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Author Topic: A Sissy is Born  (Read 41460 times)

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Princess PowderPuff

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Re: A Sissy is Born
« Reply #35 on: September 22, 2023, 09:24:31 PM »
8. ROMPERED


His mother approached. She couldn’t help but smile at the pretty face that looked back at her even if it was a grumpy one. "Well whilst you’ve been relaxing having your hair done and your makeover and enjoying a manicure I've been busy looking at socks and shoes for you and choosing you some dresses I've also found you the most wonderful rompers." She couldn’t wait to get that beanie off his head and let him see the outcome of his hair appointment, but that could wait until she had him in a dress. She wondered just what he would make of his beautiful ringlets or his dress for that matter. There was only one way to find out. "Come on lets go shopping!" she said brimming with enthusiasm he couldn't match. "You could at least make an effort to enjoy yourself David it's going to be a long 10 days for you otherwise. Come along and do keep up."

At that he stopped and stamped his foot so hard on the floor he hurt himself. She turned to see his trying to pull his pacifier from his mouth fortunately it ended in failure so he turned his attention to removing his rubber pants. "Now you listen to me young man you stop that immediately or you're in for a spanking!" David flipped her the finger and made to run away though where to he couldn’t say, just away from her clutches. She caught him by the arm and spun him around which was when the paddle made contact with the back of his thigh with an almighty slap and nine more just like it. Tears flowed freely down his cheeks. "Another outburst from you like that and you'll be accompanying me around town just as you are do you understand?... I asked do you understand!?" she took him firmly by the ear and pulled him along. "I really don't understand you David. You begged to be allowed to stay in the crèche and now you behave like this. You can be so ungrateful.

David was sulking as he followed his mother down the aisle she stopped by the tights section and began tossing pair after pair into the trolley. "You really should get involved with choosing your tights David you will be the one wearing them if you're just going to leave up to me you might not get any of the ones you like. I've got you a broad selection of pointelle ones with pretty knitted patterns in a variety of colours and half a dozen flesh tone dance tights for a more natural look for regular day wear and I'll get you some nice lacy ones for dress up days and parties. For when you want to look extra special or just look nice for the boy in your life. I found some really nice socks that will go perfectly with your dresses."

They made it to the foot ware section where David's mother had him pull on a pair of 80 denier suntan tights she let him struggle with them on his own and just tossed hints for him to find the easiest way of putting them on. "Your legs look good in those," his mother told him "maybe we should have you wear them all the time? Now we must find you just the right socks. Then you'll be ready to try some shoes on." He baulked at wearing the socks chosen for him they looked like a pair of goddam tribbles and judging from the other tribbles in the trolley they came in a variety of colours and were breeding…fast. She tossed him a pair. "Get those on your feet… the other foot. The writing goes on your outer ankle. Don't those just look super? They're just so infantile they're wonderful." He was almost in tears again but his shoes were the tipping point and the flood gates reopened. "Try these shoes" and she thrust a pair of pearlescent pink leather ones at him. "Aren’t they just the cutest things they have a little bunny face on them?"

To add insult to injury he was passed the very thing he turned down in the first place… a pair of short-alls, sans pompom tail and ruffles with a fleece lined towelling panty to make him look more respectable whilst his mother hunted down the perfect romper. Much to David's chagrin he and his mother received many compliments from other mothers seeking something similar for their son's, and David was compelled to strike various feminine poses for them to show off his outfit.

The romper as his mother called it looked like an over sized multi coloured dried chrysalis but he sure as hell didn't feel like a butterfly right now but by the time he'd wriggled into the thing he reckoned he would look like some grotesque caricature of a caterpillar. The bodice looked to small whereas the panty section looked like a shrivelled ball of ruffles. It could have easily been modelled on a bunch of hydrangeas. He doubted it would fit, what joy that would be to see the disappointment on his mothers face as her scheme showed signs of unravelling. No way was he going to be made to wear that.

"Let's see just how badly you want to wear is delicious romper with all these macho frills." She taunted. She made him jump up and down and clap his hands with joy at the prospect of wearing such a sissifying garment. David did not feel happy at being complicit in his own emasculation but true to his mothers wishes he demonstrated his joyful enthusiasm at being allowed to wear such a hideous garment. He jumped up and down and clapped in an eye catching display of true enthusiasm. Tears welled in his eyes. "You must be so looking forward to wearing that? Now let me see you wriggle into your darling little romper."

