Gang of Five - Cover

Gang of Five

Copyright© 2009 by Shrink42

Chapter 6

Romantic Sex Story: Chapter 6 - 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  

As she closed her laptop, Carole let out a contented sigh. She had just closed the week with gains for herself and her friends that few investors saw in a month. That was certainly satisfying.

The year since her retirement had been a very, very good one, even if it had started a bit slowly. The building of the Gang's 'stable' of men had been fulfilling in more ways than just the great sex the Gang and the men all enjoyed. The project of getting Alan his captaincy and rebuilding his health had energized all of them. Dale had been somewhat of a project, too, and at least emotionally, he hardly seemed like the same man.

There was just one problem for Carole; the projects had been so fulfilling that she found herself yearning for more of them.

One of the things the Gang of Five all did for each other was to encourage discipline and consistency in their daily lives. For Carole, that meant that her workout time came right after the trading day closed. In fact, it had become her habit to wear shorts and sports bra for at least the after lunch activity online. Today, she had shut down early, knowing that there would be no more trades for the week.

Of course, most days went by without any actual trades for any of her 'funds'. She filled the time with research while keeping one eye on the indices and the list of some thirty securities that comprised the six funds. The research could have been done any time, but to Carole, keeping some semblance of a 'work day' suited her best.

Rather than heading for the shower as she ordinarily would, she shed the shorts and T-shirt that she worked out in and donned a sweatsuit. Although it was bright and sunny, there was a definite chill in the air.

There were lots of tasks to be done to get her nice yard ready for the warm season. She would call a landscaping company to do it for her. It was only the end of March, but for some reason, the grass had started growing extremely early and she decided to try her hand at mowing. She had done it before and the mower was of good quality and self-propelled. Mechanical skill was not one of her bragging points, but anyone could run a lawn mower.

It would not start. In frustration, she gave the starter cord a mighty yank, the only result being her loss of balance. Able to barely keep from falling, she stepped backwards, flailing her arms. The result might have been no more than an awkward moment except for a sprinkler head. It was recessed, and the natural buildup of turf over time had left a hole big enough to catch her foot.

When she hit the hole, she felt instant pain from a twist of her ankle. Her balance gone, she fell heavily on the asphalt of her driveway, taking the brunt on her hip and one elbow. There was no way she could stifle her cry of alarm, followed by a moan from the pain.


It was a gorgeous Friday afternoon, one of several really nice days in this warmer than usual spring. Because he often preferred the mile-and-a-half walk home to a bus or bike ride, Sean had passed the house many times. This was the first time he had seen anyone in the yard, though. A woman, clad in sweats, was trying to start a lawn mower. Apparently in anger and frustration, she gave the starter cord an extra hard pull. The only result was her staggering backward, then falling over on her side on the driveway.

Hearing an obvious cry of pain, Sean fumbled with the latch on the gate in the fence that surrounded the yard, then hurried over to the woman. He had always thought that asking 'Are you all right' in situations like this was stupid in the extreme. Instead, he set down his backpack and knelt beside the prone woman.

"Do you think I should call 911 for you?" he asked.

The woman just looked at him for a moment, her facing showing her pain. "Should I know you? Are you a neighbor?" the woman asked.

"Not a close neighbor," Sean answered. "I live about a half mile away, and I like to walk home from school on nice days. My name is Sean Massey. I'm a sophomore in high school. I'm fourteen and I'm an only child. I like computers and I'm on the wrestling team."

"Well, Sean, I don't think I need medical help, but I could use a good, strong wrestler to help me into the house."

"Did you hurt your hip?"

"Some, but I think that's just a bruise. It's my ankle. I really twisted it. By the way, my name is Carole Gruden. Let's skip the age stuff, OK? How about you use some of those wrestling muscles to help me sit up, first."

Carole groaned loudly with the effort, but it didn't take long before she was sitting. She prodded her bruised hip and decided there was nothing really wrong. "I doubt if I can walk, Sean."

