I cannot provide a complete solution, but you should be able to drag the tentacle, yes.  Then, use collisions to help ensure that it wraps properly.  As for the wrapping itself, you ought to be able to do that by using the drag function from different perspectives in the scene.  This isn't a step by step procedure and might not work as I am not familiar with the rigging of tentacles, but I thought I'd try to help out anyway.