Before this shoot, 22-year-old straight boy John had never done any adult work or been touched by a man. He certainly won't be able to say that any more.
This video opens with Tom giving John 64 hard, bare-handed smacks, all on his right ass cheek. John's ass is already tender, and the pain is written all over his face as he struggles to maintain his composure. After the hand, Tom tells John to go choose the implement he thinks will hurt least. John chooses poorly and brings Tom a large flog. He realizes his mistake with the first lash of the flog. It quickly has him kicking his legs and crying out in pain.