From: adietrech@aol.com (A Dietrech)
Newsgroups: alt.sex.stories
Subject: Story: Flipping Philp 1/2 (TG, femdom)
Date: 3 Dec 1994 09:40:03 -0500
FLIPPING PHILIP
Sybil Benwood and Mrs. Stark sat in the latter's car beside
the football field and watched Philip. He was an excellent player
and scored a couple of goals while they watched, a strong,
good-looking teenager with tousled brown hair and attractive grey
eyes.
"He's been spoiled rotten!" said his gandmother with
distaste. "He thinks because he's good looking and terribly
male that he can get away with anything...I suppose it would
be different if Elsie wasn't a single mother. She hasn't been
able to cope very well since Eric ran off with his
secretary six years ago. And Philip is the main problem."
"So I've heard," said Mrs. Stark in her deep voice.
She looked a little like Diana Riggs as Emma Peel in The
Avengers, only more buxom and muscular. She wore a severe black
suit and white blouse and her dark hair was cut short in a boyish
bob.
Mrs. Benwood looked like everybody's favorite grandmother but
with more steel in her. She was 63 and her hair was silver
colored but there was color in her cheeks and her voice was
strong and firm. She looked as if she would brook no nonsense
from anyone --- her high bridged nose was both arrogant and
elegant and she wore expensive clothes with style and was
obviously proud of her long legs and well-creamed complexion.
Sometimes she thought ruefully that her strong will
had taken too much away from her daughter Elsie who hated to
take a strong hand with anyone, including her husband and
children. At 38, she was a soft, tentative woman, attractive
enough but too eager to please. That was the trouble with
her and Philip --- she hadn't taken a strong hand with him.
"The trouble is Elsie has never disciplined the boy and he's
been in one scrape after another since he was ten. I hope
you'll be able to do something with him."
"We can but try," said Mrs. Stark. "Tall Pines has a
reputation for success. You can be sure we'll bring Philip into
line. I administer the discipline and my husband handles the
medical treatment..Give me another rundown on Philip's
history."
"Oh, he's always been rebellious! There was lying and
stealing when he was nine or ten...He seemed to start
thinking about sex early and his mother caught him masturbating
...I didn't know about this until fairly recently -- if I'd been
Elsie. I'd have taken a paddle to his bottom ! He seems to have
been keeping a dirty diary full of the most outrageous things
about his sister and his mother. And dirty magazines and books!"
Mrs. Stark gave a tight, close-lipped smile.
"There are aa lot of boys like that," she said thoughtfully.
"Sometimes the Old Nick can be whipped out of them by their
parents. Sometimes they come to us and we use a combination of
physical discipline, a changed environment and medical
treatment."
The two women fell silent and watched Philip. He was a
boy's boy who seemed completely at home among his male peers.
"I hope you can do something," said his grandmother. "The
situation is really serious now."
"Tell me about it."
Mrs. Benwood handed Mrs. Stark a pair of binoculars and
pointed to a woman standing by herself across the field, Mrs.
Stark took a long look. The woman was in her late 30's, rather
dumpy with a handkerchief tied around her head. She was
overweight with wide hips and her belly seemed to be bursting
through her camel's hair coat. Her pale face was vaguely pretty
but had an expression of startlement. Mrs. Stark handed the
glasses back.
"That's the boy's mother, my daughter," said Mrs.
Benwood.
"She looks pregnant."
"VERY pregnant! About seven months. Philip is
responsible.!'
Mrs. Stark looked suitably impressed.
"Quite a boy!"
"There's worse! His sister. Vinnie, is only 13. She's
pregnant too! Elsie doesn't dare let her out of the house
where tee neighbors can see her. It's a terrible disgrace!"
"I can see what you mean. Drastic measures have to be taken."
"If that boy was a tomcat I'd know what to do!"
his grandmother burst out fiercely.
Mrs. Stark laughed briefly.
"There's that," she agreed. "My husband sometimes has
performed the operation. But there are other techniques
which may work even better."
"I've heard that there's a treatment which turns a
boy into a girl without surgery if he's close enough to
puberty. Don't they call the end product 'she-males'?"
Mrs. Stark smiled cruelly.
"Oh, yes! That's Eben and my specialty and we've had a high
rate of success. We virtually guarantee that when a she-male
leaves our establishment she's dainty, well mannered and wears
her clothing perfectly."
"You mean they actually dress and act like girls?"
