[This is one of my longest stories. I wrote it for the buildup and the foreplay and the ridiculous fantasy. If you're looking for a quick fix, this might not be it. But if you have time for some edging and exposition, enjoy.]
Dalton was thrilled. He had the entire summer to himself.
He was 18 and had just graduated high school and was planning on taking a year off before deciding on which college to give way too much money to.
His parents were taking their long-awaited cruise around the world, which they'd been talking about doing for years. This meant he had the whole place to himself to sleep in and do whatever the hell he wanted.
Not a bad gig for a a very popular 18-year-old with zero responsibilities.
They knew he was probably gonna throw a party or two. They just asked him to be smart, not do any hard drugs, and avoid being arrested. It was great to have cool parents. They were partiers in their day too after all. They weren't naive.
He was three days into this marvelous freedom when he'd received a text from his buddy Shane that a group of his friends were going to be meeting at the park across the street from his house that stoned and eat Chipotle and hang out. It was 11 AM and Dalton was still in bed.
He opened his laptop and had a quick jack-off session like he did every morning, and then went to jump in the shower.
Around 12 he was strolling out the front door wearing shorts, a baseball t-shirt, and flip-flops. The sunshine and the possibilities felt glorious on his quickly developing summer tan.
On his way out the door he spotted his next-door neighbor Mrs. Holloway walking with her one-year-old daughter, London. Her first name was Adrienne, if he remembered correctly. And he probably should remember, he'd gawked at Mrs. Holloway's obvious hotness from the moment they'd moved into the house some three years prior.
She was a young widow, after her husband had died a few years back from a rare genetic disease. It was a shock to everyone that knew them. They'd been such a lovely, powerhouse couple. She was only 27, and well off from the money he'd left her. She didn't really need to work, but she ran a weekend bakery in town, just to be around people and find something to distract herself with. She dated occasionally but was mostly bored with the options she encountered in town. They'd left the big city because they were ready for the comfortable, family portion of their life. And now she was on her own again. Just her and London, hanging in there, trying to find purpose in a mid-size suburb—feeling at times, a little lost.
Dalton had jacked off plenty of times thinking about this young MILF of a neighbor. Particularly on those days where he saw her tanning in their backyard from his upstairs window. She had these tiny bathing suits and on occasion would go sans top, not knowing that he was often in his room, spanking his monkey to the surprise display of supple nudity. His bedroom was the only one in the house with a good view of the neighbor's pool due to the height of their cherrywood fence, and he thanked his lucky stars for such an arrangement.
She had brownish-blond hair with natural curls. It was always messy and attractive. It was always as it needed to be. Sexy. Fun. Funky. She basically looked hot in every thematic situation.
Today she was wearing a very short jumper and tank-top with slip-on sandals and a hemp leg bracelet. Her hair was thrown up in a simple pony and she was wearing a large pair of rose gold sunglasses. She just looked effortlessly cute.
Her daughter London was now walking everywhere, in that brave waddle of first worldly explorations, and she was constantly chasing the giggly little girl around the street and nearby cul-de-sac.
"Hey, Dalton!" She waved kindly as she always did. She truly was a stellar neighbor. Everyone in the community loved her, besides the wives who had to scold their husbands when her juicy ass walked by and they invariably drooled, but even most of the wives wouldn't have minded getting a taste of her booty. She was that kind of hot. She actually looked a lot like Giada de Laurentiis, Dalton thought, after seeing the gorgeous celebrity chef on one of her Mom's favorite cooking shows. She had a similar sort of sexy pep to her. She was also only 5'2, which is why she often wore heels, which only further accentuated that lovely ass that she worked to keep so fit. She ran and did hundreds of resistance band squats and all sorts of Yoga.
"Hey Mrs. Holloway," he responded back. Always feeling slightly nervous around the attractive woman.
"How are the parents?" She asked, as she corralled London to her exposed thigh to hold the child close.
"Oh, they're amazing! They're on their cruise right now," he told her, trying not to stare at her breasts poking out from the top of her loose tank top.
"Oh that's right, your Mom mentioned that. So...you get to have the whole house to yourself, eh? That sounds like a pretty sweet setup for...what are you, 17 now?" She asked, mostly distracted by her daughter running through her legs over and over again as she played.
"No, I turned 18 at the beginning of the year," he said proudly, trying his best to keep his eyes off her legs and ass and breasts and lips and everything else she had going on.
"Ah, that's right," she said, but it was clear her daughter was becoming impatient to continue on to the park. The sun was out and fun was waiting. "Well, it was nice talking to you...we have a date with a playground to get to...talk to ya later!" She said, and they were off.
