1. Rita and our first time


    Date: 10/7/2016, Categories: True Story, First Time, Transsexual, Author: Nomad14, Rating: 90.9, Source: sexstories.com

    It has taken me a long time to decide to tell this story. About 3 years ago a new girl started working in the office. At first she started just answering phones, and keeping the meeting minutes on our sales meetings. She is about 5' 10", kind of thin, and always dressing very nice. At the time I would guess her to be around 22. Over the next year she performed really well at work and ended up splitting her time between myself and another V.P. at the company. Then about a year and a half ago she notified us that she was taking another job closer to where she lived, and also gave her more room for advancement. Her and I had grown somewhat close, and had been meeting on Fridays for a drink. About a month after she started her new job I had texted her about meeting for a drink. She agreed and we met at our favorite bar. We had more than a few drinks and she started talking about her life. I asked if she dated a lot and she said not much. I was kind of blown away as she was very hot. She shared that not many really wanted to get to know the "real" her. I have to be honest here, she had great tits, and a ass that was perfect. She then shared that most men are pigs, and are liars. About three hours later I was feeling a bit drunk and I could tell she was feeling it to. We decided to take cabs home, but as she got in the cab I gave her a kiss which she returned with a bit of tongue which I like very much. Two weeks later we decided to met at a bar by her new condo for drinks as ...
    she wanted to show me her new condo. We had a few drinks but was not drunk. We then walked down to her condo and she showed me around. It was nice, and very modern looking. I have to be straight here, I was thinking about nothing but her tits. When she was done showing me around she asked if I wanted some wine. I said sure. We sat down on her couch and had some wine. I then leaned over and kissed her, she seemed to like it but then pulled away. I said I was sorry if I was getting to forward. She looked down and said, no, it's not you, it's me. I said, what do you mean, is it another guy? She said, no, nothing like that. She then said, if I tell you the truth it will make you hate me, plus, I really don't want to hurt the great friendship we have, and I should never have let it get this far. I said I just don't understand. She then said, I was not born a girl, and please don't hurt me, and hate me. I said, hurt you, what do you mean not a girl? I then said, I could never hurt you, what do you me. She then said, I am a guy down there. I have to be honest, and maybe I am not up on current events, but I had no idea what she meant, not born a girl, and being a guy down there. She then said, I was born knowing I am a girl, but I was born a guy. I must have sounded like a jerk, and said, you mean you have a penis? She said, yes. I have to be honest here, I felt a bit sick, and confused. How can a guy look so much like a woman? So hot? She started to tear up and I was really in brain ...
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