A Schoolgirl Story

by Jessica Swift

 

Jason Sheen was eighteen when he moved to River Falls with his mother. Ever since he was a small child Jason had lived with just his mother, Felicity, and he could no longer remember anything about the father who had abandoned the two of them when Jason was just three years old. Fortunately, Felicity Sheen had inherited a lot of money from her late father. In fact, it was enough to pay for both her and Jason's upkeep comfortably without her ever having to work. Not only that, but it paid for them to have quite a classy home in the rich town of River Falls and for Jason's mother to lead a rich and glamorous social life of dinner parties and other functions.

Although his mother was certainly a glamorous socialite who had many male admirers, Jason himself was quiet, effeminate and sensitive and as a result didn't get out much or have many friends in their old town. Jason viewed the move to River Falls, just after Christmas in his senior year, as a chance to start afresh, develop a new and more popular image for himself. The subject of Jason's new education was the discussion at the dinner table as Jason and his mother sat on the terrace of their new home admiring the view of the surrounding countryside. It was almost the end of the winter break and Jason and his mother needed to decide whether to send him away to a private school or go to the local public high school. The high school did not have a great reputation when it came to academic standards but there were no local private schools for boys and so Jason would have to be sent to board a long way from home where he couldn't visit frequently which he didn't want.

Because he was such a shy, introverted person and because all their constant moves meant he never had time to settle down and make friends, Jason was very close to his mother. Years of living alone, just the two of them, meant that their relationship was a lot closer and more affectionate than many mothers and sons. They liked to joke around together a lot and their relationship was actually quite flirtatious. Indeed, Jason's mother looked young enough that people had mistaken them for a couple when they went out together. Although this was a little weird, Jason couldn't help but feel a little flattered that people thought it possible that he was together which such a beautiful, glamorous woman.

Dinner was a flirty, fun affair with wine flowing freely as Jason and his mother diverged from the serious subject of Jason's schooling onto lighter, more entertaining topics. Dessert was over and Jason was feeling very light headed from all the wine when his mother laughingly said, totally out of the blue:

"You know, there's always Firwood, you could go there," she said with a smile.

Firwood Private School for Girls was the the local expensive and exclusive girls' prep school with a very high reputation for academic excellence. It was just the sort of school that Jason and his mother were both looking for, but for one problem. As the name would suggest Firwood was a single sex girls' school. Jason laughed, he was drunk, his head was spinning and his mother was now just making light of the whole situation:

"I don't think I'm really Firwood material," he jokingly responded.

"Nonsense," replied his mother, with mock outrage, "You're the equal of any of those Firwood girls."

"Somehow, I think the uniform is a little more appropriate for them," Jason laughed.

"Nonsense," said his mother again, "I know it would be great for you. Come with me."

Grabbing him by the hand, Jason's mother took his back inside the house and up the stairs to her bedroom. Head still spinning, Jason followed her, laughing at the fun of the situation. Laid out on his mother's plush double bed was the Firwood uniform. Despite a reputation for high moral standards, the Firwood uniform was every bit the archetypal schoolgirl uniform, with a thin white blouse, a short, blue and green plaid skirt and matching tie and knee high white nylon stockings. Jason had seen some of the Firwood girls around town when he had first moved to River Falls in November and had certainly been impressed with how the uniform looked on them.

"It's a sexy uniform isn't it?" his mother said, and Jason was forced to agree with her, it certainly was, in fact it was getting him a little excited just at the thought of all his schoolgirl fantasies, "And I think it'll look really sexy on you."

Jason wasn't entirely sure of what was going on as he found himself allowing his mother to strip him from his normal clothes until they lay in a pile at his feet, leaving him exposed and naked, cock embarrassingly slightly erect at the smooth, gentle touch of his mother as she helped him strip off.

"Don't worry, we'll make you look just as good as any of those Firwood girls," his mother grinned at him.

Jason felt a little surprised when she opened her underwear drawer and handed him a pair of her white lace panties which, only feeling partly in control of his actions, he slipped up his legs as his mother helped him into a matching bra which was stuffed with padding to give the impression that he was as bustily well endowed as she was.

Jason didn't admit it to his mother as she helped him slip into the short, pleated skirt, but he had long fantasised about dressing up as a girl and finding out what it was like to be one. Now, the sensual feel of the clothing against his body made him feel even more feminised as he buttoned up his blouse and slipped into the knee high stockings, making him more aroused than ever. Looking at his girly reflection did little to abate Jason's arousal. Through his drunken, hazy vision he was even more excited at the sight. Although with relatively short hair and no make-up, the girl Jason saw in the mirror still looked great in the sexy uniform. Certainly the kind of girl that Jason would have jumped at the chance to be with. The only tell-tale sign was the now obvious tent in the front of his skirt.

Jason's mother ran her hands down over his ass in the little pleated skirt, "Jason's such a masculine name, what would you like to be called instead, my sexy little daughter?" she asked as she landed a playful pat on his panty clad ass that almost caused his cock to explode.

Jason already knew the answer to this one too, it lay deep in childhood games of Peter Pan and how he had never wanted to be a lost boy but always prefered the part of: "Wendy," he said it a little too quickly and confidently if he had wanted to conceal his fantasies.

Although it would have been hard to conceal the excitement and pleasure that the uniform was giving him given the huge bulge in his skirt. His mother had clearly noticed as she ran her hand down the front of his blouse to the place where his cock bulged out. Jason felt his body tremble as his mother touched his erect cock through the material of his skirt and whispered in his ear in a deep, sensual voice:

"I can't have my Wendy looking like this can I?" she purred, "I'll have to do something about that."

With that she shocked Jason by dropping to her knees in front of him, lifting up his plaid skirt and pulling the lace panties down around his ankles. If he was more sober, or thinking straight, he might have stopped her, she was his mother after all. If he was more sober, Jason might have never allowed himself to get into this situation in the first place. As it was, Jason was really drunk and felt himself just give in to his urges as his mother licked the string of pre-cum from the end of his cock and slowly slid it's full length into her mouth. She might have been his mother and over forty years old, but she was still totally gorgeous as she slurped on his erect member, her full breasts, not even slightly sagging, jiggled beneath her as she pushed her shiny brown hair from out of her brown eyes and concentrated her full scarlet lips around her son's cock.

