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Author Topic: The Naughty Sissy  (Read 8442 times)

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Shortyshorts

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The Naughty Sissy
« on: April 10, 2022, 04:21:45 PM »
PART ONE

"Well, this isn't totally unexpected," Laughed Amy Turner from the open doorway of her step son's bedroom.
   A shaggy head turned. Matching auburn eyebrows raised. Brown eyes grew wide. Narrow nostrils flared. A look of terror on the smooth face.
   Standing in the corner of his bedroom, Max Turner's face couldn't have been any redder and that was only one of his worries.    
   Thin arms ached from having supporting fingers interlaced behind a shaggy head causing a tremor throughout a diminutive body. Hairless legs, covered in goosebumps from being unusually bare,  knees knocking at the strain it was for an active boy to remain stationary for so long.
   A cold draft, he now realised had come from the front door opening, had managed to aim itself up under the St. Charlotte's summer uniform, raised higher by having his fingers interlaced behind his head, around the edges of the boy's rounded cheeks, only just covered by the edges of plain white knickers at least two sizes too small for him and which Amy instantly knew the origin off.
   "Sarah's junior school uniform is certainly an interesting choice for you but..."
   "NAUGHTY LITTLE GIRL!"
   The voice, not unlike that of a Victorian School Madam, made Amy jump, but she quickly recovered.
   â€œYes, clearly you've been a very naughty little girl, Max.â€
   Spotting the smart phone, the voice had come from. Amy peered at the display on the phone, noting the decreasing countdown, quickly working out it's purpose.
   "You set this up to watch you being punished, right? Like a teacher would? Clever."
   He didn't reply, his head still turned, so Amy could see why. The pink faceplate of a baby's dummy covering his lips, the small red ring on the front, bouncing as he nervously attempted to push the bulb from his mouth.
    "No, Keep that in." she told him, "Given some of the things you have said to me, recently, it is indeed a fitting punishment, if a little small."
   The click-snap of the phone taking a photograph sounded, Amy quickly pressing enough buttons to ensure the image was sent to her own device which beeped in acceptance.
   "One for the new family album. I think." she told the frightened face, looking back from the corner. "Wonder what Sarah will think of you wearing her old clothes?"
    The jaw beneath the dummy went slack, but even that wasn't enough to free the pacifier from the boy's mouth. Alert eyes scanning about, wondering why his Step-Mum was home, but there was no clock in sight, just the faded wallpaper of the house house, so Max had no idea just much of his initial thirty minute sentence had passed or how much remained of his time in the corner.
   Not for the first time, he'd earlier returned to the big empty house from school his mind racing with unprecedented fury, at being one of the smallest boy in Year9. Slamming every door on his way through the large house the newly enlarged family now shared, coming up with actions he knew went way beyond simply boyish pranks into the realms of actual criminal damage if not common assault, building him up to such a fever pitch he was in danger of trashing his own bedroom.
   He knew he needed a distraction before he did anything stupid, and there seemed only way of doing that. The very way Amy had mentioned Sarah going through at her strict school.
   "Time Out!" it had been called. A way to break the more rumbustious girls at St Charlotte's Junior School, who'd be taken to the kindergarten classroom, put in a corner without outside influence, forced by eagle-eyed teachers, to remain standing still, with their hands on their heads, and a baby's dummy in their mouth, with nothing to do but think about why they were there and suffer the humiliation of being laughed at by the little ones.
   It had been working though even if he didn't realise it yet. His barely teenaged mind no longer ran with rebellion at Amy's new found authority, or the urge to tell her this, using every swear word he knew as an outlet for his other issues.
   "Are those Sarah's panties?" she giggled knowing they were, recognising the pattern around the hem.
   "Bet they feel different to your usual underwear."
   The tall woman's comment making the boy shiver, setting off an alarm on his phone.
   "MORE TIME ADDED!" barked the device, Amy watching as the previously counting down numbers increased.
   "Serves you right." she concluded giving her step son the once over, and liking what she saw.
   The rather plain pink gingham school dress her now grown up daughter had hated with a vengeance, actually suited the slender boy's body. The white collar and cuffs on the short sleeves, highlighting his tan, and despite being made for a ten year old, if a little shorter than it would have been on Sarah at that age. Short enough to show what was underneath.
   The surprisingly strong leg knicker elastic had grown tight as it been drawn over his hairless thighs, a sensation he never got from any of his own clothes. The grip remaining until it slipped into the natural crease between his legs and the trunk of his body cupping his backside, permanently clenching the rounded cheeks, while compressing his front parts, until they were barely noticeable beneath the little bow on the panties waistband. Not that Amy could see that, or his body's reaction to it. She could, however, see panties wasn't the only part of her daughter's underwear, her step son was wearing.
   Stretched across his shoulders, the lines from a halter top vest could be seen, slightly compressing his upper torso, yet leaving his firm young stomach bare. The built in elastic encircling the gingham, pulling in his waist, and making his bottom stand out against the material, giving the unaware boy, visible pantie lines.
   The collar standing up a little, around lean, slightly bowed neck needed adjusting but the fit was good. Sleeves at the top of his arms, making the limbs look longer and somehow barer than they were, just like Max's rather pale legs.
   White slightly woolly pop socks completed the outfit, Max not aware he could turn them down, from where they reached his knees, with a pair of Mary Jane shoes, unbuckling as they squished toes slightly, but as he'd just be standing, Hadn't thought this would matter although it would once they were the only shoes he had left.
   All in all Amy rather liked what she saw but there were improvements which could be made. So, ever the perfectionist, Amy made them.
   "Stay there Sissy!" she told the boy, giving his backside a light pat though the gingham before quickly making an exit to get the things she would need, knowing the phone would warn her if he dared move.
   He didn't.
    Strangely although his head had been a mixture of confusion, anticipation and humiliation, when Amy had first appeared in his room, by the time she returned, he was more relaxed. Having stayed perfectly still the entire time only shivering when his step-mum's hands came around his chest, quickly fastening the three buttons he'd left open at the top of the dress, pulling the material tighter, encasing him in gingham.
   Reaching around his splayed elbows, she did what she could with his hair, just about managing to twist elastic bands into a couple of very small bunches just above his ears, which didn't really make him look like a little girl, but rather less like a boy at the same time.
   The same elastic bands, also had a different use. A series of them combined together to form a length, long enough to encircle the boy's head, with either end threaded through one of a little hole on either side of the dummy's mouth plate, ensuring it stayed there.
   "That will keep your naughty mouth from getting you into more trouble won't it." she told him, pinching each of his cheeks, making them even pinker. "Now let's see about some real, long overdue punishment shall we?"
   Enjoying the heat coming of his slender body, Amy smoothed out the remaining wrinkles in the lightweight summer school dress, able to feel him shiver at the touch, knowing he'd be doing more than that in a moment, once she'd picked up a large wooden hairbrush with no intention of doing anything further to his hair.


