Trash - issue when trying to empty

This is my first time posting a question but I am really stuck so any help would be greatly appreciated. I have tried to find a fix from previous discussions but no luck. I upgraded my OS to Maverick recently and have had a few issues since, one being I can't empty my trash. It has a pop up that says 'emptying the trash' but this just hangs. I tried to shut my laptop down but it won't because it is emptying the trash.

I did force quit, then shut it down. I have used the secure empty option. I have progressed a little and deleted one file (well thought I had becuase the trash shows empty, however when I try to delete the next file, the pop up box now things there are 2 files to be deleted. It seems like they are not being deleted properly but hovering in the background somewhere.

An added bonus (issue) is that when I eject my portable drive now it also does not eject properly

Would really appreicate any input and I hope I have explained the issue clearly (I have tried many things so my brain is getting a little frazled)