Gang of Five - Cover

Gang of Five

Copyright© 2009 by Shrink42

Chapter 7

Romantic Sex Story: Chapter 7 - 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  

Carole convinced Sean to join her in her king sized bed using the excuse that she might need help in the night. She did not have to say that they would not do anything with each other. That was understood. They fell asleep holding hands, though.

He did have to help her to the bathroom once in the night and iced her up after she went. The same thing was repeated in the morning.

As he was fixing breakfast, still quite early, Nancy arrived, helped him prepare it, and ate with them. "So, are you two like best buddies?" he asked.

"We've known each other a long time," Nancy answered. "She holds my financial future in her hands, too."

"What do you mean?"

"Didn't Carole tell you? She used to work in research at a brokerage before she retired. She knows all the good stuff, and she really uses it for us, instead of just trying to pump commissions like the brokers do."

"Us? You mean you and Phyllis?" he queried

"Yes, and Claire and Julie, too," Nancy replied. "She has all of our money in these funds that she and Julie set up. Oh, Julie is a tax lawyer, so it's all nice and legal. Anyway, we are all making so much money!"

"Wow!" Sean said, looking at Carole in obvious admiration. "I was right. I thought you were some kind of genius from some of the things you told me. I thought you were also a witch from what you got me to do."

"That sounds interesting," Nancy said with a giggle. "Tell me more."

"Oh, I just got him to take a bath with me. We talked a lot about sex and pride and confidence. It was the best thing I can remember in years. He's a wonderful young man with a very nice body - great cock, too?"

Nancy was staring with her mouth open, and she started to shake her head in disbelief. "Guess I'd better show you," Carole told her friend. "My ankle is quite a bit better. I think Sean can get me into the hot tub. Let's go."

"Carole, you can't expect me to..." Nancy objected. This time, it was Sean who was staring and speechless.

"To undress and join us in the hot tub? Sure I expect you to. Help me up, Sean."

As he was helping her get on the crutches, Carole whispered to him "Act like it's normal and natural. Make it so she can't refuse."

Nancy had come a long ways. Her instinct was still to go all shy and refuse. She knew, though, that Carole knew the truth about her. She also sensed that being casual and open with the young man was important to her friend.

When Sean saw Nancy shakily start to undress, he understood a little more of how Carole had gotten him to cooperate the night before. Maybe she really was some kind of witch.

Of course, Sean got hard right away and stayed that way. He ended up lifting Carole down into the tub. With both of them naked, it was almost enough to set him off.

It took quite a while for Nancy to relax enough to talk. Sean could not know that it was baring herself to someone only a little older then her grandsons that bothered her, not the nudity per se. He would later learn that it had happened before, but some time ago. He did not think that she should be ashamed of her body. She was only a little overweight. It looked like she worked out regularly. There was not the sort of slack look that he expected to see on an older woman. Of course, all he had to go on was some nudist pictures on the Internet. He could not keep his eyes off of her substantial, full, large-nippled breasts as they floated on the water. She noticed and blushed several times.

"Sorry for staring, Nancy," he said after a while. "It's just that you're only my second live naked woman."

"Poor guy! Your first ones should have been some nice tight little teens," Nancy answered back.

"Carole already said something like that," he responded. "She's been telling me how I should be proud of my body. You should, too."

"Oh, I am, Sean," Nancy assured him. "It's just..."

"It's just the female need for constant reassurance of her sex appeal, Sean," Carole explained. "Never, ever forget it and you will do fine with women."

Changing the subject, Sean said "It looks like both of you work out. Nancy, your legs and your ... bottom look nice and firm."

"Thank you, Sean" Nancy said, "But you're embarrassing me, talking about my body like that!"

"Oh, sorry! I guess you women are the only ones who can talk that way, huh?" That earned him several facefulls of water.


Going home late Saturday morning was strange for Sean. He knew that his parents always slept in after the parties, so he did not hurry. He also knew that neither parent would be in a particularly good mood.

In recent years, he had always felt his stress level rise with proximity to his house. This, time, though, he felt a calmness, a kind of serenity that he very much enjoyed.

Apparently, his mother was much more observant than he gave her credit for, even with a hangover. "There had better not have been any girls involved last night, young man. I don't like that look on your face."

"No girls, Mother," he answered, wondering why he did not feel the usual tension at her challenges. "When I go out with a girl, I'll be sure to tell you."

"When you go out with a girl, it will be when I tell you that you can, Mister," she snapped back.

"Does that mean I will have to wait until I'm twenty-one?" He had never, ever asked anything so impertinent before, and she just stared at him.

"That's my decision to make," she countered, but he could see the uncertainty on her face. Confidence was great, but maybe it could be dangerous, too.


Unbeknownst to Sean, Carole had the Gang of Five for their usual Sunday brunch, and the topic of conversation was, of course, Sean. "When do Claire and I get our turn?" Julie demanded, her tone quite serious.

"You mean Alan isn't keeping you satisfied? Or Brad? Or Roger? Or Dale?" Carole shot back.

"Oh, all the guys are great," Julie said, and then with emphasis added "As you well know!"