Felicity Sheen's cocksucking on her son was truly superb, doing everything right, but any kind of stimulation would have been enough to send Jason over the edge right then, after the turn-on of the the schoolgirl outfit he was wearing and the sexual attention from his gorgeous, experienced mother. Sure enough, it only took a couple of minutes for Jason to spurt a huge load of warm, sticky cum into his mother's waiting mouth. She swallowed every drop and pulled his lace panties back over his cock and pulled his skirt back down again. The reflection now was a fully sexy schoolgirl and Jason smiled with pride to see it. The last thing he remembered of that evening was his mother drawing him into a liplocked kiss as she pushed his salty cum down his throat.

***

Jason Sheen woke up the next morning in his own bed, dressed in his usual night time dress of boxer shorts and a T-shirt. He felt really groggy, his head throbbed with a hangover and the events of the previous night seemed a blur. His boxers were slightly stained with his cum and it dawned on him that he'd had another wild fantasy and nothing more. With mixed feelings of strong relief but a little disappointment he dressed and came down to breakfast.

Jason's mom was already up and setting his breakfast of eggs and bacon in front of his place at the table. She grinned at him as she did every morning, nothing had changed, and that told Jason that he had just been absorbed in a powerful fantasy. However, Jason couldn't shake the image of his sexy mother going down on him from his head, and had to sit down quickly to avoid his mother seeing the slight erection in his jeans at the sight of her very long legs protruding from her very short silk dressing gown. Jason smiled back, relieved to have avoided any embarrassment. His mother turned back to him:

"Oh, by the way," she smiled, "I talked to Principal Stanton at Firwood, and you can start there at the beginning of the new semester, Wendy."

Jason reeled back in shock, almost falling back off his chair, and totally re-aligned his views of the night before. How much of it did he remember? How much of what he thought he remembered really happened? His head was in a total daze.

"You are joking, aren't you mom?" he asked, unsurely.

"No," she smiled re-assuringly, "Firwood is the best school in the area and it's where you can get the best education. You should be pleased to have managed to get in at this time of year, I had to pull a lot of strings with Principal Stanton. He and I have a certain understanding."

"B. . .but I'm a guy," Jason stuttered, "I can't go to an all girl's school."

"Don't be silly," his mother smiled, "I've always wanted a daughter and you showed last night how good a daughter you could be and how much you liked being Wendy," here she winked, "We've got a couple of weeks to make you perfectly comfortable as Wendy before school starts and I'm sure you'll be one of the prettiest, most popular girls in school."

Jason's head was still spinning, he was confused and hung over and this was all happening so fast. Really, he didn't know at all what to do, but one thing was for sure, he relished the chance of being Wendy again and even now, more sober, he was ready to give his body to his mother to do whatever she wanted to transform him into Wendy.

***

"Hi Wendy," said the perky, enthusiastic dark haired girl in Firwood's sexy uniform, "I'm Danielle Washington, I'm going to be your room-mate. Principal Stanton wants a few words with your mother, so I'm going to show you around the school."

Wendy smiled back, "That would be great," she told Danielle in the purring, feminine voice she had perfected over the last couple of weeks.

Wendy had arrived for her first day at Firwood Private School for Girls that morning. Her mother had driven her out to the school and Danielle had met them at the school's imposing iron gates with the school's crest and motto hanging above them. Firwood was a boarding school and Danielle had been asigned to be Wendy's room-mate and to show her around and make her feel at home at the school. Although Wendy was nervous about living away from home and from her mother, Firwood senior girls were allowed into River Falls town which was not far away and where Wendy could see her mother. This was not the only thing that Wendy was nervous about starting Firwood. She was, by instinct, the type of person that tends to worry about things a lot and the thought of starting a new school and a new life completely different from the one before made her stomach turn. She hadn't had any breakfast that morning out of nerves.

Although she had spent two weeks living entirely as Wendy and totally perfecting her feminine persona, Wendy was still petrified that someone would discover her secret and petrified about what would happen if they did.

"There's no need to look so nervous," Danielle smiled an open, friendly grin as she took Wendy by the hand and led her over to the red brick dorms of the school while Wendy's mother went the other way towards the principal's office, "This is just like any other school you've been to."

Wendy felt herself a little involuntarily excited by the closeness and touch of Danielle, as Jason she had never had the chance to be this close to women, but her new life as Wendy opened up so many new opportunities. Danielle was a gorgeous, slightly upper-class girl that was exactly the type that Jason would have fantasised about with straight dark hair over the shoulders of the white Firwood blouse that was unbuttoned by a couple of buttons with her blue and green tie pulled down a little to give a glimpse of her neck and cleavage. She had very large breasts for her age and carried herself in a way that thrust her chest even further out. She was also extremely welcoming and friendly in a way that put Wendy slightly more at ease.

Wendy herself didn't look too bad either. Gone was the slightly boyish un-made up look of before, now she was every inch the sexy schoolgirl. Her legs, encased in the knee high white stockings and short plaid skirt, were smooth and shaved, her sensual red bra contained some expensive but convincing silicone false breasts that her mother had bought her as a present for getting into Firwood and gave her a more feminine hour glass figure. Her face was now made up with shiny lipgloss, mascara and soft blush and her hair, although still quite short, was no longer boyishly short but had acquired a stylish feminine look from one of River Falls' expensive stylists. Going into town that day, Wendy had drawn a lot of admiring looks from guys and that had given her extra confidence. With a couple of weeks of intensive practice and help from her mother, Wendy had learnt to walk, talk, eat and act in practically every way like a girl.

"This is our room," Danielle said, opening the door for Wendy, "That's your bed and this one's mine."

