Crystal's StorySite storysite.org |
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
*********************************************
© 2005 by Jessica Swift. All Rights Reserved. These documents (including, without limitation, all
articles, text, images, logos, and compilation design) may be printed for personal use only. No
portion of these documents may be stored electronically, distributed electronically, or
otherwise made available without the express written consent of StorySite and the copyright holder.