Sarah's Story

by Rob Henson

 

Chapter 1 – Sarah is born

There were three points in Simon Lindley's early life whereby if certain events had taken a different course things would not have turned out as they did. This was the first of these.

"Goodnight darling, we'll be off soon." It was his Mother, Clair.

Simon was six years old and just beginning to realise how complicated life could be. He was a quite, thoughtful child who would suck in the knowledge of the world around him and ponder on its meaning until some conclusion or other floated to the surface. He would then often nod to himself, almost imperceptibly, as something fell into place before moving on to the next mystery that life was ready to reveal. He was slightly shorter than his friends of the same age with thick, dark-brown hair, which was just a little too long for a boy, and a serious look until he smiled that is, when his whole face would glow and he would become a different person. Everyone who knew him liked him, especially for his easy going nature; he never had a bad thought about anyone and would always find something nice to say about the most loathsome of characters in his class. This earned him the respect of all who knew him.

His features were soft for a boys' which, as a baby, caused many to mistake him for a girl, something that continued into childhood when, on the odd occasions, he wasn't wearing what were obviously boys' clothes. Simon got his soft looks from Clair, who whilst not a great beauty was extremely attractive, keeping her figure slim through exercise and dieting, something her husband Richard was eternally appreciative of. They were still very much in love always holding hands or kissing which Simon's friends' parents never seemed to do at least when he was around anyway. Clair was in her early thirties and worked at a solicitors office in Warwick where they lived. She was tall and always looked elegant spending time choosing the clothes that suited her best. She kept her hair short which accentuated her features and her make-up was always immaculate. If was as if the professional approach required for her job spilled over into how she ran her life and the appearance she needed to foster. Simon, of course, had no idea what a solicitor was but knew she worked hard and he loved her very much.

"Della is downstairs with her boyfriend so be good."

What else would he be, wasn't he was always good when the babysitter was around?

Della had been looking after him on and off for about two years and they had got to know each other quite well and she liked him a lot. Simon was not at all like her own brother who was slightly older and forever causing her problems. She had just had her sixteenth birthday and was turning into a pretty young woman which had the side effect of attracting boys to her just as the chimes of an ice cream van stir the taste buds of eager young children. Clair remembered what it was like when you had a boyfriend but nowhere to go and so she was happy for Della to have someone to keep her company while she looked after Simon. However she didn't need to be an oracle to know what they probably got up to once Simon was asleep.

"Daddy will be in soon to say goodnight and don't read for too long," Clair said kissing him on the forehead.

"'night Mum," Simon continued reading his new comic which was all about Cowboys and Indians, his favourite stories. A few minutes later Richard, his father, came in and sat on the bed.

"Hi ya champ," he beamed stroking Simon's cheek with the back his strong fingers, "we did good today, well done. Don't know what I would have done without you."

They had been fixing the plumbing and Simon's job was to look after the tools and to hold all the important, tricky things that were too small for grown-ups to handle. He loved it when his dad called him champ. He sat up and gave his Dad and big hug. Richard worked as a factory manager not far away to the north of Warwick and had spent a lot time with Simon during his early years. Simon loved the attention and was in awe of how much his Dad seem to know about everything. There was hardly a question that he put that Richard didn't have some sort of response to and what was even better, Richard always seemed to get him to figure the answer out for himself first which made him feel great when he managed it.

"'night Dad, see you tomorrow." He loved his Dad as well, of course, but in a different way, much more like best mates.

It was Clair and Richard's seventh wedding anniversary and they were going to a new restaurant in town. Simon heard the front door shut and went back to reading his comic. As he turned the last page he put down the comic and turned off the light. He considered going to sleep for a few minutes but did not really feel tired and was wondering what to do next when he heard a giggling sound from downstairs. He got up and crept along the hall very quietly pretending to be a Red Indian tracker just like the one he had been reading about in his comic. He silently made his way down the stairs to the lounge and could see Della and her boyfriend through the gap in the door cuddling and kissing on the sofa.

"Stop it you'll wake him up," giggled Della. Her new boyfriend was tickling her and she could not control her laughter.

"What do you mean him, I thought you were baby-sitting a girl. Didn't I see her last time I was here?"

