Gang of Five
Chapter 1

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

Desc: Romantic Sex Story: Chapter 1 - 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.

The other four looked at Carole with a combination of surprise and amusement. It was nothing new for the five closest friends to be naked together in the hot tub. Often, two or more were together in very minimal attire. Now, though, Carole was telling them to stay naked while they ate brunch after their soak in the hot tub.

"I turned up the heat a few degrees, so we should be plenty comfortable, and here is a pile of towels to sit on."

"Hey, I'm not complaining, or anything," Claire said with a little laugh, "but what's going on?"

"My turn to host, my rules," Carole answered, trying to feign a gruffness that did not work well at all.

As they ate brunch, the unaccustomed nudity kept the conversation less lively than usual, but no one chose to question Carole's reasons until they were all drinking coffee or tea afterwards.

"OK, Hon," Claire said without her usual ribald humor. "Retirement getting you down?"

"Maybe, but the reason for the skin show is just a little practice. I think we should all go to a nude resort," Carole told them.

"Go where?" Nancy demanded loudly. "You've got to be kidding!"

The five long-time closest friends, Carole Gruden, Claire Passault, Julie Cashien, Nancy Withers, and Phyllis Larson, were together for the Sunday brunch that was as near to a fixed commitment as the 'Gang of Five' had.

"We've talked a lot about this Transformations place," Carole said. "It's amazing how the nudity helps so many of those women. They come out completely changed."

"Yeah, but they all go in with big problems," Nancy countered. "We're not like that."

"No, we're not," Claire agreed. "We're just rich old bitches with no big problems except that we're so horny we can't stand it." Claire could always be depended on to describe things in the most 'earthy' way possible.

"But, I'm just not comfortable going naked like that," Nancy protested. "I'm not slim and trim like the rest of you."

All of the women were in their late fifties or early sixties. They were all talented, independent, financially secure, and physically in the best possible condition. Also, they were all sexually active, but not nearly as active as they would like to be.

Nancy was the most voluptuous of the five, sporting a classical hour-glass figure. While she no longer looked forty, few would have guessed her true age from looking at her. She carried more 'padding' than the others, but that only covered the firm muscles beneath.

"God, Nancy! If I only had your boobs, I would never cover them," Claire retorted. With a professional dance career on her rather long resume, Claire had a dancer's build. Her legs and ass were shapely and taut and her torso was slim and graceful. Her breasts were the smallest in the group, but still filled out her clothes nicely.

"But then they'd sag even worse," Nancy complained. Her breasts were large and very full and firm. That meant that they did not sag nearly as much as would be expected of a busty sixtyish woman.

"Think we can get laid there?" Claire asked, changing the subject.

"That's really not the objective," Carole responded, "but I suppose it could happen. The clientele at a lot of the nude resorts is mostly German, Dutch, and Scandinavian. Who knows?"

"Ooooh! Lots of uncut cocks!" Claire chortled. "And shaved pussies, too." She looked right at Phyllis as she said the last. Phyllis's crotch was permanently devoid of hair.

"Tell me why you think we should do this, again," Nancy pled.

If there was an actual leader of the group, it was Carole. "I, for one, want to crank up my sexual activity," she said seriously. "We are all sexually liberated, at least we would like to be." That brought a chuckle. "We can all be very proud of our physical condition, thanks to Phyllis and Nancy. I just think that if we can be even more self-confident, it will help us find men that can be good partners."

"You mean husbands?" Julie asked with a trace of worry.

"Oh, we've been over and over that," Carole answered. "Unless something has changed, none of us are really looking for permanence. Hey, while we sun on the beach, we'll have lots of time to talk about finding cocks. Are you all willing to go?"

"When is it?" Julie asked.

"Well, I haven't made any actual plans, yet," Carole admitted. "A travel agent I talked to said that there are often some unbelievable last-minute deals. I don't know if we're quite ready for it yet, anyway."

"I can't see how I'll ever be ready," Nancy complained.

Claire could not let that pass. Hugging Nancy briefly, she told her "Maybe if we spend enough time naked, you'll stop pretending to be so modest. We've seen those poor men staggering out of your house."

Amid some giggles, Nancy protested "But that's all private."

"So, build up that confidence," Phyllis interjected. "Let the men know what they're in for right up front."

Nancy was blushing almost dangerously, but it did not last. She soon started giggling with the rest of them.

"So, reading about Transformations triggered this new nudity kick, huh, Carole?" Julie asked.

"Well, mainly reading the comments of the women who have been through there," Carole answered. "Of course, being naked is just part of what goes on there, but it's the one part we can do. We're already into the diet and exercise parts."

