The Making Of A Gigolo (5) - Jill Trimble - Cover

The Making Of A Gigolo (5) - Jill Trimble

Copyright© 2007 by Lubrican

Chapter 1

Erotica Sex Story: Chapter 1 - Jill was divorced, and angry at men in general. Her ex was a bastard, and she expected other men to be the same. When things break, though, you usually have to find a man to repair them. A friend told her Bobby Dalton could fix anything. Her friend was right. He fixed much more than her washing machine.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Ma/ft   Consensual   Reluctant   Heterosexual   Incest   Oral Sex   Masturbation   Petting   Pregnancy  

Foreword

This is the fifth in a series of stories about how Bobby Dalton was transformed, from a normal teenage boy, into a man sought after by many women. His story starts with “The Making of a Gigolo - Tilly Johnson”, and there is much information in that first story and succeeding books that will be useful to you in understanding what happens in this story.

For your fullest enjoyment, and because parts of each story are continued in succeeding ones, please read the stories in order.

Bob


1971, February

Life was interesting in the Dalton house, in large part because the eldest of Bobby Dalton’s seven sisters was getting married. Since it was the first wedding in the family, the uproar was four or five times as ridiculous as it might be when, say Susie, who was his fourteen-year-old sister, got to that point. By then, there would likely have been three or four weddings in the family, which was comprised of seven girls, Bobby, and their mother.

Bobby wasn’t involved in the wedding plans, except that he’d be walking Mary down the aisle, since she had no father to do that. She insisted on that. He was much more involved with what would take place after the ceremony ... on the honeymoon. Mary was using her brother to practice on, so that her wedding night would be glorious, instead of frightening, or uncomfortable.

Mary was still a virgin, technically. She’d practiced everything else with Bobby, but actual intercourse, she had not engaged in. She’d gotten rid of her troublesome hymen by use of Bobby’s thick finger, but that was all.

With all the uproar, while all the women in the family were fully occupied with wedding plans, Bobby made sure he spent as much time away from the farm as he could, while still getting his chores done. Mamma had finally decided, a few months past that, if she took a part time job in town, she could make as much money renting the tillable land as they could if they farmed it themselves. Glen Beesum, at the feed mill, had been looking for a bookkeeper but couldn’t find one, because it was a part time job. She had taken that job. It suited everybody, because now she had time to plan the wedding and Bobby was free to expand his handyman business ... and the perks that went with it.

Bobby had, to this point in time, done work for a dozen people in town, among them four particular women. That work, unlikely as it may seem, turned out to include making all four of them pregnant.

The first, Tilly Johnson, was raising his three year old son, David. Bobby was a frequent visitor to the Johnson house, where he interacted with David while Tilly and Jake spent time alone in the bedroom. It was babysitting, of a sort, but it was intended for him to be able to bond with his son. Jake would always play the role of David’s father, but they still wanted the man who had improved their lives to be able to spend time with the baby he gave them.

Such was the case on June the ninth, which was David’s birthday. He was only three, so the celebration had been simple. Tilly and Jake left David with Bobby, so he could spend some one on one time with him, while they went and spent some one on one time with each other.

Eventually, Tilly padded out of the bedroom, dressed only in a loosely tied and thin robe, and took her son from Bobby’s lap, where they had been playing patty-cake. The little boy’s hand grabbed at her breast.

“No you don’t, buster,” she laughed. “I weaned you ages ago. You men are all alike!”

“We can’t help it, when a beautiful woman is around,” said Bobby, feeling his penis react to the fact that he could see one nipple through the gap in her robe. He hadn’t had sex with Tilly in two years. Her rule had always been that Bobby could only provide for her what Jake could not. Since they had found out that Jake could maintain an erection, her legs had been closed to Bobby. That didn’t mean she was modest around him. He had spent literally hours with her in bed, and that kind of closeness doesn’t lend itself to false modesty, even if they were no longer lovers.

Jake could not, however, get her pregnant.

“Bobby?” said Tilly, looking down at him.

“Yes?” he responded.

“Jake and I want another baby.”

“Is that so?” asked Bobby, his prick stiffening even more.

“You want to help us again?” she asked.

“Yes, Ma’am,” he said.

