Fear raised its Beastly head upon hearing Sterling's voice. Despite the kind tone it was still the smooth call of a greater predator. She hadn't inflicted final death though, so Kenneth calmed the instincts. It wasn't like he could flee right now anyway. Now she just needed to remove the nails...
Her next statement brought a brief flash of anger, as he immediately assumed this was some sort of humiliation she had contrived while he lay asleep. He passed it off as a grimace of pain. No, so far Josephine had been more than respectful, there was no reason to start abusing him now for no reason. She likely saw this as a way to further test his will, strength, and faith. He would do his to prove himself.
"Alright," he acquiesced, though if he had still been mortal, he would probably have tears running down his face from the idea of the coming pain. Just a moment in time. A drop in the sea of eternity. Like ripping off a band-aid.
Two down
Gilroy didn't even bother trying not to scream. He closed his eyes, counted down from three, and then contorted his body to pull as hard as he on his left hand. If his voice had not been as high and pitched, it might almost be called a roar instead of a screech. The hand hit the head of the nail and stopped momentarily. Kenneth kept pull though. Flesh and bone tore and parted. Bits of sinew and skin hung off the metal, still dripping with vitae. Barely waiting to savor it as a victory, Kenneth jerked the other side with enough force that he felt a couple bones give way and crack. The iron pulled the bloody white out the other side.
Gilroy collapsed back. His hands shock and refused to follow anymore of his commands. The Haunt forced himself to breath. It was useless air of course. Kindred biology didn't make sense that way. However, it helped him gain back the will for the final step.
His feet proved less compliant. Not only was there more to pull over but without his hands nailed down, Gilroy had no good handholds to brace himself against. He yelled for five seconds before his body's mortal instincts kicked and shut down the struggle to prevent more harm to itself.