Gang of Five
Chapter 8

Copyright© 2009 by Shrink42

Romantic Sex Story: Chapter 8 - 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 tech from the security company renting the cameras was uncomfortable having Sean present for the demonstration and instruction session. Nancy was persuasive, though. She had insisted that Carole also be present.

"The cameras are single focus. They have wide angle lenses and a perfect depth of field for shooting in a room. The transmission range to the receiver is limited to one hundred feet, and is best under sixty feet.

"We have a version of the camera with its own fake hardcover book. The lens is right in some embossed writing on the spine. That's a very popular one. We have one that can be put in a cold air return. A little box that holds drink coasters works well. Others can just be stuck in any place that has a good view, but is unlikely to be noticed. For instance, under the low edge of a table, or inside an entertainment cabinet with a glass door. I have here a long list of placement possibilities. We suggest that the locations be selected well before the units are needed.

"There is one other important feature. The receiving station can send a turn on signal to the cameras, and the receiver itself can be signaled remotely. That means you can start the whole system from outside the house when there is actually something to shoot."

The session lasted for almost two hours. Even though the party was perhaps six or eight weeks off, it was very instructive and got Sean and the women quite excited.


Incredibly, it took until the third week of Sean's 'new life' before Melanie questioned her son's changed schedule. In the interim, Sean had worked at each of the women's houses. Carole no longer accompanied him to the other houses, but that did not stop the hot tub sessions that ended each visit.

It was at dinner again, really the only time there was any significant communication in the house. "Sean, haven't you been going to bed awfully early lately. Are you feeling all right?"

"Well, I've been getting up very early to work out," he answered. Once again, his possible responses had been discussed thoroughly beforehand.

"Work out? But you always worked out. What has changed?"

"I am determined to win a number one spot on the team next year. That's going to take a lot more work than what I have been doing."

"Number one spot?" Melanie understood nothing about his sport. He went on to briefly explain the team structure and the seeding for matches.

"Oh. I thought maybe you would be through with wrestling. It's so ... so..."

"I'm sorry if it's too macho for you, Mother, but I enjoy the one-on-one struggle. It's a great feeling when you overcome your opponent." That wording was crafted to both shut her up and to impress his father.

The Gang had concluded that Melanie could not object to anything that was manly. They also surmised that Bert could be brought into play as an ally by playing on his competitive streak. They were honestly surprised at how she had caved in to her husband previously.

"But what if your studies suffer?" Melanie had found another wedge, she thought.

"Maybe you haven't noticed, but that's all I do after dinner. I've got a lock on one 'B' and the rest 'A'. That won't change."

"Why not all 'A's?"

"Teacher conflict." He said it in a voice designed to signal the end of discussion. It was a totally new move for him, and he was both astonished and delighted when she said no more. He had expected an argument about all of the time spent working after school.


"Well, Gang, one of Sean's biggest nights is a week from Friday. We need to strategize on our final preparations for him." It was a Sunday brunch in late April and Carole was talking about the major all-school dance in the first week of May.

"I think his dancing will be fine," Claire opined. "I doubt there will be any high school boys better than him."

"Oh, I'm not concerned about his dancing," Carole said. "With you for a teacher, that was never a worry. Even with everything that has happened, this first dance will be a huge step for him. First of all, he still has had minimal interaction with girls his age. Now, being naked around us has certainly helped. I'm sure he realizes that it is helping. Haven't you been amazed that he will just undress when we ask him to? What does that say about how much he wants things to change.

"Another problem is that even after discovering his parents' probable swinging, he can't shake some guilt about 'sneaking off' to the dance."

"I assume you have a plan for getting him past these problems," Nancy prompted.

"Of course," Carole agreed. "Monday thru Thursday afternoons next week and hopefully into the evenings will be final rehearsals for Sean's big debut. I am hoping that he can get out of dinner at home at least some of those evenings."

"I guess no lawn work will be done next week, then," Julie said.

"He'll work his tail off the two weekends. Our yards will survive. This is a bigger issue," Carole said firmly.

"OK, Monday afternoon, we will all be here and we will act like it is a high school dance. He will have to approach us, ask us to dance, do everything just like at the real event."

"Uh, Carole, will he be dressed?"

"Of course not," Carole said firmly. "The principle is still that if he can do it naked, he will so relaxed and confident clothed that he will make the best impression.

"Now, Tuesday will be a rerun of Monday, except that we will be naked, too."

"Carole! Don't you think that's taking things too far?" Nancy asked in shock.

"Hell, no!" Claire jumped in. "I've been wanting to ever since the first lesson.

"Come on, Nancy, it will be good fun," Phyllis cajoled.

"Well, I can't be the wet blanket, I guess," Nancy conceded. "How are we going to set this up. We should make it a big surprise."

"Oh, it will be a surprise, all right," Carole assure them with a grin. "It will not be the biggest surprise of the week, though."

"Oh, I love the sound of that," Claire chortled. "Give! Give!"

