Jessie's Day
Note: the protagonist of this story is biologically male but looks anatomically female.
Jess Taylor ambled swiftly up the driveway, fishing his keys out of his pocket as he approached the front door. He was a boy on a tight schedule; his Mother would arrive home at five, dinner would be on the table no later than six. That left him less than three hours of free play; three hours of simple, childish joy in the late September sunshine, three hours on the swings and slides and monkey-bars down at O'Connell Park.
Heart pounding with excitement, Jess let himself into the house, dropping his backpack in the hallway. His Mother would probably give him grief over that later, but he was in too much of a hurry to consider the consequences. Heading towards the staircase, he unzipped his jacket and bolted up the steps two at a time. It was 3.15 in the afternoon; the day wasn't getting any longer.
Leaving his jacket hanging over the banister, he scrambled into his bedroom, hurriedly pulling his t-shirt over his head. Six hours a day in the school from hell, surrounded by creeps, cretins and bullies. He couldn't wait to get changed, kick off his school clothes and slip into something more comfortable - so to speak.
Pausing in the middle of the room, Jess climbed out of his jeans and walked over to the closet, a petite, twelve-year old boy with long blond hair and pale blue eyes. His soft, effeminate features lent him a lush, girlish appearance, the illusion further enhanced by his rounded, curvaceous shape. Exceedingly pretty, he was often mistaken for a girl at first glance. Strange to say, this was something Jess didn't mind at all.
Jess, you see, was a very special boy.
He opened the closet door and started sorting through the racks and hangers. One side of the space was full of boy's clothing - pants, shirts, gym socks, boxer shorts and runners. Jess didn't spare it a second glance. Boy's stuff; ugly, scruffy things, he'd never had much use for them. He certainly never wore them once he got home from school. The moment he stepped in through the front door, Jess was free to shed his male identity as a snake sloughs its skin. He could be his real self.
Jessica.
The right side of the closet was lined with cutesy little girl's things: skirts, vests, tank tops; printed floral blouses with puffy sleeves, drop-waisted sunfrocks with outrageously frilled hemlines. They were all gifts from his Momma; stock-taking specials from her downtown kidswear store. Strangely enough, she'd always been surprisingly tolerant of his feminine preferences, even going out of her way to encourage his cross-gendered behavior. Jessie suspected it had something to do with her not liking men.
Jessie reached into the closet and removed a pastel pink sun-dress, a delicate cotton wisp decorated with tiny rosebuds around the neck line. Sheer, loose and almost unbearably cute, it was one of his all-time favorites. Momma had helped him pick it out for his last birthday. It had been one size too big at the time, but he'd grown into it over the past nine months.
Laying the frock out on his bed, Jess walked over to his chest of drawers and took out a pair of pristine white panties - flimsy cotton briefs with a dainty trim encircling the legs and waistline. Jessie's pulse began to race as he stepped carefully into the underpants and drew them slowly up his thighs. Easing the pants into position with a loud, elastic snap, he went back to the bed and pulled the sundress over his head.
And, in the blink of an eye, a boy became a girl.
Smoothing the cool fabric against her tummy, Jessie turned to look in the mirror, smiling at what she saw. The boy she been a few minutes before had disappeared without a trace. Jess Taylor had vanished the instant she'd kicked off the jeans. No - that was wrong. Jess Taylor had never really existed in the first place. He was just a mask she wore during school hours. A mask, a name, and nothing more (quoth the raven ...).
Giggling a child's innocent laughter, Jessica spun around several times to make the skirt twirl. The dress flared up in a pink arabesque, then floated lightly back into place. The hem barely reached down past the tops of her thighs; the cotton was so thin that her underpants were clearly visible through the gauzy fabric. She posed in the mirror, admiring the line of the frock, the shape of her long, tapering legs. Moistening her lips in anticipation, she whirled around once more, allowing the dress to sail up past her belly button this time.
