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

    For the next three weeks I allowed my Mom to continue her affair with Dylan. I only watched them twice more, but there were nine occasions in total during those three weeks that there was at least a four hour period where my Mom and Dylan could have been alone in the house, so I assume they saw each other more than just those two times. In those three weeks, I came up with and began conducting my plan to blackmail my Mom. I contemplated trying to set up a hidden camera in the bedroom myself, but I thought it involved far too much risk. I also figured that the greatest asset I had was Dylan; there was no way that a young, good looking guy like him could possibly actually have feelings for my Mom. I had $5,000 in the bank saved specifically for a trip for Amanda and I to take together ... now that we were broken up, that four grand could be used elsewhere. I figured Dylan would be able to tell me exactly how they met, how this thing progressed and how they stay in contact, since I wasn't able to find any messages from him on her phone, nor did she have any emails from him in her email inbox. Plus I could use him to eventually record her in the act, which would be the best bit of proof I could have over her. I just needed to hope that he was willing to be paid off. In just two weeks my father would be going away for four nights to Jacksonville. The co-owners of the car dealership he managed were opening a new store in Jacksonville, and they needed all of the GM's from around ... Florida (the ones from Orlando, Tampa, Fort Lauderdale, Fort Myers and Tallahassee) there for a long weekend. He would be staying there for four straight nights without coming home in between, so I knew that if things blew up when I revealed to my Mom that I was going to blackmail her, this would be a good weekend to do it. I also had a hunch that she would be eager to get fucked as many of those days as possible, which was something that I planned to use to my advantage. So on a Monday afternoon when Dylan was again fucking my Mom, I had lied about going to work that day and planned to confront him in the parking lot and make him an offer. This time, unlike the previous two times, I knew exactly what I wanted to say to him. Unlike the times before, I didn't go to the house to watch them this time. I didn't want my thoughts clouded when we talked. I wanted as clear of a mind as someone could have in a situation like this. At around 4 pm I saw Dylan walking back to his car in the parking lot of the clubhouse in the gated community we lived in. As usual, he was in no rush. He had just been completely fulfilled sexually (surely more than once) and he must have known he had given my Mom the best sex she could imagine getting at this point in her life. I was parked in the spot right next to him, so as he started opening his car door, I got out and said ... "Hey Dylan." He turned around quickly, and I could tell I startled him. "Hey, do I know you?" He asked. Of course he did. I could ...