Gang of Five
Chapter 10

Copyright© 2009 by Shrink42

Romantic Sex Story: Chapter 10 - 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  

While Sean had been meeting Rebecca's girls, working out fanatically, completing school, getting more and more into his new business, and taking the final step in winning freedom from his mother's stranglehold, the Gang had launched the 'Dan Project' at full speed. They had made sure that Sean knew nothing of this new involvement. They did not want anything to distract him. Besides that, what they had planned for Dan was more than Sean was ready to hear about.

It was the Monday after Sean's first dance that Julie voiced her concern about Sarah and about Dan's marriage to the others. The Gang started working on her immediately and mercilessly.

It took a whole week for her to work up the courage, but the following Monday, Julie nervously followed up on the plan the Gang had finally gotten her to accept. She called her son, Dan, and asked him to come over after supper. Even though she gave no reason, he agreed.

He was so busy wondering why she had called him that he did not question why she stood behind the door as she opened it for him. When he was inside and she shut the door, he could see that she was naked and trembling.

She let him stare open-mouthed for a few moments, then said "Let's get in the hot tub, Danny, I've got something really serious to talk to you about."

He hissed in surprise and stood frozen. The Gang had discussed his possible reactions, and she quickly undid his shorts and pushed them and his underwear down.

"Mom!" he objected, grabbing to pull his pants back up.

She was not strong enough to have stopped him, but when she took his hands in hers, he quit trying to cover himself. "What's going on, Mom? Why are you doing this? We've never..."

"I probably should have done this when I looked a lot better," she told him, lifting his golf shirt over his head, his shorts and briefs still around his legs. "We need to talk about some stuff where being naked will let us communicate better."

"Communicate better? I don't know if I will be able to even talk!" he complained.

She knelt and took off his sandals, then helped him free his legs. Standing back up, she looked him up and down and smiled. "I done good, didn't I? You've kept yourself in good shape, Honey."

"Me? What about you, Mom? You sure don't look like you're ready for Medicare."

"Danny! Don't go skipping any years like that. Besides, just how bad is sixty-one supposed to look?"

"I guess your friends know what they're doing with the exercise and nutrition, huh?" he commented.

"They are all brilliant women. They know what they're doing about a lot of things. Us standing here naked is part of a plan that they worked out," she admitted.

"Why? What's to important that you had to... ?" and he just gestured at her nakedness.

Taking his hand, she said "Let's talk in the hot tub. I think we will be more comfortable when we're less exposed." He looked around nervously as they crossed the part of the patio that was not completely hidden from a couple of other houses.

"Is this vacation trip a last-ditch attempt to save your marriage?" she demanded as soon as they were seated in the tub.

He just looked at her long and hard before his shoulders sagged and he admitted "For me it is. Of course, she doesn't see that we have a problem except for my demands for sex."

"Does she give in to those demands?"

"Only very occasionally."

"How many times in the last three months?" she asked, hoping that she had not gone too far.

"I don't think I should talk about that," he objected.

"Look, Honey," she scolded, "I think you've been refusing to talk or think about a huge problem for a lot of years. I think you can remember from when you lived at home that your dad and I had big sex drives."

"Th ... that was no secret," he admitted.

"So," she went on, "either you did not inherit your libido from either of us, or you're just suppressing it to stay with your wife. Or maybe you've found another outlet."

"Mom, I've stuck to my wedding vows."

"And just done without," she countered.

"Pretty much," he conceded.

"How often do you relieve yourself? How do you keep it from Arlene?"

"Mom! What the hell is going on? We've never talked about this stuff!"

Julie sighed heavily, then looked up at her son. "I'm going to tell you the whole story. You can stop anything from happening, but I sincerely hope you can see how important this is. I'm very concerned about Sarah"

"Why, what's wrong with Sarah?" he demanded, concern showing.

"It is not right for a high school senior to be as completely ignorant about sex and male/female relations as your daughter is. She could be vulnerable to some smooth-talking jerk and either get left pregnant and alone, or end up in a lousy marriage. It happens over and over to unprepared girls, Dan."

"It's not that bad, Mom. It cant' be. Sarah's such a good kid."

"Oh, she's a wonderful girl. But she has hormones. Somehow, all of those hormones have been held in check, but what happens when they finally break loose. They will, you know. It's inevitable. Poor Sarah won't have a clue how to react."

"I guess you have a plan to try to cure her ignorance?" he asked skeptically.

"It can't be cured overnight, Hon, but I want to start. I really love that girl, you know."

"Yeah, you two have always had a special connection, haven't you?" he responded.