"Yeah, we really are fortunate to have such good fuck buddies," Claire giggled. "Wouldn't hurt to add a fifth, though, especially a young stud. Just imagine him doing all of us in one night!"

"Claire!" Carole objected. "The last thing we want to do is make a gigillo out of a nice young man. Not to mention the legal issue."

"Well, what do you want to do with him?" Claire challenged.

Nancy took up the challenge. "I haven't spent nearly as much time with him as Carole has, but I see a really great young man who needs some help he's not getting at home. I think we should make Sean a group project."

"A project?" Julie asked.

"Yes. I think it should be our goal to help him achieve several things. First, he should continue his good grades so he can get the scholarship he wants so badly. Second, we should train him and support him so he has the first spot on the wrestling team for his weight class next season. Third, we should build his confidence and his social skills so he is the most desirable date in his high school."

"Wow. That's a tall order," Julie commented. "Why would we want to do this?"

"Besides the fact that we can always use something to hold our interest, he is just the most likable young man you will ever meet," Phyllis jumped in. "I've only met him once, and I joked about wanting to adopt him. It wasn't that much of a joke, though."

"I like Nancy's idea of a project," Carole said. "Phyllis, does he have the body to add a lot more strength?"

"Definitely. I'd like to get a look at his father and at his uncles on his mother's side, but I'm betting there is some pretty good beef in his gene pool."

"Could you spare the time to really push him through the summer," Carole asked Phyllis.

"With what some broker genius is making on my investments, I'm not sure why I bother to work any more," Phyllis said to sounds of agreement from the others. "Say, Claire, would you teach him to dance? Besides the social value, it is good balance and body position training."

"Only if I get to skinny dip with him every time," Claire smirked.

"Who said our sexual peak was at forty?" Julie murmured just loudly enough to be heard. There was more laughter.

"Say, how many of you are really committed to your yard care companies," Carole asked. "He seems to be quite mechanical."

"Yeah, and once we got him to our house, we could get his pants off!" Claire chortled. The laughter at that was mixed with groans and jeers. "As far as I'm concerned, he's hired." That sentiment was unanimous.

"Uh, girls," Carole said quietly, "let's not add him to our stud list until we talk about it and agree together, OK. And I think he should agree up front, not in the heat of your seduction."

"Seduction! I sure like the sound of that," Claire quipped. "In fact, I think I can even remember when I used to be able to do it."

"Since wrestling has ended for the year," Carole told the others, "Sean will be stopping by after school every day. Phyllis, you be here this afternoon so he can start a good workout program. Do I have enough equipment here?"

"Plenty. I'll be here."

"I think you should come back Wednesday and Friday to check on his workouts. Claire, you get Tuesday, and Julie Thursday."

"That doesn't seem fair," Julie complained, only partly joking.

"Once the lawn work starts, he'll be at all of your houses," Carole assured them.

"I need him right now," Julie insisted. "The jerks I had last year never came by to cut back some of my bushes and the dead decorative grasses. I was going to call them this week."

"Then why don't we have him go to your house Thursday after school. Does that sound fair?"

"I'll have him check that the hot tub is working right, first. That's the most important thing," Julie quipped.

"I know that you're all having fun, and I shouldn't have to say this, but I will," Carole stated seriously. "Sean is a nice, INNOCENT young man. Please don't escalate beyond things that have already happened with him until we have talked it out. I'd like to have him fucking my ass off as much as the rest of you, but he is not one of our older guys."

"You're right, Carole," Julie said quickly. "It's all just horny fun."

"Um, now that I've given all those cautions," Carole said, "I do think we should keep him naked as much as possible."

"Carole has seen the light!" Claire chortled. "I'll bet you're thinking about that Transformations place, huh? And about what we did with Alan?"

"Yes, I am. Part of their theory is..." Her explanation took several minutes. They talked for quite a while longer about plans for Sean. Some of the plans produced more ribald laughter and giggling.


When Sean stopped at Carole's after school on Monday, he apologized for not being there to help her Sunday after he had to go home on Saturday.

"It's a lot better, now. Nancy was able to help me all I needed. I can't tell you how much I appreciated your help, though. I don't know what I would have done without you."

At that moment, Phyllis walked into the room and gave Sean another hug. "I have a feeling, Sean, that you are going to make some real changes in five women's lives. We're going to do our best to make changes in yours, too - good changes."

"Phyllis is an expert at building bodies for best performance. She knows all about conditioning and strength training," Carole explained. "Our gang has decided that you are going to be number one on the team in your weight class next fall."

"But ... but there's a senior and a junior!"

"Doesn't matter," Phyllis assured him. "If you're willing to put in the work, we can help you do it. Actually, you will probably be up two or three weight classes with the added muscle mass. You will be so buff the girls will be running into each other in the halls from gawking at you."

"Riiiight!" Sean retorted. "Do you really think I can improve that much?"

"Do YOU think you can? That's the critical factor," Phyllis told him. "We've got to build your confidence as much as your body."

The next hour was filled with squeezing, prodding, and stretching his body and with testing his limits on several different exercises. He had continued his workouts when wrestling ended, but what Phyllis was getting him into was a whole different level.

