Joyce Francis Brookes was a pretty boy with long blonde hair, pale blue eyes and delicate features. He was painfully aware of how feminine he looked and tried to mask his appearance by acting butch, but the act wasn't very convincing and sometimes people thought he was a girl and called him 'Miss' by mistake.
It made him very uncomfortable.
He was only 14 when his parents died in a car accident and his aunt Katherine came to look after him.
Katherine was a tall, voluptuous woman in her mid-thirties, with long black hair and emerald green eyes, who bitterly resented the fact that Joyce (a spoiled, petulant child) stood to inherit the bulk of her dead brother's estate ($32,000,000.00) while she got almost nothing for raising him; just fifty grand when he turned eighteen.
It didn't seem fair.
Her brother had always been a cheap bastard. And now his son would have to pay for that. Yes, she decided, she'd turn him into the very thing her brother would have hated. And that would be her revenge on him and all the other rotten bastards in the world…
A stronger boy might have been able to resist her plans, but Joyce was too small and delicate to fight back and felt trapped by the will of this dominating woman who always loomed above him larger than life.
And it only seemed to get worse as he grew older.
Katherine still spanked him like a little boy whenever he did something wrong. And even though he was nearly 15, she pulled down his pants, and made him climb across her knees, and paddled his ass while he kicked and squirmed until his little bottom turned bright pink.
And since it seemed like he was frequently bad she decided she had no choice but to teach him to behave in a more appropriate fashion.
It was a lesson Joyce would never forget.
She took him into a trendy girl's clothing store filled with pretty skirts and tops, little bras and panties.
"Aren't these just the cutest clothes?"
"Yeah, I guess… for a girl," he shrugged.
"I bet you'd look adorable in this."
She held up a short pink pleated dress.
"W-what do you m-mean..."
"I mean, you're small and pretty enough to be a girl. Why don't you give it a try?"
"No, that's okay…"
"C'mon, let's see how you look."
"Don't argue with me, dear. Or I'll spank you right here in front of everyone. Do you want that, darling?"
"No, I'm sorry."
"Then do what you're told."
So he looked at a dozen different dresses before he finally selected a tight blue sequined dress with thin spaghetti straps.
"That's very pretty."
The sales girl giggled when he brought it to the counter.
"Is it for your?"
Joyce blushed but didn't answer.
"Don't be shy," Katherine prompted.
"Yes, I guess so…" he stammered.
"Well, it's very nice," the sales girl smiled. "But don't you think it's maybe just a little bit too grown up for her?"
"Do you really think so?"
"Oh, yes, I bet she'd look absolutely precious in something cute and frilly with ribbons and bows like this…" She held up a frilly white dress with a short ruffled hem and a white satin bow that flounced down in back, more suitable for a child than a teenage girl.
"Why don't you try it on, sweetheart?"
"What?" he gasped.
"C'mon," the salesgirl smiled. "It'll be fun."
"But what if somebody comes in?"
"They'll just think you're a pretty little girl." Katherine smacked him lightly on the bottom. "Now scoot!"
Joyce disappeared into the dressing room, and when he emerged a few minutes later he was wearing a little white frou-frou dress with big puffy translucent sleeves and pearly pink buttons that ran down the back.
"I don't know," said Katherine. "What do you think?"
The salesgirl walked over to where Joyce was standing in front of a mirror and looked at him critically.
"She's a little bit overweight."
Joyce was mortified. They were standing there, talking about him, using words like 'she' and 'her', as if he wasn't a boy anymore.
"Turn around, honey. Now raise your arms…"
He did as he was told and then he heard the women laughing.
"Oh, sweetheart," Katherine squeezed his bare behind. "You forgot to put on your panties!"
The sound of their derisive laughter made him blush.
"Such a naughty girl!"
She pulled down his dress. Then she turned to the shop girl and said, "We'll take it. Don't bother to wrap it. She'll wear it home."
"But Aunt Katherine!"
"And if I hear another word, young lady, you're going to be very sorry. Do you understand me?"
"Yes," he nodded helplessly.
"That's better," she said. "Now come along, honey."
"I hope she likes it," the salesgirl smirked.
"Say, thank you, Joyce."
"T-thank you," he replied in a halting voice.
Then they left the store, and Joyce was forced to walk through the mall in this awful little dress that clung tightly to his waist and fluttered loosely at his thighs. Several people stopped and stared at him. Then to his consternation, he saw his classmate, Tina Carrington, coming in their direction. He tried to look the other way, but she saw him and smiled, "Hello, Joyce."
"Hi, Tina," he murmured.
"I almost didn't recognize you."
"I was, uh…"
"Shopping for a new dress," said Katherine. "How do you like it?"
"Well," Tina looked at him with obvious delight. "It's very nice. But I think he'd look really sweet in pink."
"Do you really think so?"
"Yeah," Tina insisted. "Pink."
"I think you may be right," his aunt nodded. "What do you think, Joyce?"
"I don't wanna wear prink or any other color dress," he complained. "I'm not a girl."
"Maybe you'd prefer to wear diapers," Katherine murmured.
"No, th-thank you," he stuttered. "That's ok-k-k-ay."
"Yes, I can see it might be easier to handle you in diapers like a baby," she laughed. "Well, say goodbye to your girlfriend, dear."
"Bye, Tina," he tried to smile.
"Bye-bye, Joyce. I'll see you at school," she waved to him. "Bye, Ms. Cross."
Joyce was nearly in tears by the time they reached the car. He crawled into the front seat and locked the door.
"Sit up straight, dear," Katherine told him as they drove back to the house. "That's right, darling. Lift up your chest. Now practice that until we get home, and don't say a word."
Joyce did as he was told. But when he got home he raced inside the house and started to cry.
Katherine discovered him sobbing on the floor.
"What's the matter, darling?"
"I don't wanna be a girl!" He buried his face in his hands and began to whimper.
"Don't worry," Katherine smiled. "You'll get used to it."
"No… no…" his shoulders sagged.
"You look very pretty, darling. Now get up, blow your nose, and take a good look at yourself."
In the mirror he saw a teenage girl with long blonde hair and a pretty face dressed like a child in a short white party dress and white patent leather shoes.
"Just remember how silly you looked, standing there, showing us your big soft behind," she whispered in his ear. "I swear, you're starting to jiggle, dear." She kissed him slowly on the neck. "I think you really need a bra…"
"Please… don't make me…"
"I know you must be exhausted, dear, it's been a very trying day, so I put out something pretty for you to wear when you take your nap. It's on the bed. I hope you like it, darling."
"But Aunt Katherine… it's only four o'clock in the afternoon!"
"Didn't you hear me?" she frowned. "I want you to go to your room this instant, young lady!"
And so Joyce Francis Brookes, a boy of nearly 15, was sent to bed that afternoon, wearing a short pink nightie with puffy sleeves and bows that his aunt, Katherine, made him wear, and he cried himself to sleep.
After that nothing was ever the same.
* * * *
Tina Carrington told all the kids at school that she'd seen him in the mall wearing a dress. The boys laughed. The girls giggled. And everybody called him, sissy.
Mortified, Joyce ran home and hid in the house.
"Well, then you can help me clean the kitchen."
Katherine handed him a broom.
She didn't like the way he did it, so she told him to take off his clothes.
"What d-d-do you mean?"
"Just do what your told."
Nervously, he took off his shirt and pants and stood there blushing in a pair of pink nylon panties that she made him wear to remind him of his weakened, effeminate condition. Then she handed him a gauzy white ruffled apron and told him to put it on.
"Now," she sat down on a chair and patted her knees. "Lie down across my lap."
His aunt wore a sheer white blouse and a tight black knee-length skirt. Through the blouse Joyce could see the black impression of her bra and the shape of her breasts pressing against the flimsy fabric.
"Why do I have to?" he whined like a child. "I didn't do nuthin' wrong."
"Yes, you did," she insisted. "Now do what your told!"
And so, reluctantly, he crawled across her lap and lay there in his ruffled apron with his frilly panties exposed.
"Don't you look cute!" she laughed and ran the palm of her hand over his pink satin-clad bottom. Then she placed her fingers inside the elastic waistband of his panties and pulled them down around his thighs, exposing his girlish ass, and spanked him while he sniveled and sobbed and begged her not to hit him anymore!
"Do you promise to be a good little girl?"
"Yes…" he whimpered.
"Yes, I'll be a good little girl…"
"And do you promise to always wear panties?"
"Yes, Aunt Katherine."
She rubbed cold cream on his quivering bottom.
"I'm not going to spank you anymore."
"Th-th-thank you, Aunt Katherine…"
"Doesn't that feel nice?"
She pressed her finger against his tightly puckered asshole.
"No!" Joyce began to protest. But then to his utter shame and despair he found he had an erection!
"My my my…" his aunt chuckled and squeezed his little pee-pee. "What do we have here?"
"Stop!" Joyce cried. Then he started to ejaculate.
"Oh, dear," Katherine frowned. "Baby made a little mess."
"I'm sorry…" he sobbed.
"From now on, Joyce, if you can't control yourself… I'm going to have to make you wear diapers and plastic panties. Do you hear me, dear?"
"Yes, Aunt Katherine," he nodded, tearfully.
"And you're way too big for that," she smiled, happily.
* * * *
That Halloween, Joyce was dressed as a little girl in a short pink dress with a ruffled bodice, sheer puffy sleeves, and pink translucent buttons running down the back. Stiff white petticoats rustled beneath the hem of his dress whenever he moved around the room in his pink and white saddle shoes. His curly blonde hair was now in two pigtails tied with ribbons of the same intoxicating color. The pale, shimmering tint enhanced the rosy blush of his pretty cheeks.
Looking at him, Katherine smiled. She had no doubt that all the boys would just love to play with her little Joyce.
"You do like it, don't you, dear?"
At first, Joyce had objected to wearing such a baby-like outfit. But Katherine had insisted.
"Yes, auntie," he answered, doing his best to smile.
"You look beautiful," she whispered softly in his ear.
"But I feel ridiculous…" he squirmed. "Why do people have to see me like this?"
"Why not?" Katherine smiled.
"Because I'm not a little girl!" Joyce closed his eyes. "I'm a boy! And I'm nearly 15 years old!"
"Oh, sweetie!" His aunt kissed him on the cheek. "Do you think anybody really cares?" she laughed. "They just like you the way you are. Everybody likes you the way you are."
Katherine winked and left the room.
After she was gone, Joyce took another peek in the mirror. He sighed at what he saw: a pretty teenage girl with large blue eyes and long blonde hair, nearly smothered in ruffles and lace.
He was encased in a starched pink dress trimmed with pretty eyelets and bows, hundreds of flounces, a soft nebulous cloud with puffy sleeves and a frilly bodice designed to flatter his bust line, taper his waist and accentuate his hips. His long blonde hair was carefully curled in elaborate golden ringlets. His waist had been cinched, face powdered, eyebrows plucked. His lips were petulant, painted red and gleaming. With a cluster of white pearls depending from each dainty earlobe, even Joyce had to admit, he made an adorable little girl.
"How could I let her dress me like this?" he cried out loud. "How could I be so weak? I should have said, no, I won't wear it! I'm a boy… not a girl!"
Yes, that would have been the appropriate response. But of course he didn't say it. And now it was too late for that.
Just then his nanny, Mrs. Trowbridge, entered the room.
"Oh, Mrs. Trowbridge," he cried bitterly. "I look like a baby dressed up in these clothes. Why do I have to wear such a ridiculous outfit?"
Mrs. Trowbridge was a towering figure, over six feet tall, with a strong bosom, powerful hips and thighs, dressed in a gray uniform.
"Your aunt wants you to look beautiful," Mrs. Trowbridge said. "Now go downstairs. Everyone is waiting for you to make your grand entrance. So run along, precious, and remember to smile. We don't want to have people thinking you're a reluctant hostess, now, do we?"
"No, I'm sorry, Mrs. Trowbridge." Joyce lifted his chin and smiled obediently. But he was terrified.
