Joanna: The Pickup Artist Ch. 01

By Soulstroker (a.k.a Magnifico Giganticus)

Story Codes: F/m, gentle femdom, big breast fetish, mother/son incest role play, MILF.

Synopsis: An older woman who likes to pick up shy, unassuming younger men finds her latest conquest at a car wash. Who says older women cannot be pickup artists?

Author's note: The first part of this story, the part taking place at the carwash, is actually true. The people involved are described as they truly were and acted as far as memory serves. I've only filled in unknown information and then added in aliases and a sexually explicit ending which is entirely a fabrication of my own deprived imagination. Oh, how I wish things had progressed this way. As always, I look forward to hearing people's reactions. Please let me know what you thought of this story.

*

The woman looked to be in her late 30's. Some might even say she was in her mid 30's. But Joanna was in fact 41. She was a beautiful woman, but one that, at her age, was slowly losing her battle to stay youthful looking. The signs were subtle but clear enough to a critical eye, especially her own. She had started developing crow's feet and laugh lines in her face. Her matronly hips were a little wider then they used to be and her extremely generous bosom, which had always sagged due to its weight, sagged quite a bit more now. She had also developed a bit of a belly. Not so much as to be unattractive, but a gentle roundness was there and noticeable. The soft 10 or 15 extra pounds young women kept for child rearing had slowly crept to 30.

Still, she had done well in her war on age and had won on many fronts. Her exercise regiment helped keep her womanly figure. Her legs still looked as good as when she was young. Her breasts while sagging a bit more, had otherwise kept their perfect form and shape. She took pride in the fact that her large puffy nipples still pointed upwards and her lines where still that of the classic coke bottle shape. She stayed out of the sun as much as possible and was proud of the creamy clear complexion this afforded her. Thanks to diligent moisturizer use her skin was spot free and baby soft, even if her flesh was a bit plumper then when she was in her 20's. In fact, the only major sign of age was a few pale stretch marks on her sides; battle scars from having born four children.

Today Joanna was taking her youngest, Jenny, to the car wash. As usual, it had been much too long since her minivan had been cleaned and five-year-old Jenny had demanded that she be included in the outing. Unfortunately, Gregory's Brushless Carwash was not the drive-through variety, so they had to get out and watch the car go through the machine, much to Jenny's disappointment. It was a lazy Sunday, with temperatures close to 90 degrees and Joanna had opted to wear simple khaki shorts and an old faded t-shirt. She wore her dark cherry wood hair in a loose bun atop her head in an attempt to keep heat from building up around her shoulders and neck. After paying, she took Jenny to the glass enclosed waiting room to watch the cars go by through the various stages of the machine. Eventually Jenny got bored and the heat inside the enclosure was even more stifling, so Joanna took her daughter outside to sit on a bench to play with her toy. The bench was just outside, at the end of the machine's track where the cars drove off to staging areas to be hand-dried. The moist spray from the nearby carwash and a steady breeze felt good as they sat and waited for their car to come through.

As various other patrons milled about, unaware of anything else but their own cars, a young man suddenly plopped down on the bench next to Joanna. He was young looking for his age, but she correctly pegged him to be somewhere around 27 or 28. He was quit a bit overweight, but not unattractively so. The man was very tall and it helped to distribute his extra pounds well, giving him a big masculine presence. She also noticed that, despite his weight, he seemed very limber which suggested that he exercised regularly. In his hands he carried a mechanical pencil and a small book with the word "SUDOKU" printed in large friendly letters. The young man flipped open the cover to start on one of the puzzles after first taking a quick glance around towards the wash line to see how his car was doing. He used this action to also take a better look at the woman seated at the far end of the bench. He returned her smile and quickly averted his eyes back down to his puzzle. Joanna noted the surprised look on his face. He was started that she caught him looking at her. She thought the reaction sweet. He lifted his pencil to begin the puzzle but was intercepted:

"Hi"

He looked back to the woman next to him and put on a big smile. She looked pretty, and nicely built, but was much too old for him he thought. "Hello," he said to cover his thoughts.

