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Always make sure he enthusiastically wants to try pegging first, and then if he's still a little nervous about being Dominated by The Tool of Male Oppression or whatever, start with a dildo that's specifically designed to look non-penis-like and has a nice little curve for perfect P-spot stimulation (like the Right Spot.) Also — v. — make sure you get equipment that's going do something for you too. He can steady himself by putting his hands on his thighs, but if the combination of first-time jitters and the whole must-engage-thighs-of-steel aspect is too much for him, he can also brace himself on the edge of the bed.