How could he stand in front of all those people looking like a little girl in a short ruffled dress and petticoats?
"Wait, Mrs. Trowbridge, wait!"
"Not now," she grabbed him by the arm.
"But I have to go pee-pee!" he shrieked.
"Too bad," she grunted.
"No, please!" he whimpered. "Please!"
Mrs. Trowbridge pushed him down the stairs while he struggled to escape, but she was too strong for him and there was nothing he could do about it, though he tried his best to resist her. She dragged him through the hall and then shoved him into the dining room where all of the guests were gathered.
Everybody turned when he stumbled in the room. And, at first glance, they saw what appeared to be a pretty little girl, like a fairy princess, in a frilly pink dress with flouncy petticoats and a big satin bow tied behind her slender waist, just standing there, frozen, in the middle of the room, her eyes very wide.
Then Katherine started to laugh.
"This is my nephew, Joyce, everybody. He said he wanted to be a little princess for Halloween and I agreed. Doesn't he look adorable?"
Joyce blushed furiously, grabbed the hem of his party dress and tried to flee. But he tripped over his own feet and toppled down. His dress flew up, revealing his pretty ruffled panties and a little bulge between his legs that made it abundantly clear to everyone that he wasn't a little girl at all.
"He's almost fifteen," she announced to her guests. "But as you can see he prefers to be treated like a baby."
The people at the table started to laugh.
Then with a little shriek of despair, Joyce turned and fled from the dining room and ran back upstairs to his dainty bedroom where he slammed the door and threw himself across his pink ruffled canopy bed and began to cry. It was horrible! He hated her… and he hated the way his petticoats rustled when he squirmed on the bed. It made him feel so terribly weak and vulnerable.
"Are you okay?" said a masculine voice.
Joyce looked over his shoulder and saw his older cousin, Roger Wilcock Smith, standing by the bed. Roger was a tall, handsome young man with thick sandy brown hair and a confident manner.
He was everything Joyce wanted to be… but couldn't be.
Roger was muscular, tough, and hard.
While Joyce was timid, soft, and puny.
"Oh, Roger, I'm so ashamed…" he buried his face in his hands and started to sob. "I feel so ridiculous!"
"Why? You look very pretty, Joyce."
"But I don't want to be pretty!"
"You should never be ashamed of what you are." Roger sat down beside his pretty cousin, put his hand under his delicate chin, and tilted up his face to get a better look at him. He couldn't believe that this effeminate creature was actually a boy just a couple years younger than he was.
Joyce's eyebrows had been plucked and thinned. His eyes were very blue. His nose was small and slightly upturned. His lips were plush, seductive, and painted red. If it weren't for the pigtails and the party dress, he would have made a very sexy teenage girl.
"I think you look great."
He slipped his hand around Joyce's waist and then gently squeezed his thigh.
"Oh, Roger don't," Joyce murmured in a soft, well-modulated voice. "I'm not a girl… really… I'm not!"
"Don't be such baby…" Roger squeezed a little harder.
For a moment Joyce wondered what would it feel like to be crushed in Roger's arms, to have Roger's lips kissing him, Roger's tongue inside his mouth…
Then Joyce's face grew very red.
Whatever in the world was he thinking?
"Lie down… relax…" Roger pushed him back upon the bed.
"Please don't…" Joyce lay on his back, totally petrified and passive. His soft blue eyes filled with tears, but he didn't struggle or try to resist. Slowly, Roger unbuttoned Joyce's dress and reached inside the ruffled bodice and fondled his cousin's budding breasts.
"Oh… oh…" Joyce moaned.
"You like it don't you?" Roger ripped the bodice down, exposing Joyce's soft white bosom and pinkish nipples. "Oh, yeah!" he grinned.
"Shut up," Roger smiled. Then he lifted his pretty cousin up and rolled him over on his belly. Then he yanked up his dress revealing pink ruffled panties and a big quivering behind.
"No, I don't want to!" Joyce tried to get away.
But Roger twisted his arm behind his back and forced him to lie there. At the same time he grabbed the elastic waistband of Joyce's satin panties and pulled them down around his pretty thighs. Then he mounted his trembling cousin from behind.
"Stop!" Joyce struggled and cried. "No, please don't!"
"Baby's got a big fat ass!" he chortled.
"Oh oh oh!" Joyce whimpered in pain at first, but then, after a while, as Roger continued to work his thick tool back and forth inside him he began to accept the steady thrusting motion of the penis deep inside his ass, he started to pant and moan and move his hips back and forth like a woman whimpering in a high-pitched voice, "Oh Roger… oh Roger… oh Roger!"
That's when Katherine came into the room and caught them in the middle of the act.
"What the hell is going on here?" she exploded.
Roger jumped up and grabbed his pants, while Joyce cowered beneath the pink cambric sheets.
"I can explain everything…" Roger began.
"There's no excuse for behavior like this," she told the strapping young man. "Go downstairs, Roger, and wait for me there. I want to talk to Joyce, alone."
"Yes, Miss Brookes," Roger zipped up his pants and fled the room.
Katherine looked down at her frightened nephew without speaking for a long time. Then she said, "I'm very disappointed in you, Joyce."
"I'm sorry…" he whimpered softly.
"Do you want to be known as the kind of girl who drops her panties for every boy that comes along? Is that the kind of girl you want to be? Answer me!"
She slapped him hard across the cheek.
"Do you want to be known as a stupid little slut? Is that what you want?"
"No, auntie, no!" Joyce cried hysterically.
"Now take off your clothes," she told him. "And lie across my lap."
"Please, don't make me, please, I promise, I'll be good!"
"I don't understand," Katherine looked into his watery blue eyes. "First you say you don't want to wear a dress. Now you don't want to take it off. Which is it, Joyce?"
"But, auntie…" he blubbered. "I'm nearly 15."
"Well, I've seen your little pee-pee before," she smiled grimly. "And I know it's rather small. So don't be embarrassed, dear. Now take off your dress."
And so Joyce reluctantly removed his frilly party dress, stiff white petticoats and ruffled panties. He was painfully aware as he stood there, totally nude before his aunt's critical gaze, just how soft and hairless he appeared to be for a boy of nearly fifteen.
"Now lie down across my lap, dear. That's right." She picked up a bottle of baby oil that was lying on night table by the bed and squirted the clear lubricant into the crack of her nephew's ass and told him to raise his behind.
"But why?" he whimpered, pitifully.
"I have to make sure he didn't hurt you, dear." Then she put her finger into his asshole and moved it back and forth. "Your little hole is bloody, dear. Is it painful?"
"Yes," he nodded shyly.
"That's what always happens the first time a girl gets her cherry popped. Did he wear a rubber, Joyce? Did he at least do that?"
"I think so…" the boy mumbled abjectly.
"Well, thank God for small favors," Katherine replied. "A pretty girl has to be very careful these days. I hope you realize that, Joyce."
"But I'm not a girl!" he cried pathetically.
"Ah, well, you keep saying that, Joyce. But you seem to confused. Didn't I just catch you in bed with a boy? And wasn't he using you like he'd use a girl?"
"But he raped me!"
"Well, you seemed to be enjoying it when I came in." Katherine slowly worked her finger back and forth, probing deeper into his ass. "In fact, you seem to be enjoying it right now."
"No… no!" he cried when she reached around and grabbed his little pee-pee. As soon as her fingers closed around the head of his rigid penis, he ejaculated.
"See what I mean, darling?"
She squeezed the last few drops of semen from the tip of his tiny organ and rubbed the gooey cream on his lips.
"You're such a dirty girl!"
* * * *
The next day Katherine sat her nephew down and told him in no uncertain terms that he had a very serious problem and needed to see a psychiatrist.
Joyce sat in a big high-backed chair and listened to her with his head down and his knees pressed tightly together. He wore a pair of tight blue denim shorts and a sleeveless white cotton blouse that tied in a knot above his mid-riff.
"Do you really think so?" He played nervously with a strand of long blonde hair.
"I'm afraid so," she nodded sadly. "It's obvious to me that you've formed an unhealthy attachment to your pretty skirts and dresses. I suppose it's my fault to some degree. I should have seen you were having a hard time adjusting to adolescence. But it's not too late. I know a good doctor who can help you overcome your sexual problems…"
And so it was that Joyce was shipped off to a private sanitarium run by a German psychiatrist named Dr. Matilda Braun.
Dr. Braun was a towering woman with enormous breasts, powerful thighs, short brown hair, in a tight black skirt, high heels, and a white lab coat. Her face was oddly smooth and tight from several face-lifts. As a result it was hard to gauge how old she was. But 45 seemed about right.
"Tell me what seems to be bothering you, Joyce?"
"I don't know where to begin…"
"Well, tell me how you started dressing up."
"You mean the first time?"
"Yes, let's begin with that," said Dr. Braun.
"I was a little boy, like six years old, and there was this girl named Jody. We were about the same age, but she was a lot bigger and stronger than me, and she liked to tease me and push me around, and then one day she forced me into a dress. It was so embarrassing. I was totally mortified, and yet, on some level, I have to admit, I liked it, on some level, I was incredibly excited.
"After that I started dressing up in my mother's clothes and then in things I found in trash cans… like a pale blue one piece bathing suit that somebody threw away. It made me feel, I don't know… sexy, I guess. But now, I wanna stop because… I wanna be normal."
"Yes, I see," she nodded sagely. "You seem to have some real gender-identity problems. But I feel confident that we can work them out, together, if you're willing to try. What do you say, Joyce?"
"Yes, I'd like that, Matilda," he nodded.
"No, no, Joyce, you have to call me Dr. Braun. It's a professional relationship. I'm your psychiatrist. And you are my patient, Joyce Francis Brookes, a shy effeminate boy who likes to wear dresses. You have to learn to understand and accept your role in the psychiatric process, and if you do, I'm sure I'll be able to help you with your sexual problems. Is that clear?"
"Yes, Dr. Braun." He tried to speak up but his voice sounded like a whisper. "I'll try my best."
"There's only one way to deal with this kind of problem, dear. You have to face it. Do you hear me, Joyce? You have to learn to embrace your fears. Only then can you ever be free of them, until then, you're in denial."
"What do you mean?"
"I mean I intend to take you back to the very first time you were ever dressed like a little girl and make you go through the whole experience again, do you understand me, Joyce? I'm going to make you confront your fears. I'm going to make you embrace those pent-up feelings. Right now, you're fighting your feminine self. But you have to understand that part of your personality if you want to be free of your sexual problems. Do you think you're strong enough to do that?"
"I think so, Dr. Braun."
"I hope so for your sake, Joyce. I can feel your sadness, your desperation, your loneliness. I want to help you to realize your true potential. I want to help you learn how to love yourself. Do you understand me, dear?" She looked at him across a desk piled high with medical books and papers. "You have to trust me, Joyce. You have to do exactly what I say, no matter how strange it may seem to you at the time. Everything I do is done for a reason. To help you get better. And the only way to do that is to take you back to the root of your problem. From now on, when you're alone in bed, I want you to play with your nipples and your breast and say to yourself, I'm a sexy girl, I'm a sexy sexy girl. Will you do that for me, Joyce?"
"Well, I don't know, I mean, how is that gonna make me get any better?" he mumbled.
"I am your doctor. I know what's best. If you're going to fight me, Joyce, if you're going to resist your therapy then we may as well not even begin. It's all or nothing, Joyce. Suit yourself."
Dr. Matilda Braun sat in a big leather chair. She looked at Joyce huddled on a little stool with his knees pressed together. He looked small, pretty and very scared, dressed a pair of girlish black stretch pants and a little black fuzzy angora midriff sweater-top that showed off his narrow waist and belly.
Her expression was stern.
"It's up to you."
"Well, okay," he hesitated. "I'll try to do what you say, Dr. Braun, but it's going to make me feel… strange."
