Let’s try some more pain for him. Again, with the ruler, give him a few minutes of ball slapping, increasing the tempo and pressure, judging by his reaction. Also, give him a few slaps of your hand against his balls and cock head. Finally, take the clothes pegs, and place 20 on his balls.
Give his cock a few more strokes to make sure he is nice and hard; then take off the pegs. Surprisingly it is more painful when you take them on, that when you put them on. How fun!