Gang of Five
Chapter 3

Copyright© 2009 by Shrink42

Romantic Sex Story: Chapter 3 - 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  

Alan Trent was running just a little late for his standing Monday dinner date with his brother Roger. A police lieutenant, Alan often had events keep him after his shift, so this was nothing new to Roger, and he would not be upset at the wait.

All day, Alan had been trying to think of some new way to get through to Roger. Since Roger was two years older, even at their age it was harder for Alan to assume the counsellor mode. Still, it hurt to see Roger still trapped by the grief of Emily's decline and death.

Another reason it was difficult to talk to Roger about getting on with life was that Roger would turn it around on Alan. Being in the best possible shape, Roger was justified in chiding Alan about the way he had let himself go. His job was stressful and he had never married. Bad eating and little time or discipline for exercise had Alan sliding into potentially dangerous condition. So far, the deterioration was mostly in the health indices, rather than appearance, although 'fleshy' was becoming an accurate description.

Men are supposedly clueless, not tuned to the subtle signals that announce changes in a person's attitude or outlook. Police officers, however, are the exception, since reading people is sometimes a matter of life or death. It only took Roger looking up to see him approaching for Alan to see that something had changed in his brother - really changed.

The brothers sincerely loved and respected each other, but as far as communication, 'macho' had always been the accepted standard. "You got laid. About time. Anyone I know?" was Alan's greeting as he sat down.

"And you look like shit. How many doughnuts today?" Roger shot back with a grin. Then, seriously, he said "If they ever start blood pressure readings to get into the station, you're unemployed."

Raising his hands in surrender, Alan said "Really, Rog, something good happened, didn't it?"

Roger did not really want to hide things from Alan, but according to their code, he could not give in too easily. "Didn't know you had become a shrink."

"Cop. We make shrinks seem like amateurs."

"Yeah. I took a big step this weekend," Roger admitted. "I finally let some stuff go."

"How many loads of stuff?" Alan taunted.

Roger didn't take the bait. "You may never understand it, but the thought of being unfaithful to Emily was tough to get past."

"You're right, I don't really understand it," Alan admitted. "But I do understand that it was huge to you. You did get past it, though, right?"

"It finally got through to me that I was not really honoring her by being celibate. It would upset her to think that her passing would force that on me."

"You met a really smart woman, then," Alan observed. "None of the rest of us were able to get that same idea through to you."

"Oh, don't feel bad," Roger advised. "It took some time, and the circumstances were ... exceptional."

"So, you're not going to tell me any more than that?" Alan grumped.

"You know the rules," Roger reminded. Their parents had taught them that respect for women started with being discrete about anything that could affect a woman's reputation. They had long ago agreed not to share any details. "I'm finally on the way back, though."

"That's great. We've all been pretty worried about you," Alan said.

"Now, how long until your next department physical?" Roger demanded.

Hanging his head, Alan answered "Seven weeks, and yeah, I'm worried."

"A bad report and your chance for Captain is dead, right?"

"'Fraid so."

"Alan, I know two women who can really help you. If I set up a time for you with them, will you do it?"

Alan stared at his brother bleakly, then let his shoulders slump. "Are either of them single?" That amounted to a resounding agreement from him.

"Absolutely. I'll set it up."


Roger was on his cell before his truck left the lot after dinner with Alan. Not surprisingly, all five women were willing to meet at Nancy's house right away.

"My brother Alan is fifty-eight. We're close, and I'm worried about his health. He's a police lieutenant and since being promoted, he has been less and less careful about his eating and his exercise. I got him to agree to meet with you, Phyllis and Nancy. Are you willing?"

"Is he single?" That was Claire, of course.

Laughing, Roger answered. "Yes. That was his first question, too. Alan never married. He had three different 'almosts' that ended badly for him and soured him on marriage. He has had quite a number of women, though."

"Is he involved right how?"

"Not that I know of. Hey! Are you thinking of ... I just wanted to get his health squared away."

Phyllis took the floor. "Roger, your brother has not done much about his health up to this point. Do you think just meeting with us will make a difference? I'm sure he has excellent workout facilities available to him. He must know what things he should and should not be eating. I'd love to work with him, but will it make any difference? Will he stick to it?"

