Gang of Five - Cover

Gang of Five

Copyright© 2009 by Shrink42

Chapter 25

Romantic Sex Story: Chapter 25 - 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  

Once fully seated, she kissed him hard, then said quite calmly. "If you are ever my son-in-law, this will make it even more interesting. Oh, I had my tubes tied. I was checked after the last party, and I made my husband wear a condom since then."

Hardly able to believe what was happening and the sudden change in the woman's demeanor, Sean just tried to hold still, resisting the urge to thrust into her.

"I was a virgin on my wedding night," Celeste told him. "My second man was your father, at the first party we attended. Why did I go? Well, I have to confess to some curiosity. The main reason, though, was because I felt my marriage slipping away. I thought I could hold onto him if I went along."

"Did it seem to help?" he was able to ask, some composure returning.

"I admit, there was a thrill, at first. And he ... he ... Oh, Hell! Why am I worried about telling you anything," she said with a mirthless laugh. "After the first few parties, he fucked me like on our honeymoon. I thought my marriage was saved. I did not like what I had to do to save it, but..."

"I take it his, uh, renewed interest didn't last?"

"No. And when I said 'no more parties', I thought he would leave right then."

"Is he doing his own parties?"

"I suspect so. When I first made him wear a condom, he just grumped a little, but didn't refuse," she recounted.

"I take it he still likes doing it with you?" Sean asked, trying to think of something to keep the conversation going.

"Either that, or he doesn't feel like finding someone else right then," she growled.

"Are you able to seduce him when you want it?" he asked.

She froze and just gaped at him. "Seduce? But ... I shouldn't have to ... he's..." That was as far as she got.

"It just seems that if he really liked the parties, maybe if you acted more like at the parties, he might, you know..."

"Sean, can we ... can we not talk about him right now? I should never be with you like this, but I am, and damn! I want a good fucking so bad!"

All along, Sean had been thinking about how he could tell his women about this. Celeste really had surprised him. Before he knew it, the damage had been done. Of course, this was an eventuality that had not been considered when they all discussed this encounter. He needed to decide, and quickly.

Later, he could blame it on teenaged hormones, and that would have been justified. He grabbed her blouse at the closure and just pulled, releasing two buttons and popping two others. Removing a bra was something he had not had much practice with because the Gang was usually eager to undress when with him. He did recognize that it closed in front, and that made it easy to get rid of.

Apparently fearful for her skirt, Celeste unbuttoned it at her waist and told him "Lift it over my head." When the skirt was gone, he grabbed the waistband of her panties and rather forcefully ripped them off. Her little shudder at that could very well have been a small come.

Their family room furniture was leather, and there was a large wheeled ottoman in the set. He did not want anything romantic, and a bed would connote too much affection. The ottoman was perfect.

She gasped when he just leaned forward and stood up with her still impaled. When he grasped her ass cheeks firmly, purposely spreading them and sliding his fingers into her crack, she let out a long groan. Maybe it was showing off his strength a little, but he started boosting her up and down on himself as he approached the ottoman.

As soon as he laid her on her back, he began thrusting long and hard. Even though he intended it to be just fucking for effect, he could not forget the loving teaching of the Gang, and almost subconsciously, he changed his angle, rotated around, and ground their pubic bones together.

She screamed under him. It was long and piercing. He wondered how she could emit such a steady note the way she was thrashing and shuddering.

The scream was so shocking that his own urgency was reduced and he was able to keep right on plunging. Her legs had fallen from around his waist when she came, and he moved them up over his shoulders. She was bent almost in half and he was leaning against her legs at an angle.

By the time he came, she was almost limp. He was pretty limp, too, but he was not done showing off. Still firm enough to stay within her, he knelt enough to pull her against himself, then managed to stand. He headed right for the master shower.

Despite his initial determination not to get affectionate with her, he ended up combing her hair while she just stared at him in the mirror. She had not said a word since he had finished undressing her.

"Sean," she finally said, "none of the party men could do anything like that. Certainly not your father. Where... ?" In the mirror, she saw the negative expression on his face and stopped in mid-question.

"I only have one question, Celeste; can you act natural around me from now on?"

"Natural? Hell! How will I keep from raping you?"

"Why don't you try raping your husband?"

"I..."

"This is not something that we will be repeating, Celeste. He should be the one who satisfies you. Either wake him up or get rid of him."

That threw her into another silence. "Have you and Tracey had sex?"

He thought he suppressed the flash of irritation he felt. Turning the question around, he asked her "If I go and have sex with Tracey tonight, are you worried that she will catch something that you gave me?"

Her face paled and she gasped. "I ... I really have been careful, Sean." In a very thoughtful voice, she added "I guess if you did it with Tracey, it would be more gentle and loving, wouldn't it?"

