The story so far:
James Conningsby has lost his father who has run off with his secretary. The boy's stepmother, Vanessa Mandridge, is determined to take full revenge on her stepson. The innocent boy gives her a huge advantage in feeling deeply attracted by her sexy blouses, skirts and lingerie. Her friend Bernice will act as the boy's governess during a process of deep seduction. In Chapter 2, another friend of Vanessa's, Alma, overwhelms the sexuality of James' friend Tristan, while a third friend, Doctor Dolores Witchell, captivates both the 18-year-olds with the use of a suggestibility drug which she administers in coconut milk. With its help in Chapter 3, Vanessa convinces her stepson that the route to her heart is through him wearing the little boy blouses and sissy buttonpants that she dresses him in.
Chapter 4 James and Tristan meet Miss Prindle
"Turn round. And again, hands at your side, show me your cock." Alma stood tall, her hands on her ample hips. "Hmm. You are nearly ready to be dressed for this morning's class with Miss Bernice. You just have time for your drink. Sit here on my knee."
Tristan Blake was horrified. Ashamed but somehow weak and robbed of the resistance he should be showing. He was naked in the cool bedroom air of a woman in her forties, whom he had only met yesterday, and he was letting her get him dressed. Letting her boss him about. And now she was telling him to sit on her lap. She held him by the wrists and manoeuvred him into position above her as she sat in her upright armchair at the dressing table. He would most certainly find his bare flesh touching those magnificent chocolate breasts of hers, swelling from the lavish spray of ruffles at the front of her aqua silk blouse.
"Don't you dare put your hands in front of your cock. I want it stiff and showing your feelings." She turned his bare ass towards her lap and sank it into the petticoated spread of her silky, dark blue pleated skirt. He flinched with more shame as her blouse sleeves closed around him and slid him into the exact position she wanted. He sat sideways on, with both his legs down one side of her pleats, and her dark face only six inches from his.
Alma Firenze was a classic Afro-Carribean beauty, a former wrestler like her friends Vanessa and Bernice, who between them were shaping big changes in the lives of the two young men they had in their hands. Tall and shapely, with her black hair permed back behind her head, she wore small white hoops that dangled on either side of her jaw. The whites of her eyes and her pure teeth barely visible between her glossed red lips had Tristan subdued. it was humiliating to lie back on her arm like this, but he couldn't disobey her, no matter what she told him to do. She smacked the insides of his thighs apart, so that one foot lay over the arm of the chair while his other leg rested between the points of her knees. If only his cock wasn't standing up like this. Then his throat whimpered as her fingers closed round it and shaped it in clasping strokes from base to knob. Another smack made his legs spread wide again.
"I want this thing standing up stiffly for me, do you understand?"
Tristan wilted as he tried to avoid her eyes.
"I said, do you understand?"
"Yes, Miss Alma!" "Yes, Miss Alma."
"Weak little boys like you should show full respect towards women. Starting now, while you have your special morning drinkies."
"What? Listen - Miss Alma - I'm 18 yrs old and I shouldn't be doing as I'm told."
Her jaw tightened and he felt the blast of her breath as she snorted at his words. He regretted them at once as she clenched him into her bosom to trap his arms, then rained a volley of short smacks onto the opened flesh of both his thighs.
"Owww - Aaaahhhh! - Stoppit! - Oouuchhh!"
"You're a weakling and a pansy pouffe, my boy," she said through gritted teeth as she forced his legs down with her free arm and opened them out again and looked down at him. She took up a feeding bottle - a large one - with a baby teat at the top, and held his face with one cheek pressed against the fleshy bulb of her breast. "You'll do as I say, and you'll love it. Open your mouth!"
Tristan barely parted his lips, but the teat forced its way in and a bottle of coconut milk stood above him, its cold contents guggling down his throat. It was shameful to be treated like this, he knew, but he also liked it. For some reason, he wanted her to boss him and keep him under her control. His cock was definitely liking being under her blouse, and having her bright brown eyes gazing down into his. As he looked up at her, he felt himself wanting more and more to do what she told him to, even though there was no smile, no friendliness, just a face of command.