"So, you're thinking of extra motivation, you slut!" Claire chided. Phyllis just stuck out her tongue.

"Tell us more about him," Nancy requested.

"Well, we're different in lots of ways. I'm an entrepreneur and he's in public service. I was married for thirty-six years. He never married. I was a virgin at my wedding. Alan had sex at seventeen. I'm a decent athlete for the fun level. Alan was a two-sport star in high school."

Inevitably "Is he hung like you?" came from Claire, followed by mixed groans and giggles from the others.

"When we were younger, we were often mistaken for twins."

"We've heard the differences," Carole said. "You look a lot alike. What other similarities?"

"I guess we have the same outlook on lots of things. Our folks were pretty strict, but they worked their butts off for us. I think we both have some leadership qualities. We both love the outdoors. We both live pretty simply. What else can I think of?"

"Is he OK with older women?"

"I've never asked him that. None of his relationships have been with a woman much younger, though."

"OK. I want him at the club just before closing on Friday night, again. Think he'll do that?" Phyllis asked.

"I'll make sure he does. Are you ... are you... ?" He was afraid to even ask. All he got for an answer was a grin until Claire piped up.

"You've got nice big balls, Stud, but how many shots a week are you really good for?" That elicited first gasps, then raucous laughter from the women and a blazing blush from Roger.


Once again, Carole insisted that they meet with Rebecca before their encounter with Roger. None of the others disagreed.

After hearing what they knew about Alan, Rebecca told them "Without a lot more data, I would say that your big challenge will be to change his perception of women in general. I don't know how deep seated the feelings may be, but he must view women as users and takers."

"Well, he knew Roger's wife very well. She wasn't like that?" Julie pointed out.

"Yes, but in his mind she may have been the exception. Remember, I'm working with limited background, here," Rebecca cautioned.

"We appreciate that, Rebecca," Julie said, patting the younger woman's hand. "After how perfectly you pegged Roger, I for one will go with your instincts." That got agreement from the others.

"Thank you. I appreciate that," Rebecca told them. "I have to tell you, this is like a breath of fresh air to me. Now, how to handle Alan..."

"Oh, none of us have any trouble handling it," Claire quipped, then stuck out her tongue as the others groaned.

"Yeah, fresh air," Rebecca murmured shaking her head. That produced laughter. "I think you should concentrate on doing something very significant for his benefit. If he can start to see you all as genuinely interested in his welfare and success, besides just his, uh, sexual prowess, I think he will become a better partner."

"There's a problem with that," Phyllis pointed out. "He is a recovery case. If, for example, our goal was for him to score highest on the Captain's exam, we will have to be pretty controlling and demanding."

"That's fine," Rebecca said. "If you succeed, he should recognize that what you did was for him. If he does not, dump him. I think you all know what to do to keep him from just walking away when the preparation gets rough."

There were some suggestive comments from more than just Claire at that. "One caution," Rebecca said when things died down. "If his physical condition is as borderline as his brother suggests, you might have to, uh, how shall I say this ... restrict the sexual activity to what is safe and prudent for his condition. Also, you do not want to, uh, exhaust him so it retards his progress."

"So, it's a balancing act, huh?" Phyllis commented. "Enough to keep him on track without wearing him out. Realistically, Rebecca, don't you think a man who has reached his rank will realize what we are trying to do and add his own willpower?"

"One would think so," Rebecca agreed. "I can tell you from experience, though, that scars from being jilted or abandoned can run very deep. Look at his brother. Roger's life was so 'entwined' with his wife's that it took the shock that you organized to pull him out of it. Certainly Roger, and assumedly Alan, are the kind of men who seek deep, committed relationships with their women. They are of the too rare breed who can be happy with permanent monogamy."

After Rebecca had said that, her demeanor noticeably saddened, and the others all caught it. "Have you found out something more, Rebecca?" Julie asked.

"I'm sorry, this session isn't about me," Rebecca countered.

"But we're all your friends," Phyllis assured her. "We hurt for you."

