Racing the clock, Jess pulled out a frilly pink dress and a handful of dainty white underthings, laying them out carefully on the bed. Despite his rising hysteria, there was a ritual he had to follow when dressing up, a sequence his Momma insisted on, even when he was preparing for a spanking. Everything had to be kept clean, fresh and utterly pristine. A single wrinkle on the frock could earn him an extra five minutes over her lap, and he had no desire to test her patience any further.

Running back to the closet, he fished about until he found the glossy red shoes his Mother had bought him for his last birthday. They were high heeled pumps, the kind made for teenaged girls making their first public debut - junior prom, dinner dance at the Lions club or whatever. She'd found them in a fashion boutique called Young Miss (Momma was always buying things for him to try on, especially when there was as sale downtown. Sometimes she even took him shopping with her, dolled up in tight blond curls and little pink miniskirts. These cross-dressed expeditions were an ordeal of suspense; the risk of discovery was overwhelming).

I hate this, Jess thought, scrambling back to the bed.

Placing the shoes on the floor, he stood looking down at the garments spread out on the bedspread, making a mental note of everything he needed: shoes, socks, underpants, vest and dress. A place for everything, everything in its place. Only four minutes left; no time to waste! Momma would be here anytime now. He had to get dressed. Now.

She's going to SPANK me!

Jess picked up the flimsy nylon panties, feeling a rich, crimson blush saturate his complexion. Shimmering white full briefs, they were covered with pale blue flowers and edged with a dainty pink frill. The very sight of them set his pulse racing. His tummy swirled with warm, fluid shame. The thought of wearing a pair of girl's underpants had him trembling with outrage. He was a boy, goddammit, a young man poised on the brink of maturity. What right did she have to humiliate him this way?

Hurry up!! She'll be here any second!!

Closing his eyes in childish denial, Jess stepped into the sheer, gossamer knickers, gliding them slowly up his legs. The sleek material rustled against his flesh. He felt a rush of fearful excitement – the touch of nylon always preceded the agony of a spanking. His head began to swim with conflicting emotions - embarrassment, guilt ... and pleasure. That was the strangest contradiction of all. Much as he hated being paddled like a naughty schoolgirl, he invariably experienced a thrill of wild exaltation when his discipline was imminent.

The singlet! quickly!

Of course, it wasn't a singlet, not the sort any boy would want to wear. It was a white floral vest, a perfect match for the panties (except that it was made of cotton), right down to the rosy trim around the edges. Gaping with embarrassment, Jess pulled the vest on over his head. Taking a few seconds to smooth out the creases, he tucked it carefully into his panties, precisely as he'd been taught since early childhood. Everything had to be perfect, a single mistake would incur the severest penalties. He turned to check himself in the mirror -

And Jess was no longer a boy.

Jessica Hoskins stood scrutinizing her reflection, her sumptuous golden hair cascading down past her shoulders. With the late morning sunlight streaming in through the bay windows, she was a fragile, delicate nymph, her alabaster skin gleaming like polished marble. Her figure was taking on the lush contours of dawning womanhood: from her slender, tapering legs to her wide, curving hips, she was blossoming like some ripening, succulent fruit.

Illuminated by a subtle backglow, she stepped back to her bed and picked up her brief, pastel sun-dress. Her heart hammered against her ribs as she drew the frock on over her head and settled it lightly into place. Jessie was scared: she'd been unforgivably naughty, and Mommy was going to smack her bottom. She swiped her eyes with the heel of her palm, sobbing in open fear. This was all Jess' fault; he was the one who'd curled his lip, lost his temper and broke all the rules. It just wasn't right. She hadn't done anything. Couldn't Mommy see that?

She sat down on the bed and pulled on her prim white girl-socks. They were her favourites, the ones with the pretty lace frill around the top. She loved wearing them whenever Mommy took her out shopping, they made her feel sweet, lovely and very, very feminine. Of course she didn't feel that way now - she was getting ready for a spanking, and the last thing on her mind was how nice her socks looked. She turned an ear towards the doorway, listening in rising panic. Footsteps were ascending the staircase. Ominous, determined footsteps.

Mommy was on her way up!!

Moaning with desperation, Jessie squeezed her feet into the slick red pumps and tightened the straps about her ankles. In a matter of seconds, Marion would walk in through the door and her spanking would begin. She would be turned over Mommy's knee with her tender young bottom-tops on rude display. The image froze her pulse in mid-beat. It was going to hurt. So much!