“I’m not going to act like a harlot, like last time,” she said. Bobby noticed that her exposed nipple had erected. “I’m only going to let you make love to me when I’m fertile.”

“I can live with that,” he said.

“Be right back,” she said. “I need to go give David to Jake.”

When she came back, she stood in front of Bobby again. “I’m fertile right now, Bobby.”

He took her right there on the couch.

She got up, holding his sperm in her with her fingers clamping her pussy lips closed.

“I said I wasn’t going to act like a harlot,” she said, standing in front of him, naked. “That doesn’t mean I want to be treated like some High School girl, sneaking sex on her parents’ couch.”

She took him to the spare bedroom, where they had conceived David, and had him make love to her in what she called “a more appropriate fashion.”

She had him visit every day, the rest of the week. Lying there, full of his sperm, she stroked his face one last time.

“If it didn’t work this month, I’ll call you next month,” she said.

“Okay,” he smiled.


Two days later, Bobby’s prick was sliding in and out of a different woman, whose belly was already swollen with his baby, making it a little difficult to treat her as she had become accustomed to being treated by him.

“I’m getting fat!” moaned Prudence.

“You’re supposed to,” he said, tugging at her swollen nipples.

“If I get any fatter, we won’t be able to do this,” she moaned.

“Want to learn a new way?” he asked.

“What new way?” she asked.

“You get on top,” he said.

“Women don’t get on top!” she snorted.

“Yes ... they do,” said Bobby, who knew very well that women got on top.

Once she got over the feeling of embarrassment of sitting up naked, Prudence found that she loved being on top. Her breasts had filled out already, and were embarrassingly big, to her mind.

“The 4th of July dance is coming up,” she said, riding him hard.

“I know,” he said, watching her breasts jiggle and wobble.

“I’ve never gone to any of the dances, since Harry died,” she said. “I want to go to this one. Will you dance with me, if I do?”

“Yes, I will,” he said.

“Everybody in town is gossiping about my belly,” she moaned. “If you dance with me, they’ll gossip about you too.”

“I don’t care,” he said. “I don’t mind if you tell them I did it.”

“You’re joking!” she gasped, grinding her clit on his pubic bone.

He stroked her belly, now five months along.

“I’m proud of my baby,” he said.

“We’ll see,” she said. “I don’t want to go, if nobody dances with me, though.”

“I’ll make it look like a charity dance,” he said. “Will that do?”

She laughed out loud. “Yes, that will do nicely.”


The 4th of July picnic and dance was, as usual, a raucous affair. Because the fourth was on a Sunday that year, the festivities were scheduled for the third, but nobody cared. The kids all brought firecrackers, and other fireworks, but were restricted to setting them off only in one corner of the town square. The picnic tables were set up at the other end of the square, and the bandstand, a huge gazebo, was in the middle. Park benches and tables with folding chairs, scattered all around the square, gave people places to sit and talk.

As usual, the picnic area evolved into two basic groups. Mirriam Dalton, and the dozen or so other women who had ended up in the arms of Joe, a hobo kind of man who hung around town during the Korean War, formed one. They had been traditionally ostracized by the more virtuous women in town, who loved to gossip about them. All the children played together, but the womenfolk stayed apart.

That tradition, however, was being stretched a little. Fred Brogan was engaged to be married to one of the “war babies” as Joe’s progeny were called, in satirical whispers. Jenny Brogan, his mother, had fought the idea, until she actually met and got to know Mary Dalton who she found, to her surprise, was a delightful girl. In the process of wedding planning, she had gotten to know Mirriam Dalton too, and had been even more pleasantly surprised to find she liked the woman she had gossiped about so often with her friends.

Others gravitated toward the table that the Dalton’s inhabited that night, too. Tilly Johnson, pushing Jake in his wheel chair, their son on his lap, appeared to ‘stroll by’ that table and stayed there, with Fred, Mary and Mirriam. Three year old David toddled around, making friends, among them Mirriam’s other daughters, who also scampered around shooting off firecrackers, or gathered in groups of their friends. Some of those groups - the older ones - included boys.

Martha and Arthur Thompson wandered by and stopped. They had been making the rounds, so that didn’t seem odd, other than the fact that they hadn’t done that in years past. Martha’s one year old, Andrew, was in her arms.