"You will fall in love with my breasts inside my satin blouse." She kept him under a steady stare. "In fact ALL ladies' breasts. They are so fascinating for boys like you. But you will wait for permission before you put your hands on them." She pulled the bottle teat from his mouth and put the bottle on the dressing table. She needed only one hand to undo the front of her blouse, and to Tristan's amazement, both her breasts poured from the silk to hang in front of him, their nipples swollen into points in aureoles the same brown as her skin.
"Bring your hand out," she said, and he wriggled to untrap his right arm from her waist. "You may hold my breasts. You love them, don't you?"
He swallowed and touched them with both hands, afraid to trespass too rudely.
"I said hold them, not tickle them." She made one hand open out and grip the lower half of her globe, then spread the other hand too. He was holding Alma by the breasts and his cock ached with unknown pleasure as she presented the bottle to him again and upended it. " You want to press your face in between them don't you, my boy? You're going to find it hard not to ask ladies if they can fold your face into their bosom - because you're going to want to be their baby and for them to feed you as your mother."
Her words shocked his ears as he guggled on his coconut milk, but even more frightening was the urge that weighed in his mind - the desire to kiss and suck those stiffened tits he was gazing at. They were the most lovely tits he had ever seen. He had never been this near and they felt so smooth and soft and yet they were firm. His fingers slid upward, and he found both nipples at the same time, making him suck harder and harder on his feeding bottle.
The eager touch of his fingers brought a deep breath of satisfaction to his mistress. Her pearly teeth almost smiled at him as she hugged him between support arm and bottle arm. "Tristan is a good boy," she said, her voice level but encouraging. "He will want to be like a little boy again to please Alma. He wants to please the ladies, like Vanessa, because she is so pretty and wants him to be a little boy again. A pretty little boy like James." Her arms alternated between hugging and slackening, and he swelled with feelings, his cock so happy each time she hugged him. "Does Tristan want to be a little boy for Vanessa?"
He gurgled a hum from his teat and nodded, his eyes lifting from her tits to her eyes for a moment. He had never felt so bare in his body and yet so warm and safe. Alma would tell him what to do. His sucking came to an end as the last drops drained from the teat, and she took it from his mouth.
"Bernice is so clever," she said, putting down the empty bottle, "so nice, and she wants Tristan to wear a little boysie blouse for her. He's going to wear his blouse with little boy short pants for Bernice." Now that she had a hand free, she held his erection, and it was rock hard. "You like little boy shorts, with satin lining around your private boysie parts. But you don't want ladies to undo your pants - they may touch your special places, and they are private aren't they?"
Tristan gulped. "Yes," he said, "I want to wear my little pants." And he added: "Then the ladies won't touch my special places." He wasn't aware of the blushing that reddened his face.
"Your little pants and your little sissy blouse. Tristan is going to feel so ashamed. So shy. It will be so embarrassing when the ladies see my little boy. But he wants to feel shameful and sissy - and so-o-o pretty." Her fingers frolled softly up and down around the head of his cock, and her captive felt blissfully delicious. Right now he would do anything in the world that Alma wanted. She let go of his penis and rearranged him slightly so that he was more face on to her bust. She lifted one of her breasts from beneath and held the tit to his mouth. "Open - for sissy suckies."
He didn't just open his mouth - he spread it over her aureole and sucked to save his life. Her fingers played on his cheek, up into his hair, over the tip of his ear and touching, tickling his sucking lips. She lifted his face, turned her other breast into him and gave him her other tit, then her hand found his cock again, grasping it in smooth upward pulls that had him gasping onto her aureole.