Having completed the dress-twirling ritual, she retrieved a pair of socks from the drawer and sat down on the bed to pull them on, one tiny foot at a time. They were the kind with a lacy white frill decorating the band. He'd picked them up during a recent shopping expedition to Ridgewick Mall. Jessie had fallen in love with them at first glance, putting them on right there in the Stocking Shop, attracting more than a little attention in the process.
Jess stood up, glancing at the clock. It was 3.25; time to go. Her friends would be wondering where she was. Stepping into her pink Barbie runners, she grabbed a black hair-band on her way out and tapped off down the hall. She descended the stairs at a gallop, binding her hair back in a long, golden ponytail. Not a second to lose now, she'd have to sprint all the way to the park.
Jessie's Day
Note: the protagonist of this story is biologically male but looks anatomically female.
2.
Autumn in Ridgewick was known locally as "The Breezy Season," two chilly months of clouds, mistrals and dancing leaves. The winds blowing in off the Bucknell River held a promise of snow this time of year, whispering through the trees like the breath of winter. The days were usually mild, but temperatures dropped rapidly toward the end of the day.
Jessie's legs were buzzing with gooseflesh by the time she reached O'Connell Park. She held her dress down against the invading breeze with one hand. She could always count on an errant gust to lift her skirt an inch or two whenever she stepped out the front door: there were very few things as embarrassing as having her panties revealed to the entire world; all of her friends agreed on that point. Speaking of which, she knew she had to make tracks; Lisa and Debbie couldn't wait forever, they all had to get in a good hour of playtime before dinnertime.
O'Connell Park was a football oval on the outskirts of Ridgewick; the River lay just beyond a slight rise. There was a small playground on the other side of the playing field; Jessie could see her friends rocking sedately back and forth on the swings. Both girls were wearing baggy jeans, faded sweat shirts and Dodgers baseball caps, their ponytails pulled through the backstrap. As long as she'd known them, Jessie had never seen either wearing a dress. Shorts, yes, knee-pants sometimes, but never anything even vaguely resembling a skirt. Neither were tomboys so far as she could tell. It was simply the way they dressed.
Well, to each their own, as her sainted mother often said.
Jessie cut across the oval, where an exceedingly violent game of football was in full swing. She knew many of the boys by sight now; most of them went to St Patrick's over on Lincoln Road. Lean Irish lads with chestnut hair and about six zillion freckles. The majority were Jessie's age, though she'd noticed a few older guys chasing the ball lately; kids from St Paddy's seventh grade, she judged. Seemed to be more every week.
She skirted around the game, ignoring the covert boy-glances, and headed towards the playground. Her friends were still seated on the swings, idly dragging their feet through the turf. Noting her approach, Debbie called her name and raised a hand in greeting. Jessica waved back, careful to retain her grip on the wayward skirt.
There was a low chain-link fence dividing the oval from the playground. The opening was on the far side of the park, and Jessie had no intention of walking half a mile to use it.
"Hi," Lisa called from the swings, "didn't think you were coming."
"I got out late today," Jessie replied, setting a hand on the fence-rail. The back of her frock filled up like a sail as she climbed over, although she managed to preserve her modesty by clamping down on her drifting hemline. Quite a trick, considering how short the dress was. Had to be careful; these wintry updraughts loved to catch you unawares.
Clearing the fence, she walked over to the swings and took her place between her two friends. All three began swinging in unison, gradually increasing their velocity. Overhead, the endless blue sky seemed to revolve above them.
"Late?" Debbie asked doubtfully, "you in dutch with your teacher?"
"No, we had dance practice after school." Jessie straightened her legs, pointing her feet towards the sky. Her dress began a steady hike along her thighs, inching its way up to her panties.
"You take DANCE CLASS?" Lisa asked incredulously, as if this was some momentous revelation. She looked genuinely thunderstruck, as if someone had told her that the tooth fairy wasn't real.