"Oh, yew! Sometimes, in extreme cases, they've been
castrated and rearranged. But there are more ways to castrate a
male than with the surgeon's knife. It can be chemical or in the
form of hormones. It depends on the boy.... About half the time
they retain most of their male characteristics while dressing and
acting like females. Occasionally, they decide to return to the
world of males completely."
"Would you and your husband be willing to take on my
grandson?"
"Yes. But it will be expensive and will take about two
years."
"I don't care! I'll pay for everything! Will a down
payment of $5,000 be alright?"
"That will be fine. But we'll have to get the permission of
his mother and she'll have to agree to what will happen."
"Don't worry about Elsie! She's half crazy now and is
worried that Philip will start after the twins. They're ten
now."
"Good. We'll arrange a meeting when convenient with Philip.
And you can meet my husband, Dr. Stark."
Mrs. benwood laid down the law with Elsie, telling her that
Philip simply had to go to a good boarding school where he would
get some discipline. She didn't go into the transformation that
was planned, though she hinted that wonderful changes were in
prospect.
Dr. and Mrs. Stark visited the Gordon home on a Sunday
afternoon and were introduced to little Vinnie who was cute as a
button even though she looked grotesque with her big, protruding
belly. The kid was developing little cone shaped breasts and hr
mother had put her into an "A" shaped maternity dress, only this
one was for kids and only came halfway down her long, skinny
thighs.
Dr. Ebenezer Stark was a tall, gangling man of about 40
without much of a chin and with prominent blue eyes. He wore a
light grey suit. Helen Stark fitted him somehow and they were an
excellent team, complementing each other perfectly. They soon
got to be quite at home with the various women of the Gordon and
Benwood households.
After awhile, Philip came in like a young, strutting tomcat.
He was wearing loose linen shorts and running shoes and was quite
a personality. He practically strutted when he saw his mom's and
sister's bellies, clearly knowing that he was responsible. He
had freckles and Mrs. Stark noted as she had at the football
field that he was all boy. Furthermore, he was an exhibitionist.
When he sat down in the parlor he crossed his muscular legs and
the loose shorts showed off a fine sized prick handing down his
left leg. His grandmother pursed her lips and looked
disapprovingly. Philip saw the disapproval but felt terribly
sure of himself. He grinned at his pregnant Mom, his
grandmother, his sister and the two visitors and dropped his hand
in his lap and squeezed the bulge openly. Pretty soon his cock
rose and stretched the pants obscenely. The boy's grin spread
from ear to ear.
"You're quite a fellow," Mrs. Stark purred while the boy
preened himself.
"Yes. Did you know that your mother and grandmother have
decided to send you to boarding school?" asked Dr. Stark.
"Is it a good school?"
"You'll like it. There are lots of sports there. But we
start with toning you down a little."
"What do you mean?"
"From now on no more loose shorts. You're going to wear a
jock strap like a pro athlete."
"Gee!"
Dr. Stark sat down on a straight chair and fished in his
briefcase, producing a brand new jockstrap. His wife stood
behind Philip and gripped him by the shoulders.
"Take off his clothes," she said. Mrs. Benwood, grinning
widely, moved forward and knelt in front of the boy. As soon as
he realized she was serious, he tried to pull away. Mrs. Stark
locked his arms behind him in a full nelson, and grandma stripped
him naked except for his running shoes. Realizing he was
helpless --- and that a WOMAN was stronger than he --- he lost
much of his self confidence and his cock no longer was hard but
long and limp.
"Bring him here," said Dr. Stark. His wife wrestled the boy
and the doctor slipped the jock over his shoes.
"Hey, that jock strap is too small!" Philip protested.
Dr. Stark smiled at him.
"Why yes," he said softly. "You're fifteen, aren't you?
When I went to the sporting goods store I asked them for a size
He began pulling the tight white elastic straps up the boy's
legs. Philip struggled but it was no use and even though the
garment was decidedly too small, especially for a boy with
Philip's outsized equipment, the job was done quickly. Helen
held him firmly while his grandmother worked the jockstrap up his
thighs, over his hips and then tucked in balls and prick.
Philip howled with pain, writhing and wriggling and weeping.
He had lost all his youthful male arrogance and his bravado.
Finally, he sagged limply, standing there miserably. He looked
like a different boy with the tight jock strap making his
equipment almost invisible.
"Would you bring in the boxes from my car," Dr. Stark asked
Mrs. Gordon and the plump mother hurried out to oblige. Mrs.
