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Kayleigh's Story

Author: 

  • kayleigh01

Organizational: 

  • Title Page

Audience Rating: 

  • General Audience (pg)

It was time for Jared to take - quite literally - a good long look in the mirror. For the first time ever, he recognized that something was wrong. Eyeing his body, he realized his boy clothes just didn’t fit right - for one thing, they were baggy, not tight, and his shoes were dirty and ugly, and...

Kayleigh's Story


by
Kayleigh01

TG Themes: 

  • Fresh Start

Kayleigh's Story, Chapter 1: All The Way

Author: 

  • kayleigh01

Audience Rating: 

  • General Audience (pg)

Publication: 

  • Novel Chapter

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Real World

Permission: 

  • Posted by author(s)

Things were getting out of control. Jared could see it. The coach could see it. The 1400 souls inside Longwood’ High School’s gym could see it. The five young men on the floor couldn’t, however, and that was all that mattered.

Athens 38, Longwood 16. Athens 40, Longwood 16. Athens 43, Longwood 16. The outcome of the game was never really in doubt, as Athens had played for the state title the year before. But this was absurd. Athens 45, Longwood 16.

Student manager Jared Barnes was decidedly sad for many reasons, he thought as he scribbled another Athens 3 in the scorebook (48-16, Athens). Firstly, he was sad for his friends on the team. Fellow freshmen Dan Smith, the scrappy little point guard, and Nick Wilkins, the power forward, were turning in what was by a decent margin their worst performance of the season.

Secondly, he was sad for himself and the other fans. Little Longwood, Michigan, was a basketball town, this season had been loaded with expectations, and now they were being shattered, first (51-16, Athens) by a mediocre regular season, and now by this final indignity at the hands of an opponent superior in every way.

Thirdly, Jared Barnes was just plain sad. This was beyond basketball, this was beyond even school, there was just a deep, dark sadness within Jared Barnes that it would be nearly impossible to cure (54-16, Athens). This loss by a quintet which he dearly loved only plunged him further into the abyss of depression he was already in.

The onset of this private hell within him had began about a month ago, after school one late January day. As was custom, his sister had ballet practice, and his dad wouldn’t be home for another several hours due to work.

Time for the sports-loving boy to do what any 14-year-old boy would do after school - that is, raid his sister’s closet. Yes, Jared, if it was possible, knew his twin Grace’s closet better then she did. He wondered how in the world she hadn’t found out that every waking hour she was out of the house her brother was tearing up her drawers attempting to find the right pantyhose to match with that majorette outfit.

There wasn’t much time to wonder, as (56-16, Athens) Jared’s dress-up time was limited. He planned nothing special for today - deciding against wearing makeup, Jared ditched his mundane wardrobe for a pink “Longwood Dance” sweatshirt and some yoga pants, and then settled into his own bed, burying himself in one of sister’s fashion magazines.

Hours passed, and Jared felt at home, when suddenly he heard the garage door open - someone was home! Luckily he’d been through this drill ten thousand times. He pulled down his leggings, squirmed out of his sweatshirt and carefully unclipped his bra. He decided to keep the red panties he was wearing, grinning madly as he pulled his boy jeans back on.

Jared looked out the window to see his dad and Grace conversing with a neighbor. Phew, Jared had thought (59-16, Athens). He was safe.

He looked down and gazed at his sister, just for a moment, but in that short timeframe analyzed every bit of her features - and compared them unfavorably with his own. He looked over her breasts, butt, and budding curves, not in a creepy way, but in a way that a sister would compare her own features with another’s. He was suddenly very aware (61-16, Athens) of what he was doing.

It was time for Jared to take - quite literally - a good long look in the mirror. For the first time ever, he recognized that something was wrong. Eyeing his body, he realized his boy clothes just didn’t fit right - for one thing, they were baggy, not tight, and his shoes were dirty and ugly, and...

