Continue the caning until she's , then offer to let her cum if she can get herself off with just the cane.

Theo continues his relentless ****, the cane leaving a crisscross of red lines across Kelly's quivering flesh. Each impact sends shockwaves through her body, jostling the dildo inside her and forcing strangled cries from her lips.

Kelly's struggles grow more frantic, her body writhing in its inescapable bonds. The ropes of the box tie bite into her skin as she twists, her arms straining uselessly behind her back. The ceiling rope keeps her upright, denying her even the small comfort of curling in on herself.

"Please," Kelly gasps, her voice raw and ****. "I can't take anymore. I need..." She trails off, unable to articulate the burning need consuming her.

Theo pauses, the cane hovering tantalizingly close to Kelly's flushed skin. "You want to cum, don't you?" he asks, his tone deceptively casual. "I'll let you, but only if you can get yourself off with just the cane. Think you can manage that?"

Kelly's eyes widen, a mix of desperation and determination flickering across her face. She nods frantically, beyond words, willing to try anything to find release.