"Well, if I get your arm over my shoulder, maybe you can sort of hop on one leg," he suggested. "Maybe ... I might be able to just carry you. You're not very big. I'm afraid I might stumble or drop you, though."

"First, let's see if I can stand up," she decided. After a couple of awkward, abortive tries, he got behind her with his arms under hers. As he hauled her up, his arms brushed her breasts, making him gasp.

When she was upright on one leg, leaning heavily on him, she said gently "Don't be embarrassed, Sean. My breasts are just part of me. I know it just happened while you were helping me. I'm not at all bothered."

She stood for a couple of minutes, breathing deeply, before she tried to put weight on the injured ankle. She gasped and sagged against him. "Th ... that's not going to work. Damn! I don't want to be laid up."

Sean appraised her carefully. She was several inches shorter than his 5' 10" and quite slender. Impulsively, he told her "Hold on. We may have to do this in a couple of shots."

Her arm was already around his shoulder and his around her back. He bent down a little and with the other arm under her thighs, he lifted her and walked as quickly as he could to her little porch. There, he had to set her down with her bottom resting on a railing and a post for her to hang onto. His muscles were definitely complaining, but he also did not know if the door was locked.

She had made no noise as he was carrying her, perhaps through fear of causing him to stumble. She gave a little groan when he set her down, then said "Wow! You ARE strong. The door isn't locked, but it won't stay open by itself. Get it so it isn't latched, then we can push it open when you're ready to lift me again."

It took two or three minutes before Sean felt ready. When he picked her up again, it was quite awkward getting them through the door, and he had to set her down again, this time on a bench in the entryway. "Sorry," he panted.

"Sorry? Nonsense. I can't believe you can just lift me like that." It must have been the combination of pain, embarrassment, and frustration, but Carole's bladder was suddenly complaining strongly. "Um, I really have to go to the bathroom, so can you take me there?"

"Sure. In a minute." Minutes later, when he stood her in front of the toilet, he turned to walk out.

"Sean, I'm sorry. I ... I just can't sit down by myself. Please! I can't hold it much longer."

As he went back in, he saw her sweatpants and her panties pushed down around her knees and a panicked look on her face. Forcing himself not to look where his eyes were drawn but at her strained expression, he eased her down and turned to leave again. Her stream hissed loudly into the bowl before he was out the door.

While waiting outside the bathroom door, he heard sounds of her wiping herself, then a groan and the toilet flushing. "Did you hurt yourself?" he called out.

"Sean, please come in here." When he was in front of her, she told him "When I twisted to reach to the flush handle, it really hurt my hip."

"Why didn't you let me do it?"

"Well, I'm bare-assed here, and..."

"Uh, Carole, don't you think you should have a doctor check you?"

"I really don't think I am injured badly enough for that. I just hate being so helpless!"

"Is there a friend who could help you?"

"Oh, I've got some really close friends. In fact, let me call Phyllis. She'll know if anything is broken. I need to get to my chair and get some ice on this, first. If only I could..." She tried to raise herself enough to pull her panties up, but only generated another groan.

"Shit! Sean, you're so strong. You seem to be a very nice, respectful young man. Can you stand seeing some parts of me that are usually covered?"

"I ... I ... what do you need me to do?"

"Take my shoes and socks, my sweats, and my panties off, please. I just can't bend over to do it."

His hands were shaking a little as he complied, again trying not to stare at the fur patch just visible between her closed thighs. When he was done, she told him "See that robe on the back of the door? Help me stand up, then bring me the robe. Can you do that?"

Finally able to think about something besides her pain, Carole was noticing just how shy, even fearful Sean seemed. In spite of that, though, he was completely respectful and very concerned about her well-being. She could not help liking the boy. She certainly could minimize how much of her he saw, but nudity was no problem for her any longer. The only question was how it would affect him. She would see what he was really like.