"No silly, that was a boy, his name is Simon."

"Well never mind about that now give' us a kiss."

They snuggled up on the sofa and the noise diminished but there was something odd going on. His hand was right up inside her skirt and Simon could see Della stocking tops just like his Mum sometimes wore. He almost laughed out loud at the scene and had to put his hand to his mouth quickly to stop the noise. Why would anyone want to put their hand up a girls skirt? Yuk, he thought, some people are really strange. He watched for a few more minutes and then went back up stairs deciding to stop off in the bathroom on his way to bed.

As he stood by the toilet bowl waiting for something to happen he noticed Clair's clothes on the chair. There was the skirt she had worn that day and her blouse, her funny bra thing and her tights and panties. Her high heeled shoes were also under the chair. He picked up the tights from the pile and rubbed them against his cheek feeling how smooth they were and remembering how they looked when they were on his mothers legs. He wondered what they would feel like to wear. He went over and locked the bathroom door and then slipped off his pyjama trousers. He put his fingers in the leg part just like he had seen his Mum do and then pulled it over his toes and up his leg. It was a strange feeling and quite nice. He did the same with the other leg and pulled them up over his waist. They were obviously too big for him but the leg parts fitted snugly. He turned and looked in the mirror. His pyjama top looked a bit like a short dress and with his long hair he noticed that he definitely had the appearance of a girl. It was a very nice feeling. He then decided to try on the shoes which were also too big and very high. How did girls walk in these he thought? He took a couple of steps around the room and looked again in the full length wall mirror. It was odd. He knew he was a boy but could see a girl moving around where Simon should have been. It really felt quite thrilling. He heard another noise downstairs and quickly got undressed, put all the cloths back on the chair and flushed the toilet.

Simon had enjoyed the feeling of wearing his Mums clothes but curiously he only did it two or three more times before forgetting about it completely until many years later. However a significant line had been crossed which would dictate his ultimate future. Something inside his sub-conscious now recognised that he had enjoyed the feeling of being a girl and the sub-conscious never forgets these things.

The second significant event occurred just a year or so later. Clair worked in the centre of Warwick and usually dropped Simon off at school on her way in to the office. During the holidays when Clair and Richard were out working Clair's friend Janet would look after Simon. She worked from home which was convenient for everyone. Janet had a daughter, Sally, who was eight, a year older than Simon but they got on together very well and were best friends even if Sally was occasionally just a little too bossy.

 

One day during the Easter holidays when the weather was overcast and cold Sally suggested they play at 'Schools'. Janet was busy in her office next to the conservatory downstairs so Sally and Simon played in her bedroom at the top of the house out of the way. Simon liked Sally's bedroom, it was full of soft clothes and soft colours.

"OK, what do we have to do?"

Sally got her blackboard and easel from the cupboard and put it near her desk. She placed a chair in front of it.

"I'll be a teacher at my school and you can be the pupil. I have just thought of a problem though," Sally said looking thoughtful and holding her chin with her knuckles.

"What is it?" asked Simon.

"My school is only for girls, you will have to be a girl too. Come on you can wear my school uniform," she got up and went to the wardrobe.

"Here you are, get undressed and put my school dress on, you're the same size as me." Simon did as he was told but looked odd in his boys' shoes and socks.

"Oh dear, that just look's silly," said Sally as she went to her chest of draws. She rummaged around and then handed him a pair of her school tights and knickers. "Put these on too while I get some shoes."

Simon was dazed for a moment but then slipped down his own pants from under the dress. He pulled up Sally's pale green knickers and then slipped the toes of her black tights over his feet and pulled them up his legs. Sally returned with the shoes and he put then on too.

"That's better, you look just like a girl now, except…" She went to her table and found a blue plastic headband which fitted nicely over Simon's long hair and framed the soft features of his face. Simon was so caught up in what Sally was doing he hardly had time to think although he knew he was enjoying being Sally's girl friend.

"Perfect. Now sit down while I give you a spelling test."

They played together for the rest of the morning until Janet cane up to tell then that lunch was ready.

"Oh ! What are you doing?" she asked alarmed at what she saw as she entered the room.

"It's alright we're just playing schools that's all," said Sally casually.

