Gang of Five
Chapter 9

Copyright© 2009 by Shrink42

Romantic Sex Story: Chapter 9 - 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  

"Time for another escalation," Carole announced at Sunday brunch after the dance.

"Finally! All the way this time?" Claire chortled.

Phyllis took over. "No, Claire. Not yet."

"Why now?" Julie asked.

"Well, he will be fifteen shortly, and the legal risk is greatly reduced. Besides, haven't you noticed that he is hard less of the time in the hot tub, lately?" Carole queried.

"I was going to ask for permission to take that problem in hand," Claire deadpanned. The fact that the others were so familiar with her quips that it took an exceptional joke to produce more than a groan did not stop her from dropping the corny ones.

"I don't think we should jump right to that," Carole said seriously. "We'll all benefit, though, Claire."

"I want to teach him massage," Phyllis explained. "I'll start out straight, but we can let it move to sensual massage. We can tell by how he reacts to our old bodies whether he has any desire to go farther."

In an unusually serious tone, Claire said "I love that kid. I want to see my friendship with him grow, and I want some good fucking to be part of that friendship."

"Just like with a husband, you mean?" That chilled the debate a bit, and Phyllis was encouraged to proceed with her massage idea.

Julie took the discussion in a whole new direction. "I have a particular interest in Sean's, uh, development. I've talked a lot about my son Dan's girl, Sarah. She'll be a senior next year, and it's pretty sad. She's just the sweetest thing, but so shy. Arlene, her mother, has kept her totally ignorant, sexually. No sex ed, no dances, no dating, strict control of TV and the Net.

"Anyway, I have been trying to think of ways to have Sarah spend some time with Sean. He would be perfect to start opening her up as far as boys and sex."

"Do you mean opening up like I want him to open me up?" Claire joked.

"It would take a long time to get her to that point," Julie chuckled.

"Don't be so sure," Phyllis warned. "If she is that repressed and put in a sexually charged situation, she could just lose herself. How many times have we heard about that?"

"But Sean wouldn't do that to her," Carole objected.

"If he was in control of himself," Julie corrected. "The more sexual experience he had, the easier it would be for him to do what was best for Sarah."

"Look, girls," Nancy chimed in, "None of us buy the old 'only one man for life' total monogamy business. Those of us who were married were faithful while we had husbands, but outside of that..."

"My Dan is the world's biggest argument for pre-marital sex," Julie insisted. "No one would have guessed Arlene's severe intercourse phobia from her behavior before they married. It almost makes Sarah a miracle child."

"And that applies to Sean how?" Phyllis demanded.

"A variety of sexual experiences can help him better choose a life partner," Nancy said.

"Julie, tell us more about your Sarah and Sean," Carole suggested to change the subject. "I agree that he would be perfect to try to help your granddaughter out of her shell. The problem is how to get them together. Also, I assume she is seventeen, right? That's two years older than Sean."

"But she looks more like fourteen, and knows less," Julie pointed out. "I don't know if Arlene's repressive attitude has anything to do with it, but she is behind in physical development. The age difference would not be an issue. Besides, I'm not talking about them going together. They live across town, you know."

"Exactly what did you have in mind?" Carole asked gently.

"Carole, all I really have is worry about Sarah turning out like her mother, and a thought that Sean could help her."

"It's unlike you not to have a detailed plan already," Carole said. "You must really be concerned. Girls - strategy time."

"Have you tried to do any sex education when Sarah visits you?" Claire asked. "I know you two are close and she comes to your house frequently."

"I have been very cautious not to upset Arlene. You know, she thinks of me as a loose woman. Somehow, she heard about the guys."

"What about Dan? Is he concerned about his daughter's backwardness? Can you get your son to stand up to Arlene on Sarah's behalf?"

"I'm afraid he may be clueless about Sarah, but it seems like he has been doing more of that standing up to Arlene lately, and their marriage is showing some real strain," Julia told them. "I'm actually surprised they are planning a trip in a couple of months."

"What's the problem with the marriage?"

"I think the kids would say 'duh'! I love sex and so did my husband. Up until he met Arlene, Dan seemed to have an active sex life. I don't think he gets much, and it has to wear him down."

"Has he said anything to you about it?"

"Oh, how I wish I could talk to him like I do Sean," Julie lamented.

"Why don't you just try doing it? It sounds like it's intervention time," Carole said. "I think you should talk to him just like you do to Sean."

