He glanced over at John at the noise of someone walking and grinned. "Well.. well... well.. it's a regular family reunion around here," he drawled. "How's the wife?" he managed to get out before the bullet hit him square in the shoulder. Azazel's hold on Dean fell for a moment but he regained it before too long and clutched a hand to his now injured shoulder.
It didn't last long though as another shot hit close to the same spot, having been so intent on trying to keep Dean in his hold he hadn't noticed Jo come up from the other side and draw her own gun. He lost the hold on Dean, he may be a demon but it still hurt when people insisted on shooting him. He half turned his head to shoot a glare at Jo. "You know I'm starting to change my opinion on you," he spat out before settling his eyes back on John and Dean.
"Good," she replied, keeping her gun on the demon.