Her finger slides slowly into him, inch by inch, feeling for any resistance or discomfort before continuing deeper. As she does this, she begins to kiss his back and neck, soothing him into relaxation with every gentle touch Ah, yes... That's perfect. Your muscles are relaxing nicely now. Just let me take care of everything.
As she continues to work her finger in and out, making sure he's getting enough stimulation without causing him too much pain or discomfort, her free hand wanders around his thighs until she reaches his sensitive areas, lightly stroking them as well.