"No, I still don't have any real evidence," Rebecca said with a sigh. "It's just the continuing distance between us and the increased travel. He's spending more time at Corporate headquarters. I'm afraid he may be due for a promotion. That would mean a move and a big decision for me. Well, back to Alan."

Carole asked "If the brothers have the attitude toward women that you describe, are they going to want to pick one of us to marry?"

"Possibly," Rebecca admitted. "There are definitely extenuating circumstances, though. There is Roger's 'faithfulness' to his wife and Alan's deep scars. Look, you gals can probably make this 'stable' thing work. You've got all the tools."

"And the best professional advice," Claire added without her usual humor.


Roger had explained the reason, but Alan still thought it was fishy that he was to meet these women at 10:30 at night. It was at a health club, so nothing too strange could happen, but still ... He was tired. It seemed like he was always tired lately, and he didn't like it. Maybe these women really could do something about it. He was about at the 'try anything' stage.

He was met at the check-in desk by Phyllis, the one he was looking for. Roger had said nothing about her appearance, but she was impressive. She had the build of an amazon, but still came across as sexy and appealing. He wondered if Roger had done her. His mental questions were cut off when Phyllis introduced Nancy, who was just plain stacked.

The women led him toward the back of the workout area where there was a seating group. As he followed them, he did not know whether to look at the smooth strength of Phyllis's walk or marvel at Nancy's tiny waist and the way her body spread out above and below. In their brief, snug shorts, both women showed generous but marvelously shaped asses. When he had met them, he had to force himself not to gape at the beautifully filled sports bras they wore. As they walked, he just remembered that their exposed midriffs showed no rolls or bulges. These were women who knew what conditioning was about, he was sure.

The way he was concentrating on the bodies ahead of him, it took a while to notice that there was no one else in the exercise area. Later, he saw four or five people leave, but no one else came in.

Alan was dying to find out what was between these women and Roger, but they did not mention his brother and he was not about to ask. There was just a little chit chat before getting down to the professional part. Most of the questions were expected, but there were a few surprises. He could tell that Nancy was trying not to be judgmental about his admittedly poor eating habits.

They only put him through some short testing on the various machines. He had to stay a little longer than he would have liked on the stepper, but Phyllis explained that she needed to chart his pulse and respiration increases to know where to start him out.

It must have been 11:30 when they told him to go ahead and shower. He briefly wondered how they had access to the club after the scheduled closing. Something else to find out.

There was no way he could know how similar his shower encounter would be to his brother's. When he turned around because he sensed someone, it was just Phyllis and Nancy standing naked, but the shock was no less.

"We needed a better look at what we will be working with," Nancy explained with a smile. "We didn't want you to feel like an object, so..." She gestured at their bodies.

He was speechless. He was using too much mental capacity drinking in the sights before him to even consider talking. Between Phyllis's fat, bare labia and peeking clit and Nancy's large, full breasts and huge nipples, there was plenty to hold his attention.

"Also, Alan, we are concerned about motivation," Phyllis went on. "I'm sure you have started working out before, and I'm sure you know what is good and bad to eat. Roger is concerned that now, your job and even your life are at risk."

"M ... m ... motivation," he managed to stammer out. "I guess! Is this how you rescued Rog?" So far, even as he stared at their exposed parts, he had been too surprised and flustered to harden. Just the thought of his brother with the two women got the blood flowing South, though.

"Uh! Uh! Don't try to hide it, Alan," Nancy ordered. "We were starting to get concerned that maybe you had some E.D. That's a relief to see, so let it stick out proudly. Let's go into the whirlpool where we can talk some more.

The women each took a hand and led him from the shower area. As they turned into the hot, humid whirlpool room, he stopped in shock, which the women had anticipated.

"ALL RIGHT! WOO HOO! GOOD JOB!" That, of course, came from Claire, standing naked along with Julie and Carole at the edge of the tub. Pointing right at his jutting hardon, Claire exclaimed "OUTSTANDING!" That cracked everyone up, including Alan.

He was only allowed to sit on the edge of the tub like the women were, and he understood that trying to cover himself would not be well received. After brief introductions by first name only, Carole took over.