"I want you to feel strange, Joyce. The stranger you feel the better. That's how we know you're really confronting your problems. If you didn't feel uncomfortable, the therapy wouldn't be of any real or lasting value." She smiled and looked at her watch. "Our time's up for the moment, Joyce. But I'll see you again in a few days. Until then I want you be a good little girl."
"Are you sure about this?" he licked his lips.
"Yes, I'm sure," she snapped. "Do you want to be cured of your condition or not?"
"All right," he sighed, uncertainly.
* * * *
Dr. Braun surrounded herself with a group of tall blonde powerful Nordic nurses clad in tight white uniforms.
The nurses dressed him in decidedly childish, feminine clothes; pretty little jumpers and pinafores and petticoats and panties with lots of lacy flounces on the bottom. They taught him how to walk with his back arched, his chest lifted and his big bottom pushed out; how to move his hips in such a way that it would accentuate the motion of his large, bouncing behind. Then they made him stand in front of a mirror for several hours and contemplate his girlish condition.
In private therapy sessions with Dr. Braun, Joyce confessed to being confused by these feminine feelings.
"Tell me more about that," she said.
"I don't want to be a girl," he said.
"It makes me feel like I'm sick and dirty…"
"Let's explore these feelings a little bit, shall we?"
"Like there's something wrong with me…"
"Take off your dress, dear."
"Just do what you're told."
She helped him unbutton his girlish blue party dress.
"Now get on your hands and knees."
She tied his hands behind his back and made him kneel on the carpet with his face pressed against the floor. Then she put on a pair of rubber gloves, pulled down his blue ruffled panties, reached between his legs and started to squeeze his little pee-pee.
"How does it make you feel when I touch you down there?"
"I don't know…"
"Does it make you feel like a girl or a boy?"
Dr. Braun looked down at him. Her expression was very grave.
"Like a girl… I guess."
"Well then be that pretty little girl, Joyce. Go ahead and show me how it makes you feel…" she urged him. "Get to know your feelings. Don't be afraid of them."
So Joyce began to rock back and forth, pressing his pelvis against the heel of the doctor's hand until he got very excited and started to squeal, "Oh yes! Oh yes! I am a pretty little girl!"
Then his pee-pee squirted and he made an icky mess that dribbled down his smooth white thighs and he was horribly ashamed.
"That's very good, honey." The doctor took off her rubber gloves and washed her hands. "I think we're finally starting to make some real progress here."
"But I don't wanna do this anymore!" Joyce hid face in his hands and cried. "I don't wanna be this way!"
"Well, you better get used to it." Dr. Braun pushed him in front of a full length mirror. "I want you to take a good look at yourself, darling, and tell me what you see. Is that a boy or a girl?"
Joyce nearly died of shame when he saw himself.
Everything about his body was soft and smooth and rounded like a budding adolescent girl. His eyebrows were plucked thin and arched in such a way that they gave his face a look of perpetual wide-eyed innocence. He wore a pair of blue ruffled panties and blue high heels. His long blonde hair was pinned up above his head, but a few strands of it fell down and framed his pretty face. His waist was nipped-in by a tight blue corset that also lifted up the flesh around his nipples and gave him what appeared to be small jiggling breasts.
He kneaded and squeezed and tugged at them in stunned desperation and wondered when his bosom had become so big and sensuous?
He didn't know it at the time but Dr. Braun was putting female hormones in his food and the chemicals had begun to change his body and to give him this new feminine shape.
"Tell me what you see, Joyce. Is that a boy or a girl?"
"I, uh… guess… I don't know…"
"That's right, Joyce, you don't know. That's why I'm here, to help you find yourself. It might seem hard and cruel sometimes. But it's all done for your own good."
Dr. Braun stood up.
"Now, come here," she instructed him. "Take down your panties again. Don't be shy. Take down your panties and bend over my knee. That's right." She fondled his rather large and girlish behind. "Now I'm going to spank you, Joyce." She smacked him hard on the bottom. "Do you understand me? I'm going to spank you like a little baby."
"No!" Joyce squealed and begged her not to do it. But she didn't pay him any mind. And he had no choice but to lie there helplessly kicking up his heels while she spanked him like a naughty girl, until he was started to cry.
"Do you understand me, young lady?"
"Yes," he whimpered.
"I can't hear you." Her hand came down on his bright red quivering bottom. "Are you going to be a good little girl or not?"
"Yes, yes, Dr. Braun, I'll be a good little girl! I'll be pretty a girl… I promise…"
"That's better," Dr. Braun smiled grimly. Then she reached down between his legs and grabbed his flaccid little penis.
"Maybe you don't even need this!" she laughed.
And so his therapy continued for several months until he was reduced from an adolescent boy to a quivering helpless feminine thing with large hips and breasts and a tiny incongruous penis.
Then, one day, Joyce Francis Brookes was officially discharged from the private sanitarium of Dr. Matilda Von Braun and returned to the house of his aunt, Katherine Brookes.
* * * *
"I didn't believe it when the doctor said you'd gotten worse. But now I see it's true." His aunt Katherine looked at him with clear disdain. "That blouse is big enough to be a dress, dear, and those cute little shorts… what are they made of pink satin?"
"No… they're l-latex… b-biking shorts," he stammered.
"Maybe that's what you call them, Joyce, but to me it looks like you're wearing a tight pink girdle. Is that the effect you wanted to create, honey? Is that your idea of being a boy?"
"I don't understand," Joyce tried not to cry. But he was so upset by her remarks that he couldn't stop the tears from filling up in his pretty blue eyes. "I thought you wanted me to be like this…"
"Don't be ridiculous, Joyce. Why would I want you to be like this? You're clearly becoming more and more delusional, dear. You're lucky I don't keep you locked up in Dr. Braun's facility for the rest of your life…" She looked at him with obvious contempt. "Now take off those silly clothes, honey, and try to act like a boy for once in your pathetic life. Do you think you can do that? Or have you totally forgotten how to act masculine, Joyce?"
And so dressed in khaki pants and a white v-necked tee shirt, Joyce Francis Brookes tried to be a boy again. But it wasn't easy.
"Now don't you look nice," his aunt Katherine smiled. "Turn around, dear. Let me see you from behind. Yes, this is a definite improvement over those frilly girl clothes. It's just too bad you have such a big fat rear end, dear, it tends to ruin the masculine effect. Oh well," she sighed. "I suppose you're doing the best you can. Now, fetch me a cup of coffee, dear. Cream and sugar. Don't forget."
Joyce went into the kitchen, poured the coffee into a china cup, and then came back with the cup on a serving tray. His aunt watched him walk.
"The problem is you wiggle, dear."
"I'm sorry," he blushed. "I'm not trying to… wiggle."
"But you do, Joyce."
"It's just that… I always thought you wanted me to be more like… a girl…" he whimpered. "I'm so confused…"
"Don't be, sweetie. You're a just a big sissy. That's all you are. I tried to turn you into a boy. I really tried. But you're not really a boy at heart, are you Joyce? You're just little sissy. And so I guess you'll just have to get used to the idea of wearing clothes like this." She handed him a pair of light blue satin bib-front shorts with straps that crisscrossed in back, a pink cotton blouse, and pale blue open-toed sandals with ankle straps and small but definite heels.
"No please, auntie," Joyce shook his head in obvious horror. "It's going to make me look like I'm five years old!"
"Well, yes, I suppose it will, dear. But you give me little choice. Now take off your clothes."
"No… I won't!"
"If you're going to act like a spoiled child…" she grabbed him by the arm and pulled him across her knees, "then I'm going to have to treat you like a spoiled child!"
"Please… don't!" he struggled as pulled down his pants and then forced him into his pretty little outfit.
"Now you can go outside and play with the other children, dear." She patted him on the behind.
"No, please, auntie, I'll do anything you say!"
"But what's the alternative, Joyce? You're clearly not fit for a masculine role. So what else can we do?"
"I could wear a dress," he whimpered. "I wouldn't mind it so much, I mean, compared to this…"
"I'm not surprised," she adjusted the little straps that crisscrossed behind his back. "But then one day you'll change your mind and we'll be right back here in the same position again."
"No, no, I promise…"
"What do you promise, Joyce?"
"I promise to be a good girl, Aunt Katherine."
"Well, alright, if that's what you really want, precious. Who am I to stand in your way? But I want you to understand that you're going to have to wear dresses for a very long time. Are you prepared for that?"
"Yes, yes…" he squirmed as she unbuttoned his little blue satin romper suit and handed him a pair of frilly pink rumba panties and a matching ruffled bra.
"There," she smiled and clapped her hands when the panties were snug around his waist and the bra was clasped behind his back, pushing up his small but definite breasts. "I hope you're happy now!"
* * * *
After that Joyce was treated to a special regimen of shots and pills that kept him groggy and passive while Katherine shaped him into a regular teenage girl. On a dim masculine level he realized what was being done to him. But that level was so foggy and far away it hardly seemed real and it was such a bother to try and remember it anymore. It was so much nicer and easier to take a pill and do what he was told. And as long as he did, his Aunt Katherine and Mrs. Trowbridge treated him very well. It was only when he disobeyed them and tried to rebel that he got punished.
So he learned to say yes and didn't object when Dr. Braun came by and shot him up with female hormones and vitamins and sedatives that had him drifting in and out of a blissful semi-conscious state. Or when Mrs. Trowbridge dressed him in pretty panties that were trimmed with lace and a matching bra and then slipped him into a yellow sundress and buttoned him up in back.
"Now put on your cute little sandals," she spoke to him like he was a dim-witted child. And Joyce buckled the ankle straps of his white opened-toed sandals. "Now go downstairs, precious, and say good morning to your auntie."
"Yes, Mrs. Trowbridge."
And really, he reflected, as he drifted into the dining room where his aunt sat at a table eating breakfast, what's the big deal about wearing a bra? It doesn't make me a different person, does it?
"Hello, darling," she smiled at him when he entered the room. "This is Joyce," she said to the middle-aged man sitting at the table with her. "Joyce, this is Mr. Jones. Say hello to him, dear."
Joyce stopped short and looked at the man sitting beside his aunt. Mr. Jones was a short, portly figure in a dark blue suit. His gray mustache made him look like a walrus.
"Hello, Mr. Jones." Joyce lifted his hand and smiled rather meekly. His voice like his smile was slow and tentative. "How do you do?"
"You see what I mean?" she said to the man.
Mr. Jones studied Joyce for a long moment.
Katherine Brookes had told him over the phone that her nephew, Joyce, had psychological problems and kept pretending to be a girl. But he wasn't prepared for what he saw. In truth, the boy was actually quite stunning.
"You said he was effeminate. But I had no idea what you meant. He doesn't even seem to realize that he's a boy."
"Yes, it's sad, isn't it?"
Mr. Jones nodded pensively. He'd been appointed by a local judge to evaluate the mental condition of one, Mr. Joyce Francis Brookes, age 15, and to make a recommendation regarding a petition filed by his aunt, Katherine, to become the boy's permanent guardian. Based on what he'd seen so far, the child seemed to be mentally confused.
Katherine smiled at her pretty nephew and said, "How do you feel today, dear?"
"Very well, thank you," Joyce murmured softly.
"Come here, darling, and give me a kiss."
Mr. Jones watched as the boy approached his aunt with downcast eyes, his shoulders slightly hunched, his smile weak, his walk constricted. His attitude made the attorney think of an obedient dog, very well trained and afraid of committing any kind of minor infractions.
Katherine kissed him briefly on each cheek and then casually patted his head and asked him if he'd been a good little girl?
"Yes, Aunt Katherine," he nodded shyly.
It was a plausible reaction to peculiar question.
"Well, darling, sit down and eat your breakfast."
Mr. Jones watched as the boy in the pretty sundress slouched in a chair with his eyes half-closed and tried manipulate a knife and fork. At one point during the meal, he picked up a waffle in his hands and began to eat it. Then he wiped his greasy fingers on the top of his bare white thigh, leaving streaks across his smooth hairless skin.
"You forgot to use a knife and fork again, dear," Katherine chided him in a gentle voice.