As he helped her stand, he again looked pointedly at her face. This time, she was able to give him a small smile between grimaces. When she was standing, he turned to fetch the robe. As he turned back with it, she was just shedding her bra, everything else now in a pile on the floor.

She saw the shock on his face, quickly followed by a bright blush. As much as he was obviously trying to look only at her face, his eyes had to dart downward a few times to her breasts. For her part, she refrained from checking out the bulge that she was certain strained his pants. Showing remarkable self-control, he held out the robe for her to slip on.

When he picked her up, she felt so different. Knowing that she only wore the robe did not help. There was nothing he could do about his erection until he stood her up in front of the recliner in her bedroom. As he eased her to a sitting position, he could see her look right at his bulge, and he almost dropped her.

He quickly turned away, but she said his name softly and asked him to look at her. "It's alright. It's just natural and you can't help it. I'm not offended or upset, OK?"

"Um, but I shouldn't get ... I'm not supposed to..."

"Does your mother get after you when you get hard?"

Unable to believe the conversation, he wished he could just get out of there. He could not leave the woman practically helpless, though. "Um, yeah. She..."

Sensing that it was not a good line of conversation, Carole interrupted to say "Ohhh, I really need some Ibuprofen and some ice on this." She proceeded to tell Sean where to get everything and how to make up an ice pack. When she was all set up, she asked for the phone so she could call her friend Phyllis.

"I'll go take care of your lawn," he offered.

"But it wouldn't start," she cautioned.

"Is it the first time you tried this year?"

"Yes, it is."

"I think I can get it going. Where would I find some tools?"

Carole had been talking to her friend for barely ten minutes when she heard the mower start up and she exclaimed in amazement to Phyllis.

By the time Sean finished the yard and stowed the mower in the garage, there was an SUV parked out front and he assumed Carol's friend was there. When he came into the house, he met Phyllis, who was sitting on Carol's bed chatting with her. She seemed to be the about the same age as Carole, although he was not good at guessing that age. There was little resemblance between the two women, as Phyllis was both taller and heavier built.

At first, Phyllis just looked at him with a quizzical grin. Unable to stand it, Sean finally said "I guess Carole has been giving you a blow by blow, huh?"

Phyllis grabbed Sean, pulled him down on the bed beside her, and somehow hugged his face to her substantial bosom. "Can I adopt you?" were the first words she said to him.

The women were giggling, but Carole stopped when she saw Sean's face. Noticing her friend's change of demeanor, Phyllis pushed back from the hug and with her hand under his chin, raised his face to stare at him.

"Nice to meet you, Phyllis. That was some kind of hello," he said, trying to cover his reaction to the adoption comment.

The women shared a look, then Carole said "Phyllis brought me some crutches. That means no one has to carry me. I'll still need help getting up and down, though."

"There is nothing broken and the ankle is just twisted, not really sprained. In a few days, she will be as good as new," Phyllis announced. "Of course, it hurts like hell right now. And I have an appointment for which I'm late. I'm sorry, Carole. Can you get Nancy or someone to help you out?"

"I'll manage, I'm sure, Phyllis. Thanks so much for checking me out. It's a relief to know that it's not bad. Sure couldn't tell from the way it felt."

When Phyllis had left, Carole explained "Phyllis was an athletic trainer and she owns some health clubs. She's supposedly retired like the rest of us, but you would hardly know it sometimes. Let me call Nancy and see if she can come over this evening."

Sean could tell that the response from Nancy was negative, and Carole explained "Nancy was just leaving to babysit for her niece. There is no way she can find a replacement this late. Is there any chance you could stay with me this evening? Nancy can come over when her niece gets home and stay the night. I'll be happy to pay you."

"No need to pay me. I need to be home for dinner, but I'm supposed to be away from the house tonight anyway. My parents have their group of friends coming over."

