A Game within a Game Part 4

Cathy pretended to hear nothing. "Since you were so impertinent and disobedient, Mistress Helena will give you a spanking. She will start with twenty slaps, on each bum ten. Lower your panties, sissy."

Rob did as was asked.

"You may proceed, Mistress Helena," and with a bright smile Helena started giving him twenty slaps. She was inexperienced, but still she had a hard hand and Rob's bum soon reddened.

After giving Rob twenty slaps, Rob had to stand up. He wanted to pull up his panties but a sharp "Leave those panties!" stopped him. He now really felled humiliated. "Step back sissy," Cathy ordered him and he did as was asked, shuffled slowly, with his panties on his ankles.

She walked around him, lifted his petticoats and dress and inspected his bum. "Hmm, it's been a bit red, but not much." Then she lifted the front of his dress and looked at his dick, what had been hardened a bit, but under her destructive look his dick softened soon. "That's what I thought, sissy. You have a real sissy dick and sissy dicks must also behave. The next time I see sissy's dick become hard again, I will have something to do about it."

"Mistress Helena, can you fetch that hairbrush from the table? Right sissy, your next lesson. We will color your bum even further. Mistress Helena, please take the seat again, and sissy, you know what to do."

Without complaining Rob turned over Helena and rested again on her lap.

"Mistress Helena, please give him on each bum five strokes with the hairbrush. I want to hear him moan, so do your best."

With considerable force Helena gave Rob ten strokes. The first ones he could bear, but his arse went a bit sour and some hits really sting. At stroke nine and ten he moaned softly.

"Well done, Mistress Helena. Sissy, stand up, take a step back."

Cathy inspected him again, this time his arse was bright red.

"Now your front" Cathy said and lifted the front side of his dress. "I knew it, this sissy is not learning fast. He has a hard-on."