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 see it all over his face.

“Not really, but, well, I don’t really know how to say this, but I’m Anna’s son. And I know you are having sex with her.” As I said this he got into his car and quickly shut the door, but I wasn’t going to let him drive away from me. Without even thinking, I shut my door and immediately opened his front passenger door and sat down.

“What the hell do you think you’re doing?” He wasn’t so much angry as he was amused and mildly annoyed by the situation.

“I shouldn’t have just gotten in your car, that’s my bad. But look, I couldn’t let you leave. I needed to talk to you about this.”

“What exactly is there to talk about?”

“Well I’m not angry with you or anything.”

“Thank goodness,” he said sarcastically.

“Look, I just wanted to know how all of this happened. I walked in and heard you guys a few weeks ago. I’ve seen you come here a few times since then. I just want to know how all of this went down. And I’ll give you money if you can tell me.”

He seemed intrigued by the idea of getting paid, but as I expected he would be, he was still suspicious about the whole thing. I continued:

“Listen man, this has nothing to do with you. It has everything to do with her. I’m not trying to get you in trouble, and if you have a girlfriend or wife I’m not going to tell her.”

“How did you know my name,” he asked. I had to think on my feet.

“The first time I caught her with you I was in my bedroom when you were leaving. I heard her say your name. And since then, a few times on days when my father and I were both working late, I know you’ve come and visited her. I’ve lied and told her I was working on certain days and waited for you to pull in here. I’ve contemplated confronting you a few times before, but I didn’t know exactly what I would say or what I wanted. Now I know.”

“And what is it that you want?”

“Does it matter if nothing is going to come back on you? Like I said, this isn’t about you.”

“I guess it doesn’t, so then what would you need me to do? And more importantly, how much money would you be giving me?” He was in now. As soon as he started talking money, I knew he would be locked in.

“Well let me ask ya, ballpark figure, what would you need in return for all information about how you met, plus how you keep in contact, plus your willingness to record you and her fucking?” As I said the last bit, he started laughing.

“I’m not really trying to end up all over the internet man.”

“I swear to God nothing will get on the internet. And you wouldn’t need to set up a camera or anything. All you need to do is take her into my bedroom to fuck her. I’ll have a camera set up and recording, just don’t draw attention to it.”

He took a minute to collect his thoughts and consider everything I had told him.

“Dylan, just tell me this, how did you two meet,” I asked. I didn’t want to lose him without getting any information.

“Online,” he replied quickly.

“Like a dating site?”

“No, an online chat room.”

“Ok, so you meet in a chat room and then start 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 dick. Anna isn’t the first one I’ve had. But this … you … this is a first.” I couldn’t help but laugh, he did too.

“Can I give you my email address and get the messages?”

“Sure, when do I get my first twenty-five hundred?”

“When are you seeing her next?”

“Friday afternoon.”

“Alright, I’m actually working that day at noon. If you wanna get here at like 11:30 I could give you the cash then as long as I have the emails first.”

“Works for me,” he replied.

“And I’ll have the camera set up that day too. All you’ll need to do is bring her into my bedroom and fuck her on my bed.” Dylan seemed baffled by this plan.

“Are you sure man?”

“Yeah, I’ll have the camera set up. Don’t worry about hitting record or anything like that, I’ll have it rolling. Just try to fuck her in there first, just in case the camera runs out of battery. After that, once I see it’s recorded, I’ll email you a time and a place to meet and I’ll pay you the other half.”

“Ok, I can work with that.”

“Glad to be doing business with you,” I said as I held my hand out. Reluctantly, he shook my hand. We had an agreement. I started to get out the car, but had to make one final request. “One more thing … this Friday has to be the last time you see her. I’ll give ya an extra one thousand if you can agree to that.”

“Man, you must be made of money,” he said as he laughed. “Yeah, I’m alright with that.” I gave him my email address and took his down too and then we went our separate ways for the night.

Later that evening I checked my emails, and sure enough, I had dozens of unread messages. He forwarded me all of their messages from when they first met online back in January, which included five faceless naked pictures, plus the one he mentioned that included her face. There were messages with their hotel plans for Miami and messages that talked about how much fun they had there. Then there were the messages where my Mom gave Dylan our address and instructed him exactly where to park and walk. All kinds of messages with mine and my Dad’s schedules. This was all the proof I needed. But of course, a tape of her getting fucked would put it over the top.

Dylan proved to be a man of his word. Friday night when I got home from work, before I even started the video, I knew they must have fucked in my bed. The comforter on my bed was freshly washed, as were my pillow cases and bed sheets. After I noticed it, I asked my Mom why she decided to wash my entire bed set without asking me. She quickly replied that she was “in a mood to do laundry.” How pathetic.

Of course, that isn’t what really happened. What really happened was Dylan fucked all three of my Mom’s holes on my bed, and when he finished on her face a good amount of his jizz sprayed on my comforter and pillow. It was quite humorous to watch my Mom first instruct Dylan to run to my bathroom and get a towel to clean herself off with, then panic because his cum was all over my bed, and then realize she would have hours before I got home to wash everything and get rid of the evidence. She requested they go to her bedroom for the next round and Dylan obliged. He had done the job I asked of him.

I got in touch with him and thanked him for helping me out. I let him know that I wasn’t working on Sunday and would get him the rest of his money then. He told me he was good to meet on Sunday afternoon, and he forwarded me the message he sent to my Mom calling their affair off. It was his way of reminding me that I owed him an extra thousand dollars. It was money well spent.

So on Sunday afternoon I met Dylan with $3,500 in hand and forked it all over. He assured me that he wouldn’t see my Mom again or let her know that I knew about their affair, and I made a promise that he and my Mom wouldn’t end up amateur porn stars. It was tough to stomach giving away that much money, but I knew that my Mom had a separate bank account where she stashed away money that my Dad gave her “for allowance.” That bank account, and my Mom’s sexual decisions for the rest of her life would be mine soon.

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