Joyce began to tremble.
"Don't get upset honey," she said.
"I didn't mean to… I wasn't…"
"It's all right, darling." Katherine patted his hand. "Mr. Jones would like to talk to you a little bit now, dear. Do you think you can do that?"
"I g-guess…" Joyce nodded uncertainly.
"Don't be shy." Mr. Jones laughed heartily. "I won't bite. Come over here and let me have a good look at you." He patted his knee. "Sit down on my lap, young lady."
"Oh, Mr. Jones," Katherine laughed. "It's so nice of you to humor him… I mean her, my niece, of course…"
"I don't mind," said Mr. Jones.
"Well, isn't that nice," Katherine smiled. "Joyce, I want you to sit right here… on Mr. Jones's knee…"
Joyce did as he was told and found himself perched on the man's lap, straddling a wool trouser leg.
"How old are you, Joyce?" Mr. Jones put his hand around Joyce's waist and bounced him up and down a little bit.
"I'm almost twelve," Joyce giggled.
Mr. Jones knew the boy was nearly sixteen. But he went along with this childish charade.
"That's a good age for a little girl," he nodded. "Not too young and not too old." He slid his hand beneath the ruffled hem of Joyce's frothy sundress and squeezed his girlish thigh.
"Don't you think?" he chuckled.
Joyce blushed a little bit.
"You're very pretty girl…" Mr. Jones continued in such a way that Joyce finally relaxed and placed his curly head upon the old man's shoulder.
"Look how much she likes it, Mr. Jones," Katherine smiled.
"Yes, I see," Mr. Jones nodded. He slid his hand beneath Joyce's big androgynous bottom and began to rub and fondle it.
"You're a happy little girl aren't you, Joyce?"
Yes, Joyce nodded, she… he… actually enjoyed the gentle kneading pressure of Mr. Jones's warm probing hands. He liked the rumble of his strong bass voice, and the masculine smell of his body. It was very reassuring.
"Yes," he murmured softly.
Mr. Jones studied Joyce's effeminate appearance and shook his head. The boy's lips were painted dark blood red. His eyelashes were thickened with black mascara. He looked more like a decadent showgirl in a little sundress than a fifteen year old boy.
"Is your auntie good to you, dear? Do you like your auntie? Does she take good care of you?"
"Oh, yes, Mr. Jones," Joyce hastened to reassure him. "Aunt Katherine's the best!"
"You see what I mean?" Katherine laughed triumphantly. "She wants to be this way. There's nothing I can do about it."
"Yes, yes," Mr. Jones nodded in agreement. "It's seems pretty clear to me that Joyce desperately needs your help. I'm going to recommend that you get full custody for the next twelve months. Then we'll re-examine the case and reach a final decision. You can expect me to stop by in the mean time, to see if she's doing any better. I hope you don't mind?"
"No, of course not," Katherine smiled graciously. "Feel free to see her as much as you like."
"Well, alright," Mr. Jones laughed and lifted Joyce's bottom up and bounced it up and down. "You and I are going to become very good friends, young lady."
"I have to go swimming!" Joyce cried suddenly. "If I don't exercise every day I get all soft and saggy…"
Then the quivering boy gathered up his skirts and petticoats and scampered very quickly out of sight as if he really was a timid little girl and not a teenage boy trapped in childish dresses.
* * * *
After that papers were signed which gave Katherine complete legal and financial control over her nephew who was deemed, by Dr. Matilda Braun, to be a paranoid schizophrenic. Dr. Braun kept him medicated with thorazine, Prozac, tuinal, morphine, valium, and various other chemicals, as well as estrogen, which made him soft, flabby and sedate.
By the age of 17 Joyce Francis Brookes had a voluptuous ass and prominent breasts that bounced up and down when Katherine took him to the mall to buy new lingerie and make up.
By now all the salesgirls were accustomed to seeing him dressed as a girl, in tight satin jeans and a ruffled blouse, and nobody seemed to remember him as a boy.
And so the days passed in a pleasant blur. He was kneaded and squeezed by a heavyset masseuse who was hired by his aunt to help break down the muscles in his chest, even as the estrogen took effect and his body became plumper, softer, fatter in the hips, bosom and buttocks.
"My…" the masseuse ran her hand across his belly. "Your skin is very soft and smooth." Then she pulled the towel down even lower and saw that his pubic hair had been carefully shaved and shaped like a heart to frame his tiny penis and balls no bigger than cherries.
Joyce lay there too confused to move, too embarrassed to object when her probing fingers pressed and squeezed his soft white breasts, and then dipped down even lower to rub his smooth tummy.
Once her fingers brushed against his penis, as if by accident, and then to his utter chagrin he felt his little wee-wee stiffen. The masseuse must have noticed, but she didn't say anything about it.
Instead, she told him to roll over and started to squeeze his fat behind. Whether or not he was male or female didn't seem to matter much to her.
"Very nice," she ran her fingers between his thighs and spread his buttocks slightly apart. "You have very little cellulite," she inspected him carefully. "And a big firm sexy bottom."
* * * *
And so it went until one day Joyce got out of bed, wearing a pretty pink diaphanous nightie, and saw the faint outline of his bosom in the mirror; his nipples jutting against the sheer material; his glistening red lips pushed forward in a sexy pout.
"Hi, sweetie!" he giggled in a girlish voice.
Then he suddenly realized he was flirting with himself.
"Oh, my God!" he covered his face.
And suddenly he saw what they had done to him. He'd become 99% girl. And that last one percent was fading fast.
It was amazing that Joyce managed to have such a lucid thought. But once he did it resonated in his mind and drove him to act in an unexpected manner.
That day, while his aunt was busy planning yet another dinner party, Joyce Francis Brookes snuck into her palatial boudoir, rummaged through her drawers until he found a purse full of money, took all the money, and then abruptly ran away from home.
* * * *
That night, Joyce arrived in New York City, dressed in black latex stretch pants and a white nylon blouse.
He had nowhere to go, so he hid behind dark feminine sunglasses and lingered in the Port Authority bus terminal until the sun rose slowly over the city.
Then around 10 o'clock he drifted into a men's clothing store and bought himself a pair of flat black perforated wing-tip shoes, gray flannel pants, a white button down shirt, a red tie, and a dark blue flannel sports jacket. He had his hair cut short in a barber shop. Then Joyce changed his clothes in the bus terminal bathroom, and when he emerged he was dressed like a man.
By twelve o'clock he was exhausted and terrified.
His whole life he'd been taken care of and now, suddenly, he had to look after himself, and he didn't know how to do it.
He found a room in a cheap hotel, got undressed, and climbed into bed at 5 p.m., too sad and scared to think about the future.
The following day, he bought a newspaper and looked in the help wanted section. Most of the jobs required some kind of experience. But there was a temporary agency that needed 10 people to lick and stamp envelopes, and Joyce figured that he could do that; so he went down to the agency.
"Miss, do you type?"
"Oh, sorry sir, do you type?"
"A little bit…"
"Do you answer phones?"
"Sure, I can do that."
The receptionist took his registration card into another room. She emerged a few minutes later and told him to go inside and talk to a guidance counselor.
Joyce did as he was told and found himself seated across a large metal desk from a big-boned woman named Gretchen Schmidt.
Gretchen Schmidt looked at Joyce and saw a pretty boy with plucked eyebrows wearing a jacket and tie, but she made no mention of his effeminate appearance. This was, after all, New York City and people were free to do whatever they liked. If this adorable little sissy wanted to pluck his eyebrows and dress like a boy, well, so be it. She knew of a job… just the perfect situation, really, for this sweet young thing.
"I'm here about the job stuffing envelopes," Joyce murmured softly. Even with a crew cut, wearing his new blue sports jacket and men's charcoal gray flannel pants, he looked very sweet.
"That job's taken," Ms. Schmidt glanced at his application form. "But I may have another position, which you might actually prefer." She smiled at him lazily. "How would you like to be an administrative assistant?"
"That would be great!"
"I know a woman who owns a small clothing company and she needs somebody to answer her phone. Would you be interested in a job like that?"
"You mean a secretarial position?"
"Sure, why not? She needs somebody to answer the phones and to take a few messages. Can you do that?"
"I g-guess," Joyce stammered nervously.
"Good." She picked up the phone and called her friend, Crimson. "I have a candidate for the job we talked about. Yes," she laughed softly. "I think he'd be perfect."
They spoke for a moment. Then Ms. Schmidt hung up the phone and turned to him. "She wants to see you in the morning. Nine o'clock sharp. Don't be late."
* * * *
And so, the next day, bright and early, Joyce reported to the Viva Glam Dress Company.
The dress company was located in a big a refurbished loft near the river.
Ms. Crimson was a tall, beautiful woman with long red hair, green eyes, and a heart like a cake of ice. She made her living designing and selling woman's clothing.
She sat behind an impressive desk, dressed in a simple black linen shirt, open at the collar with the sleeves rolled up to the elbows, pleated black linen pants, and black leather sandals.
"Listen," she said. "I need somebody to answer phones and run errands for me. Do you have a problem with that?"
"No, I mean…" Her blunt assertive manner caught him off guard. "I just really need a job."
"I'm sure you do," she looked at Joyce and nodded briefly. "Tell me everything about yourself. Who you are, what you want, where you come from, everything."
A soft uncertain smile played across his pretty face.
"I don't know where to b-begin."
"Do you type? Do you take short-hand?"
"No, not yet," he confessed. "But I can learn."
"You don't type. You don't take short hand. You obviously don't have any pertinent job skills. So what good are you?"
"Well, uh…" he stammered and licked his lips. "I, uh…"
She waited patiently for an answer, but the poor little thing just didn't seem capable of talking at the moment.
"That's okay." She moved on to another question. "Would you rather work for a man or a woman?"
"I think I'd rather work for a w-w-woman," he answered softly. "With a man, I'd feel a little more self-conscious, doing what I do…"
"Why's that? You're not embarrassed to be a secretary, are you, Joyce?"
"No, it's fine," he swallowed with some difficulty. "But, I mean, a man might sneer at me. With a woman, it's different, it's almost like we're on the same side…"
She looked at Joyce sitting perched on a stool with his knees pressed together and imagined his thighs would be smooth and pretty if she pulled down his pants and touched them. It was a bit of a disappointment, really. She preferred a man to at least try and resist her before she totally broke him down.
"That's sweet," she smiled briefly. "But if you're going to be my secretary, you have to remember that I'm your boss. We're not on the same side. We're not equal. You work for me. I hope you understand that."
Joyce felt himself nodding in agreement. His tongue was stuck to the roof of his mouth and his heart pounded in his ears.
"Yes, Ms. C-Crimson," he managed to mumble.
"Good." She nodded. "Now fetch me a cup of coffee, dear."
* * * *
Pretty soon, Crimson had him running down to the corner store, buying her tampons, picking up her dry cleaning, making her lunch reservations. It was, from her perspective, kind of like having a personal maid.
And Joyce was only too happy to fetch her coffee, to be her secretary, her personal assistant, anything she wanted. Why? Because he was intoxicated by her beauty.
And her power.
Of course there was nothing overtly sexual about their relationship. Not that Joyce didn't dream about it. But he was too shy to approach her directly, and Crimson seemed perfectly content with their relationship.
A real man, no doubt, would have grabbed her and kissed her hard on the lips… but Joyce wasn't very aggressive. And for some reason, in his erotic imagination, he was the one who had their skirt hiked up, their panties pulled down, their nipples hard, their mouth half-open… not the other way around.
Nonetheless, he tried to change his ways.
Every day he did a series of push ups and sit ups designed to give him "six-pack" abs and bigger biceps. But even so, a layer of subcutaneous fat still clung to his hips and breasts and made him jiggle like a woman when he moved.
But the real problem was that he continued to think of himself in female terms, as "she", and "her", "Miss Joyce Francis Brookes." And though he tried to shake the image of himself in pink ruffled panties and matching bra, he still felt weak and voluptuous when he pictured himself dressed in pretty lingerie…
No, no, no!
