Simon Whitely knew the tears would roll any moment down his cheeks, smudging the mascara his stepmother had just brushed onto his lashes, because once again he found himself in a punishment costume. He ached with shame in front of the closet mirror as she looked over his shoulder to brush through the sides of her own brown beehive, her jaw set with hard, stepmother resolution as she checked that he was suitably chastened and miserable. "Lift your chin," she ordered. "Turn your head to the side, now the other side. A girly boy like you should be checking how pretty you look with pretty bangs and sweet teen make-up."
Simon had to do as Jessica said. Since she married his father and entered his life, each day had become a misery of obedient service and crushing humiliation. Right now his father was upstairs doing the housework – in his maiding uniform, his punishment for being unable to satisfy his new wife in bed the night before. It was becoming a frequent arrangement, which told Simon either that his stepmother was extremely demanding, or that his poor Dad was too weak and couldn't match up.
A bit like Simon himself. "That's what wimpy boys get for being so effeminate," she cried, making him jump, and the tears did begin to flow as his nose filled and the sobs began to make the little frills round his blouse collar tremble at his cheeks. Why did he have to suffer such an agonizing daily life of shame? Why did she choose such awful clothes to punish him in: a little girl's white blouse with puffed sleeves at his shoulders and a pink and white gingham skirt. "Well I can tell you this, my boy," she went on, stepping into the pleated skirt of her apple green suit and sliding it up her slip, "your life is about to change because I've had enough of all this male pretending, from you AND your father: as far as I'm concerned, Simon Whitely, you are a girl."
The boy burst out crying. What misery! For a nineteen-year-old! To be dominated and controlled by his stepmother, and made to dress in such demeaning costumes. His tears meant that he almost missed the ring of the door chimes. Oh no, surely not someone who will come into the house and see him like this! "Stand at the mirror," she said, "and practise holding your hands sweetly with your skirt held out in your fingertips." She pulled on her suit jacket on the way to the hall.
His anguish sank to a new low. That voice, and his stepmother's laughing greeting. Of all people who might add to his painful embarrassment, it was her sister. They'd stopped giggling by the time they came in and discovered the sissy standing to admire himself in the mirror.
"Turn round and show Aunt Judith how pretty my stepson looks in his blouse and skirt," he heard, and his heart sank as he did what he was told. Judith was wearing a blue suit with a narrow skirt to below the knee and a pretty flared coatee with white collar and cuffs. She'd had her hair done in a short style off her neck so that she looked even more like an efficient schoolmistress than usual. He wilted under her gaze.
"But I'm a boy, Aunt Judith. Please ask Mummy not to dress me like this."
His 'aunt' snorted. "Look at you;" her voice was firm and level: "wearing a girl's white socks and patent shoes. What has he done to deserve petticoating, Jess?"
"I found his secret little store, hidden deep in a drawer of his dresser: girls' make-up."
"Ohhh! For goodness sake: if he's that girlish he has to be kept in either a dress or a skirt, with petticoats."
Both sisters glared at him in his shame and he hung his head, wishing he could disappear or run and hide. Both options were useless: Jessica was merciless in her petticoat chastisement, and that included spanking him in her panties and petticoats in front of his father. Then she walked to his punishment closet and reached inside to pull out more misery for him.
"Your Aunt is here for a purpose, Simon. I've been speaking to a lady about you and she has agreed to help. We're taking you to her this morning."
These words brought panic to her stepson, especially when he saw what she had in her hands. Girly frills and dainty lingerie, and something in shiny peach pink satin. He had to stop himself from crying again in front of Aunt Judith: she would think he was a baby. His lips trembled as she took him by the arm and marched him to the bed where his new clothing awaited him. Oh the shame, as his stepmother's thirty-five-year-old sister undid his skirt and took it off him, then his blouse. He squeezed his eyes shut in misery as if to close it all out as his underwear was removed and he stood naked between them to be dressed in girls' clothes.
