No

“No! No please Principal Augustine, I’m sorry, I’ll be good! I’ll do whatever you ask from me Principal Augustine!” You beg out, clearly afraid to go too far down the punishment rabbit hole.

After a second of thinking, she pets your head. “Tsk tsk, what kind of Principal would I be if I didn’t give the proper punishments for misdeeds? But I’ll take that promise to be a good student, or you’ll receive even more. Now what do you say? ”

“Yes, Principal Augustine. Thank you.” You say reluctantly.

“But we still need to finish what we were doing before we get to your punishment...”

She takes the hook and lifts your skirt. Pulling down your panties as much as your spread legs allow, she is clearly suprised by what you were hiding. “My my... you really are a suprise Samantha, though I guess you saying Sam was a hint.”

You blush as you are figured out, hoping that this won’t turn her off.

“Now now, there is no need to be embarrassed, it just means a slight change in my plans for you. But first, where were we? Ah yes!”

She roughly inserts the hook into your virgin ass, with no lube or warning. The bulbous head takes a second before it goes in with an audible pop, matching your moan of pain and pleasure. The rope taughtly connects the hook in your ass to the collar on your neck, chocking you slightly as it firmly holds the hook in place.

“Now what do you say Samantha?”

“Th...thank you Principal Augustine!” You moan as the intruding hook rubs against your prostate with every slight move you make. The entire situation has you as hard as you’ve ever been, but you are careful not to move even if all you want to do is hump the desk you are tied to.

“Now” Principal Augustine begins, “what punishment does a cute little trap like you deserve?”