Gang of Five - Cover

Gang of Five

Copyright© 2009 by Shrink42

Chapter 20

Romantic Sex Story: Chapter 20 - 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  

Julie had mis-calculated a little. She had not thought about possible tears spoiling Sarah's sparse but carefully applied makeup.

It was the first day of school, and Julie had worked very hard to organize a special sendoff. Arlene had been sent to the club early under the supervision of Pip. Literally everyone involved in Julie's project was there to see her off, and that made her cry. Fortunately, Claire was prepared. She followed Sarah's little car to a strip mall a few blocks from school. By that time the tears had stopped and Claire did the necessary patch up.

The long drive across town to school seemed to take forever. Sarah's confidence had grown immensely, but this was still a huge challenge for her. Having been worse than a nobody, an actual laughingstock, it was hard to believe that she would be viewed any differently.

Julie had managed to be there for the sendoff. With her usual uncanny sense of what was bothering the girl, she took her aside from the sendoff and asked "Do you really care any more what those other kids think of you? Would more nasty comments hurt you any more? I think you have grown way beyond that. How many of the girls who used to make fun of you could have done what you did? You can honestly feel like you are more confident, more mature, and better than them in many ways." Her beloved grandmother's words were what settled Sarah's nerves and allowed her to drive safely.

As she pulled into the student lot, it was very hard for her to concentrate on her driving. It seemed like every head, male and female, turned to look at her in puzzlement. She thought it must be the super-cute car. Julie had insisted that she put the top down, though. The hairdo that Claire had gotten for her could handle the wind just fine. Oh, and the sunglasses were awesome. Claire had sworn that she would be the best-dressed girl in school, and she believed it. Could it possibly be more than just the car that caught everyone's attention?

When she had parked and reached to open the door, Sarah automatically flashed back to the seemingly hundreds of times that Claire had made her practice exiting and entering the car.

"You have got to get it right," Claire insisted. "After seeing you drive in, everyone will be watching you. You want your exit to be so sexy, so sophisticated that all the girls' eye will pop and all the boys will get hardons." The thing that made those lessons so memorable was that Claire insisted that she practice naked. The only place was in the hot, closed garage. That was not easy to forget.

With her feet properly placed on the ground, she had to pause for a moment to look down at her legs and feet. Frankly, she still could not believe that they belonged to her. She had worked like a maniac to develop the muscles that seemed to have changed her calves from little girl sticks to sculpted women's legs overnight. The pedicure the day before seemed a little narcissistic to her, but the results - barely believable. And she could understand how some women collect so many shoes. The low-heeled sandals Claire had picked out for today were so elegant.

Sadly, one did not leave a convertible in a school parking lot with the top down in this day and age. Thus, getting the top up and secured and been another matter of much rehearsal. It had to be done gracefully, with nary an awkward move. She succeeded quite well.

With the car secured and what little she needed to bring for the first day in hand, Sarah was at the next point where she had to force herself to be the 'new Sarah'. Her previous mode of movement had been with arms generally folded across her front, often clutching books to her chest. Her gait had been something of a scurry. An onlooker would always understand that she had been trying to get as quickly as possible to where no one would notice her.

She and Claire had spent a whole afternoon looking at clips of women walking. Strutting, gliding, prancing, bouncing; there had been examples of all variants. In the end, Sarah had innocently made a major hit by telling Claire "I want to walk just like you. I'm built a little like you, and I love the way you move. I don't like the ones that look like they are just trying to be noticed. You look so graceful and natural. I'll bet you taught Grams, too."

Her transformation time at Julie's had been short but very, very intense, and many things had become natural. As she moved toward the school, most of the eyes that had been on her found it hard to look elsewhere. Only when she was surrounded by five of the Lindsey's kids just outside the entrance did she feel like she was no longer the center of attention and curiosity.

Much of her first day was spent trying to keep from being distracted by the reactions of people. She had vowed, honestly, that she would not forsake the friends that she had from previous years. She hoped that in some way she might be able to help them. Without exception, they were amazed upon first encountering her. With an almost constant escort from her Lindsey's friends, she use the opportunity to introduce her new friends to her older ones. Not surprisingly, the Lindsey's group went out of their way to befriend the few girls who had been close to Sarah before.

The encounter with her cousin Jess was a bit painful, however. Sarah impulsively threw her arms around Jess. Jess returned the embrace, but there was a little hesitation. When they pulled apart, Sarah could see pain and resignation in Jess's eyes. "I've missed you," Sarah said honestly.

"Me, too. I guess this is the only place we'll got to see each other. You ... you look so different."

"I'm so sorry our mothers are not speaking," Sarah said.

"What happened, anyway?" Jess wondered.

"Can I give you a ride home and we can talk? Well, maybe close to home would be better," Sarah suggested.

"A ride? You mean... ? Your mother would never let you drive."

"Jess, Mom is not in charge of things anymore. I'll try to explain. Later, OK?"

Sarah had selected AP classes with dim hopes of 'escaping' to college. Jess, while plenty intelligent, was not as aggressive. Thus, they would share only one class, plus having the same lunch shift. Jess spent their first shared lunch enthusing over Sarah's clothes and expressing her amazement that Sarah not only could drive, but had her own car.