That was the moment Jared Barnes realized he was living a lie - to himself, his family, his friends, to nature, to Fate, to God, to humanity. He was lying every day he put on gym shorts or baggy jeans rather than yoga pants or a skirt. He was lying (64-16, Athens) when he dressed up for basketball games in a suit and tie and not a dress. He was lying when he went home after school rather than to cheer or ballet or something of that sort, because as much as he enjoyed lying around in sweats, he would rather be jumping around in skirts anyday.

Which is what Longwood’s cheerleaders were doing that day - raucously, even though their squad was now being battered to the tune of 66-16. Jared caught their uniforms out of the corner of his eye, and did a double take. They were just so pleasing to them - something about them, some intangible quality that made him desperate to get hold of one.

A thought popped into his head. He could do it. In fact, he could do it easily. Just 53.5 seconds...

The final was an ungodly 67-21, after a flurry of utterly meaningless points scored by reserves against reserves. A handshake line was followed by modest applause for the Longwood Wildcats, and then, a retreat to the locker room.

Coach Garrison was surprisingly succinct. “Not much you can say about that one,” he opined staring first at his chalkboard and then into space. “I will see you next year. Good afternoon.”

Grumbling, all the players retreated to their lockers, some grumpy, some optimistic, all bewildered by what they’d just witnessed. Strong, silent big man Earl Green just shook his head, trying to comprehend the thing. Dan Smith spoke with the coach, and then joined Jared and Nick Wilkins.

“That was something,” Dan astutely observed.

“Indeed,” Jared responded. “You’ll get ‘em next year.”

“Are you kidding me?” Dan shook his head, half-joking, half-dead serious. “That’s a college team. They should be playing Louisville, not Longwood.”

There was a silence. “You want to go out later?”

“Sorry, Jared. Need a few hours to swallow this crime against humanity,” Dan responded dryly. “See you tomorrow.”

Jared hurried past Nick, whose locker sat at the other end of the room, making for what appeared to be an exit, but what was really an alternate entrance to the locker room’s storage area, a heaven on earth which would contain extra cheer uniforms galore, the excited boy (using the term very loosely) calculated.

A silent slithering to the back of the locker room, a few odds and ends rearranged, an old door opened, and bam! Jared Barnes was in the little-used storage room, which he’d seen entered by another human a grand total of once, when the cheer coach needed somewhere to put surplus uniforms.

She probably hadn’t accounted for girly-gurls who may pass through, Jared chuckled to himself, as he pulled on the light in an extra-careful manner. He even had a mirror to pimp into! It was like his own little fitting room, with a horrid smell added on. Jared couldn’t help but wish a little perfume were present to alleviate the stench.

Jared stripped to his underwear, revealing his clean-shaven legs, something he’d worked hard for. While most boys his age saw leg hair as validation of manhood, he saw it as an invalidation of his natural girlhood, and worked hard to get rid of it. The legs were shiny and white and would have fit right in the cheer squad. The lump between wouldn’t have, however, and Jared actively worked to conceal it.

Five minutes later these minor impediments were distant memories, as Jared stood mesmerized at his reflection in the mirror. He probably could pass for a cheerleader without makeup, if he just combed his hair a bit, as the skirt and top fit his figure perfectly.

There was a pair of pom-poms right next to the box where he’d found the outfit. Jared picked up the pom-poms and cocked his hip, mimicking an ultra-girly pose he’d seen some of the squad members strike before the game. It was perfect. Jared was perfect.

Footsteps sounded loudly in the room bordering the storage area. Jared had not five seconds to react before the door was thrown open. Earl Green, all 6’6” of him, stood silently beholding 5’7” skinny cheerleader Jared Barnes, a boy wearing a skirt, a headband, and an apple-red facial expression.

Jared opened his mouth but no words escaped. Earl tried to speak and found the same problem.

Suddenly, more furious footsteps. Instinctively, Jared hid, shielding himself behind a cabinet. He took in the exchange of two voices, all the while breathing heavily, knowing his fate could be hanging in the balance.

“Earl, what are you doing?” A familiar voice.

“Uh-Nothing. Just saw this door open, figured I should close it.”

