I figured I’d share with you guys one of my wilder sexscapades over the next few days, if folks are interested. The story of the Red Hot Summer involves a whirlwind of a FwB relationship with a stunner of a milf, and an even more wild fling that resulted from it. For now though just enjoy the opening story. Names have been changed for privacy.
This story starts a few years before it actually picks up. I was 16 years old, spending summer in the swanky vacation town that I stayed in each year, and decided to make a little cash on the side by mowing lawns and doing odd jobs. One family that I did this for were Martha and Todd. Todd was a bigwig finance guy who had more money than sense and enjoyed the finer things in life. Martha was a classy woman in her early forties who came from old money. The other thing about Martha was that she was absolutely smoking hot. Though she had some obvious signs of age she still had shoulder length wavy brown hair, a shaped ass that seemed to go on for miles when she was in front of you, and a pair of DDs that she either barely contained in a dress or covered with a swimsuit.
Now, that may be the obvious reason why I, a hormonal 16 year old virgin, tried to be extra nice to Todd and Martha, but the other reason was that they were huge, and I mean, HUGE tippers. I made more off their tips that summer than I did working retail during the school year. Because of their deep and generous pockets, I ended up doing a lot of odd jobs for them and ended up becoming kind of close to their family, despite the fact that their youngest kid was a few years older than me.
At the time, I obviously had the hots on for Martha, as did any man within a 20 mile radius of her, but I doubt she saw me as anything but the nice boy who mowed her lawn and helped her husband clean the garage and work on his car. I was still pretty scrawny and unconfident at the time, so I relegated myself to rubbing one out to her a few times when I got home from working for them.
After that summer I was mostly busy working internships and taking road trips with friends, much to Todd’s chagrin for the first two years after that. Following that however I lost contact with Todd and Martha, until I was a junior in college. After having a rough year mentally, and with the thought that I had already built up quite the impressive resume with or without another summer internship on the docket, I was looking forward to just lounging around on the beach and hanging out with my old friends for the summer. Naturally, my grandfather threw a wrench in this plan and told me about a week in that if I was going to stay in his house, I had to get a job.
Luckily, it didn’t take me long to find one, and about two days later I was working shifts as a lifeguard at the local club. As far as jobs go, it wasn’t bad. There was a chill shack where I could hang out with my coworkers, the hours weren’t awful, and I got free food and drink from the snack shack for lunch. Plus, multiple hot co-workers to flirt with.
On about my third day on the job, I was sitting in the chair when I felt a tap on my foot to get my attention. Standing below me was one of the most glorious sights I have ever seen. It was Martha, but at first I didn’t recognize her. While she had kept good care of herself while I knew her, she had clearly gotten into fitness and dropped several pounds. Her hair had been cut into a karen-esque but very hot haircut, and where before she had made a point to stay out of the sun to avoid burning, she had clearly either gotten a spray tan or had found some other way to get some color in her skin. She was wearing a blue bikini that was too small, but just barely tasteful
It took me until she said something along the lines of “It’s Martha silly boy” for me to recognize her. If I could have I would have jumped out of the chair. We got talking for a fair bit about what had been going on in our lives for the past few years. It was during this first conversation that I noticed our dynamic was very different to how it had been when I was 16. It was a combination of me being far more confident and outgoing, and a much more friendly vibe from her. Eventually I told her I had to work, to which she responded by giving me a playful slap on my thigh, before bringing her hand to her mouth and saying something to the effect of “You really filled out in college didn’t you.” I gave a playful joke back, to which she offered to give my new muscles an old use, and come mow her lawn again.
At this point, I wasn’t really expecting anything sexual, but the memory of just how much she tipped egged me on, so I accepted the job.
My next day off, I hauled my familie’s mower over to Todd and Martha’s, and knocked on the door of the house to confirm with them what they wanted done. The door opened to reveal Martha wearing another small bikini top and a thin, flowy skirt. She invited me inside, where we went over what she wanted done. I asked her if Todd wanted anything done while I was over, to which I learned that he was on an extended business trip. I would later learn that these business trips were essentially Todd and his buddies renting a mansion together down in the Carribean and enjoying life a little too much.
In any case, Martha told me she would be by their pool if I needed anything. As she spun to go finish whatever she was doing, she stroked her hand across my chest in a playful but not overly flirtatious way. I was lucky, or perhaps unlucky, that she didn’t turn around, otherwise she would have seen me starting to get a major boner.
Spurred on by this interaction, I dove into mowing like a madman. Partly because I was in better shape, and partly because of my “motivation”, I completed the lawn in half the time it had taken me in the past. Martha watched the whole thing from the pool, and gave me pointers here and there about how she wanted me to do things, as well as catching up on my life. When I completed, she called me over to relax for a bit.
I sat down on the chair next to her, and wiped my head with my shirt. Martha laughed at this and told me if I was really that sweaty I should just take a swim and then towel off. When I told her I wasn’t wearing trunks, she just laughed again, said she knew, and that she didn’t have a problem with me swimming in my undies.
It may have been me being a little dense, it may have been me not truely seeing Martha as attainable, it may have been genuine respect for Todd, the man who funded my first big computer project and taught me to change a cars oil, but until that point I had thought I just misinterpreted signs. With that line though fireworks went off in my brain.
I quickly stripped down to my undies, and dove in the pool. When I surfaced again, Martha had seemingly vanished. At first I thought I had just suffered a hallucination from dehydration, but after a minute or two Martha reemerged from her house carrying two glasses of coke. She slowly entered the pool down the stairs and placed the glasses to her side, gesturing for me to come over. She giggled and apologized if I liked rum in mine, she figured it was better to play it safe. I told her that I didn’t mind having some in the future as I reached for my glass.
She had positioned herself between the glasses perfectly so I didn’t realize. By the time I had my hand wrapped around the drink, her ass was pressed firmly against my crotch. A little shake was all it took to get me going, and upon feeling the “growing connection” between us, Martha pulled back and gave me one of the dirtiest looks I’ve ever gotten. I took a deep sip of my drink as she pulled her ass back, and turned to face me.
In one move, she took a short stride over to me, cupped my growing erection, and downed her drink. Smiling, she began to rub me through my undies and told me with that same classy smile “Well, if this has grown as well, I’ll be very impressed.” I asked her if she had really noticed me before, to which she giggled again before grabbing me firmer “Sweetie, I noticed all of you teenagers staring, but you always did have a little something extra.”
She continued to rub me through my pants, and to be honest, with how long I had been staring at her that day, the heat, and just how damn hot the situation was, I was getting close. She must have realized this and fished my dick out of my undies to start giving me real strokes.
It started with long ones with just one hand, but she quickly moved to using both her hands and giving me twisting strokes. I lasted maybe another two minutes before I released a big nut into her pool. Martha once again giggled at this, pulled me in close, and whispered in my ear “Good boy.” before pulling me into a kiss. She then pulled out of it and walked back out of the pool, sitting down on the chair once again.
We went back to sort of awkwardly chatting as I towled off and put my shirt and shorts back on before Martha asked me if I enjoyed her new kind of “tipping”. If I didn’t we could go back to the old way, but she didn’t know how many jobs she could afford with it. I eagerly answered that the new way was better, to which she smiled, stood up, gave me another kiss, and told me to be ready for a call, before walking inside and leaving me to wheel my lawnmower home.
Source: reddit.com/r/gonewildstories/comments/ht8i2k/my_red_hot_american_summer_mf
Damn, excited for pt 2