Gang of Five - Cover

Gang of Five

Copyright© 2009 by Shrink42

Chapter 2

Romantic Sex Story: Chapter 2 - 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  

Roger Trent was once again closing down the health club on a Friday night, and as usual, it was for the wrong reason. It was great that he had the discipline to keep working out regularly, and he should have been proud to see how good his sixty-year-old body looked. The problem was, he came to the club late at night because he could not sleep. Pills or alcohol had never been acceptable insomnia remedies to him. Sex was the perfect remedy, but therein lay the heart of his problem. He had become a widower eighteen months earlier.

I was a story too often told. Roger had built a very successful HVAC business from the ground up. He and his beloved wife had struggled mightily through some very lean times, but the last fifteen years had been very comfortable.

Just as he had been seeking buyers so they could start seeing the world, his wife had been diagnosed with a virulent cancer. She was gone in just eight horrible months, leaving a gaping pit of constant pain in his heart. Theirs had been one of those loves of a lifetime, and he could see no way to fill the emptiness.

That Friday night, Roger had not seen any of the usual late-shift folks at the club. They all knew him well, and often let him stay well past closing as the nightly cleanup took place. When he had checked in, the part-time trainer named Phyllis was at the desk, and he saw no one else around.

He knew Phyllis causally. In fact, it had been Phyllis who had recommended his regimen when he first came to the club shortly after his wife's death. She was semi-retired and usually worked only days. As with so many things in his life, he noted that her being there alone was unusual, but put no more thought into it.

That night was a strength night. Alternate nights were strength and aerobic concentrations. Hoping that it would hasten sleep when he got home, he had pushed himself to just short of the strained muscle point. Just getting out of his workout clothes had been a struggle and he looked forward to a quick shower and a soak in the locker room's whirlpool.

He was facing the shower room wall, wetting down his hair when he sensed someone behind him. He was a little surprised because he thought he was the only customer. Besides, why wouldn't another guy have the courtesy to use a different part of the roomy shower area. He had not heard of any gay approaches at the club, and the thought of that possibility alarmed him enough that he turned around to see who was there.

It certainly was not a gay approach. Facing him were five naked women of around his age. One was Phyllis. She smiled warmly at him, undaunted by his look of mixed alarm and irritation. "Don't worry, Roger. You didn't get in the wrong locker room by accident. We are the only people in the club, and it is all locked up," she told him. "Let me introduce my very good friends."

"Why?..." was all he could get out at first.

Phyllis had thought out the next move carefully, and it had been discussed with the group. The problem was how to get his attention and spur some interest without offending him or scaring him off.

"Roger, we want to spend some private time with you and get to know you. First, though, there is one important question that we need to have answered."

With that, she stepped right up to him and began stroking his penis. Claire approached him from the side with one hand fondling his testicles and the other kneading an ass cheek. The other three women moved close and they all touched him with at least a hand.

Phyllis was looking him straight in the eye. When he grabbed her wrists as if to push her off, she said "Don't, Roger. Please. We just need to find out." That puzzled him just enough so he paused with his hands still on her wrists.

With almost the reaction speed of a teenager, his penis expanded in her hands. Just as the feelings started to overtake him, both women let go of his genitals. Leaving him with his cock rigid, all five women set about washing him thoroughly. When they were done, Phyllis led him to the whirlpool room.

Instead of getting into the tub, Phyllis laid a mat on the floor, put some towels over it, and got him to lie face down on it. He was far too overwhelmed and disoriented to resist. All of the women then began working his muscles.

None of the women said anything and he was content to enjoy the feelings while he tried to make some sense of the situation. When they helped him sit up and get into the whirlpool tub, his cock had lost none of it stiffness.

Once they were all seated, Phyllis told him "I have heard that a tragic loss of a wife can leave a man impotent. At least that is not one of your problems. Do you masturbate a lot, or is there just no desire there?"

"Phyllis, that's none..."

"Please. There's a good reason I am asking," she cut him off. "I hope you are not offended, but we've done some checking up on you. We're guessing that you were completely faithful to your wife, right? In fact, knowing our generation, there's a good chance that you were each other's only sexual partners."

That comment made him jerk in surprise. He nodded with a very sad look. "We've talked with a psychologist. She said that some widowers do not want another wife because they see it as being unfaithful to her memory. I suspect you may be struggling with that.

"We are a group of long-term, very close friends. Nancy and Julie are widowed, Carole and Claire are divorced, and I have never married. We are all healthy, independent, and financially secure. Also, we all love sex, but we are very selective of our partners. None of us is seeking a husband. We have decided to try something unusual. We want to find men who have similar relationship interests to ours and are interested in some 'no-strings' sex and social partners. Actually, we want men of such caliber that we can all be close friends with them. Some pairings could even result in marriage, but that's not important for right now."

