She held up for a moment to make sure I was okay. I looked at her and nodded. She pushed forward again, and suddenly a sharp pain hit me as the head p...pped in entirely. I must have winced in pain because she stopped again and looked in my eyes. Still without words, I nodded and moved my free hand to her hip, giving her a slight tug to encourage her to continue. Now that the head was in, I knew I had to relax completely or the rest would hurt. I released my balls and laid back a bit, reaching. Then I sat on the bed and spread my legs wide for him to take a closer look. He adjusted the elastic and then tried to cover my pussy with the panties. During this he made sure he had a few fingers inside my panties trying to feel my pussy and then covering it. Then I rolled over and he did the same to my ass. I then asked him to pickup my frock and get it to me. He got it and tried very hard to get me into it…then he said that this was the first time he was dressing up a lady and he was not. More

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