"Yeah, every Thursday afternoon", Jessie replied, arching her back for greater height, "my Mom says I have to go. Says it's important." Another inch, two. A rush of air slipped around her thighs, lightly flickering her hemline
"Why?" Lisa, again.
"She says all girls need to know how to dance," Jessie shrugged. She swung faster now, long blond pony tail trailing out behind. The dress had crept up nearly three inches, making her bare legs look impossibly long and slender.
"So, what are you learning?" Debbie wanted to know.
"A lot of things," Jessie answered, "tap, ballroom, modern jazz." Her skirt slid one final, teasing inch to the top of her thighs. The hem was now quivering at the very edge of her panties. Jessie glanced down, feeling the wind gathering strength at the tip of her underpants.
"What about ballet?" Lisa inquired, eyes still goggling with disbelief.
"Well...not so much now," Jess replied offhand, "I did ballet when I was little, before we moved to Ridgewick." The edge of her hem began to rise, just the barest fluttering of pink cotton. The suspense was unbearable: her underwear was about to go on display. The dress was going to blow up around her hips, everyone in the park was going to see her panties. It was unavoidable, inescapable.
"Hey, do you have to wear a leotard or anything?" Debbie inquired, showing an unexpected interest in all things girly.
"Sometimes. But usually, we just practice in whatever we're wearing," Jessie explained, soaring ever higher. Her tummy seemed to be swarming with butterflies, her heart pounded in her chest like a triphammer. The lining of her dress flickered once, twice, settled - then flickered again. The capricious Autumn winds played around her thighs, chasing their way up with icy, tickling fingers. She clung to the swing-chains with both hands, moving way too fast to let go and hold her dress down.
"Do you have to put on a show?" Debbie asked. Jessie gave a start, almost nipping her tongue despite herself.
"At the end of the year, maybe," she affirmed, wheeling off into the wild blue yonder, "we have a school concert around Christmas." A cold thrill ran the length of Jessie's spine: her skirt was dancing a fraction of an inch above her thighs, but the lace trim of her panties remained just out of sight.
"We're having a school concert in SEPTEMBER," Lisa cut in, running off at the mouth like a country housewife, "DEBBIE'S going to be in it, she'll be doing this ROUTINE with her GYM CLUB - you know she does GYMNASTICS, don't you Jess?" She looked over at her friend, eyebrows raised expectantly.
Jessie opened her mouth to answer - and the front of her dress ballooned up like a huge pink bubble. A frigid gust of air blasted up her thighs, inflating her skirt and chilling her belly. So abrupt, so unexpected, so breathtakingly cold. Jessie gasped with shock, watching the dress bulge and ripple literally right before her eyes. The hem flew up past her waist, offering the world a heart-stopping view of her silky white underpants.
Vaguely aware that Lisa was still prattling on about the school concert, Jessica streaked forward on the swing, her panties fully visible clear up to her belly button. The breath caught at the back of Jessie's throat, her cheeks flushing with embarrassment. This had never happened before, not in all the months she'd been hanging out here with her friends. Her eyes bulged in shock as the bubble continued to swell.
Stifling a little scream, Jessie began kicking her legs in a vain attempt to deflect the breeze. Needless to say, her plan immediately backfired, revealing more of her virginal white panties to the world. Lisa and Debbie started laughing as her frock inflated towards the heavens. They both loved Jessie to pieces, but it was utterly hilarious, nonetheless. This was why they always wore jeans to the playground!
Blood roaring in her ears, Jessica swung in a great, looping arc, biting her lip to hold back her screams. The wind was still picking up, threatening to peel her dress off completely. Her mind's eye magnified the spectacle as only a child's imagination can: she could almost see the floral pattern sewn into the front of her snowy white undies, glimmering in the afternoon sun. It seemed to go on forever, the moment spinning out to eternity -
Then the bubble finally popped.