"And ... and you want me to... ? But if you know how I feel about being unfaithful..."

"Think about it this way, Roger," Claire spoke for the first time. "You're not impotent by a long shot. I'm guessing that both you and your wife took pride in your sexual prowess, right?" He blushed and nodded.

"I don't know your opinion on the afterlife, but suppose that your wife is watching you right now. Would she be jealous and upset if you used your sex to enrich the lives of some nice women - and your life, as well? Or would she be happy that her unfortunate departure from your life had not totally eliminated that important aspect? Would she be saying 'It's about time, Stud?"

"That's ... that's ... I have never even thought in those terms ... I..."

"It's the kind of man you are, Roger," Phyllis commented. "It's the kind of character you have. All of our 'Gang of Five' have that kind of character. We would love to have a man like you to share our lives, including sex."

"I've never met anyone like you. You're so open about it, and..."

"Does it offend you? Do you think we are loose women? Sluts?" Claire asked, keeping her tone gentle.

"You don't seem like that, but..." Phyllis wondered how long it would be before he completed a thought. That was not fair to him, though. This had to be the most unusual experience of his life, by far.

"I'm sure you're tired of people telling you 'life goes on'," she said. "I suspect that you agree. You just have not found a way to take the first step toward going on."

"You want me to have sex with all of you?"

"Our psychologist thought it would be best to start with multiple partners," Phyllis answered. "If your first return to sex is with two women, it will be a little less personal and your feelings of unfaithfulness will be less."

For the first time, Roger tried to exert some control. "Why are you trying to get me to do this? You know how I feel. Why not just leave me to heal by myself?"

Phyllis answered first. "You are an achiever, Roger. You built something significant in your life. It is still a fine business, but it's like you are just riding it, now. The world needs every man like you it can get. You can't just bury yourself with your wife." That last phrase had been scripted after careful discussion. It was risky, but the women trusted the kind of man he was. He was obviously affected by the words and he was very thoughtful for a while.

"Roger, Phyllis gave you the hi-falutin psychological reason," Claire interjected, "But you're a stud. Your great body looks at least ten years younger. This cock is a real beauty, and your balls - WOW! - they're big enough to fill all of us in one night. We're five horny old bitches who like real men and are willing to share. Does that really sound so terrible?

"Now, if you're only interested in tight young boobs and butts, just tell us and we'll leave you to find some young stuff. But if you value life experience like your own, we're anxious to share it with you." That was quite a speech for Claire, normally a non-stop joker, and the racier the joke, the better.

"Roger, here, sit up on the edge of the tub," Phyllis asked him gently. Apparently, he honestly did not know why she had asked that, so he complied. He was not even settled before Claire had engulfed his cock in her mouth. For her part, Phyllis got behind him on her knees with his head between her substantial breasts. She began running her fingers through his chest hairs, and when he showed signs of getting close, she began to tease his nipples.

"Uh, uh, look out!" he warned, and within seconds, he was pulsing into Claire's mouth. She swallowed all but a dribble at each corner of her mouth, then licked his shaft all over to clean it.

As he sat gasping, Phyllis took another chance and did something definitely not in the script. Right in his ear, she spoke very quietly. "Honey, bow your head and talk to your wife. Tell her you have a chance to make five women as happy as she was. Thank her for the wonderful man she helped you become. Promise her that we will always respect her memory and honor the life you two shared so wonderfully. Will you do that, Roger?"

It must have been just the right thing to say because he started to cry. At first, it was just sniffles and a trickle of tears, but it soon became full-body sobs that went on for minutes. Without even wiping her mouth, Claire got on his lap and smashed his face to her breasts. Sensing his need for comfort, Phyllis spread her legs around him and hugged him from the rear, pressing her breasts into his back. The other three women pressed around him any way they could.

Contrary to her normal persona, Claire was the soul of sensitivity. When Roger started to recover and seemed ready to speak, she took his face in her hands and said "Don't you dare try to apologize. Julie and Nancy lost their husbands, and we tried to help them through that. You wouldn't be the man we want in our lives if you didn't feel her loss this deeply. Have you ever cried before?" He just shook his head. "Then, it's about time. We feel privileged that you let us share it. Now, you're really ready to start living again, aren't you?" He could only look at her wide-eyed.

"Tell you what, Roger," Phyllis said after some more cuddling. "Go with Nancy and Julie to Nancy's house. They've lost their spouses, and the three of you have much to share."

"I'm ... I'm not very, uh, decisive right now, am I?" he admitted. "That was unbelievable. I don't have anything with me."