"This is what you need, if you want to do a girly make-over," said Aunt Judith. He held his hands out, the sobs rising in his throat, as the little white training bra was slipped up his arms and hooked together behind him. His stepmother had arranged two separate petticoats on the bed-spread, both in white chiffon and extremely short. Then he realised how horrifying they were: they weren't waist slips, but full slips with shoulder ribbons, only each of them was no longer than thirty or forty centimetres – not reaching his waist! The first one did up between his shoulder blades with two little ribbons done into a bow: the second fastened with three petticoat buttons at the base of his neck. Then the peach satin: it was a dress: a little girl dress, or was it for a baby? It had a pretty frill all round the hem and he felt his cock aching with stiffness and sweetness as it fell over his hair and sizzled round him as his arms went through the wide puffed sleeves. "That's right," affirmed his stepmother, buttoning him down the back. "Sissy boys who like to play girly make-up have to wear little girly dresses to be taken out in." His Aunt fussed the front of his dress and petticoats, a curl of disdain on her crimson lips. Simon clasped his face in his hands. How could they be so beastly as to dress him as a little girl between them. His stepmother reached her arms round him.
"Now we have to dress his sexless parts," she said, drawing together the ends of a pure white suspender belt and hooking them together in the small of his back. His Aunt pushed him back to sit on the edge of the bed and took a pair of seamed white stockings from a sellophane packet, letting them drop into their delicate see-thru length from her fingers. She and his stepmother fed a hand into each stocking and they crouched at his legs to thread them over his feet and slide the fully fashioned hose up his legs, until they enclosed his flesh and pulled it tight, with clip after clip fastening him into excruciating girlishness. They looked into his face as they took a pink satin shoe each, with sky-high heels, and he squeezed his eyes shut as his feet were clad as if he was a girl.
"Open your eyes," said his stepmother, "and look at your girls' panties. Yes, pink nylon, very dainty and very sweet, to cover your little places, to make sure they feel feminine like a girl's. The reason you need to be girlish, dear boy, is because of where we are taking you: a place for boys who are to become girls, whether they want to or not." Both of them stood over him as he sat on the edge of the bed in his little dress and petticoats with his panties on full show and his white stockinged legs with pink high heels. Judith had her lips pursed in a satisfied sneer. "It's called 'Sissy-Me'," she said, "and Miss Bowes the Head Mistress is waiting to meet you."
"When I told her how you stiffen up," said Jessica, "when you are put into punishment costume, she couldn't wait to get hold of you. You're going to spend six hours a day at Sissy-Me, so you'd better get used to it: just try being the girl you were meant to be."
Simon let out a wail of helplessness. How could he avoid this terrible fate? Why were they being so cruel to him? What if other people saw him walking through the streets like this, he wondered as he was marched out of the house and along the street? He didn't have long to wait to find out.
"Oh isn't he a doll!" cried a woman's voice in front of them. It was a voice he recognised: Missus Sweetly from church. She was wearing one of her church hats and a pale green costume with a narrow skirt. "I love him in that cute dress with frothy petticoats, Jessica. But why have you dressed him like this? Did he deserve it?"
"I think he's the best one to ask, Iris."
Simon squirmed his knees together as the woman looked him up and down. "Did you do something to deserve being girled?" she asked, standing up close and feeling the lacy edging to his petticoats. Her eyes glanced up into his, expecting a reply.
"I-I bought myself some girls' make-up, ma'am."
Her mouth dropped open. "Oh my goodness! Do you want to put it on?
Simon tried to hide his nodding. "Y-Yes, ma'am."
"But why do you want to put on girls' make-up, Simon?"
He could hardly breathe and had to force out his words: "B-Because I want to look like a girl in the mirror."
"Do you mean with pearl-like eyes and shiny lips?"
"And smooth, perfect skin like girls have?"
"Yes ma'am – but I'm not a girl, I'm a boy and I should be wearing boys' clothes."
Two other women had approached and showed alarming curiosity in him. "Excuse me, ladies," said one of them, wearing a blue coat-dress: "is he a sissy?"