"First of all, Alan, the reason we have the run of the club is that Phyllis is the majority owner. As I'm sure you have guessed, something very much like this happened to Roger last Friday.

"You would be surprised and probably not happy about how much we have been able to learn about you in the last four days. It's all good except for that fat roll trying to hide your very nice cock and some numbers that are getting to the scary point."

With that introduction, Carole went through pretty much what had been said to Roger. "Alan, if you are going to be our partner, we do not want to be visiting you in the ICU or the cardiac ward. As you can see, we are all committed to being in the best possible physical condition. Roger is already in great shape.

"Also, we think that sharing our beds with Captain Alan Trent who looks like a police department poster model and can fuck all night is much better than with Lieutenant Alan Trent who just barely passes his physicals and can only make one of us happy about every three or four days. Therefore, we are going to make absolutely sure that you are the department's next captain.

"We know that you are a dedicated, disciplined man or you would not be where you are. Somewhere, in the last few years, the discipline has taken a hit, perhaps because of the way a series of heartless bitches treated you. Looking at us, you can guess how important top physical condition is to us. We know that you want that, too, and we are going to see that you get it.

"Not to tell stories out of school, but in one week, we have discovered that Roger is a woman's dream. We know that you share the same upbringing and the same values, and we want you in our lives. Please understand that some hard things we will do with you over then next few months are done out of genuine concern for you.

"Right now, we are all going to take some pretty embarrassing measurements. The process will be repeated until you reach the goals we will help you set. This will be intrusive and embarrassing, I assure you. Why would we require it? Well, the fact that you have let yourself deteriorate this much means that you need help correcting the problems. If you can't accept that requirement, we'll just apologize for displaying ourselves so brazenly and wish you a nice life.

"Why would you agree to do as we ask? Well, how about all of the sex that you can handle? How about warm bodies to sleep with instead of cold sheets? How about women who understand that a good man is to be respected and treasured, not used and discarded?"

Alan was beyond stunned. What they were asking would definitely be humiliating, but wasn't Carole right? Wasn't Roger right? He just couldn't seem to save himself by himself. Besides, there were five very appealing bodies that would be a great reward for success. The women all seemed intelligent, lively, and interesting.

"So, I have to get to these goals before... ?"

"Hell, no!" Claire shouted. "No way can I wait that long."

Carole followed up. "All we want is your agreement to follow the program. We're confident enough to think that the motivation we can provide will get you there."

Five women poking, squeezing, measuring, and tsk-ing over results was indeed humiliating. He could tell, though, that there was genuine care and concern behind what they were doing with him.

When what he thought was the last measurement had been finished, Claire shouted "Wait! We forgot the most important thing! Where's that tape measure?"

She got on her knees and took his penis in her mouth. It had softened, but she corrected that very quickly. When she got him to the point where he was jerking with each heartbeat, she took her mouth off of him and measured his length.

"Hot damn! That's going to feel good inside!" she exclaimed before taking him back in her mouth and finishing him off. Alan had had blowjobs before. He had stood naked and had a naked woman do him on her knees before. But he had never had an audience of four other naked women before. The embarrassment was almost enough to keep him from coming, but the others joined in by touching him or pressing their bodies against him, and that overrode his nervousness.

In a way that came across as loving and intimate, the women all helped him dress. When he was ready to leave, all but Phyllis disappeared, and she said "I get you for the night." The kiss that she laid on him squelched any question or objection.

It was already getting light outside when Phyllis rolled over on top of him and asked "Do you have any more brothers?"

"Nope. Just cousins, all married. Well, one is very unhappily married."

"We're not going there," Phyllis said quickly. "I hope you understand when I say that we would be open to more men that we could consider partners."

"Oh, I understand. I assume all of your sexual appetites are as strong as yours, and, God!, there's no way two of us could keep up."

"Yes, we're all just as horny," Phyllis agreed, chuckling at his rather euphemistic words. "Keep in mind that we're only looking for men the caliber of Roger."

"That's a pretty high standard," Alan said sincerely.

"We're very discriminating women. Uh, I probably shouldn't tell you this, but we have no intention of putting you through that measurement business ever again."

 
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