Summer was coming to a close, and Jason was about to start his final year of high school. All his life he had let his neurotic over-analytical nature control how he interacted with people. He had always put too much thought into everything, and as such had wasted his childhood. He believed he was unpopular, and therefore he was. With the social experience he had gained over the summer however: after having turned 18, going to parties, and fucking a busty young mall rat senseless, Jason was ready to improve his social standing. Life was finally a game he was ready to play.
But his senior year of high school had not started yet. Amy, his younger step-sister, REALLY wanted to go to a concert in the park, adjacent to college campus. It took some convincing, since Jason had zero interest in the boy band that was playing, but there would likely be a ton of girls there, he didn't have anything better to do, and he might as well try to get along with his newish step-sister and her friends.
Jason was not the only chaperon for the group of girls, but he was the only male one. The other three were moms, and two of them were kind of attractive, although only one of them was a MILF, per say. Her name was Melanie, and she was this smoking hot woman in her early forties. The kind of woman Jason had downloaded plenty of pictures of. Tall, thin, and busty as hell. She was built like someone who could handle herself in a fight, and clearly had a dominant personality. She was Becky's mom. Donna came in second on looks. She looked like a regular housewife, roughly around the age of 35. She had wider hips, a nice chest, and a little bit of an ass, but she wasn't chubby by any means. The last of the women, Hylan, was kind of on the large side. Not that Jason was above overweight women, beggars cant be choosers, but she just wasn't specifically an attractive woman by any means. Not in a fuckable way.
He had been ready to loose his virginity since birth, and now that he had he was ready for more. As the girls ran this way and that, He and the three moms sat towards the back of the roped off area. He spoke with them as equals, and they treated him as such.
The two of the women, Hylan and Donna, were flirting to tease him, Jason soon figured out. The more attractive of the three wasn't flirting specifically, but she was certainly friendly enough.. They had to know that he was only in high school, so they had to know that he was only 18. Still, he enjoyed all of the casual touching that went on while they spoke. They had arrived before Jason had, and had already had a couple of drinks. It wasn't too long before Jason was able to take a few sips for himself, and not too much longer before they offered to buy him his own.
Things went so well that Donna actually offered him a job. She was a manager of a grocery store, as it turned out. They exchanged numbers.
Still, it became apparent as the second band took the stage that the women were just flirting for the sake of flirting, and he didn't have any real shot of hooking up. At least not that night. Jason grabbed his third beer and told them he was going to "make his rounds". He got up and wondered the crowd looking for a potential hook up.
Jason saw several people from his high school, mostly girls, and he spent a few minutes talking to each.. The year before he would have kept his head down and not spoken to anyone.
At one point Jason even spent a little time hanging out with the step-sister and her bubbly friends, who were all impressed that he was milking a beer.
As the final band hit the stage, Jason gave up on picking up a one night stand. Several women were giving him a glance or two, but everyone was here with groups of people, and Jason lacked the experience to pull off picking a woman up when she is being guarded by her friends.
Giving up, Jason found a fairly vacant spot on the ground and took a seat on the damp grass. He was fairly new to drinking, and it was affecting him more than he would like to admit. He sat in silence for a while, nursing his beer. Suddenly, a pleasantly feminine voice said "You look like you are having a good night tonight."
Jason turned around and laid eyes on a very sexy looking raven haired woman in a silk shirt, short skirt combo. She might have been in her mid forties, and wore a lot of jewelry, silver and diamonds. Her shoes and purse alone probably cost more than Jason's jeep. But that was not the first thing Jason noticed about her. Or the second. The first thing he noticed were her long, toned and tanned legs. Her skirt was short and she sat in a reclining lawn chair, her long legs extending down towards where he sat on the grass. Jason was instantly sold on whatever she was selling.
"I am." he agreed, although she could have said 'Some tornado we are having right?' and he would have agreed. What he really heard was replaced with 'Hi, I am hot, wanna play the flirting game with me?' Thinking about what she had actually asked he asked, "How could you tell."
"The beer, the fact I have not seen you without one, and I've watched you talking to about 20 something people tonight," She smiled, and Jason liked her smile. He WAS a little buzzed, he decided, although in it was really only his third beer still, she just didn't realize he was nursing the same beer all night. "I specifically spotted you talking to a couple of cougars earlier."
Cougars? Oh, she meant Donna, Hylan and Melanie.
Why hadn't Jason noticed her before? He looked at the two black empty lawn chairs to her right and realized that he had, but she was here with two other attractive women so he wrote them off. He was not yet confidant enough to walk up to three hotties and introduce himself without looking like a nerd. Plus all three had been wearing big diamond wedding rings. This girls rock was pretty intimidating. She was alone now though. No husband, no girlfriends, no one to try and scare Jason off.
Come to think of it, the other two were here when he sat down just a second before. "Where did your friends go?" He asked, nodding to the empty chairs.
"Refill." She lifted an empty cup and sat it back on the grass. It was a one word answer, but somehow she made the simple, short answer seem sexy. "I take it you struck out?" she asked, raising a teasing eyebrow.
He smiled as he thought about how to answer. He didn't want to make her sound like a last resort. Although anyone you go home with is your last resort. You have to stop trying when you actually go home with someone. "What makes you think I took a swing?"
"You talked to quite a few girls not to be trying for something." she countered.
Jason used the effects of alcohol as the excuse to stall for an answer. He squinted and tilted his head as he thought of a response, as if a bit dizzy. "I have a lot of female friends." He winked at her.
"I bet you do." She tilted her head thoughtfully. "So why not take home any of your pretty friends? Not in the mood?" She smiled and shifted slightly in her seat. Her legs were crossed, but she lifted one slightly in the shift exposing more of her thigh. Jason noticed, and this stranger noticed that he noticed and smiled a little brighter. For some reason he had developed a slightly southern accent when he spoke to her, and he had planned on only sounding inebriated. She seemed to buy it.
He looked away from her for a second and sipped his beer, then turned to her, gesturing to the other concert goers. "Those cougars were just parents of my sister's friends. I was just flirting with them for fun. I am not interested in actually doing anything with older women who know my family."
