Closestedge's sissy is put through the paces in this rigorous anal training session. After popping his anal cherry with a monstrous dildo, the sissy is taught to take it like a slut, pleasing his master with every thrust. With each deep penetration, the sissy's moans grow louder, his body trembling with a mix of pain and pleasure. Finally, after taking his training like a champ, Closestedge rewards him with a hot, sticky load of real cum, dripping down the sissy's face in a humiliating, yet satisfying finale.