Why did Jess always get her into trouble? This wasn't the first time she'd been punished for his errors. It was as if he were doing it deliberately; getting Mommy angry then leaving her to face the consequences. And today it would probably be a lot worse; today she'd almost certainly get the hairbrush.

Those heavy, clocking footfalls were in the hallway now.

Nooooooooo, Jessie whispered to herself. She stood up and ran a last minute check over her dress, hair and shoes. She hadn't had time to tie a bow through her thick, blond tresses; she could only hope her Mother wouldn't notice this single, insignificant oversight. Not much chance of that, though; Mommy's eyes were sharp. She never missed a thing.

Jessie skittered over to stand before the SPANKING CHAIR with her face downcast and her hands clasped protectively over her bottom. She tried to shrink inside herself, look as small and harmless as possible. It wouldn't do any good, wouldn't lessen her sentence by even one stroke; she was aware of that. But the hope of a twelfth-hour acquittal tortured her nevertheless. She didn't want a spanking, didn't deserve it!!

Mommy's footsteps were right outside the door now. Jessie turned to face her, choking down her tears and all but praying for divine intervention. Please not the brush, she thought over and over, the words filling her mind in gigantic neon letters, please not the brush, please not the brush. She caught herself trembling with expectation, knowing how hot and red and sore her peach would be in a matter of minutes.

Mommy appeared in the door.

She was carrying the brush.

Jessie lapsed into a litany of desperate pleas as Marion entered the room. She strode towards the spanking chair, her face calm but etched with purpose. The antique ebony hairbrush glinted menacingly in the sunlight. It was the realization of Jessie's worst nightmares, a sign that this would be a long and extremely painful spanking indeed.

"No, Mommy, NO," Jessie wailed in a high, quavering voice, "not the BRUSH, please not the brush, it HURTS too much, PLEASE MOMMY don't SPANK me with the HAIRBRUSH -"

Marion ignored Jessie's fervent pleas, seating herself comfortably on the chair and steeling herself for the task ahead. This would be a most satisfying experience for all concerned; Jess would shriek and struggle over her lap, kicking his feet and screaming for mercy. And then, the spanking would really begin.

"All right, that's enough!" Marion exclaimed, slicing through Jessie's breathless entreaties with a stern, unforgiving glance, "you worked very hard to earn this reward, young lady, and you have no one to blame but yourself." Emphasis on the words young lady; as far as Marion was concerned, if Jessie insisted on behaving like a naughty little girl, she'd be treated like one as well. Considering the situation, it wasn't difficult to view her wayward son as a rebellious young daughter. At the end of the day, he - she - was a natural for the role.

"Now," Marion continued, testing the brush against the flat of her palm, "I've put up with enough of your sullen moods and disrespect, Jessica. It's high time you were taught a lesson in common courtesy. I've tried to reason with you, talk you through these temper tantrums. That was a complete waste of time - naturally enough - and frankly, I'm sick to death of your attitude. If talking isn't having the desired effect, there's always the alternative isn't there? Let's see if a good, long SPANKING won't solve your little communication problem."

On the pronouncement of this verdict, Jessica's nerve broke completely.

"No, Mommy, please, I'm sorry, I didn't mean it, really I didn't, I take it all back, PLEASE don't be cross, PLEASE don't SPANK me, I'll be good from now on, honestly I will -"

Marion listened to Jessie's quailing petitions, vaguely amused by the radical change in his character. The transformation hadn't been confined to the boy's appearance; his whole personality seemed to have altered. His strutting, boyish animosity had vanished the moment he donned the sun-frock. Twenty minutes before, he'd been screaming abuse at the top of his lungs, now he was begging her forgiveness with tears in his eyes. He was even calling her 'Mommy', something he never did under any circumstances. It was amazing what an hour or two of 'Jessica-time' could do for her boy's normally belligerent temperament - particularly when a hot, throbbing bottom was on the cards.

Which brought her back to the issue at hand. Punishment should never be tempered by remorse, no matter how sincere. Jessie had been inexcusably rude on the drive home, and Marion was determined to see that justice was done in this case. Leaning forward on the chair, she transfixed her simpering boy-daughter with an impaling glance.

"Stop that crying RIGHT NOW!!" Marion instructed, brandishing the brush in her right hand, "You're going over my knee whether you like it or not, young lady. You DESERVE a spanking, and that is PRECISELY what you're going to get. Now -" she paused, slapping the brush into her hand to reinforce her point, "I want you to come over here, bend over and lift up your skirt."

