In this video I show an Open Guard Pass that I call the Pony Pass. This is an important transition that presents itself a lot throughout various positions but I feel this is one of the easiest ways to practice the movement.
After the demonstration of the technique I included some instruction on what a good training partner will do to produce the desired space for practice. Obviously, while rolling, this will be a much smaller window but the concept applies the same.
This is part of a passing sequence that I showed from DLR and while this does not appear to be that viable, when paired with the second pass, it happens a lot more than you would think.
As you get better at this movement you will not have to place your hands on the floor (and you really should avoid doing that after you master the weight transfer and pathway with your hips).