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. Holy crap some of these dresses were short. Well, I wasn’t going to be the one to initiate the conversation, so I guess I am going to have to dress a little different to get his attention. To me, it felt like this black dress was hardly enough to cover a girl, but I put it on anyway. It barely covered my ass. At breakfast in the hotel lobby, I was getting a lot of attention. I wasn’t used to this much attention. I wasn’t sure if I wanted this much attention and thought I would go up and. More

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