Active Ink Slinger
Good anal play is learned and gradual.. it should happen over a period of sessions and not just the first time right out of the box.. literally.. tongue.. fingers.. beads.. plug.. vibrator.. and then cock.. it should be an anticipated pleasure for both of you.. and the best lube for anal is olive oil.. it slides easily.. and it's edible.. but always keep in mind it is the ultimate privilege you are offering him.. make him honor it..