They were inside the red brick dorm in a fairly spacious room with a comfortable looking bed on each side. The room was sparsely furnished but each side had a wardrobe, a desk and a chair. Danielle's side had a window that looked out onto the pleasant, wooded grounds of the school. Wendy's side was totally bare, but Danielle had personalised hers a little with a few books and posters on the wall.

The room was joined to a virtually identical one next door by a small bathroom containing a shower, toilet and wash basin. Danielle took Wendy through this room into the one next door in which a girl sat at her desk, furiously writing something with a lot of books infront of her, and another lay back on her bed more leisurely reading. Danielle introduced the writing girl as Michelle Norton, a short, slightly plump brunette and the girl on her bed as Jacqui Simpson.

"Wendy's my new room-mate," Danielle explained, "She just transferred here and I'm showing her around. Do you guys want to come?"

Jacqui languidly put her book down and stretched her long, sexy legs off the bed and stood up as Michelle turned and smiled:

"Where have you transferred from Wendy?" she asked in a friendly way.

"St. Henry's," said Wendy, "A school back east."

"Isn't that a boys' school?" said Jacqui looking a little confused as Wendy suddenly realised her mistake.

"No," she said, quickly covering up, "Ours was a rather less prestigious girls' school."

After this initial scare, Wendy certainly found herself feeling more relaxed and comfortable as the three girls showed her around the rest of the school, despite the fact that it was January it was still quite warm because of how far south River Falls was. Firwood was a school in a very attractive location and seemed in a lot of ways to be just the kind of place Wendy had always wanted to go to school. She was also increasingly enjoying the company of the other three girls, Michelle was careful and a little neurotic, Jacqui had only arrived at the school a few months earlier but had already established herself as the total opposite to her room-mate, despite which the two seemed really close friends. However, it was with Danielle that Wendy really clicked. Wendy found her room-mate's company very relaxing and enjoyable and it was as if they had known each other for years so easy was their conversation. Danielle was really warm and friendly and desperate to make Wendy feel happy and relaxed at Firwood and, by the time the tour finished, Wendy had certainly begun to feel at home here.

Indeed, as she saw her mother come out of Principal Stanton's office and come over for one last hug, Wendy felt like she could be very happy here over the course of the year and it was with slightly less regret than she had thought that she stood and watched her mother drive off and the gate closed behind her. One thing that did trouble Wendy slightly was her mother's slightly dishevelled look, hair out of place, lipstick smudged. Maybe she was reading too much into it, but Wendy had seen that look once before, on the night she had first dressed as Wendy. For a moment she wondered what her mother had really done to get her into such a prestigious school in the middle of the year.

"Don't worry Wendy," Danielle placed a re-assuring hand on Wendy's arm, "You'll be able to see her again soon, and anyway we can have loads of fun here together."

***

After a week at Firwood, Wendy felt perfectly happy and settled into the routine of things when Principal Stanton called her into his office to see how she was settling. By now, Wendy felt perfectly comfortable in both her new school and her new persona. She was doing well in all her classes which she found suitably interesting and challenging and had adapted well to life at boarding school. Unlike Jason, Wendy was quite popular at Firwood. Danielle had managed to coach her through all (or nearly all) of her anxieties and Wendy was now becoming an established member of Danielle's group of friends including Michelle, Jacqui and a few other pretty, clever girls. In fact, for this week Wendy felt she had never been happier or more accepted than at Firwood and all it took was the simple transformation from Jason into Wendy. The next day would be Saturday and Wendy planned to go shopping in River Falls with her new girl friends.

Now, however, was Friday afternoon. Her last class of the week, American History, was over by five o'clock, but instead of joining Danielle and the others back at the dorm, which would, in a matter of hours, become like one enormous slumber party, she had an appointment with Principal Stanton. Although she really wanted to spend the time with Danielle and her friends, Wendy was aware that this meeting was just another part of the friendly, helpful system at Firwood that was allowing her to settle in so well.

Principal Charles Stanton was a tall man in his early forties. He was quite a commanding presence, athletic and youthful looking. Danielle had told Wendy that Principal Stanton had been a successful amateur tennis champion in his youth and Wendy could well believe it to look at him. His sandy blond hair was greying slightly to make him look a little distinguished, he wore thin wire glasses that Wendy thought he probably wore simply to look academic. He was dressed in a neat tweed suit as he ushered Wendy into a chair in his immaculate, expensively furnished office. His desk was large and dark wood as were the packed bookcases behind him. He sat down on a leather armchair and Wendy sat in an equally comfortable chair on the other side of the desk. He looked at her with inquisitive blue-grey eyes and smiled.

"So, how are you settling in, Miss Sheen?" he asked.

"Really well," Wendy beamed, "I'm really loving everything about Firwood."

"Your mother said you were very eager and willing to learn," he said, "And I see she was right."

He smiled again, slightly wider this time, in a way that made Wendy uncomfortable for the first time and reminded her of her mother's dishevelled appearance coming out of the same office a week earlier. Once again, she wondered what her mother had done to get her accepted here, and this time she also began to wonder whether Principal Stanton was aware of her secret.

"You know Wendy, you're mother's a very special woman," he continued, "And she tells me that you're a very special girl."

Wendy felt increasingly sure that Principal Stanton must know something about her past, after all, some identification must have been needed to register with the school. Maybe that's why her mother had had to come to such an arrangement. Principal Stanton had now got up and was walking around his desk towards her.

"I try hard to pay a lot of personal attention to all my new students," he said, placing a hand on her shoulder as Wendy gulped at his closeness and her anxieties began to come flooding back, "Especially students so specially gifted as you."

With this he winked at her and Wendy was sure by now that he was aware of who she really was, as his firm hand now found itself placed on her bare knee as he sat down on the arm of her chair. Wendy had sat with her legs demurely together as her mother had taught her, but as he spoke, Principal Stanton began to stroke the inside of her smooth, bare thigh as he leant towards her to speak.

