One piece of information I didn’t expect to get in Dylan’s email collection was the user name my Mom used on Chat Avenue, the adult chat room where they apparently met. After I knew Dylan broke it off with my Mom, I frequently logged in as “Young Florida Stud” in hopes that I would find “Naughty FL MILF.” I figured if she was losing the guy she was fucking behind my Dad’s back, she may go back to the chat room to look for a replacement. This was a more fun alternative than simply presenting every bit of evidence I had against her to her face. If I could have a firsthand effect on her possibly cheating on my father, she would have no way out.
On a Wednesday afternoon, two days before my Dad was going to be leaving for Jacksonville for four nights, Naughty FL MILF finally arrived in the chat room while I was in there too. I had the day off from work, and if you had asked my Mom, she would have thought it was the last day off I had for the next six days. I told her I was working all weekend so that way if she did make plans with Young Florida Stud (me), she would think she had the entire weekend open. Little to her knowledge, she did not have the entire weekend open. I had Saturday, Sunday and Monday off, but she thought I was working 12-8, 3-11 and 12-8 those three days. And now that she was logged into the chat, all I had to do was secure a date with her and this fantasy would become a reality very quickly.
Once I saw she was in the room, I typed a message into the group chat to see if she would initiate a conversation:
“Looking for a horny mature woman to have a dirty chat with!”
I got a few replies right away, but none from my Mom so it didn’t really matter. I debated messaging her directly, but I thought that could come off as desperate. I figured I would at least give her a little bit of time in the chat room before I did.
Five minutes went by, then ten, and I was getting impatient. As I started crafting the message I would send to her, a message from Naughty FL MILF arrived. It was her.
Naughty FL MILF: Hey there, how are you today?
I momentarily froze. I knew I had one chance to make a good impression, otherwise I’d either need to register a new user name — along with a new made up email — or go back to my original plan, which was to just overwhelm her with all of the evidence I had piled against her.
Young Florida Stud: I’m not doing too bad, how about you?
Naughty FL MILF: Oh I’m doing fine. I’ve never seen your name in here before, are you new?
Young Florida Stud: Yeah this is my first time in actually. I had a friend tell me he actually met a girl in this chat and they started hooking up, so I figured it might be worth a try.
Naughty FL MILF: Sure why not? At the very least you could have some fun chats in here!
Young Florida Stud: Is that what brings you here? Are you a usual here?
Naughty FL MILF: Yeah I come in here every so often. Couple times a week. I’m generally just in it for the chat.
Young Florida Stud: That’s cool. So what’s your name? Where are ya in Florida?
Naughty FL MILF: Well since I’m married I shouldn’t give out my name right away 😉 but I’m in Fort Myers. How about you?
Young Florida Stud: My name is Derrick and it turns out I’m your neighbor! I just moved to Cape Coral two months ago. Small world, huh? Lol
Naughty FL MILF: No kidding! Where did you move here from?
Young Florida Stud: Just Orlando. My Uncle owns an autobody shop in Cape Coral, but he’s getting older so I’m gonna take over some of the day to day stuff and eventually run it myself.
Naughty FL MILF: Good for you! Is that what you did in Orlando?
Young Florida Stud: Yeah, after college I didn’t get a job right away so I decided to start working there, and I actually really liked it.
Naughty FL MILF: What was your major in college?
Young Florida Stud: I was a business major. So if I end up taking over my Uncle’s company it will come in handy.
Naughty FL MILF: For sure! How old are you if you don’t mind me asking?
Young Florida Stud: I’m 27 years old. Is it rude to ask how old you are?
Naughty FL MILF: Haha no I don’t take offense. I’m 56, I hope that doesn’t make you run away.
Young Florida Stud: No way. If we’re being honest, I love women who are your age.
Naughty FL MILF: Oh yeah? Why’s that?
Young Florida Stud: There is just something I find really sexy about an older woman who has enough confidence in herself to still go after younger guys and know what they want sexually. It’s just a huge turn on.
Naughty FL MILF: I can see that.
Young Florida Stud: But the question is, are you that kind of mature woman?
Naughty FL MILF: What kind of mature woman do you mean?
Young Florida Stud: The kind who knows what she wants sexually and isn’t shy about going after a younger guy?
Naughty FL MILF: Perhaps 😉
Young Florida Stud: Well now I’m very intrigued 🙂
Naughty FL MILF: Haha you should be!
Young Florida Stud: I’m gonna guess that that would be a very good description of who you are, but you are obviously being cautious because you don’t know me yet.
Naughty FL MILF: You’re a smart kid 😉
Young Florida Stud: Well thanks, but I’d like to get to know you if that’s a possibility.
Naughty FL MILF: I think I would like that too Derrick 🙂 My name is Anna
And from there my Mom and I continued to chat for the next two hours. About 45 minutes in I got her to admit that she had been cheating on her husband (my dad) recently. Fifteen minutes later we exchanged dirty pictures. The one she sent me was one of the same faceless ones she had emailed Dylan. The one I sent her was a picture of a random guys cock and abs that I found on a porn site. She was impressed. Minutes after that we exchanged face pictures. Her’s was her Facebook profile picture, and mine was the Facebook profile of a Friends Friends Friend who lived in Dallas. Again, she was impressed. A half an hour after that we were role playing a hook up. Ten minutes later we were making detailed plans to hook up, and as I expected, she was angling for it to happen this upcoming weekend because her husband would be out of town and her son would be working.