"Patience, Grasshopper," Carole quipped. "I want to bring a few girls from Lindsey's over to dance with him Wednesday and Thursday afternoons."

"Carole! I thought you had something really juicy planned," Claire pouted.

"Well, yes, I do. The Lindsey's girls are used to being around naked boys with hardons."

Carole felt a real sense of triumph at the gaping silence from her four friends as the full import of her idea sank in. When it was Claire who exclaimed "Oh, my God!", it was like winning the lottery. Not very often was anyone able to shock Claire.

"Carole, that's ... that's ... how would you ever get him to go along with that?" Julie stammered.

"Wait. There's more. I think I can arrange it so at least one of the girls will be from his school."

"Are you purposely trying to drive him away?" Nancy asked, incredulous.

"No, I am trying to make going to his first dance seem trivial. I admit, I will be pushing his trust to the very limit, but I think he needs something this strong. Remember, it won't be that long before his big confrontation with his mother. I think we can all see that he is not ready for that, yet."

"I thing Carole is right on, here," Phyllis offered. "Dancing naked with those girls, knowing that he will be seeing at least one of them at school and maybe at the dance ... that will be one of the hardest things Sean will do in his life. I believe he will do it if Carole asks him to. I believe that after the dance, he will approach everything differently. He will be more ready for battle with his mother, the lawn care business will seem less daunting, and he will feel like he can handle any wrestling opponent."

"Thanks, Phyllis. That is exactly what I've been thinking. I need an opionion, and I need permission," Carole said. "First of all, should we tell him beforehand what is in store, or just let him handle it day by day?"

It was Nancy who answered quickly "I know that for me, it was better not to have to worry about things ahead of time. Besides, it will help him learn to react to things as they happen." The others murmured agreement.

"That's what I hoped you would think," Carole said. "Before I tell him about the girls on Wednesday night, I want your permission to get in the shower with him and get him off."

"Do it twice and he'll agree to anything," Claire quipped. "I think we have already agreed that Carole gets the first shot at any escalation, right?"

"I doubt that will buy him thirty seconds of softness when he meets the girls," Phyllis chuckled. "It should reduce his anxiety level, though."

"Will ... will the girls be naked on Thursday?" Nancy asked.

"Oh, no," Carole answered quickly. "I wouldn't ask them to do that. Besides, we've talked about how the impact is greater if he is the only one naked."


"Rebecca, I apologize for interrupting your Sunday." Carole had called Rebecca Sanders as soon as she returned from brunch.

"Carole, I told you to call any time, and I meant it. If I can't talk, I will let you know. You women are a real bright spot for me. I never know what you will come up with next."

"Well, hold on, then," Carole chuckled, "I think you will like this." She explained the plan for the next week, and it took Rebecca quite a while before she could respond.

"I could ask you to repeat that, but I probably wouldn't believe it the second time, either. You are unbelievable! How can you expect the boy to go along with that?"

"Tell you what, Rebecca. When could you come out and spend some time with Sean? Double clock."

"Oh, my regular rates are exhorbitant enough," Rebecca joked. "Whatever I had planned with the family today just got terribly boring. When can Sean be there."

"I'll call you back. Oh, I'd like to invite your aunt, too."

It took a half dozen phone calls to alert the rest of the gang and arrange for Nancy and Sean to be there, but Carole was finally able to tell Rebecca to arrive at four.

Sean and Nancy were at Carole's at 3:30, and as soon as he had undressed and showered, Carole sat him down for a chat.

"Sean, Honey, I am going to be pushing your trust in me quite a bit the next couple of weeks, starting in a little while. Nancy's niece, Rebecca, is a Ph.D. psychologist and a very successful family counsellor. She has helped us with a number of things. What you are doing fascinates her, and she would like to learn as much as she can. We think that she could ask you some things that we have not thought of that might help you, too.

"Rebecca will be here in about ten minutes. We want you to stay naked, meet her at the door, and try to act as natural as you can while she is here. Of course, you will be hard some of the time, but I think you know by now that that does not insult us women."

"God, Carole, I..." Sean started to say. Uncharacteristically, Carole put a finger over his lips to stop him.

"Sean, this is the first woman other than the Gang to see you naked. Please, just do this because I ask you. Rebecca is an absolutely delightful person and so intelligent it is scary. Concentrate on those things and not your gorgeous, exposed cock."

Sean's expression went through shock, fear, just a little anger, resignation, and finally, adoration. He put his arm around Carole and kissed her on the cheek. "I'm scared to death, Carole, but how can I not do what you ask? You and your friends are changing my life so much I can hardly believe it."

Carole impulsively grabbed him in a big hug. "Just remember, Sean, if you do the most difficult things in a controlled way, everything else will seem easier whenever it happens."

"You said the 'first woman'. Does that mean there will be more women stopping by?"

Carole was so surprised by that question that it showed. She threw a quick glance at Nancy before she could neutralize her expression. Sean caught it and saw Nancy's quick blush. "I guess you'll let me know when you think I need to, right? Probably best I don't have time to worry about it."