The girl who he assumed was her daughter was busy playing with a toy and did not seem to notice him, but the mother's bird-bright eyes studied him intently. He resisted the temptation to look down at her over-large chest, knowing she would see him do so.

"That's smart," she leaned over slightly and yelled over the droning of the car wash, motioning towards his puzzle book.

"Oh… yeah," he smiled back after a short pause.

"Is it a crossword?"

"Sudoku? Oh no, it's with numbers."

She was familiar with Sudoku puzzles, but decided to flatter him.

"Oh, you must be good at math."

The young man gave a shy shrug and smiled, seemingly embarrassed by the flattery.

"I guess, but it's about logic really…." He hesitated as if afraid he would bore her if he went on, then made up his mind and scooted closer to show her a page in his book.

"You see, you have to fill in nine numbers here," he pointed with his pencil, "but you can't have the same number on the same row or column anywhere else…." He let his sentence fade as if he was afraid he had said too much.

"Oh, I see. You must be very intelligent." She beamed him another smile.

He shrugged again and smiled again, unsure how to respond. Then said: "I keep it in my car, just in case—"

"That's very smart. I wish I had thought of that."

"—it's low tech. No batteries to die on you." He finished awkwardly.

"That's right," she laughed, "that's very smart."

There was a long pause as the machines droned onwards. It was his turn to say something, but the young man seemed unsure how to keep the conversation going. He was about to begin his puzzle again when Joanna took over for him.

"I feel better when my car is clean, don't you?"

He looked back towards her, grateful that she had finally broken the uncomfortable pause.

"Yeah," He said with a slight laugh, betraying his sudden sense of relief.

"All these people are probably going away for the 4^th of July—," she looked around, waving her hand at all the cars being washed and dried, "—want to have their cars clean for the trip."

As she talked, the young man couldn't help but slide his gaze down to her chest, where her t-shirt was stretched taunt over the expanse of her breasts. He could clearly see the outline of her bra and its clasps. Her t-shirt was stuffed so tightly it rode high at the bottom and exposed a bit of her belly like a cut-off. He quickly looked back up to her face as she finished speaking. Too old perhaps, but still nice to look at he thought.

"I've got family coming to visit," the young man explained, "that's why I'm having my car cleaned—want to make a good impression."

"That's good. Making a good impression is very important."

He nodded as she spoke but didn't add anything.

"What's your name," asked the woman.

"Oh—Kevin," he said offering his hand. She accepted it with a dainty grip.

"Nice to meet you Kevin, I'm Joanna, and this here is little Jenny," she said hugging her daughter to her, "that's ours over there." She pointed to a silver Volkswagen minivan that was already being dried by two workers.

"Nice." He was unsure of what else to say. While it seemed to be in good condition, the minivan wasn't particularly new or old. It was just an average minivan. Joanna noted his attempt at being polite.

"It's good to have a reliable car, don't you think; one that will go a long, long time before you need to replace it."

Kevin nodded mutely, not sure what exactly she was getting at.

"Look at that one mommy!" Joanna's daughter was pointing past Kevin.

"That is a big one isn't it; my goodness what a large car."

Kevin turned to see his own Escalade SUV driving off the line.

"Um, that's mine," he said with an impish smile.

"That will definitely make a good impression, Kevin" Joanna nodded and grinned broadly, "a very, very good impression."

As luck would have it, his SUV was driven to a station next to Joanna's minivan and a crew quickly began to dry it.

"Shall we go?" Joanna asked, as she stood up and nodded towards the picnic-like tables situated near their cars. The trio made their way to the awning covering the tables. Several such areas were strewn around the many trying stations where cars were being worked on.

"You must have a very important job to be able to afford a car like that," Joanna said after they had once again seated themselves. Kevin was embarrassed by the fact that he was a trust-fund baby, and with the exception of several 'fun jobs' during high school and collage, had never really worked a day in his life. He simply smiled hoping that would be answer enough for this woman.

"So tell me more about these puzzles, are they very hard?" She asked and scooted close into contact with him so that he could show her more of the book. Kevin was taken off guard by her sudden invasion of his personal space. The hot press of her flesh against his made his already overheated frame tremor with excitement. She felt it.