"For what my horny friends want to do with you, you only need this," Claire quipped as she fondled his limp penis. More seriously, she told him "You've got what you take to the gym. You won't need any more."


Once it was clear that Roger would go along with their plan, Phyllis, Carole, and Claire left the club. Nancy and Julie helped him get dressed and donned the warmup suits that were all they had worn to the club.

As befits a man in the building trades, Roger drove a pickup, but a very upscale pickup. Nancy took the front, sitting by the door, while Julie got right behind him.

When they were on a short stretch of expressway, Julie got her mouth right by his outside ear. Kissing him to hide her real intent, she whispered. "Sweet Nancy always worries that she is too heavy to be sexy. We know that your wife was built a lot like Nancy. Please, try to reassure her."

He barely restrained the urge to look over at Nancy. Even with everything else that had happened, Julie's little request had a tremendous impact on him. It gave him a glimpse of the kind of love the women had for each other. It was the kind of love he had shared with his wife, and he wanted to share that again.

So far, he had been at the mercy of these women. That was not his sexual persona, at all. Far from being submissive, his wife had nevertheless reveled in his strong, take-charge approach to love-making. In his chariot, with one woman making a request on behalf of the other, he started to feel some of his former attitudes returning.

The comments about what his wife would think had really struck home. Why had no one said such things to him before? Actually, he knew it was because he had never allowed anyone close enough to say them. The shock of the shower room encounter was fading, and he was remembering the five naked bodies. It hurt him to admit that they all looked more fit than had his beloved wife. While by no means young, they all looked sexy to him. That was why he had not resisted the blow job - he needed the release.

The woman sitting next to him did have the same hour-glass build as his wife. From what little he had been able to focus on one body in the shower room, her large breasts, huge extended nipples, and lush hips and ass had brought back memories. His dear wife's waist had never been so narrow, nor her belly so flat, nor her thighs so taut, though. How could Nancy be worried about being too heavy? He would certainly disabuse her of that worry, and he would only have to tell the truth.

The woman in the back seat - Julie: she had a perfectly proportioned figure. Of course, there was some sag. There were some wrinkles, some age blotches, but like all of the women, she must have taken wonderful care of her body. To him, that was sexy, another reason to respect and, yes, to desire the women.

In that fifteen minute drive, Roger allowed changes that he had fought back for many months. He was strong emotionally, but he had let his loss sap that strength. He was not co-dependent, but he had acted lost without his spouse. He was independent and self-motivated, but he had just been going through the motions.

The five naked women in the shower had stimulated him, but they had also shamed him. It had not been intentional, but when they shared their rather lofty image of him, he was chagrined that he was no longer acting like the man they saw.

The most damning revelation was that his wife would no longer be proud of the man he had let himself become. She would want him to be the stud that these women were looking for. They had been absolutely right about that. In fact, she had said similar things a number of times in her extended goodbyes. He had just refused to remember those words before.

When they reached Nancy's house, Roger went into complete gentleman mode, helping both women down from the high truck. Inside, he took just a moment to look around and compliment Nancy on her beautiful home. Then, he eagerly and honestly concentrated on Nancy herself.

They had naturally moved to the kitchen, without any specific plan for food or drinks. He came behind Nancy, grasped her upper arms gently, and began to nuzzle her neck and ears. As she reacted to that, he reached around and unzipped the warmup top that was one of her only two garments.

As the top hung loose, he moved around in front of her and slid it off of her shoulders. She was too nonplussed to react, and he put the top into Julie's extended hand. Putting a hand under each of Nancy's breasts, he gently hefted them for just a moment, then ran his thumbs over the already swollen nipples.

As he dropped to his knees in front of Nancy, he could see the grin on Julie, who was standing behind her friend. He gave Julie a surreptitious wink, then licked and kissed around Nancy's navel as he worked the suit bottoms down over her hips. When the bottoms were puddled around Nancy's feet, Julie took Nancy's hand for support so he could remove her flip-flops and the bottoms.

When Nancy stood naked, Roger again nuzzled her belly while running his hands lightly over her hips, ass, and thighs. Standing up slowly, he kept running his hands farther up her body, ending up hefting her breasts and teasing the nipples again.

Finally, cupping her face in both hands, he kissed her, and said "What a wonderful body you have, Nancy. I'm sure you know that my wife was built like you. Frankly, she never looked this good, though. Show me to the bedroom."

Nancy could barely stand, let alone walk. With Roger on one arm and Julie on the other, they all got undressed and in bed. Only then could Nancy speak. "Roger, just because I'm like your wife, you can't favor me over the other women. We all need and want you."

