Trash Privileges Issues

Hi. I use a MacBook 10.5.8, and I am getting this message,
"The operation cannot be completed because you do not have sufficient privileges for some of the items."
My permissions in Get Info are read and write. I have tried option + empty trash. I have been in Terminal using "sudo rm -Rf ~/.Trash/" but that didn't delete my trash. Any suggestions? I'm not a Terminal genius so bare with me.

I just also want to mention that this is happening when i have my usb drive plugged in. I am trying to delete files from it. I recently noticed that in order to actually delete files from my trash that I has placed from hard ware, I had to keep the hardware plugged in and select "Empty Securely" and then it would actually delete.

Thanx