How about Harry laying on his front, a pillow under his tummy to bring his ass up. You kiss his cheeks, nibble the sensitive skin and blow some cooling air on the light purple marks. You take the plug and slowly slide it in his ass, but just a little bit so you can hear his moans agaist the bed sheets. Harry arches his back, which makes the plug slide deeper. "Tsk tsk, baby. Someone's a bit eager today, aren't you?" You say and take the plug out. "You're gonna have to be a good boy for me."