1. Jamie


    Date: 12/31/2014, Categories: First Time, Hardcore, Shemales, Author: freegre, Rating: 100, Source: xHamster

    work and I will miss my class." She laughed, tweaked my semi-hard dick and pushed me away. "Then get dressed lover." I laughed with her and turned away. After getting dressed we left the apartment and returned to her car. She told me she had her own business, a small publishing company downtown. We soon arrived at the campus and she dropped me off. Before leaving we exchanged phone numbers and made plans to meet that evening. I watched her leave then walked onto campus and my classes. It was hard to concentrate on the lectures but somehow I managed. After class, I caught a trolley and made my way back home. My nose still hurt from last night, but my leg was fine, except for a discoloration. I took a shower and dressed in some slacks and a dress shirt. Tonight I would meet Jamie at a posh restaurant for dinner. Afterward we planned to go dancing. I was sitting in a private booth at the restaurant when the waiter showed up with Sherry in tow. I stood up to greet her with a kiss and a hug. "Hi Jonathan. Jamie had some trouble and said that she would be late. So she asked me to break the news to you." I nodded my understanding and pulled out a chair for her to sit." "Thanks. She also said she would grab a quick bite and meet us at the club. I hope you don't mind?" I smiled at her. "Well, such things happen. I must say though that you coming here was much nicer than a phone call." "She thought so too. Anyway, she gave me explicit instructions not to become too attached to you. ...
    She said that was her job." I laughed. "Only hours at a time then?" Sherry grinned impishly. "Only hours? I was hoping more for days with ten minute intervals. We laughed together. After perusing the menu we ordered and enjoyed the each others conversation. The food was good, and Sherry had a great sense of humour. I asked a lot of questions about Jamie and what she told me was enlightening. It seemed that Jamie had never been a man. She was a real woman. But after being ****d in high school she began to hate being a woman. She had explored being with other women but found that there wasn't any kind of connection. She began to study sexuality and explored many perversions. What she found the most exciting and least harmful to her fragile sexuality were she-males. Women with dicks. Most were effeminate men, but there were cases of women wanting to have their own masculinity without losing what femininity they did have. The whole Yin-Yang thing. Anyway, after creating her own successful business, she went and had the operation, a Strapadictomy. Now she felt secure and sought out other she-males with which to have sex. It seems I was the first straight male to fuck her since her ****. Sherry thought the main reason for her involvement with her was being rescued. She was sure she would have been ****d again, and her she-male persona couldn't protect her. But it did. I showed up and saved her. In one shot it seemed I had reaffirmed her. Sherry cautioned me to be careful with Jamie. ...
«12...101112...2627»