"You know, Wendy," he said, leaning close to her ear as his hand crept inside her thigh towards her stylish red lace panties, "If I can help you out so much like this, there's things you can do to help me out."

His other arm was draped around her shoulder as he caressed her breast. In spite of all her nerves and worries, Wendy couldn't help but be turned on a little by the touch of this athletic, powerful man. Jason would never have felt any feelings of attraction towards a man, but for Wendy it just felt right to have just a little bit of a crush on a powerful man in authority like her principal. By now, if he didn't know her little secret he would do soon. Wendy's hands rested demurely in her lap, serving the dual purpose of making her sit in a ladylike way and covering up her growing arousal. However she felt a shiver of both thrill and fear as Principal Stanton's hand on her thigh crept inside her skirt and came closer to her panties.

"You do know what you could help me out with, don't you?" he smiled, now unmistakably lecherously.

As he said this, he laid his hand on one of hers and picked it up and placed it on the crotch of his tweed pants, through which Wendy could feel a firm, strong erection. Principal Stanton moved her hand up and down his crotch, jerking his cock off through the material of his pants in time with caressing her breasts. Wendy could feel herself unwittingly really turned on by now, and her own cock was pretty firm and uncovered by her hand on Principal Stanton's crotch. As Principal Stanton stood up he looked down at the bulge in her blue and green plaid skirt and grinned:

"Felicity was right, you certainly are a very special girl," he said as he stood before her and unbuttoned his pants.

Principal Stanton allowed his pants to drop to the floor, releasing hid thick, hard cock, all eight inches of it, towards Wendy's face. Wendy knew exactly what was expected of her, and came to realise what her mother's "understanding" with Principal Stanton was. Just a month earlier, Wendy would have been disgusted at what she was about to do, but now her cock straining against her panties and skirt told her how much she wanted this.

Slipping from her chair, Wendy dropped to her knees so Principal Stanton's cock was just inches from her scarlet mouth. Wendy could almost feel herself beginning to drool as she licked her lips in anticipation before slowly extending her tongue to the tip of her principal's cock and drawing out a long, glistening string of his pre-cum between his cock and her mouth. Meanwhile, she reached up with one hand and slowly began to jerk off the base of his cock which he was obviously enjoying. Wendy opened her lips just a little and let the head of her principal's cock slide into her mouth. She gagged on it after only about four inches but she continued to bob up and down on it as she jerked off the base. By this point Wendy was really feeling turned on and reached under her skirt and into her panties and began to jerk herself off in time with her sucking her principal's cock.

It wasn't long before Principal Stanton gave a grunt of pleasure, his cock twitched inside Wendy's mouth and he blew his load down her throat, at that exact moment Wendy felt her own orgasm welling up inside her cock and, before she could stop herself, she came into her panties, much to her embarrassment. Principal Stanton stood back, pulled his pants back on and sat back behind his desk while Wendy still knelt on the floor, slightly bewildered by what had just happened.

"Thank you Miss Sheen, that will be all," Principal Stanton dismissed her as if they had just been having a brief talk.

Still slightly bewildered, Wendy stood up, straightened her skirt and left the room, walking slightly awkwardly with her panties full of cum and quickly hurried into the bathroom near to the principal's office to clean up. Locking herself into a cubicle, Wendy sat down on the toilet and just thought for a few minutes, trying to take stock of the situation. As she saw it, it seemed that her mother had agreed that Principal Stanton would allow Wendy to be educated at Firwood and would ignore any reason why she should not be there in return for sexual favours. Jason would have felt appalled and not a little disgusted by this thought, Wendy however felt a thrill of excitement, despite his age, Principal Stanton was a good looking man and he could teach her things about being a woman that her mother never could. In fact, as Wendy took off her cum stained panties, the only thing she could think to do with them was to lick them clean of her juices, which she found quite a turn-on in itself. Leaving the cubicle after making sure she was alone, Wendy examined her reflection, wiping a tell-tale drop of cum from her lips, she re-applied some make-up and combed her slightly dishevelled hair and walked back to her dormitory feeling strangely ecstatic.

***

The next day was Saturday and Wendy's first weekend as a Firwood girl. Saturdays provided an opportunity for the girls to go into River Falls town and meet people there. Danielle and her friends were going to do some shopping and meet some people they knew at the high school and they asked Wendy along. Wendy was pleased to have this opportunity to spend time with her friends outside school and accepted happily. She was also keen to have the chance to indulge her recently found femininity with some shopping. It was Firwood school rules that the girls had to wear their uniforms at all times, even at weekends and outside school, that way they would continue to represent the school and behave accordingly. Heads of guys both their age and much older turned at the sight of the provocatively sexy uniforms on these well formed eighteen year old girls. As well as Danielle, Michelle and Jacqui, they were also accompanied by Carolyn Lancaster, tall, blonde and one of the prettiest and most popular girls at school, Wendy was still a little in awe of Carolyn, but she and Jacqui were very close and friendly together, and Nicole Grant who Wendy didn't know very well at all but was a good friend of the other girls.

In shops, as the girls looked for clothes, shoes and jewellery, all the male shopping assistants rushed to help them, anxious to please and impress the sexy schoolgirls. Wendy had to admit that she felt a little flattered by the attention she was receiving as lots of men helped her with her every desire, she even flirted a little with them, tossing her hair and batting her eyelids and, every so often, giving a coy, flirtatious grin. This was the first time that Wendy had been outside the grounds of Firwood school as Wendy with these girls and she felt like she should have been nervous or a little self conscious but she was loving every minute of it, totally comfortable in herself and in the company of the other girls. It was as if her act of feminine sexuality with Principal Stanton had realeased some further femininity within her and she was now becoming more Wendy and less Jason at every moment, with every girly activity she embraced.