"I want Sarah to stay with me while you go on vacation. There is an absolutely wonderful young man who has been working for all of the women in our little group. He is younger than Sarah, but he is so thoughtful and respectful. Besides that, he is a wrestler and has a very nice build.

"My plan is to have him working on a major project that will keep him around while Sarah is here. He will understand my concerns about her and will try to help her come out of her shell and dispel some of her ignorance."

"And just how will he be 'dispelling her ignorance?" Dan asked testily.

"Dan, how much experience with boys should a well-adjusted high school senior have?"

"We don't want her doing things just because all of the other girls do," he said firmly.

"Did you mean 'we don't', or 'Arlene doesn't'? Would you want Sarah to end up just like her mother, making some other man as miserable as you are?"

"I never said I was miserable!"

"Some things, a mother can just tell."

"OK, so you want to help 'educate' Sarah. From that, how did we get to all of these questions about my sex life?" he asked.

"In a week or so, I could only make a small start at reducing Sarah's shyness and building her confidence. What happens when she's back under Arlene's iron fist?"

"Mom, you make Arlene sound like a monster! She's not."

"No, but in the area of sex, she is dangerously misguided. Tell me, Hon, what would happen to Sarah as she is right now if she was away at college?"

Dan was very quiet, and after a long time with no answer, Julie exploded. "Arlene is not going to let her go to college, is she? She's going to keep her controlled and ignorant, isn't she? And you're going to let her do that?"

"Well, I..."

"Look," Julie said firmly, "You have a right to accept a life that is much less fulfilling than it should be. That is a decision you can make. As a mother, it pains me to see it, but as long as I know that it is your choice, I can accept it.

"But when you start passing the misery down to the next generation, it is very hard for me to accept. How often does Arlene orgasm?"

"WHAAAAT? Mom, that's going too far!"

"I'm serious, Son. I'm pretty sure you made girls come when you were younger, didn't you? You could tell how wonderful it felt for them, couldn't you?"

"Guess I didn't hide much, did I?" he quipped.

"Now, you don't have to answer me, but here's is my guess. You never made Arlene come until you were married. Then, after a few times, she said she didn't like it because she felt out of control. Is that about right?"

"Shit!"

"Is that the kind of life you want for your sweet daughter?"

"You know I don't, Mom. Do you really think Sarah is headed that way?"

"How many boyfriends has she had?"

"I guess she's never had one," Dan admitted.

"How many dates?"

"You know Arlene won't let her date."

"So, Arlene will make Sarah into a clone of herself, then," Julie said with exaggerated resignation.

Dan hung his head and shook it slowly. "Do I really let her run over me like that?"

"When it comes to Sarah, I'm afraid so," Julie said gently.

He was again quiet for a long time. "Sarah will be here during our vacation," he announced suddenly.

"It would be good if her cousin Jess could be with her," Julie said.

"Girls do things better in groups, huh?" he observed.

"Do you think the vacation will make any difference for you and Arlene?"

"After all these years, I'm afraid to be optimistic."

"Are you going to really try? Are you going to try to seduce her?" Julie asked.

"I ... damn, Mom! I shouldn't have to seduce my own wife, should I? Are you suggesting that I should just divorce her?"

"Danny, you're all grown up now. You get to decide what you want your future life to be like. You may decide that divorce is worse than near celibacy. You may decide that all of Arlene's other qualities make the lack of sex bearable. I can't answer those question for you.

"My concern right now is for Sarah. She isn't able to make good decisions for herself about those things. A girl should be allowed to deal with her hormones on her own with some loving guidance. She should not be like a puppet."

"A puppet. Completely controlled by her mother," Dan mused. "I can't honestly say what's going to happen to our marriage, Mom. I can tell you that we will be doing some serious fighting over Sarah dating. You scared me when you said she would turn out just like Arlene."

"That's great, Hon. I'll help Sarah any way I can," Julie assured him.

After saying that, she stretched both arms up over her head in a way that brought her breasts up out of the water. He definitely noticed, but did not attach any particular significance to it.

He should have guessed that it was a signal. Very shortly, Carole and Phyllis came walking out to the tub, naked. Julie had made sure that Dan was facing the house and it was still light outside, so he watched them all the way.

"Nice to see you again, Dan," Carole said casually.

"It must be at least two years since we saw you last," Phyllis added.

"Why do I get the feeling that this has all been set up," Dan was able to ask.

"Good guess," Carole said with a grin as she sat on the edge of the tub.

"We understand that live, naked female flesh has not been too available for you, so we wanted to help," Phyllis chimed in. "We thought of hiring some strippers, but we didn't really know any. The others decided that Carole and I were the least wrinkly and saggy of the group, besides your mom, so..."

