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Island Fantasy

Date: 4/10/2015, Categories: First Time, Shemales, Author: SandyCrossdresser, Rating: 100, Source: xHamster

that you were wearing a wig until just this moment. I'm quite the detective aren't I?" "You don't like it?" concern in your voice. "Oh Honey,, its nothing like that. I love your hair, its so lovely and full. And your highlights glint so pretty in the sunshine." I say with a smile and my fingers gently curling your hair between them. I lean in and kiss you on the cheek to reassure you and to get a whiff of your fresh scent. Delicious. "I was thinking Honey,, how about going for a ride and exploring some of the islands? Would you be OK for that, or would you be too nervous? To be honest, I was hoping I could take you out and show you off a little." "Oh Jack,,,.. I don't know,, I've never gone out more than I have right here with you, I don't know if I'm ready for that yet." "OK then, how about just going for a ride and seeing some of the islands from the boat,, we don't even have to go ashore if you don't want to." I ask. "That sounds lovely,, I'd really enjoy that." you say. So I stood and went right to your closet and opened the door. I started thumbing through all the outfits you brought and came across a pretty sun style dress. It was white with tropical flowers printed around the bodice and again along the hem. It looked like it would come to just past your knees and flair out a little from the waist. "How about this dress Sabina? I think you'd look amazing in it." You got up from the bed and walked over and accepted the dress and promptly turned to face the mirror and ... hold the dress up to your shoulders. "You think so Jack? ... Well, I suppose I can try it on and see if you like it as well on me as you do on the hangar. But first I think I should slip into my underthings." you point out. With that notion I smiled and said, "Mmmm... let me help with that too Sabina, If you don't mind that is." I look into your eyes and search for permission to help with your lingerie and I find it in the form of a demur smile. So I turn to your dresser and open two drawers before I find what I'm looking for, your panties and things. I reverently touch each of your panties as I search the small, neatly placed assortment for the perfect pair until I come across a simple pink satin and lace tanga panty. And I knew that when you slipped it on it would create such a sexy sight as the lace material would be pulled between your cheeks just the perfect amount. It made me tingle just lifting them from the drawer. I set the panties on top of the dresser and continued my search for a bra and found one right away, one that actually matched the color quite well. Again, a pink satin, with the cups able to be folded down making a very sexy demi cup bra for a woman with small breasts like yours but more of a shelf bra for a fuller cup woman. Picking up the pair I turn and hold them out to you, "How about these Sabina, I really love the color for you." You smile at me and accept my offering and say, "Those are some of my favorites Jack, why don't you give me 5 min and I'll get ...