Jessica gasped, stamping her feet in childish refusal. It was time to bare her bottom! She hated this almost as much as Jess hated dressing up in girls' underwear; it was so juvenile, so embarrassing, so utterly degrading.

"No, Mommy, no, noooooooo!!" she begged in keening, frantic tones, "don't make me take them down, spank me over my panties, please Mommy, you don't know how awful it is for me, please don't -"

"You GET those PANTIES down NOW!!"

Groaning in utter humiliation, Jessica doubled over from the hips, flipping her dress over her back like a can-can dancer. Her virginal white underpants were immediately thrust into view; her plush, yielding cheeks literally bulging through the gossamer material. Reaching back, she hooked her thumbs through the elastic trim, pausing momentarily before peeling the sleek nylon briefs down her thighs.

Marion nodded to herself in evident satisfaction as her daughter's soft, creamy buttocks were revealed. Jessie had a delicious little bottom, no question of that (which was probably why she enjoyed spanking it so much). Leaning slightly forward, Marion laid a loud, stinging slap on each of the girl's buxom cheeks. Lush, round, and deeply dimpled, they quivered with each resounding smack. Jessie cried out in surprise, her buns twitching from side to side.

"No Mommy, no, please don't, I'm sorry, noooo ..."

Marion smiled ruefully, as if expecting nothing better. Well, time to get started. Couldn't spend the whole night admiring the view, so to speak. She had a job to do - one she found much to her liking, truth be told. No point waiting any longer. Business before pleasure, as her dear departed father had been fond of saying.

"All right, my girl," Marion said, taking Jessie by the right hand, "let's get you over my knee."

"Mommy, NOOOOOOOOOOOOO!!" Jessica wailed as she was led over her Mother's lap. Marion guided the helpless, sobbing girl into place, settling her bottom into the central position. Her pale, unprotected cheeks clenched and primped with anticipation. Heart literally hammering against her ribcage, Jessie whispered her final, tearful pleas, knowing her spanking was only moments away now.

"I'm sorry Mommy I didn't mean it really I didn't please don't ..."

Marion raised the brush, tensing the muscles along her right arm.

"OK - hold still and stop that wriggling", she warned, "you've had this coming for weeks now, and this is one lesson you won't forget in a hurry!!"
The brush streaked down, faster than the eye could follow.

Jessica screamed.

Marion's hand swept up and down with stunning force, burning its splayed print into the girl's quivering cheeks. A volley of ear-splitting shrieks filled the room. The time for whispered pleas had passed; Jessica's lungs could barely contain her screams as she twisted and squirmed on her Mother's lap. Her eyes bulged from their sockets, her legs thrashed in agony.

Marion held her daughter firmly in place as he seared her hynie up to a fine, subtle pink, pressing down on her back to prevent her rolling off her knees. Her peaches pumped and danced in response to those loud, reverberating slaps; huge, glistening tears streamed down her face. She howled incoherently, conscious of nothing save the white-hot pain flashing across her posterior.

Jessie beat her palms on the floor, wailing like a soul in purgatory. It was her worst nightmare: she was having her bottom smacked! Marion was tanning her naked fanny-tops, bruising her dignity as if she were nothing more than a naughty little girl. She was breathless with shame, hurt and wounded pride. Marion's hand blazed from side to side, relentlessly scorching its way around her derriere. Her cheeks felt huge and swollen, the flesh drawn tight as a drum.

"NO!! OOOWWW!! MOMMY!!! NO!!! IT HURTS, IT HUURRTS!!"

Indeed, it did: Jessica's bottom was literally smouldering with crimson heat. Marion dismissed her yelps with an impatient grunt, laying in with a vengeance. She'd had this coming for weeks now: Marion was determined to show her who wore the pants in this family once and for all. She'd make sure this was one lesson Jessie would never forget - no ifs, ands or buts about it.

"AAAA!!! MOMMY, STOP IT!!! OWWWW!! NO!!! I'M SORRY!! OWWW!! DON'T!!! AAOOOW!!! NO!! STOP!! PLEASE!!! NO!!"

Jessica bawled in misery. Her denuded bottie was as red as a traffic light, as sultry as a tropical sunrise. It rippled and shook with each smarting crack, flickered and shone with a simmering, carmine light. Marion's palm lashed into her cheeks, her bulbs, her thighs. Jessie shouted out her pleas in a high, keening voice, begging her Mother for an end to her ordeal:

"OWWW!! MOMMY PLEASE STOP IT HURTS REALLY BAD OWW!!! NO!! DON'T MOMMY!!! NO MORE!! PLEASE!!!"