"Well, we've always had a pretty good relationship, so I guess ... Hey! You don't mean..."

"Of course I do. Naked in the hot tub. If you do that, you will get his attention for sure."

"I couldn't do that! He's my son! We've never ... we've always been modest, and..."

"Julie, 'we've always' and 'we've never' need to be out the window if this is a truly serious situation. If he shows up to find you naked, will he take you seriously when you say you have something important to talk about? Damn right, he will!"

Julie was aghast, of course, but soon the others were working on her full force. As it turned out, getting in the hot tub naked with her son was only the beginning from their devious, fertile minds. Before the 'Sean Project' was anywhere near finished, they were ready to start another one - maybe two.


Phyllis could make it to Carole's that evening, so they arranged for Sean to come over after dinner. He had spent the whole Sunday working to catch up for time lost the previous week, so it was an appropriate start. He no longer had to be reminded to strip as soon as he got to one of the Gang's homes, as long as there were no outsiders there.

"I didn't shower before dinner. Give me a couple of minutes," he said rather wearily. He used the master bath, as Carole had always insisted, and when he came out, Phyllis had a portable massage table set up and was standing in position.

"Sean, Honey, you really should have had massages long ago. I'm sure it would have helped some soreness. I hope you can understand why we tried to limit the touching."

"So, you're not worrying about that any more? Great! I'm plenty sore tonight."

After much discussion, they had decided he should have the full non-erotic treatment. That meant that Phyllis worked everywhere on both sides, except for his cock. When she turned him on his back, he was already as hard as stone, but the women acted as if it was customary - actually, it was.

She did such a marvelous job that he actually wilted and fell asleep as she was finishing. They left him for a half hour until he came wandering out to where they were watching TV.

"Do you feel refreshed enough to learn how to do that to Carole?"

"I'd never be too tired for that," was the answer which earned him a searing kiss from Carole, just before she stripped down.

For over twenty minutes, Phyllis showed him the most common techniques. She kept him strictly on Carole's back, shoulders, and neck for the first session. After a few minutes, he commented "This is how a woman's back is supposed to feel, isn't it?"

Phyllis could not suppress a chuckle when Carole suddenly writhed her hips around on the table. "You can't rub your clit that way, Carole. It just won't work."

Carole gasped and blushed over most of her body. Sean looked up at Phyllis with a quizzical expression. "Sean, a comment like that about her body will arouse any woman, guaranteed."

"Oh, I was just thinking out loud."

"That's what made it all the more arousing. It's what you really felt."

When it seemed like a good stopping point had been reached, Sean said "Your turn, Phyllis. I can't wait to feel your back." It was not in the plan, but there was no way she was going to refuse. Over the next few days, Sean repeated the first lesson on the other three women.


The week after the dance, Sean was working at Nancy's and just enjoying the new confidence he felt. Late in the afternoon, Nancy called and asked him to come to the patio. There, he found Rebecca, dressed in what must be her office attire.

"Should I go inside and undress, or just do it here?" he quipped.

"Sean!" Nancy tried to scold around her giggles, "Rebecca just wants to ask you a favor?"

"A favor where I can leave my clothes on? Wow!"

"Well, sort of," Rebecca could not resist saying.

"Oh, well. I knew it was too good to be true," he said dramatically.

"So," Rebecca continued, "think you can meet girls OK without your cock exposed?"

"Well, it was actually fun at the dance."

"I've got two daughters, eleven and ten," Rebecca said. "We come over here to swim - and escape - a lot. Also, when summer comes, the girls will be here some whole days with Nancy. I thought we could arrange a time for you to meet them. That way if they are here when you are working, it won't seem strange."

"Eleven and ten, huh? I have no experience with younger girls. Actually, I don't have experience with any girls, I guess. If I can wear a swimsuit, I shouldn't get too flustered, though," Sean commented.

"Sean, Honey, the girls may be young, but they are precocious," Nancy told him.

"If they are Rebecca's daughters, they would have to be," he said quickly.

"Sean!" Rebecca exclaimed, trying to sound stern. "Nancy, I see how he got into the hot tub with you so easily - the others, too."

"Rebecca!" Now, it was Nancy's turn to try to act upset. "Really, Sean, I always say the girls are eleven and ten going on thirty. Just treat them as if they were high school girls."

Shifting the subject rather abruptly, Sean asked "You don't have a pool, Rebecca?"

"Oh, we do. It's not completely private like Nancy's, and ... uh, well..."