"Hmmmmm," Phyllis mused aloud, trying to keep a straight face. "Since it's at my house next week, you all have to leave your clothes in the car." That lightened the mood considerably.

Rebecca Sanders had always felt closer to her aunt, Nancy Withers, than to her own mother. As a very successful family counsellor with a Ph.D. in Psychology, it was one of the failures of Rebecca's life that she could not seem to strengthen the relationship with her mother. That did not stop her from spending what time she could with her Aunt Nancy.

"So, what has the Gang of Five been up to lately?" Rebecca teased.

"Oh, Carole's on this nudity kick. She wants us all to go to a nude resort together," Nancy answered. "Last Sunday morning, she made us stay naked. She's been reading a lot about Transformations."

"You know, I have some connections there, Aunt Nancy."

"You do?"

"Yes. I've met with most of the management people, even Dr. Waxman, the director. I'm particularly fascinated with the section that Lindsey Hall, the country singer, set up. It's a place for good kids who have intolerable home situations."

"Yes, I've heard about that. Has it been working well?"

"Some of the stories of those kids break your heart," Rebecca said, "but the kids are great. They have a new life and they make the most of it."

Conversation drifted off to other subjects, but Rebecca had the germ of an idea.

"Well, hello, Rebecca. I haven't seen you in a while," Carole exclaimed as she opened the door to Nancy's niece.

After greetings and Carole's offer of refreshment, Rebecca said "Nancy told me about your nude brunch and your plan for the nude resort. I had a devilish idea."

"But Nancy's the most reluctant one of us," Carole cautioned.

"Oh, I know that. I can't say that I'm a big nudity fan, but I sure can't argue with the effect it has had at Transformations. Did you know that I have some connections there?"

"I wasn't aware of that, Rebecca. The place fascinates me."

"Maybe you should think about funding a scholarship at Lindsey's Place, Carole. I tell you, the kids I have met there are really special. Actually, I have a crazy idea involving those kids. How would you like to really shake up the rest of the Gang?"

"Especially Nancy, right?"

"Well, Auntie dear needs to stop pretending to be so modest." That caused the two to laugh together. "The kids at Lindsey's are very comfortable with nudity."

"You mean even the kids live naked?" Carole asked in surprise.

"Oh, no, but for various reasons, they are exposed to it quite a bit. How would you like to have some of Lindseys' boys serve your next naked brunch."

Carole just gaped at Rebecca, then exploded. "My God! That would be perfect! Oh, what a marvelous idea! Next Sunday is supposed to be at Phyllis's. I'll get her to switch with me. Can you stay a few minutes longer?"

After calling the slightly puzzled Phyllis and getting her to agree to the switch, Carole asked Rebecca "Why would the boys want to do this?"

"Well, after you fund a scholarship, I think they will be eager," Rebecca said with a grin. "Seriously, I have done one, and it is really a worthwhile thing."

"I guess you know that it won't strain me," Carole answered. "Will you set it up for me?"

"No, but I'll connect one of you with Lindseys' management."

"Say, Rebecca, could you set us up as a client - the whole gang, I mean? I guess you could list me as the official client," Carole asked.

"Really? I guess I could do that. Oh, wait. I'm Julie's client for taxes and some other things. I'm concerned about conflict of interest, there. Hmmm. There must be other counsellors that have reciprocal relationships with patients. I'll find out, but assume that you're on."

"Good. Bill us for whatever time you spend contacting Transformations for us."

"Uh, Carole? What kinds of things will you want my help with?"

"I can't tell you right now, Rebecca. I do know you that somehow, I want to find some reliable men as regular sex partners. I think the other women want the same things. As you can tell, I am fascinated with the use of nudity, too. Overall, I'm just - antsy, I guess. Not handling retirement as easily as I would like. If those things make you uncomfortable..."

"Hmmmm. You are certainly not talking about the normal family counseling that I do. Well, maybe it's a good thing that I extend my, uh, boundaries a little. I'm starting to feel a little hypocritical doing marriage counseling, anyway, when I can't fix my own."

"It always takes two who want to fix it, Rebecca," Carole said softly. "You, of all people know that."

"I assume Nancy has told you all about it?"

"I doubt if she has told us everything she knows," Carole answered, "especially if you asked her to keep it secret. By now you must know that it won't go any farther."

"Yes, I know that. Actually, it's a relief to have someone else know - someone who cares. Carole, I'm looking forward to talking with you and the Gang about some unconventional things."