"Why don't you talk to Tracey about what she has and hasn't done? She wants a good relationship with you, you know. Why don't you talk frankly about you and your husband, too."

She gave a little laugh "There's no point in considering anything private with her, is there?"

"Maybe you can use it to get closer," he suggested.

"Are you ... are you sure we can never do that again?" she begged.

"No, Celeste. You really caught me by surprise. I had no intention of having sex with you. I will say that you should have no trouble getting your husband interested again if you put your mind to it."


Carole was concerned when Sean asked for the whole Gang to be there before he talked about Celeste. "I feel like I betrayed all of you," he said with obvious regret. He described exactly what had happened in great detail. "I should have pushed her off as soon as I knew what she was doing."

Perhaps feeling responsible for his earlier trysts with Rebecca, Nancy spoke up. "We know that unexpected things can happen, Sean. It's my guess that you did accomplish the main objective." There were murmurs of agreement from the others.

"I would not be surprised if there were a couple of other benefits," Phyllis added. "With luck, Celeste's relationships with both her husband and her daughter could improve. That will help Tracey, and she is our project, after all."

Carole came and sat on his lap, telling him "I guess with the kind of atmosphere we have, we can't be surprised at what happened. You didn't betray us. I just think that we have a long-term problem keeping a lot of needy women from coming after our lover." The others echoed her sentiment.

He was a little concerned when they asked him to let them talk by themselves, but they assured him that it was nothing bad.

As soon as he had left, Claire took the lead. "Tracey is my 'doll', and I say that she needs Sean to make love to her. With what she is thrown into at home, it has to be killing her not to fully understand things."

"Is she protected?"

"Yes, for quite a while."

"Wouldn't we just be forcing Tracey and Sean into being a couple, even if they are not ready for that level of commitment?"

Julie answered that. "I honestly think Sarah should have sex with Sean before she goes to college."

"What does Dan have to say about that?"

"Dan is listening to me far more than he ever did when he was growing up," Julie quipped. "He will let Sarah decide."

"Has Sarah mentioned the idea to you, Julie?"

"She has asked me if I thought she should."

"And you told her... ?"

"When in doubt, don't."


Claire vehemently denied encouraging Tracey, and Sean found no reason to doubt her. That did not diminish the problem he was presented with. To her credit, Tracey seemed to know exactly what was worrying Sean. After practice, it was Tracey who was waiting for him.

"Get in, Sean, we're going to my house." Sean sensed that something unusual was afoot, but he did not press her. They talked about school things until Tracey drove into an empty garage. At his questioning look, she told him. "Mom has the kids with her. They won't be back until late. Dad's out of town again."

It did not take Sean's exceptional experience with women to figure out what Tracey wanted. Nor was the prospect in any way displeasing, except...

Hands shaking, Tracey started undoing Sean's jeans as she said "This doesn't mean we're going steady, or that we're even boyfriend and girlfriend. I just can't stand being so clueless any more, especially after you had sex with Mom."

"You mean..."

"Yeah, she told me. Oh, Sean, it's ... it's..." Obviously, she had just uncovered his already rigid cock.

There were a lot of things Sean wanted to say in response, but he had learned enough to know when no amount of talking would change what was about to happen. Besides, Tracey was right up there with Sarah in his affections. He was proud of how much she had changed herself, and if she was determined, he wanted it to be a good experience for her.

Pushing off his own shoes, shorts, and jeans quickly, he reached for the snap of her jeans and returned the favor. As he pulled them down, though, he sank to his knees. "Put your hands on my shoulders," he ordered, then helped her step out of her jeans. "I always wondered if you could really take these off or if they had to be surgically removed," he joked.

It was the perfect mood lightener, as she slapped his shoulder and giggled. She become serious and tense again when he grasped the sides of her panties and started to ease them down. "Am I the first guy to see this?" he asked gently, looking up at her face. She could only nod, and he told her "Thank you so much for the privilege."

Sean debated using his mouth on her right then, but decided to take things a little more slowly. As he stood up, they were both naked below the waist, but had their shirts on. Tossing his own off quickly, he grasped hers to lift it off. She was staring at his cock so hard that she raised her arms puppet-like. When her eyes were uncovered again, she stared at him, her lower lip quivering slightly. He held her gaze as he undid her front-clasp bra.

Belatedly, he noticed how sexy her bra was, and remembered that the panties had matched. "Oh, Tracey! You put these on especially for me, didn't you? And I didn't take time to appreciate you in them." With his hands on her upper arms, he held her back and openly ogled every inch. "On the other hand, I certainly appreciate you like this!"

