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Head Pusher Step 3: Grab your ass and pull it down towards your face. Put a pillow under your lower back, put your legs behind your head and make sure your shoulders are in front of your legs and it helps if your feet are crossed over your head. Step 2: Open that hole and keep your penis out of it on the edge of the opening of the boxer,. Unfortunately, most of us can't do it. Caution: You can hurt yourself by trying this.