Besides what he thought was a ridiculously aggressive group of sets, Phyllis told him that he would be running six days a week. Carole instructed him to start moving some of his clothes to her house so he could start running in the morning, end up at her place, do the strength work, then shower and dress for school.

"I have one concern, Sean," Carole said. "Will these workouts plus all of the yard work hurt your grades?"

"Yard work?"

"Oh, I'm sorry. I didn't get around to telling you about that. You now have five lawn care customers. They may end up recommending you to others, too. You start at Julie's Thursday afternoon."

"Wow! That's great!"

"I know how much you want some independence," Carole said. "Are you dodging the question about your grades?"

"Oh, no. I'm in good shape. Many days I don't even have to take anything home. Since I have to be home for dinner, I'll have plenty of time to finish in the evening."

"That's great. Well, let's get in the hot tub so you can make it home for dinner." After the session with Nancy, Sean had assumed that he would be tubbing naked with all of the women at some point. Apparently, it would be immediately.

Phyllis showed none of the reluctance to strip that had bothered Nancy. Noticing that, Sean told her "I can see why you can just casually tell me to strip. You can do it yourself so easily."

"Years and years in locker rooms and training rooms make one almost like a doctor," Phyllis pointed out. "Carole probably didn't tell you, but I started all of the women on this pride campaign that she laid on you. Thanks for plagiarizing my stuff, Carole!"

It was at that point that Sean noticed Phyllis's completely bare crotch and let out a groan. "I don't have too many parts of me that are real sexy," she explained. "My pussy is perhaps the sexiest part, so I wanted to emphasize it."

"And to do that, you have to be naked, right?" Sean quipped.

"Thanks for giving me a chance, Sean," Phyllis said brightly. "By the way, have you thought any more about that adoption offer?"


Sean had to bring some school clothes with him as he ran to Carole's Tuesday morning. Since it was only half a mile, he did not get them sweaty or wrinkled. He ran for three more miles, then did the workout chart Phyllis had made. He was more than happy for the shower and the good breakfast that Carole had waiting.

"I have to be up well before the market opens," she explained. "I watch the futures very carefully. Also, some stuff on foreign exchanges."

"Say, Carole, I have about three thousand dollars. Can you invest it for me?"

"How did you get that much?"

"When I outgrew those golf clubs I never really used, I just sold them for nineteen hundred. Dad saw this titanium bike advertised, so he bought me one. If I had dared sell it, I would have twice as much. I got seven hundred for my old one, anyway. Like I told you, they kind of throw money at me, but I usually don't spend it."

"Wow! I'd be delighted to handle your money! How conservative or how aggressive do you want to be? How many chances are you willing to take?"

"I'm willing to take any kind of chance, if it could help me break free of them."

"But that means risk. You could lose it all," she warned.

"How much could my money grow in a few years?" he demanded. "If everything went right, I mean."

"That's hard to say, Hon," she hesitated. "I've got one new fund that all of the women are putting a part of their money in. The people running it achieved a one-hundred to one stock price growth multiple on a previous similar venture."

"Then I want you to put all of my money into that. If I lose it all, I'm no more stuck with my parents than I am right now. If a miracle happens, I could walk away when I reach eighteen."

"I guess I didn't quite understand just how badly you want out, Sean. Sorry. Your reasoning is solid. I'll do it for you, of course. Where is the money now?"

"Hidden in the framing of the basement of our house," he told her.

"Not in a bank?"

"I couldn't get an account without their signature. I don't want them to know what I have."

"Oh. I hadn't thought of that," she said thoughtfully. "I'll have to come up with a clever way around that problem for an investment account for you. So, as much as they keep track of everything you do, they didn't know you sold those things, huh?"

"I'm sure they don't throw money around in their businesses," he answered, "but it's like anything they give to me is out of their concern. They've done their parenting thing and they can go on to the important stuff."


When he arrived at her house after school, Carole was waiting with Claire, whom she quickly introduced. "Besides owning a very successful spa, Claire is a highly qualified dance instructor."

"Dance?"

"Sean, Honey, have you ever been to a school dance?" asked Carole.

"Can't dance."

"Well, every girl loves to dance. What better way to get yourself noticed?"

"My mother won't let me go to dances."

"We'll worry about that later. I'll bet we can come up with a solution. Let's have your first lesson?"

Somehow, the next hour plus seemed as exhausting as a wrestling match. At the very end, Claire pressed herself close to him and told him "I wanted to do this with us naked, but Carole is such a fuddy-duddy."

Claire was shedding her clothes before Carole could even mention the hot tub. Her body looked like a dancer's with strong ass and legs and a slim torso. He was to see for the first time the phenomenon that many smaller-breasted women have remarkably large nipples.

To read this story you need a Registration + Premier Membership
If you have an account, then please Log In or Register (Why register?)

Close
 

WARNING! ADULT CONTENT...

Storiesonline is for adult entertainment only. By accessing this site you declare that you are of legal age and that you agree with our Terms of Service and Privacy Policy.