I didnt find a way to trigger dragging manually, but I have found a workaround for my similar situation.
I had this situation with two overlapping images (see image below), both partially transparent. In draggable's start(event) I wanted to check if it hits transparent pixels. If so, I looked under it for another element to see if that one was hit. And if it was, I wanted to initiate its dragging.
Solution? I reorder images on mousemove, and draggable is then triggered for that topmost image.
For pixel-precise element selection, see my another answer in: registering clicks on an element that is under another element