"We're always happy for chances to get the kids out into other social situations," Muriel Renfrew, manager of Lindsey's told Carole over coffee at Lindsey's. It was late on a school morning and no one else was around. "I have to say that this will be the most unique outside contact ever, though."

"But will they be able to do it? Will they enjoy it?"

"They will love it," Muriel assured Carole, "and by the time they leave, I'll bet the women will love the boys, too."

The next Sunday morning at Carole's, it took several minutes after coming in from the hot tub before Claire asked "Hey, Carole, how come you haven't started fixing anything yet?"

The timing could not have worked out better if Carole had scripted it. Almost before the question died on Claire's lips, the doorbell rang. As relaxed and comfortable as they had all gotten by that point, the threat of someone new discovering their nudity made them all react defensively.

"Funny you should ask, Claire. The caterers are here with a special brunch," Carole informed them, somehow keeping from laughing at how well she had put one over on her friends. Actually, it would have been hard to laugh when her own stomach was tied in knots. She had set this up, and for that reason, she would somehow act in control. The idea of baring herself to four teenaged boys, though, was more frightening than she had anticipated.

"Caterers!" came from Nancy, Claire, and Julie almost in unison. Phyllis looked surprised, but ended up with a little grin.

"Yes, caterers. Now, listen to me, and don't anyone dare leave. Our meal this morning will be served by four very nice high school boys. Nancy! Stay right where you are!" Carole almost never used any kind of commanding voice, and mostly because of shock and surprise, the others all froze.

"These young men are very used to naked women, and they will be completely at ease. WE are mature, confident, worldly women who all have the best bodies we can have. WE WILL BE relaxed and congenial and we will enjoy being with these young men. Nancy, get the door, please."

Nancy was frozen in place. Carole knew that Nancy would be the weak point, so she took her friend's arm and led her to the door. Carole actually had to open it, holding on to Nancy's arm to keep her from bolting.

When the door opened, Julie and Claire gasped as the four boys stepped in. The youngest looking of the four stepped forward and spoke with impressive composure and eloquence.

"Good morning, Ladies. My name is Randy. My friends here are Trip, Alex, and Jeremy. I understand that this is a shock to most of you. We're going to bring in the food, now, and give you a little longer to recover before we find out who you are.

"I'm sure that Carole told you that we are used to being around naked women. That will all be explained later. We are all hormonally challenged teens, though. If you notice the inevitable effects of your lovely naked bodies on us, please don't be offended. We certainly intend no disrespect. We just can't help it."

The four boys walked back out the door, while three of the women stood stunned, and even Phyllis was subdued. "Well, are you going to let these kids be the only ones with some composure?" Carole demanded.

"So, you set this up without telling us?" Julie challenged Carole.

"Yup. Actually, you can thank Nancy for this special treat."

"Wh ... what? I had no idea! What do you mean?" Nancy protested.

"Well, you told Rebecca about last week's naked brunch. She has connections at Transformations, and voila!"

"Ohhhh, no. I'm sorry!" Nancy moaned.

"Sorry, nothing!" Phyllis laughed. "From the size of those hubcaps you wear on the end of your boobs, I'd say you're as excited as any of us." That brought a lot of good-natured ribbing down on the wildly blushing Nancy and did a lot to ease the tension.

Carole challenged "They'll be back in a moment. Are you going to help them with the food, or not? And don't even think about covering up!"

It was the right move, giving them something to do. The women, even Nancy, met the boys at the door and took their loads from them to the kitchen while the boys went back for more.

Once a whole array of containers was spread around the kitchen, the women naturally started to help with setup and serving. That caused Randy to make another speech. "Ladies, please! To us, catering for you means that you do nothing but eat and enjoy. Believe me, we are all very used to serving meals. You may watch all you went, but let us do our jobs." He said it in a light-hearted way that did not offend.

Gretchen Berg, the Tee's food service manager, and Carol, her assistant, loved preparing special meals, and they had gone all out for this one. By the time the women were enjoying dessert, they seemed to have forgotten their exposure.

Nancy was mercifully distracted from her embarrassment as dish after dish showed not only excellent quality and preparation, but obvious attention to sound nutrition. She made a mental note to meet and congratulate whomever had prepared the meal.

All of the women were pleasantly distracted by the noticeable bulges in the boys' pants.

Carole got everyone's attention when it appeared to be time to leave the table. "The reason the guys have not answered many of your questions is because they were instructed not to. They are more than willing, but I needed to get your agreement, first. Rebecca has convinced the management at Transformations that anything we learn about their operation will not leave this group. Believe me, that took some fancy talking. Is there anyone who cannot swear to that?" That was a pretty serious promise, but the Gang had a long history of total discretion with each other's sometimes sensitive secrets. They all agreed.