She spread her arms and widened her stance, still standing at the edge of the tub. Her sturdy but well-proportioned and beautifully-conditioned body belied her nearly sixty years. Her fat, bare, tightly-closed labia gave away her own excitement by their slight darkening.

Without saying anything, Julie got out and went in the house. As she did so, Carole and Phyllis moved so Dan's view of his naked mother's retreating backside was not obstructed. When Julie entered the house, Carole stepped into the tub and straddled Dan's lap. Not saying anything, she pressed her torso forward against him, with her head on his shoulder and one hand feeling his fully engorged cock. Phyllis got in the tub next to Dan and put and arm around him.

The three were silent and still for many seconds before the women stood and grabbed Dan's hands. When they tried to pull him to his feet, his face flushed and he resisted.

"Come on, Dan. Just let us see your hardon. Of course, we can make it go away if you'd rather. We hoped that you wouldn't waste it just shooting off in the tub, though," Carole said as she reached down to fondle him briefly. "Both of us would like to feel that beauty up inside of us."

"C ... Carole! Don't!" Dan protested. "I c ... can't ... Mom..." The women knew that they had him at that point. He had not worried about being unfaithful, just about what his mother would see.

"By now, Julie is on her way to Nancy's house, so don't worry. She desperately wanted to be in on this, but we all decided that might be a step too far."

"What do you mean b ... by 'this'?" he quavered.

"For the next hour or so," Phyllis told him, "we are going to have as much sex as you are willing to give us." As she talked, she rubbed the back of his unresisting hand over her smooth crotch.

"I've never cheated," he insisted. Again, Carole was encouraged because he did not say "I can't cheat." She used some of the same words that she had used on Sean months before.

"Dan, you are a fine, virile sexual animal. It excites us women to be with such a fine specimen. You have had no chance to exhibit your full sexual prowess for a long time. We want to send you on vacation with memories of how life with a woman could and should be."

"Are you all trying to break up my marriage?"

"Only if that's what you decide is best for you. We just want to be sure you have all of the facts to make that decision. Now, come on. Stand up and show us. Please!"

Ever since his mother bared herself, Dan's muted objections and rather easy compliance had shown how desperate he was for sexual activity. Truth be told, he had nearly erupted from Carole's quick assessment of the size of his erection. That was not like him at all. Resisting their tugs for only a moment, he gave up and stood. He could not look either woman in the face as his cock bobbed in front of him with his heartbeat.

It would have been impossible to completely script an encounter like theirs, but the group of women had talked about several options at different stages. It was apparent that Dan was very close to ejaculation. With just a few strokes, they were sure that he would release.

If he came, though, the pressing arousal would be relieved. In other words, more blood could get to his brain. If he thought too much about it, he might refuse to proceed further. With a discreet signal, they guided him back to sit on the edge of the tub.

Phyllis straddled him with her back to him. Carole knelt and held his cock as Phyllis let herself down onto him. Just the excitement of their exposure had aroused her enough so she was plenty moist for insertion. As Phyllis was working herself down onto him, Carole squeezed the base of his cock, hoping to stave off his climax for just a while. She succeeded enough so that Phyllis was able to use her strong legs for several strokes before he let loose with a groan. The groan was partly for his amazement and chagrin at how quickly he had come. Early ejaculation had never been a problem for him. Quite the opposite was true, in fact.

The scenario just played out was actually the preferred one that the women had devised. It had the huge advantage of getting the issue of penetration - of actual adultery - out of the way quickly. The deed was done. Now, maybe they could get him to enter into some more sensual activities without the issue of faithfulness being such a roadblock.

In their group, Nancy and Phyllis were blessed with the most impressive breasts, other than Julie. For that reason, Nancy had almost been included. It was decided, however, to go with the two whose bodies overall showed the fewest effects of age. Making Dan's marriage situation even more cruel, Arlene had a very fine figure, well proportioned and not overweight.

The plan was for Carole to pull his face between her breasts at the time when remorse might set in. Just a glimpse of the competing emotions on Dan's face made it easy for her to wrap him in the classic comforting hold. He really was a good man, deprived and conflicted.

Carole held him until his breathing steadied. None of the three said a word as Phyllis pulled off of him. At yet another signal, the women sat beside him on the tub edge. Carole took his shaft in her fingers and Phyliis gently cupped his testicles.

In a contemplative voice, Carole mused "One of the things I missed the most from my marriage is this privilege. I could sit and hold his penis for hours. Most nights, I fell asleep with my hand around him."

