Story 36
Summary:
Will, nineteen years old. He’s been doing odd jobs all summer and dreaming of getting away. When his mother asks him to help a friend of hers, he can’t stop thinking about that friend and the crush that he has on her. But can dreams become a reality?
Pam and Ellen, early forties. Pam has seen the way that Will looks at her. Now that she's divorced and spending time with her divorced friend Ellen, they both want to have some fun and show him what it means when they say that they need a man to help them out.
Threesome, age gap, lesbian, oral, blow jobs, pussy licking, titty sucking, titty fucking, fingering, jerk off.
Since he had started working for himself, there had been plenty of jobs that Will hadn't enjoyed.
There had been quite a few that he didn't mind, and there had even been one or two that he had found to be at least slightly enjoyable.
All in all, he wasn't sure if being self-employed was really a career path that he wanted to take - certainly not in the realm of being a handyman - but he had told himself that it was only for one summer and that it could have been a lot worse.
He was nineteen years old, and he knew that his choices were to work for someone else or to do his own thing like this.
No one was about to put him into some kind of management position; he was sure of that.
However, for all of this, with his differing emotions regarding the different jobs that he had done up to this point, there hadn’t been a single one that made him feel the way that this one did.
His mother had dropped it into conversation casually the previous week.
“Do you have any free time next week?”
He had thought about it for several moments.
“I don’t think that I’ve got any bookings in for Thursday and Friday,” he had replied.
“Oh, that’s good. I was talking to Pam on the phone yesterday. She mentioned that she had a few jobs around the house that she needed some help with. A man’s touch, that’s how she put it. Maybe you can help her out?”
He had paused then. He was in the middle of eating his breakfast, and he froze with the spoon halfway between his mouth and the bowl. He swallowed the mashed-up mass of cornflakes and milk in his mouth and coughed, almost choking on it.
His mother turned to look at him curiously.
“Are you Ok?” she asked him.
“Yeah, yeah, sure.”
He was sure that he had to be blushing, that he had to have given away his secret to her, but she only looked at him for a moment and went back to whatever she was doing.
"Anyway," she said, "if you think that'll work out, then I'll let her know. Just let me know what time is good for you."
“Any time,” he said, trying to sound as casual as he possibly could, “any time at all is good for me.”
And ever since then, it had been on his mind. He had been unable to stop thinking about it - to stop thinking about her.
Pam. He'd had a crush on her since he had first met her a couple of years ago.
She had quickly become his mother's best friend, and he knew that his crush was wrong, that it was fruitless, that nothing could ever possibly come from it.
However, that didn't stop him from feeling like that.
In fact, he thought that she was possibly the most beautiful woman that he had ever seen.
She was only slightly above average height, but that was the only average thing about her.
Everything else was exquisite perfection.
She had an incredible body, with a slim waist, generous hips, shapely legs, a full, round ass, and large breasts - breasts that he had fantasized about, that he had thought about feeling, stroking, sucking on.
She had light skin and long, straight black hair. Her eyes were a light green, and she wore heavy eye makeup that, along with her naturally long eyelashes, seemed to accent them.
Her face was incredible. As well as her large eyes, she had a small, slightly curved nose, large, red lips, and slight dimples in her cheeks.
She exuded a smoldering intensity and sexuality.
She could turn her gaze on someone and make them feel as though her desire for them was burning deep within her, or she could smile and light up a whole room.
He thought that she was the most incredible woman that he had ever seen.
But he also knew that she was forty years old, although she looked younger than that, and he knew that she would never be interested in someone like him. He was sure of it. And yet, he still held onto that hope, as futile as he knew it was.
He knew that girls his own age found him attractive. It wasn’t a lack of self-confidence that was the problem here.
He was tall and well-built. He'd always been athletic, but a summer working outdoors had honed his physique further. He had broad shoulders and powerful upper arms. He often worked topless, and his body now had a deep, rich tan to it that seemed to highlight his muscles even further.
His light brown hair had also caught the sun and had now lightened slightly to almost seem like a dark blonde. It had become slightly overgrown over the summer, but it suited him.