"OK. While the guys clean up, you know where the bathrooms are. Fix your hair, powder your face, rouge your nipples, fluff up your pubes, whatever will make you more comfortable." Carole paused and ducked a couple of thrown napkins.

Carole could not resist ramping up the talk. "If you need to get off to relieve the tension, you'll find some scented pussy wipes under the counters." She waited for the protests to die down. "I want you to hear these guys' stories. I'll buy dinner at Chez Charles for anyone who can make it through all of them without crying. OK, go do repairs. You've got about fifteen minutes."

Sitting naked at the table while the boys served was one thing. When they adjourned to the family room where they all sat facing each other, it took some getting used to for the women.

Randy, the boys' eloquent spokesman spoke right away. "I'm sure you all noticed how your naked bodies affected us. We all wore heavy jock straps this morning, but..." he let his voice trail off suggestively.

"I think all of the guys will agree with me that we were stunned when we walked in and saw all of you. Having been told your age group and having seen a number of the women residents at Transformations, we thought we had come to the wrong house, or something.

"As you probably know, the Tee, as we call Transformations, stresses getting the body in the best condition it can be in as part of the transformation process. Well, I think the five of you should come to the Tee and be living examples. You would be an inspiration to our residents, I'm sure." As if the women had not already been eating up the boys' attention.

Of course, no one got the free dinner. In fact, almost all of them teared up at all of the stories. When Randy told about his persistent erection problem, Nancy blurted out "How can you just sit there and talk about something so ... so private? With strangers!"

"I don't consider any of you strangers," was Randy's first response. "All over the Tee complex, we learn that everything about our bodies is just normal and natural. It's nothing to be secretive about. Besides that, who knows when hearing my story will end up with someone else being helped. I feel like I owe my current wonderful life to people who were willing to help me."

That was the tone of the next few hours. After the guys had left with unashamed hugs from all the women, the other four accosted Carole. "I don't know whether to hug you or scratch your eyes out," Claire stated.

"Oh, who do you think you're kidding?" Carole riposted. "Your nipples never got soft the whole evening, and I think I can smell you from here. You'll take any chance you can get to have appreciative male eyes ogle your bare ass." The others laughed at Claire's mock pout. As the group's usual instigator of things ribald or suggestive, they enjoyed seeing her topped for once.

"Well, is this just a way to get us to donate?" Claire tried to recover.

"That's up to each of you. I'm finding lots of things there I'd like to help with," Carole answered.

"So, why naked these last two weeks?"

" ... and next week at Nancy's, for sure," Carole interjected to only mild comments from the others. "Some other boys will be serving."

Then she went on to address Claire's question. "Look, maybe I'm the only one, but I think my life needs some spice," Carole tried to explain. "Don't get me wrong. I love doing the investment stuff. It's in my blood. But I need more to feel like I have really retired."

"More sex, you mean?" Claire jibed, trying to get the upper hand again.

"Absolutely. Look, we've all worked hard to keep our bodies looking much younger than we are. I think it has extended all of our sexual peaks way beyond any normal curves. We each have some sources of sex, but I'm not satisfied with mine for a number of reasons. From the general grumbling, I doubt the rest of you are satisfied, either.

"So, the nudity thing was triggered by my interest in Transformations and Rebecca's connections there. These two brunches were just a start, though. I have tentative reservations for a villa at a nude resort in the Caribbean for ten days from now. If any of you don't want to do that, I have to know within three days. The deal is all of us or none of us."

"How many days did you reserve for?" Phyllis asked.

"Four nights," Carole answered. "In case we find it boring after the initial shock, I didn't want to string it out too long."

Nancy's concern was noticeable, but Carole had validated something about her friend that evening. Nancy was probably not faking reluctance, but somewhere inside, she was as much an exhibitionist and sexual adventuress as any of them. The answer was to ignore her protests. She would not actually turn down anything exciting.

All of the Gang of Five, even the supposedly reluctant Nancy, loved spontaneity, even if it was as personally embarrassing as the current trip. Part of the appeal to most of them was the way it shocked the children of those who had them. Phyllis had never married and Claire was divorced with no children, but Carole, Nancy, and Julie enjoyed the impact of their adventures on their offspring.

By agreement, they had just said that they were going to a Caribbean resort on a special deal. They did mention the name of the resort, wondering if any of the offspring would investigate enough to discover that it was clothing optional.

By agreement that was reached only after some argument, clothing was not optional for any of the group. They would wear only what was absolutely required by the resort management in a particular situation.