After that, Carole and Nancy openly gaped at each other before jointly engulfing Sean in hugs.

"Now, remember Sean," Carole said, still holding onto him, "you are a gorgeous physical specimen with a beautiful cock. It is a privilege for Dr. Sanders to see you in all your glory. Just keep reminding yourself of that."

"Maybe I'll get to that someday," he said. "Right now, the best I can do is try not to think about being naked."

When the doorbell rang, Sean got to his feet and started for the door. Before he got there, though, he stopped and said "Uh, if this doesn't happen to be Dr. Sanders, or if she brought one of her kids, or something, it could be trouble for us, couldn't it?"

"Damn! You're right, Sean," Carole exclaimed. "Wait a second. I can see from over here. I really want to shock her if we can."

"She doesn't know... ?"

"Nope. I can see that it's just her. Have fun with it."

"I'm more worried about surviving it."

As he swung the door open, Sean stood back far enough so he did not think he was visible from the street. He was certainly visible to Rebecca, though. She gasped, blushed, then started laughing,

"Your aunt and the Gang love surprises, Dr. Sanders," Sean was able to say as he fought to keep his legs supporting himself.

Rebecca forced herself to look only at Sean's face as she held out her hand. "I think under the circumstances, 'Rebecca' is more appropriate. Carole did not tell me that I would be part of your confidence building program. Since I am privileged to help, let me get a really good look at you."

As Rebecca started to walk around him, Sean could not restrain a gasp. Nancy joined him, but Carole was almost bouncing with delight at the way Rebecca had adjusted to the situation.

"Aunt Nancy told me that you were really built, Sean, but I had no idea," Rebecca enthused.

"Wait until you see him before school starts next fall," Carole said. "He is working out so hard it is unbelievable. You are looking at next year's state wrestling champ. We just don't know what weight class, yet."

"I can't wait," Rebecca said. "Can I see him just like this?" By this time, she had gotten back in front of him. "Aunt Nancy, you never told me what a gorgeous cock Sean has. I'm sure you must have seen it many times. No fair keeping it a secret."

Sean had been hard from the time he got up to open the door. Now, however, his glans darkened and his shaft got even more rigid and began bouncing a little with his pulse.

"Oooh. I need to use your bathroom," Rebecca said suddenly, aware that Sean was nearing the critical point. While Nancy showed her niece where the powder room was, Carole told Sean "Go in my bathroom and jerk off a couple of times." With a kiss on the cheek, she added "She played dirty. Honest, I didn't tell her to do that. You did great." A come or two sounded like a great idea to him right then, so he hurried off.

Rebecca was back well before Sean. "That was mean, Carole. Mean to Sean and mean to me."

"You made it meaner to Sean by yourself," Carole retorted. "I'm not doing this to be mean, Rebecca. He has some big events coming up in his life, and I just want him as ready as we can make him."

"Is the body talk OK?"

"Definitely OK," Carole answered. "It's all aimed at comfort and confidence."

"Then I'm going to really push it for a while when he comes out," Rebecca warned.

She was as good as her word. "Sean, have you noticed your penis being soft around the women more than when you first met Carole?" After discussing that, she asked "Do you need to do more total spurts per day to be comfortable than you used to?" Later, it was "Tell me how often and for what reasons you get hard at school. Compare now to before."

He had been almost flaccid when he came from the master bath. With Rebecca's questions, that did not last long. After about twenty minutes that must have seemed like hours to him, she came and got on her knees in front of him, taking his hands in hers. "Sean, I am so impressed! What I have done since I arrived is exactly what the Gang has been doing. I hit you with the most embarrassing things I could think of right away. From now on, everything should be easier to handle. Do you understand that strategy?"

Looking quickly at Carole, he answered "I guess I sort of figured that out. So far, it seems to be working. I just hope it doesn't get too much worse."

"And if it does, Sean? Will you just give up? Will you refuse to do what they ask any more?"

"No way, Rebecca. I've done too much to give up now. Besides, this is the first time I've ever hoped that things could be different."

"That's great, Sean. OK, let's talk about your mother, now."

"I thought you said it would get easier," he quipped, not really joking.

"I can already see that it will be easier on your penis," Rebecca said, noticing the sudden shrinkage. "That tells me a lot about your feelings toward her."

Rebecca's questions about his mother were very detailed and very intense. She asked about behavior, about what her body looked like, about how much of her body Sean had seen, and about how she treated Sean in specific situations. That discussion lasted nearly an hour before they broke for refreshments.

When they resumed, Rebecca asked him "Suppose you were naked in your room, just out of the shower. You had not closed the door, and your mother walked in. What would you do?"

Too startled to answer at first, he finally said "I'd turn away from her and cover up as fast as I could."

"Why?"

"Why? Well ... uh, she has no right to see my ... penis."

"OK. Let me give you a different perspective here, Sean. I think you are right about one reason your mother tries to control you so much. Preventing embarrassment and minimizing her involvement are definitely objectives.

 
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