He climbed into his little bed and started to cry.
From now on he was going to be a man!
But then every day at work, Crimson kept teasing him, saying little things that seemed designed to make him blush.
"You're as bad as a woman, Joyce."
"You're such a girl."
It was all said in jest, so he tried to laugh, but it made him feel uncomfortable and he wished that she would stop.
"But why?" Crimson seemed surprised.
"Because I'm not a girl," he blushed.
"You're absolutely right, Joyce. I'm sorry if I upset you."
"It's just that you seem to forget sometimes…"
"Let me make it up to you, honey." She kissed him on the cheek. "How about you and me go out to dinner? It'll be my treat. Whatta ya say, honey?"
"Yes, okay, thank you," he nodded happily.
They went to one of her favorite restaurants down in the West Village. Crimson ordered for both of them.
"We'll have the lobster paella and a bottle of wine."
The waiter wore a white jacket and a black bow tie. He served them from a metal crock pot filled with rice and seafood. Crimson first. Then Joyce.
"That's enough for him," she interrupted the waiter. "He needs to watch his figure."
The waiter glanced at Joyce.
When Joyce said nothing he nodded.
"Very good, Madame."
Joyce blushed and hung his head.
The portion on the plate was hardly fit for a child.
"Can't I have a little more?" he pleaded.
Crimson looked at him with a peculiar smile.
"You'd look a lot nicer if you lost a few pounds, dear."
"But I'm hungry, Ms. Crimson…"
"You're so cute," she kissed him briefly on the lips.
When he responded by opening his mouth for her to insert her tongue, she laughed and said, "If I was a man I'd fuck you in the ass and make you squeal, baby!"
"What do you m-m-m-mean?" he stammered in surprise.
"I'm just kidding!" she laughed and poured him another glass of wine. "Relax, sweetie, have a good time!"
Joyce got very drunk and giddy.
Then there were colored lights spinning overhead and they were dancing and Crimson holding him very close, squeezing his bottom, rubbing his hips, and the next thing he knew they were back at her place, and she was pulling down his pants.
"Wait… wait!" he whimpered when she touched his rigid pee-pee.
"Oh, no, wait…" he started to ejaculate.
"Poor, baby," she rubbed the gooey stuff across his pale tummy. Then she pushed him down between her legs and told him to lick her pussy. "That's a good boy," she smiled when the tip of his tongue found the right spot. She pressed her pelvis against his face and rocked slowly back and forth.
Joyce was blind and could barely breathe. All he could do was lick and lick is what he did.
"Keep going," she held him there, grinding her pussy against his face until, finally, she came.
Then she rolled away.
Afterwards, Joyce took a shower to clean himself up, and when he emerged from the bathroom, he couldn't find his clothes.
"They're in the washing machine," Crimson told him.
"But what am I supposed to wear?"
"You can wear my culottes and a tee shirt."
"Don't worry," she reassured him. "It's no big deal."
So he put on a pair of white rayon culottes that fit him like a skirt and a big white v-necked tee shirt and a pair of baggy white athletic socks and joined her in the kitchen, where Crimson was standing with her hands submerged in a sink full of dirty dishes.
"I could use some help." She handed him a sponge and a pair of rubber gloves, and Joyce started to do the dishes.
"Thanks a lot," she kissed him briefly on the mouth. "Can you finish up, while I take a bath?"
"Sure," he nodded.
"You might need this." She handed him a frilly white apron. "So you don't get your clothes wet."
"No thanks, that's okay, I'm fine…"
"Don't be ridiculous." She insisted.
So Joyce reluctantly complied. The apron had puffy sleeves and a ruffled hem and a big white bow that she tied behind his back.
"Don't you look sweet!" Crimson laughed and put her hands around his waist.
"I feel silly…"
"Relax," she smiled happily at the sight of him standing there at the sink with his hands immersed in the soapy water. "You look great," she winked and blew him a kiss.
Then Crimson went into the bathroom and took a bath, and Joyce did all the dishes.
* * * *
And that's how it started.
Within a few days Crimson had Joyce installed in a little room down the hall from where she slept and he was living there full-time. They were going to be roommates, she told him. That meant Joyce would do the dishes, wash the clothes, mop the floors, cook the food, and do all the other domestic chores, and Crimson would pay the rent because she made most of the money.
"In fact, you're lucky you have a job at all," she liked to remind him. "You're not really qualified to be a secretary. You have no job skills to speak of. I guess you could sell your fat ass on the street. But you wouldn't be worth much money."
"W-what d'you mean?" Joyce stammered.
"Relax. I'm kidding," she laughed. "You're such a baby, Joyce. Sometimes I think I should dress you in diapers and give you a bottle to suck on like a nipple…"
Joyce wanted to scream, no, don't talk to me like that!, but he didn't say anything.
Crimson kept prodding him, pushing him, hoping he might show a little moxy. But he just rolled over like a well-trained pet and did what she told him. When she realized that he wouldn't object, she took full advantage of the situation.
By day Joyce worked as her receptionist, answered her phones, and took her messages. At night he waited on her hand and foot.
"I'm going out with a client," she told him. "I should be back around midnight. I want you to be awake when I come back."
"Alright," he nodded, submissively.
"How do I look?"
Crimson turned around and modeled a tight black skirt with a dark green blouse that shimmered when she moved.
"I think you're the most beautiful woman I've ever seen!" he exclaimed in all sincerity.
"That's sweet." Crimson leaned down and kissed him briefly on his cheek. For a moment her breasts pressed gently against his arm and Joyce quivered with excitement.
"Do me a big favor, sweetie?"
"Sure," he smiled happily.
"There's some dirty undies in the bathroom, Joyce. I want you to wash them for me while I'm gone. Use warm water and a few drops of fabric softener on each item. Then hang them up to dry in the shower, understand?"
"Okay," he agreed.
"You're so precious," Crimson squeezed his cheeks together and made his lips pucker between her long red fingernails. "I don't know what I'd do without you."
"I feel the same way!" He tried to kiss her.
"Now don't be naughty," she pushed him away.
"But I love you!"
"Now, kitten, you know I don't think of you that way."
"Why not?" he complained.
"Because, silly," she grinned and grabbed him by the nipples. "You're my bosom buddy!"
After she blew him a kiss bye-bye and departed for the night, Joyce trudged sadly into the bathroom. He opened the dirty clothes hamper and looked inside. It was filled with delicate bras and panties, ruffled silk and satin under things that shimmered in his hands and smelled like Crimson when he buried his face in her sexy lingerie…
Then he looked up and saw himself in the mirror: a small delicate blonde haired boy playing with a pair of lady's panties in a pink feminine bathroom. No! He shuddered. His face twisted in pain. He wouldn't let it happen again! Not again!
But what was he supposed to do? He didn't want to fight with Crimson. He didn't want to make her mad. And maybe it wasn't such a big deal. Maybe he shouldn't complain. It really wasn't so bad. It wouldn't take that long.
"So do it," he sighed and rubbed a glistening drop of fabric softener into the soiled crotch of Crimson's white nylon panties and scrubbed the dirty brown spot under a steady stream of tepid water until the little shit stain disappeared.
* * * *
In return for a job well done, Crimson gave him a pair of flared, black satin, high-waisted pants and a white chiffon top with pearly buttons.
He wore the ensemble to work, even though it made him feel terribly self-conscious. The shirt was so sheer, people could see his nipples pressed against it, and the black high-waisted pants fit too tight and seemed to accentuate the shape of his ass and made it look even bigger.
Crimson teased him when she saw the outfit.
"Maybe you should have worn a bra."
"What do you mean?"
She pointed to his blouse and said, "You can see right through it, dear. Your nipples are so obvious… it really seems indecent."
"Well, you bought it," he blushed.
"Yes, but I thought you'd wear a little sleeveless tee shirt or something underneath it. You're such a ninny, Joyce."
"Is it really that bad?" he worried.
"Sometimes when I see you from behind I think you're a girl. Then I realize that you're not."
"Thanks a lot," he muttered.
"It's just that you have a very large bottom, dear. It's big and round and, well, it protrudes in a way that makes you look like quite sexy and feminine."
"Are you serious?" He studied his buttocks in the full length mirror that dominated one corner of the office.
"I don't want you to be self-conscious, kitten. I just think you should realize the impression you make. After all, this is New York City, honey, and there's lots of men out there who might think you're very attractive."
"Is it really so noticeable?" He bit his lower lip.
"You're petite. You're pretty. You have a tiny waist. And gorgeous blonde hair."
Joyce glanced in the mirror and said, "It is getting kind of long. Do you think I should cut it?"
"No! Absolutely not!" Crimson ran her fingers through his golden curls. "Most girls would love to have hair like yours."
"But I'm not a girl."
"You keep saying that, Joyce, like you're not completely sure. But you don't have to prove anything to me, darling. I like you just the way you are."
"Do you really?"
"I just think it would be even more flattering if you did something with your hair. Right now it has no particular shape or style and sometimes, dear, if you want to know the truth, you look a little slovenly." She sighed. "And that's embarrassing."
All these little comments made him blush and shake his head in consternation at first. But she kept repeating them and teasing him in little ways that seemed meant to reinforce his girlish feelings.
And so one night when Crimson was out, Joyce gave in to her constant prodding. He crept into her bedroom after she was gone and then took off all his clothes. He opened a dresser drawer filled with shimmering lingerie and dug through a netherworld of lacy frilly under things until he found a pair of black ruffled panties and a matching ruffled bra that he liked and tried on. The bra was a teeny bit too big in the bust, but the panties fit nicely when he pulled them up around his waist.
He dug through a closet filled with low-cut dresses, tight leather skirts, plunging tops, and found a pair of black high heeled shoes. He put them on and minced over to her vanity, where he sat down with a tube of red lipstick and black mascara and did his lips and eyes… and when he was done he looked in the mirror and realized that she was right.
He did look like a girl.
He had a narrow waist and rounded hips, flowing blonde hair and pretty blue eyes. The only thing out of place was the tiny erection between his legs.
"Honey, I forgot my purse," Crimson sailed into the room and stopped abruptly when she saw him standing there, dressed in her best underwear.
"What the hell are you doing?"
"Oh, my God!" Joyce covered his face. "I took a shower. My clothes were dirty. So I came in here… I'm sorry!
"Now it all makes sense," Crimson scowled.
"I can explain…"
"You're such a pathetic twit!"
"Shut up!" she yelled at him.
"But I can explain…" he started to cry. "I'm sorry! Crimson, please…"
She swung around and slapped him across the face. Joyce reeled backwards in surprise and began to whimper.
"Don't snivel at me!"
"Shut up, Joyce. You're acting like a baby."
Crimson sat down on the bed and crossed her legs.
"And so I'm going to have to treat a baby. Go over there and get my hair brush, Joyce."
"But w-why?" he stammered in a small voice.
"Just do what you're told."
Reluctantly, Joyce went over to the dresser and came back with a large silver backed hair brush with hard white bristles.
"Now lie across my lap."
"Why? W-what're you gonna to do t-t-to me?"
"You were very naughty, Joyce. And naughty boys have to be disciplined when they're bad. You know that. Now lie down across my knees. Right now!" She clapped her hands.
"No, this is outrageous, I won't do it! I'm not a little boy, and you can't treat me like one!" Joyce cried.
"Well, maybe you're right. Maybe you're not a little boy at all. Maybe you're really a little girl. Maybe I'll have to make you wear a dress for a couple days. Maybe then you'll get the message and start to behave."
"No, absolutely not," he folded his arms across his chest. "We can't have a relationship like this, Crimson. I'm not a child, and I won't allow you to treat me like one."
"Well, it's up to you, Joyce. But what are you going to do without a job, no money, and no place to sleep?"
"Crimson please…" he started to whine.
"It's your choice, dear. You have to make a decision."
"Don't make me…" Joyce mumbled.