Naked with Sean had been a central fantasy of Tracey's since she first noticed his new body. Now, she was living that fantasy. Why was she so tongue-tie, so unable to say or do anything?

Strangely enough, Sean was not feeling terribly confident, either. Unlike with Sarah, Tracey had been in his pubescent fantasies. Even with all of his experience with the women, realization of a long-held dream impacted him, as well.

Sean knew, though, that it was up to him to try to make up for all that Tracey had missed. He did not view her as the love of his life. He did admire her, though, for the way she had changed herself over the past months. On top of that, her already appealing body had been enhanced by the exercise program that Claire had gotten her into.

"Let's shower together, Tracey. For what I'd like to do, we need to be squeaky clean."

In contrast to his experience with Sarah, Tracey was ready and eager for everything. His body was like a treasure to her, and she unabashedly worshiped it. Her response to every touch from him seemed amplified. It was the kind of response that most males can only dream of eliciting.

After three hours, Tracey warned him that this had not been a one-time need. He certainly was not dreading a repeat.


During the wrestling season, Sean ended up at home a bit more, although he had a steady demand for remodeling work. He still spent as much time as possible with the women and with Tracey, but he had to be careful not to trigger a backlash from home.

More and more since the first wrestling match they attended, Melanie took the initiative to make conversation with him. Sean did not enjoy that, at least at first, when she tried to take a more authoritarian attitude. With help from the women, he found ways to discourage her from the more 'motherly' threads and after a few weeks, they were talking much more as equals. Sean could not say that he enjoyed that, but it did feel good to have gained some more control over his home situation.

For a few days, Sean had been noticing that Melanie was suffering some pretty severe discomfort in her back and he told the women about it. "Give her some massages," Claire said immediately, and the others agreed.

"I don't want that kind of closeness! I don't really want to touch her," he objected.

"Sweetie, this is not news to you, but she will be your mother for the rest of your life. You may never love her and you may never even like her, but she will still be your mother. That will require some kinds of interaction."

Claire continued. "You have done a great job of establishing control of the conversations. Here is another chance to gain even more control. She has sexual feelings for you and they seem to be strengthening, so..."

"But why would I want to encourage those feelings?" Sean interrupted.

"As I was about to say," Claire said with a chuckle, "use those feelings to increase control of how she treats you, how she acts around you. Here's my thought: offer to massage her, but set some conditions. I'll bet she'll go along with them."

The very next evening, Sean and his mother were alone for dinner, with his father out of town. Her back problem seemed to be bothering her even more, so he went for it. "Mother, I've gotten pretty good at massage. Let me see if I can help your back."

"M ... massage? You?"

"Sure. Come on. Let me show you." The women had pounded on him how important the next move was. He took her hand to lead her to the master suite. It was more contact than they had had in a long time, and he had initiated it. She was completely disoriented, as the women had anticipated, and put up no objection as she followed him.

When they had found a large towel and laid it out on the foot of the bed, he instructed her "You'd better go to the bathroom because you will probably fall asleep after I'm done. I'll wait outside the bedroom until you call me. Lie with your head right at the foot of the bed. Get as naked as you feel comfortable with. The less clothes, the better the massage. I'm sure you've had massages before. OK?" With that he left the room.

He heard the bathroom sounds and then just minimal noises of moving around. He wondered if she was deciding how much to undress. Finally, she called that she was ready.

She had on a fairly modest bikini that he had seen her in - a clever decision all around. As he walked up to the bed, he told her "If this works, I'll get some massage oil. That always feels good."

Working around the tiny strap of the bikini top, he went right to work. It did not take him long to find some very tight spots, a couple of them actually warm to the touch. At first, his efforts to loosen those places hurt her, but he kept up a persistent pressure until he could feel them ease up.

Her back was not at all like those of the older women. She was not overweight, but there was not the tautness and muscle tone that he was used to. Phyllis had told him that he should work the looser flesh in a very possessive way, to the enthusiastic agreement of the others.

"But won't that irritate her?"

"And... ?" Phyllis quipped. "I thought you would like that. Actually, just the opposite will happen. It will arouse her."

"Why do I want to arouse her?"

"Control, Honey. Control. You promised that you would not try to make her your slave, but you can accomplish the same thing in a more subtle way. Make it so she is desperate to please you."

"But I don't want to feel responsible for her."

"Too late. When you showed her the pictures and laid down the law, you took control - you became responsible."

"Maybe I should have thought more about those pictures," he said.

"Don't ever even think that!" Carole ordered. "Look at your life now versus then. Having to parent your mother is a small price to pay."

"You're right. You're right. I would never want to go back. I would never want to lose all of you." That ended the discussion with some very affectionate contact.

