Gang of Five
Chapter 11

Copyright© 2009 by Shrink42

Romantic Sex Story: Chapter 11 - 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  

The next noon, Dan had another surprise. The women were all dressed. That did not stop them from undressing him or from bringing him to full erection.

Because he had a chart to follow, the workout went quickly. There was always one woman ready to adjust the machine for his next set.

When the workout was done, Claire and Nancy again led him to the shower. They wore only outer garments and they stripped and got in the shower with him once more. "We're going to get you off in here today, Stud. There won't be time for the real thing. Besides, we thought you should think about it a little longer."

With the little thought he was capable of, he mused that these women were very, very experienced at stimulating men. That led him to sadness that nothing like this happened in his marriage. He very nearly wilted, but the women were just too good at it.

The women donned their few clothes after they dried, then they all went upstairs. He was feeling relaxed from coming and was much less anxious than he had been the first day.

The relaxation ended instantly when he reached the main floor and came face to face with a younger women that he had never met. Claire was ready to keep him from recoiling backwards and Nancy moved to put her arm around the woman.

"Dan, this is my niece, Rebecca Sanders. She is a consulting psychologist who has worked with marriages for twelve years. She has agreed to help with your plan to try to bring your marriage to where you want it to be."

No amount of professional experience could keep Rebecca from blushing and staring. The sight of a good looking, well-built, nicely hung, naked man in the midst of the clothed older women was just too far outside her experience. Obviously by prior arrangement, the gang left Dan and Rebecca alone.

She was the pro and she knew it was up to her to end the mutual embarrassment. He clearly was not up to it. "Dan, it's a privilege to meet you," she said sincerely. "I am frankly amazed and hugely impressed by what you are willing to do. Seeing that much commitment to your marriage almost makes me cry. In my business, that is too rare."

Finally able to speak, he replied "You must know that I have had sex with these women. What kind of commitment is that?"

"Ah, well. We will need to address that guilt problem," she told him. "Can we sit and chat for a few minutes." They moved to some chairs where a towel was waiting for him to sit on.

"First of all, Dan, why am I here? As you can probably guess, this whole idea is so strange that I laughed in Aunt Nancy's face when she first asked me. The thing is that in my business, it's easy to get in a rut. I guess that's like any profession. The women's ideas are intriguing, and my professional curiosity got the best of me. I also could not ignore the sincerity with which the women wanted to help you.

"I have to ask you, Dan; how can you stand to do this? Isn't it terribly humiliating?"

"Dr. Sanders, in your..."

"Dan, please call me Rebecca. Yes, I am getting paid for this, but the situation is so ... intimate that first names seem right."

"Rebecca, in your practice, you must have encountered other men whose wives refused sex, haven't you?"

"More than you would guess."

"Well then, you have a good idea of what happens to our psyches. You might say that I live in constant humiliation. I'm not saying that it makes this easy, but if it can actually lead to fixing my marriage, what's a little humiliation?"

"What has been the hardest part of it all?"

"Well, coming up the stairs to see you is right up there. Having Mom see me, especially erect, was really tough at first, too."

"Is that easier, now?"

"You know, I always knew and just accepted that Mom loved me. I love her, too. Now, though, I'm finding out just how strong that love is. I'll probably never understand a mother's emotions, but I'm getting an education."

"Does your love for your daughter help you understand Julie better?"

"I should have assumed that the women would have told you everything," he chuckled. "I suspect that men can't really feel a mother's love. It just isn't the same."

Rebecca stared at him for a while. "If you understand that, Dan, I'm surprised that you haven't been more successful at fixing things already."

"Yeah, well, knowing and doing are two different things. I guess you heard that I did nothing while Arlene has been screwing up Sarah."

"I could go into a long discussion of roles in a marriage, but that's not our main concern, here," she stated. "I have to ask; doesn't it hurt your pride, your ego, to let these women manage things like this?"