Sherry and Sam Winston also stopped by, with their one year old daughter, Jessica, but stayed only long enough to be sociable.

There was a surge of tongue-wagging when Prudence Harris got there. She was visibly pregnant, and had been a widow for as long as most people could remember. The employees at the bank had gossiped about her pregnant state, unable to hazard a guess as to who the father was. Most of them joked that it had to be an immaculate conception, since she was never known to have socialized. She had never come to the town gatherings since her husband died, either, which was one reason so many people noticed her.

This, however, was a different Prudence Harris than most people in the town square had ever seen. Her maternity dress was a riot of colors, with a rainbow spread over that swollen abdomen, and clouds where her breasts were. Her legs had trees, and grass with babies playing on it. It was obvious she felt no shame, and people whispered excitedly.

Those whispers got even more excited as she was welcomed by the women who had born “war babies”. Why anyone was surprised that she’d gravitate to that group was strange. If anyone would have thought about it, they’d have realized that those women probably knew how Prudence felt, having a baby out of wedlock, and that they probably didn’t care who had put that baby inside her.

Mirriam, knowing that Bobby had worked for all of these women, and suspecting he was involved in the parentage of all those babies, bit her lip and made sure she was polite to everyone. When Prudence Harris asked if she could join her, she patted the bench beside her.

“I have no idea when all the girls will show up to eat,” she said. “But you’re welcome to sit here. They can fend for themselves.”

“You’re very kind,” said Prudence. “I wanted to apologize for snubbing you all these years.”

“Nonsense,” snorted Mirriam. “We weren’t the best of friends in school, either.”

“I know, but I thought badly of you. It was wrong. It only took twenty years for me to grow up. I just wanted to say I don’t think badly of you now, and I’m sorry that I ever did.”

“Thank you,” said Mirriam, with dignity. She couldn’t help glancing at Prudence’s pregnant belly.

“Are you doing all right?” she asked.

“If you mean am I happy that this happened?” said Prudence, cutting through the polite chatter. “Actually, I’m very happy.”

“Really!” said Mirriam, entranced.

“The father of this little thing inside me is a wonderful man,” Prudence said.

“Are you going to marry him?” asked Mirriam, holding her breath.

“No,” said Prudence. “If I were ten years younger, I might think about it, but it wouldn’t work out. I had trouble enough with one husband. I don’t think I want another.” She smiled. “Raising a baby is a breeze compared to living with a husband.”

“That’s a very enlightened way of looking at it,” said Mirriam. “This man ... the father ... he must be very special indeed ... unless, of course...” She didn’t finish.

“Unless it was an accident?” Prudence smiled. “Some accidents turn out to be the best thing that could happen to you, don’t you think? There’s a word for it: Serendipity.”

“I’m very relieved that you feel that way,” admitted Mirriam, now convinced that Bobby was the father of the baby in Prudence’s womb.

“I’d like to be friends,” said Prudence. “Do you think we could do that?”

“I’d love nothing more,” said Mirriam, smiling.


The girls came, played with David, stared at Prudence, ate, and then went off to be with their friends, as Mirriam and Prudence got reacquainted. Dusk arrived and the end of the square was lit up with night-time fireworks. The town show wasn’t due to start for another two hours. Experience had shown that people liked to dance first, and then sit back and be awed by the big boomers, up in the sky. There were four bands, each scheduled to play for half an hour. The first was a country band, by tradition.

Mirriam and Prudence were still talking, when a shadow fell over them. They looked up to see a man, standing between them and the bandstand. He was looking at Mirriam.

“Care to dance, Ma’am?” he asked.

Mirriam stared up at him, surprised beyond measure. No man had ever asked her to dance at a town get-together since she’d had her third daughter. That was in 1953, over fifteen years ago.

“I’ve plum forgotten how to dance,” she blurted.

“I’m no Fred Astaire, either,” said the man, smiling.

Mirriam looked at Prudence, who was grinning.

“Go on!” encouraged her new friend.

She got up, and, rather than trying to remember, just started swaying with the music. He did basically the same thing, holding her hand and swinging back from her, in an arc, and then coming forward. He twirled her a little awkwardly. The music had been going on when he invited her, and by the time they got on the dance area, only half the song was left. He walked her back to her seat, as another song started.

