Chapter 5: Playing with the new family sissy

Simon suffered the deepest agony of shame he had suffered so far, on this horrific wedding day. He was exposed in his shame for Monica, his new bride to see, while her daughters, Sophia and Shannon, were thrilled to see him brought so low by the work of their wonderful grandmother. Worst of all was his weakness, his impotence, so that he couldn't resist anything at all that they might do with him. Not only was he dressed like a baby, he was a baby, begging to be allowed to kiss and cuddle with his mother-in-law.
  "This," said Veronica, fussing the bow of her pink and silver striped blouse now that her lover in a baby dress was fastened into his pink satin chair, "is the time for you to have fun with your husband, Monica. Remember he's yours to play with whenever you like, even though you've given him to me," and she chuckled at her maternal generosity.
  "I'm not sure that I want to play with the fool," replied her daughter, waiting for her giggling daughters to move up so that she could sit right next to the bundle of satin ruffles which was her husband in his dress and bonnet. "He's so ridiculous, aren't you Simon? And anyway, you wimp, you were telling me over the phone from my mother's room, that you loved her more than you loved me. I'm not so sure I want to be loved in second place."
  As she spoke, she worked his ruffled pink bloomers down from the waist until she could hold his uncovered penis in her fingers and fondle it in its ringed and secured condition. She giggled as Simon's eyes tried to deny what she was saying from above the edge of his white silk gag.
  "Oh but you can't deny it... I know it's true, thanks to Mummy's lustful ways with you, helped by Doctor Catherine's treatment. Isn't that right, Catherine?"
  The doctor giggled too, sitting alongside Monica's mother. "Unfortunately, everything I say to him about Veronica goes in and stays in, especially anything sexy and arousing." She put her hand on the baby's leg to draw his eyes to her. "Sissy Simon is so fond of his new Mummy, isn't he? He wants her to kiss and cuddle him... and dress him in pretty baby clothes... and most of all, Sissy... you want to have sex with your mother-in-law, don't you?"
  All eyes turned to the pink bonnet to see his reaction, since he couldn't speak. The helpless male lidded his eyes in floods of emotion and slowly nodded his big satin bonnet up and down.
  "Huh," snorted his bride, pulling herself up and throwing back her blond hair. "See what you're missing, you miserable little turncoat." She turned her bust towards him in its white see-thru blouse, her bra-less breasts thrusting at him into the chiffon. Her knees parted, so that the pretty lace of her see-thru panties revealed the shape of her pussy beneath her little black skirt, while her pantyhose lent a silver gleam to her shapely legs down to her sky scraper heels. "But you would prefer to play with Mummy... and be her baby girl." She gave his cock a squeeze. "So that's the way it's going to be. You can live upstairs all day and all night with your 'wonderful' mummy, and come down here in the evenings when we feel like having a good laugh."
  The bonnet drooped and wavered in front of her and Shannon looked inside at her stepfather. "Mom, you've made him cry again, look," and she lifted his face from under his satin bow so that they could see him sobbing, with tears glistening in his eyes.
  "Never mind, my baby," cried Veronica, grabbing him into her blouse again from the side. "You've lost your wife but you've got a mother-in-law... one who will dress you every day and night in lovely baby dresses. You should be grateful."
  "Yes," said Sophia, giggling. "And you've got stepdaughters who are going to play sissy games with you. Starting right now. What shall we play, Shannon?" Both girls crowded alongside him as he half lay back where Veronica had put him in his reclining sissy chair, both of them looking so like their mother, Shannon in particular, both of them blond and attractive.
  "There's only one thing I want to play with," said Shannon, her voice a girlish growl and her hair swirling across the shoulders of her lilac ruffled top, and she seized her stepfather's upright penis in both hands.
  "I guess we're going to have to take it in turns then," pouted her sister, "but while you're sucking, I'm going to be kissing," and she knelt between the edge of the settee and her stepfather's chair so that she could lean across his baby dress, her face looming into the front of his bonnet.