"Well, it does, of course. The thing is, the night Mom hit me with the fact that Sarah was heading to be another Arlene, sexually, it was like a punch in the gut. She did it gently, but I was so ashamed for what I had not done for my daughter. I guess I kind of gave up at that point."

"The fact that you got some sexual release afterwards didn't hurt either, did it?" He just grinned in answer.

"I understand that was the first time you had cheated on your wife." She purposely used the provocative words.

"I hope you don't end up telling me the women were all wrong, Rebecca. Their theory is that if I come across as sexually confident, it will help to stimulate and arouse Arlene. They think I need to have lots of sex to accomplish that."

"Hmmmm. I can't say they are wrong. It's just so ... unique," she mused.

"OK. I have done it with the four women. Should I continue?" he asked.

"Will you hold off for a few days while I observe?" she came back.

"How do you mean 'observe'?"

"What I think I need to do to accomplish what the women hired me for is this: I need to see everything that goes on. One of my tasks will be to suggest to you ways to change your behavior that will make you seem more confident, more sophisticated. In other words, more virile. If you think this is embarrassing to have me seeing you like this ... can you handle it?"

"With what I have already done, I should be able to," he said without much confidence.

"But these are all older women, your mother's contemporaries. I'm in your generation. I'm a potential mate, in the strictest sense. Will your ego let me in on some extremely intimate things?"

"I decided to go ahead with this, and I'm not going to back out. I can do it."

"Prove it," she challenged.

When he just sat and stared at her, she went on in a softer tone. "Look, Dan, from a sexual standpoint, what is your current persona? I would say that sexually, your identity is as Arlene's husband.

"Now, that is just fine, given that Arlene could primarily be identified sexually as your wife. As you too well know, she is not your wife sexually in the accepted way. Do I make sense?"

"Unfortunately, yes," he admitted glumly.

"The way the women have decided to correct that imbalance is intriguing, and I cannot say that I disagree with it. They want to break you out of your role as Arlene's husband and establish you as a sort of herd bull. You will belong to no woman. In fact, all of 'your' women will belong to you.

"Of course, in the end, you want only one woman to belong to you. Actually, we should consider whether it might be good to have your daughter in your 'herd', as well - not full sexual partners, of course.

"So, what am I saying with all of this? When you meet a woman, you should think 'I am going to give you the privilege of being with a dominant stud. Look what I can use to make you scream in ecstasy'. Does that tell you what I mean by 'Prove it'?"

Once again staring at Rebecca for a while first, Dan stood and began stroking his penis. She let him continue for maybe twenty seconds, the demanded "Dan, why are you doing that?"

"Huh?" he snapped rather angrily, "I thought that's what you wanted me to do."

"If that's what you thought, then you shouldn't be doing it. You should be thinking that you want to give me the privilege of seeing your cock at it's finest. You should be thinking you want to get my panties wet with desire to have that cock in me. Now, think those thoughts and get my panties wet!"

That, of course, did nothing to increase Dan's arousal and he almost felt like stomping from the room in a show of anger. He had committed, though, and this cheeky woman was part of that commitment. Taking a deep breath, he thought about her panties. She was quite attractive, and her business-like pant suit showed a nicely rounded ass and an admirably flat tummy. He could not tell if her thighs were firm or fleshy, but he guessed that they were quite nice. She was sitting rather primly, with her legs together. Being more than a little upset with the way she had talked to him, he decided to strike back a bit.

"Rebecca, please open your legs so I can see when the damp spot starts," he said in as commanding a voice as he could manage. Watching first the shocked look on her face and then the flush, he felt both satisfaction and an increase in the flow of blood to his cock.

"The crotch of your pants is nice and tight against your pussy lips, so I should be able to see a little swelling, too," he added. When she started to move to lessen the pressure, he chided "No, no! Leave it like that. I need to see how I am doing. Open your jacket a little, please, so I can see when your nipples pop out."