Jess's reaction to the little convertible made Sarah feel bad. She certainly did not want to make her cousin feel any more deprived, but that was what seemed to be happening.

Taking all of the time Jess felt she could risk before reporting home, Sarah filled her in on what was happening at their house, all except Arlene's nudity.


Unbeknownst to Sarah, Julie had arranged for the Gang and Troy to be there when Sarah returned from school, as well. A little party was set up on the patio, and everyone got a chance to hear how her day had gone. Nobody mentioned her delayed return.

When things started to settle down a little, Claire gave out a piercing whistle, and when all was quite, Carole spoke.

"We're all proud of our own Cinderella, aren't we?" Cheering answered her. "I don't know many girls who could have gone through what she did, but her attitude and her determination were an inspiration for all of us, I'm sure." That brought enthusiastic cheers and applause.

After the congratulations and the hugs subsided, Sarah went around to the Gang and got them to agree to stay. Then, she sought out Troy.

"Troy, I hated to say 'no' when you asked me out on a date. I really like you and I want to go out with you. It's just that whenever we've been together, I've been naked. If we date, it won't be like that. It just seemed ... unequal, I guess.

"Here's the deal. If you strip right now and stay the evening, I'll go to the dance with you."

Looking around quickly at all of the women, Troy stammered "N ... now? Can't I wait until... ?"

"They are all staying for the evening. Look, Troy, you know all of them. They are not strangers to hard cocks, and I'm sure they have all been dying to see that great bod of yours bare. I don't want to seem mean, but I think you can understand my problem."

Talk about a test of desire! Despite Phyllis's warning when she 'recruited' him, Troy had indeed fallen in love with Sarah almost instantly. Phyllis! He would see her on campus frequently. How could he expose himself to her. Just then, Phyllis approached him and put an arm around him.

"We are in a body profession, Troy. The sooner you can get over your body shyness, the better it will be. I know this isn't exactly what Sarah had in mind, but this should help you decide."

With that, Phyllis shed her clothes right in front of him. While he was still in shock, she stepped up to him, loosened his pants, and pushed everything down to expose his rigid cock.

"There. The part you were most worried about is over. Sarah, give him some support so he doesn't fall over while I help him get this stuff off." After freeing his lower body, Phyllis helped him out of his shirt. Then, she took his face in both hands and kissed him. She had decided that a naked hug was more than he could handle right then, it least in front of everyone else.

Phyllis had planned ahead, and the rest of the Gang had gone in the house. "Sarah, give me and Troy a little time alone, OK?" As Sarah walked to the house, Phyllis led Troy into the pool. To Troy, she said "There are a couple of things I really need to talk to you about. First, though, I need to get you into a better mood for listening."

With that, Phyllis took his cock and balls in both hands and brought him off in near record time. He was so out of it that he did not even resist. Pulling him into a hug as he recovered, she asked him "Do you get pretty tender, or can I make you come again."

"G ... God, Phyllis! I ... how can ... Ohhhhh!" The last exclamation came as Phyllis decided to just proceed. As she stroked him, she led him to the side of the pool and helped him sit on the edge.

"There, this is a good way to talk," she declared as she stroked and fondled him in a more leisurely way.

"Troy, are you still a virgin?"

"Uh, yeah. You, uh, know about my family life and stuff."

"Well, I would be honored to introduce you to sex. I really like you and I am so impressed with how you have dealt with Sarah. Maybe you want to keep it for the right girl, I don't know. I can certainly respect that. Maybe you want your first time to be with someone your age. I can understand that, too.

"Let me warn you about something, Troy. I can tell that you have fallen hard for Sarah. Please, don't be thinking about her as your future wife. Oh, it could happen. I know she really likes you, too. But it is almost like Sarah has made a leap from twelve to eighteen years old. I suspect that she will not want to settle down with her first serious guy. Can you understand that?"

"Yeah, I've thought of that. She's like a butterfly, I guess."

"Exactly. The point is, if you think you're saving yourself for Sarah, it might never happen. If you decide you would like my help, Troy, please believe that it would be a wonderful privilege for me. Whatever happens, though, we will be working together some, and I look forward to that.

"So, if you know it isn't the first step toward marriage, how come you stripped so she would go to the dance with you?"

"Uh, I ... I didn't actually decide, you know," he stammered.

"See, I was right to get your cock out in the open. You need this kind of exposure, even if you weren't going to that dance. I always thought that some med school classes should be nude. Since doctors have to work with bare bodies all the time, they should be comfortable with their own nudity. We work with bodies, too."

"I guess I should be glad you're not setting the curriculum, then," he grumped.

"Good. You can joke about it. Troy, you must have seen the changes in Sarah, right? She is so at ease with her body, now. I'd like that kind of self-confidence for you. Never having to be concerned about your body lets you focus on task so much better. Are you ready for another come?"

Troy just groaned and Phyllis intensified her efforts until he unloaded four more spurts. She led him to some steps that let them sit with just their heads above the water.

