Bart petitioned me with a session where I unmercifully cane his ass while he is being slowly drained by my Venus 2000 Milking machine. You can't really see the machine because Bart is lying on it, but you can hear the pumping noise it makes and you can tell he is humping something while I thrash his ass with great gusto.

I start out with my thick leather belt, and then the cane, and then a multi cane implement that really packs a wallop. Bart finally climaxes at the end, experiencing the ultimate mixture of pleasure/pain at the same time. You too can experience this session in my d... Show more