That brought a gasp from her, but she slowly complied. "Ah, I see they're already hard," he said with a grin.

His motivation had been to erase the implied insult to his manhood, and that seemed to be working. Now, though, his stroking felt so good that he wanted to continue. Despite the fairly long time that it took him to come during intercourse, right from puberty he had been able to make himself come rather quickly with his hand.

Maybe it was the shortage of blood to his brain that made him think he was in a contest with Rebecca. She had escalated things, but he would out-escalate her. It was not until he was almost coming that he worried about the poor impression he would make with just a few spurts. After all, he had just come from the shower where the women had gotten him off.

Another thing he had not considered was getting semen all over the carpet in the room. There was a glass-topped table in front of Rebecca's chair and he walked to it as sedately as he could manage while continuing the stroking.

His attention was mostly on his cock and the feelings radiating from it, but he saw her close to saying something when she realized what was about to happen. She just worked her mouth silently, though, then watched as he shot a surprisingly strong three spurts onto the table top.

It had taken a lot of bravado to do that, but when he finished, there was neither bravado nor strength left. He staggered back to the towel he had been sitting on and laid his head back on the chair.

There was only the dual sounds of their heavy breathing for quite a while before Dan breathed out "Go ahead if you want."

"Huh? Go ahead what?" she asked.

"Go ahead and get yourself off. I'm sure you want to after seeing that."


Rebecca had to call upon all of her professionalism to show up at Claire's the next noon. Of course, she had not done herself after Dan's challenge the day before. She had made it through lunch without revealing her inner turmoil - except to her aunt.

She was there before Dan, which was important. For the next few sessions, she would be looking for attitudes or responses of his that she thought needed modification.

As soon as he arrived, Rebecca saw something that needed correction. She waited until he was about to start his workout before mentioning it to him, though. She asked to be alone with him for a moment, and asked him "What are you thinking when the women undress you and stimulate you?"

"Well, I know they really want to help, so I am willing to, uh, humor them."

"Wrong attitude, Dan! You are graciously granting them the privilege of looking at your naked body and your erect cock. Undressing you is an appreciated service that they are performing for you. Do you see the big difference?"

"That is quite a difference. I'm afraid that I don't feel that kind of, uh, arrogance. I just don't have the attitude you described."

"You definitely do not, and you need to change that. Don't just tolerate them doing things to you. Allow them to do things for you. Stripping and arousing you is not for their pleasure, it's primarily for yours."

"How do I change how I feel?"

"First of all, think of how you should feel, and why it is important that you acquire those feelings."

"You gonna adjust my weights for me today?" he asked suddenly. He could not resist the urge to try to get back at her. This time, she noticed it and was pleased.


Brunch the Sunday after Sean's coup was lively. Claire, and rather surprisingly, Nancy, were agitating strongly to include Sean in the group's 'stable'. While not begging quite as loudly, Julie was also interested.

Phyllis provided the cautionary voice. "Remember, girls, we are all the age of his grandmothers. First of all, would he want to have sex with any of us? Secondly, what would be the best initiation and training for him?"

Julie took up the cause for the horny ones. "I'm afraid you're thinking in 1950s high school terms, Phyllis. What I see is a young man with whom we have all become close friends. Do any of you think that taking him to bed would ruin your friendship with him? Do you actually think he would be repulsed or disgusted by any of our bodies? Do you think it would warp his sexual appetite for the rest of his life? Look what has been happening with the massages."

"Julie, it could affect his preferences in women," Carole warned. "You make excellent points, though. We have all worked to help him in a number of ways. Wouldn't this be one more important way?

"Personally, I am honored and thrilled that he seems to accept my body and be excited by it. Remember, his own attractive mother's body left him totally cold. What does that say about him?"

"I think," Phyllis answered, "that it says he is a guy who is concerned with more than just physical beauty. I admit that is a very good thing. Look, I want him as badly as the rest of you. I just don't want us to erase the progress we have helped him make by going too far."

