I think the OB hits the rail only once.
The direct kiss-back shot is on the Jacksonville Project video, and there is only one rail contact. One clip of this is at
http://www.sfbilliards.com/articles/2005-02.pdf -- it is surprising how far the object ball sinks into the cushion.
Maybe with a large cue ball it would be possible to get the object ball into the cushion twice, but I doubt it. For a full-on frozen ball hit, the cue ball would hit the object ball and drive it into the cushion. The cue ball would continue forward slightly since it is heavier than the object ball and doesn't stop completely. The object ball would finish sinking into the cushion, reverse direction, and hit the cue ball a second time. But the object ball would still be in the cushion because the cue ball would have advanced, "encroaching" the object ball's space.
For a light cue ball, the cue ball will bounce back from the object ball some and so will be clear of the object ball when the object ball leaves the cushion.