A 10-Part story about a son's fantasy, a mother's betrayal, and a secret that the two would share.
After our encounter with Jared, my Mom and I agreed that we would stop looking online for guys she could hook up with. We had exhausted just about every online option, and plus, there was more risk talking with guys online and passing pictures of her around than either of us ideally wanted. Though our motives were different, this was something we both wanted to continue with. My Mom didn't want to get caught because it meant her home and my Dad's money would be gone in the blink of an eye. Not to mention she'd be looked at as an embarrassment by the rest of her family. I didn't want her to get caught because I knew my leverage would then be gone.
Additionally, I eased off on the pressure for the next few weeks because I knew we'd have an opportunity to get my Mom fucked coming up. In the middle of July my Dad would be taking a week long trip to Jacksonville for the opening of a new car dealership that his company had established. Since he was the manager of a Ft. Myers dealership, they wanted him to be there during the opening week to make sure things ran smoothly. And with very little convincing, I made sure that my Mom was prepared to tell my Dad that she wouldn't be joining him out of town.
My Dad left for Jacksonville on Friday July 8th and he wouldn't be back until the following Friday. While he was there working 14-16 hour days for a week straight, my Mom and I would be spending his money on food, drinks and a two-bedroom suite at a hotel in South Beach that would be our home for three nights. Miami presented us with the opportunity to meet a bunch of young, good looking, horny guys who would be interested sticking their dick inside an eager MILF.
The morning after my Dad departed, my Mom and I too left for the opposite coast. The drive over was mostly quiet for the first hour. Even though I had already been in the room with her as she gave head once, there was still some uncertainty with how a long weekend together would go, especially since the objective was clear: We wanted to get her fucked as much as possible. After about an hour of trying (and failing) to make small talk, I figured I would try to address the situation.
"So listen, I know this is still sort of weird for you, but this weekend doesn't need to just be about finding guys. We could hang out at the beach, we could go out for nice dinners. This could be a really fun weekend away." I said to her. She took a drag off of her cigarette and continued staring out the window. Needless to say, I was very pleased that as soon as my Dad left for Jacksonville she swapped out her E-Cigarette for the Misty 120's she loved for so long.
"I know," she replied after a few seconds.
"I'm being serious! The majority of the time you won't even be thinking about guys. Just think about South Beach, sunshine, the best mojito's in the world, delicious Cuban food, more Mojito's!" I said with some enthusiasm and a laugh. She responded to my attempt with a smirk.
"We've talked about this a lot ... what's still bothering you Mom?" I asked.
"I guess I still just don't get why you're doing this. Like what are you getting out of it," she answered. I knew I had to be somewhat delicate with this answer, but I also couldn't tell her a complete lie.
"Alright, I'll be totally honest with you right now, OK? It's obviously not a secret that you're a very good looking woman. All throughout school you were the best looking Mom of any kids in my grade, or any of the guys I hung out with. It was never a sexual thing, but I can't act like I haven't ever noticed how, um ... attractive you are. Now when I saw you and Dylan having sex, I was so mad at you. I hated you. But at the same time, I loved seeing you like that. You looked incredibly sexy and it was like you were in your element. You were doing exactly what you were meant to do, and it was like you were loving any minute of it. But I felt like I couldn't just let you get away with it. I couldn't let you do it behind Dad's back, or my back. So I thought about it for a few weeks, and I decided this was best."
"That actually kind of makes sense," she replied. I couldn't believe she went for it. She seemed pleased with my answer. I had no clue to what to say, so I just said ...
"Mojito's!" For the first time in the entire car ride, she laughed and legitimately smiled. Things were good.
Things were even better once we got up to our hotel room. I hooked up the blender and made us each a drink to sip on as we got settled in. About a half an hour later we were ready to head down to the beach for a couple of hours before we went to dinner. For the most part, this felt like a very normal trip; a weekend getaway we would take even if I weren't essentially trying to pimp her out. For those few hours on the beach and at dinner, she was completely relaxed and at ease with me and the situation. I had lulled her into a false sense of security ... and that was necessary.
After a nice Italian dinner we retreated back to our hotel room to develop a game-plan for the night. To my surprise, my Mom had some well-thought-out ideas about the evening.
"Listen," she said as we sat down in the common area of our hotel suite. "I know you want to be a part of this, but I don't think it's going to work if you're hanging around when I'm trying to talk to guys."
"Well that's the whole point of this, isn't it?"
"I get that, but think about it this way ... say you were out at a bar and an attractive older woman came up to you, and then she said that she wanted to have sex with you, but she wanted her son to watch, and she pointed over toward son guy in his mid-twenties sitting at the other end of the bar. What would you do?"
"Well first of all, that's not how we'd do it. Second of all, if she was hot enough I absolutely would fuck her. And you're hot enough."
"I just don't think it's going to work Sean. I mean, if you want to go out and waste our time, we can."
"Well I didn't come to Miami just to let you go out alone and fuck whoever for three nights." After I said this I realized how upset I was getting and knew I needed to tone it down. "I think we should just give it a try."
