1. Christmas Eve with Gloryhole Glenda


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

    ... I suck you right before? Then you can just do what you need to, without taking a long time to get ready?”
    
    “Uh … I guess.”
    
    Cindy stood up as she asked, “How long until the pill starts to … WOOHOO! I’m swimming!” She flailed her arms around and I caught her as she started to fall over.
    
    I laughed. “I’m pretty sure it’s working.” I carried her to the bed and helped her undress, then took my pants off.
    
    Cindy asked, “How can I help?” She tried to get up and failed.
    
    Glenda told her, “Just lay still, sweetie. Everything’s fine.”
    
    For the first time, I watched Glenda lick and suck my penis. I wasn’t attracted to his face or body at all, but I could tell he loved me, and loved his daughter dearly.
    
    The thought that he loved me and trusted me to take his daughter’s virginity touched my heart. Imagining how great it would be to fuck a tight, pretty virgin made me hard enough to drive nails with my penis. I pulled out of his mouth and he quickly rolled a condom on me. As I crawled on top of Cindy, he held one of her legs to make it easy for me to get myself lined up.
    
    I kissed her lips and Cindy groggily said, “This is nice, but I thought sex would feel better.”
    
    I looked into her dilated and glassy eyes. “I didn’t start yet. I’m sorry, but this will hurt for a little while, then it should feel good.”
    
    Glenda smeared some extra lube on the condom and stroked me a few times, then I thrust into Cindy.
    
    I expected a scream, but instead she just said, “Uhhh!”
    
    I ...
    ... felt her hot, wet snatch squeezing my cock tightly. Even with the condom, it was excellent!
    
    I held still inside her and nervously asked, “Are you okay, Cindy?”
    
    She made her father and I laugh with, “I thought it was supposed to hurt. That felt like a big, backwards fart.”
    
    Glenda and I laughed, and Cindy wondered aloud, “What’s so funny?”
    
    Glenda said, “We’ll tell you later. I’m so glad you’re okay! I was really worried!”
    
    I said, “Thanks for the help, but I think we’re all right now. Would you mind leaving?”
    
    He chuckled, “Sure. Sure.”
    
    -
    
    We had agreed that after Cindy’s first time, I wouldn’t see her again for two weeks to avoid her getting overly attached to me, and I would only have sex with her again if Glenda agreed.
    
    For the two weeks, I returned to getting anonymous blowjobs at the gloryhole, paying Glenda each time, until I went back to mostly 69 with Cindy.
    
    She seemed even more clingy than before, and several times she started to say, “I love you” and stopped herself. I didn’t want her getting too attached, so I went back to the glory hole and only visited their place when Glenda was there. One night Cindy was standing in the parking lot by the gas station men’s room, a few steps from where her father had sucked me off hundreds of times.
    
    She started to cry as she asked, “What did I do wrong? Why are you mad at me?”
    
    “I’m not mad. I still like you, but I don’t want you getting hurt. We make each other feel good and I help your family out, ...
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