He smiled to himself unseen behind the big pink plastic mouth shield of his pacifier. The moment of truth was here. He would show her she couldn't get away with this; this was going to give him so much satisfaction. He all but snatched the romper from his mother’s hands eager to make his point.

He was having trouble moving and bending over in all his bulk so she was on her knees ready to guide the garment over his feet whilst he balanced himself with his hands on her shoulders and raised each foot in turn to facilitate his denigration. Once his feet were through the leg openings the rest was up to him. It was going to be his responsibility to pull the garment up and dress himself as far as he could manage. He pulled his rubber pants on; he'd been made to put his tights on, and socks and shoes and she saw it as perfectly reasonable that he should continue to debase himself by putting on his romper as a justified penance for his earlier actions. He should have the satisfaction of turning himself into a sissy how she would enjoy watching his bravado slip away to be replaced by something altogether different, something weak and emasculated something more docile and malleable, in favour of something more befitting an effeminate sissy.

He pulled, and it climbed up his legs. Higher and higher it went until its crotch sat nestled tight up between his legs the ruffles taught across his pelvis and fluffed out in all their majesty and the bodice snug around his chest, his arms in its sleeves. It fit like a glove. He was mortified. An absolute cavalcade of frills poured down his torso from his sternum to his crotch and all the way down his back from his shoulder blades, above the frills the front was beautifully smocked across his upper chest. He burst into wracking sobs and his mother quickly sealed his fate by buttoning him in from behind, the Edwardian collar high and tight round his neck with a wide frill pressed up under his chin. Heavy lace Juliet sleeves covered his arms topped at his shoulder by over sized raised and gather puffy confections with ruffled lace caps at the shoulders and gathered to fit snugly around his bicep half way from his elbow. The sleeves extended into grown on gloves in which his hands were already incarcerated all that remained was for his mother to close the mass of stiff fiddly buttons down the length of his forearms and close the buckled strap around each wrist and button him closed down his back. She made him submit to a pair of clumsy padded satin over mittens, embroidered across the back with the "Sissy" logo which she insisted he push his hands into whilst she held them and closed them around his wrist with drawstring tie she fastened into a knotted bow to confirm his confinement. He was instantly transformed into a helpless toddler. He was crushed. He could neither remove his mittens himself nor manipulate anything he had the dexterous ability of a two year old and now he was buttoned up the back his confinement was assured. There was no going back for him now, only forwards and to whatever that might bring. She was amazed at the effect the close fitting lace sleeves had on his arms. They had achieved exactly same results as the tights had done for his legs. They had quite literally stripped away any signs of his developing adolescent musculature and left his arms looking slender and feminine and his hands looked decidedly small and dainty in the attached lace gloves. A completely unexpected bonus, she couldn't have been more thrilled with the result.


This work is copywrite © Princess PowderPuff 2023.


mikeh1993

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Re: A Sissy is Born
« Reply #36 on: September 23, 2023, 06:30:25 AM »
I just love all the little details you put into this story. 


Princess PowderPuff

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Re: A Sissy is Born
« Reply #37 on: September 26, 2023, 10:05:12 AM »
9. A DRESS FOR DAVID

"Time to get you into some petticoats David" she said pulling one of the frothy confections from the rack and offering it to him to put on. "I bet you've been looking forward to this moment all morning haven’t you sweetie?" He so wanted to refuse but the back of his legs still stung from his second encounter with his wooden paddle he dare not refuse instead he bounce up and down in glee to demonstrate his readiness to embark on the next stage of his emasculating regression to a teenage toddler.
 