"Alma's little boy doesn't want any ladies to see his special places. I'd better dress him in my favourite toddler frillies. Tristan won't like it, but we have to cover these sissy places, they're so sensitive and pretty." Her fingertips rippled underneath his helmet, bringing whimpers and loud sucks from the lips devouring her tit. "They'll have to be dressed with ribbons and little frills of lace because they're so sissy, and hidden away inside his pretty boysie shorts and blouse. Shall we do that, my boy?" she got no more answer than a wide-eyed gaze and liquid sucking and slobbering on her breast. She released his cock and lifted his chin clear of her tit.
"Pleaathe dweth me in my fwillieth, Mith Alma," he lisped, and his face crumpled into whimpers of shame.
When Alma led her teenaged sissy into Miss Bernice's schoolroom, he was crying openly at the shamefulness of his appearance, trying desperately to hide himself behind her in case Miss Bernice or his friend Jamie saw how disgustingly sexless he had become in the space of half a day.
The boy's immediate impression was of walls of mirrors, right up beyond the crystal chandelier, while the room was lined with ladies wear - blouses mostly, but also flouncy petticoats and even rows of little shorts looking shiny and lacy. His heart sank as Miss Bernice approached him with a smile on her immaculate, smooth face, framed in raspberry blond hair which she wore pulled softly back and tied up for efficiency. Her bust stood out in the cleavage of a red satin blouse, with all its edges at her breasts and wrists prettied with ruffles. Her hips sizzled as they approached in a tight sheath of dove grey to below her knees, and her arms opened, aiming for the cringing Tristan.
"Alma, what a darling you have turned him into. What a sissy! Just look how silky and sexless he is," and her arms would not be resisted as they clasped his little white blouse in an embrace of red satin.
Her perfume was musky, as if she was a lady of the night intent on trapping any and every male, and it centred on her cleavage. Tristan swooned with pleasure as she squeezed him deeper and deeper into the frothy lace waterfall of her blouse. When he resurfaced, her bright red lips dabbed five or six soft kisses on his face. "Ohhh, let me see your blouse, you dear boy. Mmmm, such a sweet little rounded collar with pretty lace trimming, and more lace down here, round these darling pearl buttons. And little girly puffed sleeves. Oh Tristan, you are trying to be a little girl, aren't you?"
Tristan would have run away, even leaving Alma, if he could have escaped the grip Bernice had on his wrists. "And your shorts, darling," she went on, holding his hands out wide to display them. "I love to see little boys in cream satin shorts, Alma, don't you?" Her friend assured her she did but with less effusion than Bernice was showing.
"I just love the way your little pants button onto your blouse up here, darling boy. That is so sissy." The buttons were white from his blouse, each of them an inch wide and straining on his buttonholes, keeping his pants pulled tightly up between his legs.
"And darling, oh look Alma, he's showing me his sissy button here, right in the middle, on top of his little dickie. It must be so excited and stiff in his little pants." She caught his face with her hands, cupping his jaw on both sides, and kissed him full on the lips. Her grip prevented him from pulling away, especially since Alma stood behind him, and he endured a long, warm kiss which captivated him more and more the longer it lasted. She released him, her lips puckering as if with desire to plant another on his mouth. "I am so pleased with you, darling, for looking so sissy."
A whimper from behind her alarmed Tristan. Oh no! Surely James wasn't here to see him like this.
But he was. As Bernice turned to usher him into her schoolroom, he saw his friend, sitting in Vanessa's lap, a picture of silky blouses, stockinged legs and silky skirts. The poor boy was dressed in one of his stepmothers ultra feminine blouses in salmon pink satin, its ruffled collar surrounding his face as she held him in her arms and kissed him repeatedly. In place of shorts, his friend was in a pair of her full-cut panties in some kind of ivory silk or satin, almost silver in colour and with two or three inches of lace round each leg.
As Tristan was brought closer, his hands held by both women, Vanessa opened her stepson out, revealing the sorry state of his fiercely stiffened penis in her panties, erected in front of his blouse and tied round with ribbon in hot pink satin. He had a bow of the same ribbon tied on top of his hair, and as the two boys saw the state of each other, their throats filled, as well as their eyes, and they burst into sobs of shame and despair.
