Chapter 35 : Johnny is dressed as a baby girl and kept overnight by Miss Williams

Aunt Barbara and Aunt Myrna delivered their weakened and feminized nephew to Miss Williams' apartment as it was going dark. She met them on the porch and relieved them of Johnny, assuring them that he would be deeply humiliated and chastened during his overnight stay with her. "It is my intention to take advantage of your babifying preparations," she said, slipping the bright red lightweight ladies' mackintosh from his shoulders and fluffing out the hem of his skirt and the lacy edging of his petticoat. "He will most definitely wish he had never displayed those transvestite tendencies that persuaded you both to sissify him ever since."
"We have complete confidence in your desire to shame him and develop deeper urges in him to dress in petticoats and panties," said Aunt Myrna. "Let's hope the girls will create a choice of uniforms which will meet his need for humiliation."
"I do hope you will attend tomorrow morning's assembly," said Miss Williams. "Your presence will add an edge of anguish to his misery."
Johnny's heart dropped on hearing this, and missed a few beats when his aunts accepted with delight and promised to be in school, where they would be welcomed at 9 o'clock. As soon as they left and the door was shut, Miss Williams turned on her unfortunate guest.
"Well, well, well... so you want to be humiliated and you want to be treated as a baby girl?" she said. Johnny's toes squeezed together, as did his stockinged knees, and he gave a nervous little nod. "Y-Yes please, M-Miss Williams."
"Well I have a rather special baby meal to feed you, my boy, for which you will be fastened into your high chair, so I shall have to dress you in a suitable babyish costume, won't I?" She took Johnny by the hand and led him into her bedroom, where his scalp ran cold with shock at what he saw: on all sides of the room were ruffled and lace-covered dresses, hanging from the picture rail and from every door and mirror and piece of furniture. Johnny saw in an instant that every one of them was a baby dress or toddlers dress, and he had a frightening feeling that they were all for him. His penis met this turn in events with a thrill of delight, and stiffened itself until it was upright and pointing out the front of the little pleated skirt he was wearing. As he was led to the bed, a divine dress of pale pink silk crepe shone beneath the ceiling light, with a deeply ruffled hem round the skirt and a wide Peter Pan collar with lace round the edge and embroidered into the wings of the collar. The sleeves puffed like pumpkins, with lace at each cuff, and a deep sash lay across the satin bed spread on either side. Arranged at the hem of the dress lay a matching pair of baby bloomers, trimmed prettily with the same pink lace, while above the neck of the dress lay a lavish baby bonnet laid on its side, with pink ribbons spreading away from its ruffled front edge.
Johnny held his breath as Miss Williams undid his skirt and slipped it down his legs, unbuttoned his blouse and removed his chemise and panties. His flesh rippled with pleasure as she fed the cold silk baby bloomers over his feet and slid them up his legs, over his erect penis and round his waist. There was a white nylon petticoat to cascade over his shoulders so that its lace bottom fluttered softly around the panty. He lifted his arms to slot them into each sleeve above his head, and the divine dress with its pink satin lining slid over his petticoat, caressing it in liquid feelings of feminine smoothness. Oh, how his rock hard penis longed to kiss the whispering silk and satin that surrounded it.
"Hand in here," she ordered, and Johnny found each hand encased in deep mittens of pink silk to match his dress and panties. He had never felt so babyish as when his mittens were being buttoned between ruffles of lace along the back of each wrist. She put him into pink silk bootees too, which fastened down the front of each foot in a line of pearled pink buttons surrounded with lace. His baby feelings swelled to a peak of excitement when he saw the frilled bonnet of pink silk approaching his head, lined in pale pink satin and dripping with rows of lace.
"Sissy baby girls," said Miss Williams as she drew the bonnet together in clusters of satin around his cheeks, "need to be reminded how infantile and impotent they are, so you will be masturbated with pairs of little girls bloomers while you are in your baby dress, panties and bonnet."
