Gang of Five - Cover

Gang of Five

Copyright© 2009 by Shrink42

Chapter 19

Romantic Sex Story: Chapter 19 - 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  

From her first day at the club, Arlene should have been getting massages. However, Rebecca and the Gang had decided that only Dan should touch her. At the beginning, things were too strained for that level of contact.

Since committing to make the marriage work, Dan had foresworn any more intercourse with the Gang, and they understood and agreed with his thinking. Instead, some lunch times had been used to teach him massage. Thus, when Pip stopped in one afternoon and set up a massage table and an assortment of oils and such in the family room, Dan was ready.

After much discussion, it had been decided that it did not make sense for anyone else from the Gang to show up naked at Dan's. Pip was an interesting choice for a couple of reasons. She was very familiar to Arlene from the club, and she was an impressive physical specimen.

Naturally full-breasted, narrow-waisted, and bubble-butted, Pip was approaching the level of muscle development needed for competition. With all of that, she was not at all mannish in body or face. What Phyllis thought would have a particular impact on Arlene was Pip's crotch. Because of thinner, looser labia and a wide separation between her thighs, Pip's bare pussy just seemed more exposed, even more 'obscene' than Phyllis's.

Arlene appeared to be even more afraid of Pip than of Phyllis. When Pip arrived and stripped, Arlene was badly shaken, probably anticipating that Pip would stay. Stay she did. For the couple of hours before Dan was due home, Arlene was a nervous wreck. Julie and Pip did their best to ignore it, but Julie finally pulled Arlene into the master bedroom for a little lecture.

"Now, Honey, you know Pip. She is a very nice woman who has helped you a lot at the club."

"But she's so..."

"Arlene, Honey, who is in charge of what naked women Dan sees? It's not you, is it? You know what it will take before you have anything to say about whose pussy he looks at, don't you?"

Poor Arlene's face was disintegrating like a child trying to keep from crying. "How ... how many more?"

What a perfect set up! "Until you can show that you understand Dan's right to have naked women around."

It took a while, but Arlene's pathetic look gave way to first contemplation, then determination.

It was the first time with two other naked women. Dan had been warned, but had not met Pip before. Conversely, Pip had been coached on how she should react to Dan. In fact, it had taken some fast talking to get her to go along with the plan. Her honest reluctance and modesty worked beautifully when she was introduced to Dan. She did not have to fake any blushes. Although it must have taken everything she had, Arlene actually explained to Dan how Pip helped her at the club.

That was not the end of the pressure for the night, though. Just before dinner, Phyllis arrived, apologizing for not getting there earlier as she stripped. After dinner, Pip pled another commitment and left.

Not a word was said about the massage table until after the news. Then, Dan spoke up. "Honey, you must have had some soreness from your workouts all this time. I've been learning massage, and tonight, I'm going to make you feel better. The family room setting and the presence of both Julie and Phyllis had been chosen purposely to reduce the 'threat' of foreplay. In Arlene's mind, that could only occur in privacy and secrecy.

That did not necessarily make it easy for Arlene. Julie felt that she had been quite successful lately in minimizing those pathetic expressions that Arlene could turn on. Dan's instruction to get on the table brought the expression back. Julie just gave Arlene an expressionless stare while Dan guided her to where she should be.

Julie could not help crying. Dan stuck strictly to Arlene's back. He did such a good job that she fell asleep. When he saw that she was out, Dan kissed her softly on her exposed cheek. It was such a tender moment and such a statement about the triumph of love that Phyllis's eyes did not remain dry, either.

Between the three of them, they decided it would be better for the women to get Arlene into bed. Rather than put her through the awakening affects of a shower, Julie just wiped the oil from her back and they got her in bed while keeping her very, very drowsy.

When they returned to the family room, Dan was sitting on the couch with his head back, his eyes closed, and some obvious tear streaks on his face. Julie saw Phyllis kneel in front of Dan and almost as if rehearsed, she snuggled up to him and spoke softly into his ear "Don't object, please. You need this."