"I miss that, too. It got so it was as natural as holding hands," Phyllis added. "We women are fascinated by our men's sex organs They represent something vital to us as women, and we love to touch them. It's possessive in a way, but loving, too."

The women could hear him start to say something twice, then just close his mouth. Finally, Phyllis said softly "Arlene doesn't touch you, does she?" He just hung his head.

Carole got in front of him, spread his legs, and knelt. She quickly leaned over and took his almost-limp shaft in her mouth. He stiffened and hissed, but Phyllis took the moment to press one of her distended nipples into his gaping mouth.

"Shhhh, Honey," Phyllis cooed softly. "Just relax and enjoy it. Bet it's been a looooong time since you felt a mouth on your cock, hasn't it?" He could only groan in response. She kept one hand holding his head to her breast while her other hand teased one of his nipples.

In a surprisingly short time, Carole stood up and tugged on Dan's hand. "Let's go in the house," she urged him. He stood up to their combined leading and looked around almost frantically for a towel. They just pulled him toward the patio door.

Once inside, slow dance music was already playing and Carole plastered herself to him and literally willed him to dance. She could feel him try to pull back as his cock bumped into her belly. Not having any of that, she pointed the shaft upward and put one hand on his ass to keep them pressed together.

"Dan, women love the feel of a cock that they've made hard. Don't try to keep it away from me, please." After another minute of dancing, she said "You know, you should be proud. For a forty-year-old guy's cock to stand up at such an angle is really great. Usually, it's just teenagers who do that."

When one song finished and another started, he seemed to become more aware and started actually dancing. Of course, bare feet on carpet is not ideal, but the feel of naked bodies moving in rhythm together overwhelmed any other feelings.

Midway through the second song, Phyllis pressed herself to his back left side, wrapping one arm around him and the other around Carole's upper back. Her bare crotch moved against his butt cheek, and her breasts were against his rib cage.

Sensing that his arousal was reaching the critical point and not wanting to waste his erection, Carole broke up their dance and both women led him to the bedroom. The next part was critical.

In the bedroom, the covers were already thrown back, and Carole fell onto her back, pulling him down with her. She pulled his cock right to her opening and Phyllis used her considerable strength to make sure he got on top of her and entered her. Consciously or subconsciously, he must have wanted to be in her because there was almost no hesitation.

The Gang had decided that a key to the whole encounter was to show him women eager for sex and unashamed to go after it. Carole did not have to pretend at all. The sessions with the four men had removed any hesitancy or any false need for restraint. Furthermore, Dan had a nice body and seemed to respond well to them. She could not help feeling some natural sympathy for him, and a feeling of filling a need always added another element to sex.

As soon as she was sure that he was securely into her well-lubricated passage, Carole wrapped her legs around his thighs and began simultaneously thrusting at him and pulling him toward her in the way that only a female body can do.

The Gang had discussed what kind of words should be said during intercourse. After a lot of debate, it was decided that Carole should speak tenderly yet seductively, while Phyllis, as the 'cheering section', should be more crude.

"Oh, Dan, Dan, Dan! That feels just wonderful!" Carole exclaimed. She ran her hands over every part of him that she could reach, and told him "All of those wonderful muscles working so hard to make me feel so good! Mmmmmmm!"

Carole babbled on for a little longer and when she stopped, Phyllis began running her hand over his ass and down the crack to his sac. "You don't have to be gentle and considerate with Carole, Big Fella. If you try to fuck the shit out of her, she'll love it. She's still got her womb, so see if you can shove that gorgeous prick right up into it. Pretend you can still make a baby in her. God, it's nice to feel your ass muscles flex!"

Carole gave out a couple of little whimpering noises and shook a little. "We didn't expect you to take care of Carole first, this time, Stud. But you know what? She can come from fucking, the lucky bitch! When you pound into her, make sure you really mash her clit. That'll get her off, for sure. Hey, you're doing great! That's a lot of strokes without coming. Guess it helped that I took a load off of you, huh?"

The talk must have affected Carole even more than it did Dan. She began whimpering more and breathing very erratically. Rather than the smooth stroking and caressing of his back that she had been doing, she began grabbing and clutching spasmodically. That lasted only about thirty seconds before she she bowed her slender body and began flexing so hard that she threw him around. Her tremors were accompanied by a series of little whining grunts.

Apparently, her orgasm so amazed Dan that his own escalation was aborted. By the time she stopped shaking and pulled his face down for a torrid kiss, he had not come. She did not say any intelligible words for a while, just tried to suck out his tongue.

 
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