“How about you?” he asked, looking at Prudence. “If your husband won’t mind,” he said, looking at her left hand, where she still wore her wedding rings. Her pregnancy was hidden by the table.

“I’m not married,” said Prudence, her voice level. “My husband died a while back.”

“I’m sorry to hear that,” said the man. “Do you think he’d object to a dance?”

“He would object most strenuously,” said Prudence, who now thought about her husband much differently than she would have a year ago. “But he’s not here.” Her hands went to her bulging belly, almost subconsciously. “Still, I’d feel silly dancing.”

“Oh please,” begged the man. “Just one dance?”

It was a repeat of the earlier incident, except that this time it was Prudence who looked at Mirriam, and Mirriam who grinned and said, “Go on!”

“Oh, all right,” said Prudence.

“Excellent!” said the man, smiling.

She stood, and revealed her pregnant status, waiting to see what his reaction would be.

“Most excellent, indeed,” he said, his smile never wavering.


“This is embarrassing,” admitted Prudence, as they started doing the same thing he had done with Mirriam.

“It’s just for fun,” he said, over the music. “Who cares what it looks like, as long as we have a little fun?”

“You’re not from around here, are you?” asked Prudence.

“Just moved to town,” he said. “Going to teach school next year.”

“Well welcome, stranger!” said Prudence, understanding why he had mistakenly thought she and Mirriam were normal women. “I have to tell you, though, you’ve probably ruined your reputation already by dancing with me.”

“I know,” he called out, grinning.

The song ended before he could say more, and he walked back with her to Mirriam.

“How do you know?” she asked him, as she sat down.

“How do I know what?” asked Mirriam.

“Not you,” said Prudence. “Him.”

“How does he know what?” asked Mirriam, looking confused.

“This is...”

“Ted,” said the man, smiling. “Ted Brandywine, formerly of St. Louis, Missouri, and currently a new resident of Granger, where the air smells better, and the women are prettier.”

“Don’t you have a silver tongue,” said Mirriam.

“I told him he’d probably already ruined his reputation by dancing with us,” said Prudence.

“Both of you?” Ted’s face showed much more shock than his eyes did.

“He said he knew that,” said Prudence, ignoring him.

“How do you know?” asked Mirriam.

“That’s what I was asking him,” complained Prudence.

“It’s a simple thing,” said Ted. “I hung around and watched everybody. I’m from the big city, and a people-watcher from way back, so I’ve learned a lot about how people act. I saw who was gossiping, and who they were staring daggers at while they were doing it. A number of you ladies over here seemed to be frowned at the most, so I decided to ask you all to dance.”

“All of us?” asked Mirriam.

“Well, that was my original intent,” said Ted. “However, after sampling two of you, I can already tell I have my hands full, so you two will do.”

“You’re quite bold!” said Mirriam, frowning.

“I’m just a fun-loving guy,” said the man. “I was married to a woman who was more stiff and proper than Grandma McGillicuty at a nudist retreat. When she divorced me, I came west to start a new life. I decided that the interesting women were probably going to be the ones that all the stuffy, proper ones were talking about.” He grinned. “I’m testing that theory right now.”

“And why, exactly, did your wife divorce you?” asked Mirriam.

“Very direct,” commented Ted. “I like that. I hate beating around the bush.” He sat down. “I told her I wanted children, one too many times.”

“How many times did you tell her that?” asked Prudence, intrigued despite herself.

“Oh, I guess three or four times a week,” he said. “At least lately. It was probably more than that in years past.” He smiled. “We’d been married ten years.”

“You were married for ten years, and didn’t have any children?!” Mirriam was clearly curious.

“She was of the opinion that babies are both loud, and messy, neither of which she tolerated in the house,” he said. “I admit I badgered her a bit.”

“Still, that’s no grounds for divorce,” said Prudence.

“Are you kidding?” he said. “When she said she wanted a divorce, I agreed so fast it made her head spin. Irreconcilable differences is what they called it. I should have gotten out years ago. I’m thirty-two. The best years of my life are gone!”

“Nonsense!” said Mirriam. “But you’re a little young for the likes of us.” She jumped, as she realized what she’d said, and blushed. “Not that we’re interested,” she added. When she realized how that sounded, she put her elbow on the table, and dropped her head into her open hand.

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