"Um, no."

"Tell me Kevin," she spoke softly, her mouth only inches from his ear, "do you often use your Sudoku book as a prop to pick up girls?"

He was shocked by her sudden accusation. That had never been his intention. Even if he had thought of that, he wasn't nearly smooth enough to actually try it. Before Kevin had a chance to explain himself a worker next to Joanna's minivan wave a towel over his head, signaling that her car was ready.

"Oh, gotta go." She said, her eyes smiling and a tongue-in-cheek frown teasing him. Kevin was both saddened and relieved to have her dislodge herself from his side. He smiled and nodded in a manner he hoped looked innocent as she looked back and gave him her own good-bye smile. Little Jenny waved with her toy as she was tugged along behind her mother.

As she walked away with a seductive sway of the hips, Kevin thought how despite their age difference, he could imagine himself fucking this beautiful older woman. He had often fantasized about older women, but never about one he had met in person. As he watched her wide womanly ass undulate back and forth, he imagined himself grabbing those hips from behind and thrusting wantonly into her welcoming center. His lecherous stare slid up her back, and to the twin curves of her breasts that stuck out at each side—they were so large he could see them even with her back turned towards him. And they hung so full and heavy! Their weight must be massive. The image of his hands sliding around her sides to grab and paw at the massive mounds of flesh as she ground her ass back into him flashed through his head. God, the day's heat was getting to him, and his desire for this woman wasn't helping. He chided himself by remembering that she had a little daughter. What sort of man drools over a soccer mom out with her daughter he thought.

A minute later an waving towel by Kevin's car tripped him out of his lust-addled day dream. He headed to his car, a tip for the worker ready in his hand. He proceeded to inspect his car to see that no detail had been missed. Joanna's minivan was still parked next to his vehicle. She had just strapped her daughter in and was adjusting her mirrors. She saw Kevin walk nearby, completely engrossed with his work. It was time to see if she had seduced a little afternoon delight into her day.

"Hey Kevin."

He felt a nervous shiver run up his spine at the sound of her teasing voice, and snapped around to looked at her. She waved him closer.

"Why don't you come back to my place and you can show me more of your puzzles—what were they called again?" She feigned forgetfulness.

"Sudoku," he blurted without thinking.

"That's it. I bet they are a lot of fun with a smart guy like you around to help me."

Kevin was struck dumb. Was she saying what he thought she was saying? While he was pretty dense when it came to women, he was experienced enough to realize that when a girl asks you back to her place for puzzle solving, something entirely different was being offered. Either she was reacting favorably to his supposed attempt at picking her up, or she was hiting on him! An older woman no less—a sexy older woman. He suddenly felt a queasy feeling in the pit of his stomach. He wasn't exactly a smooth operator, and was deathly afraid of making a wrong move that would screw everything up.

"uh…"

"…is that a yes?"

Kevin felt a sudden pang of doubt. She was at least 10 years older then him. He shouldn't be lusting after women who were almost his mom's age. And wasn't the man supposed to hit on the woman? He felt as if his male-space had been violated, and yet felt relief that he didn't have to make the first move—even though he had never planned it to begin with.

He suddenly blurted out: "shouldn't we first have a date or something?"

Joanna chuckled at his naivety. He had just tipped his hat as to what he was expecting, an easy roll in the hay. Men were so cute when they were out of their depth. She also found it charming that his sense of masculine chivalry was trying to reassert itself.

Kevin regretted the words the moment he uttered them. Why would he say something as stupid as that? She was blatantly offering him sex. That's all he could think of when he looked at her. She oozed feminine sexuality. Was this his subconscious' pathetic attempt at playing hard to get?

"How about I fix you some lunch?" Joanna chuckled again. "That should do as a first date."

He secretly breathed a sigh of relief. His outburst hadn't ruined his chance with this woman.

"Come along and follow me, it's only 10 minutes from here."