"I'm not making you do anything, Joyce. It's totally up to you. But if you don't climb across my knees right now and do what you're told, I want you to leave."
"No, don't make me go…" Joyce slowly approached her with his head hanging down. He was painfully aware of what he must look like dressed in her bra and panties.
"Now lie across my lap," Crimson smiled. Then she gripped the elastic waistband of his ruffled panties and pulled them down around his thighs, exposing his big girlish bottom.
"What a cute behind." She squeezed his ass, making it jiggle, kneading it like unformed dough.
"Oh, no… please!"
"Hold still!" She brought the hair brush down with a sharp resounding smack upon his ass and made squeal in pain.
"How dare you wear my panties!"
"No… no!" he started to cry.
"You're lucky I don't throw you outside like this!" She spanked him as she spoke to him and he kicked and wiggled beneath her hand. "You're going to stretch my things, you big, stupid cow!"
"I'm sorry… I'm sorry!"
Joyce tried his best to get away, but she was bigger and stronger than he was and she pinned him down across her legs and continued to spank his plump quivering bottom.
"Oh, no, don't!" he cried.
But he couldn't move his arms.
"I'm sorry!" he whimpered and squirmed like a child, wiggling his hips in vain. And as he did, his little pee-pee pressed itself against her skirt and thighs and he got excited.
"What a big… fat… girlish… ass!" Crimson laughed. The hair brush landed upon his bottom to punctuate each word. "Just think how sexy you'd look in a tight black skirt, wiggling your ass like that…"
"Wait! Stop! Please stop!"
Joyce started to quiver uncontrollably in her lap.
"Oh, yes! I can see my little girl wants to wear a sexy skirt! She does, doesn't she?"
"Oh yes, oh yes!" Joyce cried in a high-pitched voice. Then a few drops of milky white semen spurted from his pee-pee and dribbled onto Crimson's skirt.
"Oh, look!" she held him by the scruff of the neck and rubbed his face in the gooey stuff. "Baby made a boo-boo, didn't she?"
Joyce was mortified. He crawled off her lap and curled up in a fetal position on the carpet.
"Here," she handed him a pink nightie and said, "You can wear this to bed tonight, sweetie pie."
"No," Joyce mumbled and shook his head when he saw it.
The nightie was trimmed with delicate ruffles, ribbons, and lace. Several shiny buttons ran down the front.
"Come here, Joyce. Now raise your arms above your head. Bend forward a little bit. That's a good girl." She buttoned up the frilly pink nightie.
"Oh my," Crimson looked at him and smiled. "Don't you look sweet! Don't you look pretty! Oh, Joyce, you're an absolute doll! Just take a little peek in the mirror, honey! And you'll see what I mean!"
"Oh, no!" Joyce's face contorted when he saw himself.
There in the mirror was a small chagrinned boy with golden curls wearing a short ruffled nightie. The material of the ruffled nightie was very sheer and did almost nothing to disguise the shape of his wide girlish hips, narrow waist, and quivering bosom.
"What's the matter, sweetie? Don't you like what you see?"
He wanted to smash his fist against the mirror and scream, "I hate it! I hate it!" But he didn't. Instead he said, "No, I mean, yes, it's very pretty," he stammered in stunned confusion. "But I don't want to wear it…"
"Why not, honey?"
"Well, because, I mean, you know…" he mumbled weakly.
"No, I don't know. Tell me what's wrong, sweetie."
"Because they're girl's clothes!" he cried in frustration. "And I'm not a girl! You're a girl! You're the one who's supposed to wear stuff like this!"
"Oh, kitten, don't be ridiculous. I mean, girls wear pants all the time. So why can't boys wear nighties?"
"But why do I have to be the one who wears it?"
"You don't have to do anything, Joyce. But it really makes me wonder, what's the big deal? Why are you so afraid of this?"
"It's just that I feel embarrassed and – "
"What are you saying, Joyce? Are you saying there's something wrong with being a girl? Are you saying that girls aren't as good as boys? Is that what you're saying?"
"No, I mean, there's nothing wrong with being a girl but, I mean…"
"Then what's the problem? Nobody's going to know about it but you and me."
"I just think…" he began.
But Crimson reached out and pulled him suddenly toward her.
He stumbled into her arms.
"Just be yourself…" she whispered.
And then very slowly she unbuttoned the top of his little nightie and reached inside. Her fingertips brushed against his nipples and they stiffened beneath her touch. Then her hand slid around the soft heaviness of his breast, and she begin to gently fondle the small resilient globe of flesh.
He resisted at first.
"Crimson," he said in a choked voice. "No, please…"
She wrapped her hand around his waist and pulled him close against her. Joyce hid his face in the warm hollow of her neck. She held him tightly, smoothing his curly blonde hair with her right hand, while her left hand slid under the hem of his little nightie.
"Oh, no!" Joyce began to moan in a tiny voice tinged with desperation, "Oh, please, stop!"
Crimson smacked him across the face and he stumbled backwards, totally stunned and frightened. Then she grabbed him by the elbow and dragged him over to the mirror.
"I want you to play with your titties."
"Crimson, please…" he saw himself cringing beside her in the mirror. "Why are you doing do this?"
"C'mon." She encouraged him. "Work it, baby!"
Blushing shyly, Joyce complied.
He had pretty little breasts that jiggled and bounced when he played with his nipples. His nipples grew hard. They looked like two small rubber erasers as he pressed them between his fingers.
"That's right. That's good. Now bend over, baby."
Joyce bent forward slightly and Crimson pressed her index finger against his tightly puckered asshole.
"Now spread your legs, you silly cow."
She inserted her fingertip in his rectum.
"Oh no!" he squealed.
"C'mon, precious, show Mommy what a good little cow you really are. That's right, baby. That's right."
Joyce lifted his ass and began to whimper.
"Oh yes, she's such a pretty cow!" Crimson cooed in his ear. "And maybe one day, if she's very-very good, she'll have big soft titties that bounce and jiggle just like Mommy's!"
Crimson worked her finger back and forth and suddenly Joyce started to wriggle and squirm, crying, moo moo moo!, in a high-pitched voice. And then he started to squirt.
"And to think I was ever attracted you!" Crimson laughed.
* * * *
The next day Joyce snuggled in bed watching Saturday morning cartoons. Crimson sailed brightly into the room.
"Hello, darling," she smiled down at him. "Look, I got you a present." She held up a shopping bag. "Bras and panties… for my little girl. And see what else I bought you, precious. A baby doll nightie. Isn't it delicious?"
"Listen," he squirmed. "I wanted to talk to you about last night. I don't want you to get the wrong idea…"
"What do you mean?"
"There's a lotta stuff I haven't told you about my past. Things that happened to me and stuff."
"First you have to promise me that you'll never tell anybody what I'm about to tell you. It's just between you and me."
"Well… I was raised by my aunt," he began, haltingly. "And she used to make me dress up like a little girl." He blushed bright red at this confession. "And that's why I ran away from home. I swore I'd never let it happen again. And that's why we can't go on like this."
"I see," Crimson nodded sympathetically. "Was your aunt mean to you? Was that the problem?"
"Yes, she was very mean… and I was scared of her all the time."
"Well, don't worry, I'm not your aunt," Crimson kissed him briefly on the lips. "And I won't ever hurt you, kitten. So go ahead, honey, and let me see how you look in your new undies."
"But you don't seem to understand…"
"I said, put on your panties!"
Little pink nylon panties trimmed with lace. Stretched tightly across his ass. They made him feel so weak and helpless.
"Now isn't that better?"
"No," he shook his head. "You must be crazy."
"You think I'm crazy? You're the one who's been dressing up like a little girl since he was, like, six years old."
Joyce was stunned.
"I told you that in confidence. I trusted you. And I wasn't dressing up since I was six years old. I was fourteen or fifteen and she made me do it! I had no choice!"
"Calm down, darling." She took him by the hand. "Your secret's safe with me." She kissed him slowly on the mouth.
"Oh, Crimson!" he sighed.
Then her tongue filled his mouth and he felt her fingers probing the crack of his plump ass.
"Oh, Crimson, please, don't!"
"You sound just like a woman," she smiled and forced her middle finger into his tightly puckered hole and then slowly moved it back and forth.
"You like it, don't you, kitten?"
"Yes," he moaned in abject defeat. "Yes, Crimson."
"Tell me how you like it, bitch! Tell me!"
"Oh, I do, I do!" he squeaked and started to cum, squirting a little bit in his tight pink panties.
"Now clean it up," she ordered him.
"What d'you mean?"
"Just reach inside your panties and use your fingers. That's right, honey," she nodded as he shyly reached into his nylon panties wet with jism. "Now lick it off your fingers," she encouraged him.
He stared at her in disbelief.
"You heard me."
And slowly, nervously, he lifted a painted nail to his fat red lips and licked the sticky jism off his finger.
"That's right, honey," she repeated. "That's a good girl."
She smiled as he took the gooey digit in his mouth.
"Now suck it," she demanded. And so he did, sucking the wet stuff from his fingers and swallowing it, just like a well-trained house pet.
"Now didn't that taste good?"
"Yes," he nodded, a little bit sadly.
"Good," she smiled. "Now wash the dishes, Joyce. Then you can watch TV for half an hour before you take a little nap. What do you say?"
"Thank you, Ms. Crimson."
"That's right," she kissed his lightly on his glistening lips. "Now hurry up," she swatted him on the rear.
Then Joyce scurried into the kitchen where he put on his ruffled apron and his rubber gloves and proceeded to wash all the dirty dishes.
* * * *
The next day, Crimson had cocktails with her girl friend, Alana. Alana was tall and blonde with a gorgeous figure.
"You'll never guess what happened to me the other day. I came home unexpectedly and I found Joyce – "
"In bed with another woman?"
"No, hardly," Crimson laughed. "He was mincing around in my underwear and high heels."
"No, you're kidding!"
"You should have seen him."
"I bet he looked adorable."
"I thought he was gonna cry."
"So what did you do?"
"I told him, from now on, in my eyes, he wasn't a man to me anymore. That if he wanted to stay in the apartment, he was going to have to dress and act like a woman all the time."
"You actually said that? What did he say?"
"He didn't say anything," she laughed. "Can you imagine? And ever since then the little bitch's been wearing my bras and panties and prancing around the place dressed up like a woman. He does all the boring household chores while I go out and do whatever I want. It's just about perfect."
"Does he actually cook and clean?"
"Yeah," Crimson replied. "He's very well behaved."
"I'm jealous," Alana admitted.
"Would you like me send him over?"
"Why? Are you giving him away?"
"Actually, I find it hard to think of him as a man anymore. Joyce is becoming more, like, the cleaning girl."
"Well, I do need a good maid."
"Okay, then, it's settled," Crimson smiled. "I'll send her over some time."
* * * *
From then on, Crimson began to slowly alter his daily wardrobe. She introduced more and more feminine things, velvet suits and satin outfits which she assured him were quite masculine, but also very stylish.
The changes occurred so gradually, he almost didn't notice them at first, until one day he looked in the mirror and was surprised to see what appeared to be a sexy young woman wearing a pair of flared, tightly fitted jeans, a little black tank top, and a pair of unisex sandals. Her long blonde hair was pulled back in a ponytail.
My god, he wondered, what have I become?
I look like a woman, he stared at himself in disbelief.
Then he began to sob.
Pretty soon Crimson had him wearing all these sexy little outfits; tight Capri pants that zipped up the ass, pastel pant suits, bras and blouses. It was hard not to notice this obvious transformation, but since he worked for Crimson, and Crimson was the boss, none of his co-workers said anything about his increasingly girlish appearance.
Then one day Crimson called him into her office.
"Honey, I need a fitting model and nobody's around. Would you do me a favor, baby, and put this on?"
She handed him a slinky blue dress.
"What do you mean?"
"I just need to pin up the hem and take in the bust, and you're just about the right size. C'mon, kitten, don't be shy."
So he put on the dress and high heels, and then, well, to complete the effect, she said, "Here's a little lipstick."