After sitting in silence for a few minutes and after Troy had regained his breath, Phyllis told him "I'm going to dress and go in. I'll send Sarah out. You sit on a chair and wait for her - or stand, whichever you like. She'll bring you in to the rest of the women. This may be easier to say than to do, but relax. The women all like you and want to help. Oh, they don't get to help like I just did, though."

Her parting shot, clever as it was, did not really help Troy at all. Sarah did come out to meet him and they talked for a while before heading inside where the Gang was gathered.

Nancy had played a little dirty by hurrying to pick up Mike and Teri. Troy had barely managed to get over the shock of the Gang's greetings and compliments when the girls entered the house.


As he thought back over his incredible summer, Troy still could not believe it had happened. He had been taking a summer course on athletic injury prevention and treatment. He had just completed his freshman year, and was really not officially qualified to register for the course. During high school, though, he had worked with almost every team. The coaches all knew that he had special talent. He was listed as a PT major, but was thinking of changing to Sports Medicine. Straight A's his freshman year helped, too.

In the class, he met Phyllis, who was acting as a volunteer instructor. She certainly had the qualifications and she was a marvelous teacher. After the first week or so, she seemed to spend quite a bit of time with him, just asking questions. He thought she was scoping him out, hopefully for a job of some kind.

Troy came from a small town family of modest means, and he stretched his scholarship money to the limit. It had been a hard choice to take the summer classes instead of a full time job, but if he could graduate one or two semesters early, it would save a lot of money. He could use the leftover semesters for grad work, still on scholarship. Troy's family was conservative and strict, though not strongly religious. His sexual experience was limited.

During the third week, Phyllis asked him if she could talk to him over coffee. When they were seated, she told him "I want to hire you for a part-time assignment that will last until the local high schools start. You will be the personal trainer for a seventeen-year-old girl who will be a senior in the fall.

"You would run and swim with her and closely supervise her weight workouts. She is staying with her grandmother, a very close friend of mine, and there is first-class equipment there. We can work the schedule around your classes." Phyllis went on to tell Troy all about Sarah and the accelerated makeover project.

"That does not sound like hard duty at all," he observed. "I have to tell you, I'm pretty inexperienced with girls."

"Then the two of you would be well matched. Troy, I chose you because you are very respectful and considerate and I think you will be completely discrete. First of all, I have to get your promise to never mention what I will tell you next, even if you do not take the job. Will you promise that?"

"Uh, sure. What is so serious, though?"

"Except for when you two are out of the house, running, Sarah will always be naked."

He just sat with his mouth working wordlessly for about a minute. Then, his eyes widened and he said "But on the machines! It would be so embarrassing for her!"

Phyllis grinned widely. "Exactly what I expected from you, Troy. Remember, this is a crash confidence building project. My friends and I have seen the idea work very well before. The question is; can you do it? Can you act professional with a raging hardon?"

"Phyllis!"

"Hey, you're going into a body profession, almost like a doctor or nurse. Get over it. You have fours sisters, right? You must have seen all of the female parts at some point."

"Yeah, but, naked all the time! God!"

"Well, for the first day, jerk off twice before you come over, and get a really strong jock strap. Either that, or just let her see the bulge in your pants."

Troy just stared at her grinning face, his own cycling from beet red to deathly pale.

That's when Phyllis mentioned the pay, which really got his attention. "Just think of how much your own self-confidence will build while you get paid quite well. Besides, Sarah is a very sweet girl. Your biggest challenge may be not falling in love with her."

Phyllis's 'warning' about falling in love had been prophetic, and it barely took five minutes on his first day. When he first arrived at Julie's and was introduced to the naked girl, she looked absolutely terrified. She actually wobbled a little and he almost reached out to steady her. After looking him right in the eye, though, her jaw jutted out a little and her shoulders straightened as she said "Let's go do the machines right now before I lose my nerve. I AM going to do this." He was a goner from that moment.

Actually, Troy had not told the complete truth about living as the middle child with four sisters. The baby, Sissy, seven years younger than him, was somewhat of a brat, although she could be as lovable as she chose. He had never decided if she was a true exhibitionist or if she just did it for him. From her earliest years, she always found ways to be naked around him, despite their mother's stern reaction when she was caught.

Their mother showed unexpected discernment when two-year-old Sissy began insisting vehemently "Toy do baf! Toy do baf!" Their mother wisely decided that it would not hurt the nine-year-old Troy to get a more detailed anatomy lesson. From that point on, he became more or less his baby sister's body servant. The older sisters clucked at the way the naked sprite would tow her brother to her room to help her dress. It was a little ritual that Sissy stubbornly refused to outgrow

Sissy was incredibly good at working her mother, something that did not endear her to her sisters at all. Against all expectations, given the general family standards of propriety and modesty, Troy 'supervised' Sissy's baths and dressing until their mother noticed the very first swelling on Sissy's chest.

Sissy did not put up a fuss at the change, perhaps because she knew from her contemporaries that the behavior was odd. That did not mean that Troy no longer saw her body, though. She just went from bold and shameless to sneaky and shameless.

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