Benwood meanwhile went upstairs to Philip's bedroom and soon
returned with a cardboard box containing all of the boy's
underwear. Philip didn't understand what was happening and he
looked puzzled.
"What are you going to do?" he gulped, between sobs.
"You'll see!"
Helen Stark unpacked the boxes from the car, revealing
stacks of quite attractive girl's underwear while her husband
took the cardboard box from Mrs. Benwood and took it outside to
the barbecue pit in the back yard. He poured lighter fluid over
it and touched it off, the box of clothing blazed furiously and
everybody could see shorts, undershirts, male bikini briefs,
going up in flames.
"Why did you do that?" Elsie asked. "It's so destructive!"
"Philip's got to get used to the idea there's no turning
back. What he'll be wearing from now on is what we've brought
him."
Helen spread the lingerie out on the dining room table ---
wide legged French panties with lots of lace, bikini briefs in
silk, nylon teddies, garter belts, sheer stockings. Philip
struggled half heatedly but Helen put him into a pair of panties,
garter belt, shimmy and hose. With his tousled mop of boyish
hair and his freckles, he looked weird in that getup but he
became fairly acceptable when he was put into a pair of designer
slacks, hip-hugging and fitted, a sports shirt and saddle shoes.
It was clear that the Starks had been given accurate measurements
by Mrs. Benwood!
"Now you're going back to Tall Pines with us to start
boarding school," Mrs. Stark said. "While you're with us this is
the way you'll dress and you'll learn what it's like to be a
young lady. Who knows, you may get to like it!"
Dr. Stark chuckled and led the boy over to his own chair.
Philip was subdued.
"You'll get used to it," the doctor said. "From now on,
you're going to wear that all day every day and you can only take
it off when your mother or Aunt Elivira says. You'll soon find
you lusts remarkably reduced!"
"Please, Dr. Stark!" was Philip's only reply.
Shortly afterwards, Dr. and Mrs. Stark whisked Philip off to
High Pines for his new life. He found it was quite different
from what he had expected. In the first place not only did he
have to wear girl's underwear but he was soon put into skirts and
dresses. His hair grew long and was cut into a girlish style and
he had to wear hair ribbons, susan brown patent leather shoes and
white cotton ankle socks.
He also got a special diet and regular hormone and steroid
injections which basically changed his body chemistry. It took a
few months before he began to change considerably.
The High Pines Institute was divided into two parts, a
boarding school and a medical clinic. They shared a large estate
but were completely separate physically with sizeable dormitory,
mess hall and recreation area in between. There were about 20
young males and a similar number of females. A little more that
half the males were in process of transformation while the rest
were perfectly normal boys ranging from 14 to 18. The girls were
all girls, really a control group which could be used for
comparison purposes.
Boys being transformed were encouraged to develop close but
non-romantic friendships with girls their own age. When you
couldn't tell them apart, Helen and Eben felt their work was
successful.
Sybil Benwood was most interested in the routine and in the
methods used and when Eben and Helen found she was truly
sympathetic, they were quite open in their discussions and showed
her everything.
"It's naturally quite a shock when a boy is put into girl's
underwear and introduced into a foreign boarding school, cut off
from his friends and family. We allow him a day to think about
what may happen to let his imagination range. Usually, as in the
case of your grandson, he becomes rebellious in his thoughts...."
"Then he is summoned into my study and I give him the
standard lecture on what is expected of him and how he will be
treated. When I am finished, I ask him to take off all his
clothes. If he refuses, Helen strips him completely naked. Then
I bend him over a chair arm and give him a thorough thrashing on
the bum with a cane."
"They always howl a lot, even the toughest," Mrs. Stark said
with a grin of pure pleasure.
"Yes," said her husband with satisfaction. "The point is to
take away their self respect and pride and reduce them to
blubbering wretches. Afterwards, most of them ask what the
whipping was for because they hadn't done anything wrong."
"I tell them that the whipping is to remind them where they
are and what they can expect. Just a warning. Every week
they'll get a similar strapping or paddling. And any
misdemeanors between times will get similar treatment. You'd be
surprised at how quickly most of them get into line and promise
to be good. They usually try hard, but usually we can find some
indiscretion which enables us to bring out the rod."
"Don't you think you are being . . . excessive?" Sybil
asked. She was appalled yet sickly fascinated.
"Not at all," said Dr. Stark. "We have to break their
spirit right at the start and keep them frightened. If we do it
right, they obey every order at the jump."