Johnny's cries told her how pathetic he felt already as she led him into the dining room where his pulse raced even more at the sight of his baby-girl high chair. It was covered in padded pink satin, gathered into balled shapes by ribbon done into bows at intervals from top to bottom. The feeding tray was pulled open, so that he could step a pink bootee onto the rungs that helped him climb into his chair. Once inside, he was closed in across his waist and Miss Williams took his bare arm, planted it along his armrest, and wound pink ribbon round and round before doing it into a bow. He was similarly fastened at his other wrist, then at his ankles, while lace edged straps of doubled satin wrapped diagonally across his dress to secure him firmly against the back of his chair.
"I feel so... weak," he complained in a wailing voice as Miss Williams adjusted his chair so that his legs in their ankle ribbons pulled wide to the sides, opening his legs to leave his stiffly pointed panties utterly exposed and available.
"You are weak, my little wimp. You're a baby and a sissy, and you will pay for your deviations by being conditioned into deeper, more extreme sissyhood." She spread a wide, waist deep baby bib over his breast and tied its ends behind his bonnet. Its back was pink silk like his dress, while its front was white plastic with pink words saying: ME WANT TO BE A BABY GIRL.
Johnny knew his penis was at its fullest, almost painful stretch, his panties so tight against his pre-cum wet helmet. He tried to brace himself against the coming baby bloomers, but was surprised to find that the Headmistress had sat on a high stool beside him and had placed a bowl of white cream in front of him. She mixed it with a spoon, then lifted a first spoonful towards his lips. The babyness of his dress, bonnet and widely spread panties made Johnny surrender to his baby feeding at once and he closed his lips over the spoon, sucking its contents and chewing its soft sweetness before swallowing it down.
"Good girl," cooed Miss Williams, presenting him with the next. "What a darling little sissy. Swallow your nice babycream and feel even more girlish... because this is a special mixture of girls hormones and stimulants to double your sexual desire for becoming more feminine and delicate." She gave him another spoonful, and another. "You will so want to become a little girl, Johnny, while at the same time suffering pangs of shame at your pathetic, unsexed condition."
Johnny wriggled in his ribbons, his panties sliding no more than an inch or two as he tried to pull them out of their satin seat, but it was no use. He swallowed the whole bowlful of the addictive cream down, and knew at once that he needed to be treated as a sweet little girl, even though he shivered at the humiliation he was likely to suffer as a result. Miss Williams put the empty bowl to one side, detached the feeding tray from the front of Johnny's high chair, and brought into his sight a pair of widely puffed silk sissy panties. They were cream with white lace edging, and white ribbons in bows at either side. His feeble emotions sounded as a gurgle of desire in his throat, followed by a wailing plea to be put into the lovely panties.
"Oh no, my little pet," chuckled Miss Williams. "I'm not going to get you out of your sissy baby chair, but your girlish little popsie can have its panties all the same... like this," and Johnny felt the cool silk legs of the panties spreading over his opened thighs as the silk slid over the pointed silk gusset of his own.
"There... panties to panties... over your clitoris, Johnny. Isn't that nice. Are you feeling morelittle girlish ?"
"Y-Y-Yes thankyou, M-Miss Williams. Ohhhhhhhh... s-s-silk panties-s-s..."
"Tomorrow you will come with me to school," she said, sliding the cream panty round and round on Johnny's defenceless pointed gusset, "and now I know you will beg my girls to make you a girl too... in dresses... and panties... and pretty petticoats. Am I right?"
"Y-Y-Yes, Miss W-Williams, I want them to m-make me a l-l-little girl... Pleeeeease."
When Miss Williams had brought him to the point of surrendering his sex to her panties, soaking them with the spurting sissy cream that oozed through his own panties, she withdrew them and then, allowing only a few seconds for him to recover, unfastened Johnny from his highchair. "There is no time to lose. You must be prepared for your baby crib, because tonight you will dream your deepest, most passionate desires into your mind and body, your thoughts and your nerves and your flesh."
