Chapter 1

Bobby Grisham was as ordinary as the day is long ... except he wasn’t ordinary at all.

Obviously, this sounds a little goofy, but stay with me for a few paragraphs and you’ll understand.

He was ordinary in the sense that he was seventeen, would be a senior in high school when the next term started, and had a part time summer job to earn a little spending money. He still had a few customers from his early working days as a lawn-mower/weed-puller/fence-painter/anything-else-somebody-needed. He had two parents, a man and a woman, and they had been married a little over nineteen years. He was an only child, stood a hair over five feet, ten inches and weighed one hundred and ninety-five pounds. Most of that was muscle, thanks to his other summer job at a lumber company. He lived in an ordinary town with a population of eight thousand and some. He was between girlfriends because he didn’t want things to get too serious before he figured out what he was going to do after high school. His grade point average was 3.25 and he still rode a bike most places because he was saving up for a car.

So, at first glance, he seemed ordinary.

That leads us to the not-ordinary-at-all part of things.

For one thing, Bobby had befriended the first and only black male who had ever been enrolled in the Pine Bluffs High School. Russell was also seventeen and his sister was the only other black student in the school. Bobby was virtually Russell’s only friend because Russell’s father was the Chief of Police and everybody assumed Russell would rat out any unsavory or illegal behavior; say, at a party or whatever. Nothing would have been further from the truth, but it didn’t matter. Bobby was his only friend and they had become “best” friends.

That, alone, might not have made Bobby un-ordinary. After all, merely doing the right thing by ignoring skin color and seeing personalities instead isn’t odd. It was a tad bit odd in Pine Bluffs, but only because there were almost no black residents. The town wasn’t racist, by and large. Rather there were just no opportunities for the residents of a sleepy town, established in 1909, and which did not, back then, welcome any blacks, Chinamen, Irishmen, or lay-abouts. But more about the town later. These paragraphs are about Bobby Grisham.

The primary reason he wasn’t “ordinary” was because, at the relatively tender age of seventeen, he’d had more sex than the average hard partying college senior, much less any of his high school peers. Not only was he very experienced, all that history wasn’t with girls his age. Rather, in the roughly year and a half that he’d been learning how to be a superb lover, his instructors had been older women, two of whom were technically old enough to be his mother. The others were comfortable with him as a lover because high school wasn’t all that far behind them.

Basically, back before he turned sixteen, Bobby Grisham had sex roughly twice a week during the school year, and three or four times a week during the following summer vacation. He had, eventually, been basically adopted by five women as what some might have called their personal gigolo, except they didn’t pay him for his services. They paid him for the little odd jobs he did for them, but not for the sex.

That is what made Bobby unusual among his peers. He was unusual compared to most grown men, too, for that matter.

The way it started was that one of the five women had her twenty-eighth birthday and her husband forgot it completely. The boy who mowed her lawn, however, did not. He just happened to show up on the momentous day to keep her lawn at the three point five inches in length she preferred. She didn’t exactly plan to seduce the then fifteen-and-a half-year-old. She was just very emotionally vulnerable that day and he was cute. She’d thought he was cute for a while. This was because she’d found out her husband had peculiar sexual interests. Among them, he wanted to have an open marriage. Not only that, he wanted her to go to swap parties with him. She had refused to do this (she found out about his desires a couple of years after the wedding) and her not-quite-four-year marriage had slowly died. It had been six months since she’d been intimate with her husband. She’d been thinking about getting a divorce before he forgot her birthday.

When the handsome, polite, attentive young man who took care of her yard knocked on her door and wished her a happy birthday, she invited him into the house. Somehow, over the next hour, things got more and more relaxed until the T shirt and terrycloth shorts she’d been wearing ended up on the floor. They landed on top of Bobby’s shirt and jeans. Neither of them had been wearing any underwear. They were both astonished it had happened, but neither was sorry.

