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Christmas Eve with Gloryhole Glenda
Date: 1/11/2024, Categories: Fiction Blowjob Male/Teen Female Prostitution, Romance Transgendered, Author: Limnophile, Source: sexstories.com
... she wanted more. - On one visit, Glenda was at the apartment alone. He said, “I have some medical problems, and need a few expensive tests done. I’m terribly ashamed to even think about this. If I didn’t need the money so bad …” I put a hand on his shoulder. “It’s okay. Considering all I’ve done with you and your daughter, I think you can tell me anything, right?” He smiled sadly a moment. “You’re a good friend. A long time ago, we talked a little about Cindy selling her virginity. I don’t really like the idea, and I wouldn’t trust anybody else with her. I didn’t say anything about being sick or needing the money, but Cindy told me she wants to make love to you.” He let out a big sigh in resignation. “I know it’s a lot, but I need seven thousand. Is there any way you can…” I took out my checkbook and started writing. I said, “I know you’re worried about her safety. I’ll do it with her while you’re in the other room, so you can know she’s safe. You know that losing their virginity always hurts girls the first time they make love? I’ll try to make it as easy as I can for her. She’s pretty and I want to have sex with her, but I want to know my friends are both okay too.” I patted his shoulder and Glenda hugged me as he cried. “Thank you.” After a long hug he said, “Screw her, but don’t make love to her. I don’t want her getting the wrong idea. Don’t let her think you love her unless you really do. And …” He hesitated a long time. “And I don’t have ...
... any family but Cindy, and not a lot of friends. Just in case, could you sign something?” He brought out a will. “If anything happens to me, I want to know Cindy will be taken care of. Would you please?” “I … uh … I don’t know anything about raising kids. I don’t think I can take care of a kid!” He chuckled to himself. “It’s not like she needs bottles and diapers, she graduated a few months ago! If you can fuck her can you at least let her stay with you, and give her what she needs?” I chuckled too. “Yeah. I guess I can do that.” He had a serious look in his eyes as he said, “But don’t tell her you love her unless you really mean it. Don’t break my baby’s heart!” I had a lump in my throat. “No. Never.” - The virginity removal was almost clinical. The three of us sat in their living room talking. I handed Cindy two pills. “This one will reduce the pain a lot and the other will slow the bleeding, so that won’t be bad either.” She swallowed them and washed them down with some water. I said, “Both of you know the first time I enter her, it’ll hurt. She might yell from the pain, but don’t worry. It only hurts a lot the first minute or so. Everything will be okay.” Glenda held Cindy’s hand. “I’m so scared for her. Would it be too weird if I watch?” Cindy said, “Really weird! But … if James is okay with it, I guess?” The two of them looked at me. “Uh … I don’t know if I can do it with your dad watching. Uh…” Glenda suggested, “How about if ...