She led him from the dining room to her bedroom, where a curtain decked with the dresses he had seen before was drawn back, revealing a deep cot layered in the bottom with cushioned quilting. He moaned from the pit of his stomach, partly in agonised humiliation, but also with shameful pleasure that this woman, who until a few days earlier had been a stranger to him, was going to put him to bed in the quilted softness as her own little baby girl. She sat on the edge of her bed and pulled him across her lap, so that he looked up into her strict face.
"Baby girls must be put early to bed, especially if they are going to be fitted with a pleasure giving device that will thrill them through their sissy dreams." His bonnet was unfastened and his wet panties were drawn down. She reached behind her and brought into his sight a piece of apparatus in soft latex, hinged down the middle so that it folded over on itself. It looked like white pvc on the outside with soft pink silky lining on the inside, and from one end there were ribbons to fasten it round the wearer.
"Baby Johnny's nice girly clitoris goes in here," she giggled, her lips curling with satisfaction, and his penis, hard again, was laid along the pink lining for it to be closed round it and clicked shut. The ribbons were pulled tight, securing the pleasure device at the very root of his penis as they were pulled round his waist and done into a bow at the back of his waist. It reached an inch beyond his helmet, which was purple and engorged with desire for being girlified at the hands of Miss Williams.
His panties were replaced with a plastic-coated diaper that she spread round his waist and up under his legs, taping it securely down each side. His penis in its pleasure device was closed inside. She unfolded a second diaper, slightly larger than the first, and wrapped it over the first, followed by another, and another. Over his feet she drew a large pair of rubber baby panties, which she drew up his legs and wrapped over his diapers.
"It's beddy-byes time, my little sissy girly," she said, leading him in his layers of diapers towards his cot. She lifted out the side and with a slither of pink satin, she opened out a large, full-length baby-sleepy-bag across the quilts on the soft rubber covered mattress. "Let's put my pretty little baby girl to bed, so that she can dream those desires that she longs for so much."
Johnny lay down in the middle of his opened sleepy bag and the satin sides were folded across him, gathered at his neck, and wrapped in a ribbon bow at his neck. The hood of his bag had buttonholes to match the buttons on the side of his pink bonnet, and they were buttoned through to ensure his head was enclose and smothered in girlish prettiness overnight. Then Miss Williams fastened all the buttons of his bag down to his ankles, where the bottom of the bag wrapped over and buttoned across from side to side.
"What a cute baby," she said, taking several photos of Johnny's blushing face in his bonnet and hood, before popping in a pink pacifier, which he began sucking on immediately. "But my little girl wants very pleasant sissy dreams, doesn't she? Let's fasten her up with lots of lovely, feminine desires for the night, shall we?"
From the ceiling she drew down a metal box and unwrapped a concertina tube from it which dangled onto Johnny below. "We just undo Baby here, introduce this nozzle here, inside the waist of Baby's panties... and diapers. We connect it here... and now we fasten her up inside her baby bag again."
Miss Williams stood over the cot, hands on hips, smiling with pleasure at her handiwork. Johnny's eyes showed complete acceptance of his condition. He sucked and moaned inside the satin lined hood of his baby bag, wanting nothing to change... feeling so completely feminine and childish. Then the pleasure device began its work.
His legs kicked and slithered in and out of the corners of his baby bag, and his penis grew in its pleasure as he remembered the dress he was wearing, as well as the roomful of lovely dresses that surrounded him. He was going to be a pretty, weak baby girl, and he would beg the girls at the girls school to make it come true. He swelled with blissful pleasure and his rubber baby panties felt so wonderful around his diapers and his gently humming pleasure giving device.

Chapter 36 : Johnny arrives at the girls' school for morning assembly.


When Johnny awoke, the memories of his final sissy dream were fresh in his head and in his private places; he was being strictly feminized by all the girls and women staff at St Gertrude's School. And there standing over him as he opened his eyes was the Headmistress herself, Miss Williams, who had just turned off the machine above his cot so that his delicious dreams came to a stop.
His legs slid around in his bag, finding places of cool satin that filled him with a sense of being dressed and babied again by the girls. Then he became aware of his panties. They were warm and wet. He had either peed himself in his dreams, or he had ejaculated time and again as he felt himself being dressed and undressed and laughed at by all the females of the school.
