1. Christmas Eve with Gloryhole Glenda


    Date: 1/11/2024, Categories: Fiction Blowjob Male/Teen Female Prostitution, Romance Transgendered, Author: Limnophile, Source: sexstories.com

    ... but I quietly said, “Shhhh. Let’s let him sleep.” I knelt and gently touched his dark hair, then closed the door quietly as we left the bedroom.
    
    She asked, “Do you want some hot cocoa? We have cocoa and cookies. And candy canes! Or do you like donuts?”
    
    I thought to myself, “And people wonder why diabetes is so common, and there’s a big obesity problem?”
    
    One night of indulgence wouldn’t hurt, so I humored the girl. “Cocoa and a cookie sounds nice.”
    
    I sat on the sofa and she brought cocoa and cookies. “The doctor says Dad needs these medicines. Thanks for the money. Now I can get them in the morning.”
    
    On the table I saw medical paperwork for a patient “Glen / Glenda Brennart. Gender: Other. Bronchitis and pneumonia...”
    
    It listed three medications, and I knew I had samples of two of them in the trunk of my car.
    
    “I need to get something, Cindy. I’ll be back in a minute.”
    
    I got the antibiotic samples from the trunk, and had a thought. It was Christmas Eve. Their computer was ancient, and I had just bought a new laptop as a gift to myself. My 3-year-old laptop at home still worked, and they needed the new one far more than I did.
    
    When I walked back in, I saw Glen was sitting next to Cindy on the couch, coughing into a tissue. Only one of his hands had the long purple fingernails. The other hand looked plain and masculine.
    
    Cindy said, “Dad, this is James. He gave me money, so we can get your medicine now!”
    
    I looked at Cindy, as I held a box behind ...
    ... my back. “I met Santa Clause outside.”
    
    Before she looked at the box, she said, “I’m not a little kid, I turned 18 last month. I don’t believe in...”
    
    I held out the box, and she saw the picture of the laptop and shrieked. “REEEEE! YES! THANK YOU!” She gave me a hug and happily put the box on the desk and opened it.
    
    I handed Glenda a plastic bag of antibiotic samples. “Take one of each of these twice a day. You’ll only need to buy this one.” I pointed at the bottom medication on the list.
    
    He objected between loud coughs. “We don’t take charity. I can’t accept this...”
    
    I said, “It’s not charity. Your blowjobs are amazing, Glenda. This is a tip. I hope you feel better soon. Have a Merry Christmas.”
    
    Glenda nodded as he coughed.
    
    A tear came to his eye, as he said, “Nobody wants to call me ‘Glenda’. Thank you!” He hugged my waist as he sat on the couch, then rested his cheek on the front of my pants. I remembered all the times I climaxed with his face the same distance from my legs. My penis surprised me by beginning to swell, and I gently pushed away.
    
    I handed Cindy one of my business cards and said, “If you’re having trouble and you think you need to do blowjobs for money, you call me first, okay?”
    
    She hugged my waist. “I will. Thanks! Thank you so much!”
    
    I reiterated, “Seriously, call me first. I’ll either help you again, or at least be a good customer.”
    
    She nodded. I was 32, and could barely believe I had just offered to pay a high school student ...
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