1. Island Fantasy


    Date: 9/10/2017, Categories: First Time Shemales, Author: SandyCrossdresser

    ... "Well Pra,, I'm not going to say I'm not shocked because you could tell I was, but, I'm not going to say your weird either. I'm sure there are lots of people out there who like to wear bra's like that." "Its not just the bra." you say. "Really?" "What do you mean?" "What I mean Jack, is that I like to wear anything feminine. I rather wish I was a girl you see. I can't help but to feel like I was born with the wrong body, that I should have been born a woman." "Wow, when I came over to cheer you up I didn't know what I was getting into now did I?" I said with a little chuckle. "I'm sorry Pradeep, I wasn't meaning to sound critical of your feelings. Is this the big reason your over here being so sad?" "Yes, that and I've had these feelings for so long and not a sole to share it with....... until now." you continue with, "Thank you Jack, you've been a sweet guy to be so understanding and non judgmental." "Oh,, don't be too quick to thank me Pra, I have a little confession to make too and maybe that would make me just as crazy as you are." I say with a laugh. "I have to admit I was shocked at first when seeing that bra under your shirt but I just can't help thinking how cute it looks, and now I wonder about how it makes you feel when you put it on." "Do you dress up all the way as a woman? Ever?" You confide to me that you've been dressing as a woman for about 4 years now and only when you've had a chance to be out of the country where no one knows you. And that your convinced ...
    ... that your f****y, mom&dad and one s****r would NEVER understand something like this. I lean over the table a little and ask you, "Pra,,, do you have a girls name that you use, or does Pradeep work for both?" Smiling.... "When I dress up,, I liked to be called Sabina." you say with a deep red blush. "That's a very pretty name... would you mind if I called you that now?" Blushing still... "No, I wouldn't mind at all, in fact I'd quite like to hear it from another person." "Tell me Sabina <wink>,, when was the last time you were able to dress up?" "Oh, its been more than 6 months since I've had the opportunity for that." "That's a shame! is there anything I could do to help? Maybe offer you a place where you could dress freely without any worries of getting caught?" You ask me where a place like that could be and I told you about my seemingly private island paradise. Secluded, no other patrons, A private beach. "So what do you say Sabina,,, can you take a few days off from work?" "I promise not to be anything but supporting... It might even be a little fun." You look into my eyes and think carefully about your answer.... "Yes... I can get away for a couple of days." Part 2 "That's great!" I reply, I then stand up from the table and take a step away... turn back to you and with a smile I say, ... "Come on Sabina, I've got a boat waiting." I head for the front door of the club and don't even bother to look back and see if your following me. You didn't know what to do at first but ...
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