"What do I need lipstick for?"
"Oh, shut up," she laughed and took the lipstick and said, "Pucker up, honey." Then she did his lips and took a step back to get a better look at him. "Damn, you've got a nice figure, Joyce. Move around a little bit. Walk over to the window. C'mon, baby, shake your ass. Show me what you're workin' with."
"Don't talk to me like that."
"Like I'm a doll or something…"
"Honey, you're wearing a dress that fits you in a flattering way, that shows off your figure and makes you look pretty. So why shouldn't you shake your ass?"
"Because I'm a boy! And you're not supposed to me like that! And I know the only reason you do it is because you think you can get away with – "
"Darling, I'm sorry," she cut him off. "But when I see you dressed up like this I just can't believe that you were ever really meant to be a boy. I mean, just look at yourself," Crimson smiled at the blushing young man. "You have beautiful lips. And lovely thighs. So why shouldn't you wear lipstick and a sexy dress?"
"Because I'm a boy…" he repeated weakly.
"Well yes, of course, you're a boy, but why shouldn't you be allowed to have pretty legs and painted toenails? Why shouldn't you be allowed to look beautiful? Is that against the rules?"
"I don't know… maybe you're right," he murmured.
"Of course, I'm right."
Then to his utter shock and amazement she took him around the office, dressed like that, and showed him off to all the other girls who laughed at him in his plunging evening gown, but said, yes, he made a very cute mannequin.
Joyce was totally embarrassed by these and other suggestive comments and the way all the girls gathered around and touched and squeezed his bottom to see if it was real.
"He has an ass just like a woman…"
"And a nice top too…"
"Are we done?" he stammered and blushed and looked at Crimson.
"Yes, honey, we're done, for now." She led the mortified boy back into her office and watched him as he wiggled out of his tight blue dress.
"How you could you do this to me?" he cried in frustration.
"What's do you mean?"
"I've never been so embarrassed in my life!"
"Well, everybody thought you looked very pretty. So there's nothing to be embarrassed about. In fact, I discovered you're a perfect size eight. And that's hard to find." She put her hand on his high rounded buttocks. "I think I'm going to need you to model dresses regularly. So you better get used to wearing them, Joyce. It's going to be part of the job. I hope you understand that."
"Well," he mumbled weakly as she fondled his big firm bottom. "Do you have to show me off like that? In public?"
"Oh, kitten, don't be shy. Everybody knows there's a lot of sissies in the fashion world."
* * * *
Joyce found it easier not to think.
He stopped exercising. A new feminine softness began to swell his breasts and buttocks. He was usually high on drugs and booze and never fully aware of his condition. He only knew his weight was dropping and his face looked strangely vague and feminine in the mirror, but for some reason it didn't seem to matter anymore.
Then one day he glanced down at his hands while he was doing the dishes and suddenly saw how feminine they looked. His nails were long and painted red. They were very pretty. For a girl.
He hid them in the soapy bubbles.
Out of sight, out of mind.
"What's the matter?" Crimson came over and kissed him on the mouth, smudging his lips with her own dark red lipstick.
"Would you please not talk to me like a child."
"I know exactly what the trouble is, baby doll."
"What's that?" he blinked.
"You're feeling insecure about your femininity, aren't you, kitten? Come here." She pulled him close and kissed him hard.
He melted softly in her arms.
Then he made a sound like a stifled sob and pushed her away.
"No!" he cried sharply.
But she held him tightly, caressing his ass, forcing her tongue into his mouth, and he surrendered, draping his wrists around her neck, his long blonde hair falling across his pretty face, his mouth open, his lips straining up to meet her lips…
Crimson felt his little penis stirring, half-hard, beneath his frilly apron.
"I think my little girl likes that," she smiled.
"I'm not a girl…" he mumbled.
"Well, you're certainly not a man." She pushed his pectoral muscles together, forming two little mounds of flesh that bulged up in her hands like women's swelling breasts. "Isn't that right, kitten? Wouldn't you rather wear a bra and panties and shake your big ass?" she whispered and played with his nipples until he grew dizzy with excitement and heard himself cry in a high-pitched voice that he didn't recognize.
"Oh, yes… yes, please!"
She laughed and squeezed his tiny penis.
"It's not much bigger than a clitoris."
"It get's bigger when it's hard…" he mumbled.
"Well, show me." She examined his pee-pee.
"What do you mean?" he licked his lips.
"You said it gets bigger. Make it bigger."
"You mean you want me to…?"
"Yes, that's right, sweetheart."
"Well, okay," he stammered and took his tiny penis in his hand and tried his best to get aroused; but for some reason he couldn't. And the longer he tried and failed, the more embarrassed he became, until in the end he was tugging at his limp wee-wee in a frenzy, close to pain.
"I don't know what's wrong!" he cried.
"Well," she reached down and took the little thing in her hand. "Maybe you're shy. Is that the problem?" she examined the head of his flaccid organ and pressed the little button of flesh back into his body so it basically disappeared.
"No…" he shook his head.
"Is my baby ashamed to have such a little pee-pee?"
Joyce looked down at his nearly neutered groin. The tip of his pee-pee barely jutted out from a neatly trimmed patch of pubic hair like a small rubber thimble.
"Oh, don't worry baby!" she squeezed his testicles together and made him wince in pain. "You can be Mommy's little girl. Wouldn't you like that, kitten? Wouldn't you like to be my little girl?"
He hung his head and nodded. "Yes…"
"Then tell me, you stupid cow!"
"Oh, Crimson…" he cried and wiggled his hips. "I want to be your little girl, I do… I do!"
"You're such a dumb bitch!" Crimson grabbed his tiny penis, and found it jutting hard between his thighs.
"Please!" he tried to pull away. "Let me go!"
"Why? What's wrong?"
"Oh, no!" Joyce gave her a quick frightened glance. Then he suddenly spurted in her hand.
"Oh, Crimson," his cheeks turned very red. "I'm so ashamed!"
He buried his face against her bosom.
"Don't worry, sweetie."
He trembled in her arms.
"Now put this on."
She handed him a pretty sky blue dress.
It was fit for a girl half his age.
"No," he said, "I'm not in the mood…"
"I don't care!" she slapped him across the face. "Put it on right now, young lady! Do you hear me?"
His face burned bright red for a moment. But then he saw that she wasn't kidding, and he didn't want to make her mad, so he did as he was told.
He slipped the pretty dress over his head, and Crimson helped button him up.
"There. Now put these on, Kitten."
She handed him a pair of white knee-high stockings.
"Please, I don't want to be a little girl again."
"What do you mean, again?"
"My auntie made me dress like this."
"Well, I'm not surprised."
She looked at him in his short blue baby doll gown, with his white knee-high stockings, his Mary Jane shoes, his long blonde hair elaborately curled around his blushing feminine face, and she smiled happily.
"Now don't you look sweet?"
"Please don't make me dress like this…"
"Why not?" she laughed and dragged him to the mirror. "Take a good look at yourself, kitten. See what you've become!"
Joyce stared in the mirror and saw what appeared to be a pretty young woman with curly blonde hair, dressed up like a little girl in a short blue puffy dress and petticoats, with her budding breasts pushed up by a satin bra which made them jut forward like two soft cones and bounce up and down whenever she moved. Her lips were red. Her pale blue eyes were accentuated by a thin eyeliner. Her pretty lashes were elongated by thick mascara. Her waist was pinched. Her body was nipped and tucked. And beneath her ruffled skirt, there was nothing but a smooth, compressed, feminine-looking mound.
"That's right, kitten," she rubbed his breasts and made them jiggle underneath the sheer material. "This is who you really are!"
"No, no…" he shook his head.
"You're a bad girl and you deserve to be spanked, don't you?"
He didn't answer.
"Don't you?" she repeated.
"Please don't make me do this…"
"Climb across my knee, kitten."
And, reluctantly, Joyce did as he was told.
"That's a good little girl."
She lifted the hem of his ruffled dress, and ran her fingers over his plump behind encased in a layer of tight pink nylon. She felt his little pee-pee pressed hard against her thighs. Then she lifted her hand and brought it down with a hard smack. The impact made his buttocks bounce and jiggle.
"Oh, no!" Joyce begged and squealed for her to stop. But she didn't stop. And he had no choice but to lie there, crying, until she was done.
"What do you say?"
"Th-thank you, Ms. Crimson."
"Give Mommy a kiss," she took him by the hand.
And he kissed her dutifully on the cheek.
"No, not there."
She made him get down on his hands and knees and kiss her ass.
"That's a good girl." She patted him on the head. "Now go to bed, Kitten. It's way past your bedtime."
* * * *
It was supposed to be a secret, just between the two of them. Something they did in the private. Behind closed doors. And never made public. Never go beyond that.
But then she took pictures of him dressed up like a little girl, with his frilly panties pulled down around his thighs, and threatened to show them to everybody at work if he didn't do exactly what he was told. And suddenly it wasn't a game anymore.
It was real.
"I expect you to do what I tell you to do," she instructed him. "And I expect you to like it. Do you understand me?"
Joyce unzipped his dress, worked it up over his head, and placed it on a chair. Then he unhooked his brassiere, unfastened his nylon stockings, and took off his garter belt. There was a scale in the corner near the closet. He pulled it out with his left foot and stood on it. Then needle wavered and steadied at 123.
"My god! This is awful! Crimson, I've lost 10 pounds!"
"Poor baby!" She pinched his bottom. It startled him and he jumped a little bit.
"Bad nerves, darling?" She smiled faintly.
"No, I'm okay."
"I say that because lately you seem a little blurred around the edges, Kitten, and frankly, dear – don't take offense – but your ass is getting so big and fat, you're beginning to look like a middle-aged woman, going all soft and rubbery. A well-made girdle would help you to pull in your tummy, precious."
"What's happening to me?"
Joyce hopped down from the scale and trotted into the bathroom, his fatty hips bouncing as he moved, and shut the door. Sitting on the toilet with his face buried in his hands, he desperately tried to regain his composure.
"Kitten, it's time to get dressed."
"Okay," he lurched to his feet and stumbled from the bathroom.
The clothes were on the bed.
Green bra and panties, denim shorts, a little peach colored tank top, and low heeled sandals.
"No peeking now!" he cried with a sort of frantic, giggling, girlish coyness.
Crimson, wearing a black satin bathrobe, leaned back on the bed and watched him as he struggled with his ruffled panties.
"Wait a minute, dear."
He straightened up and stared at her with apprehension.
"What's wrong now?"
"I was just admiring your ass. That's all."
He paused in the process of getting dressed, looked back over his shoulder, and touched his bottom.
"I thought you said it was getting too big."
"No, I like it that way."
"It makes me nervous."
"I know it does, Kitten." She patted the bed beside her. "Come here."
Joyce crossed the room and sat down beside her. The dim light softened his face. He looked quite pretty. His cheeks were flushed. His breathing very shallow.
"Don't you look cute!" Crimson snapped the elastic waistband of the panties against his smooth white tummy. Then she put her both her hands on his hips and told him to bend forward from the waist.
"I wasn't very nice to you last night, was I?" Crimson reached around and started to fondle his small pendulous breasts. "This time I'll be nicer."
"No, please!" He shook his head helplessly. "Really, please, I have a headache, and I don't think it's such a good idea to – " "That's right." She pushed him face down on the bed and began to play with his quivering ass. "You don't think. Do you, bitch?"
"Oh my God!" He turned his face away from her and began to whimper softly. "I must be going crazy…"
"No, you're not."
Suddenly, without any warning, Joyce found himself on the verge of tears. He got up quickly, eyes stinging, and sobbed.
"I'm sorry… please forgive me! But I can't! Not today!"
"Poor baby," she wiped his nose with a Kleenex. Then she tried to kiss him. "You're such a little girl…"
"No, please… no!" he whimpered.
"Suit yourself." Crimson frowned impatiently. Her face grew cold. "Stop bawling like an infant!" she snapped. "And put on some clothes, bitch. You look fat and ridiculous."