She was his first, and he acted like it. She remembered how quickly a teenager can recharge, though, and taught him how to be intimate emotionally, as well as sexually. The second time he lasted long enough that she could teach him how to make her cum - twice. The third time he left her in a limp puddle of very satisfied and sperm-soaked woman. In all, he’d been inside her house for three hours. Then, with a smile on his face, he went back outside and mowed her lawn. To his credit, when he was finished, he did not ask her if he could fuck her again. She had given him a gift and he did not abuse it. He charged her for mowing the lawn and went home.

Bobby knew nothing about the travails adult women go through in their emotional and sex lives. The only real attention he’d given older women, at that point, was to his teachers and to the minister’s wife. The ‘Mrs. Reverend’ looked like a reformed porn star (to him) and he had much to feel guilty about every Sunday as the minister kept telling his flock their sins were forgiven. Usually, Bobby left church with another sin below his belt as he glanced at the woman and imagined her naked. Interestingly, that happened less and less because, over the next year and a half, there were other women in church whom he had seen naked. He had, in fact, done a lot more than just see them sans clothing. He had pushed his adolescent penis into their vaginas lustily and spilled his teenage spunk in them repeatedly. That ... distracted him, shall we say ... from the MILF who was married to the preacher and who had borne him two children.

That jumps ahead of the story, though. How things progressed to that point is why this story is being written.

Trudy Carver was the woman who plucked Bobby’s low-hanging cherry. She was never sorry she debauched him because the boy who didn’t even have a driver’s license yet gave her more emotional attention (and orgasms) than her husband had since they’d been married, three and a half years earlier. She was very particular about her yard and she ‘hired’ Bobby a lot. Two things happened that expanded his sexual life. One was that there is only so much that can be done to a pristine lawn, which meant Trudy didn’t get to feel his lusty young prick pounding in her as often as either of them would have liked. The other was that all four of the other women in her “card club” noticed how upbeat she suddenly became.

“Card Club” is in quotes because it wasn’t a formal club, but it was the excuse they used to get together once a week and escape the hum drum of life for a couple of hours. It was also an excuse to tipple a little wine before noon, too.

There was one exception to the wine and that was Sarah Cunningham, who was still nursing her children, one four years and the other eighteen months old. The four-year-old had enjoyed sucking his mamma’s nipples so much that she couldn’t wean him. When another baby came along, she just got loved by another precious little thing. Her problem was that her husband thought milky breasts were disgusting and he couldn’t stand it if she leaked on him while they were having sex. He seemed not to want sex very often anyway and the only reason she had two babies was because the first was a boy and he wanted a daughter. He made her wear a bra when they had sex until she was pregnant again.

Another of her problems, as it would turn out, was that she thought because she was nursing she was not fertile. The very existence of the baby happily slurping on her left breast belied that old wives’ tale but she didn’t think about it like that. Logan hadn’t touched her since his daughter had been born and, since she planned to breast feed both of her children until they were five, she assumed Logan wasn’t going to touch her for roughly three and a half more years.

She was bemoaning this fact to the members of her social support group in the card club one Thursday afternoon and it wasn’t the first time she’d complained. All the women complained to each other about the things that made them sad or unhappy or unsatisfied with their lives. That was part of what the card club was for. They’d known each other for more than three years, having established the informal group at a church picnic. Of course back then nobody talked about her sex life; not at first. There were plenty of other disappointments in their lives and as the cards sailed expertly across a table and were picked up the mood got more and more relaxed until, one day, things took a turn.

As it happened, it was Betty Wilshire who said what tipped the scales. She had been surly at the beginning of the game, which was unlike her. Betty was forty and the eldest of the members of the club. She had one child, a boy who was in college, and her husband worked for a company that specialized in doing corporate tax returns. Her home was nice and her life had always looked comfortable to the others. That’s why it was odd when Cathy Brown asked, “What’s wrong? You’re acting like you had a fight with your best friend,” and Betty blurted, “Oh, I don’t know. I think I just need to get laid!”

She had not intended to say something like that. Of course this new subject of discussion was eagerly mined. The girls loved to gossip, but mostly about each other’s lives and to each other as all of them tried to avoid getting the Queen of Spades in a trick.