Jessie's billowing dress collapsed in on itself, the front turning inside-out for good measure. The wind pasted the skirt against her torso, leaving her panties completely uncovered. Hair flailing in the gale, Jess fought an impulse to lower her hemline to a more demure position. She felt as if everybody in Ridgewick was staring at her underwear.
Still giggling at Jessie's discomfort, Lisa turned her feet towards the ground and allowed herself to deccelerate. Debbie followed after a few moments, matching her speed with the ease of long practice. The two girls leapt gracefully off the swings, touching earth in perfect synchronicity. They turned back to look at their pretty blond playmate, still struggling to conceal her shimmering nylon briefs. All three had lasped into good natured laughter.
Jessie's Day
Note: the protagonist of this story is biologically male but looks anatomically female.
3.
Jessica stepped down from her swing, primly adjusting her dress. Her hands shook imperceptibly as she smoothed out the rumpled fabric. She felt dizzy, short of breath; a faint crimson blush tinted her face, neck and shoulders. She'd never shown so much panty in her life. Nothing more than a flash of lace around the bottom, even on the windiest days. Today, every inch of her chaste white knickers had gone on exhibit. Every stitch, every seam, every frill, right down the little red tag on the waistband. Nothing had been left to the imagination.
Having laughed herself breathless, Debbie began looking round for some other way to humiliate her best friend. The perfect opportunity presented itself almost immediately. "Wanna climb the monkey bars?" she asked, indicating the jungle gym.
"OK," Lisa agreed, gleefully imagining her companion hanging upside down with her dress over her head. "You in, Jess?" she inquired in an overly casual tone, carefully calculated to drive the point home.
"No," Jessica replied, knowing precisely what her friends had in mind. Her hands flew protectively to the front of her dress as the wind threatened to whip it up in her face. All three burst into sweet, tinkling laughter once again.
"Come on," Debbie teased, tilting her head in a vaguely challenging manner, "it'll be fun. I'll race you to the top."
Jessie shook her head in girlish refusal, her cheeks still burning like an Arizona sunrise. At this point, they couldn’t have payed her to climb up there, not after that panty-flashing fiasco on the swings. Why hadn't she worn shorts under her dress, same as every other girl on the planet?
"You're just afraid the boys will see your underpants!" Lisa jeered with a kind of sugar-coated malice. Jessie's complexion flared even brighter.
"Am not."
"Are too!"
"Am not!"
"Are TOO!!"
"Am NOT!!"
"Are TOO are TOO are TOO!!!"
The last exchange settled the matter for all time, being the feminine equivalent of the infamous triple-dog-dare. Jessie had no choice now, she had to climb the jungle gym and prove she wasn't afraid to let every boy in Ridgewick see her panties.
"Last one up has to kiss a pig!" Lisa yelled before Jess could find an excuse to back out. Squealing with laughter, the girls bolted over to the bars and clambered up the rungs in a tangle of hands, feet and elbows. Debbie claimed the first place by virtue of her superior athletic abilities, Lisa and Jessie tying in second.
Once at the top, the three perched together gazing out across O'Connell Park towards the center of town. As young children, the monkey bars had seemed infinitely tall and steep, a vast, looming monolith overlooking half the planet. Nowadays, the view was considerably less impressive, encompassing only three or four states.
"Know who I saw holding hands with Suzy Chatterson?" Debbie asked, apropos of nothing in particular. Lisa cocked her head to one side, face lighting up at the prospect of some juicy, small-town gossip.
"Who?"
"Bobby Hilliard," Debbie replied nonchalantly. Lisa's eyes shot wide with astonishment, occupying roughly a third of her face.
"Bobby HILLIARD? But he's in the eighth grade!!"
"Yep. Saw them walking home together from the library yesterday," Debbie reported with an air of quiet satisfaction, "held hands all the way down Ridgewick Drive. You know Bobby Hilliard, Jessie?"
