1. Island Fantasy


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

    ... every few min as you nursed that drink along. What could be so troubling to a guy so young I wondered to myself. Even my own troubles when I had them didn't seem like they could compare to yours. I had to help... I don't know what made me stand up and decide to see if I could cheer you up but I look back on it now and I think it was my way of paying back to a society of people that had really welcomed me into they're world, me, a complete stranger and foreigner. I walk up to your table, stand there, looking down at you, not saying anything until you lift your head and notice me there. "HI,... What seems to be the problem buddy? Did your girlfriend dump you?" I asked with a warm and sincere smile on my face. All you responded with was a shrug of your shoulders. "Mind if I sit down? We can talk about it if you'd like?" I asked... Then, "Let me buy you another drink, it looks like you could use a refill" I motion to the bartender and got two more of your drinks on order. Then I pulled out the chair across from you and sat down. "Come on buddy,,, it can't be that bad... can it??" I asked as I continued to try and get you to open up about what was bothering you. The drinks came and I gave the waitress a nice tip as she picked your old drink from your hands and replaced it with a fresh one. You drank, deeply this time. "My name is Jack, what's yours?" For the first time you look up and into my eyes, "My name is Pradeep, and thank you for the drink, it was most considerate." "Its ...
    ... nice to meet you Pradeep, I know I may not be much but I am a good listener,, go ahead and try me out." I say. You give me a little chuckle, a good sign, but you say, "I think I'll need a few more of these before I can open up like that Jack." And with that being said we ordered another round,, and another.. until we were both feeling very little pain if any. Then you said to me, "No one understands me,,, hell, I don't understand me" I respond with, "What don't they or you understand Pra?" "I can't tell you... you'll think I'm a freak" you confide to me. "Listen, I can't be sure that I won't be a little freaked out by what you might tell me, but I can tell you this,.. as long as what ever it is isn't hurting others or endangering yourself then I'll at least be understanding about it,, how's that?" Your eyes opened wider as you took me in again. For long moments we just looked at each other. Then you said, "OK, you asked for it... " and with that you simply undid three of your shirts buttons and pulled your shirt open as far as that would allow. I couldn't help but to just stare... part of it was the shock of what I was seeing and part of it was the amount of booze I'd already had that night. But stare is what I did, for what seemed like hours but was probably for ten seconds. Under your shirt you were wearing what appeared to be a ladies bra. It was pink satin with lace trim around the top edge of the cups. My eyes flicked from your bra to your eyes and back... several times. ...
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