“But you’re married!” said Julie Tipper, the only single woman in the group. “You can get laid any time you want!”

All four of the other members of the club laughed – and not mirthful laughter – and the education of poor Julie commenced, concerning husbands and their foibles.

They already knew each other pretty well. Sex had been avoided in their discussions for two reasons. The first was that it wasn’t polite to inquire about that aspect of another woman’s life. If it came up you could discuss it, but no one ever brought that kind of thing up. The second was that all of them were embarrassed about their sex lives, or lack thereof. Women often feel like what ails them ails only them and they don’t want their girlfriends to find out how fucked up their lives are. When that dam breaks and they find out everybody else’s life is fucked up, too, a kind of catharsis takes place.

In this case, Betty, little by little, confessed that her husband had erectile dysfunction and that she hadn’t had sex in over four years.

There were murmurs establishing how everyone present thought that was too bad.

“But he’s so young!” murmured Sarah.

“He’s thirty pounds overweight, smoked like a chimney for years until he finally quit two years ago, and has diabetes, as well as who knows what else,” said Betty. “ He brought this on himself and now we’re both paying for it.”

There was much commiseration but no solution to her problem was put forth – at least, not until the game was over, that day. As they went their separate ways Trudy casually addressed Betty and said, “If you have a second there’s something I want to talk to you about.” Betty did have a minute and Trudy beat around the bush until she finally whispered, “I might know how you could get laid ... privately.”

Betty was shocked, initially, and when she found out who Trudy was talking about she was even more shocked. First of all, the boy was only sixteen. More troubling than that, though, was that his mother was one of her church friends. The cat was out of the bag, though, and when the shock wore off and Trudy waxed almost poetic about how happy she was, Betty said, “I wondered why you didn’t talk about your sex life during the confab we just had.

“I don’t really have anything to be upset about,” sighed Trudy.

“So ... how does one go about arranging something like that?”

“I could introduce you to him,” suggested Trudy.

“You mean say something like ‘Bobby, this is Betty Wilshire and she needs to get laid. Do you think you could help her?’”

“Not like that,” groaned Trudy. “He’s due to work on my yard Saturday. Why don’t you come over for tea around ten in the morning.”

“Okay,” said Betty, warily. “What, then?”

“I don’t know. Just come over and be prepared to stay a while. And wear something comfortable.”

“Comfortable?”

“Something you can take off easily and quickly,” said Trudy, who had been blushing for five minutes, by then.

“This is insane,” snorted Betty. “I can’t just plan to cuckold my husband with a boy who isn’t even out of high school!”

“You said Dan wishes things weren’t like they are, right?”

“Yes. How does that matter?”

“You could ask him to give you permission to find what he can’t give you ... um ... elsewhere?” Trudy’s voice made a statement, but it sounded like a question.

“Ask my husband, the father of my twenty-year-old son, if I can dally with a teenager so I’m not so cripplingly horny anymore?”

“All he could say was no,” moaned Trudy. “What have you got to lose?”

“My marriage, maybe?” snorted Betty, who still wasn’t taking all of this seriously.

“Your very unhappy marriage,” said Trudy, who had admitted to the group that she thought, more than occasionally, about divorcing her husband.

“Unhappy or not, I made my vows and I meant them. All that talk about leaving him is just blowing off steam.”

“If you have permission, then your vows are still intact,” argued Trudy.

“I love you,” said Betty, “but this is just ridiculous.”

“At least come over Saturday and meet him. Nothing has to be said about anything. Just talk to him. You’ll see. He’s such a delightful young man and I can’t even begin to tell you how happy he’s made me by filling in the same kind of blank space you have in your marriage.”

“You are completely insane,” said Betty. “Thank you, though. You lifted my spirits by making me smile. I’ll see you later.”

She had then walked to her car and gone home.

But she couldn’t stop thinking about Trudy’s... “proposal.”

One reason she couldn’t stop thinking about it was because Dan, her husband, had actually told her in a moment of anguished emotion that she should find another man who could give her what she needed ... and what he couldn’t give her. She had argued and they had cried together. She had sucked his soft dick, which was pleasurable for her, because he could actually cum that way if she sucked it just so.