As Kevin followed the Volkswagen minivan trepidation continued to build in him. He was wholly unprepared for this. He had left his home in sandals and cargo-shorts, not expecting any need to impress anyone. He nervously checked his breath and inspected his teeth and hair in the rearview mirror. He replayed the events at the carwash over and over, flabbergasted by his own blind dumb luck. He had acted like a clueless 15-year-old, but somehow this woman was still interested in him. He still couldn't believe he was following this soccer-mom type back to her home. What was he thinking? He had had a few one-night stands in college, but this was something wholly different. He realized how dumb and lucky he was, and how infinitely more experienced she was in every way.

He had long harbored fantasies of being with an experienced older woman, one with many years of practice on how to please a man. Many times he and tried to imagine what it would be like to bed a woman like that. Would Joanna make his dreams come to life, or was he completely off target with his expectations? What if this was all some sort of cruel joke? He was keenly aware of the many scenarios that lay before him, the vast majority of which, would no doubt end in humiliation and disgrace. His musings were cut short as he followed Joanna into a secluded cul-de-sac. Joanna's minivan parked itself in the driveway of a largish white house. It was well taken care of, but like the minivan, it was quite average and ordinary looking. Kevin quickly parked on the street in front and joined the mother and daughter as they made their way to the front door. He made sure to bring his Sudoku book and mechanical pencil.

"You have a lovely home," he said as he neared the waiting mother and child, pleased that it sounded so confident and polite.

"You're very kind," Joanna nodded as they entered, "why don't you keep me company in the kitchen while I make our lunch."

Like everything else, the lunch was very ordinary: club sandwiches with fruit salad and a grilled cheese sandwich for Jenny. While the food was tasty, the entire meal seemed perfunctory, as if they were both simply going through the motions for appearance sake. Joanna was giving him the 'first date' his male ego seemed to demand. For a brief moment Kevin thought she looked on the meal as a form of payment for a service he was about the render to her. The notion was disturbing, yet extremely erotic at the same time. Joanna seemed so casual about the whole affair. Her confidence and relaxed attitude was like an aphrodisiac.

Small talk permeated the meal, which lead to some coffee and more small talk. Kevin's Soduko book remained closed and unused on the edge of the table. Joanna seemed very elusive as to the nature of her family. When he asked what she did, she responded that she was a stay-at-home mom and homemaker. This suggested that she was married, but Joanna didn't wear a ring, nor had she a discolored band around her ring finger to suggest she regularly wore one. She skillfully evaded any discussion of a husband along with anything else about her family, except for little Jenny.

Soon after the coffee was served, Jenny started to become irritable and then sleepy. Joanna excused herself while she went and put Jenny to bed for her afternoon nap. By the time she got back the coffee was cold, and Kevin knew it was time to make his move. As the man he had to be the aggressor and initiate the intimacy. Joanna sensed his mounting tension, but had no intention of letting him make the first move.

"You know Kevin, I think we should be as honest as possible with each other. And let me tell you, I know exactly how you feel right now."

He was afraid to hear her continue, but asked, "You do?"

"Oh yes. I've come cross your type before. In fact, I go out of my way to find boys like you."

Boys? He thought, but instead said: "My type?"

"Yes," she scooted close and held his hand between her palms, "shy, insecure, and maybe just a little inexperienced." She paused for affect. "Now, we could sit here and watch you chase your own tail all day, or I can step in and help make things easier…." She let the statement dangle.

"uh, make things easier?" He parroted dumbly, stunned by how quickly things were going out of control.

"Yes, and I'll do that first by telling you that I find you incredibly charming."

"You do?"

"Oh yes, sweetie." She placed a hand on each of his cheeks, cradled his face lovingly. "You're everything I could want in a man. You're well mannered and polite; you try so hard to be good and decent. And you're so big and strong and masculine, and yet soft and cuddly at the same time," she shook his head teasingly, "a very lovely… man." There was a slight pause, as if she where about to call him a boy again.

He didn't know what to say. It sounded like she really meant every word.

"Listen, I know you think you are a nice guy. But nice guys don't knowingly go back to a strange woman's house for Sudoku games."

"Not a nice guy?"

She laughed at his shock. He so badly wanted to be respectable.

"Oh, you are sweetie, you are—but not in some ways. I mean, a handsome young man like yourself looking to an older woman—a mother—to get his jollies… hmmm?"