1. Sandy's Journey


    Date: 2/22/2024, Categories: Transgender & Crossdressers, Author: byPRTNDR

    ... you'd been there a while, she knew the names of your kids and where you were born.
    
    We figured she was sort of an employee relations ambassador for her husband. She was also sharp as a scalpel. She knew who had Dave's back and who had the knife, and where all the company bodies were buried. She wasn't vengeful or mean or sneaky, but friendly and kind, and very easy on the eyes.
    
    She was of average height, with a perfectly proportioned figure. Healthy, but without the giant tits and ass that seem to be fashionable these days. She had class, the kind that comes from old money. She was always perfectly turned out, her makeup flawless and seemingly unnecessary on her very beautiful face. When that face turned to you with a smile, your whole world lit up.
    
    So when she came walking into my little office space on a Wednesday afternoon, it was a definite improvement to my day. Of course I stood up and walked to greet her.
    
    "Hello, Judy. Good to see you," I said.
    
    "You too, Sandy. I've been hearing wonderful things about you from Dave."
    
    A compliment from that lovely face made me feel a few inches taller, but humility was the right response. "Just doing what he tells me," I said.
    
    "And very well," She replied. "We'd like to thank you. Would you like to join us for dinner on Friday?
    
    Now this was good. He must be really happy. "Yeah, I'd love to," I said.
    
    "Great!" she said. She stepped into me and gave me a quick hug. Her perfume was soft and perfect. As she broke ...
    ... away she whispered, "By the day, Dave tells me you appreciate beautiful things. I do too. Wear something nice, and we'll compare notes."
    
    With that the smile went to 1000 watts. She waved as she turned away. "Cocktails at 6, Sandy. It's just us, so no ties. See you then."
    
    Oh, my fucking God. Dave told her. She fucking knew. What exactly had I gotten myself into?
    
    That night I went home and quickly changed into a pair of thong panties -- the red ones. They made me feel sexy. It's like I felt driven to play to take away the anxiety over Friday's dinner. I got out my toys and lube and cranked up some CD porn on the 'net. In no time at all I was hard. I took the 8" dildo and put it in my mouth, sucking like my life depended on it. I pressed it against the opening to my throat, and tried to relax. I'd been reading about deep throat techniques, and I wanted as much cock in me as I could get. It took several tries. The trick is not the lower throat and the jaw. The trick is relaxing the muscles at the back of your throat. Eventually I felt it sliding into the entrance to my throat.
    
    I hadn't quite conquered my gag reflex, but I was working on it. I kept the tip of the dildo in my throat, moving it back and forth slowly. I could take about 7" into my mouth and throat without gagging.
    
    I stopped and looked at my toys. They were good, but I wanted more. The two dildos were only 1" in diameter. I wanted bigger ones. I paused the porn and pulled my keyboard over. I went to the ...
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