Sensing a sensitive topic, Sean interrupted. "With school and work, there isn't much time during the week."

"Maybe an hour or so before you go home for dinner?" Nancy sggested. "And maybe on the weekend?"

"That's a good idea, Nancy. Sean, if you can just fit in a little time, it will be a good way for you to get acquainted. I really want them to get to know you."

"Okay, Rebecca. I'm going to leave it up to Nancy to tell me when to be here. Oh, and when I get to wear a suit."

"The girls aren't here right now," Rebecca teased.

"Good idea!" he enthused. "Last one naked is a rotten egg!"

"Sean, no! I didn't mean..." Rebecca stammered before breaking into laughter.

Sean left with no skinny dipping having occurred. As he went through the gate at the side of the house, Rebecca just stared after him. Nancy put her hand on her niece's shoulder and joked "Thinking about him as a future son-in-law?"

Talking as if in a trance, Rebecca said "Why should one of the girls get him? I ... God, Nancy! What's wrong with me?"

"Sounds like maybe terminal horniness to me," Nancy answered, still trying to keep things light. Then, in a serious tone "Anything new - good or bad?"

"When was the last time there was anything good? You already know about the last time we had sex," Rebecca grumbled. All Nancy could do was put her arms around from behind Rebecca and hug her.

"I'm afraid it is going to affect my practice, Nancy. Several times, I've been giving advice and I've almost had to stop. Nothing I've tried works for me. How can I suggest it to someone else?"

"But you always tell people that they can't change their partners, don't you?" Nancy counseled. "You can't help Jason's ego problem."

"Then I ask myself if I shouldn't value my marriage enough to quit my practice."

"Alright, Rebecca, tell me exactly what you would tell some other wife who made more than her husband and was thinking about taking a backward step," Nancy said sternly.

"Yeah, you're right. I'd just end up hating him for what I had to give up."

"Are you sure he is being as faithful as you are?"

"Doesn't matter. I would lose all credibility with myself if broke my vows. Then I really could not counsel anyone else. I have a feeling, Nancy, that resolution isn't too far off."

"You're assuming he will be gone. That's why you want a male presence for the girls, right?"

"Smarty-pants," Rebecca accused. Nancy responded with a quick tickle, and the two women who were as close as any mother and daughter purposely abandoned the somber mood.


Nancy did arrange for Sean to stop work early and come over one afternoon. After showering and changing into his swimsuit, he stood behind the patio door for a few minutes, just watching the girls.

They seemed to be in constant motion. Nancy's bragging about their appearance had not been just idle talk. They were definitely still little girls, but they were slim, well-formed, and graceful. Just watching their slender legs and tight little asses as they scampered around the pool was more arousing than he would have suspected. The older one, Theresa, he remembered, had some definite soft protrusions on her chest, and the line from her armpits to her hips took a fetching little detour inward at her waist.

While he watched, they were in and out of the pool a few times, and when they climbed out again, he went out to meet them. Later, Nancy was rather upset that she had no warning because the reactions were worth seeing.

Ten-year-old Michelle spotted him first and hollered "He's here!" Turning in mid-scamper, Theresa froze at the sight of him, then went all demure and as lady-like as she knew how. Rebecca saw it and alerted Nancy. From the corner of his eye, Sean could see the women trying to stifle snickers.

Since Theresa, especially, seemed immobile, Sean walked up to them. "Hi. I'm Sean Massey. I'm happy to meet you girls. You must be Theresa, and..."

"I'm Mike," she blurted out. "She's Teri! She's only Theresa when she's in trouble. Then it's Theresa Marie Sanders."

"MIKE!" Teri objected, trying to show ladylike disgust.

"And who are you when you're in trouble?" he challenged.

He got some quick verification of Nancy's claims about the girls' quick wit. "I can't remember. It's been so long since I was in trouble," Mike stated with a smirk that reminded Sean so much of Claire.

It probably would have been best to consult with Rebecca before his next action, but Mike had definitely thrown out a challenge. As little as he knew about young girls, he still could not let that pass. They were completely unprepared for his lunge, and he was able get one of them under each arm. Within a few steps, they were splashing into the pool together.

Somewhere on the way, Teri decided that demure and ladylike could be put off for later, and before the ripples died down, Sean was under furious attack.

With the women watching, he let himself revert to their age in the pool. Purposely, he added his own shouts and mock roars to their giggles and squeals. Splashing, diving under water to surprise and tickle them, throwing them through the air, riding them on his shoulders; he did an admirable job of hiding the effects of several hours of yard work as he played with them.