Exhausted and carry large bags of shopping the girls stopped at River Falls' one and only diner for lunch. This was the place where all the town's teens hung out around lunchtime and the diner was absolutely packed, Wendy saw a few other white blouses and plaid skirts of Firwood girls, mostly sitting with guys from the town. There were no tables at all free and the girls were thinking of leaving when they were called over to a booth in the corner where there were some seniors from the high school who appeared to know Carolyn, in particular, very well. The six girls had to squeeze into the small space of the booth with the three high school guys and one girl who knew Carolyn, but Wendy was just happy to sit down. Wendy was squeezed in next to Danielle, the short plaid skirts of their uniforms rose above their knees and Wendy could feel the smooth touch of her friend's thigh against hers. Maybe all of her masculine feelings hadn't totally disappeared as she felt a stirring in her groin at Danielle's close touch and at the sigh of her as she laughed and tossed back her long dark hair and thrust out the curve of her beautiful breasts.

Wendy tried to distract herself from her uncomfortable arousal at her friend which could cause all manner of complications, and turned to look at the three high school guys. Nicole's half-brother, Greg was a tall, slightly clumsy looking guy with floppy hair and a slightly distant _expression in his grey eyes, he wasn't really Wendy's type - What was she thinking? Until the before she had never thought about guys that way and now she was analysing whether they were her type. Meanwhile, Jake Leeds was a more conventionally good looking athletic guy who was on the high school football team, unlike Greg he was quite loud and brash andhe and Michelle seemed quite absorbed with each other spending the meal mainly just talking to each other and sharing a shake. It was the third guy, however, who really interested Wendy. Chris Hudson had a tanned, surf dude look even though it was winter, his hair was made up of matted blond dreadlocks. His blue eyes sparkled with a certain fun loving joy and were right now running all over Wendy's body in a way that made her feel at once self conscious and excited as she found herself imagining the feel of his hands running all over her body. She was almost as intent on staring at him and found herself laughing particularly loud at anything he said and trying to further attract his attention. She did manage to attract the attention of the girl, Jennifer, a tall, tanned, gorgeous blonde who was talking to Carolyn but turned to glare at Wendy if her attentions to Chris were too close. Wendy was a little worried to discover this Jennifer was the daughter of Principal Stanton. At one point, Chris caught her eye while she was staring at him and grinned at her and winked in a way that made her flush red and look away.

"You and Chris seemed to hit it off," smiled Danielle, as ever aware of Wendy's mindset, as they sat reviewing their shopping purchases back in the dorm that evening.

Wendy was lying back on her bed with her shoes kicked off and her legs in their white nylon stockings stretched out while Danielle sat at her desk, trying on some new dark lipstick she'd bought while they talked. Wendy didn't really know how to respond, after all she did find herself attracted to Chris, but her tiny shreds of masculinity still made her a little nervous and Jason's self confidence issues made her worried that Chris was a little good for her.

"I think Chris is a little out of my league," she laughed.

"Not at all," Danielle smiled with her dark crimson lipstick, "You're a very pretty girl," she winked in a way not unlike how Chris had winked at her earlier and Wendy felt a worrying stirring in her groin again, "You know, I could set you up on a date with Chris, how about that?"

***

After quite some persuading that evening from Danielle as well as Jacqui and Michelle, Wendy finally agreed to let the other girls set her up on a date with Chris, telling herself that Chris wouldn't be interested in the likes of her anyway and that at least it would shut her friends up. However, secretly she hoped he would say yes, and when he agreed to meet her at the diner the following Saturday, Wendy was filled with both delight and nerves.

It was Saturday afternoon and Wendy sat in front of the mirror getting herself ready for her date. Danielle was just getting out of the shower and talked to Wendy as she came back into the room, wrapped in just a small white towel. Wendy was dressed in her Firwood uniform, her white stockings feeling good against her smooth legs and her white blouse clinging tightly to her figure created by the convincing false breasts. Her hair was getting longer and more feminine by the day and she was using Danielle's hair styler to create a look she liked.

Danielle swayed over towards Wendy, who tried not to look in the mirror at her friend's body, still glistening wet with the lengths of her legs and the top of her large breasts exposed by her small towel. Wendy tried instead to focus on applying her lipstick, but her hand was shaking with nerves and conflicted feelings over her coming date and the sight of her room-mate's semi-naked body.

"Here, let me help you with that," said Danielle, turning Wendy's chair around so she could now look nowhere but at her room-mate, whose dark, wet hair hung over her face in a sexy, dishevelled look.

Wendy felt an electric thrill as Danielle place her hand on Wendy's bare knee and took the lipstick from her, she smiled as she traced Wendy's lips with the sensual scarlet colour they had both thought would be perfect for Chris. Right now though, Wendy wasn't thinking about Chris at all, her mind was taken up by the closeness and intimacy of all Danielle's bare, wet flesh. As Danielle finished applying the lipstick and licked her own lips slightly self consciously, it took all Wendy's efforts not to reach up and kiss them.

"There," Danielle smiled, "You look lovely honey, there's not a man around who could resist you, nor a lot of women either," she winked again like she had a week earlier.

Wendy was suddenly confused and flushed redder than she had when Chris had winked at her in the diner. She didn't know what was happening, was Danielle just being friendly or was it something more than that? Even if Danielle was flirting with her, Wendy wasn't really sure what she would do in her current confused state of mind and body to deal with it. Fortunately, Danielle's back was turned as she reached to pick up her clothes from on her bed. Wendy tried not to but she could clearly see her friend's round, pert ass beneath her short towel.

Wendy hurried out of the dorm room before she became any more excited and her secret became obvious. As she was leaving, Danielle wished her good luck and gave her a hug and a friendly kiss on Wendy's cheek that seemed to linger there a while. Wendy was so turned on leaving the dorm that she thought about slipping into the bathroom to jerk off as she had done a couple of times since arriving at Firwood when the pleasures of being a woman had become too much for her. However by the time she had walked in the cold from Firwood campus in the woods all the way to River Falls town, a quite long walk and one that most of the girls never bothered with without good reason, her excitement and arousal had subsided and she was feeling ready for her date, relieved to be away from her potentially embarrassing arousal over her room-mate.