"Away from the house? Where were you going to go?" Carole asked

"I'm supposed to be staying overnight with a friend. I'll just show up there late."

"Would your parents know if you just stayed here overnight, instead?"

"Not likely. Their parties last forever and they have never called. It's funny. Usually, they watch me like a hawk, but not on their party nights," Sean explained. "Sure. I can stay over. I'll let my friend know I won't be there. Will you be all right when I go home for dinner? I really have to be there."

"I'll be fine. Let me know when you'll be back and I'll order in something for me," she told him.

"I can get you some dinner," Sean insisted

"You cook, too?" Carole exclaimed in genuine amazement. "I'm trumping Phyllis's adoption offer. Will you marry me?" As Carole chuckled, she heard Sean say softly but seriously "Too bad. I liked that adoption idea."

"They want me gone by seven thirty, but I could get here before seven," he informed her, hoping his previous comment had not been heard.

When Sean had left, Carole had a lot to think about. She really liked the young man and she could tell that he had his share of problems, mostly his parents.

Because of her fascination with the Transformations idea, Carole had dug up anything she could find about it. One of the claims made was that a period of nudity in the presence of the opposite sex helped to build the subject's self-confidence by greatly reducing concerns about their body. During the past year, she had certainly seen proof that the theory worked.

Sean seemed to need some confidence building. He had a very nice body, from what she could see. She had been looking for something 'significant' to do. She wondered...


Sean had helped Carole to the kitchen where she supervised as he prepared soup, salad, and sandwiches. As she sat and ate, Sean said "This house seems a lot nicer than others in this neighborhood."

"Well, it was built at the same time as the others and it's not the biggest model. It has had a lot of work done on it, though."

"Did you buy it new?"

"Yes. I've lived here for thirty years. Is your parents' house nice."

Sean grimaced a little. "It's over on the golf course. My mother reads all these magazines and she's always changing something or buying some new furniture. I know she's, uh, irritated that we don't have the most expensive one on the course. They really love the location, though, so she makes up for it with landscaping and inside stuff."

"Do you take care of the landscaping?"

"Wish I could and get paid for it," Sean grumped. "It doesn't look right if the landscaper's truck isn't out front every few days. Having your son do the lawn isn't ritzy enough."

Carole was wondering if she could find anything to talk about that did not produce negative comments about his parents. She was getting weary from the pain, so she had him help her back to her chair, get her more pills, and ice her ankle again. She invited him to watch TV with her, and coaxed him to sit on the floor, leaning against the front of her recliner between her spread legs.

He felt embarrassed and uneasy, but when she started running her fingers thru his hair, it occurred to him that she was probably lonely for some companionship. From their conversation so far, he thought that she was a very nice, very bright lady who seemed to be genuinely interested in him.

Sean could not help comparing Carole to his grandmothers. The best description of Grandma and Grandpa Massey was 'blue collar'. They were nice to him, but Grandpa's world centered around sports, hunting, fishing, and cars. Only the cars appealed to Sean, so conversation with Grandpa Massey was difficult.

Grandma Massey watched every possible TV sitcom and game show. They had Tivo so she did not lose out when two 'good' shows aired at once. Sean watched limited TV, so again, there was a communication problem. Why couldn't Grandma watch the History Channel like he was watching with Carole just then? Or at least an action movie.

It was hard to even think of his mother's parents as grandparents. His maternal grandfather was a high-powered executive and his wife had been on the society pages several times. He guessed that his mother was determined to have a house like the monstrous one she grew up in. Except for gifts, Sean had very little contact with and absolutely no warm feelings for his maternal grandparents. At least the Masseys laughed and joked and showed that he was welcome.

The evening, in fact, the whole day, was so strange that Sean could hardly relate to it. Somehow, though, Carole made him feel comfortable. He wondered if this is what the term 'feeling right at home' meant.

