Newsgroups: alt.sex.stories
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 10. I want you to know you're wearing this one."
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.