Some minutes later, when Marion was satisfied her sorry little miss had been sufficiently chastened, she lowered her hand to one side, shaking out the pins and needles with a rueful smile. She felt a kind of grim, tired pleasure: it had been a long, hard day and now She could relax in the knowledge of a job well done. Her daughter's errant bottom had been spanked the colour of a passion-fire rose. The verdict had been pronounced, the sentence carried out, and justice served for one and all. Now it was time to rest on her laurels.

Jessica lay doubled over her Mother's lap, quietly sobbing over this latest humiliation. How could this have happened to her again? How could she have bared her tushie with hardly a flicker of resistance? She'd given in so easily, and offering up her naked fesses as if she'd actually deserved to be punished. Could there be anything more embarrassing?

Worse still, her freshly-smacked bottom felt as though it had been sitting in a blast furnace for the last hour; she'd probably have to sleep on her belly for the next month! Her cheeks seemed to pulse and throb with each thudding heart-beat. Closing her eyes, Jessica imagined her melons inflated to three times their normal size, heat rising visibly from her sizzling, purple flesh (probably nowhere near that bad, of course, but that was how it felt).

"It hurts, it hurts ..." Jessie cried softly, her botts trembling like two bowls of raspberry jelly.

"I should say it would," Marion agreed serenely, unrolling her sleeves with the air of a woman well-pleased with recent developments. Things had worked out for the best. The law had been upheld, the culprit punished, and now she could look forward to a quiet evening in front of the box with her feet up on the coffee table. What more could a woman ask for?

Guess there's nothing like a good, hard spanking to turn a bad day completely around.

The following few months witnessed a remarkable transformation in Jessie's character. Marion imposed a strict policy of Zero Tolerance over her conduct, under which the smallest infractions would be punished with hot, throbbing bottom. No questions were asked, no excuses were accepted: the instant she stepped over the line, she was made to lower her panties for the paddle. The result was sixty days of continuous spanking, during which Jessie's pert young botts were constantly smarting. Spanked on average at least twice a week, her fanny became intimately acquainted with a variety of wooden spoons, rulers, hairbrushes and anything else that could bruise a preteen's bottom. Hardly a week went by when her cheeks weren't pinkened for one reason or another (not that she had any cause to complain, mind you – Jessie only ever got what she deserved). It was juvenile, it was demeaning, it was embarrassing beyond belief - but Jessica knew better than to object.

The spankings began to taper off once the probation period had passed, but Julie warned her that the brush would be brought forth at the first sign of rebellion – a threat Jessie took very seriously indeed. Well aware that her mother would make good on her promise at the earliest opportunity, Jessie applied herself to improving her behavior. The transformation was both immediate and impressive. Lacing an apron around her waist, she became the very model of the houseproud preteen, performing her chores without complaint. Spending more time at home led to a steady improvement in her grades, and she somehow managed to resist the temptations offered by her more masculine associates.

Oddly enough, it wasn't long before she found herself back over Marion's knee. Despite her best efforts, Jessie simply couldn't control her adolescent temper. Like any other "girl" her age, she naturally felt some degree of resentment towards her over-protective guardian and made her sentiments known at regular intervals. Such confrontations invariably led to one of her Mother's "High Level Discussions", most of which involved a one-sided exchange between Marion's hand and Jessie's bottom (it goes without saying that Marion proved to be a most engaging conversationalist). Such debates generally lasted around fifteen minutes, give or take a few 'breathers' as circumstances required.

More significantly, cross-dressing became a normal, almost integral part of her life – along with the tears, shame and disgrace she suffered every time the Marion scorched her buttocks. It was, perhaps, the sole constant of her existence, as unvarying as the phases of the moon. In time, she almost stopped thinking of herself as a boy; due – in part – to the amount of time she spent in girl's clothing. As each day went by, Jessica was exposed to an increasing variety of skirts, frocks, dresses and slips, to the point where her Mother decided it was more convenient to keep her son in panties on a permanent basis.

Of course, Jessie was not the first boy to succumb to the irresistible allure of satin and lace; particularly not in the picket-fence paradise of Lainsbury. In a city where pinafore discipline was as common as fluorodized water, it might have been considered unusual if she hadn't…

Visit the Transfiction Wiki