So why didn't he started begging, pleading for mercy, for redemption, and be humble? Even he was lying. She wouldn't know that. Redeem myself in the eyes of those girls whose feelings I hurt. I mean, that's his best chance because, bro, once you're able to fit inside her school loafer and you can't get out. You need to get on your damn four legs, put your head on the ground and beg. Because if he didn't, well, we see the outcome right now.
Honestly, this would have been a better, "How does it feel" hard lesson. But if you want to go to dark route you should have just kept them as a slave. Now to do what is your imagination.