But it always left her ragingly horny and he never could quite figure out how to return the favor in a manner that satisfied her fully. She had gone to a city an hour and a half drive away so she could survey an astonishing array of sex toys and choose two to take home. They helped, but they weren’t warm, human flesh. She really did need to get laid.

And now there was an avenue she could stroll down to do that.

It wasn’t a done deal in her mind, of course. It was more like that person who sees a sports car and thinks, ‘That would be fun to own,’ only to think ‘But I can’t afford it.’ She had seen the young man, of course. His mother and she were members of a group that volunteered at the local food bank. She’d never talked to the boy. She hadn’t really paid much attention to him.

And then there was Dan. His suggestion had been tearful and emotional, as had her tearful assurance that she loved him and wasn’t going to try to replace him. But ... had he really meant it?

If he had, then this crazy idea of Trudy’s might not be so crazy after all.

Could she become that vulnerable to a sixteen-year-old boy? Didn’t boys brag about their conquests? If it came out that she’d cheated on her husband with a teenager her life would be ruined. Dan’s life would be ruined.

But she still couldn’t stop thinking about it.

Which was why, that night, she sucked her husband’s limp prick until it dribbled semen and he groaned his appreciation. Then she cuddled with him, which was something he could do really well, and asked, “Did you mean it when you said I should find another man to ... help me?”

She was amazed when he panted, “It would have to be the right man. And he would have to be very discreet.”

“Really?”

“I love you, Honey, and it kills me that I can’t hear you make those noises you made when I could still ... do that with you. We’d just have to be really careful about it. That’s my only concern.”

“I’ll think about it,” she said. “I love you so much!”

“That is why I’m not worried that some other man will steal you away from me,” he said, squeezing her.

Then he went down on her and gave her the only kind of orgasm he still could. It wasn’t anything to write home about, but it was an orgasm.

The next morning, after Dan had gone to work, Betty had called Trudy.

“Is that offer of tea still on the table?” she asked.

“Yes!” gasped her friend.

“I’ll see you at ten. But this doesn’t mean anything is going to happen.”

“Of course,” said Trudy. “You’ll be glad you came.”

Betty felt like she was a voyeur of some kind. She and Trudy were peeking between a set of curtains, watching a high school student pushing a lawnmower carefully around Trudy’s yard. He was shirtless in the summer heat and had on ragged cut-off jeans shorts. His feet were in a pair of grass-stained tennis shoes. All in all, he was the very picture of virile, attractive young male. Part of what bothered her was that her son was away in college and was quite likely engaged in making some girl ... or possibly woman ... squeal in the same way she wished she was squealing. What would he say if he knew what she was contemplating?

What he might have said, if he had all the facts, was, “You’re a MILF, Mom, and if Dad’s on board, you deserve to be happy.”

He would never have any of the facts, however. Only Dan ... and Trudy ... would be aware of her... “affair”?

“He’s so gorgeous,” sighed Trudy. She was so unrepentant about what she said she did with this boy that it was a little communicable, and Betty felt a very familiar dampness begin to collect in her vagina.

“He is,” she admitted. “I still don’t know how this could ... um ... work out.” She had already told Trudy she did, in fact, have permission to ... stray. Since Trudy had made herself so vulnerable by admitting what she did with Bobby, Betty felt it was necessary for her to become vulnerable as well. It was only fair. And it further cemented their friendship.

“We’ll think of something,” said Trudy.

What “they” thought of was eerily like Betty’s previously sarcastic comment, when she had imitated Trudy and said, “Bobby, this is Betty Wilshire and she needs to get laid. Do you think you could help her?”

When Bobby came into the front door he was still shirtless. If he was sweating heavily he sometimes took a shower in Trudy’s bathroom before mounting his lover and rutting in her, giving her very welcome orgasms with his stiff, adolescent penis. Today he was sweating heavily, but he looked at Trudy with one eyebrow raised.

