Transgendered spanking story

DerPantsu · Panty "BRONZE" Joined: Jun 27, 2011 Posts: 8

Here's the intro to a story I wrote some years ago, combining two of my favorite fantasies. For those of you who long for a strict, loving aunt to take you firmly in hand, I present:

CROSSING THE BOUNDRIES

1.

"All right, that’s IT, young man!!"

Marion Hoskins was at the end of her tether. She’d had the worst day in recorded history and the last thing she needed was another screaming match with her nephew. The boy had been testing the limits for more than a week now, and she’d finally decided it was time for some direct action. All she wanted was a little old-fashioned respect, after all. Recognition for the long hours she put in at work; for her senior status within the household. Sixty hours a week in the office from hell and all she could look forward to was a mouthful of Jess’s sneering contempt. Well, all that was about to change. At the end of the day, she deserved better than this. She was the one who brought home the bacon, for Chrissake!

"Get up to your room this instant," Marion growled, scowling down at the boy from withering, arctic heights, "You have ten minutes to get ready!"

Jessie’s eye widened with dawning horror. Ten minutes head start could only mean one thing.

"Noooooo!" Jess cried, knowing precisely what she had in store for him, "PLEASE, Aunt Marion - anything but a SPANKING!!"

His posturing, teenaged pride had evaporated in a matter of seconds; Jess had good reason to fear Marion’s anger. If only he’d managed to keep his mouth shut on the way home. He knew from painful experience that she wouldn’t tolerate any of his snide backtalk. There were certain boundaries that should never be crossed; the consequences were too dire to contemplate.

Unfortunately, the time for negotiations had long passed. Marion had already made her decision, and nothing would alter her verdict. And that was one thing Jess could count on.

"Get up to your room NOW!!" she snapped, leaning in close to the boy and pointing towards the staircase. A single vertical line appeared on her forehead, directly between her eyebrows. Jess’s heart sank; he knew that sign. His Aunt wasn’t simply angry - she was down right furious. A chill of suspense played his spine like a xylophone. Whimpering in protest, he turned and fled for the staircase, his long, blond ponytail flaring out in his wake.

Marion watched him hit the stairs at a full run. A tall, athletic woman in her early thirties, she stood with one hand on her hip, forcing her pulse to drop back to its normal pace. Jess was long overdue for discipline, and she wanted to be completely calm when she entered his bedroom. The task ahead would require her full concentration, and she intended to savor every squirming, twitching moment to its fullest extent.

Where was that brush?, she thought, glancing around the living room. The one with the teakwood finish, as smooth and dark as baby grand. She usually kept it on the mantelpiece over the fireplace, where it would always be within easy reach. Marion normally applied her open hand to Jessie’s errent bottom, but today, she felt the circumstances required a little something extra. A grim smile touched her full, red lips.

I’m going to enjoy this, Marion thought, walking across to the fireplace.

2.

Jess bolted up the stairs in tears, his expensive Nike sneakers pounding the steps two at a time. He was literally overwhelmed with shame and fright; it had been more than four months since the last spanking, and he knew this would be far worse than a couple of glancing smacks on the tail. His Aunt wasn't simply angry this time. She was utterly livid. He never should have picked that argument with her on the way home. What had he been thinking, testing her patience over such a trivial matter?

She’s going to SPANK me!! Jess thought frantically, wiping the moisture from his cheeks. He sprinted along the upstairs passage way and headed for his bedroom door. He couldn’t afford to drag his heels. He had to prepare for his punishment. If he wasn’t finished by the time she arrived, things would probably go a lot worse for him.

At eighteen years of age, there were very few things Jess hated more than a spanking. He would gladly have endured grounding for a year to avoid going over Marion's knee. Of course, no such options were available on this occasion. Nothing could temper her judgment once she’d made up her mind. Hot tears began to fill his eyes. He could already feel her wide, scarlet handprint burning into his naked buttocks.

Running through the doorway, Jess paused a few feet from his bed and stood looking around the room, his face a mask of trepidation. How much was it going to hurt this time? Was she going to use the brush, that long black heirloom she kept on the mantelpiece over the fire? He’d only felt its touch a handful of times, but he dreaded it more than any other implement his Aunt employed. The last time she’d applied it to his tender young bottom-cheeks, he’d had to eat standing up for nearly three days.