They did rent a large villa because they wanted to be able to just walk out the door and be on the beach. Also, even though the food and service at the restaurant was excellent, Nancy insisted that they stay with their eating discipline for at least two meals each day. For the one meal a day that they ate at the restaurant, they ate by the pool two of the evenings. By the pool, they could stay naked.

Nancy had a very successful career as a nutritionist and dietician, both in her own practice and on contract with several hospitals and clinics. Like the others, she was semi-retired, but she took the responsibility of making sure they all ate properly very seriously. It was the great tragedy of her life that she could never get her own beloved husband to follow an eating plan that could have staved off the hereditary heart problems that took him at fifty-five.

When they were driven to their villa and had stowed their modest luggage, Carole told them "OK, we're going to get this over with. We are going out there naked and we are going to walk all over the whole complex. Even with all of our tanning booth time, we're still what I think the nudists call 'cotton-tails' - we're paler than most people here."

"But, Carole," Nancy objected. "There are lots of people here who have clothes on."

"That won't be us," Carole said firmly. "It's late enough in the day so we don't need sunscreen. Pee, get your sandals on, and let's go."

Claire and Phyllis had to take Nancy's hands as they left the villa. She was actually a bit unsteady. As Carole had suspected, though, it did not take Nancy long before she was strolling, gawking, and greeting passersby with the rest of them.

They did not stay together all of the time at the resort. With the many water activities available, their interests led them to try different things. The one time they were always together made quite a sight. Early each morning, they ran together on the beach, making several circuits back and forth to reach three miles. All but Claire wore sports bras to prevent their breasts from bouncing too much, and Nancy and Julie wore shoes because of stress problems with their feet. None of them wore anything else.

There was plenty of time in the sun for discussion, and nudity ended up being a big topic. There were jocular debates about whether circumcised or uncut penises were more attractive. The clientele were, in fact, mostly Northern European, and many of both sexes had all pubic hair shaved off. That was also a topic of light-hearted debate.

The clientele was skewed toward the older generation, and there were many sober comments about the generally poor physical condition of both older men and older women. "How can a woman expose THAT?" Claire demanded at one point. "Has she no pride? Is that what European beaches look like?"

"I don't suppose American beaches would be any better if they were nude," Phyllis answered. "Why do some of those out of shape men bother to shave their crotches, anyway. No one can see anything under those hanging bellies."

There was definitely an ego boost for all of the women. All eyes were on them wherever they went, and they knew it. When Nancy came out of the bathroom the third morning with tightly trimmed pubic hair, it set off a storm of good-natured teasing. Her retort was "Do you realize that four of us have half of the total pubic hair on this whole beach?" More than anything else, that episode reassured Carole that she had done exactly the right thing.

"Do you really think this will affect us that much when we return home?" Julie asked on the fourth day.

"Nancy, how about you?" asked Phyllis. "Are you feeling any different? When the men stare at you, does it bother you less than when we arrived?"

"Oh. I hadn't thought about that," Nancy said thoughtfully. "Actually, I don't even notice the men much, any more. Well, if they have especially nice muscles or a neat cock, I do." That was quite a statement for Nancy to make, and Claire broke into a belly laugh.

"You're a genius at more than money, Carole," Claire chortled. "It's working."

"But when we get home," Julie complained, "there won't be any chances to go naked for anyone."

"You never know," Phyllis retorted. "Maybe we can just make chances."

"Easy for you to say," Nancy objected. "You didn't even blush the first time we walked out of the villa."

"Well, I guess when you're in a body profession, you get pretty used to it all, kind of like doctors." Phyllis had a long, successful career as a trainer, including a stint with a major league baseball team. She had invested her savings in health club ownership early on, and now had a majority position in three profitable clubs. That was in addition to her very healthy stock portfolio that Carole managed.

Carole had brought up the whole idea of the nude resort because in her early months of retirement, her single status had affected her like never before and she was looking for ways to spice things up. She did not really want to marry, much to the dismay of two fairly regular dates who kept trying to change her mind. The two were not just gold-diggers, either. Marriage just did not seem that attractive to her. Her life was great, except for the occasional bout of loneliness.

Carole Gruden had worked in the research department of a brokerage firm for thirty-three years. A double major in economics and accounting and an MBA with a finance concentration had made her a prize recruit out of college. She had just reached fifty-eight when she had 'accepted' an early retirement buyout offer from the firm.

Her first reaction to the offer had been anger. There was no question that those in the firm who actually knew anything about investing regarded her as the resident genius. At least three of the corporation's top officers had gotten their careers off to great starts by applying Carole's advice to accounts of key, influential clients when they were brokers.