“This is my friend, Betty,” said Trudy. “She’s a very good friend. You look like you could use a shower.”

“Um ... yeah,” he said. He looked at Betty. “It’s nice to meet you, Ma’am.”

“Betty walked all the way over here to visit me and she got all sweaty, too,” said Trudy. “Maybe you could share the shower with her ... you know ... to save water?”

Bobby wasn’t stupid. His GPA didn’t reflect his level of intelligence. He understood immediately that this new woman knew about what he and Trudy did. If Trudy was suggesting something like that, then she believed nothing bad would happen. And the woman was beautiful in the same way a classic muscle car that has been kept in tip top shape. She still made a man’s heart race.

“Trudy!” gasped the new woman, clearly shocked.

“I’d like that very much,” said Bobby. “I think saving water is a good thing.”

“Trudy?” Betty’s voice cracked a little as she looked at her friend.

“Go take a shower. You both need one.”

If Bobby hadn’t extended his hand, inviting her to take it, she might have fled, but his calm, gentlemanly demeanor, and dark eyes she felt like she could just fall into, made her stay. Trudy stayed where she was, which also helped. As soon as they got into Trudy’s bedroom, though, she pulled her hand away.

“I don’t do this!” she gasped.

“You don’t take showers?” He was still calm.

“I think you know what I mean,” she said.

“Trudy gets a little carried away, sometimes,” he said. “She means well. I don’t know why she thinks this needs to happen but all it has to be is a shower if that’s all you want.”

It was his characterization of the situation being one in which she could choose things that made her keep staying. She had choices. And he was allowing her to opt out if that’s what she wanted. Or to opt for ... something ... something less than what Dan had told her she could do.

“Just a shower?” she whispered.

“I’d love that,” he said.

Then he took his shorts off and Betty saw what Dan had said she could have.

“I’ve never done this before,” she whined. She was naked, in a shower stall with a boy she didn’t actually know, who had the biggest penis she’d ever seen outside a porn site. He had brought her hands to slide all over his body, spreading soap everywhere. Only after she had touched him did he reach to slide soapy hands around her body. She was surprised that he didn’t immediately grab for her breasts. She was proud of her breasts, which were still firm and shapely, with very little sag to them. When Dan tried to make her feel good he gave her a lot of nipple love before sucking her clitty until her sexual tension was released. But Bobby only washed her. They both knew she didn’t need to be washed. The fact that he didn’t grope her made her actually feel a little more relaxed. It was extremely intimate, but it felt like acceptable intimacy, somehow.

When her hand ran into his penis it was still hard. It was hard for her. She couldn’t keep her hand from grasping it and she moaned at the semi-familiar feel of a stiff prick in her hand. It felt a little different because he was uncircumcised and the extra skin smoothed his prod, somehow.

Only after she touched him did he wash her breasts. Her hand tightened on his penis and suddenly his face was right in front of hers.

“I really want to kiss you,” he said.

“Okay,” she whimpered.

She knew she was lost because his lips communicated a raw male hunger she hadn’t seen or felt for more than a decade. As soon as she kissed him, she knew she’d end up in bed with him.

He still didn’t rush her as he dried her off, almost massaging her with a towel while he ignored the water drops on his own skin. He knelt to dry her legs and she had to step sideways with one leg as the towel slid up toward her pussy. He leaned forward and kissed her mons; just a little, loving peck. Then he stood up, sucking each nipple gently on his way. She moaned as he did that and shuffled her feet.

“I don’t want to push things,” he said, with his face just an inch from hers, “but I really want to take you to bed and I’m pretty sure Trudy won’t mind if we used hers.”

“Ohhhh,” she moaned.

“Is it too fast? Do I need to stop?”

She swallowed. If he stopped now she was pretty sure she’d have a breakdown.

“I’ve never done this before,” she whispered.

“Sure you have. You have a son,” he said.

“I mean had an affair,” she said.

“If it bothers you, then we won’t do it,” he said.

“My husband said I could!” she blurted.

“What?”

She felt shame and blushed hotly, but the cat was out of the bag.