  Simon did his best to avoid these playful attentions, but he was strapped into his chair and had women's hands holding him still. As his penis slipped into Shannon's mouth, his bonnet came up instinctively, only to find Sophia's bare arms surrounding his neck and her lips probing any uncovered inch of his skin. "Mmm - mmm -mmmmmm!" she hummed, bringing passion to her kisses and hugging him more and more tightly.
  The result was felt inside her sister's mouth, where his penis thickened as was to be expected at the sexplay of eighteen and a nineteen-year-old girls. "Mmmmmmmmm!" echoed Shannon from around his penis, and the older women on the two settees giggled with pleasure, urging on the girls by smoothing the backs of their dress and top.
  "That's a lovely game, girls," laughed their grandmother, "and I'd say your stepfather loves playing it too in his pretty pink baby clothes."
"He definitely does," said Doctor Catherine. "He's nearly sliding out of his baby chair, he's wriggling with such pleasure." The girgling warbles, muffled by his pacifier and gag, told everyone that if it hadn't been for the two rings on his penis, at its root and beneath its helmet, Simon Barber would definitely have been squirting his cream down his stepdaughter's throat. His wriggles made Monica, Veronica and Catherine laugh all the more, which spurred their girls on to ply him with smothering kisses and sucks of deeper passion. While the sissy love play warmed up, Veronica's phone rang on the side table.
  "Hello... Oh Harriet, I was expecting your call... yes we've got him dressed and he's 'loving' it, so to speak, with a very stiff sissy cock. He's giving us a good laugh." Sophia withdrew her face from her stepfather's bonnet to listen, and Shannon sucked his cock in silence to get the gist of what was said.
  "Are you going to come over? ... With Mabel and Barbara?... Good, we'll have quite a party... we'll see you in a few minutes." She put her phone down. "Well, who's a lucky sissy husband, then? Three very nice and very female friends of mine are coming over to laugh at you."
A whimper of distress forced its way through his gag and his eyes held the most amusing look of sheer terror.
  "Oh but honey, they'll be ever so nice to lickel babykins. I expect they'll want to play with him and undress him, then dress him up in baby frillies again."
  "Oh...hee hee!" giggled Shannon, won't the sissy fool feel awfully ashamed, in his baby dress and bonnet... with women fussing all over him?"
  "Yes, and it's my turn to spread my mouth all over his stiff little whoopsie," cried her sister, and she threaded herself between Shannon and the baby's pink bloomers where they stretched from one of his thighs to the other. "Ohhh, Da-deee," she cried, wiping his erection with a kleenex before she got started: "I've got your effeminate little lollipop and I'm gonna suck it and suck it until I've sucked it off." She started immediately, while her sister put her face in her stepfather's bonnet and baby-talked him for a minute with lots of giggles before sliding her tongue inside his mouth and probing all over it.
  Veronica's friends made a noisy entrance. "We're here," announced Harriet, crying hellos to everyone as she was ushered in. "Oh my, will you look at him!" she laughed, and she held on to the back of a settee as her smokers cough took over her ample chest. When she gathered herself, she came round to join the action. "That looks like my kind of game you're having, girls. Can anyone play?"
  "We have to take it in turns," said Shannon, disengaging her face from her stepfather's bonnet, and out of politeness she refrained from burying her head inside it again so that she could talk to the visitors. Monica told Sophia to desist as well, so she sat up on the floor between the sissy's wide open legs.
  "Veronica darling, have you started putting him through all the training plans you had in that crazy head of yours? It looks like you have." Harriet Burrows was a headmistress, not long retired, who wore her hair in a big, blond style and was always immaculately turned out, as in the mauve satin cocktail dress she was in tonight.
  "He is Catherine's patient, dear. She has idiot where she wants him, well on the way to eating out of his mother-in-law's hand."