There it was again, the evidence of love and care that he had thought to have lost forever. Thinking he should say something, he told her "How could I choose one of you over the others? You all have wonderful bodies. Julie, you are just perfect - every part of you is just right." With that, he pulled Julie into his arms and kissed her hard.

As difficult as it was, Julie pulled away from him. "You have Nancy so worked up she is shaking. Take her. Right now." It took only a glance to see that Julie was right. Nancy was beyond ready. "We are all clean and pregnancy is not an issue."

Julie then helped Nancy spread out for him, something Nancy could not do herself in her trance-like state. When he eagerly positioned himself atop Nancy, Julie guided him home.

It was only later that Roger would learn how significant that first three-way session was to be for all of them.


New sex between people who have experienced a lot of it has a special quality. They need make no pretense of shyness or reluctance. They can just concentrate on the important parts: the sensations, the giving, the special communication, the satisfaction of pleasing another.

There was no instant orgasm for Nancy, and Claire's blowjob had guaranteed Roger some control. It was straight missionary, but that in no way detracted from the intensity.

She soon had her legs around his thighs and buttocks and was revealing the libido behind her often reserved demeanor. He put his head down beside hers and concentrated on his strokes. To her delight, he filled her perfectly, and he made little sideways and rotating motions that sought out unsuspected sensitive places.

Despite only one previous sex partner, he sensed when her arousal peaked. On the next downstroke, he pushed his pubic bone hard into hers and rotated just a bit. The extra stimulation of her clit sent her off into ecstasy. The experience of a new woman orgasming around him was both familiar and unique. As his mind tried to grasp the similarities and differences, his own pace toward ejaculation faltered.

Nancy was in no way disappointed. After finally catching enough breath to speak, she told him "You can still do Julie, now, can't you?" There it was again, that concern for each other. He found himself falling in love with the whole group of them.

His time for pondering was limited. Nancy gently but firmly pushed him out of herself and toward Julie, who was ready on her back right beside them. Entry into yet another new partner just raised his already high level of excitement. Any muscle soreness was ignored, and he was soon thrusting into Julie just as vigorously as he had done with Nancy.

Later, after he had indeed emptied into Julie, Nancy had just finished cleaning them both up with a rag and a towel. "Will it always be with two of you at once?" he asked. That seemed to acknowledge that scheduling was their prerogative.

"No," Julie answered. "Phyllis found you and she will be the first to have you to herself. Carole and Claire will be next, though.

Nancy cautioned him "Phyllis always worries that she does not seem feminine. We can assure you that she is all woman and as hot for a man as any of us."

"As strong as she is, you'd better be ready for the ride of your life," Julie added. "Some men are frightened of her, but I don't think you will have that problem."

"Foolish men," he said quickly. There it was again, that tremendous concern for each other.

It was well into the A.M., but he questioned both women until he had learned a lot about their lives. Just before they drifted off, Julie asked "What's your feeling about the little blue pill?"

"I generally avoid drugs or any artificial stimulation," he told them. "If some of you are needy and I can't get it up, though, I'll consider taking one."

"We have connections, so we have a small supply of them," Julie explained.

"Before you resort to that, though," Nancy said, "I know of some natural supplements that really do work."


It was no surprise to Roger that all five women were there for brunch. Phyllis hugged him and asked "Are you feeling more like the old Roger?"

"Actually, I feel better in ways that I would not have believed," he told her. The other women were listening as he revealed "I always thought that the feeling, the love between Emily and me was unique. I know that sounds silly and sappy, but that's what I thought, and I feared it could never be found again.

"I've seen several evidences that the love between all of you women is almost like the romantic love I had with Emily. I won't say the hole in my heart and my life has been filled, but I can see hope for filling the emptiness."

Claire and Nancy had both teared up when they heard those words. Being totally serious, Claire asked "Will a hearty brunch be enough for you to take care of two more horny women?"

Despite Phyllis's honest urgency, she went along with the plan for him to spend Saturday night at Carole's with Carole and Claire. The evening started with dinner and he used that to find out about their lives and experiences.

Claire had studied a strange combination of Dance and Business in college. She had a ten-year career as a professional dancer, working in both ballet and in modern dance troupes. Her career could have gone on longer, but she began to get involved in costuming and makeup, and soon, the demands for her talents in those areas provided more income than she had ever seen from performing.

Using some inheritance money, she had started a high-end spa that included a leading-edge fashion boutique. Within a few years, she was charging obscene fees as a fashion, grooming, and decorating consultant for society weddings, debutante balls, and galas.

Roger had been warned about Claire's mild potty mouth penchant and her tendency to be flip. What he discovered, though, was a woman with several exceptional talents who had used them very well. She still owned the spa and still did occasional consulting assignments.

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