Carole went on. "I appreciate how all of you have stuck with our gradual approach with him. I think that has been the right approach, but I agree that he is ready for the ultimate step."

"Ill bet you've all noticed that the four guys are looking rather worn out these days," Claire observed. "I know I am almost as horny as when I was a teen since my first time in the hot tub with Sean. The dancing, and then the massages..."

"Well, I still think Sean is the right guy to help Sarah catch up with other girls her age," Julie added. "So besides wanting him in my bed like the rest of you, I want him better able to be a good influence on her."


Sean told his parents that he was spending Saturday and Sunday nights with a friend. When his father was out of the room, he warned her not to ask who the friend was. Carole had not told him the complete reason, but just from what had been happening because of the massages, he was very excited about it.

After a quick trip to the hot tub and a rinse in the shower together, Carole told him "That first night when you slept with me, it took everything I had to resist making love to you. If it hadn't been for the pain in my ankle, I would have failed. I don't have to resist any more."

"You mean... ?"

"Yes, Honey. If you want to, that is. I know the first time is a big step for a young man. If you'd rather save it for a girl your age, I can understand that." He could see that her eyes belied her words, though.

He wrapped her in a hug and spoke softly into her ear. "There's no one in the world I would rather have be my first. More than anyone else, you're the one who has given me a new life."

Carole could only moan out the emotional impact of his words. Quivering and squeezing him for all she was worth, she finally managed to say "You know, you need to be with the other women, too."

"Need to? You make it sound like a chore. How can I be so lucky."

Not able to think of a response, she knelt in front of him and told him "We'd better take the edge off. You will be happier if you can last a minute or two your first time."

When she helped him stagger to the bed after his blowjob, he asked "Let me make you come, first."

"Not this first time, Sweetie. We're both too eager to delay any longer. I'm sure you will take care of me plenty of times."

All of the four men that the Gang regularly had sex with were in marvelous shape. The women would have it no other way. When Sean let himself down atop her, though, it was like welcoming a Greek God into her body. She could only keep her hands off of his muscles long enough to guide him in.

After several gasps and groans, she was able to say "When you make love to a young girl, she will be a lot tighter."

"But I won't love her like I love you." That was totally unfair of him, and his very first time ejaculating inside a vagina was because it was rippling and squeezing around his barely-moving cock in the midst of her intense orgasm.

Barely a minute later, they were both struggling for breath, and he was looking down at her in wonder and puzzlement. "God, Sean! I can't believe that! When you said you loved me, I went off before you hardly moved. That's ... that's ... I've never even heard of that. Can ... can you move back and forth? Are you too tender?"

Having come twice in a few minutes, he was indeed very tender. There was no way he would let her know that, though. They were able to make up for the suddenness if his first explosion with almost four minutes of stroking before he stiffened and let loose again. She did not come again.

She did not come again during that coupling, that is. They cuddled wearily for quite a while, then took another shower together. When they returned to bed, he insisted on taking care of her, and he was not satisfied with just once. He was not satisfied with twice, either.

When she was still too limp to help much after a real monster, he took charge. "I saw a picture on the Net where the man came in from behind while they were on their sides." That sounded wonderful, and he was still inside her, even though soft, when they awoke two hours later.


"You look like a newlywed, Hon," Claire said gently. The brunch was at Carole's and Sean had gone off to work for the morning and most of the afternoon.

"Maybe it's just my memory going, but I don't think my honeymoon was that good," Carole admitted.

"So, he's learned pretty well?"

"Oh, the men know more things. It's just the feelings..."

"Be careful about falling in love with him. When he eventually finds a girl, you could get hurt," Phyllis counseled.

"Yeah, well, that's not exactly something I can control," Carole declared. "I'm OK. I can genuinely rejoice for Nancy when she has him tonight - and the rest of you, too. I'm not going to fight the feelings, but it won't kill me when it all ends."

 
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