Jessica nodded indifferently, already zoning out. Her hands fumbled with the hem of her dress, which she knew was going to ride up around her panties at the earliest opportunity. It was one of those immutable laws of nature: a little girl's skirt rose in direct proportion to the proximity of her underwear. Her recent adventure on the swings had proven that.
"I can't BELIEVE Suzy's got a boyfriend in the eighth," Lisa rattled on, oblivious of everything apart from her own opinions, "I mean, he's like THIRTEEN and she's OUR age!!" Presumably, the relationship violated every known law of physics.
Jessie wasn't really listening, she was too busy replaying her recent adventure on the swings. Her dress had turned into a balloon, revealing everything she had on underneath: her lean, tanned thighs, her dainty white underpants, her pouty little belly-button. How would she ever live it down?
"Well, the way I heard it, Bobby is Suzy's second cousin or something," Debra was saying, electing to play devil's advocate, "so maybe they aren't actually going together..."
"Oh…yeah – second cousin," Jessie murmured, mostly to herself. She was having a great deal of trouble following the conversation; all she could think about was the way her dress had flown up over her waist a few minutes before. Worse still, she knew how this conversation was going to end. Sooner or later, Debbie would grow tired of Lisa's inane chatter. She'd get fidgety, grow restless, look for something else to do.
And here they were, sitting on the monkey bars.
"Yeah, but why was he holding her hand?" Lisa steamrollered on, "I mean, it's not like she's five years old or anything…"
Jessie completely lost the thread after that point, she had more important things to consider. Yes, here they were, sitting on the jungle gym, and Debbie was already looking bored with her friend's mindless drivel. Any second now, she'd lock her knees around one of the bars and swing herself upside down. Lisa would follow almost immediately, still jabbering nonsense. The two of them would hang there with their ponytails trailing towards the ground -
and then it would be her turn.
Jessie's features flared the color of a ripe raspberry. It was going to happen again. She had no choice in the matter: just like on the swing, there was nothing she could do to protect her modesty. Her pretty white panties were going on view once more: in a matter of moments, she would have to drop between the bars, dangling by her knees six feet above the grass. Her dress would turn inside out, drooping gradually over her head. Jessica's pulse accelerated, a wave of sultry heat swept through her tummy.
Meantime, the Bobby Hilliard controversy raged on.
"There's nothing wrong with them holding hands as long as they're just friends," Debbie pointed out in condescending tones, "it's not like they were caught kissing under the bridge." She glanced in Jessie's direction, rolling her eyes with a dismissive shake of her head – another tell-tale sign she was losing interest in the discussion.
Jessica lowered her gaze, trying to suppress a stream of nervous giggles welling up from her tummy. She couldn't help herself; Debs was getting ready to launch herself through the rungs. Jess could see it in her face; she was considering the action at that very second. There would be no last minute reprieve, no evading her just deserts. Jessie's fate was sealed. Her flimsy white panties were going on display whether she liked it or not. Why had Debbie opted for the monkey bars anyway? The playground was full of slides, round-abouts and teeter-toters. There was even a large wooden fortress – Fort O'Connell, scene of countless raids and massacres – over by the Big Dipper. Plenty of girl-friendly equipment which didn't require the lifting of her skirt.
"Yeah, well, I just think he should hang out with someone his own age," Lisa opined in the background, "he wears black socks with white shoes. You know what THAT means."
"… what's that got to do with anything?" Debra inquired after a pause. She straightened up and began swinging her feet back and forth beneath her.
Jessica's heart leapt into her throat.
Debs was preparing to go head over tail, she recognized the signals. Jessie cupped a hand over her mouth to conceal her rising trepidation. She felt warm and feverish, molten silver seemed to be pumping through her veins. The moment was fast approaching. Light-headed with expectation, Jess waited for her exposé to begin. Again, the suspense was almost unendurable.
Well, what's done is done, as her Mommy often said. The decision had been made. Jessie gnawed her lip in anticipation of the inevitable, heart pounding in her chest like a runaway stallion. The day wore on, the conversation continued and the interminable seconds trickled by into the endless Autumn afternoon...
