1. Jessie and the Office Girls


    Date: 10/16/2015, Categories: Crossdressing, Author: JessieCD

    ... going to cum. Tracy laughed as I shot my cum deep inside of her. “You really are a sissy girl that craves a nice cock in your ass. You can’t even last two minutes inside a pussy while getting fucked by a strap-on.” I was humiliated. Tracy got off me and then sat on my face. “Clean me up! You are a worthless sissy that can’t even please a woman.” While Karen kept fucking me, I cleaned Tracy’s pussy of our combined juices. Finally Karen got bored with me and removed the strap-on from her waist. I felt more movement as Sue got into position with the strap on and started fucking me with it again. While Sue was fucking me, I noticed that Karen and Tracy were going at it with each other and eating themselves from one orgasm to another. It was something that I couldn’t deliver to Tracy. As Sue kept ramming that silicone dildo in and out of my ass, I became totally lost in deep thought of what was happening. I had my office affair with the beautiful Tracy, although I was ashamed that I didn’t last with her. I realized that my highlight was letting Karen and Sue have their way with my boy pussy. Ironically, Sue rammed the dildo deep into me and I started to cum all over myself just as she was having an orgasm from the stimulation she received by ramming that dildo into my ass. I was spent. After tonight, I knew I would never be the same. I was well on my way to being a complete sissy girl who would never be able to fully satisfy another woman again. Instead, I was the woman, and either others would satisfy me, or I would satisfy the males. When the night ended, Tracy drove me back to the office. As I exited her car, Tracy called out, “Jessie, Dan is right. You do make a great woman and you have an ass that would satisfy any man, but you are really lousy with satisfying a real woman’s needs.” With that, she left me at the work parking lot. I got into my car, drove off to home wondering what else would be in store with me.
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