Their noise would have been upsetting enough, since it indicated the depth of their misery at how low they had fallen, but Alma and Vanessa introduced a finger into their mouths, giving their toddler sissies something to suck on. It worked well, and Bernice took the opportunity to tell her friends what she wanted to do with the boys in her schoolroom.
"Both of them are equally effeminate, I can see, and I am going to see what we can do to make them fall in love with ladies' things, with your help, girls. Because I've got a feeling that if they love our pretty clothes, they will fall in love with being sweet and delicate little love-bunnies for us. Isn't that what you want for little Jamie, Vanessa?"
"Oh I would love my darling little boy to be a pretty sissy sweetheart for me," came the reply as his stepmother folded him in an arm, gazed into his very worried eyes and kissed him delicately on the end of his nose as he sucked and sucked on her finger.
"And Alma, do you not want this pretty little sweetie to fall in love with ladies' dresses and petticoats and skirts and lingerie."
"I do, and what's more, I'll be with you in making sure he does." Her eyes, like Vanessa's, met her sissy boy's gaze at close quarters, only her look was one of firmness and domination rather than blissful emotion. Tristan, for his part, held onto her finger for dear life between his tongue and palate for fear he might lose the chance of obeying her every wish.
Bernice had two high chairs ready for the boys, set facing each other with not much room between the chairs and the surrounding mirrors. They shone in pink satin from top to bottom, with upholstered seats, backs and arms, while similar satin-covered cushions ran down each front leg. Vanessa and Alma led their sissy boys towards them, grizzling with shame and dismay now that they didn't have their favourite lady's finger to suck on, turned them round, and helped them to step up and slide their bottoms into the middle of the satin seat.
"Sissy boys who want to please the ladies must be fastened firmly in place in their pretty chairs," declared their governess, starting with James and wrapping wide ribbons of pink satin over each of his forearms, doing them into lavish bows on the outside of each chair arm.
"Good boy," cooed Vanessa, sitting on the stool attachment beside his chair and clasping the fingers of one of his hands. "I know you want to please me, my dearest darling. And you want to please my friends too. It makes you so excited to be dressed how I want you, so that you are making me and the ladies happy."
James held onto her hand nervously. "Yes, Stepmommy, it's what I want more than anything in the whole world. Are you pleased with me for doing what my governess wants me to?"
"Oh sweetheart, I am so, so delighted," and Vanessa leaned across him to slip a hand round his hair and pull his lips onto a warm kiss. Alma had Tristan in his chair too, with satin ribbons across his bare arms and round his bare legs at his ankles. "You will ask your governess to show you the prettiest women's clothes possible, and you will love them," she said. "Do it now."
Tristan's heart hammered in his little blouse as he turned at once to Bernice, who was arranging tall brackets of metal rails beside his chair.
"Oh please, Miss Bernice, will you show me the most lovely, the most feminine ladies' clothes, because I want to fall in love with them for Mistress Alma. I want to do just what she says, and she wants you to make me love ladies' clothes more and more."
Bernice held her lips pursed through this little speech, completing her frame and then reaching behind his chair to bring into his view a hanger bearing a knee-length gown of white satin, rippling with flounces from the waist and flanked by long puffed sleeves with a deep diamante neckline plunging almost to the belted waist. It hissed in front of him, then to the side as she hung it in front of the frame so that the ruffles of its skirt flooded over his arm.
"I thought you would like to fall in love with one of Mistress Alma's cocktail dresses," she said, slipping one hand into the cuff of a sleeve and displaying the liquid softness of the satin that gathered up into the padded shoulder.
Tristan's mouth lolled open, a run of saliva falling from his helpless lip.
