running OpenSSH then you can securely copy files using either 'scp' or 'sftp' .