A bleat of horror escaped his throat and he sucked hard on his pacifier. It was Monday morning and he would soon be taken to school by Miss Williams, where he would be mocked and humiliated at the morning assembly, in front of his aunts.
"Yes, Johnny," she cried as she looked down on him and saw his sudden look of terror, "I am going to get you ready for your special day at school. Girls' school!"
A fit of trembling overcame him as he was unbuttoned from his cot, lifted out and carried to the bathroom, where Miss Williams undressed him and removed his rubber baby pants.
"I wouldn't be surprised if we find signs of baby wetness in here," she said with a grin of scorn, and she was right: his inner diaper was heavy with ejaculated cream, while Johnny's pleasure giving device was covered along its full length with sticky emissions. He had to be bathed, powdered and prettied with face blusher, eye make-up and lipstick, before Miss Williams put him into one of her own bras and panties.
As the time for school drew closer, Johnny grew more anxious, until Miss Williams stood him in front of her closet mirror to dress him for his appointment at the girls' assembly. She drew out a hanger with a little petti-half-slip in white rayon, edged round with two inches of lace. Next she produced the skirt he would wear: a little button down skirt in cream taffeta with lemon satin lining, but before she dressed him in it, she took out his blouse.
Johnny felt weak and collapsed at his knees, to be caught in Miss Williams' arms in a handful of blouse silk. She eased him onto the bed where he lay with his heart palpitating, and held up the blouse on its hanger, arranging it so that he could see its shiny collar and sleeves, its pretty pink stripes and most of all its clusters of pink blouse buttons. Surely the girls - his aunts too - were not going to see him in this!
But Johnny was powerless to resist as the blouse sizzled from its hanger and Miss Williams held it inside its large collar to present the sleeves to his hands. The humiliation he would feel at St Gertrude's came home to him and tears ran down his cheeks. His hands slid through the sleeves, and the blouse gathered onto his shoulders and over his breasts in rustles of silk, while the crisp, smooth silk of the striped collar wings slid around his smooth cheeks.
"I-I-I'm going to feel so ashamed," he cried in anguish as his sobs and tears flowed relentlessly. "It's such a s-sissy blouse, Miss Williams."
"Yes, just right for someone who wants to be a girl and lose all his sex... and probably wants to be laughed at too. Girls are very good at laughing at weak and sexless males, my dear little sissy. When they see you in your blouse, with pink buttons across your big breasts, I think they're going to get very excited."
The wretched boy cried and cried as he was put into his slip and skirt, and then into Miss Williams' own coat in pink wool. He cried a flood of tears in the car, all the way to St Gertrude's, and couldn't stop his tears when they arrived. In fact his wailing became deeply agonized as he saw a reception party of fifty girls gathered at the school gate, waiting to catch a glimpse of their 'new girl' to see what Miss Williams had chosen to put him in for the day.
A storm of laughter met him as he was pulled from the car by the headmistress, with no shortage of girls willing to help. She had chosen two of them on Friday to be the new girl's attendants, to dress and undress him both before the assembly and during it when he would be put into one schoolgirl uniform after another. Anita Foresken and Angela Kockfeel were at the front of the crowd, and each took hold of one of frilly Johnny's hands.
"Bring him into the assembly hall straight away, girls," said the Headmistress. "You can sit on either side of him in case he gets it into his head to make a run for it. He can sit in his nice blouse and skirt while the girls laugh at him until it's time for school to start."
That meant a wait of half an hour, and the number of girls pouring into the hall meant that the volume of laughter grew and grew. It reached a crescendo when Anita and Angela unbuttoned the front of his skirt, took down his half slip, and paraded their captive to and fro across the stage, with the stiffened point of his panties separating the sides of his skirt, so that the white satin gusset of Miss Williams' panties suddenly dampened, then grew white, then squirted droplets of cum as the girls made him stop with his legs wide apart and show everyone how a sissy ejaculates when he is dressed in really pretty and feminine clothes.