The problem was that Carole had always focused strictly on generating profits from the equities themselves. The firm generated profits the same way, of course, from equities held in its own portfolio. However, the brokers earned their livings on transaction fees, not on the growth of their clients' equities.

From the beginning, Carole had always felt that the broker system was irreparably flawed and did not serve the clients well. She knew that she was extreme in her views and she tried not to be disruptive by espousing her opinions loudly.

On several occasions, she had been offered broker positions. She always suspected that the offers were more to shut her up than anything else. Every time such an offer was made, she reluctantly muted any criticisms or objections she had been making.

One offer that had been harder to turn down had come from outside. A former officer of the firm, one who knew of Carole's personal investing success, tried to get her to join him as a fund manager. There was no existing fund manager with portfolio growth like Carole's own.

Management knew that Carole's theories and recommendations were right on - more accurate than any other researcher in the corporation. The brokerage held her portfolio, so her asset growth that nearly doubled the highest-rated mutual funds was there as an inspiration or an indictment to everyone.

Well, management thought they knew what Carole's portfolio was like. In reality, only Julie Cashien, one of the close-knit 'Gang of Five' long-time friends and Carole's CPA and tax attorney, knew the real story. Ever since online investment services had become available, Carole had committed a percentage of her portfolio to high-risk stocks with high growth potential. These, she managed online, rather than through her firm.

Even just her astute investments in the '' boom would have been enough to set most people up for life, but she had also 'guessed' correctly on a number of foreign oil and gas projects that had achieved insane multiples.

Normally not a rigid or inflexible person, Carole just could not go along and say 'That's not a sound strategy for the client, but go ahead, I know you need the commissions.' It even cost her her marriage. In her late twenties, she had fallen in love with a rising young stockbroker at the firm. Their marriage of seventeen years had produced her three children.

Her husband had eventually been seduced into more and more of the 'churning' and other activities that produced broker revenue but did not always benefit the investors. Being in research, an insider, Carole knew where the values were and she knew what strategies would produce the best asset growth.

Her husband really was not doing anything that other brokers did not do routinely, but her ethics were offended. When her increasing urging toward different strategies and her criticism of what she considered a failure of his duty to his clients increased, their marriage began to unravel. Eventually, they divorced quite amicably and he moved to a distant branch of the same firm.

So, her expertise had found her a husband and allowed her to have a family, but her integrity had eventually cost her the marriage.

In the end, with the help of Julie, Carole had worked out a separation contract with the brokerage. In exchange for leaving with only her 401K, she had been guaranteed lifetime access to the research sources that she had used when employed.

Of course, she could not use those sources to compete in any way, but the contract defined competition as providing investments advice for profit. Carole had never done that. All of the benefit of her expertise that she had given her friends and family was strictly by informing them of every transaction that she had done for her personal portfolio. That satisfied the letter of her employment contract. She partially assuaged her guilt at breaking the spirit of her employment by insisting that anyone she informed of her own trades must use her brokerage firm.

Her four friends and several family members had been shadowing her long-term trades for twenty-five or more years, as had several other relatives. Although most relatives had been too cautious, her four friends had also duplicated her higher-risk aggressive online trades.

That she was wealthy by most any measure would never be apparent to the casual observer. She lived in the same upper-middle-class home that she had shared with her husband. Everything in the house was in perfect condition and of the finest quality, but it was still of modest size and in a neighborhood of Honda, Toyota, and Suburban more than BMW, Lexus, and Porsche.

Unlike many other people who rise from humble family circumstances, she had no desire to have her true worth known. She had, in fact, used her money and her skill to make sure that her family wanted for nothing.

On her first day of official retirement, Carole had sat down with Julie to plan a way that she could set up and manage the equivalent of several mutual funds for the people in her circle. It had taken two months of legal investigation to make sure that she was not violating her contract or any laws. Now, she was her own not-for-profit brokerage firm, and she loved it.

If only she could get better resolution to her need for sex...

After laying in the sun and discussing the benefits of nudity for some time, Carole blurted out "This dating shit just isn't working for me!"

"You're just now figuring that out?" retorted Claire. "I haven't had my bell properly rung for so long I can't remember."

"I guess when I was still working, it was different," Carole admitted. "There were more chances to meet men and I had less time on my hands."

"What we need is a stable of studs that we can rely on." That comment came from Nancy, one of two widows in the group, and it was a real surprise. Nancy always managed to come across as the most sexually conservative, although the others all knew that she was a sexual dynamo at heart.

"Are you talking about sort of a male harem that we could share?" Julie asked.

