A Leather Flogger

Anko smirked at Naruto's reaction as she held a leather flogger in her hand. She slowly strolled towards him until she stood directly in front of the bound blond.

"W-What is that, Mistress?" Naruto asked, eyeing the toy worriedly.

"This is a flogger, gaki. I'm going to flog your sorry ass with it until it's red." Anko stated, swinging her flogger into the palm of her hand. "Now, enough talk. Let's begin your punishment."

Naruto watched in worry as Anko walked around and stood right behind his bound form. She eyed his naked ass before looking up at him while raising her flogger.

"Tell me something, gaki. You're 16, right?" Anko asked.

"Y-Yes, Mistress." Naruto answered, causing Anko to smile before going back to staring at his ass.

"Good." Anko said before raising her flogger up and swinging fast.

WHACK!!!

"Ahhj!" Naruto yelled at the strike to his ass and the sting from it.

"One." Anko said before raising her flogger and swung it again.

WHACK!!!

"AHHHHHH!" Naruto yelled, much louder than before due to the strike hitting the same spot.

"Two." Anko counted off again, much to Naruto's growing worry for his ass.

This continued for the next 15 minutes with Anko slowly raising her flogger and waiting before swinging it and hitting Naruto's ass every time, causing Naruto's yells to grow in volume from the **** of the strikes and from the increased stinging pain in his ass. It stung so bad, it actually felt like it was burning.

WHACK!!!

"AHHHHHHH!!!" Naruto yelled again for the sixteenth time before his body went slacked and he hung his head while panting hard from the beating.

"Sixteen. That does it for your beating, gaki." Anko said before walking back around and stood in front him before grabbing his head up to make him look up at her. "Did you enjoy it?"

"N-No. No I didn't enjoy it at all. P-Please, Mistress. Please let me go now."

"Ahah! I don't think so, gaki. We're not done yet." Anko stated before looking down at Naruto's cock and noticing something dripping from it.