When he began grasping handfuls of flesh and moving it around almost playfully, Melanie at first gasped. Before long, though, the gasps turned to irregular breathing, followed by some writhing of her hips. That was a signal he had been told to watch for, and he stopped 'playing' with her back.

The massage ended with some long, firm strokes before he covered her with another large towel and left.

Sean's studying for the night was done and he was snacking in the kitchen when Melanie came out of the master suite. She looked sleepy, a little disheveled, and more than a little confused. She wore a light robe and he had the sense that was all she wore.

"Feel any better?"

"Y ... yes, I do. Where did you learn that, anyway?"

"Oh, here and there. In wrestling, you get lots of pulls and strains, so massage is important." With her increasing awareness of her son, Melanie understood that she was not supposed to probe any farther.

"I'm going to take a bath and go to bed early tonight."


With his father still out of town, Sean was not surprised when the next evening, Melanie asked him "Any chance I could get another massage, Honey? It really helped last night." He was barely able to avoid a reaction at the affectionate term.

"Sure," he answered with much more enthusiasm than he felt. "I got some oil today, just in case. Call when you're ready. I can hear you from right here."

It surprised and somewhat dismayed Sean when he walked into the master bedroom and sprang a hardon. Melanie was in position, but she had skipped the top and wore a thong bottom. He could not tell if it was a swimsuit bottom or a thong panty. The effect of being naked was the same.

He absolutely could not allow his mother to sense any reaction on his part, although if she happened to look up and see the bulge in his pants, she would know she had succeeded. He was sure that she was determined to get a reponse from him.

Part of him wanted to do something to try and shock her as she was obviously trying to shock him. While he was rubbing oil on her back, though, he took time to think about it and decided that he should not enter that game. The first time, he had stroked right down to the top of her suit bottom. He allowed himself to move the stroke boundary right down to the tiny string that encircled her hips.

He did increase the amount of 'playing' he did with her flesh. That is, he did it until she let out a very soft little moan. Making sure he did not stop abruptly, he resumed normal massage strokes shortly thereafter.

When he finished, he decided to try putting a little pressure on her. "I'll turn around so you can grab a robe or just get to the bathtub. You need to get the oil off of you. When you're gone, I'll pick up the oil and the towels." He did not give her the chance to fall asleep as he had done the night before.


"Are you sure you want to play this game?" Phyllis asked him. She met Sean at Carole's after school the next day. "Unless you can honestly say that your feelings about her are changing, I would advise you to back off."

"I can't see that there can be much more to the game," he opined.

"Sean, Sean," Carole cautioned. "She has only begun. When she wore a bottom whose top was farther down her ass, you stroked right to that limit. What will you do if she's naked the next time?"

"She wouldn't do that!"

"She absolutely WILL do that," Phyllis chimed in.

"How can you know that she will?"

"Because it's what I would do if I wanted your attention and I had that chance," Carole interjected. "Look at it from her standpoint, Hon. She now realizes that she has completely failed in any mother-son relationship. Between some guilt over that failure and some lust after your bod, she is now in seduction mode."

"Seduction? She wouldn't have sex with me!"

"Oh, it might not go that far. If she can at least get you to the point where you obviously want to have sex with her, she will have achieved at least some of her objective."

"You really think that is what's going on?"

"Absolutely," the two women said almost in unison.

"Wow! So what do I do?"

"That depends on how you feel about her," Carole offered.

"You know how I feel about her."

"But we sense that those feelings have changed a lot," Phyllis told him.

He thought for a moment, then nodded his head rather sadly. "I guess she is no longer the enemy - the monster that I had to constantly fight against. She's more just another attractive older woman."

"So, you have really forgotten all of the hurts from before?" Carole challenged.

"Forgotten? No, I don't think I will ever forget. It's just that my life is so great right now. I don't feel any more anger or need for revenge. You know, living at home has gotten to be pretty easy."

"That's great to hear, Sean. Too bad more adults can't 'roll with the punches' like that and look forward." As Phyllis hugged him to emphasize her words, she lightened the mood with "I really wish you were still naked all the time. Hugs were even better back then."

"When am I on your schedule next?" he shot back. They all laughed a little before he said "I still don't know what to do."

"I predict that tomorrow night she will be naked on the bed. If you massage all the way down her ass, that will tell her that she should do even more to seduce you. If you stop at around her swimsuit top, she MAY give up the game. I wouldn't bet on that, though," Carole declared.

Phyllis added "If that doesn't sound like much advice, it's because it's really up to you. If you proceed, she will next ask you to do her legs. After that, she will roll over on her back. Before rolling over, though, she will probably find some reason to walk to the bed naked after you're already in the room. Or maybe she'll 'forget' something and have to get up to take care of it. She'll even 'forget' that you're in the room and will see her naked."

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