"I hope you're not making poor Simon do something he doesn't want to do, young lady."

"It's OK Aunt Janet," said Simon from the behind the desk, "I like being Sally's school friend, it's fun."

"Well, okay then if you're sure but don't let her force you into anything. Come on lunch is ready now."

They were just finishing off their drinks after eating lunch when a colleague of Janet's from work arrived to pick up some papers.

"This is my daughter, Sally and her friend Si…" said Janet began introducing them but stopped suddenly.

"This is Sarah and she goes to my school," Sally interrupted quite matter of factly and then took a last gulp of milk. "Come on the bell's gone and its time to go back to class." Simon finished his drink, got up and followed Sally out of the kitchen.

"She's a pretty girl," said Janet's colleague.

"Yes," said Sally thoughtfully wondering what she was going to tell Clair, "her mother's a friend of mine."

They went upstairs but on the way back to Sally's bedroom Simon said he wanted to go to the toilet.

"We'll go together, I need to go as well," said Sally making a statement that wasn't going to be negotiable. Simon started to pull up his dress and lifted the toilet seat.

"What are doing?" laughed Sally.

"I'm going to the toilet," said Simon completely confused now.

"Girls don't do it standing up, you have to sit down silly," she laughed out loud.

"Oh, I didn't know," He pulled down his tights and knickers and sat on the seat. When he had finished Sally did the same. It just seemed so natural doing it this way that he never stood up again except when there was no alternative.

"Come on slow coach you have got a lot to learn. Back to school," said Sally with the authority of a head-teacher. Of course, Sally had no idea how profound that statement was.

Clair arrived at five but couldn't stay long. Janet anxiously told her what Sally and Simon had been doing. Clair laughed.

"Oh that's alright, just so long as they weren't any trouble." Clair was very broadminded and guessed they were just experimenting. Later when they were in the car on the way home Simon turned to Clair.

"Mum?"

"Yes darling?"

"How did I become a boy?"

"What do you mean?" asked Clair caught slightly by surprise but she was beginning to get used to Simon's unexpected questions by now.

"Well, did the doctor decide what I should be when I was born?"

"No darling you were already a boy when you were in my tummy." Clair was wondering where this was leading.

"So how do you change in to a girl then?"

"What do you mean," asked Clair thinking back to what Janet had told her.

"What would I have to do to become a girl?"

"Well … it is possible but quite difficult," said Clair cautiously not really wanting to go down this track any more, "why do you ask?"

Simon thought for moment.

"I think someone made a mistake when I was born and I should have been a girl, that's all."

Simon went quiet just looking out of the window, Clair didn't want to push him. She was struck, though, by the finality in his voice, as if he had come to the only, logical conclusion to a particular set of circumstances. Eventually she asked what he was thinking.

"I was just wondering if we are still having spaghetti bolognese for dinner like you promised this morning." Clare laughed out loud and Simon never understood why.

Simon grew into his teens, gradually realising his body was changing as all teenagers discover at some stage, and a number of times recently he had felt a strange tingling sensation around his penis when he had been running or climbing up the ropes at school. One night while laying in bed on his tummy he felt it again and began rotating his hips into the mattress until he had his first climax. He was a bit anxious about what had come out; he had never seen cum before and had no idea what it was. No matter though he had enjoyed the feeling and knew he would be doing it again.

One day soon after, he had just finished having a bath when he noticed Clair's clothes on the chair. He suddenly remembered all those years before when he had tried them on one evening while his parents were out. Yes, he recalled how good it felt and his cock began to harden as he stood there reminiscing. He quickly dried off and put all of her clothes on. First her pink panties and then the tights. He had seen her putting them on many time by now and could do it easily. First place your hand into the toe part and then pull them up the your arm making sure you don't put your fingers through the nylon. Then pull them over your toes and up your leg. First one and then the other. He had not yet fully reached puberty and his legs were still smooth as he pulled up the second and straightened them over his waist. He realised he was breathing fast and his cock was harder than it had ever been when he had been playing with himself in bed at night. This was fantastic, what a discovery he had made. He knew also that it was somehow not quite right but he did not care. He knew that would not be a problem for him, his growing self assurance took care of that for him.