"And I know your mistress would like you to worship her rayon slip in powder blue - with lace here, and here, and down here -" and she hung the exquisite lingerie beside the dress - "as well as her brassiere with matching lace - and her lovely ladies' panties."
The moan that escaped his lips was more of a squeak - a long one which he didn't even know he was making - for he was already in love with Alma's delicates, and couldn't wait to show his Mistress how deep and how passionate his love was.
Vanessa, in the meantime, helped Bernice arrange some of her things around her wilting stepson. A large blouse in magenta purple silk hung beside him, its waterfall jabot tumbling from the level of his hair to below his knees, while its billowing sleeves hung sweetly on either side. Against his other arm Bernice hung a sunray pleated skirt of Vanessa's, so that the integrated petticoat frills swelled against his cheek, his blouse and his knee, filling him with blushing intimacy with his stepmother's precious clothes. In addition, as many as eight pairs of Vanessa's satin panties were arranged at different heights, behind him and around him, and Dolores helped Alma do the same around Tristan with her full-cut panties, so that the boys looked at each other in their high chairs with screens of the loveliest of feminine apparel closing them in on all sides. The close attention of four ladies had the boys close to crying, when Bernice appeared between them with yet another lady, a stranger, whom she wanted to introduce to Vanessa and Alma.
"I've contacted a good friend of mine," she said, smiling at the tall, strongly built woman at her side in her 60s. The ladies stood in what space there was between the boys' knees and the clothes and lingerie that encompassed them. She wore her dyed black hair fastened in a vintage snood, drawn back from an impeccably made-up face that immediately reminded the women of Agnes Moorhead. "This is Vivienne Prindle, who will assist me as a second teacher for your boys. She is experienced at teaching very young sissies, and is going to make sure James and Tristan become more attractive to their Mistresses."
If this woman was a trusted friend of Bernice's, who she recommended as the sort of woman to instil sexual weakness in the boys, both Vanessa and Alma knew she must be a good woman to know. "Vivienne," said Vanessa, turning from her stepson to give her guest an embrace, "you're most welcome to stay at Pettipant House. I'm very concerned to dress James and his sissy friend in ways that will keep them deeply attached to us since - that will be to our advantage. Have you any preferences in how you dress sissy boys?"
The new teacher's lips curled into a astute smile of carmine: "I want each of them to be dressed in little boysie two-piece suits," she said. Her voice was strong but velvety smooth like a man's. "A pretty coatee with either a matching skirt or a pair of sweet sissy pants buttoned onto their blouses. They are going to have to act like little toddler sissies from now on."
Her words acted like an audio switch to turn the boys on, because the two of them set up a wail of crying at the same time, with James turning an appealing look on his stepmother, and Tristan looking at Alma with horror in his eyes. But Vanessa and Alma, and the other two women who faced them, nodded their agreement with the governess, showing the boys a unanimous front. Their misery was so loud it evidently came from the bottom of their hearts, and Bernice produced two small bottles with large feeding teats and passed them to Vanessa and Alma. The women inserted them into crying lips and brought a stop to their noise with their next dose of coconut milk so that they had to listen to Miss Prindle in silence as she sat between them inside their screens of blouses, dresses and lingerie.
"I'd like to inspect the boys' genitals as they drink," she said, "to assess their reaction to being watched by us all while we discuss their dressing." Her fingers skilfully slipped Vanessa's panties down from James's waist and under his ass so that his cock and scrotum stood exposed for everyone. Then she undid the button closure under Tristan's crotch and used both hands to stop him clenching his thighs. She brought his cock out, standing ignominiously between his legs. Bernice helped by adjusting the ribbons at the boys' thighs so that their legs opened wider to leave their penises in full view.
"Miss Prindle is called on by several dominant ladies she knows, to correct the sexuality of their husbands or stepsons. She's quite used to bringing the best humiliation out in the most difficult of sissies."
