The Flirt

The whip had always been familiar to her. As a kid, it was her punishment by her stern father who believed in corporal punishment. Also by her school headmaster who was a strict disciplinarian, and seeing that she had a smart mouth, she was always getting disciplined. But now Mistress Persephone was on the other end of the whip, and it was her turn to seek revenge for all of those whippings she received as a child.

“Bend over, worm!” she yelled to her male slave, Brian.

Brian bent over and anticipated the sting of the whip on his ass cheeks but it didn’t come. Waiting, waiting, waiting……why was she torturing him this way? When would the sting come? The hardest part was the not knowing. Huge anxiety passed over his tense skin as he braced himself for the upcoming sting of Mistress Persephone’s largest whip.


“AAAAHHH!!” Brian screamed.

This was no ordinary beating for pleasure. Mistress Persephone was very angered by Brian’s attitude. It seems that Brian flirted with a waitress at a topless bar and Mistress Persephone will not have any of her slaves straying from her.

Another crack comes down over Brian’s fleshy ass. The sting feels like a million razors piercing his tender skin. Tears start to well up in his eyes, but he’s a man and he’s not going to give her that satisfaction of shedding a tear!

“Just two strokes and you’re already turning red, Brian. Looks like you’re going to be in for a long night.” Mistress Persephone chided.

Brian was bent over the wooden horse with his hands manacled in the front of him. His pants were down around his ankles and his ass was exposed to the world. It was so humiliating to have a woman dominate him this way! His nakedness exposed to anyone that could walk in, and his penis free hanging in front – so vulnerable! He hoped and prayed that his punishment would be over soon so that he could cover up his most private parts.


OUCH! When was this going to end? Brian was now starting to really feel the punishment and it was only the beginning of his session.

“This will teach you to stray from Mistress Persephone. When I’m done here, I’ll expect a full apology, but that won’t be for quite awhile”, the evil lady smirked.

Mistress Persephone continued to give Brian a few more strokes. Each of them harder than the previous one. Brian continued to yell at the top of his lungs at each point of contact with his ass. Just as Persephone came to the 10th stroke, she decided to give her best slave a little break. Rubbing his very red, hot ass she said:

“The welts are starting to show up, Sweetheart. That is my favorite part. I just want to show you my handiwork.”

As she swung a full length, mobile mirror behind Brian’s ass, he lifted his head to look into the mirror in front of him. The reflection of his cheeks in the mobile mirror startled him. Good God! How could she be so cruel? His ass was on fire – stinging as if he’d been attacked by thousands of bumble bees. And the welts were so big, they were starting to blister his tender skin.

“I think you’ve had enough of the whip. I think the paddle is in order now.” Mistress Persephone explained.

“No! Please not the paddle! You’ve already blistered my ass worse than it’s ever been before! The paddle will only aggravate the welts! I’m sorry, Mistress Persephone. I’ve learned my lesson and I’ll never do it again! I swear!” Brian begged.

“No, I’m sorry Brian. You’re getting what you deserve. Next time perhaps you’ll think with your head and not with your crotch.” Persephone scolded.

With that said, Persephone got out her biggest paddle and lined it up square on Brian’s ass. She saw him looking at her in the front mirror so he could anticipate when the strokes were coming. She drew the paddle back and was just about to strike…….and brought the paddle down about an inch away from Brian’s ass swiftly! She was now toying with him so that he could not guess exactly when his beating would come. She was smiling devilishly staring at him. He was panicked knowing that he was in for a pretty good beating this evening. Another few fake swings of the paddle and then:


“OH FUUUCK!!!” Brian hollered.

He had never felt such pain before! The paddle was only adding to the already sore, swollen welts from the whip. Persephone paddled Brian several more times as he screamed in agony. But wait…..what was happening? Brian felt his dick hardening. Was it true? Was this extreme pain really turning him on? He had never felt such pain, or such pleasure. Persephone witnessed the event:

“Ahh, I see you’re finally starting to enjoy yourself. Hmm. What can we do about that?”

“Please, Mistress Persephone. I’ve had enough. I’m very sorry and I’ve never been so humiliated in my life.”

Persephone finally gave into Brian’s pleas. She came up behind him on the wooden pony and bent over him to reach around and grab his hard cock. She felt his 8 inches in her hand and started stroking his member. Brian felt Persephone as she leaned against his welted ass. She was causing him more pain by touching his ass, but she was also causing him great pleasure by stroking his hard dick.

As the minutes went by, Persephone stroked harder. Her hand moving up and down on his rock hard cock.

“Uuuuhhhh,” Brian moaned.

“You like that? Do you like me to stroke your cock and lean over your hot, welted ass?” Persephone teased as she stroked harder and harder.

“Oh God, yes! I’m gonna cum, Mistress!” Brian screamed.

“Cum on, Baby. Cum all over my hand.” Persephone instructed.

Brian’s cock finally exploded as his white, warm jizm oozed out all over Persephone’s hand.

“Uuuuuhhhh,” Brian moaned again.

“That’s my boy. Now you’ll know why not to stray from your Mistress. Now go and clean yourself up in the bathroom and come back out and apologize to me for your behavior.” Persephone said as she unlocked Brian’s manacles.

Brian cleaned himself up, apologized to Persephone and never went back to the strip club again.

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