He had a handsome face, with good bone structure, soulful, hazel eyes, and a contagious smile that lit up his face.
There had been plenty of girls who had shown an interest in him, and he'd had a lot of fun with them.
There was no problem for him there, and he was sure that when he went away to college in the fall, there would be plenty more girls that he would have fun with - new girls who would have come away from home for the first time and would be looking to have a good time.
In fact, as he worked over the summer, he found himself looking ahead to that time, thinking about how wonderful it was going to be, while also looking back at the fun that he'd been having over that summer as he and his friends all geared up to leave home.
In particular, he often found himself thinking about Sally.
Sally was the same age as he was and undeniably beautiful.
She was short and petite, with a slim figure, perky breasts, tight ass, and flat stomach. She had shoulder-length, dark brown hair, almond-shaped, brown eyes, and cute features, with rosy cheeks and a lovely smile.
Sometimes she could look almost innocent, but then, at other times, it would be clear that there was much more to her than that, and it had often left him wondering just what else she was hiding beneath the surface.
There had been a couple of times over the summer when they had chatted at parties.
They had hit it off and flirted with one another.
There had even been a couple of kisses, brief but passionate moments that had left him hot and heavy, his cock stiff in his pants, pushing to be released but, ultimately, frustrated.
He wanted more from her. He started to wonder if she was just teasing him, just having some fun with him for her own amusement.
However, one afternoon, everything had changed.
He had finished work early. He went home, showered, and changed.
He was wondering what to do with himself.
But it was a nice day, and that particular day, he had been forced to work inside.
So he decided that he would go for a walk, which was a decision that, when he looked back on it later, he was very grateful that he had taken.
He had been walking around the neighborhood, enjoying the feeling of the sun on his face, when a car had pulled up next to him.
When he realized that it was there, he turned to see who it was.
He saw Sally behind the wheel, leaning over to him, and suddenly a revolution occurred in his plans for the day. Suddenly, he felt as though the day had come alive with possibilities, and he wanted to see just where it might lead him.
“Hey there,” she said to him, “what are you up to?”
“Not a lot,” he replied, walking over and leaning down to look into her car. She was wearing a tight tank top that showed off her figure, clinging to her breasts, and a short skirt that showed off her toned legs.
"Well, why don't you jump in the car, and maybe we can do a lot together, what do you say?"
“I say that sounds like a great idea,” he replied, getting in the car.
She pulled out and they drove around, chatting to one another. It wasn’t long before the flirting began, and he could feel the tension in the air as the atmosphere shifted. He felt as though they were both just waiting for one of them to make a move.
“Anyone home at your place?” she asked him, trying to sound as casual as possible. He knew just why she was asking.
“My parents,” he said regretfully, “what about your place?”
“Same, same,” she replied. He felt as though they were thwarted. They drove on in silence.
"I've got an idea," Sally said after a while. She refused to elaborate, but instead drove them to the outskirts of town, out to some woodland. He looked around, wondering what was coming next as she pulled up.
She undid her seatbelt and turned to him.
Reaching down and grabbing a lever, she pushed his seat all the way back. Then, she undid his belt.
She climbed over onto him, straddling him. Her skirt was pushed right up, and he felt her thighs pushing against his, felt her crotch pushing down onto his. Could she feel that he was getting aroused? Could she feel the growing hardness in his pants?
He put his hands on her waist. She looked down at him, her hands on the seat on either side of his head.
She leaned in, her hair falling forward. She was breathing heavily, clearly excited.
“I think that we’ve waited long enough,” she said, breathlessly, “don’t you?”
"Absolutely," he replied, and then she leaned in to kiss him, kissing him long and slow, her tongue pushing into his mouth, searching for his, wanting his.
There was no hiding his arousal now. His cock was rock-hard, and she was pushing the crotch of her panties down onto it, letting him know that she wanted it.
She grabbed hold of his T-shirt and pulled it off as they broke their kiss for a moment.
Then, they started to kiss again, her hands on his body. She bent down to kiss his throat, his shoulders, then she kissed, licking, his chest.
His hands slid up beneath her top, and she raised her head so that he could pull it up over her head.