Sobbing in misery, Jess went over to his study desk and started dragging the old, straight-backed chair into the middle of the floor. He’d come to think of it as THE SPANKING CHAIR, the site of a thousand bare-bottomed torments. It was a constant reminder of his juvenile status within the family hierarchy, the fact that Marion was his Aunt and he would always be subject to her authority.

Shifting the chair to its venerated position, Jess went over to his built-in closet. He hesitated before the folding door, his belly tensing up in apprehension. Now came the part he loathed the most; the thing he despised more than any other part of this ritual of disgrace.

It was time to get changed.

Stealing a glance at the clock (less than six minutes to go), Jess began to undress, pulling off his t-shirt and unbuckling the belt of his jeans. He bit his lower lip, whimpering in consternation. Why did he have to do this? It seemed so unfair, so terribly unjust. Everyone deserved at least some measure of dignity, no matter what they’d done to incur the familial wrath. Even convicted criminals were accorded better treatment than this.

Tossing his jeans and underpants into the laundry hamper, Jess reached back to remove the band from his ponytail. And at that moment, Jessie Hoskins no longer looked like an eighteen year-old boy. He didn’t look like any kind of boy for that matter. With his long, curvaceous limbs and his slightly protruding belly, he seemed slim, petite ... vulnerable.

Sniffling like a child lost in the rain, he folded the closet doors back into themselves and surveyed the interior. His soft, child-like features melted with dismay. He’d known what was awaiting him, but a vast wave of despair overpowered him nonetheless.

The closet was full of dresses.

And there it was: the ultimate humiliation. Marion always insisted he dress up as a young girl whenever he was due for a trip over her knee. She had instituted this rule nearly six years ago, and had enforced it ever since, brushing aside his protests with barely a second thought. It was the most degrading thing he could imagine, a betrayal of his teenaged masculinity - being forced to slip into a pair of lace panties and a frilly sun-frock ... prior to having his bottom tanned the color of a ripe raspberry.

3.

Five minutes.

Racing the clock, Jess pulled out a sheer pink dress and a handful of dainty white underthings, laying them out carefully on the bed the way Marion had taught him. Despite his rising hysteria, there was a ritual he had to follow when dressing up, a sequence his Aunt 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 a little extra "attention" over her lap, and he had no desire to try her patience any further.

Running back to the closet, he fished about until he found the glossy red shoes his cousin Shirley 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. Cousin Shirley owned a fashion boutique called Young Miss; she was always buying things for Jesse to try on (Jess sometimes imagined his entire family was in on a conspiracy to turn him into a sissy, molly-coddling him into a state of helpless femininity).

He scrambled back to the bed, placing the shoes on the floor. He looked 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! Marion 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 thighs. 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 Jessie was no longer a boy.

4.

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 flesh shining 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 on the way home from school, and Aunt Marion was going to smack her bottom. She swiped her eyes with the heel of her palm, sobbing in open fear. It just wasn’t right, she didn’t deserve this. Couldn’t Marion see that?

She sat down on the bed and pulled on her prim white girl-socks, the ones with the pretty lace frill around the top. They were sweet, lovely and very, very feminine; the kind of things worn by rosy-faced girls with long, curling pigtails. Of course she had no time to dwell on such things right now - she was getting ready for a spanking, and the last thing on her mind was how her socks looked. She cocked an ear towards the doorway, listening in rising panic. Footsteps were ascending the staircase. Ominous, determined footsteps.

Marion 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, her Aunt would walk in through the door and her spanking would begin. She would be turned over Marion’s knee with her tender young bottom-tops on rude display and her panties down to her knees. The image froze her pulse in mid-beat. It was going to hurt. So much!

Why did she always get herself into trouble like this? This wasn’t the first time she’d been punished for her incessant backchat. Getting her Aunt angry always led to a painful finale, and today it would probably be much worse that usual. 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 Aunt wouldn’t notice this single, insigificant oversight. Not much chance of that, though; Marion’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 behind her back. 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 hopes of a twelth-hour acquittal tortured her nevertheless. She didn’t want a spanking, didn’t deserve it!!

Marion’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.

Aunt Marion appeared in the door.

She was carrying the brush.

To be continued. Please leave a message if you're interested in reading more.

PantyPeter · Posted: Sun Aug 21, 2011 12:55 pm Post subject: Re: Transgendered spanking story

Very well written. Impressive literary skills. Yes, I really want more. Does she have sex with the aunt?

Do you have any more stories you've written?