What a lucky boy… today we’re going to be popping your pegging cherry…. under one condition. That you beg me to do it the entire time. Tell me how badly you want me to be in yours holes, and how badly you want me to use you however I please. For a first timer, you take my strap so well… and if you want to be a proper sissy, and graduate to the next step then you’re going to have to show me how bad you want my cock. I keep pegging you until you leak cum through your cage, and once I am satisfied with the milking I give you, I graduate you to a fully flat cock cage.