Chris was already waiting in a booth at the diner when Wendy arrived five minutes late. Instantly, on seeing Chris, her nerves about the date began to flood back. He greeted her with a friendly wave and she sat down opposite him and ordered a cheeseburger. At first conversation didn't flow and things were a little awkward between them. Chris' cocky jokiness seemed to disappear now he was no longer in a big group but now in a more intimate one on one situation, while Wendy, for her part, had never been on a date with a guy before in her life and was feeling very nervous. However, as the date progressed, Chris seemed to feel more relaxed and confident around Wendy and his high spirits returned, clowning around with the food in a way that, although childish, Wendy couldn't help but giggle at. This seemed to lighten the mood and, after their food was taken away, Chris leant in closer to Wendy across the table. Once again, Wendy felt a flush of nerves and excitement as Chris took her hands in his and leant his face towards her. Far from discouraging her though, this closeness made Wendy want him more. She was beginning to lose herself in a fantasy of what things could be like if she were an ordinary woman just on a date with a cute guy. Wendy leant in across the table until her face was just inches away from Chris' and she was staring directly into his eyes. Earlier on she would have worried about whether this closeness would allow Chris to see her masculine flaws beneath her make-up but now she was lost in thinking and feeling she was truly a woman. As she leant in towards him Wendy, almost without realising it, leant in further and planted her lips against his, kissing him. It was the first time she had ever kissed a guy and it was simply a very brief peck before she pulled away feeling embarrassed and not knowing what to do:

"Sorry," she said, flushing red, "I don't know why I did that."

"Don't worry" Chris replied with a smile both reassuring and cheeky, "You could have done this."

With that, and without giving Wendy time to ask what he meant, Chris grabbed her head and pulled her face back towards him, locking lips with her in a way that was far from the polite peck that Wendy had given him. For Wendy, the kiss seemed to last for hours, but she still wished it could have lasted longer. As her lips opened and allowed Chris' tongue to thrust inside her mouth she felt aroused and excited by all the possibilities being a woman could offer her. When they broke from the passionate kiss, Wendy's lipstick was smeared all across Chris' face. Taking her by the hand, Chris smiled sheepishly at her:

"Do you want to come back to my place, Wendy?" he asked.

Wendy didn't need any more encouragement than that and soon found herself led by the hand out of the diner and into Chris' car. Chris drove them back to his house which wasn't far away. Like most of the people in River Falls, Chris' family was very rich and that was reflected in the large, luxurious modern house that he drove Wendy to on the edge of River Falls. He let her into the house and shut the front door behind them. Once inside, Chris took Wendy in his arms and once again they locked lips in a passionate kiss.

"My parents are away all day," Chris said as they broke from the kiss, "So we can do whatever we like," at this he winked seductively.

Each almost as eager as each other, they ran upstairs to Chris' bedroom. Wendy looked around the room, eager to find out what kind of guy Chris was. The room was large but far from tidy, there were clothes strewn all over the floor, mostly the baggy shorts and hawaiian shirts that Chris tended to wear. The walls were covered almost entirely with surfing posters or posters of gorgeous women in bikinis. That was all that Wendy had time to take in before she was once more locked in a passionate embrace with Chris as Chris pushed her back onto the large, soft bed and Wendy opened her smooth legs in the plaid schoolgirl skirt and white stockings and wrapped them around him.

It wasn't until Chris was unbuttoning the white blouse of her uniform to reveal the sexy lace bra beneath with one hand as his other crept inside her plaid schoolgirl skirt and up her smooth thighs that Wendy realised that Chris was just inches away from discovering her secret. By now, Wendy was really excited and turned on and she really desperately wanted Chris like she had never wanted anyone before. The hard cock that sprang out of Chris' pants as he unzipped them showed he wanted her almost as much. But Wendy knew that Chris wouldn't want her so much once he got inside her panties and that she could probably kiss goodbye to the chance of any kind of sexual pleasure with him. Quickly, Wendy thought back to the time, barely two weeks before, when Principal Stanton had called her into his office. That time, he had wanted Wendy to give him a blowjob, maybe she could do the same once again.

Wendy pushed Chris from her, just as his hand crept inside her thigh once more and knelt on the carpet of his room with his cock sticking right out towards her face. Unlike with Principal Stanton, when she had been nervous and unsure of herself, this time Wendy felt able to take control of the situation, slowly sticking her tongue out between her scarlet lips and running it over the head of Chris' cock. Chris groaned appreciatively as Wendy let the head of his cock slide between her lips as she began to use her hands to jerk off his shaft and play with his balls. Slowly and teasingly she gradually took the whole length of his cock into her mouth and began to bob up and down on it while Chris' groans of appreciation became faster and more urgent. To oblige both his desire and her own, Wendy began to suck his cock faster and more eagerly, throwing everything she had into it. Even though she had only been a woman for about a month and only sucked her first cock a couple of weeks earlier, Wendy felt she was already becoming a talented and eager cocksucker and Chris from his reactions seemed to agree. Wendy was beginning to feel wholly like a woman and began to think that maybe this was what she was supposed to be. It didn't take long of Wendy's increasingly skilled attentions to bring Chris' already quivering member to a climax and she eagerly continued to hold his cock in her mouth as he shot his load of tasty juices right down her throat. Wendy continued to jerk his cock off as she sucked him dry of all her juices until her mouth was full to overflowing with his cum and she had to let his cock slip from her mouth as he continued to shoot his load across her face and chest. Finally, after he had finished his incredible orgasm, Chris brushed his blonde dreadlocks from his eyes and smiled down at Wendy and said:

"Wendy, that was incredible."