"No," Nancy replied. "Men who would tolerate that, we wouldn't be interested in. Don't you think there are men out there who don't want to get married, but would like dependable partners that won't put demands on them?"

"Well, you know what they say about older single men," Claire warned. "A lot of them are looking for a nurse and a purse." That lightened the mood.

"If they're that far gone," Phyllis said with a snort, "they wouldn't do my itch any good. I see guys our age in wonderful shape at the health clubs all the time."

"And what's wrong with finding some young cocks, too?" Claire suggested.

"Nancy, were you suggesting that we should hire these men?" Carole asked.

"Oh, no! Nothing like that," Nancy answered. "I was thinking of strong, independent men, just like us. I just thought that if we and the men agreed to find companionship among the group, it would benefit all of us. Um, think of men that we would consider marrying."

"If such a prize existed, why wouldn't one of us want to marry him?" Julie demanded.

"That's a worn out conversation," Carole countered. "I honestly don't think any of us can imagine a man that good. I agree, though, that what you are describing sounds too good to be true."

"I might actually know one possibility," Phyllis mused aloud.

"Well, come on! Tell!" Claire demanded.

"He's a successful entrepreneur, about sixty. He lost his wife of thirty-five or more years about eighteen months ago. I understand that he spends a lot of late nights working out like a madman at the club."

"Is he in good shape? Is he well hung?" Claire asked eagerly.

"Now, how would I know how he is hung?" Phyllis laughed.

"Isn't there a peep hole for staff, or something? Can't you get one of the male staff to find out for you?" The others couldn't help but laugh at Claire. She was always making ribald comments and jokes, but she was honestly a very sexual person.

"Let me see what I can find out," Phyllis promised.

"We want a full report as soon as we get home," Claire continued. "Pictures would be good." By that time, the rest were laughing uncontrollably.

"Well, this place has done nothing to scratch any immediate itches," Phyllis proclaimed. "Lots of eye candy, but no one to take to bed."

"It's a good thing I have pull with the club management," Phyllis declared. "I was able to..."

" ... and a majority share of the ownership, too," Julie added with a laugh. Sticking out her tongue at Julie briefly, Phyllis gave a purposely drawn out description of how she had plotted to try and get a look at the 'target' in the shower. As she dragged out each detail to the max, she looked innocently at the fuming Claire.

"Phyllis, if you don't quit pissing around and get to the good stuff, you won't be able to enjoy him if we do 'recruit' him," Claire threatened, her perfectly tended nails extended clawlike toward her friend.

"Well, Claire, there just wasn't any way. BUT, you and I are going to check him out in person - in the shower, Friday night."

"In person? You mean showering with him?" Claire asked, her mouth agape and her astonishment clear.

"Whatsamatter, Claire? You all talk?" Carole teased.

"No ... I ... Let me get this straight, Phyllis. You want me to go with you into the men's shower room..."

"Ready for a shower, as in naked," Phyllis added.

" ... just to get a look at this guy?"

"I thought it should be more than just a look," Phyllis said thoughtfully, obviously pulling Claire's chain.

"But what about other men showering?"

"You're not shy, are you? You sure don't talk like it, and the way you pranced around at the beach..." Phyllis prodded. "Who knows? Maybe some other studs will get so hot over seeing us strutting our stuff that they will beg to join the 'stable'." At the last word, Phyllis nodded toward Nancy, who had used the word when first floating the idea a week earlier at the resort. Phyllis knew that they would be the only ones in the club, but she was not about to let Claire know that, yet.

When Claire was left speechless for a record time, Phyllis said "Well, Nancy, would you like to accompany me, since Claire is too timid."

"NO!" Claire literally shouted. "I'll go. Should I shave my pussy, like yours?" Chutzpah she did not lack. There was no way that she would ever mention the concern about other men again.

Now that her teasing of Claire had run its course, Phyllis had to reveal her true plan. "Roger Trent is his name. He regularly closes down the club on Friday nights. From what I have been able to find out, he fears the inactivity of the weekend. Apparently, he never sleeps much at all."

"Poor man is really taking it hard, isn't he," Nancy said sympathetically. "I know how he feels." It had taken all of the love and support her friends could give her to bring her through the loss of her husband.

"The fact that he had a marriage like that makes him a good candidate for us," Claire said in a surprisingly serious mood.

"My thoughts exactly," Phyllis agreed. "Now, since I found Roger and have done some of the snooping and planning, do I get to call the shots here?" With only a little nervousness, the others agreed.