Baby Mac

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Re: The Naughty Sissy
« Reply #1 on: April 10, 2022, 06:20:12 PM »
Now that's how you start a sissy classic please keep going


Shortyshorts

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Re: The Naughty Sissy
« Reply #2 on: April 14, 2022, 06:01:57 PM »
Thanks for the support Baby Mac

Part two will be am uncomfortable meal and will follow shortly

Shortyshorts

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Re: The Naughty Sissy
« Reply #3 on: April 16, 2022, 10:48:58 AM »
Part Two:

Shuffling on the dinning room chair, Max Turner couldn't make eye contact with the adults, whilst barely picking at the greenery on the plate in front of him.
   "Has he got ants in his pants?" his Dad had roared with laughter at what was apparently a joke.
   "Panties." Amy whispered, reaching under the table to pat the teenager's bare thigh as if he needed a reminder of what he was wearing beneath his adapted clothes.
   His face flashed red, but he did become still, as his step-mum started to explain.
   "Max wants a bit of tan on his legs and arms." Amy lied through her perfect teeth, "So he's going to wear little shorts all the time, aren't you?"
   He flinched as the fingers inched higher, unable to follow his plan to blurt it all out to his Dad. How he'd dressed up as a way to control his temper, without mentioning the actual dressing up part, obviously. That he was going to blame on Amy. His Dad would have taken his side of his new wife? Wouldn't he? Probably! Maybe! Possibly!
   Then there was Sarah herself, and all those photos Amy had taken of him as a sissy. Those she threatened to send to everyone on his contacts list, if he didn't do what he was told. It just wasn't worth the risk. He hadn't been at his school for long, after all.
   "Yes." he squeaked suddenly as long, brightly painted fingers clasped his leg dangerously close to where his boy parts were being crushed in what an hour earlier, had been his favourite skinny jeans. Now, thanks to Amy's dressmaking scissors they were girlish hot pants, constantly rubbing the tender flesh, through the softness of the panties, he was, indeed, wearing.
   A fresh set of pink panties covered in little flowers, replacing the previous pair he'd inadvertently soiled during his first time over his step-mum's knee.
   The memory of bending himself over Amy's lap. The back of Sarah's old Junior school gingham dress flicked upwards, totally exposing a round bottom barely covered in sheer white panties. kept his face redder than the tomato he was attempting to chew, just not as red as his bottom had become from the hairbrush.
   He'd cried, despite promising himself he wouldn't, initially struggling against the punishment. Amy seemingly easily managing to hold him still, despite his best efforts, while the back of a hard and heavy hairbrush, turned his lilly white, backside, into twin red hot, stinging, throbbing cheeks. Tears had poured down his cute face. Little pug nose running. An even a sheen of sweet covering his diminutive body, making his original panties stick to his body.
   It was the only reason, Amy hadn't pulled the panties down. She hadn't needed too. Able to see the righteous damage she was inflicting as part of her plan to give the previously obstinate boy, a lesson he would not be forgetting in a hurry. If at all.
   She needed a confession though, so the dinner table hadn't been the first occasion Max had been seated on a sore bottom.
    Before that, he was back in the corner, only now the corner wasn't beside the window but in front of it. Hands back on his head, his own phone making sure he stayed there. Adding time, when a group of kids his own age went down the road and he ducked.
   Just how much anyone could have seen, was open to question. The waist high window sill didn't give much away, certainly not the reason why the front of the gingham was poking forwards in a very un-girlish way, but they may have noticed the taller child in the juvenile uniform, and the obvious shaggy haired boy, despite the little bunches held in place with elastic bands.
   Amy, of course, very much liked the view she had. The bright red  bottom contrasting so nicely with the white of the panties she'd caught him in. His hands, kept on top of his head, not the cause of it's exposure, rather the pins keeping the gingham from obstructing what she hoped would become a familiar view, which is why she was doing what she was doing.
   Having fetched bin-bags from the kitchen Amy removed nearly all of the boy's clothes, making what was left, as girlie as she could, yet still decent so he could wear them around his father.
   The snip-snip of the ten inch long scissors removing the legs from all of his trousers, making him shimmy against the backlight of the window, as she provided him with something he hadn't worn in years. Shorts. Lots of shorts. And short shorts at that.