“He can’t ... um ... get hard anymore. He knows I need that, and he said I could cheat on him if I wanted to.”

“It isn’t cheating if you have permission ... right?”

“It’s not that simple,” she moaned. “I barely know you. Your mother and I volunteer together! I’ve never done this!”

“Do you want to do this?” His question sounded completely sane and reasonable, so she answered in the same manner.

“Yes. I think I’ll go crazy if I don’t.”

He hugged her, then, and his stiff penis pressed into her abdomen. His hug was warm and firm, with no hint of sexuality in it, barring the being naked part.

“Let’s go lie down and rest,” he said. “We can talk. We can talk about anything and I’ll never tell anyone what you tell me ... or whatever we do.”

“Yes,” she sighed. “We can just lie down.”

Trudy had enjoyed almost a year of being loved by Bobby. That’s what it felt like to her. He wasn’t in love with her but he loved to make her happy. They had spent hours engaged in pillow talk, between episodes, and he had learned – some of it by osmosis – how a woman felt about the world she was trapped in. He knew Trudy’s situation well and while he knew all women were different, he also knew they shared some concerns. One of those concerns was about being used as a receptacle for a man’s pleasure when the man did not return the favor. He didn’t know what Betty’s situation was, other than that she had a weird husband, but he knew Trudy craved having his honest interest in her as a person. The sex was actually the frosting on top. She needed to be loved, as a human being first, and as a sexual partner next.

He hoped Betty would feel the same way.

And she would have reacted very well to his honest interest in her as a woman, even as young as he was, but he never got the chance to woo her in that way. Not this time, anyway.

That was because, once they were lying on the bed, not quite touching, and he kissed her again, something broke inside her and a tsunami of frustration and separation overwhelmed her and she pulled him on top of her to protect her from the crashing wave of unhappiness. She wasn’t actively thinking of getting him in her. She wasn’t actively thinking of anything, actually. She was just reacting, letting instinct tell her what to do.

Trudy had trained him well. He needed no hand to aid his penis in finding her slick entrance. When the tip felt the heat he just eased himself into her until his pubic bone bounced gently off of hers. He added a little roll of his hips to abuse her clit and moaned, “Ohhhh, I love this,” in her ear.

Bobby Grisham owned her in that moment, as he gave her exactly what she needed. Later she’d look at him, astonished that she had let a boy that young become so intimate with her. But she would also always feel the pull of being with him again. Part of her knew that as soon as he penetrated her and gave that little hip wiggle. She had what could be called a cataclysmic orgasm. It was cathartic as well as delicious. She’d craved this feeling for so long that it felt like finding an old friend after years of separation. It also made her weak and she fell limp, sobbing in release as he began to move in a more expected way. When he paused, obviously aware she was crying, she hugged him and told him to keep going; that she was fine.

She wasn’t fine. She was already addicted. He was long and thick and he stretched her perfectly. Every part of what he did to her made her feel like she’d finally gotten out of the desert, and was having her first sip of cool water after weeks of almost dying of thirst. And then he’d go in deep and grind and another orgasm would rush toward her. She wouldn’t have been able to stop those orgasms if she tried. But she didn’t try to resist. She welcomed each one and he did everything perfectly ... save one thing.

When she heard his groan and felt the thing in her throb, followed by the ball of heat that exploded in her belly, she knew he was cumming in her.

She wasn’t on birth control. She didn’t need birth control, because she didn’t do this.

“Nooo,” she whined. She was forty and the last thing she needed was another baby in her life.

“You shouldn’t have cum in me,” she chastised, as she engaged in pillow talk with the stranger she couldn’t do without.

“I didn’t know that. Trudy always wants me to shoot inside her, unless she’s sucking me and wants to swallow it.”

He sounded so innocent, and yet his performance suggested he was ten years older than his chronological age.

“Getting pregnant right now would be a terrible thing,” she said.

“Why?”

“Why? Because I already had a child. He’s grown and gone. I’m forty years old and supposed to be enjoying my freedom, not changing diapers.”