By the time Phyllis got him exposed, his cock was fully rigid. As he was approaching ejaculation, Julie kissed him and said "You can't imagine how much I want to do that myself." Suddenly, he was there.


As August passed its midpoint, the beginning of school loomed as the next big event. For both Sarah and Sean, it was something they had both been preparing for. Sean had been preparing for nearly five months. Although it had been only about five weeks for Sarah, her prep had been extremely intensive.

The next time Sean was scheduled to spend the night with Phyllis, he came in from working on her yard to find her chatting with a man who was obviously someone she knew quite well.

"Sean, this is Walt Cherney, the wrestling coach at Addison University. He is just joining me for a casual dinner to talk about old times. It is just a coincidence that you were working here today." Both men saw the broad, grinning wink.

After some getting acquainted, they sat down to eat and Walt told Sean "The last thing I want to do as make real, competitive wrestling seem anything like the TV version. I do think, though, that it is a good idea for a potential champion like yourself to establish a personality - an image - when he is on the mat."

"Potential champion?"

"Of course, Sean," Phyllis said. "It is what we have aimed at from the beginning."

"Y ... yeah, you're right. Mr. Cherney I'm not sure what you mean by a personality."

"OK. Let me give a couple of examples. Maybe you can be like a greased pig. No one can get a good grip on you because you are so good at avoiding and escaping potential holds.

"Or maybe you can be a cobra. You are constantly bobbing and weaving, looking for the perfect place to strike. Your mat personality is what your opponents will expect when they meet you."

"But wouldn't that make me predictable?"

"Perhaps, but that isn't always bad. From what Phyllis has told me, your competitive edge will be conditioning and endurance. You should be able to outlast anyone. By the way, between workouts and work, you are already doing as much as college wrestlers. Keep it up."

"OK. So what does that mean about my 'mat personality'? What specifically should I do?"

"I think you should become the 'irresistible force'." Sean nodded uncertainly and waited for an explanation.

"As soon as the match starts, you should be in motion - offensive motion, attacking motion. Never, ever stop working for an advantage; a better hold; more leverage; a way to escape."

"But isn't that what all wrestlers do?"

"You would be surprised how many seconds you spend just holding from on top or holding still from the down position. I'm not saying that you should waste energy uselessly trying to escape from down. Just make your opponent think that you are about to pull an escape. Make him tire himself holding on more firmly."

Phyllis entered the conversation there. "Part of the reason I want you well within the weight limit is so you can have a little extra energy. You won't waste anything sweating off the last pound before the match just to make the weight."

Sean sat quietly for a while. "I guess that's a lot different from the way I have been wrestling."

"We want everything about you to be different this year, Sean," Phyllis said. "The way you competed last year will not get you the championship."

"You know, Mr. Cherny," Sean said, patting Phllis's had affectionately, "it's interesting how Phyllis and her friends want that championship at least as much as I do."

"Son, listen to them. A lot of people, even athletes, never learn how to go after something important with absolutely everything they have. If you can do that even once in your life, you will be changed. It isn't even the success that changes you. It's giving your all."

"Hmmm. Tell me some things I an do to build that 'irresistible force' image." The next hour was spent in a lot of fairly detailed wrestling talk.

"Sean," Walt said as he prepared to leave, "some of my team get together on their own for casual competition two or three times a week. My coaches and I stay a long ways away to avoid any NCAA problems. I've never invited a high school student before, but I owe Phyllis big time. Here's who you should call. They will expect you."

"But how will your college guys feel about me butting in?"

"Well, be prepared to be given some harsh lessons. They will be very careful not to hurt you, though."

When Walt had left, Sean asked "Do you think I should do that?"

"Let's see," she said dramatically, "how hard will it be compared to dancing naked with those nice girls?"

"Irresistible force, huh? Like the tide, maybe?" was his answer.