Then, it happened.
Upfolding her legs without a word, Debbie leaned backwards and hooked her knees over a cross-bar. Slipping lightly through the grid, she swung herself upside down, holding her cap in place with one hand. She glanced up towards her friends, wordlessly inviting them to join her under the scaffold.
(oh NO!!)
A bolt of panic shot up Jessie's spine. How was she going to get out of this?! Lisa was already shifting herself into position, preparing to pitch over the side. It was all so unjust: both her friends were wearing jeans. No one was going to see their underwear. Jessie had a sudden vision of her fresh white panties, sweet and innocent and painfully feminine. It just wasn't fair!
Face blazing maraschino red, she looked out across the oval, where the football guys were still chasing the ball about the field. On the surface at least, the coast looked clear. Trouble was, Jessie knew it was a trick; they were all biding their time, waiting for the penny to drop. Every last one of them!
What was she going to do? Her dress was too short to tuck into the legs of her panties (which was what she normally did) too light to stay up of its own accord. What on Earth had she been thinking, wearing some thin, gossamer remnant to the playground when she knew they'd be playing on the jungle gym? Why hadn't she worn one of her tight denim skirts? She only had about a hundred of them. She could even have worn tights, it was certainly cold enough this late in the year.
Of course, that was all beside the point now; Jessie was swiftly running out of options. Lisa had just eased herself down through the rungs. In a few seconds, she'd be expected to follow, brief cotton sunfrock or no. She had no excuse, no way to explain her dubious behavior. It was a classic no-win situation. She simply had no other choice.
No other choice at all.
Swallowing a deep, calming breath, Jessie hooked her knees over a bar and slung down between her two friends. Her dress fell away almost immediately, flipping inside out and revealing her thighs and belly, all the way up to her tummy button. She swung back and forth with her virginal white panties flashing brightly in the late October sunshine, a rich carmine hue darkening her features.
The girls hung together in a gently undulating row, their long hair streaming toward the turf. Three little bats in a belfry, quiet as church mice. Jessie's dress was creeping inexorably toward the ground, inverting gradually over her neck and shoulders. Her heart skipped a beat; several, in fact: she was presenting far more panty to the world than she had on the swing.
A brief lull in the conversation ensued. A cool breeze whipped through the park, whispering through the trees like an Autumn wave. Jessie shivered momentarily, feeling a delicious rush of gooseflesh cover her belly. Her dress had slipped down so far it was practically dropping off her body. Her smooth, ivory torso was on open exhibition, all the way down to her slim white throat.
"That dress is about to fall off," Debbie suddenly warned, tugging gently on Jessie's hemline, "then you'll have to walk home in your underwear."
"No, I won't," Jessie replied with a roll of her eyes, although the idea made her pulse hurtle into overdrive, "if it falls off, I'll just put it straight back on."
"If it falls off, those boys will come over and throw it up in a tree," Debbie corrected, gesturing towards the oval.
"No, they won't," Jessie answered, "I'd be down off here so fast, they wouldn't get the chance."
Her dress was now hanging completely over her face. She held the hem out of the way with her right hand, fighting a losing battle against both gravity and centrifugal force.
"Bet you they would," Debbie challenged. A mischievous smile touched her lips.
"Bet you they wouldn't," Jess answered.
"Would!"
"Wouldn't!"
"WOULD!!"
"WOULDN'T!!"
"OK, then - let's see."
Moving faster than Jessie could react, Debra took hold of her dress and yanked it down with both hands. Holding on by no more than a promise in the first place, the frock peeled off without the slightest resistance. Jessie's eyes widened to the size of dinner plates, she gaped in open-mouthed shock. Her dress had vanished like a soap bubble, leaving her hanging upside down in nothing but her socks and panties.
Her lacy, white panties.
Jessica shrieked at the top of her lungs.