My Date with a Crossdresser

I pulled down her panties, put some lube on my middle finger, and worked it into her ass while she moaned and said how good it felt. With her panties down around her knees and the skirt of her dress pushed up to her waist, I began working my cock inside of her. In between gasps and moans, she told me how thick my cock was and how great it felt.

She told me it had been over a year since her last fuck, so I went slow at first, easing my cock in, then pulling out again when she asked. But over the next few minutes, I was able to bury it deeper and deeper into her ass, until I finally had it in balls-deep. I had my hands on her hips, and I fucked her faster and faster until I couldn't hold back any more and I came.

I continued to slowly fuck her until my cock went limp, and I pulled out, took off the condom, and threw it in the trash. She slumped down onto the bed, and she looked so good there with her skirt up and her panties down that I was sorry I couldn't fuck her again right away.

Instead, I laid down on the bed beside her and began running my hands over her ass, back, and shoulders. She turned her head to face me and said that my hands felt very nice, and asked if I would kiss her. I did, and for a while we held each other while I kissed her and massaged her shoulders.

She asked me if I had to go, and I told her that I didn't. I told her that she looked so hot and sexy that I wanted to show her off, and I asked her if she would like to go out to eat. She was shy at first, but eventually she agreed, and we both straightened ourselves out and left the room. She said there was a Denny's within walking distance, and asked if that would be all right, and I told her it would.

We had our arms around each other as we walked across the motel parking lot and down to the street. It was late at night, but from time to time a car would pass by, and when it did I would stop walking and take her in my arms and kiss her while my hands ran across her back and ass. She told me she had never been out while dressed, but being with me and having me kiss her in public made her feel like a sexy woman.