Three days later, Phyllis drove Sean to a grade-school gym near campus. When he came out ninety minutes later, he flopped into the passenger seat and moaned "I hope your massage table is up."

"Some pretty strong guys, huh?"

"Oh, that wasn't the problem," he answered. "It was their speed! And their aggressiveness. They were all doing what Mr. Cherney wants me to do."

"That's the way he coaches. I'll bet he's hoping you will be on his team someday."

"If I live that long."

"Come on, Sean! It's just like dancing naked with the girls. When you got to the dance, it was no big deal."

"So if I get used to wrestling with these college guys, no one in high school will scare me, right?"

"Smart, too. It's not against any high school league rules, but I think your workouts with the college guys should not be mentioned at school."

"Good idea."


It was the third week of Sarah's 'project' and the second week since Julie had 'taken over' Arlene. As they sat on the patio after dinner and watched the girls try to rid themselves of some excess energy, Nancy asked Rebecca "Would it be alright if I took the girls with me to Julie's to stay with Sarah tomorrow. All of the others seem to be tied up."

"Oh. How will you explain Sarah being naked?"

"I think you should do that, Rebecca. Oh, and tell them whether or not they can undress. If you let them, be sure to tell them if they have to dress when Troy and James, the dance instructor, show up."

"NANCY!"

"Rebecca Tate! What happened to 'normal and natural'? You know as well as I do that when they hear Sarah is naked, they will want to undress here and drive over that way."

"But ... but with the men ... Damn! I know, I know - normal and natural. Maybe I should never have told them that. OK. I'll tell them, but right here where you can be in on it."

When the girls had wound down enough to pay attention, Rebecca called them over. "You know how you were so impressed with how relaxed and confident Sean was, Girls? Well, Julie's granddaughter, Sarah, is doing the same kind of project Sean did." Rebecca described what Sarah's life had been like and what they were all trying to do to give her a Cinderella senior year. She also mentioned that Sarah looked much younger than she was."

"Wow! I'd like to meet Sarah," Teri exclaimed. They asked a number of questions, and were properly amazed to hear about Troy and the dance instructor and all of the men coming for dinner.

Rebecca could see Mike about to ask a question and pre-empted her. "If you want, you can be naked with Sarah." That scored the hoped-for impact.

"What about when the guys are there?" Teri asked. "Will they be naked?"

"Sorry, no."

"Do we have to dress, then?" That was Mike, of course.

"You mean you want Troy and James to see you?"

"Well, I sure like it when Sean sees me." Mike used the belligerent posture that she adopted so often.

"Well, Troy is a super-nice guy, almost like Sean," Nancy interjected. "He's built a lot like Sean, too. He has three sisters, so I don't think you would shock him. James, the dance instructor, is a nice guy, too. He is just not interested in girls' bodies."

"Huh? You mean because we don't have boobs or hair?"

"No. We've talked about it, Honey. James is gay," Rebecca answered.

Both girls were thoughtful for a moment, then Mike grinned and declared "If Sarah can do it, we can do it. Maybe we can change James' mind." Teri looked more than a little shocked, but getting dragged into things by her younger sister was becoming a trend. She dared not back down.

As it turned out, Sarah was no more immune to the charms of Rebecca's girls than was Sean. Nor were Troy and James. The girls managed to entice both guys into the pool, although suited, and subjected them to the same assaults and high-energy play that Sean had experienced. Their own nakedness seemed completely irrelevant to the girls.

There was an unexpected development. In the course of conversation, Sarah mentioned Claire's lessons on poise and grooming. Teri and Mike insisted on calling their mother at the office and demanding to be included in those lessons. Although it took a little more careful scheduling, Claire was delighted with the idea. As Sean had discovered, there was no feeling of being with little kids when Sarah was with the girls.

For the rest of Sarah's project, she had naked company a number of days. The Gang decided that the objectives of the project were not compromised at all.