As she ran her fingers through Sean's hair, Carole's pain subsided enough so she could do some more thinking. She hoped it wasn't just because he had 'rescued' her with such sensitivity and poise, but she felt genuine affection for the young man. It was obvious that he was living, and apparently achieving, without being close to anyone. That was a real shame. It seemed like a classic case of a 'poor little rich boy'.

How could she manage to get close to Sean? Having him stay overnight was definitely a good start, but something in her wanted more 'instant intimacy' than that. He had seen her naked briefly this afternoon, but that was in the midst of her 'rescue'. Maybe ... Using nudity had certainly gotten through to Roger, Alan, Dale, and Brad, and established close relationships very quickly.

Because she had tried to mow the lawn, she had not showered after her workout, something that never happened. In fact, she had worried a few times about him detecting her odor. The need to get clean meant that she would have to get naked. She could not do much by herself yet, so there was her opportunity.

When a show ended, Carole said "Sean, I really need a bath. There's a nice hot tub out on the patio, but I don't think I can step into it. A shower won't work very well, either. Help me to the bathroom, will you please?"

Sean wasn't nervous about the request. After all, he had already been through the bathroom routine. This one turned out to be different, though. He helped her to the toilet, first, but then he got another shock.

"I'm afraid I can't go with this bulky robe on. Oh, well, you've seen me already. Here." She shed the robe and tossed it away. "Help me sit down."

As soon as she sat, she told him "Would you start running the bath for me, please?" Thinking that she did not want to push him too far, she waited until the water was running in the tub before she let her urine stream go.

When he helped her up from the toilet, Carole said "Forget the crutches. Help me hop over to the tub." When they got there, she said "Sit me down on the edge, first."

When she was seated, she told him "Help me turn so my feet are in the tub. Then, you're going to have to use those nice muscles to set me down in there."

Sean very nearly panicked, totally flustered about where to hold onto her to turn her and set her down. She chided him gently, and without too much fumbling, she was seated with the water rising around her. "Do you think it's good to get the bad ankle in the hot water?" he managed to ask. "After all, you've been trying to ice it."

"As long as I know it's not sprained, heat won't hurt it for a while. Are you OK? This is a pretty big shock for you, isn't it?"

"Y ... yeah. It sure is. Call me if you need anything," he said, starting to leave.

'No! Please stay!" Carole said almost frantically. He stood uncertainly for a moment, then nodded. He just stood motionless while Carole seemed to be trying to decide something. He was standing close enough so she could reach out and take his hand.

"Sean, I want you to undress and get in here with me," she said suddenly. That was a spur of the moment decision. She had opened herself to intimacy by undressing in front of him. It was clear that he was too shocked and nervous to share that intimacy the way she wanted.

"Wh ... what?!"

"You're such a wonderful young man. You've been so helpful and so respectful today. I'm so impressed. I admit that I've been pushing, and you have responded perfectly. Look, I'm not asking you to have sex or anything. I sense some real hurts in you and I really want you to talk about them. If you join me, it will be so intimate. It will be a way that we can share some important things."

"I d ... don't think I can. I'd be..."

"I expect you to have an erection, Sean. Please, don't be embarrassed about that. As we talk, it will go away, I'm sure."

Talk about unreal! As if the rest of the day had not been strange enough. Sean could feel a connection with Carole, a connection he did not have with any other woman, or any other person, for that matter. He was intrigued by her. Obviously, her body was not what it once was, but she was still a very attractive woman. She also had a caring attitude that just poured from her. Frankly, it was something that he was starved for.

Because of what he felt between them, he wanted to do what she asked. As he stood there, his mind spinning, the thought of someone who would really listen, maybe even care, pushed the embarrassment of exposing his cock to the background. Somehow, he knew that she would be gentle, respectful.

Kicking off his shoes and pulling his shirt over his head happened without him really realizing it, he was so deep in thought. It was only as he undid his pants that he stopped, more than a little shocked at what he was doing.

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