  "Have you given him something to keep him standing up like that, Catherine? Monica, you don't mind if I just hold your husband's lovely stiff cock, just for a minute?"
  Monica was sitting with her girls on either side of her, their knees hemming in the reclining sissy. "Don't ask me, Harriet. I've handed him over. But as you're here, that means you're part of the sissy teasing party, so you get to share all the fun."
  "Oh I'd love to play with the sissy," cried Mabel, who was almost twice the size of Harriet and looked it in a floaty cream chiffon dress. Her brown hair was in a short bob, but her make-up was anything but understated. "That kissy-sucky game you were playing when we arrived, girls... you'll have to teach us the rules so's we can all have a turn."
  "What about undressing the baby?" chimed in Barbara, sitting on the arm of the settee in a white dress with a purple floral design. "I'd love to take off his bonnet so that we can get a good look at his pretty sissy face, Veronica."
  "That's a good place to start," agreed their hostess. "I know you three would love to get your hands on him, so you can start now, and we'll pick another frilly costume for the sissy fool."
  The girls helped by unfastening their stepfather from his chair, and the visitors arranged themselves in a row along the settee. "What about your lovely dresses?" said Monica. You don't want splashes of spunk all over them. "Shannon, go and find some aprons from the kitchen."
  "No, no, we'll be all right having him across the skirts of our dresses," said Harriet as Mabel and Barbara stooped to lift the unhappy baby from his chair and hoist him round so that the three ladies could spread him along their dresses. His bonnet bow dissolved and his hair came into sight as they slipped the satin off his head.
  "We want this nasty gag off your lovely baby face, don't we, honey?" cooed Mabel, undoing it behind his neck. "Ahhh look, girls. Baby Simon is sucking on his binky like a good little girlykins."
  The three women faced him with their grinning lipstick as he sat up on their laps, sucking noisily for some unobtainable comfort. They admired his dress, fluffing it out round the edges and puffing the sleeves into picture book prettiness. But it had to come off, so he was laid down flat with his face in the chiffon of Mabel's skirt so that his back buttons could be undone. His panties were taken off his feet, and there were grunts of anguish as his stiff penis buried itself into Harriet's satin dress. Then he was turned and rolled this way and that for his dress to be slipped off, followed by his wide frilly petticoat. The girls joined in any way they could.
  "Da-deee, isn't that nice, having three lovely women undressing babykins? You're such a lucky sissy," said Sophia, kneeling on the carpet so that she could talk into his face. The women laughed and tickled their baby to rub it in that they were undressing him while he was too weeak and defeated do anything about it. Shannon knelt beside her, behind the arm of the settee. "The sissy likes you to play with his useless little cock while you're dressing and undressing him, Harriet," she said. "And he can't spray all over your dresses cos he's got it in rings in case of accident."
  "No, not in case of accidents," corrected their mother. "Grandma doesn't want him enjoying any sissy pleasures, that's why. Only when she wants to empty him out." All three women wanted to hold it at once, and there was a struggle as the sissy had to stretch his legs in an agony of excitement as hands played with him while his petticoat was undone for him.
  Veronica and Catherine came back in with their selection of sissy things for him. "Girls, make yourselves useful and spread your stepfather's baby things out along the back of that settee. Be careful of this dress, and don't let these petticoats slide onto the floor."
  Her son-in-law's flesh was coming into sight all over as his petticoat was slipped off over his head, and he sat up, held round the middle by Harriet and Mabel. Barbara undid the back of his pacifier ribbons and it was drawn out of his still sucking mouth.
  "Oh, ladies, please don't laugh at me like this. I feel so ashamed of being turned into a baby. I can't help being excited. It's... because of what happened with Doctor Catherine, and... Oh please have pity on me.... pleeease. "
  He was met with an burst of laughter from every female in the room, and Harriet held onto him as Mabel on one side and Barbara on the other jerked his cock up and down and the others watched. He wriggled, trying to lengthen his legs, then trying to get his arms out from between the women. "Ah look, he's too weak," sighed Shannon in mock sympathy, and she fell to her knees in her shirt-waister red and white dress and fondled one of his bare legs. "Ahhh, are all dese nasty women too strong for our helpless ickle baby stepfather?"
