“Hello Sweetie, is Mommy taking sissykins for walkies, darling?” chirped a young blond with a gleaming smile of contempt.
“What a bee-oo-tiful pink cape Mommy has you in, sissy,” said the red-head who walked arm in arm with her. “With very fashionable white edgings, and a baby bonnet to match!”
Samuel dipped his bonnet lower, trying to hide his crimson cheeks inside the deep, stiffened wings in a floral pink print, lined around his face with snow white satin. There were more comments: “Are you wearing Mommy’s bra and panties, dearie?” and “I expect you’re wetting your diaper inside those lovely pink panties, honey.” Samuel kept his eyes demurely down the front of his plastic cape, ignoring the women’s giggles and trying to close them out as he planted one high heeled shoe in front of the other, with occasional prods from Thelma in the middle of his back.
But as he blotted out what he heard in the Mall, his mind filled itself instead with awful recollections about how his chances of a wonderful life had crumbled before him, and all through no fault of his own. At least he thought he had done nothing wrong: his wife and her mother took a very different view.
He thought he had secured a lifetime of bliss by hitching up with a really attractive model in Thelma Golding. She may be a few years his senior, but he had always liked being ordered about a bit by his mother and sister as a kid, so her arrogance was an added attraction in his eyes. Unfortunately for him, that superiority she displayed turned bitter in his mouth as he tried to relish the early hours of their newly married life. When a submissive groom tries to satisfy a bride who is clearly superior in every way, his strength, his confidence, even his very manhood, can quickly let him down. From adoring his idol up to the moment of final consummation, all his powers and functions, small as they were to start with, deserted him. There was no way he could produce an erection, a misery which relayed itself immediately to his beloved.
“Get up,” she cried, spitting venom as she pulled on a negligee; “on your feet, as you are” – he was naked of course – “and get to Mother’s room.” The shock of finding he couldn’t erect for his bride was more than doubled as he found himself standing at the foot of his mother-in-law’s bed as she put her feet to the floor and stood up wearing one of her knee-length nighties in softly translucent peach nylon. Vanessa Golding was a beauty herself, very aware of her looks and careful with her golden hair. She listened with a face like thunder and passed the first of many sentences on him that would transform his life from male to – well, to what he had quickly become.
“He’s a sissy, obviously,” she declared. “Darling, you’ve married a sissy, and I am going to make him pay.” She stood with her closet door open. “You, come here. If you can’t be a man in Thelma’s bed, you’ll be a woman in here. You can sleep in my alcove bed opposite the window.” So Samuel Bending found himself being tucked into the satin sheets of his Mother-In-Law’s spare bed, wearing one of her nightdresses in lilac organza with delicate panties to match, and having curtains of pale pink gossamer drawn all round him to enclose him in what would soon become his new feminine condition.
His descent into sissy dressing was rapid: every night he was dressed in Vanessa’s bedroom as she put him into one of her bras and panties and dropped one of her nightdresses over his head. “It’s essential that we keep that penis encased in femininity,” she declared as Thelma helped to towel his hairless groin after they had given it its early evening bath, followed by sprays of Vanessa’s perfume. “So I’m going to keep it in one of my girdles each day: a severe one, and that means stockings on his legs, and I want him in heels to denote how his sex is female, not male.” This arrangement soon became a different girdle or corselet for him each day.
It became clear to Vanessa and her daughter, or so they claimed, that he was making no progress, in fact his sexlessness became even worse, so common sense dictated that they should treat him as an effeminate wimp. Each morning, after his bath and make-up, he was put into a pair of Vanessa’s panties over her girdle, with a petticoat slip and a skirt. “That penis area must be feminized,” they agreed: “if all his feelings are feminine in that area, it should show no signs of masculinity.” He would sit opposite them dressed like this as they lectured him about how he should do this and that to improve his manliness. “It’s just as well you’ve shared your goods and assets with Thelma,” said Vanessa, her mouth pursed with disdain, “and therefore with me, because you won’t be going anywhere trying to hold down a job in your impotent condition.”
Samuel Bending often wept a private tear about his condition, but his wretched life soon settled into this semi feminine existence, female from the waist down. Unfortunately for him, the blow to his male confidence meant that it wasn’t long before he began wetting himself into Vanessa’s pantie-girdles. The first time he got away with a harrowing scolding from wife and Mother-In-Law. The second time, however, Vanessa made a decision. “We’ll have him in diapers,” she pronounced, “with appropriate little girl blouses and a little skirt.”