The medical treatment started on the third day with a
thorough checkup to see that the boys were healthy. Then Philip
was given a combined hormone and steroid shot and put on an
enriched diet. Mrs. Benwood and her daughter were on hand and
they saw everything was handled perfectly -- the medications
nurse didn't even hurt the boy when she put the needle into his
skinny ass.
It took quite awhile for the effects to show. At first,
Philip went to school in slacks, runners and tee shirts just as
he had before except that he wore ordinary cotton panties and
undershirts almost indistinguishable from those of the "real
boys" he had known.
Sybil usually was present when Philip got his first
injection of the week and she was always very sympathetic,
holding his hand and often kissing him affectionately. He got
very close to her, especially because he had been cut off from
everybody else.
After a few weeks, the effects of the treatment began to
show a little bit -- Phil's hips began to widen and soften, his
thighs began to fill out, his skin got softer, his bosom began to
swell a little.
In the mess hall, he discovered there were other boys like
him who were developing swaying walks and whose voices were
rising instead of deepening. With these boys he sat in classes
involving dress, make-up and deportment. At first it seemed
strange but as he got more physically feminine, his mind told him
it was perfectly natural. He had little difficulty in slipping
into nylon or silk panties with lace, or learning how to handle
lipstick, or how much perfume to dab in his armpits.
Unlike home, Phil was not discourage from jerking off -- in
fact, masturbation was encouraged in the dormitory and every
night was filled with panting, rustling and creaking or springs
as lonely, horny boys found solace with their own penises. In
the first two terms, however, no mutual masturbation was
permitted and boys who tried it were severely punished and
humiliated. Like Philip, other first termers had to wear overly
tight jock straps which they were permitted to remove at night.
Under constant restriction, their balls shrank and their pricks
too, although they remained of respectable length --- plenty was
left to play with. Sybil examined her grandson regularly and
noted the progress with his balls and prick with approval. When
he came home for Christmas, Elsie was shocked to find what had
happened to her boy and though she had had very serious
misgivings about her pregnancy, she still loved Philip dearly
(and sexually). She took him into her bed and babied him,
including playing with his new cock. In spite of the treatments,
he was still horny enough and got a good hard-on which his mother
enjoyed putting into her though she took no chances and made him
wear a condom. She also wouldn't let him fuck his sister on the
grounds that she didn't want another accident to happen.
By this time both babies had been born without any
difficulties --- Vinnie produced a bouncing boy and Elsie a girl,
both healthy and pretty. Vinnie, now 13, was delighted to have a
real live doll to play with. Her mother supplied milk for both
babies because Vinnie's breasts were not yet quite adequate,
though the new cones produced a little milk and she loved having
her nipples sucked.
When Philip returned to High Pines he was moving into the
next stage of his metamorphosis. Gradually, over the weeks, he
stopped wearing slacks and shirts and runners and began wearing
dresses and strap shoes. Sybil and Elsie marvelled at how wide
his hips were getting and how full his upper thighs. At the
start of the second year he had his first breast implant. The
hormones had done wonders and he had real breast already, though
they were rather small. A combination of growth salve and
steroids increased the size of his nipples and aureoles until
they were quite respectable. Dr. Stark's cosmetic surgeon then
implanted silicon pads that gave him a 34 inch bust.
"Later, we'll have another operation to give you 39 inch
breasts but right now you have to get used to your new beauty,"
the doctor said.
When it was time to show of the product, Philip posed before
a full length mirror wearing his jock strap, a spandex pair of
bikini briefs, garter belt, stockings and high heels.
"You look gorgeous, Philip!" his grandmother said.
Like any human being, Philip revelled in applause and
admirations. He knew he wa pretty in a female way and he like
what he saw but he still thought of himself as a boy and when he
looked again he was shocked at the "girl" he saw in the mirror.
It was hard to say when he started thinking of himself as a girl
and surely the sensation didn't last all the time. Quite often
he would leaf through his old snapshot album and mourn the tousle
headed boy with the infectious grin who was kicking a football or
riding a bike or standing on the diving board. His tears were
real even as he delighted in rubbing his thighs together with a
rustle of nylon. He knew there was no use protesting and Dr.
Stark and Mrs. Stark and his grandmother all told him frequently
that the best thing he could do was to learn how to be a
beautiful girl as quickly as possible. There were other
incentives: if he (or any of his classmates failed a make-up
test, or chose the wrong color combination, or had crooked seams,
the strap came out and was used painfully on a bare rump.