  More laughter, and more penis handling, until Veronica sat on the settee where his petticoats and baby clothes lay waiting. "Time to dress the baby," she cried. "When he's looking nice and pretty for me, then you can play with him again, and maybe get to play more of the sucky-sissy-kissy game."
  "Stop playing with him, Mabel," said Harriet. "I want to hold him steady for getting baby dressed nicely... don't we, Simon darling?"
  The crushed ex-male hung his head in despair. This was his wedding day... he was hopelessly weakened, stiffened by these women as well as by being dressed in frilly baby girls' things... and his wife was watching him, giggling with the rest. His arms were lifted and put through his first petticoat. It was gathered behind him, arranged evenly and fastened down the back. He looked down at the white silk bodice and the ruffled skirt that spread from a high waist, and tears welled unstoppably down his cheeks as he sobbed in the arms of the women. His tears renewed the giggles all round him.
  His second petticoat dropped over the first, similar but with little flowers embroidered on the front. The ruffles spread so widely, they made him feel unutterably girlish and his penis stiffened into his petticoat frills. His third petticoat had little puffed sleeves, which his arms were put into by Mabel and Barbara. It was gathered around him and his petticoat buttons were done up for him at the back. By now his shame was so great that he was crying out loud, drawing coos and cries of sympathy from all sides with mocking grins on every face he looked at.
  The girls helped to put him into bootees of lemon satin, fastening across the top of each foot with inch wide ribbon. Monica lent a hand in his dressing too. She got to show him his lemon satin baby bloomers with deep ruffles round the back and lace at the bottom of each leg. She fed his bloomers up his legs for Mabel and Barbara to pull them into place as Harriet lifted them. His erection slid into view through a frilled sissy penis slot, drawing an outburst of more laughter from his circle of tormentors.
  Catherine put him into his pair of baby mittens, in lemon satin to go with his bloomers and bootees, and then it came to his dress. Poor Simon Barber wailed with misery as it was lifted from the settee by his mother-in-law and held up for everyone's delight. In bright yellow satin, it had a high yoke, with tiers of flounces spreading from it into a very wide skirt which must have measured less than three feet from neck down to hem. Each sleeve was a wide puff of satin with a ruffled cuff, and between them was a pretty Peter Pan collar in lemon satin with a scalloped edge all round. When she turned it, the wide sash ribbon hung to the floor from the edges of the skirt, and the dress had three little buttons above the yoke to beneath the pretty collar. What was so amusing for the women was the look in his big staring eyes; the de-sexed fool obviously longed to be dressed in it.
  His arms were lifted to meet the sleeves, then the sizzle of silk and satin sent frissons through his body as the dress dropped over his head and slid onto his petticoats. Everyone wanted to straighten, arrange, slither the lemon satin around him... except Sophia, who realised that his bonnet would follow and she wanted to put him into that.
  "My turn," she cried, as everyone surrounded the baby in his dress. She stepped into the middle, separated the two sides of the soft bonnet in doubled lemon satin, and drew it down onto his hair until it surrounded his weeping face.
  "Oh no... please no..." they just about heard as his weakened voice pleaded for mercy.
  "That's right, sissy... cry for Sophia, like a helpless little baby girly," and she tucked his hair into the sides of his bonnet, then gathered it as he shook with sobs and did it into a big bow under his chin. She stayed in her front position, surrounded by women, to survey their handiwork, spreading out his petticoat and dress ruffles and tucking at the front edges of his satin bonnet.
  "I think Da-dee is going to have a lovely evening in his new satin baby things... with so many nice women around him to play sucky-sissy-kissy across our knees."