"Bye Mrs. Holloway!" He said, and she looked back over her shoulder and smiled, even as her goegeous booty sashayed away.
"You can call me Adrienne. 'Mrs. Holloway' makes me feel old," she gave him a friendly wave and he repeated the gesture.
Dalton cut across the street which emptied directly into a sprawling, tree-lined park that was at the very center of the upper-middle income neighborhood he'd grown up in. It really was a great place to grow up. Little League baseball and soccer took place right across the street. There were four baseball diamonds, daytime and nighttime tennis courts, tons of fields and some area of rolling grass hills where playgrounds, a dog park, and bocce ball courts all collided together in a spiderweb of outdoor activity. The park even had a lovely lake at its center where people fed ducks bread even though the signs said not to.
Dalton headed over to the large area of sloping grass hills which dotted the top of the park. When he got there he saw five of his friends spread out on a hodgepodge of blankets and towels, with various drinks in hand. There was a portable speaker and some opened bags of cookies and potato chips.
"Sup, losers!" He said, to the two girls and three guys hanging in a loose circle, enjoying the midday sunshine.
It was a lazy Tuesday on the first week of summer. Some kids would be starting college in the fall, some would be traveling, and others would simply be taking the year off, like Dalton was, to do some wandering. Such was the inherent privilege some were born into. Dalton tried to keep this in mind when it came to the way he carried himself. He was a good kid. So were his friends.
But they were also 18-year-olds, so. . .
"We're doing all the weed and drinking all the alcohols!" A girl named Keona said in a humorous voice. He'd taken her to Prom the year before. They were long-time, platonic friends.
"Ah yes, the devil's lettuce and whatever shitty beer you guys were able to steal from Brooster's brother's garage," Dalton joked as as they laughed in agreement. They clearly had already gotten a head start.
"What...you think Keystone Light is shitty beer??" Brooster said in mock indignation. He opened a bottle and handed it to Dalton. His name was Bruce, but he hated it because he said it made him sound like a 48-year-old life insurance salesman. And he wasn't wrong.
Kelsey and Bennet and Shane rounded out the group. Dalton said 'whassup' to everyone with various fist bumps and quirks, and an afternoon of drinking and smoking and not worrying about anything at all, soon commenced. What a time to be alive.
It was some hours later and Dalton was a little sun-burnt and a little cross-faded. He decided to head home and order himself a pizza.
He polished off his beer and tossed it into a nearby can with that effortless confidence of youth.
"Kobe doin' work!" Brooster hyped, as Dalton strolled away chuckling, after saying goodbye to his friends. The late afternoon air felt relaxing on his skin. He was only wearing shorts and a t-shirt.
As he headed back to the house on the main path he came across the smaller of the parks three playgrounds.
He noticed the familiar frame and sexy hair of Mrs. Holloway, perched at a nearby playground speaking with what was clearly a very interested Dad. London was, as usual, the most energetic bumblebee in the hive; climbing this way and that on the nearby equipment. She was already incredibly adept at the various slides and ladders for not even being two.
This was probably their second visit to the park that day. Mrs. Holloway usually made numerous trips when London was feeling particularly bored.
Dalton noticed that she was doing her best to be polite and shed his advances, but he'd probably been BBQ day-drinking, as so many of the fathers in the neighborhood were known to do if they were home during the day.
Suburbia was a nightly fucking rerun, that was for sure, Dalton thought to himself.
And then, as he got closer to Mrs. Holloway, he caught her eye for a moment and she almost seemed to smile, as if this might give her an out.
"Oh, hey Dalton! How are the parents?" She asked, making up a reason for a conversation. The Dad already looked irritated as he turned around to see the popular neighborhood teen approaching.
Dalton was about to save her and respond when his eyes scanned over to the big kid swingset where a darting London was waddling directly across the path of the incoming swingers.
The kid in the first seat was a high-schooler messing around with his friends. They were doing cherry bombs and flips and other varieties of never-grow-up revelry. The kid was big and stocky.
Adrienne followed his worried expression to see what he had seen. She gasped.
Dalton felt a burst of adrenaline and did the only thing he could. He sprinted past Mrs. Holloway and the divorcee and dove down to his knees on the playground wood chips, pushing London forward and out of the way, just in the nanosecond of time.
She flew an extra foot and fell on her face, just between the diving bombs of childhood kinetic energy swooping from on high.
The next thing that happened was the most painful thing that had ever happened in Dalton's fairly charmed life up until that point.
He was smashed into where London had just been standing.