"Is he being sissified?" the second woman wanted to know. She was older than her friend and wore a smart beige suit. "I'm Deirdre Girling and this is my friend Marilyn Fullslip. We're very interested in boys who want to wear girls' clothes." Their eyes scrutinized Simon and his costume in every detail, with smiles on their lips as they tried hard not to burst out laughing.
Simon turned himself right round, almost as if to show them the buttons at the back of his little dress, but really to hide the wail of shame that he was trying to smother. His stepmother and her sister were having none of it, though, and turned him back. They held his hands so that his arms were spread out to the sides, showing his short smocked dress in all its detail. All he could do was turn his face into one of his puffed sleeves to hide his crying, but he knew his panties were alarmingly pointed under the close scrutiny of all three strangers.
"I approve of boys being disciplined in petticoats," said Marilyn Fullslip. "I used to put my own son into girls' dresses whenever he showed cowardice or weakness, which was once or twice a week. All his friends knew he had his own punishment closet at home, which was opened regularly for him to be put into panties, a petticoat and a girls' dress."
"And I approve of it too," added Deirdre Girdling, "particularly when a boy shows how effeminate he is like your son has done. Maybe he deserves more permanent dressing, to show him he should be treated as a girl."
Jessica smiled her approval. "That is something which might happen sooner than he thinks," she said. "Because we are on our way to Sissy-Me with him, and Miss Bowes has ways of making a boy feel more and more like a girl from the moment she sets eyes on him."
"Sissy-Me? Oh how wonderful," said Missus Sweetly. "Can we come along with you, just to make sure that he gets taken inside? I hear that boys who are taken in there are never the same again."
Her words struck horror into Simon's heart. "Wh-What do you mean, ma'am? What will happen to me? What will Miss Bowes do? I want to go home, stepmother, pleeeeeease!"
Jessica and her sister had to use a little more force to drive the sissy in the direction they wanted, with his stepmother locking his arm in both of hers and Judith clamping his other arm to his side as she pushed him firmly forward.
"No! Please! I don't want to be girled!" was his constant plea as the dreaded sissy school came into sight and the yards between were relentlessly eaten up in stumbling and sliding.
"You're nearly there now, Simon," he heard from Missus Sweetly behind him. "Your days as a boy are almost over."
"You're going to be dressing yourself in skirts and dresses from now on," cried one of the other women."
"Look at him suffering," cried the other. "Oh look, he's wetting himself."
All the women looked, and it was true. Simon Whitely had reached such a pitch of shame and fright that his efforts to hold onto his wee couldn't match his irresistible urge to urinate, deep into his panty gusset. He was still trying to hold it when the door of the establishment opened and a blond woman in her forties with sharp features, a cream frilly blouse and a wide skirt of pink pleats came out towards them. He suddenly felt indescribably girlish, all weak and pretty, as if his dress make him just the sort of little girl who belonged in Miss Bowes' sissy school. And her skirt: it swayed and bounced on unseen depths of petticoats, floating round her legs and bouncing towards him.
"I'll put him into this," she said, holding a looped combination of white ribbons. "Sissies who aren't too sure of their sex find it helps to have their clitoris cupped into a pretty girl's purse of pink fur with bobbles." His heart stopped as he watched her grasp the waist of his panties and unhook it from his erected cock. There were gasps from the women, which became whoops of alarm as a little spurt of white cum popped from the engorged head into the air. She fed the fur sleeve over it, sliding its latex lining down to his root in a single pull, where she wrapped satin ribbons round and round his testes to hold it in place.
"There," she said, securing the straps round his waist and snapping the lock together. She had silenced him into a sort of suspended squirm as his groin and cock swelled with pleasure. "Now you can feel like a girl in her clitoris, because that's how you are going to be from now on, dear. Say goodbye to your stepmother and the ladies, and come with me into your new girls' school."
She held the leash in the fingers of one hand, not needing the slightest force, since the merest tug of the ribbon on Simon's pink purse brought him toddling on his heels and toes after his new Head Mistress. 'Sissy-Me' it said above the doorway as he followed her inside, and as she turned to close the door on the outside world, his wish for girly things grew to a helpless climax and his clitoris pumped all his desires for girlishness into his pink, fur sissy-sleeve.
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