About two weeks before school was to start, Dan was experiencing a low point. His feelings toward Arlene were definitely changing, but she seemed to be at a plateau. There had been no breakthroughs for a while.

Nancy had a plan to break Dan from his little funk. She told him to come to her house at eleven and plan to be away from work until at least two. The much harder task was to get Rebecca there at the same time and under Nancy's conditions.

When Dan arrived, he could not miss the noise from the pool area, mostly from the girls. Before he could see the source of the hilarity, though, Nancy pulled him into the powder room, undressed him, and got him off. Then, shedding her own clothes, she led him to the patio door, despite his protests about the girls. At that moment, Sarah met him, naked, and helped Nancy tow him out to the pool.

The one thing that helped Dan the most was to see Rebecca there, as naked as he was and just as nervous as he was. Rebecca introducing him to the naked twin tornadoes did little to ease his mind, but they were so utterly captivating that he could not bring himself to protest. When Sean, naked, moved up between Rebecca and Nancy and casually put an arm around each of them, Dan nearly shorted out.

"Dan, unless I miss my guess, you have been through about what I have with the Gang. This should not surprise you. If it's any comfort, I think Rebecca is more upset than you are. I cannot believe Nancy talked her into this."

"All it took was threatening to throw her out," Nancy joked. "She doesn't have anywhere else to stay tonight. My house, my rules."

Dan had always felt a little competitive toward Rebecca, partly because she had encouraged those feelings. He managed pull himself together enough to give her a complete appraising look, then said "At least as good as I imagined, Dr. Sanders."

Rebecca blushed brightly, struggling mightily to keep from covering up. That was not from competitive feelings, but from a desire to personally match the demeanor she had coached him on. Finally, she gave him a girlish play slap on the arm and chided "I thought we got rid of the 'Dr.' nonsense a long time ago, MR. CASHIEN."

Dan was not used to the kind of play that went on in the pool, but as in all other instances, the girls, with eager help from Sarah, overwhelmed his qualms and got him into the pool. He froze when Sarah jumped on his shoulders to meet a chicken fight challenge from Mike atop Sean. Rebecca was right there to tell him "Just go with it, Dan."

That brought the competitiveness back, and he retorted "As long as you're my next partner." That left Rebecca speechless. Only after she had ridden Sean against Sarah on Dan was Nancy able to browbeat her into swapping.

Later, Dan and Rebecca were side by side on loungers, and she was able to ask him "Feeling guilt again?"

Dropping any competitiveness, he answered thoughtfully "Well, you were right back then when you said we were potential mates. "With your, uh, your..."

"My pussy, Dan. Just say it."

" ... with you pussy against my neck while I'm trying to rebuild my marriage..."

"I think you know that I did not want to do that," she consoled him. "As much as I have counseled Nancy and the Gang, I have to acknowledge that their instincts are seldom wrong. It felt damn good, Dan. The problem is that I need a good fucking so badly it is driving me crazy. I suspect that you feel the same way since you have stopped with the Gang. Just to get it out in the open, you and I can't do it, no matter what Nancy or the others say. Do you agree?"

"Very, very reluctantly."

"Damn, I taught you too well, Mr. Alpha Male. It would cause more problems that we could handle, though."

"Yeah, I know," he said softly. "I respect your need to keep some level of professional detachment. With the Gang, at least there is the generation difference to make things seem more therapeutic and less romantic. Do you have anyone? Forget that. It's none of my business."

"Sean. Just a couple of times when I first found out. Generation distance there, too."

He looked over at her and he met her gaze. "Thank you. You certainly didn't have to tell me that. I'm not going to promise to call you if my marriage fails. I'm not going to let that happen. I can honestly say that I have come to love you, though."

Rebecca teared up at that. "The two men who have told me that recently are men that I can't have. I've come to love you, also, Dan. In my practice, you will always be an example of a man who went way above and beyond to save his marriage."

"Your girls are really something," Dan changed the subject. "I'm afraid seeing them makes me feel bad for for how much of the joy of being a girl Sarah missed."

