Gang of Five - Cover

Gang of Five

Copyright© 2009 by Shrink42

Chapter 1

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.

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

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.

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