When Joyce was finally dressed, he looked in the mirror.
It wasn't that bad, just a pair of denim shorts and a little peach colored top, he told himself. True, the top had a lot of pearly buttons that ran down the back and it was made of raw silk, but otherwise it looked just like a sleeveless tee shirt. And everybody wore denim shorts these days. The only thing was that his denim shorts were cut very high and tailored in such way that they showed off his decidedly female shape.
"C'mon," Crimson took him by the hand. "We're going outside."
* * * *
She took him to a beauty parlor. It was small shop with several tall beauticians wearing white uniforms. They all clustered around him in a feminine knot and discussed what to do with his hair.
"I think bangs would be sweet."
"We should dye it platinum blonde."
"That would be lovely."
"And a perm," said Crimson. "I want him to have curls."
They gave him a little pink smock and told him to change into it. Joyce went into a small dressing room and took off his clothes. The smock was very thin and loose and had a little belt that made the garment flare out below his waist like a very short skirt. There was also a pair of pink plastic open-toed slippers with low but very definite heels that he was meant to wear in the beauty parlor. So he put them on and tried not to think about the girlish costume and how it made him look.
The slippers lifted his ass, which was already quite plump, and made it look even more prominent, so that he wiggled with every step he took.
One of the beauticians, a tall black woman with very short hair, took him by the hand and led him to a padded chair, positioned in front of a mirror.
"Sit there," she told him.
Then she gave a white plastic bib to wear. It tied behind the neck and made him feel like a child.
In fact the whole beauty parlor seemed as if it was designed to eliminate every last layer of his dwindling masculinity and leave him fluttering like a flower.
"Don't squirm," said the black beautician. Then she started to trim his hair. When she was done she set it in pink plastic rollers and gave him a fashion magazine to read.
The magazine was filled with pictures of beautiful women wearing gorgeous clothes. Joyce thought they were all very glamorous and wondered what it would be like to be a famous model.
Crimson sat in the chair beside him, getting her nails done.
"See, there's nothing wrong with being pretty."
"No, I guess not."
"C'mon, Kitten. You're already wearing high heels and curlers. Let's do it all. A facial, the works."
And, really, when he saw himself in the mirror, it seemed ridiculous to quibble about a facial when he already looked so feminine. "Alright…" he sighed.
"Good!" Crimson laughed and clapped her hands. "Girls, Kitten has decided she's in the mood for a total makeover. So give her what she wants."
Three beauticians descended on him like a flock of birds. One of them painted his nails. Another plucked his eyebrows. The other one slathered hot wax on his legs.
"Hey, wait!" he objected.
"Sit still," Crimson told him. "A girl has to have smooth, pretty legs. Otherwise she looks vulgar. Anyway, I've already paid them for the procedure. So be a good little girl and let them do what they're paid to do."
"You're going to get your legs waxed whether you want to or not. Do you understand me, Kitten? If the girls have to strap you down they will, darling. So you better just keep your mouth shut and cooperate."
So Joyce submitted to the treatment. And when they were done his body was totally hairless except for a little patch of pubic fuzz between his legs, trimmed in the shape of a small inverted V. The hair on his head was now completely platinum and fell past his shoulders in long pretty curls that framed his delicate face. With cherry red lipstick, black eyeliner, plucked eyebrows, and mascara, he looked completely female.
"Turn around, dear, let me see the full effect."
"Oh, my god!" Joyce hid his face in his hands. "What have you done to me?"
"What's wrong, Kitten? I think you look adorable."
"But how can I go out like this? Just look at me! What am I supposed to do?" he cried.
"Well, you obviously need some different clothes," she told him. "You can't dress like a boy anymore. That would just draw attention to yourself."
"What do you mean?"
"Well, pants are inappropriate, dear."
And so, reluctantly, he agreed to wear a pretty yellow sun dress that blossomed like a tulip below his waist, sky blue sandals, and carry a black vinyl purse.
"You look great!" Crimson kissed him on the lips. "Now what do you say?"
"Thank you, Crimson."
"Don't thank me." She instructed him. "Thank them."
After bidding goodbye to the women at the beauty parlor, Joyce reluctantly went outside with Crimson and started walking down the street. The sundress hung loosely from his shoulders and fluttered gently against his thighs. The breeze played with the hem of the skirt. It puffed between his legs and made him feel quite vulnerable.
"Don't worry," Crimson giggled. "You've got a great ass."
She pinched his bottom.
"Don't…" he begged.
"I can't help it, sweetie. It's just so big and sexy. I can't seem to keep my hands off it." She squeezed his butt and felt his flesh wobble softly beneath her fingers.
"Not here in public…" he whimpered.
"That's a compliment, Kitten, not a criticism. You should be proud to look so pretty," she smiled at him. "Now if only you had a real bosom… then you'd be totally convincing."
"I don't want to be convincing," he whined. "I just wanna go home!"
"Oh, c'mon, Kitten, why deny it? Wouldn't that be sexy? Wouldn't it be nice to have a pair of big soft titties that bounced and jiggled whenever you walked down the street?"
"No! I wanna go home!" Joyce cried in dismay.
"Well, if you insist," Crimson sighed. "But even if you won't admit it, you and I both know you'd look a lot sexier that way."
Then she hailed a cab and opened the door. Joyce got inside and crossed his legs. Crimson put her hand on his thigh.
"Relax, baby doll."
Back in the apartment, however, Crimson's public tolerance disappeared.
"How dare you talk to me like that in front of people! After all the money I spent on you!"
She slapped him across the mouth and pushed him against the wall. Then she put her hand under his dress and grabbed his little penis and yanked it hard enough to make him wince.
"Look at you… you're nothing but a big, fat, worthless slut!"
She squeezed and pulled his rubbery pee-pee until Joyce began to whimper and squirm. "Oh… no… oh… stop… oh… no!" And then, to his everlasting shame and to Crimson's equally clear delight, he started cum.
"I should cut it off." She raised her gooey fingers to his lips and made him suck each one. "What do you need it for?"
* * * *
"He's such a girl. You wouldn't believe it. Right now, he's wearing panties and a pinafore and he's doing the dishes. Yes, I know, it's a perfect relationship!" she laughed to her girlfriend, Alana, on the phone.
Standing in the kitchen, Joyce listened to the conversation in horror. He was mortified. But he had to admit, when he looked in the mirror, it was far easier to think of the small blonde haired figure in the pink cotton sundress as a girl than a boy. And that's what people frequently did when they talked to him, using female pronouns like, she, and her, instead of, he, and him.
His female co-workers all thought it was very funny.
"Are you sure you're not really a girl?" they laughed.
"Can I borrow a tampon, Joyce?"
Jokes he pretended to ignore.
But who was he fooling?
Every day he seemed to be slipping more and more into the world of bras and girdles, not baseball caps. And nobody seemed to care. All the women at the office seemed to want him wearing skirts. And the men just treated him with casual contempt.
Crimson constantly told him how sweet and pretty and sexy he looked in lingerie, and how grossly inappropriate he appeared in pants. Soon he was plucking his eyebrows and shaving his legs and painting his toenails all the time. When he walked down the street men looked at him and whistled. When he went to the supermarket the cashier called him, Miss. And when he went shopping for bras and panties with Crimson, all the shop girls smiled knowingly. For some reason it seemed like everybody wanted him to be a full-time girl.
"Well, you know, you look like a woman," Crimson told him. "You wiggle your hips and you mince around in dresses every chance you get, and yet for some reason you continue to think that nobody can tell you're a sissy!"
"Please," Joyce backed away from her. "Don't sat that."
"C'mon, admit it," she laughed. "You're just a pretty little fairy, dressed in a frilly bra and panties. That's all you are, baby doll. And that's all you'll ever be. So you better get used to it."
"No!" he cried. "It's not too late! I can be a man again! I know I can! I really can! If you'd just let me try…"
"Oh, sweetie, that's cute." Crimson kissed him on the cheek. "But why deny the obvious? You look nicer in a dress, and I like to see you wearing one. So be a good little girl and stop acting like a fool."
"But I'm not a girl!" he stamped his foot.
"Yes, you are," she explained. "You're my sweet little girl. And I'm gonna make you stay that way."
She jiggled his breasts up and down.
"You're nothing but a big dumb bitch!" She slid her hand between his legs. "And that's all you're gonna be for the rest of your life!"
"Oh… no… no!"
"Yes," she laughed at him. "I'm gonna teach you how to be a girl. Make you wear dresses all the time. And you're gonna learn to like it!"
Joyce's hips began to quiver and twitch; then a few drops of milky semen squirted from his pee-pee and dribbled down his thighs.
"That's a good girl," Crimson smiled.
* * * *
That night Crimson lounged in bed, wearing a black satin slip, reading a fashion magazine. She looked up and smiled at Joyce when he entered the room.
"Did you try on your new undies?"
"Did you try on your new undies?"
"Did you like them?"
"Yes… I liked them."
"Oh, you liked them?"
"Yes, but not the blue thing… I didn't like the blue thing very much."
"What blue thing?"
"You know, the, uh, nightie."
"Put it on," she demanded. "I spent a lot of money for that particular item. I want to see what it looks like."
Chagrinned, Joyce went into the bathroom to change into his new baby doll nightgown. He felt ridiculous when he pulled the filmy garment over his head and saw himself in the mirror.
A few minutes later, when the door swung open, he was silhouetted by the bathroom light.
He took a few shy halting steps into the bedroom before he stopped and stood there, a leggy blonde in a short blue nightie that swished and rustled against her thighs, golden ringlets framing her pretty face, and floppy white socks that made her look like a child.
Crimson wore a tight black skirt that ended just above her knees, a filmy white blouse, through which he could see the faint black shadow of her bra strap, and on her feet, black stiletto heels. She sat on the edge of the bed and looked at him.
"Now I want you to try and be a man for once in your pathetic life."
"What do you mean?"
"I want you to fuck me. Do you think you can do that?"
"Right now?" he licked his lips.
"Why? Do you have a problem with that?"
His legs felt weak and rubbery as he walked across the room. But they carried him, somehow, to the king-sized bed where he tried his best, despite his effeminate condition, to perform like a real man. But he couldn't even get an erection.
"Poor baby," Crimson ran her hand between his legs and played with his flaccid organ.
"I don't know what's wrong…" he mumbled.
"Sometimes I think my baby wants a big fat cock in her mouth. She does, doesn't she?"
"No, that's not true!" he protested.
"Don't worry, Kitten. Your secret's safe with me." She kissed him on the lips. Her lipstick left a bright red smear on his mouth, which only served to make him look more feminine. "I know you wanna suck a man's cock, don't you, baby?"
"No," he shook his head. "No!"
"C'mon," Crimson forced him down between her legs. "Suck my big fat cock, baby! Suck it! You stupid little bitch!"
And so he did as he was told, sucking and whimpering, as she banged her powerful hips against his resilient face until, finally, she arched her back and wrapped her legs around his head, and held him there, like that, clamped between her powerful thighs, until she was finally done with him.
* * * *
Crimson kept him high most of the time. And Joyce was too stoned on pot and booze to do more than sigh when she handed him a black satin corset and told him to put it on.
The corset firmly nipped his waist and lifted up his bosom. His body beneath the glistening garment seemed very pale and sensual. His smooth white breasts rose and fell with each shallow breath and jiggled with a female softness when he moved.
She looked at him and said, "I don't think of you as a man anymore. To me you're nothing but a dumb blonde with big tits and a sexy ass. That's all you are." Crimson reached down between his hairless legs and grabbed his little instrument.
"You stupid bitch…"
"Oh, oh, oh…"
"You ridiculous cow…"
"Oh… I'm cuming, I'm cuming!" he whimpered.
"You little faggot!"
He splattered in her hand.
"Now lick it up," she told him.
As he did, he caught a glimpse of himself in the mirror and started to cry.
© 2003 by Kitten. 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 express written consent of the copyright holder.