Shemale Sex in Pittsburgh

When I first thought of arranging a meeting with a shemale from Pittsburgh, I had images of Jack Lambert in a skirt and heels, or the East German women’s weightlifting team from the 1976 Olympics in Montreal. Thankfully, these stereotypes of the average ethnic Pittsburgher did not apply to the transgendered population of the Steel City [although the shemale penises that I sucked on in Pittsburgh were hard as steel ].

My last business trip to Pittsburgh was in the Fall of 2005. I had been corresponding with a beautiful lady via email for a few months before the trip, and I had arranged evening out with her during my stay. My first Pittsburgh date was with Natasha, a stunning statuesque blonde originally from Germany. Natasha’s pictures and webcam definitely didn’t do her justice. She met me at my hotel’s bar before we headed off to Mt. Washington for dinner. Besides her long legs looking incredible in the stockings that she was wearing, I immediately noticed how feminine her hands were. I didn’t want to stop holding hands with her once I felt how soft they were, and her perfume completely captivated me when I leaned in to kiss her on the cheek when we met.

If you remember Flashdance from the early 1980′s, you’ll remember the scene in the restaurant where Jennifer Beals was eating lobster and put her foot in her date’s crotch. Natasha caught me by surprise with that one. She had been playing footsie with me under the table at dinner during the appetizer and entree, but while we were waiting for desert, she started massaging my cock through my trousers and had me totally distracted, much to her enjoyment. She could have led me out of the restaurant by my erection at that point and had her way with me.

We had taken the Duquesne Incline to the top of Mt. Washington for dinner, but I had arranged for a black stretch limo to pick us up after dinner for a tour of the city and some intimate time behind the limo’s privacy screen. Natasha didn’t waste any time once the driver closed the door to the limo. She kicked off her heels and laid her stocking legs across my lap. She put her arm around me, and I soon found her tongue deep in my mouth with her long hair falling down around my face. I lifted up her skirt and could feel her growing lady cock against my leg. She was straddling me in the backseat now grinding against me. I was ready to explode in my pants.

I picked her up and moved her beside me on the seat and got down on my knees before her. I unbuttoned her blouse, and kissed and sucked on her perfect D-cup breasts. Her hands were on the back of my head as I kissed my way down her chest and stomach to her panties. I was licking her thick shemale cock through her panties before pulling them down and licking her from her cum filled balls to the tip of her lady cock. I was humping her stocking leg while I was sucking her off, and I heard the privacy screen being lowered by her as she giggled. I came on her stocking leg while her lode spurted into my mouth and down my throat over and over again.