At first he tried stepping into the petticoat dress but the sleeveless top was too small to pull up over his nappies. "You'll have to pull it on over your head" instructed his mother. He struggled with it valiantly. He grabbed a handful of skirt which seemed to have a mind of its own, every time he made to grasp it, it seemed to grow larger and less manageable and was being more successful in its uncooperative stance at not being worn than he had managed in avoiding his nappies and romper. His mittened hands were not working in his favour. His mother came to his rescue, delighted by his display of helplessness. "Arms up" his mother demanded. He strained to look round at himself, but at that moment a petticoat fluttered down over his head and the sight of everything below his chest vanished from view including a circle of surrounding floor space as a cloud of tulle and chiffon with pink satin ribbon bound edges floated around him. He groaned into his pacifier in protest. It took her a matter of seconds to have him buttoned up and imprisoned. "And because you liked that one so much here's another one for you." Dutifully he raised his arms to receive it. His horizon lifted and a little more floor space disappeared from view. His shoulders slumped in defeat and his arms hung loose by his sides. He received a swat round the back of his head. "Don't crush them! Keep your elbows bent get those wrists up. Last one lift your arms!"

As the layers of his petticoats increased, the horizon rose ever higher, blotting out all that lay below in ever increasing diameters. The only good thing he had to say about them was he no longer had to look at those hideous socks that graced his feet. He would have to guess what lay before him to trip over, invisible to his gaze beneath his frothy  petticoats, leaving David to struggle with a dozen layers of very full uncooperative skirts that just bounced back every time he tried pushing them down so he could see where he was walking. "Don’t do that David it's not very ladylike" admonished his mother.

He bent forward out of morbid curiosity to try and get a better view he hadn't realised just how huge they were as they swung forward and hung down in front of him in all their glory almost overbalancing him in the process. Each petticoat dress comprised of four tiered and gathered skirts and each must have had at least a full circle or more of material in them, three petticoats, twelve layers of skirts, no wonder they were so full and heavy and as he had just learned quite wilful and difficult to control as they flopped away from him again and noisy, so noisy, they rustled every time they made the slightest of movements or responded to his own. He could hear their sibilant tones conspiring against him with the rustle of his frilly romper and the clack clack clack of his rubber leak proof panties as he moved. He hated them with a passion! Almost as much as his romper.
~o0o~

They were relentless like the Borg. "Resistance is futile, you will be assimilated" there seemed to be no respite from their continuous assaults on his masculinity as they systematically tore great pieces out of him and replaced it with something very alien as he was systematically reduced in appearance, ability and status to that of a toddler.

David had hated the whole process of choosing his dress, just as he had hated everything else that lead him to this juncture. His masculinity was under constant assault and he was losing steadily.

"Isn't this the most beautiful dress I bet you can't wait to try it on?" David found himself jumping up and down yet again exercising enough due diligence to satisfy his mother of his desires to be ridiculed further just as he had earlier when he had shown how thrilled he was at being put into so many stupid petticoats. Anything to avoid the encouragement provided by her wooden paddle.

There was nothing remotely masculine about his petticoats, just as there was nothing masculine about his frilly pantied romper and his socks were less masculine that the other two put together. "You are very lucky being an older sissy you can get involved in choosing the best ways of feminising yourself and help in choosing your own accessories to achieve it."

David did not feel lucky at being complicit in his own emasculation and displaying his enthusiasm by jumping up and down and clapping his mittened hands together adding his seal of approval to his next round of humiliation he was to enjoy.

His mother had laid out 6 dresses that she thought would suit him. She was only offering David the section of dresses because she understood dresses better than him. But the final decision was his. She didn't want to choose one for him which was why she insisted he do it himself just as she had allowed him to choose the rest of his outfit.

She didn’t want him to feel forced into wearing anything he didn’t want or didn’t like. She just wanted him to be happy with the choice and the reason she had him curtsying and whirling was so he could get an idea how different fabric and styles moved with the wearer and he would feel more feminine in one dress as opposed to another. As if he cared. All he had to do was get to the car park. Who cared if he looked more feminine in one dress or another, so long as it got him home without being recognised?
All he had to do was try one on, parade himself in front of the large mirror, curtsy to himself, do a twirl, then swish one way then the other and his petticoats dutifully followed him and curtsy to himself again turn and curtsy to his mother then to each of the assistants helping them, and repeat the process for the next dress and so on. This was overkill and the sooner it ended the better but the only way of ending it was to  go through all this damned swishing and swaying and curtseying and suffering the 'oohs' and 'aahs' of his mother and the assistants as he humiliated himself in yet another dress.

It all sounded very easy... except.

