By fucking her thoroughly.

The sight of Anna in his bedroom, immobilized by the pillory on top of his bed was a sight to behold and too much to resist. Josh unbuckled his belt, opened his zipper and let his pants fall to the floor. Anna unmistakenly took the sounds for what they were meant to foretell.

"Oh my god, please Josh, yes, fuck your kitten! Pleasepleaseplease, your kitten is in heat and soooo needs your cock. Pleases, Josh, please!"

It took him a moment to figure out how to deal with the shibari ropework tied tightly between her legs, but he decided to just push it aside with his fingers. He did notice while doing this that Anna's pussy was wet and slick and slippery, and she was moaning and purring at the slightest touch of his fingers.

"Yeeeees, Josh, ohmyyesyesYES!", she whispered.

"You haven't answered my question, kitten", he said slowly. "Are you properly tamed and trained?"

Anna moaned even louder. "Yes, Sir, your kitten is an obedient little cat. She knows how to please her Master!"

"And how exactly does she do that?"
"By... by... offering him her pussy", Anna wiggled her bottom at him eagerly. "And by... by begging him to fuck her!"
Josh felt as if his cock was ready to explode right here and now, and he didn't know how longer he was able to savour this moment without cumming immediatly, so he decided to take her at her word, made one step forward, and pushed his head right between her quivering nether lips.

Anna gasped and moaned.

Josh grabbed her hips and started fucking her with hard, deep thrusts. He felt her pussy clench tightly around his cock, he saw her whole body shivering and he needed to concentrate to not be overwhelmed by the situation: Here he was, fucking his secret crush Anna from behind, while she wore a cat girl's costume, a shibari and was stuck arms and neck in a pillory in his bedroom. And she was fucking enjoying it and screaming for more!

"Your cock is so big, Josh! It's huge! And it's the best one I've ever felt! The only one I ever wanted to feel inside me. Oh fuck! Oh FUCK!"

Josh groaned and slammed his cock even deeper inside her. If she kept talking like this, he'd...

"Please cum, Master! Flood your kitten's womb with your seed!", he heard Anna scream.