Aunt Rose and Aunt Mavis delivered their weakened and feminized nephew to Miss Duffs’ apartment as it was going dark.
She met them on the porch and relieved them of Jamie, 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 Mavis. “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 Duff.
“Your presence will add an edge of anguish to his misery.”
Jamie’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 Duff 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.
Jamie’s toes squeezed together, as did his stockinged knees, and he gave a nervous little nod.
“Yes please, M-Miss .”
“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 girlish costume, won’t I?”
She took Jamie 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.
Jamie 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.
He met this turn in events with a thrill of delight.
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.
Jamie held his breath as Miss Duff undid his skirt and slipped it down his legs, unbuttoned his blouse and removed his chemise and panties.
His flesh rippled with joy as she fed the cold silk baby bloomers over his feet and slid them up his legs.
There was a white nylon petticoat to cascade over his shoulders so that its lace bottom fluttered 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.
“Hand in here,” she ordered, and Jamie 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 bootees too, which fastened down the front of each foot in a line of pearled pink buttons surrounded with lace.
His babyishness overcame him as soon as 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 Duff as she drew the bonnet together in clusters of satin around his cheeks, “need to be reminded how infantile and impotent they are.
Jamie’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 Duff 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 against the back of his chair.
“I feel so helpless,” he complained in a wailing voice as Miss Duff adjusted his chair so that his legs in their ankle ribbons pulled wide to the sides.
“You are helpless, 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:
“I want to be a baby girl”
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 mixes it with a spoon, then lifted a first spoonful towards his lips.
The babyness of his dress, bonnet and widely spread panties made Jamie surrender to his 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 Duff, presenting him with the next.
“What a darling little sissy.
Swallow your nice babycream.”
She gave him another spoonful, and another.
Jamie 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 messy cream down, and knew at once that he wanted to be treated as a girl, even though he shivered at the humiliation he was likely to suffer as a result.
Miss Duff put the empty bowl to one side, detached the feeding tray from the front of Jamie’s high chair, and brought into his sight a pair of widely puffed silk sissy undergarments.
They were cream with white lace edging, and white ribbons in bows at either side.
His emotions sounded as a gurgle of desire in his throat, followed by a wailing plea to be dressed in them.
“Oh no, my little pet,” chuckled Miss Duff.
“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 Jamie felt the cool silk legs of the undergarments spreading over his legs as the silk slid over the pointed silk gusset of his own.
“There – Jamie.
Isn’t that nice.
Are you feeling more sissy?”
“Yes thankyou, Miss Duff.”
“Tomorrow you will come with me to school,” she said, sliding the cream panty round and round,
“and now I know you will tell my girls that you want them to make you a sissy too – in dresses – and panties – and pretty petticoats.
Am I right?”
“Yes, Miss-Duff,
I want them to m-make me a little sissy – Pleeeeease.”
Miss Duff unfastened Jamie 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 drew 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 pleasure that it was for him, and this woman who until a few days earlier had been a stranger to him, was going to put him to bed in it as her baby sissy.
She sat on the edge of her bed and pulled him across her lap, so that he looked up into her strict face.
“Baby Sissy’s must be put early to bed,”
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,” 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-sleep-bag across the quilts on the floor.
“Let’s put the little girl to bed, so that she can dream those desires that she wants so much.”
Jamie lay down in the middle of his opened 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 enclosed in girlish prettiness overnight.
Then Miss Duff 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 Jamie’s blushing face in his bonnet and hood, before popping in his pacifier.
But my little girl wants pleasant dreams, doesn’t she? Let’s fasten her up with lots of desires for the night.”
She drew down a metal box and unwrapped a concertina tube from it which dangled onto Jamie below.
“We just undo Baby here, introduce this nozzle here.
We connect it here – and now we fasten her up inside her baby bag again.”
Jamie’s eyes saw all that she did, but it didn’t really matter.
He sucked and dreamed inside the satin lined hood of his baby bag, wanting nothing to change, feeling so feminine and infantile.
Then it began.
His legs kicked and slithered in and out of the corners of his baby bag, 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 baby sissy.
