Gang of Five
Chapter 26

Copyright© 2009 by Shrink42

Romantic Sex Story: Chapter 26 - A close-knit group of older women who seem to have it all seek to fill the one big lack in their lives. When they succeed, will that be enough, or will they be drawn to new challenges? Several connections to the 'Transformations' series. MInimal codes used.

Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa   Consensual   Romantic  

Phyllis had a smile as big as the sun that Sunday morning as the Gang gathered for their regular brunch. Claire could not resist a tease. "But you've worked with pro teams who won championships."

The day before, Sean had completed his championship quest. Only two of his championship matches reached the second round. Grant Jacobs, the erstwhile favorite for the title, had moved up a weight class immediately after Sean had beaten him so soundly during the conference schedule. There was time for Jacobs to qualify for the finals in his new class. Sean had no other serious competitors.

"Oh, those titles were great," Phyllis replied. "I took a lot of pride in them. The times when I was voted a partial share of the title money were nice, too. "But looking back, those were jobs. With Sean, it's ... it's just so much more."

"I hear that!" or similar comments came from several of the others.

"Carole, isn't it just about a year since you met Sean?"

"Very close," Carole answered. "Looking at the weather today, it's hard to believe it all started with me trying to mow the lawn last year at this time."

"Speaking of that," Nancy interjected, "Is everything ready for his birthday present?"

"The truck is all purchased, and the new tools will be delivered in plenty of time," Carole assured them. "Do you think he can really make enough to cover all this investment?"

"Well, not every businessman gets to try his big expansion gamble with a safety net like we're giving him," Julie opined. "Besides, we got good prices on all of the stuff. If he had to liquidate, he could recoup a lot. You know how well he takes care of things."

"Are we really sure that he will insist on paying us back?"

Julie assured them "We would not be doing him a favor by outright gifts. Besides, it would turn a business deduction into a tax liability."

The others gaped at Julie for a moment, then shook their heads in embarrassment.

To change the subject, Nancy asked "Julie, were you surprised when Sarah wanted to work with him this summer?"

"I was more surprised when Jess wanted to. That was the real stunner," Julie answered.

"Well, how about Tracey," Claire prompted. "I doubt she has ever done any physical labor."

"I think it will be good for all three girls," Phyllis said. "I know Jess wishes Troy could join them, but she understands that it is better for him to stay at the club."

"Didn't Jess want to continue her job at the club?"

"She did, but it was Troy who insisted that the outside work would do her more good. I think he realizes how much she needs to be with other girls her age."

"Aren't Jess and Troy just the sweetest couple ever?" Claire commented, without a trace of her usual ribald humor or sarcasm. "It's hard to believe two such innocents existed in this day and age."

"How innocent could Troy be after all that time he spent with Sarah when she was naked?"

"Well, except for when he was in the pool with me after Sarah's party, he had no actual experience with sex," Phyllis pointed out. She hesitated a long moment, then blurted out "Oh, I can trust all of you never to tell." She then recounted the episode of the video Sarah had given to Troy.

"Sarah did that?" Nancy exclaimed.

"Remember," Julie said, "nudity means little to her any more. She genuinely liked Troy. She regretted that she did not return his feelings for her. I think it was a brilliant way to get the two together. You have to admit, they want the same things from life. Obviously, her sell job on Jess worked."

Again in a very serious mood, Claire observed "All three girls, Sarah, Jess, and Tracey, were great fun for me. No offense, Julie, but I think Jess gave me the most satisfaction."

"Oh, I understand," Julie assure Claire. "Sarah was a Cinderella story, but at least she had Dan. Poor Jess was really all alone."

"I understand that Troy's folks have practically adopted Jess," Carole mentioned.

"Once she dropped that edgy persona, she is a real sweetie," Phyllis chimed in. "I know Troy is completely besotted."

"Besotted?" Claire challenged with a grin. "That isn't a sports term, is it?" Phyllis just stuck out her tongue in answer.

"How is it affecting Sarah, knowing that Tracey is making love with Sean?" Nancy asked.