He was hampered by three wilful petticoats a fleece romper with grown on gloved hands and padded mittens and attached very lavishly frilled panty, worn over a pair of towelling short-alls, 2pair of rubber panties that were as noisy as hell and 3 sets of Thick & Thirsty nappies and soakers, not to mention thick tights, silly socks and stupid shoes and a very uncomfortable butt plug stuffed up his, well never you mind. He could barely manage a waddle, let alone a walk. The look of concentration on his face was intense. "Smile" his mother had admonished "you're supposed to be having fun."

As if! Not that anyone would see because of the mouth shield of his pacifier. His mother said people would know by the bounce in his step when he smiled, if he frowned he would trudge. What did he care he was in no mood to be trying on dresses he didn’t give a toss about anyway. So he bounced, and so did all his damned petticoats.  AARRGGGHH! They were at least having fun even if he wasn't.
 
He would have told his mother to go forth and procreate had it not been for the huge pneumatic phallic shaft firmly inflated in his mouth that had taken all semblance of speech from him. So he settled for "gahunph" instead cramming it with as much venom as he could muster and mentally projecting it at her. But it was just his luck that his psycowatsit skills were letting him down today and she remained unharmed.

"You walk like a dock worker you could at least try to be more feminine and graceful, well if you can't get one foot neatly in front of the other then try do something with your arms. Tuck in your elbows for goodness sake lift your wrist, higher, higher that's better, now keep them above your waist line. Relax, flap your hands, you're a sissy you're supposed to be limp wristed." She was exasperated by his intransigence. "Do I really need to paddle them in place?" There was a vast and immediate improvement in his carriage. "Now commit that to memory I don’t want to see your arms doing anything different. Now repeat that walk through again will you please. Properly this time!" He let out a sigh; thank goodness he only had four more dresses to go. Until finally he settled on this one...

~o0o~

If he thought his socks were bad then his dress was worse. So much worse. He might well have chosen it but she had already decided which dress he was going to wear and had gently steered him towards it. It was actually his last choice and least favourite, most disliked might have been a better description, of the six. The fact was he loathed it so much he would have happily used it to kindle the fire to burn the other five.

From his unique vantage point trapped within its ridiculously cutesy folds he could categorically state it had no redeeming qualities at all. Had he realised what he was getting himself into at the outset he would have gone shopping in the complimentary disposable nappy they had offered him. He was a walking advert for 'Sissy of the Year' he couldn't have proclaimed his status better if he been neon illuminated.

This work is copywrite © Princess PowderPuff 2023.

mikeh1993

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Re: A Sissy is Born
« Reply #38 on: September 26, 2023, 10:02:39 PM »
I’m loving the details given each chapter.  Also I love the subtle Star Trek references in the past couple chapters

Princess PowderPuff

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Re: A Sissy is Born
« Reply #39 on: September 30, 2023, 12:26:53 AM »
mikeh1993, this one is for you. Thank you for all your comments.

9B. A DRESS FOR DAVID  continued.

The pink heavy cotton sateen bodice and skirt was banded by a pink, yellow and blue diagonal candy stripe around the scalloped hem and was decoratively finished with a lavishly fur trimmed hem. Above the candy stripe was a frieze of at least a dozen appliqué teddy bears marching around his skirt each clutching in its paw a string of five appliqué balloons in pastel colours which floated gently up the skirt. Each one carried a single letter which spelt the word 'SISSY' across each clutch of balloons. The skirt was further adorned by a sheer off white chiffon overskirt with a diamond chain link pattern picked out in fine gold thread and decorated with diamante floral clusters and seed pearl accents scattered about its surface.

The bodice of the dress was closed with a concealed side zip and had a sheared back panel to ensure it achieved a figure hugging shape which was further enhanced by corset back lacing which was drawn tightly together. The slight V shaped front of the small basque waistline and plain back waist was highlighted with a baby pink piped seam with a gathered gold lace ruffle. The neckline was square cut and edged in fur as were the candy stripe oversize puffy sleeves that sat high and tight on his biceps.
 
The half belted sash waist was unusual in that one tie was pink and the other blue and when tied produced a large attractive chocolate box bow with long streamers that reached down to touch the hem of his skirts. The romper he wore beneath the dress served very nicely as a blouse, looking very Laura Ashley with its Edwardian high neck and pie crust frill that came high up under his chin and hugged his neck snugly. The long slender sleeves button closed from his elbow to wrist and terminated in a padded over mitten. His hands further confined a pair of Helpless Hands padded pink leather safety mittens with large fur cuff, for added cuteness, which were buckled at the wrist as a further security measure and to stop him from flapping them off.

