Let a mature woman tell how the strong character and confident attitude of her new boyfriend made her feel and act naive and insecure like back in the days again. She had avoided her entire life to try anal sex, but with him her guard fell. As they made love in the missionary position and she was drenching wet due to her nearing climax, he withdrew himself, gently pushed her knees up to her chest and positioned his glans against her anus. Let her describe in as much detail as possible how nervous she was. She really only wanted to do it for his sake and let it happen without letting on how it actually felt. Have her describe in equal detail the physical sensations she experienced and the physical reactions they caused. Let her report how it was for her that even though they used a lot of lube the act itself felt incredibly invasive.