Doctor Dolores reached across and held James's cock in her fingers. "That's true, Vanessa," she said. "I know two women whose nephew and stepson were very successfully sissified by her. She'll bring about some very nice changes in your boys." She smiled as she caught James's eye and felt the growth in his penis. Both boys tried to wriggle their arms free of their ribbon fastenings and gurgled in fright into their coconut milk, but Vanessa and Alma held them more securely to ensure they kept drinking and listening.
"That's right," said Miss Prindle, "the best results are always achieved when the boys' penises are kept out in the open, especially when ladies are discussing how they will be softened and feminized in their sexuality."
While Doctor Dolores worked on James's cock, Miss Prindle herself took Tristan's in one hand, lifting his chin towards her with the fingers of the other. "I appreciate any chance that arises to sissify youths," she said, "and how lovely it is to see two boys being sissified together." Her gleaming lips curled again into a mischievous smile. "What I would love is to bring my own sissy to join them, if I may."
Vanessa and Alma almost cried out. "You have a sissy of your own?" "Please bring him to join us, we'd love to see him."
"Thank you, Vanessa. I'd be happy to do that. He's just 20 - the ex-first-husband of my daughter. She passed him on to me and now I've trained him as my bedroom pet sissyboy."
Both boys moaned with horror, but their horror was mingled with perverse pulses of pleasure under the masturbation of their defenceless cocks.
"I would be very interested," said Vanessa, keeping James's bottle tipped high, "if you could arrange for any ladies you know to bring their sissies to Pettipant House. Then we can all enjoy their helplessness."
"Oh how delightful, my dear. I know some ladies who would be thrilled to show off the condition of their sissies." She paused to adjust her fingers on Tristan's cock, feeling how stiffened it had become at what she was threatening. "I'll make arrangements for some ladies to bring their unsexed sissies, and we can have an amusing time watching all the sissies surrender their sex to us."
Both boys spluttered into their teats and wriggled hopelessly, ribboned to their chairs. Alma fussed and arranged her dress and lingerie around Tristan as if to show him how inescapably he would be doing as he was told, while Vanessa clasped her hanging blouse against her stepson's cheek as he drank, and pecked him on the cheek as his penis was masturbated. Maybe as a result of their panic of shame, both boys drained their coconut milk together. The women around them giggled and put the bottles to one side so that they could fuss and fondle their captives more intimately as their cocks stiffened shamefully. Bernice had a question that must have been on the lips of all the women.
"Viviene, what kind of fashions have you brought with you, for dressing James and Tristan, so that they are secured in the affections of their Mistresses?"
The teacher smiled with coy satisfaction. "They will wear more infantile costumes, with side buttoning romper pants, and puff sleeved baby blouses that button down the back."
James wailed with despair, and Tristan cried out with humiliation, causing Vanessa and Alma to stand up beside their sissy high chairs. "Oh darling, won't you be lovely for me!" cooed Vanessa, clasping his face between her hands and kissing him deeply, while Alma opened the front of her blouse and turned her sissy boy towards her breasts. His cries disappeared even before she had pulled him into her cleavage, but she made sure he was deeply surrounded and squeezed between the dark globes as she held him under her control. Neither boy could be mistaken, thanks to the lovely reaction of Vanessa and Alma. What Miss Prindle planned was exactly what their mistresses wanted: to have their boys wearing little sissyboy costumes in the sweetest of styles - very girlish, and very young.
Their cocks were discovering how desirable their sissy-toddler frillies would be too. Little sissy-boy clothes seemed a wonderful way to draw the ladies towards them. It was what ladies wanted, it seemed: to make their loving boys helpless and weak, and it was lovely to do what Vanessa and Alma wanted. So blissful, so sweet and rosy, and as the women fondled their genitals between their screens of silk and satin, the boys cried out and surrendered their cream in gushing spurts for the ladies, into the controlling fingers of Miss Prindle and Doctor Dolores.
Next time, in the fifth and final chapter, James and Tristan are not the only sissies to amuse the ladies in Pettipant House.