Brought up in boyhood's stoical hero tradition to stand up to
pain bravely, Helen Stark soon broke him utterly so that shame
replaced pride. He dreaded the long and public ritual or
punishment which made sure the victim was completely shamed as
well as punished. He got so that he would start whimpering at
the sight of the hairbrush or the strap and would howl and weep
and plead with his tormenter from the first stroke -- much to the
delight of his prurient audience.
So Philip learned how to dress as a girl, how to use make-
up, how to walk on high heels, how to pitch his voice and behave
toward adults. There was a charming shyness and timidity about
him that his grandmother remarked on and thoroughly approved.
Whereas most real girls as pretty as Phil would have revelled in
attention and flirted with every male, Phil hung back shyly and
talked very little. Some men found this charming and put
themselves out to attract the lovely creature.
None of the new "girls" from High Pines was allowed to wear
teenage fashions -- they were all dressed rather primly in out of
date styles and had to behave decorously. Faced with serious
punishment, they accepted their role and found the outside world
found them rather unusual but no less attractive and sexy for
that.
In spite of a few early storms, the transformation went on
without many setbacks. Female hormones and other drugs did a
great deal to make Phyllis forget that she had once been a boy
called Philip. Surrounded by she-males in the same position and
by unrelenting teachers and nurses, Phyllis began to adjust to
the female role at a gratifying rate. Sybil was delighted with
her new granddaughter. Elsie and Vinnie were preoccupied with
their new babies and accepted Phil/Phyllis abstractedly. When
Phyllis completed the two year program he/she was 17 but a very
young and innocent teenager, much more like a girl of 15.
Although the second transplants gave Phyllis a 37 inch bust,
Helen Stark kept the boy/girl in adolescent clothes -- short
skirts that showed off long, bare legs, Mary Jane shoes, gingham
tunics and big hair ribbons.
Mrs. Benwood kept an 8X11 photo of Philip as a 15 year old
football player in shorts and jersey and tousled hair to compare
with the soft hipped, full breasted granddaughter she now had...
************
I met Sybil Benwood at a convention where we were delegates.
She was on the board of High Pines School and was a strong
spokesperson for great discipline in the education system. I
found this arrogant old woman with the aquiline nose and erect
carriage was very exciting and I let her know it. She responded
favorably and we soon became fast friends. When she invited me
out to her mansion, I was introduced to her daughter Elsie and
Elsie's two cute teenage daughters, Vinnie and Phyllis, both of
them seemed to be about 15. Elsie had twin baby sons as well,
nearly two years old
The teenage girls were most intriguing and were not really
much alike though they were dressed similarly and their manner
was rather innocent and shy. Vinnie was slim and pretty yet with
a knowing look about her as if she'd had sexual experiences.
Phyllis was bigger and taller with real muscles. She had a
remarkable bosom for a young girl and lovely wide hips. I like
her coquettish smile and soft, husky voice. She was obviously
the great favorite of her grandmother, who often called her over
and petted and talked sweetly to her. Phyllis practically
purred...
By this time I was hot to trot for Sybil. I knew she was 65
-- she fully looked her age with a handsome, wrinkled face and a
halo of beautiful white hair. A lot of people wouldn't have
thought she was sexy but I did. I courted her ardently, dating
her, bringing her presents, paying her compliments. Within a few
weeks she was prepared to kiss me and soon we were smooching all
over the place. When she fell for me, she fell with a vengeance
and didn't hold back. I loved going to bed with her and I told
her all the reasons why I thought old women were more delightful
than young women.
At the same time, she told me the story of Philip/Phyllis
and his extraordinary transformation, and of his two children
with his mother and sister.
"Do you know, this is the most wonderful success story I've
ever seen," Sybil gushed as she brushed her man before bed. "I
never would have believed that rascal Philip would turn into such
a successful girl! She's a perfect coquette and all the boys
around are mad about her."
"No feelings of guilt?" I asked.
Sybil smiled.
"Not a bit of it!" she said triumphantly. "Phyllis is my
triumph! She'll have a wonderful life as a girl!"
I went over and kissed her on the wrinkled cheek.
"Come to bed, darling," I whispered.
Sybil stood up and followed me to the big double bed.
"Do you know, I think I'll marry Elsie off to someone," she
said. "Now that Phyllis is no longer a problem, I should do
something for her mother!"
"Yes, dear," I said, putting my arms around her and pulling
her close so that my rising cock pressed into her soft asscheek.
She squirmed happily.
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