1. The Cleaning Lady


    Date: 1/10/2016, Categories: Fantasy, Transgendered, Author: jdm320, Rating: 89.9, Source: sexstories.com

    reached down and pulled her up to me. As she was moving up, something strange rubbed against my cock as we kissed passionately. My hands went to her pants and slipped in the back and I squeezed her bubbly ass. It was then that she surprised me, and broke our kiss and sat up on the side of the bed, with her face in her hands and her elbows on her knees. “Ivana, did I do something wrong?” I asked as I sat up and tried to pull her to me. She struggled against my embrace, and I could tell she had started to cry. Again I tried to console her by pulling her to me and received the same reaction. “This was a mistake Mr. J.” she said almost sobbing. “Its ok, Ivana, we can stop if you want to. I don’t want you loosing your job, and if me being married is a problem, I understand.” I replied, with a hint of disappointment. “No, it isn’t either. Unless you tell, no one would know. If we go any farther, I am afraid of what you may do.” “Look, I am sorry about earlier, I am not a violent man, and you don’t have to worry about me saying anything to anyone.” “Mr. J, you know when I told you that I was saving my money to fulfill my life long dream?” She asked as she raised her head. The tears flowing from her eyes making her mascara run. “Yes Ivana, I remember you saying that.” She took a deep breath, “My life long dream is to be a woman.” I guess my shock of her statement was revealed by the expression on my face. She went on to tell me how she had been born a male, but had never been into ...
    men stuff. She refused to consider herself a homosexual, but a female trapped inside a male’s body. In school, she never wanted to play sports and was teased a lot by the kids calling her sissy. When she was in High School, he father had passed away, and her mother allowed her to start dressing as a woman. She had taken the money her parents had intended for her college and had some surgeries to make her a woman. She only had one procedure left. With that she stood and pulled her pants down and revealed a small, erect penis. “See even my penis is evidence that I should be a woman,” she said, trying to laugh. I was stunned. The first emotion that hit me while she was telling me her life story was that I had just let a man suck my cock. As she continued her story, my emotions changed to shame, and disgust for the way she had been treated. I looked at her as she stood in front of me, naked. I looked at her beautiful face, which was definitely the face of a woman. My eyes lowered to her perky breast, the light pink areolas, and the hard nipples. I had never seen tits like that on a man. Then down to her penis. Her penis was uncut, but only two or three inches long and very thin. In reality, I believe my pinky finger was bigger than it was. I had a choice to make. So I stood and stepped closer to her. My cock rubbed against hers as I pulled her into an embrace. My hands rubbed down her back and I cupped her bubbly butt. I raised my hand and lifted her face with my fingers. I lowered ...
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