"Uh, Phyllis," Carole spoke up, "I think some professional guidance might be good. I got Rebecca to take us on as consulting clients. Let's arrange a time to talk to her."

"Good idea," Nancy offered. "This whole thing makes me nervous."

"And horny, too," Claire teased. "Admit it."

"Can you give me a minute to recover from this shock?" Rebecca said to the Gang. They had just told her how they planned to recruit Roger Trent as the first member of their 'stable of studs'. "Aunt Nancy, for the first time, I'm concerned about the crowd you're hanging out with," Rebecca joked.

"I could not imagine doing what you are planning at the club, so it would be unwise of me to comment on that plan," Rebecca said in her professional manner. Quickly changing her demeanor, she said conspiratorially "I'll discount my fee for a detailed account, though. Any chance of video?" That broke up the whole groups because she sounded so much like Claire.

"I cannot believe that I am going to suggest this," Rebecca went on after the laughter subsided. "For the first sexual session or two with Roger, I believe it should be two or three women."

"Why do you say that?" Carole asked. The whole Gang was quite sober.

"In my experience, widows and widowers who had good marriages suffer from fears of being unfaithful to their dead spouse if they have sex with anyone else. It is my guess that Roger has serious problems with that. A threesome would soften the feeling of being with another woman by making it a little less personal - not quite so much like choosing another mate."

"Wow! We've, uh, never done things like that together," Julie commented. "Do you really think it will make a difference?"

"Look, I have not met the man, and none of you know him well," Rebecca explained. "I am just going on research and experience. Just from the way he uses the club so religiously, it must be an escape for him. That tells me that you have a tough job convincing him to have sex at all. I just think you have a better chance of getting through to him with multiple women.

"One more thing. Aunt Nancy, you and Julie are widows. You have a unique way of connecting with Roger." Again, Rebecca went from professional to personal demeanor.

"God, Nancy! I can't believe I'm counseling my almost-mother on how best to seduce a new man!"

The laughter at that was subdued because they were all still concerned about the group sex idea.

"One other factor you should consider: what was his wife's physical appearance? Which of you most resembles her? Frankly, I am not sure how to use any similarity. I suspect that a woman of similar body type might have an easier time breaking through his resistance. I admit there is a chance for the opposite reaction."

They talked with Rebecca for a while longer before she had to leave. Carole almost ordered them to sleep on it and meet the next afternoon. Phyllis promised to find out what Roger's wife had looked like.

When the gang assembled at Carole's the next day, they were all sober. Claire, surprisingly, brought up what was bothering all of them.

"I love all of you. You know that. But, to have sex with a man together - that's ... that's ... we've never done anything like that."

"OK, everyone. Strip!" Carole ordered, setting the example. The others seemed puzzled, but complied. When they were all naked, she commanded "Now, find a comfortable spot where we can all see each other, and we're going to jill off together."

"WHAAAAT?!" came simultaneously from the other four. The babble of objections went on for a while. When it subsided, Phyllis took up the argument for Carole.

"She's right, gang. We're talking about a whole new sexual environment for ourselves, here. We have good professional advice that Roger's first couple of times should not be with just one woman. In the future, though, it will be a great, uh, weapon, to be able to give a man a threesome. I'll bet we can learn to like it, too.

"The thing is, Nancy and Julie, you two should be with Roger first because of the loss of spouse connection. You cannot let on in any way that you are embarrassed or ashamed. It has to seem natural and easy. Oh, Nancy, Emily, Roger's wife, was built like you."

"God! Phyllis is right, gang," Claire chimed in. "Uh, Phyllis, you don't think we need to, uh, do anything with each other, do you. That's just..."

Carole picked up again. "No, Claire. I don't think we should change the way we feel about that."

"I think I know how we should approach it," Julie chimed in. "Let Nancy be the first, and I'll act sort of like, I don't know, the organizer, or something."

"Why me first?"

"His wife was built like you," Phyllis explained.

"Remember, Rebecca said he could react badly to the similarity," Nancy warned.

"Yes, she did," Carole responded. "She thought that was the least probable outcome, though. We have to go with that plan."

Carole ended a rather lengthy discussion by beginning to diddle herself. One by one, the others undressed and joined in. Because of the newness and the embarrassment, it took almost twenty minutes before all of them came.

Carole broke the resulting silence with "Is everyone OK?"

Claire had been knocked completely out of her usually ribald persona. "I guess we didn't think this all the way through, did we? I'm still all for it, though."

The five got together as often as they could before the big Friday night. No one argued about the group masturbation sessions that Carole 'ordered' each time.

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Story tagged with:
Ma/Fa / Consensual / Romantic /