-
Island Fantasy
Date: 9/10/2017, Categories: First Time Shemales, Author: SandyCrossdresser
... and clingy bikini. You were working hard at your walk, trying to move as feminine as possible because you knew I was watching your backside and that had brought a smile to your lips as you moved away from me. "Now I know your teasing me Sabina." I said with a grin and I headed for my own room. You just smiled wider and turned into your own bathroom. I called out to you as you were closing your bedroom door, "I'll give you 20 min to shower and freshen up, then I'll come over and help you pick out something to wear." "OK Jack,, see you in a couple of min honey." you reply. After 25 min I return to the living area all refreshed from a cool shower. With the previous night and this mornings sea washed off I felt invigorated and ready for anything. I had chosen a pair of off white linen slacks and a light gray tropical shirt that had subtle embroidery down the left side to the bottom of the shirt. I'd shaved more than normal and hoped that you would like that. Still barefoot I stepped to your door and gave it a few light knocks which you answered right away, "Come on in Jack." you said through the door. Which I did but not before having to swallow a lump in my throat and taking a deep breath to steady my nerves. Stepping into your room I see you sitting on your bed wrapped in your towel with another towel wrapped around your head. "Hi." I say as I move towards you and sit next to you on the edge of the bed. "Feeling better after your shower?" "Oh yes, I feel like a new woman." you ...
... reply with a noticeable reddening of your face. I just smile and nod as I totally understood how you were feeling and felt the very same way. "So tell me Sabina my dear, what do you feel like doing today? That might help with what outfit we pick out for you." "Jack, you know I'm here for you, so why don't You tell me what we're going to do today, I live here all year long and your the guest to our country so what is it that you would like to do?" I thought about it for a min as you pulled the towel off of your head to reveal your hair already dry, like it had never gotten wet from your shower. It puzzled me for a few moments then I realized you didn't dunk your head in the ocean earlier either. Then it dawned on me and I felt like an idiot, you were wearing a wig and didn't want to get it wet like that. I knew you were wearing one of course because you had hair just touching your ears the night before when we met and ever since the first moment I met Sabina your hair has cascaded over your shoulders by a couple of inches. I guess I didn't focus in on your wig because of you, and by that I mean that when you came out dressed as Sabina I saw you as Sabina the woman. I stopped thinking of you as a man altogether I think. It seemed so natural, so right. And now here I am just noticing for the first time that you were wearing a wig and I couldn't help but to smile and shake my head just a little. "What are you grinning about Jack?" you asked. "Oh nothing, just that I didn't notice ...