1. My Mom's Secret, Part 3: Planning The Blackmail


    Date: 5/16/2018, Categories: Fiction , Blackmail, Oral Sex / Blowjob, Cheating, Mature / Older, Mature / Older, Wife / MILF, Author: badson, Source: sexstories.com

    fucking?" He again took a second to think. "How much money am I getting for doing all you asked me to do?" "Video included?" I asked. He shook his head yes. "Five thousand dollars, half when you give me all information, half after the video is recorded." "Oh wow! I was expecting you to say like 200 bucks. Yeah, I'll definitely do it for five thousand." "Ok good, so what happens after you met in the chat room? You just started fucking right away?" Now that he had committed, I couldn't wait to ask him questions. I had to know how all of this started. "Well we met in the chat room and we realized we lived close to each other, but for a few weeks we just talked online, exchanged dirty pictures but we didn't hook up. She was afraid to. But then she told me she was going to Miami for a weekend and that I should go get a room and we could hook up there." It was then that I realized my Mom and Dylan had been seeing each other since January. At the end of January my cousin had a bachelorette party in Miami "So wait, this has been going on since January?" "Yeah. She said she was going to be in Miami for a Bachelorette party or something. So I went the same weekend, got a hotel room a couple blocks from where she was staying and then she came there both nights to see me. Then once we got back here we just kept hooking up." "Ok, so have you been emailing or texting or just chatting in the chat room?" "Emailing. She said she had an email address that nobody knew about. Plus she said ... texting was too risky." "Do you still have those emails? Is there anything revealing or compromising that you have?" "Yeah, nude pictures, your work schedule, your dad's work schedule, messages about meeting up in Miami." "Ok, I need you to forward me everything you have that she sent you. Do the nude pictures she sent you have her face in them?" "Only one. I told her that I wouldn't meet up with her in Miami if she didn't have her face included in a naked picture. But I have a lot of topless and pussy pics from her too, they just don't have her face." "Alright, I need those." It seemed like Dylan was starting to feel weird about this. He was suddenly involved with a woman whose son was desperately trying to get nude pictures of her. I had to assure him this wasn't sexual, even though it was. "Listen, this is about blackmailing her and nothing else. I'm not some weird perv who is trying to fuck his own Mom." "I don't judge man, money is money. I don't care what you do with what I tell ya." It was good to hear that this was his stance, but I still didn't want him to know I was in this to eventually become my Mom's pimp. "Do you care if I ask you why you are fucking her? I mean, you're good looking and young. Why someone so much older?" "Honestly?" I shook my head yes, I wanted to hear the truth. "I just have a thing for trashy looking older women who are still kinda hot, but look like they were really hot twenty or thirty years ago. They're nasty in bed and desperate for young ...