His mother thought he looked spectacular and gushed over his appearance. She was far too cheery about this for his liking. "Well what do you think? Don’t you feel as gorgeous as you look?" It was indeed a special dress for a special boy for a special day. Just how lucky was he? He wanted to upchuck. He couldn’t bring himself to think just how absolutely ridiculous he looked in the dumb outfit. He 'umphed' into his pacifier and slumped down onto one of the island seating units. "Get up this minute" yelled his mother. "Don’t you dare crumple your lovely petticoats or put creases in your beautiful dress. If you want to sit, sit on a bench seat and make sure you fluff your petticoats right out so you're not sitting on them. Ankles crossed if you please and knees together or as close as you can get them, hands in your lap. Better still here use this fur muff its perfect for keeping errant hands prettily tucked away and out of mischief and don't let me see you take them out! Now sit properly!  He let out a sigh and plunged his hands unwillingly into the barrel muff which looked to be the size of a pillow and it swallowed his hands all the way up to his elbows. In its plush fur lined interior “Now isn’t that better?” asked his mother. “Appearance is everything. You're not a boy anymore, so you must show everyone just how feminine a sissy you can be.”

~o0o~

"Oooh David" she cooed "you are so lucky your dress has a matching bonnet" she shouted joyously "come, hurry up and try it on and let's see how you look."  That might be all very nice but she wasn’t the one having to wear the dumb thing. "I can't wait to see you in this," she seemed to get more excited as he saw his boyhood slipping away and very soon it would vanish from sight.

He got his first look at the hideous contraption. "Here we go again." He grumbled to no one but himself. A regency style bonnet in pink cotton sateen to match his dress and pink blue and yellow candy stripe box that pulled onto the back of his head with a vast flared brim designed to strip him of the majority of his peripheral vision, with scalloped edge and huge fur trim carried through from his dress. It certainly wasn’t a hat he would have chosen for himself.

"SURPRISE!!" She tugged the beanie from his head and a mop of curls tumbled out. "Don't you look special with your hair in ringlets darling?" and she ran a brush though them just to liven them up. He did make an effort to evade her but she had the advantage of speed and manoeuvrability and advanced on him faster than he could retreat. "There's no need to be bashful darling your bonnet is going to look super cute with your new hairstyle and frame your features with oh so feminine fur around your face and brim it's heavenly so thick and soft I can’t for one minute imagine why you wouldn't want to wear it. It's beautiful. You're going to look so precious.

His resistance was swept aside and he was forced to submit to the hideous contraption being fastened to his head with a tight wide strap under his chin which had a large decorative mock bow to his left side. He shook his head violently to try and dislodge it but it was there to stay all he succeeded in doing was battering  the bonnet with the three large fur pompoms on tassels that were fixed to the back of the hat and dangled down the side. The underside of the brim was in pleated silk with a large cluster of silk flowers off the one side and a second band of fur passes from ear to ear forward of his crown giving his face the appearance of being circled by two very big fluffy halos the last of his boyhood lay in tatters round his feet right next to his vomit inducing socks and she was still going strong he didn’t have any more boyhood left to be feminised  but  she found addition girly touches to add to his already completely sissified self burying him still deeper under additional layers of femininity that he could never hope to escape from unaided.

"You look very nice David, so grown up… Hurry up now it's time for your first baby behaviour class." Something he was so not looking forward to at all.


This work is copywrite © Princess PowderPuff 2023.

mikeh1993

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Re: A Sissy is Born
« Reply #40 on: September 30, 2023, 09:06:12 AM »
Princess PowderPuff, you have a wonderful gift with words.  Reading this last chapter, I could actually visualize it happening.  This story is one of the best I have ever read anywhere.

antonia

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Re: A Sissy is Born
« Reply #41 on: September 30, 2023, 02:26:04 PM »
Now we get to the part that I have been looking forward to more than any other. Great work so far. I feel a story of my own coming on in this direction, so don’t be surprised if you inspire me to write again!

 

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