By the time he was in need of a break, they had attached themselves firmly to him. They were more than willing to suspend the horseplay to be wherever he was.

Their father may have been stingy with physical shows of affection, but that had not affected their appetite for it. When he collapsed onto a lounger, they found ways to squeeze on with him. Mike unabashedly straddled one thigh. Teri used her hip to convince him to move as far to one side as he could.

"God, Nancy! Was I as brazen as Mike when I was that age? Look at her! It's like she's trying to get herself off on his leg!" Rebecca was staring at the way her youngest was sitting on Sean.

"I tell you what, Rebecca. If I was sitting like that and he flexed those huge thigh muscles, I'd go off like a rocket," Nancy mused.

"Nancy!" Rebecca exclaimed too loudly, then giggled softly.

Having never spent any time with pre-pubescent girls, Sean was amazed and delighted by turns.

Considering himself an energetic person, he was amazed at the vast amounts of energy the pair had expended in the pool. It had not taken him long to discover that the more physical he was as they frolicked, the better they liked it. When they were playing, he could definitely see the little girl side.

Now, as they sat chatting, the thirty-year-old side showed up, just as Nancy had joked. Both Teri and Mike could look at him and he would see all of the worldly wisdom and sexual prowess of Nancy and the others. He thought immediately of Claire, with her all-knowing, lustful smirk. How could girls who had not reached puberty be so damned sexy?

As they were resting and chatting after the strenuous play, he got a glimpse of the girls' active, agile minds. As they talked, he really could not detect an age gap. Of course, their current experiences were different, but they asked about his life with apparently genuine interest. Several times, there were evidences of surprising knowledge of current events and issues.

When his first rather brief visit with the girls ended, he was honestly looking forward to the next time.


For Sean's first time with the girls, Nancy and Rebecca had been by the pool, but they only watched.

During the second play time, Sean got in a well-braced stance and tried very hard not to move at all as the girls jumped and pushed, trying to get him off balance.

Nancy and Rebecca were unable to resist when the girls suddenly left the pool, ran to them, and dragged them to their feet. "You have to help us with Sean," Mike insisted. "We can't move him."

Once in the pool, the women were, of course, very reluctant to wrestle the way the girls were. "You two aren't helping at all!" Mike complained after a few perfunctory shoves were the women's only contributions.

"I think we had better get serious, here," Nancy whispered in Rebecca's ear. "We can make big points with the girls."

"But..."

"Honey, forget about Jason and his shit, for once. Just be a girl again for a little while," Nancy insisted, then followed her own advice.

Something snapped in Rebecca. Later, she would not believe that she had really done it. With a shriek the equal of any the girls had released, she leaped at Sean. She was in front of him, and she used her hands on his shoulders to push herself up. As her charge carried her forward, her lower belly, just above her swimsuit bottom, pressed against his face. With nothing behind him to brace against, her weight and leverage did the trick and he went over backwards. As he sank, he made sure that she came under with him, and he held her down for quite a while. Even under water, they could hear the girls' delighted shrieks.

That set the tone for several minutes of very unladylike roughhousing. Eventually, they all got out, breathing hard. The girls, of course, were still dancing around, ready for more. Rebecca could not help it. She unconsciously held Sean's hand as they plodded to the loungers.

When Sean had left, the women went inside to fix dinner. "He has that effect on you, doesn't he?" Nancy prodded.

"Huh?"

"Sean. I saw you take his hand. It is just so natural."

That made Rebecca sniffle. "I guess if you don't start a relationship with those feelings, it's really hard to grow them later," she lamented. "Jason and I had plenty of bedtime lust. I thought we were in love. After all these years, I'm discovering some things that were missing."

"Look, Honey, I've said it before; if you need it, I'm sure the Gang would let you have one of the men for a while."

"You know I can't do that, Nancy. The idea sure is tempting, though. They must treat all of you very well."

"You know, of course, that Sean is still a virgin," Nancy explained. "It is a given that Carole will be his first."

"Nancy! You can't mean..."

"When he gets free of his mother, who knows what will happen."


When Sean had done a basic back massage on all of the women, they started over with Carole, moving down over her ass and her legs. Both Sean and Phyllis thought that when he first worked Carole's ass, he would ejaculate all over her. Somehow, he held it. His control increased with more practice.

The next Sunday, the brunch discussion was very lively.

 
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