First time and what great fun

He told me that he is a shy and very feminine boy and that sometimes he dresses up as a girl, which to his liking and later mine, he not only feels great in but looks good too. When asked which he prefers he said that he was born and lives as a boy but deep inside he was meant to be more than that. I have to admit I was not only intrigued, but I had an erection the entire time just talking and thinking about the possibility of meeting this guy. So we set it up. I was scared and thought that I’m probably going to chicken out at the last minute, but it was all way too exciting not to at least consider. The plan was to help each other fulfill our fantasies and so when we met the very next day, I showed up as I am, a guy looking for not only a good time but possibly something more; and to my great and pleasant surprise, “he” was a beautiful woman. I walked up to the car she was leaning on very slowly and absorbed the entire view.

Cute little black shoes on a small heel showed perfectly painted pink toenails; her feet were small and nicely curved which looked very sexy. Long and smooth legs were bare up to the knee. She had on a colorful summer dress, which exposed the back; smooth arms were also bare except for a cute bracelet. I think the biggest surprise were the hands, which were also very feminine and delicate with nails matching her toes. After all the best way to tell the difference between men and women are the hands and feet, everything else can be changed or covered up. I knew that the breasts I saw was just a stuffed bra, but that didn’t stop my imagination from taking over and I got really excited. Smooth long neck led to a pretty and again very feminine face, big brown eyes had a certain intensity in them and the long black hair that had a hint of dark red in them were flowing over her shoulders and half way down the back. To say the least, I was mesmerized. If he hadn’t told me before that he was a guy I would not have guessed it. He had on a tiny bit of make up that slightly accented his already very womanly face. I was so scared and nervous that the only reason I hadn’t chickened out was the fact that I was really attracted to the girl I saw in front of me.