don't telnet to a port if you see an established connection through it. you want to telnet to a listening port. look into your messenger for "listen on port **** for transferring files" or something like that. if your buddy uses the same protocol (say yahoo, aol, etc) he will most probably listen on the same port as you are. telnet him on that port.
but! that is only to make sure he has port **** open, as you will most probably get a black blank shell (this would be the result of a successful raw connection to that port on the remote machine). try playing with [URL=http://www.tartarus.org/~simon/putty-snapshots/x86/putty.exe]putty.exe[/URL] , hope it might come in handy...