"I said I was fine with that, I'm just skeptical that it will work out the way you are thinking it will."
"Well it definitely won't if you approach a guy so directly about what we want. Don't you know how to flirt?"
"Of course I do."
"Well you're gonna be out there with your tits pushed up and some cleavage showing, tight ass jeans and some slutty make up ... do your thing and some guy will be all over you."
"And what will you be doing?"
"I'll be sitting at the bar next to you. We'll just be a normal mother and son out at a bar having a drink or two. We'll position ourselves so your next to a guy, or guys. You can flirt, I'll mind my own business when things are picking up. And then when you have an opening, you can let him know the situation."
She was reluctant to go along with the plan, but finally she agreed. She dolled herself up, changed her outfit into something a bit sluttier, and we were ready to go out. After first stopping for a frozen daiquiri at Wet Willie's, we settled in at a semi-popular South Beach bar and it was a busy night Friday night crowd. I noticed a favorable ratio of men to women, so I thought that it was possible this might be the place we find a guy for my Mom for the night.
You know that thing "Mother's Intuition?" Well I don't know if this is the best example of it, but my Mom was absolutely right about my plan not working. Despite how good she looked, there was very little interest in a mature woman who was occasionally making casual conversation with a younger guy sitting next to her that was likely her son. And the one time she actually talked with a guy long enough where there was some traction about hooking up, he wasn't shy about telling us both how fucked up we were.
It was a frustrating night for both of us, but even more so for me since my Mom wasn't hesitant about telling me "I told you so." Before we went to bed we agreed we'd revamp our approach before we went out again the following night.
We spent the next day at the beach and did our best to avoid talking about what had happened the night before. I couldn't help but notice how many eyes were on my Mom, who was in a much skimpier bikini than she was yesterday, and a far skimpier bikini than your typical 56 year old would be wearing while out with her son. I wasn't complaining though. It would've been fine with me if she met a guy out then, but again, her concerns seemed legit ... it would be very difficult for us to find a guy out at a bar if I was tagging along.
To my displeasure, we agreed that I would only watch from a distance. As much as I would've loved to have been up close and personal, there was something erotic about simply observing and wondering what was being said. She looked so sexy and slutty, and even a little desperate sitting at the bar alone, chain-smoking her Misty 120's, flirting with guy after guy. Multiple guys passed by, talking with her for just a few moments, one single drink, before moving on to the next bar or the next girl.
Finally, after a couple of hours and one bar change, Mom found her guy. From 20 feet away he looked like her type ... around mid-20's, tall, athletic build. He was with two other guys, but neither of them were paying attention to her. Small talk slowly developed into some laughing and flirting, which eventually opened the door for some innocent thigh and arm touching.
At one point my Mom went to the bathroom, and I saw her prospective fuck laughing and high fiving his friends. I assumed it was in relation to her, and I had to find out. I casually strolled over to order myself another drink, and the first thing I had one of his friends say was, "I bet she takes it in the ass." I had to interject.
"Are you talking about the older lady?" I asked. They looked at me like I was crazy. "Sorry, I overheard you say 'I bet she takes it in the ass,' and I noticed how desperate she seemed talking to you."
They began laughing.
"Yeah man, we were." His friend said.
"Nice, have fun with that. Older broads like her are usually sluts." I replied.
"Yeah, that type isn't for me, but my man here has a thing for trashy old hags," he said laughing, gesturing to his friend.
"Oh yeah?" I asked.
"Yeah, I just like beat-looking mature bitches. They are filthy in bed ... especially the married ones, ya know?" He answered. Amazing, that was almost word for word what Dylan had said about her. The bartender brought over my drink, and I figured it was best to dismiss myself.
"True, true. Alright man, well have fun. Cheers!" I said to him as I began walking away. I sat back down and tried to act like I wasn't staring at them for the next fifteen minutes or so. At that point, Mom and her fuck buddy for the night left his friends behind and disappeared into a crowd.
A while later I walked back to our hotel but my Mom was nowhere to be found. It was around 2 am when I got back, but it wasn't until 8:30 that my Mom walked into our hotel room.
"Oh shit, sorry for waking you up," she said in a loud whisper as I sat up in the bed when she walked in.
"Nah, it's fine, don't worry about it." I answered. "Did you have fun?"
"Yeah, I did. He was really good. But I'm exhausted. I only slept a couple hours."
"What all did you do?" I asked her.
"I started out by blowing him for a little bit and then we had sex, and then we did anal. Luckily he wasn't quite as big as Dylan, so it didn't hurt so bad," she answered so casually, it was kind of shocking. "I'm gonna shower and then sleep for a bit before we go to the beach, OK?" she asked me. I shook my head yes.
"I can't wait to go out and find another guy again tonight," she said as she walked into the bathroom.
I laughed a little to myself, thinking about what this guys friend said at the bar. He was right about my Mom being an anal slut. But for the first time in a while, I was pissed off at my Mom. I was pissed that once again, she was going into business for herself, being a slut without my control. I wasn't going to let that happen again tonight. I had other plans.