Monday, 23 October 2017

Trivial Pursuit: One Fine Saturday

When I was young, I could easily pass off as a lady.  Because of my slim built, my smooth and fair complexion and my very soft mannerisms, many men had thought I was a real woman when I cross-dress.  That Saturday was one of those days when I was in the mood for cross-dressing.  

I went to my wardrobe and picked up a nice dress and other sexy stuff including a pair of red lacy panties and matching bra.   I put on some make-up and then finally don an amazingly realistic-looking wig, a pair of high heels and I was ready to paint the town red.

While stopping for a bite at a popular coffee house at Shaw Centre, I noticed the looks I attracted.  After I had my fill, I headed next door to Tropicana.  I strutted into the foyer of the building, with my purse slung over my shoulder. My wide skirt bounced as I walked across the lobby and entered Rasa Sayang, the pub well  known with both locals and foreigners.  I glanced around and noticed a bunch of men turning and looking at me, and I smiled at them, but continued walking towards the bar. I took a seat and ordered a campari. 

Sitting at the bar, I occasionally turned so my fake breasts would bounce a little. I sat there for a good while, until a guy finally stood up and approached me. "Hi," he said, "I'm James." He stuck out his hand. I reached up with my colored nails and shook it.

"Michelle. Do sit down," I offered, motioning to the empty chair.   "So, Michelle, how is it that a beautiful woman like you managed to get out alone? And on a Saturday evening?"

"Oh, I don't know," I said casually, "I've just been waiting for the perfect man." Then I looked at him, and reached over to grab his hand. "And you, hot stuff, may be it." He smiled an amazing grin, larger than any I'd ever seen, and leaned over and whispered in my ear. "Hey, Michelle, would you like to get out and head somewhere more private? Listen, I'm bi, and I know my friends over there would like to get a shot with you too. I hope you are not offended with my straight-forwardness."

Bi? Did he say bi, was all I could think of. Either way, he was in for a night. But I only wanted him. "I think I'd only like your company tonight, James."

He paid for the drink, and we left. He drove me to his apartment. We stepped inside, and I told him some sexy things about how I was going to make him happy and I could see a bulge forming in his pants. He led me to his bed and that was when I noticed the framed photograph above the bed - an image of a happy couple on their wedding day.  We lay on the bed and started kissing. His tongue dove into my mouth, our tongues intertwining as we frenched.  His hands reached for my chest, squeezing the fake tits.

I could feel his penis sticking up, and I unbuttoned his pants, tore down the zipper, pulled his pants down to his ankles and finally removed his underwear. There, a respectable 6-inch beauty was staring me in the face. 


He thought I was going to suck it, but instead, I surprised him, and threw off my shoes and my panties so fast he barely had time to react.  Then without any warning or foreplay, I sat on his manhood.  I was in ecstasy. My cock burst out of it's hold, but it was okay because I was facing away from him, and I slid down as far as I could, moaning in joy. He pumped up and down, sliding around inside me and then reached around and pulled the dress off, but his eyes were closed, and he took off the bra. The fake tits fell, and as he tried to grope my them his hands met with nothing but thin air. He opened his eyes and looked, and saw .... 

"What the fuck . . .  you're a guy?" I nodded. He didn't care, obviously, because he grabbed my penis and began pulling at it, making me moan even more. His cock pulsed and vibrated, as did mine, and then he exploded inside of me. I was about to go too, but I slipped off him in mid-cum and threw him back, quickly getting on him, sucking him, as he rammed his cock in and out of my  mouth, and as I sucked in the cum, he exploded filling my mouth with his sweet nectar. We both grew limp and laid in each other's arms for a while.

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