This is a print version of story My First Time with a Shemale by TSfanxxx from

My First Time with a Shemale

I had watched porn for a long time, graduating from straight porn to videos of shemales, falling in love with TS stars such as Leilani, Julie Bond, and the gorgeous hermaphrodite Dane Harlowe. However, as much as I fantasized about being with a shemale or cross-dresser, I never thought it would happen.

Then one night when I was living in Indianapolis, after being out drinking and dancing, I stopped at the local adult video store. I had parked near a white van and, as I was drinking some more of the six-pack that I had in my car, I saw that there was a woman in the driver’s seat of the white van. She was looking at me, and, although she was beautiful, she still looked like a man wearing make-up; I immediately got a hard-on, hoping that she was a shemale and that she would want to be with me. I got out of my car and went over to her. As I approached, she rowed her window down.

“How are you doing?” I asked.

“I am fine,” she said in that feminine and yet slightly male voice that I had often heard in shemale videos.

I stood at her van, and we made small talk for awhile. While talking, she put her hand on my arm, then she asked, “You know I’m really a guy, don’t you?”

I smiled real big, “Well…I was hoping that you were!”

Then she laughed…a full sexy laugh, and my dick became rock hard. “Follow me,” she said.

I went back to my car and followed her in her van. After about fifteen minutes, we pulled into an apartment complex, and we both got out. She took my hand and led me into her apartment building and up some stairs. She let go of my hand to unlock her door, and then when we were inside, she immediately grabbed me, and we began French-kissing.

I lifted her skirt to grab her ass, and she thrust her hard dick against me. I knelt before her, lifted her skirt, pulled down her panties, and began sucking her hard cock. She put her hands on the back of my head, and, for the first time, I took a guy’s dick fucking my face.

Just before she was about to cum, she lay down before me. “Fuck me. Fuck my asshole,” she pleaded.

Without hesitation, I moved on top of her and slid my hard dick inside her ass. I loved watching her masturbate as I fucked her. As soon as I saw her cum shoot out of her dick, I too came, screaming aloud as I filled her asshole with my cum.

I collapsed on top of her, and we fell asl**p. When the morning came, I was the first awake, and I began stroking her cock. I couldn’t wait to fuck her again.

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