OSX Mavericks Trash Question
I am really not sure what your setup is, so my answer is pure guessing.

So it happened before when I was using ParagonNTFS to delete some files from NTFS filesystem. What you need to do is boot into your Windows (BootCamp), use its built-in partition repair tool to repair the partition. Then uninstall ParagonNTFS because it will damage your NTFS partition!