The trash-cli version shipped with ubuntu is quite old. 
In the current upstream version it doesn't crash but simply print an error:

    $ trash-put --version
    trash-put 0.2.1
    $ sudo mount test-volume.img ./test-volume -o loop
    $ sudo mkdir ./test-volume/.Trash-1000/
    $ sudo chmod a-r ./test-volume/.Trash-1000/
    $ trash-put ./test-volume/foo 
    trash: cannot trash `./test-volume/foo': [Errno 13] Permission denied: 
'/home/andrea/Desktop/bug-ubuntu-340277/test-volume/.Trash-1000/info'

I'm hope that the new version could be early packaged in Ubuntu, in the
meantime you can install the upstream version with these commands:

   sudo apt-get install python-setuptools
   sudo easy_install trash-cli

As far I know the trashcan spec does NOT says that "the home trash
directory SHALL be used as fallback" but they say that it COULD be used
and the choice is up to the implementation. I personally thinks that
using it a fallback is not a good idea, but if many users want this I
could add this features. If you want this feature fill a bug in
http://code.google.com/p/trash-cli/issues page.

-- 
trash fails on filesystem whose mount point isn't writable
https://bugs.launchpad.net/bugs/340277
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