   "Just two inches on the legs I think." she'd teased, using the old fashioned measurements, so he wouldn't realise the actual length until he was allowed to wriggle himself into the tight stonewashed denim, just as his Dad's key turned in the front door.
   "You can always wear your naughty sissy school uniform?" she offered when he'd bulked at the now tiny trousers, "But you might want to change your panties first."
   He had no boxers left, of course, they were all bagged up, sitting on the kerb waiting to be collected, in full view of all the neighbours, so Amy was fairly sure he wouldn't be fetching them, no matter how humiliated he was, by wearing panties in front of his Dad.
   For the last time, Amy gave him some privacy to change. Not a lot, or else she'd have missed the amusing dance he performed, attempting to tug down the gingham over his bare bits, whilst untangling rolled and clearly used panties over his feet.
   Glimpses of boy parts were on offer. Some soft, some not as much as they should have been. Less hair than Amy had expected for his age, but a bottom that was every bit as delightful in the flesh as it had been when covered. A bottom she always wanted to slap, now had, and would soon be sharing with others now the naughty little sissy had confessed to everything.
   I, MAXWELL TURNER AM A NAUGHTY LITTLE SISSY
   That was the line she'd made him write, two hundred times, in one of Sarah's old school books. Her work from six years previously in the front part, dotted with artful drawings of unicorns and rainbows. His at the back. All neatly numbered, with surprising neatness given he was uncomfortably seated at the desk he never used for his homework.
   Perhaps it was all the jiggling about, which made him soil the panties. Maybe it was the panties themselves, pulled so tight across his little tube and grapes, which made the mess more likely? It didn't matter to Amy, she just needed the photographs, to "Prove" how much he liked being the sissy she'd made him into, and to provide her with a cast iron alibe for all the things she was planning on doing to him. After all, who could blame a loving step-mum from helping out a wayward little boy achieve his dreams? Not her husband, that was sure.
   Harry Turner had barely batted an eyelid when Max had walked downstairs showing all sorts of leg. His eyes going straight to the bewitching woman walking behind the boy, even after his half dressed son was standing in front of him.
   "I'm sorry I was a naughty!" the adolescent robot voice repeated from Amy's scriptt. "I promise I will be good from now on."
   For a moment Harry had stared dumbfounded and yet, still missing  the slightly rough hems, around the shoulders of the dinosaur t-shirt which didn't reach the waist of the tight jean cut-offs, down to tiny ankle socks, barely visible outside of carpet slippers never previously worn. 
   "Yes, you've promised to be a good little..." placing her hand on Max's shoulder Amy prolonged the pause as long as she could, her mouth making the sounds of a forthcoming letter G, before changing the subject completely, and announcing she'd ordered supper in.
   Prompted with a pat to his sore bottom, Max was sent to lay the table without a mention of the television, quickly returning as he didn't know where most of the items he needed were kept.
   "Don't worry, I'll teach you." Amy smiled, her words not being as reassuring as they could have been once he'd collected their incoming meal from the doorstep.
   She'd expected a little bit of rebellion then, but although the boy's face was a picture of embarrassment, he dutifully went to the door, allowing her to even suggested how he would make a good maid, to his Dad, who roared with laughter, having little idea his wife wasn't joking.
   When Max returned with the two paper bags he found the cushion gone from his chair, replaced with a book large enough to lift his feet from the floor, once he was sat down, increasing the pressure on his bottom.
   Then it got worse for the thirteen year old boy. He was given salad!
   Again, he didn't argue, eyes flicking to the woman's phone sitting on the table on the far side. Her finger hovering as she told Harry about her plans for the following day.
   "Shopping!" was no surprise to anyone, however "Shopping for Max's new wardrobe." certainly was. Not least to Max himself.

Sandra B

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Re: The Naughty Sissy
« Reply #4 on: April 16, 2022, 04:54:39 PM »
Poor Max!  With a beginning like this, one wonders what the future has in store! I almost - almost but not quite - feel sorry for him.

 

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