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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
... for sex. I told Glenda, “I won’t see you in the bathroom in a few days, because I’ll be in the other stall. Take care of yourself.” He sounded like a sick frog, saying, “Thanks!” I checked every night, and the restroom was empty five nights in a row. On New Years’ Eve, Glenda gave me another wonderful blowjob through the hole in the wall. I started the new year squirting my sperm into an ugly man’s mouth, but it felt great. I tried hard to be happily ignorant again, imagining Glenda looked like Taylor Swift but with bigger tits. - CHAPTER 2 - One Saturday morning in February I got a call and sleepily answered. “Uh, hullo?” A gravely man’s voice said, “I can do something special for you. I need money to get my car fixed.” On my alarm clock I saw it was 6:04 in the morning and I had stayed up late the last night. I asked, “What do you mean? Who is this?” “It’s Glenda. I hate to ask you for anything, but without a car…” I’d been paying Glen / Glenda for blowjobs at a gloryhole occasionally for about half a year. He continued, “I wouldn’t ask, but I need six hundred by Monday.” I was nervous about discussing it over the phone. “How about I meet you for lunch at that pizza place down the block from your apartment? Noon?” “Sure. See you then.” I was happy I could get a few more hours of sleep. At mid-day, we ate our pizza at a table in a corner, quietly discussing things. I asked, “You need six hundred? What were you thinking of ...
... doing for that much?” He whispered, “If you use condoms and lube, I’ll let you do my butt. Two hundred each time?” I had never even fantasized about doing anal with a woman, much less a man as unattractive as Glenda. Still, I wondered what it would feel like. I figured that since he had given me a lot of happiness with his mouth, it would be worth a try. “Okay. I’ll go to a pharmacy quick and meet you at your place.” He said, “Cindy’s at a friend’s house. I don’t mind if you think about somebody else while we do it. Thanks again.” He shook my hand with his much larger one. I bought lube and condoms at a drugstore and walked up the stairs to his little apartment. He laid on his belly on the mattress and I lubed us up. I tried slowly inserting my dick in his ass, but it would only go in a couple of inches without hurting him too much. He said, “I think the angle’s wrong. Let’s try it leaning over the couch.” I put some more lube on us and tried it. I still had to go slowly and carefully, but was able to fit most of my cock in his ass. “Ungh! That’s not so bad, James. Go slow, but you can try fucking. Slow, okay?” “Sure. This feels really great! So tight!” I slowly slid in and out, over and over. I picked up the pace as I got closer to a climax. I closed my eyes and imagined I was doing it with a beautiful redheaded woman. “It only hurts a little bit. Keep going.” I thrust into his butt faster and faster, more and more, until I was there. “URRR! ...