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He really isn’t interested in finding a job, although he will grudgingly do yardwork from time to time for generous neighbors. But still, he is always on the prowl for money, ideally money that takes very little work to obtain.At a mutual friend’s game night one evening, Jake mentioned to me that he could use a little extra pocket money. It was a private conversation but I thought at the time there was more to it than there seemed to be. Well, there was. I’m not rich, but I am a comfortable older gay man. At 57, I like to think I’m pretty good looking, but even so, I know when guys as young as Jake bring up money around me what they are really looking for is some kind of handout or loan.When Jake finally made his proposition to me, he stated upfront there was no negotiation. I was a little surprised. He made very clear what he was willing to do. And he made very clear all he wanted was $30 a session. I thought that wasn’t enough, and tried to tell him so. But he wouldn’t discuss it.. I found myself wanting more after a little while, I found myself wanting something bigger inside of me. As the thought entered my head, I found myself walking back into my parents room, and next thing I know, the big white dildo is in my hands. I knelt down again and lubed up the white dildo. On my knees, I rubbed the toy against my whole, before pushing it in. This feeling was a little more intense than the feeling of the green dildo in my butt. This one hurt, it hurt bad. I felt spasms of pain roll through my body from my rectum. I pulled the dildo out and started to breathe heavily, my butt still hurting. Determined, I tried again, this time, the pain a little less, but still enough to make me pull the dildo back out. This went on for a few minutes, me pushing the dildo in, feeling the pain, then pulling it back out, until finally, I could take the pain, and left the dildo in. After awhile, it felt glorious, the dildo penetrating me deeper than before. I pushed in as.
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