And that was pretty much how Wendy's first date with a guy ended. As soon as she could, Wendy told Chris she needed to clean herself up and managed to sneak to the bathroom without Chris noticing the telltale signs of her arousal. The whole experience had made Wendy incredibly excited and turned on and, as soon as she was in the bathroom with the door locked behind her, she sat down on the toilet, dropped her skirt and panties to the floor and jerked off her own cock to relieve her painful arousal. After that, she simply cleaned herself up and came back to see Chris. He offered to do whatever she wanted him to do to her, but Wendy knew that she had to turn him down and that if he knew what she wanted and what she was really like then he might not be so forward in his offer. So instead she just went back to her dorm at the school where she told Danielle, who was full of eager questions, the majority of the details of her date. Despite not being on the receiving end of any sexual attention, Wendy was delighted after her date and was in very good spirits for some time afterwards.

***

Wendy continued to see Chris every weekend for the next few weeks. Each time their routine was the same as it had been on their first date, they would meet at the diner and have lunch before going back to Chris' place where his parents would be out for the day and they would rush up to his room where she would suck him off before retiring to the bathroom to relieve her own arousal. Every time they did this, Wendy felt herself becoming more and more of a woman and began to feel that even after graduating she could never go back to being Jason, never return to her boring life as a man. Every time she found herself desperately wanting more and Chris seemed to want her and to want to do to her whatever she wanted, but still she pulled back from it, ashamed of the terrible secret hanging between her legs.

When she was with Chris, Wendy felt every inch a gorgeous woman and all her desires were those of a normal woman, what she desired was Chris and his firm, hard cock between her soft lips. However, Wendy could not banish all of her remaining masculinity that easily and, besides her little secret beneath her skirt, there were other reminders that beneath the sexy schoolgirl uniform, girlie hair and make-up she was still a guy. Most of those reminders came in the form of her spending all day, every day in the company of nothing but sexy young girls in their skimpy schoolgirl uniform. Wendy hadn't been through enough of a transformation not to find herself a little excited by such company. More than anything, Wendy was increasingly finding herself attracted to her room-mate Danielle and this was the cause of many potentially embarrassing situations. Danielle was a very attractive girl, slender waisted and full breasted with long dark hair, dark mysterious eyes and a brilliant white smile. It would certainly not be out of the ordinary for a guy like Jason to develop a crush on such a great looking girl, but for Wendy it was the source of endless worries and confusion.

Besides, Wendy's growing infatuation with her room-mate was not limited to a purely physical attraction. Ever since she had arrived at Firwood at the beginning of the semester, Wendy had noticed how Danielle had gone out of her way to make her feel welcome. Danielle was always friendly and considerate and had a remarkable ability to almost always know what Wendy was thinking and feeling. Danielle was chatty and fun and she and Wendy had become almost inseperable best friends over the course of the few weeks that they had known each other. However, there was something even more than that. Wendy didn't know whether Danielle was deliberately being flirty or if that was just the way she was, but there was a very close, touchy-feely relationship between them. Danielle would often kiss Wendy on the cheek or hug her and hold her close, or she would hold Wendy's hand or lay her hand on Wendy's bare knee when they sat beside each other. All this physical contact made Wendy go flush with a moment of thrill and embarrassment and for all Danielle's ability to read Wendy's moods this was one thing she seemed not to notice.

Whenever Danielle came out of the shower and into the room that they shared together, her glistening wet body barely contained by the small towel, Wendy didn't know which way to look and would blush and try to arrange her hands so as to disguise the little tent in her blue and green plaid skirt. Once, Danielle had let the towel accidentally fall to the floor in front of Wendy. Wendy could only stare open mouthed at the beautiful perfect curve of her friend's naked breasts and the tuft of dark pubic hair pointing invitingly towards her pussy.

This was the image of Danielle that Wendy held in her head on the morning of the middle Friday of her first semester at Firwood. She was on her way to see Principal Stanton to discuss her progress in the first half of her first semester. Strangely, she didn't even think about her first meeting with her principal and the possibility that he might require the same thing of her again didn't occur to her, her mind was too much on Danielle. Although during their dates Wnedy was 100% devoted to Chris and willing to do anything for him, for the rest of the week her mind was all Danielle. In this confusing turmoil and conflict of sexual feelings and longings, Wendy's mind rarely touched on Principal Stanton.

"Come in Wendy," said her principal from behind his dark mahogany desk, she walked in and sat demurely in the chair he motioned towards, the same chair as before, "How has your first semester at Firwood been so far?"

Wendy assured him how much she was liking it, how much she was enjoying her classes and how much the other girls had made her feel welcome and at home, reserving special praise for Danielle. In fact, Wendy hadn't truly realised or appreciated until now how much she enjoyed being at Firwood. For the first time in her life she found herself to be genuinely happy at school and if her sexual desires sometimes damaged that then at least there was something to desire. Principal Stanton smiled to hear this and got up from his leather chair and walked around the desk to where Wendy was still sitting while talking to her.

"Since you're enjoying our school so much Wendy," he said, still smiling, "I assume that you will wish to continue to honour the agreement that I made with your mother," this last he said as he began to unzip his fly and it finally dawned on Wendy what she was really there for.

As her principal took his cock from his pants, Wendy slid from the chair to kneel in front of him. He wasn't as sexy as Chris but for a man of his age Charles Stanton was a very good looking guy and since their last experience Wendy had become even more of a girl so that now the thought of an attractive man's hard cock was a turn on for her. She had also had a lot of cocksucking practice with Chris over the past few weeks so she was now considerably more talented than she had been the last time with her principal. Wendy instantly began to put her new skills into action on her principal's cock, very quickly bringing his limp cock to a hard, erect state with the touch of her tongue and hand.

"You've been getting some practice," he said as she languidly teased the base of his cock with the feathery soft touch of her tongue, "What have you been doing in your exta-curricular time, Wendy?" he moaned with pleasure as she flicked her tongue over the head of his cock.

"I've got a boyfriend," Wendy said between licks of his cock, realising now she said it that that was what Chris had become for her.

Principal Stanton took his cock away from Wendy's lips, he looked angry and irritable, "Did I tell you you could get a boyfriend, that wasn't part of our agreement," he said, "I don't want to stick my cock the same place as some horny teenager. You're going to have to be punished for this," he went on as Wendy became a little worried, if he was really angry then he could reveal her secret to everyone, he could kick her out of the school, "Get up and bend over my desk."