Samuel’s heart was ready to burst, he felt so humiliated as they dressed him in his new uniform. This soon became a blouse and pinafore dress, made for him by Mademoiselle Chenille, Vanessa’s couturiere. This step towards becoming almost a little girl, almost a baby girl, was the signal for Thelma to develop a much harsher attitude of impatience with him, showing itself in her using a whipping cane, while Vanessa used a slipper on his naked backside for the slightest shortcoming before taping him up again inside his diaper. This meant several spankings a day. It also led to double girdling: they dressed him in corselet and panty girdle over his Pampers. The result: he looked pretty heavily padded inside his wide plastic pants. For some unknown reason he found it pleasant to be treated so firmly by two determined women. He felt a new, lovely excitement when they had him tightly confined inside his padded diaper, and especially when they treated him as a female – their naughty little girl.
“If you don’t shake yourself into proper manly behaviour soon,” cried Thelma as she pulled ruffled pink baby bloomers up his legs and over his plastic panties, “I’ll take you to a sissy club I’ve found in town.”
“How long are you giving him,” asked her mother, “to change his ways?”
“Until Friday, if not, he’s there on Saturday morning.”
So that was how Samuel Bending found himself stepping through the door of Sissy Kissy dating club at half past ten in the morning. And for some reason Gaynor and her mother had relieved him of his girdles so that he was wearing just his Pampers and plastic panties under his petticoat and the most emasculating pink and white dress Mademoiselle could have created for the occasion.
They were met by Miss Titswell who is in charge of welcoming nervous newbies. “The best way to get used to being a Sissy Kissy Panty Boy, darling, is for me to introduce you to another Kissy Boy,” she said. “Come with me into this nice kissing corner where someone very effeminate and just as babyish as you is waiting to give you lots of warm, wet kisses. Ms Golding, I have your sissy’s name drapes ready for him to wear, from his wrists to his ankles, so that everyone can see who he is.” A smile of female amusement played on her lips as she held out a roll of shiny pink material and let it drop from her fingers into two banners which displayed gold lettering announcing “SWEETIE SANDRA”.
Samuel could barely see through the tears that filled his eyes as he stood with his knees trying to press together while his wrist ribbons were attached for him. What a shocking name to be given. How humiliating to be put into lacy edged panels that showed just how pathetic he was in his wife’s power. They were joined moments later by a lady who was introduced as Missus Gaynor Smoothley, and she held the hand of a darling, shy-looking little girl, who was perhaps a little bit older than she looked.
“This is Melanie Mummypet,” Miss Titswell told them. “This is her first day too and she is learning how nice it is for sissies to kiss each other. Open your arms, Melanie sweetie – you too, Sandra, and I want to see you both enfolding each other into your dresses while you meet each other’s faces, cheek to cheek. Ahhhhh, that’s lovely, my darlings. What a good start you are both making.”
Samuel, or Sandra as he now was at Sissy Kissy, felt this strange girl’s fingers fondling him on the outside of his bonnet, pressing their faces together, but Miss Titswell was happy with that for only a minute or two, and wanted Melanie to draw back, to find the open front of Sandra’s bonnet, so that their anxious eyes met in the intimacy of Sandra’s bonnet wings. Their lips were soon touching softly, lipstick on lipstick, smoothing together. Sandra felt that excitement again in his Pampers, as if he was naughty for feeling sweet and helpless as Thelma’s little girl. His lips puckered and pressed, and moments later the sissies moaned with emotion, sliding their lips over each other.
It was time for their Mistresses to take control, standing right behind the two little girls, pressing their dresses and pantied bottoms with thrusts from their hips, arranging their hands and arms in a dainty, warm embrace. Their lips parted and touched again, becoming closer, wet kisses, and as the sissies bleated and whimpered inside Sandra’s bonnet, they felt their dresses being lifted for them so that, in a sudden thrill of pleasure, their genitals slid together bringing a rosy ache of stiffness to their pantied, rigid cocks. Sandra moved his helmet to and fro, trying to find the corresponding knoblet of his new girlfriend. He found it, stiff but somehow soft and feminine, and his passion swelled. The sweetness was intoxicating, no tears now, just kissing lips, tongue finding tongue in wetness and warmth and girly pleasure, and into his lovely Pamper softness he surrendered an escape of juicy girlishness, followed by another, more urgent squirt, until he spent and spent his girly love and pleasure onto Melanie’s lovely cockie through the layers of their diapered panties.
As Thelma pulled him apart, convinced she had a pure sissy for a husband, he lowered his eyes in shame and begged, in a tiny girly voice: “Please darling, oh please can I kiss Sissy Melanie again, just one more time?”
But Miss Titswell was on hand to intervene. “Certainly not,” she declared. “You and Mistress Golding will come with me because there are other sissies whom you are going to kiss, again and again and again while you are here for your Saturday training in Sissy Kissy Panty Boys.”
* * *
All Prim’s stories are at www.primspetticoatwendyhouse.com where members get EVERYTHING AT ONCE for a monthly subscription.