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Island Fantasy
Date: 9/10/2017, Categories: First Time Shemales, Author: SandyCrossdresser
... ahead and pick which room you'd like, I've got to wait for my things to show up anyway so we might as well get you settled in." A look left and a look right and you decided on the room to the right. I followed you in and offered to help you get settled in. You blushed heavily as you unzipped your bag and I glanced over and saw that it was completely full of women's clothes. I smiled at you and said, "Listen Sabina, I knew you were going to get dressed in the things that make you comfortable and I'm totally fine that, in fact I practically f***ed you into joining me here. <smile> So there's no need for you to feel embarrassed or ashamed... do you understand?" "Yes, I understand, but old habits are often hard to break." you said with a smile in return. Just then there was knock at the door and I excused myself to answer it. It was that cute cabin girl with my bags. I thanked her again as she carried them to the room I indicated and I was almost as shocked when she opened my bag to pull my things out and hang them up or place them neatly into the dresser drawer. "Oh sweetie,, you don't have to do that, I can put my own things away." I said. But she responded by just smiling and continuing to put my things away. Then as she left she told me, "I don't normally do that for customers unless they request it, but you showed me great kindness before and I was just returning the gesture." After saying that she smiled at me and hurried from the room. I felt warm... her affection was ...
... obvious and I was reveling in it. I had a distinct feeling she didn't see to many Americans around here. I returned to your room and saw that you had finished putting your things away except for what appeared to be a nightgown and a couple of other pieces of lingerie laying on the bed. You were standing there looking like you were not sure how you should proceed. I came right out and said, "That looks like a good idea, getting ready for bed. Its late and we have a big day tomorrow." <wink> Followed with, "How about we both get ready for bed and then I meet you back out at the table for a little night cap before we head to bed?" "I'd like that." you say. And with that I turn, close the door behind me and head to my own room to change. I'm not sure why, but I decided to shave and otherwise freshen up before I slipped into my Japanese silk pajama bottoms and my robe. I came out of my room a few min's later and headed to the bar to make a drink for us both. As I sat there and sipped my drink I couldn't help but to hear noises coming from your room as you busied yourself with getting changed. My mind was racing with images of what you must be doing in there. I didn't know if you were going to come out looking like a woman or looking like a man with women's clothes on. And the clothes, from what I saw there were at least 4 or 5 outfits and many other accessory pieces that I only got a glimpse at. Again my mind raced... I couldn't help but to wonder of how you must be feeling as you got ...