1. Island Fantasy


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

    ... yourself dressed. Its been so long since I've had any thoughts of myself like that... not since I was 10... oh my god.. I'd totally forgotten about that summer in North Carolina.. when I wore that dress around the house for weeks. Not even caring what my siblings were saying to me... and I remember my parents forcing me to change before we would go anywhere. I thought it was unfair, that I was already dressed in what I wanted to wear... Is that why I wanted to invite Sabina to my hotel for a couple of days?? Or am I just a nice guy?? Both... it has to be both, I am a nice guy and my acceptance of Sabina for who she is must be because I have the same tendencies myself.... Oh wow, how long would it take a shrink to fix me?!? I laugh out loud at the absurdity of that last thought,, I know I'm not broken and neither is Sabina. Just then your door opens.... I turn my head just in time to see you step from the opening. I'm not sure how far my mouth hung open just then but looking back I'm thinking it was a lot judging from the sudden worried look on your face. You just stand there not sure what to do or how I'll react and my shock is quickly turned to delight as a broad smile stretches across my face. Your gown is white satin, full length, covering even your bare feet. I can see darker straps under your gown that I quickly recognize to be garter straps and the tops of a pair of stockings. That's when I look back at your feet and notice they weren't really bare but covered with ...
    ... those same sexy nylons. I look back up and see that you don't have breasts like a woman but you do have pretty little dark nipples that I can see through your night gown. Farther up I see that you have applied some makeup, not a lot, not so much that you look like a movie star, just enough to let your feminine side come out to include a lovely shade of pink lipstick. Topping off your outfit, you've put on a wig, same color as you natural dark brown hair but longer and with a few waves in it. I close my mouth and swallow before saying, "Oh my... Sabina, you are just Lovely... perfectly Lovely. I can't believe how nice you look! Please, won't you join me?" I say as I offer you a seat near my own chair. I can't take my eyes off of you as you walk sweetly to the chair I'm holding for you and sit down crossing your legs. Part 3 I offer you the drink I'd made for you a few min's earlier and you cupped it with both hands as you took a small sip from the edge. "Thank you Jack." you say. "Sabina,,, I must say, you look quite striking as a woman, very elegant and sensual." I said as I return to my chair and settle in as I continue to stare at you. Blushing, you smile and lower your eyes as you thank me and I respond with a desire for you to feel comfortable, for you not to worry about how I feel or how I'm going to act. As a matter of fact, I confide in you the fact that I had once worn a sun dress around my house when I was 10 and had completely forgotten the memory until I sat right here ...
«12...567...28»