"Forward, Dan. You can only afford to look forward, now," Rebecca encouraged. "I know that this is a bit of a low point for you, but this WILL work. Progress may be by spurts and pauses, but there IS progress."

"Yeah, I know. I can see differences," he admitted.

"Has this little outing been good for you?" she probed.

"I think seeing Sarah so free and confident is the best part," Dan answered. "I have to keep reminding myself that giving her a chance at a normal life was the first priority. Look at her! I guess you've heard all about fathers lusting after their daughters, but how can I help it?"

"You can't help it, Dan. If you didn't have those feelings, you should be concerned. The trick is how you deal with the feelings, and you are doing just fine at that. A healthy, loving relationship between father and daughter is a good thing. A daughter's crush on a dad who deserves it is the best preparation for choosing the right life mate."

"Thanks, Rebecca." Noticing her silence and a sad look after that statement, he just kept looking at her with a questioning expression.

She noticed and gave a big sigh. "I never felt that. He definitely did not deserve it. The result - a divorce. You are one of the lucky ones, Dan, because of your parents. Sarah is lucky, too."

"Well, I came close to blowing it. If Mom hadn't shaken me up..."

"But she did. I have to tell you, we have something planned for Sarah's last week that is way beyond what she has already been through. I think you should wait for her to tell you about it. She doesn't even know, yet."

"Afraid I would say 'NO WAY'?"

"That would probably be your first instinct."

"Then I will wait for her to tell me. Rebecca, I have to tell you that I trust you. You would not allow anything that was not good for Sarah."


It was good that Dan did not know exactly what was planned for Sarah. It had all started when Rebecca expressed a concern. "Sarah is doing remarkably well. The only problem that I see is that in the whole project, Sean is the only true contemporary that she has been with."

"Maybe we should get some boys from Lindsey's to come out," Claire suggested. "Kind of like we did with Sean."

Carole sat bolt upright in her chair. "I've got an even better idea! How about if we arrange for her to spend the rest of her time before school at Lindsey's. They have naked boys or girls serving 'sentences' there periodically. The other kids are used to it."

"Wow!" Nancy exclaimed. "That's ... that's ... Could she really handle that?"

"Just like Sean, I think she is at the point where she is so happy with the changes in her life that she won't refuse anything," Rebecca answered. "That would be an extreme test, though."

"One problem is that I hate to see her missing her workouts, her sessions with Claire, and everything," Julie pointed out.

Now, Rebecca shot right to her feet with sudden inspiration. "Why would she have to miss them? Claire, how about if you did your sessions there and included any resident girls who were interested?"

Not missing a beat, Claire asked "How many days would I have?"

"I think all of the schools start on a Tuesday. How about if you started the second Saturday before? That would be ten days," Carole suggested.

"Well, it would not be the best way to 'finish off' Sarah, but the other benefits to her would be great. I would have to do sort of a summary course to help the other girls."

"You could spend more hours each day than you do now with Sarah. I'll bet the resident girls would eat it up," Carole said. "Oh, would this interfere with your schedule, Claire?"

"Nothing I cant' rearrange. Do you think the Lindsey's management would support this?"

"I think they would love it," Rebecca assured her.

"Would we have Troy and James go there for Sarah's sessions?"

"I'll pay them for extra time to help all of the kids. I suspect they have good help with workouts," Phyllis said. "Maybe they won't need Troy. James could give lessons to girls and boys. He can use the money."

"I don't know, Ladies. Every time I think I have seen everything from you, you come up with something even wilder," Rebecca exclaimed. "Let me see what I can set up."

Several of the boys who had served the naked brunches to the Gang about a year earlier still lived at Lindsey's. A couple of others had returned just to greet them. When the whole Gang plus Rebecca walked in for the lunch that Muriel had set up, there was quite a round of joyous hugs. Fortunately, a time of catching up had been included, so lunch was not really delayed.

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