Saturday at 1 pm we would be meeting at the Publix supermarket that was ten minutes down the street from our place. Once we verified that it was each other from the chat room, I would follow her to the community she lived in, park in the clubhouse parking lot and drive with her in her car back to the house. From there we’d have multiple hours to have sex with each other before her son (me) got home.
She gave me her email in case I had to change plans. I emailed her Friday night with the same picture I had sent to her in the chat with a message that said, “Really looking forward to tomorrow. Here’s my picture again in case you forgot what I looked like. Send me yours too if you don’t mind!”
When I woke up Saturday at 10 am I had a message back from her with her picture attached … “See you in the bakery at 1! Can’t wait!” So when I left the house at 11:30 to go to work I could barely contain my excitement. I knew that in just a few short hours my Mother would be completely under my control.
I grabbed some lunch and then sat in my car in the back of the parking lot until 1 pm. At 12:50 I saw my Mom pulling in. She was wearing a white tank top that showed a fair amount of cleavage and tight jeans; it was certainly a more revealing outfit than she would wear out if she were going to the store with my Dad or myself.
I didn’t plan to go into the store and confront her there. There was too much that was out of my control in the store. I would let her walk around Publix for a while until she realized she was stood up, then I’d be waiting at home to confront her when she got back. As soon as she walked into the store I sped home so I could get everything set up. All of the emails she had sent Dylan were printed out. All of the emails she sent me, plus screenshots of our chat in Chat Avenue were printed as well. And of course, the video that Dylan recorded of him fucking my Mom in my bedroom would be ready to go on my bedroom television.
She must not have waited too long at Publix before deciding she was being stood up. By the time I parked the car down the street, ran back to the house and got everything set up, she was walking in the door, and she had no idea I was home.
“Sean, what are you doing home? Your car wasn’t in the driveway,” she said as she walked into the kitchen and saw me sitting at the dinner table. In front of me I had my laptop and a stack papers.
“Sit down with me Mom.” A look of concern came over her face, almost as if she were connecting all of the dots.
“Is everything OK Sean? Did something happen at work?”
“Everything is fine with work. I didn’t even go in to work today. I need you to come sit down though, alright?” She reluctantly approached the table and sat down across from me.
“What are all of those papers for?”
“On these papers are the emails you sent Dylan Burr. They include pictures you sent him, both non nude and nude, plans for when you two would hook up, and details about fucking in Miami.”
“Sean please –”
“Shut up Mom. You are going to sit there and hear what I have to say or all of this information is going to Dad and every other person you know. Understood?” She shook her head yes. “Every email you and Dylan sent to each other is included here. I watched you fuck him multiple times. There’s a crack in the blinds in the window in your bedroom. I stood outside the house and watched you two. One day I confronted him about it and he gave up this information very easily. He said he was just using you, and that he could find another middle aged woman to use in no time. But before he broke it off with you, he fucked you one last time … in my bedroom. I have it recorded. I have video of Dylan fucking you on my bed like a cheap whore. I can show ya the video if you want. It’s hooked up to my TV. Want to go watch?”
Tears streamed down her face as she shook her head no. I loved it, and continued:
“Also included are the emails and pictures you sent to Young Florida Stud, also known as Derrick, also known as me. You were talking to me, Mom. You sent naked pictures of yourself to me. And today you went to Publix to meet me. Of course, you didn’t know this. You wouldn’t want me at all involved in your sex life. But now I am involved.”
Until I mentioned that I would be involved with her sex life, my Mom wasn’t making eye contact with me as I spoke. Now she stared right at me.
“See at first, I was going to use this information to get as much money as I possibly could. I know you control just about all the money that Dad makes, and I was going to make sure all of what you take went to me. But then I watched you get fucked a couple of times, and as sick as it may seem, I enjoyed watching that. I’m not going to ask you to fuck me. However, I am going to now have total control of your sex life and anything I consider to be remotely related to it.”
She tried interrupting but I continued talking.
“Now if you decide you don’t want to do something that I tell you to do, all of these papers and the video of you fucking Dylan will be given to Dad and everybody else in our family. Both Grandmas, your brothers, your sisters, your godchildren, your cousins, your friends. I’ve made enough copies to send it to everybody you know and love. And same goes for if you, for whatever reason, decide to divorce Dad. All of this information will get to him, and he will use it against you to ensure that you will get absolutely nothing in the divorce.”
I was finally finished, but she remained silent.
“Anna, do you understand everything I said?”
She shook her head yes, but that wasn’t good enough.
“Use your words Mom.”
“Yes, I understand.”
“Good. Are there any questions you have for me?”
She shook her head no, but that wasn’t good enough.
“Words Mom.”
“No. Will you just leave me alone now?”
“I have one question, then I’ll leave you alone for the rest of the day. Why did you do it?”
“I don’t know Sean,” she quickly replied. That wasn’t going to cut it.
“Bullshit. That’s bullshit. This is all out in the open now, so just start being honest. Why did you do it?”
She took a minute to think about what she should say. She was obviously overwhelmed by everything that had happened.
“Well?” I asked.
“I just needed better sex, more sex. I have needs … I wasn’t trying to hurt your father, he just couldn’t satisfy me the way I need to be satisfied. I needed more sex.”
We sat there for a moment staring at each other. Her answer was honest, and basically what I expected to hear from her. I stood up and started walking toward my bedroom. Before I was out of the kitchen, I turned back toward her …
“Don’t worry Mom. Now that I’m in control of your sex life, you’re going to be having all of the sex you could handle. I’ll make sure you are being used like the cum-guzzling slut you truly are.”