I told him how well he looked and jokingly asked if he wanted a bust to go with it! He blushed and told me that he'd wanted to dress up for ages but h...s ex didn't want him to. I found an old padded bra and some silicon push ups which gave him some cleavage under the top. I asked if he wanted to go the rest of the way and when he agreed I got out some stockings and skirts I thought would suit him. Luckily I had a pair of boots which were about his size as well, so I took the lot into the spare. He took something that looked like a thermometer that he pushed through her cherry. It went slowly to stop at about three-and-a-quarter inches inside her. That came out, and he put in something else that he gently turned a knob on that slowly stretcher her cherry open. He slid that out too.He let her relax and came over to stand beside her and said, “Depending on how you look at it, we have good news. To check what I need, I have to use a finger. With a pre-pubertal girl, or one just starting. More

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