He looked in the mirror and was pleased with the image. He had kept his longish hair and his soft features did not look at all out of place with the other half of the image down below. He saw her dress over the back of the chair and stepped into it pushing his arm into the sleeves and struggling with the zip. Oops, he thought, I have forgotten the bra, might as well make it complete. Once again he had noticed how his Mum used to put it on backwards to make it easier to clip and then turned it around placing her arms through he straps. He did up the dress once again. Finally he put on her high heels and turned back to the mirror. He was thirteen now and about the same size as Clair in all respects. Everything fitted him perfectly. It was a wonderful picture and he stood there admiring himself for sometime. Finally he sat on the chair, lifted the dress and pulled the nylon panties back until his solid cock was free and he then spent the next fifteen minutes bringing himself off in the most beautiful and sensual way hardly able to take his eyes away from the beautiful image in the mirror.

The next couple of years were busy for him, new friends made and lost at school, home-work and exams and, of course, his most importantly his special hobby. He would find his way to the laundry basket most afternoons when he got home from school and had a couple of hours to himself before Richard and Clair came home from work. Sometimes he would borrow a dress from the cupboard where he knew Clair kept her older clothes and occasionally he would experiment with her make-up always being extra careful to leave things as he had found them.

More than that he was beginning to think about his sexuality. He had many friends, both boys and girls and as he reached his teens the various attractions and crushes started to kick in. Deep inside he still felt like a girl but it rarely came to the fore remaining something more natural and obvious without the need to be expressed explicitly except when he dressed of course. He was always friendly and people liked to be with him taking his advice and sometimes even acting as a councillor when couples he knew went through a rocky times as they often did with teen relationships. Lately though he had noticed a more distinct change. He had had a few girl friends but that was expected and they had got up to the usual things that young teens do, playing, kissing and petting although he never really enjoyed those experiences as much as his friends seemed to do. One boy in particular noticed this and suggested they go out for the evening, as friends of course. The boy was known to be gay but there was never a problem with that in the group Simon mixed with. The inevitable happened and that night Simon was left thinking about whether was gay too.

They had gone back to Peter's house and played music in the bedroom. Peter's parents had gone out for the evening so they had the house to themselves. Peter was tall and handsome and not particularly effeminate, indeed one would not have guessed at his sexuality had they not known about it. Peter gradually sidled up to Simon and put his arm around his neck. They were laughing about something that had happened at school but when their eyes met Peter moved forward and they kissed. It wasn't unpleasant for Simon, in fact he was beginning to enjoy it especially when Peter undid his trousers and stroked him, very slowly. They ended up masturbating each other until it was time for Simon to leave.

Simon thought about the experience and how nice it was, over the next few days although there was still something not quite right, he had the feeling it could have been even better but he didn't know how. He then began to realise why. He found he was wishing that he been wearing Clair's clothes while he had been with Peter. It took a further few months and another close friendship for him to realise what this really meant.

Simon got to know Ben very well. Ben was 17, a year older than Simon, and lived on the other side of Warwick. They met when the group was out and about and frequently found themselves talking together whenever they were near each other. Ben too had a confident air about him, always wearing the latest designer fashions with a hair-style that never seemed to look the same twice. His black leather jacket was his pride and joy.

Ben had had a number of girlfriends some of whom still hung around the group. However, no one in the group knew that he had also had a boyfriend. It was after the second encounter with him that Ben had realised he was probably bisexual. Things calmed down for him after that as he accepted his sexuality but he continued to keep the male side of his sex life discreet, for the time being anyway. The boys he had been with eventually moved away and hadn't really known any of the group in any case.

When he first saw Simon he knew he was attracted to him but something seemed different this time and he wasn't sure what it was. Simon was good looking but in a pretty rather than handsome way. It was as if both sides of his sexuality had come together all at once, something he had never felt before. He knew he would have to get to know Simon better, maybe even to seduce him. Ben was intrigued by this image and knew would have to make a play. He would do it slowly and gently though, getting to know him as a friend before making any sort of move. He spent the next few months becoming better acquainted with Simon, earning his trust and waiting for the right moment to arrive which it did soon after.

  

  

  

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