Knowing the question was directed at her, Julie answered "Well, I've made it a real point not to talk about sex things with her. I have really encouraged her to go to her mother."

"Is it working?"

"Seems to be. Sarah has told me how amazed she is at what she can talk to Arlene about. The old hurts aren't all gone, but what a difference!"

"You know, girls, of all the things that happened over the last couple of years, I think Arlene has to be our biggest accomplishment," Carole declared.

"That's hard to argue with," Phyllis agreed. "The result is three people made very happy."

"If you include Jess, that's four. Maybe even five, with Troy."

"Don't forget, Carole, that your taking a bath with Sean started it all."

"Maybe we could really say that luring Roger into the shower at the club started it all," Phyllis countered.


As the Gang chatted over brunch, Troy lay panting in bed in one of Nancy's several bedrooms. He and Jess had spent the night, and Jess had very definite ideas about how that Sunday should begin. Those ideas strained Troy's semen production system to the limit, especially after the night before.

There was no way he was getting hard again, but Jess liked to fondle him soft, too. Actually, she hungered for any chance to play with any part of his body. Self-image problems from a lifetime of repression would probably be with her forever. Troy was making great progress toward healing her, though.

Jess had become almost a fanatic about working out. Dan had even been forced to lay down some rules about finishing homework before she could work out. It never caused a problem. Jess just wanted so badly to 'deserve' a man with a body like Troy's. Once convinced that with her curves, excellent conditioning would make her body incredibly sexy, she went for it with everything she had. It was probably the first thing in her life she had gone after wholeheartedly.

Arlene, in her newfound wisdom, counseled Jess constantly that she should take care of her body for herself, not just for Troy. Arlene's own experience had showed her that a strong self-image was very sexy.

A great incentive for Jess was that the physical culture scene increased her bond with Troy. He was going into a body profession. The more she could understand what he did, the more they could do together, the better it would be.

Jess had surprised everyone with her commitment to only sharing sex with the man she would grow old with. It was really only a surprise because of the rather rebellious attitude she had always displayed. Attitude was all the rebellion amounted to. It was her only way of preserving some 'self' in the face of her mother's restrictive domination.

Back when Jess first met Troy and instantly decided that she wanted him, she desperately needed a woman to talk to. Of course she talked to Sarah, endlessly, but Sarah was still a virgin, too. Admittedly with a bit of malice, Sarah almost ordered Jess to talk with Arlene.

Still puzzled as to why her daughter had 'passed' on Troy, Arlene was well aware of how completely smitten Jess was. She took the initiative to start the conversation.

"Jess, Honey, I probably don't seem like the best woman for advice about sex, but I would love to help you any way I can. It's obvious that when you met Troy, it was love at first sight."

"But he ... I don't know if he likes me."

"Oh, I know," Arlene said firmly. "He likes you very much. He's a great guy, Jess."

"Aren't you sad that Sarah doesn't want him? She could have him, you know."

"As I'm sure you know, there are a lot of things about my daughter that I don't understand," Arlene admitted. "I'm doing better, but her, um, 'passing' on both Troy and Sean puzzles me. At your age, I reacted more like you. Once I met Dan, that's all I wanted. Of course, I was all screwed up on my reasons for wanting him. You don't have that problem, do you, Jess? My sister hasn't completely messed you up, has she?"

"Well, um..."

"When you're with him, do you want to get right in bed with him? Is that how he makes you feel, Jess?"

"Arlene!"

"You need to talk to someone about those feelings, Jess. I never could. Lorraine never could, either. It's only since ... well, you know, Honey. I had to learn that those feelings in a woman are normal and natural. They're nothing to be ashamed of."

"When I'm with Troy, I can't even figure out how I feel," Jess bemoaned. "It's like I have this ache, this empty feeling."

"That's good, Jess. That's how the right man is supposed to make a woman feel. The only problem is that men who aren't worthy can cause those feelings, too. You don't have to worry about that with Troy, that's for sure. He's a real prize."

"We've only been together a few times, you know."

 
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