pass argument to __enter__

No. You can't. You pass arguments to __init__().

class ClippyRunner:
    def __init__(self, *args):
       self._args = args

    def __enter__(self):
       # Do something with args
       print(self._args)


with ClippyRunner(args) as something:
    # work with "something"
    pass

Yes, you can get the effect by adding a little more code.

    #!/usr/bin/env python

    class Clippy_Runner( dict ):
        def __init__( self ):
            pass
        def __call__( self, **kwargs ):
            self.update( kwargs )
            return self
        def __enter__( self ):
            return self
        def __exit__( self, exc_type, exc_val, exc_tb ):
            self.clear()

    clippy_runner = Clippy_Runner()

    print clippy_runner.get('verbose')     # Outputs None
    with clippy_runner(verbose=True):
        print clippy_runner.get('verbose') # Outputs True
    print clippy_runner.get('verbose')     # Outputs None