He sounded firm and commanding and Wendy quickly obeyed, bending over the desk so she faced away from him, with her false breasts pressed against the desk and her ass thrust in the air so her short pleated blue and green plaid skirt rode up her ass to show a little of the virginal white silk panties she wore beneath. Quite violently, Principal Stanton pulled her skirt up so it fell down round her waist to reveal all of her pert panty clad ass. There was a moment of anticipation as Wendy wondered what was going to happen before her principal landed a hard slap across her ass that made her give a yelp of pain but at the same time, she was slightly embarrassed to note, her cock gave a twitch of excitement.

"You've been a bad girl Wendy, keeping secrets like this from me," Principal Stanton said as he spanked her ass once more.

Wendy expected him to continue spanking her little pert ass until it was raw but instead he stopped after the second time and began to feel her ass cheeks through the sensual silk of her white panties. He stopped for a moment, seeming thoughtful.

"Has your little boyfriend fucked your ass yet Wendy?" he asked, she didn't reply for a moment and he landed another slap on her ass, "Well, has he?"

"No," she replied with a whimper.

Although she was faced away from him, Wendy could almost feel Principal Stanton smile at this thought, "So if I were to plough in right now then I'd be the one to take your cherry Wendy."

Wendy felt a rush of confusing and differing emotions at that moment. She had really wanted to save her virginity to give to Chris or Danielle. However, at that moment her sex drive and her arousal seemed to outruling these ideals, her cock was becoming ever firmer at the thought of her principal's cock deep inside her. She desperately wanted it but then at the same time she was quite afraid that it would hurt terribly. She had heard that it hurt when ordinary girls lose their virginity and she didn't know how her little ass could ever take her prinicpal's cock inside it. Before she had much time to consider this, Principal Stanton had pulled her little virginal white panties down around her ankles to bare her ass to the world. He seemed excited and eager at the prospect of fucking one of his student's tight asses. He licked one of his fingers and inserted it up Wendy's anus. Wendy's ass clenched around the finger, it felt great up inside her and she groaned appreciatively at the feel of it. Soon her principal had shoved two fingers up inside her and her own cock was really hard now, rubbing against the mahogany desk. Principal Stanton took his two fingers out of her ass and she felt a disappointed sense of emptiness without them. Now, more than ever, she was desperate to have her ass filled.

Principal Stanton spat on his hands and rubbed the saliva over his cock to form some sort of lubricant but Wendy was still afraid that it wouldn't be nearly enough to allow his cock inside her tight anus. This fears weren't abated by the feel of his large, erect head pressing against her anus as he began to thrust it inside her. For a few minutes Wendy thought that she might pass out from the severe pain of it as she desperately tried to relax her ass to allow him inside her. Finally, her principal had forced the full length of his cock up into her ass so that his balls were almost touching hers. He waited for a moment as her ass became accustomed to the pain of his cock filling her before pulling almost all the way out. Partly involuntarily, Wendy found her ass rise up towards his cock, desperate to be filled again. Principal Stanton seemed happy to oblige as he thrusted back deep inside her much harder and faster this time.

Before long, anyone walking into the principal's office at that moment would have seen one of his sexy senior students bent over his desk with her skirt pulled up and her panties around her ankles while he, the principal, with his hands on her hips thrust rhythmically in and out of her tight virgin ass while she, obviously by now fully enjoying it, moaned and groaned and screamed with the highly pleasurable stimulation. Indeed, as her principal ploughed into her ass, taking her cherry, his balls slapping against hers, Wendy felt herself more and more turned on, her own cock, rubbing against the desk, was very close to a climax. Before Principal Stanton could reach his own orgasm, Wendy felt an electric thrill spreading out from her stimulated prostate throughout her body as her ass tightened further on her principal's cock and her own cock started uncontrollably ejaculating her milky white semen all over her principal's desk. The final stimulation of his sexy student's orgasm was enough for the principal as he too, with one final deep thrust that made Wendy's cock explode even more violently, began to fill her anus with sticky white juices. Wendy felt a warm, filling sensation in her ass and felt strangely elated by the whole experience, degrading though some people might find it she had found it exciting and arousing.

Still face down on the table, Wendy reached back behind her and used her fingers to scoop up some of the cum running down her thighs towards her white stockings and filling her anus. Making sure that her principal was paying full attention she turned her head so she was facing him and slowly and seductively licked her fingers clean of his cum. That wasn't all though, when she had stood up and was wanting to leave, Principal Stanton pointed out where she had cum herself and how there was a load of her cum on his desk. Obligingly, Wendy got down on her hands and knees and enticingly lapped up her own juices from the desk before she left to walk back to the dorm. As she walked out of the office, Wendy noticed to her pleasure that her principal was sporting another erection as a result of her sexy cum lapping and this time he wouldn't have her around to help him.

It was still winter and as Wendy walked back to the dorm dusk was already falling and the tree lined pathways and red brick buildings of the school's campus were already growing dimmer. As she walked back to her dorm Wendy thought about what had just happened. She had enjoyed the experience of having her virginity taken from her by her principal but now he was mostly forgotten and her mind returned to her usual feelings for Chris and Danielle and she began to think how great it would be if she could have that kind of experience with them but she quickly crushed that fantasy for fear of disappointment. The dorm was generally pretty empty when Wendy got back, on a Friday evening most of the girls liked to hang out in other places, but Danielle was there waiting for her when she got back to her room.

She was sitting on Wendy's bed with her head bowed and her dark hair falling over her eyes so she didn't see Wendy immediately when she came in. She wasn't doing anything, just sitting and waiting, she had a serious _expression on her face that worried Wendy just a little. She looked up as Wendy shut the door behind her and smiled at Wendy, it wasn't her usual cheery and friendly smile but something more low key, less cheerful but still warm and welcoming.

"Wendy we need to talk," she said...

To be continued

  

  

  

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