“You look as if you’ve seen a ghost!” Dan exclaimed. “Is someone in there?”

“Certainly not!” It was the loudest he’d ever heard Earl talk. “What is this, an interrogation? ‘Sides, don’t you have somewhere to be?”

“I suppose,” Dan responded. “Close the door on the way out, by the way. It stinks in here.”

“Got it.” Earl went to shut the door, but not without uttering seven life-changing words.

“Give me ten minutes. I’ll be back.”

He wanted to run right then, or die. One of the two. Anything to get away from this wretched place, where he was doomed to have his most precious secret revealed to the whole world.

He heard the door click and more footsteps, this time markedly softer. He saw Earl’s large frame against the storage room door, and heard a sound from that frame, the sweet sound of a friend who cared.

“Jared, come out and talk to me.”

He obliged, and Earl implored him to sit with him on the ground. Still silent, Jared was further quieted - if it were possible - by Earl’s next words.

“You look pretty.”

Pause as Jared took in the fact that his good friend Earl Green (a senior boy! What would Grace think?) had called him pretty. He had seen on the internet many a crossdresser, and had seen them be referred to as “sexy” and “beautiful.” But to be called that authentically, to his face - it meant the world to Jared. He snickered a little. “Thanks,” he added demurely.

Suddenly he was businesslike. “Well, that proves it ain’t your first time,” he declared. “If you’d have just been fooling around you’d have shot back with something smart, probably.”

The senior squatted down to face a gurl brimming with embarrassment. A short Q-and-A session ensued. “How long have you been doing this?”

“My whole life.”

“Anyone ever know?”

“Not a soul.”

“You identify as a girl?”

“Yes and no,” Jared shrugged. Earl was impressed with his answers but pressed him further.

“Look in the mirror. Are you a boy or girl?”

One look in the mirror yielded a firm answer: “A girl.”

“Just as I thought.” Earl was either the greatest detective or greatest psychologist in the world, or both. He was ten steps ahead of Jared at any time. Jared knew he was at the brainy big man’s mercy.

Earl did too. He launched into a monologue.

“I could easily leave this room and tell the whole world what I saw in here,” he announced. Jared was frightened.

He stopped pacing and spat. “But I won’t. Cause that’s wrong.”

Jared cut him off. “I owe you something. Anything.”

Earl held up a hand. “I’m about to tell you.” More silence, of the deafening variety.

“Do this for me,” Earl sighed. “Stop lying to yourself. I can’t stand liars, and you might be the worst kind, because you lie, to yourself and everyone else, by your very existence.

“I think we both know you are unhappy as a boy. Then don’t be one. You’re a natural girl. I have five sisters and none of them swish their butts as much as you did walking over here to talk to me. Go all the way, Jared Barnes.”

Earl abruptly left. Jared had a lot to think about, not the least of which was putting his boys’ clothes back on.

Jared tracked down Nick Wilkins for a ride home and immediately flopped on his bed. His sister was out of the house, practicing for a recital at a friend’s. His father was out of town, on business.

One look at the clock revealed the time to be a half hour until his sister would be home. As he pondered Earl’s words, one thought ricocheted through his skull like a broken record.

“Stop lying to yourself. Stop lying to yourself. Stop lying to yourself. Stop lying to yourself.”

“Stop lying to yourself!” Jared said the words out loud, and began repeating them, almost chanting them, some moments at a whisper, some at a near yell, over, and over.

All the while he riffled through his sister’s closet, finding a heavily padded bra, matching panties, seeking just the right outfit, finally settling on a “Love Pink” t-shirt, a pair of yoga pants, and his sister’s Ugg boots. Not terribly girly, but in no way confusable with boys clothes, especially not with his padding. He applied some makeup but decided not to fix his hair, leaving it as is except for a headband.

He sat on the steps anxiously, and seconds became minutes, minutes multiplied, until finally, his sister threw the door open and beheld her brother.

A lying boy had been replaced by a supremely honest, sweet girl. The insincere story of Jared had ended, and now a new, real, sparkly pink story could begin.

This is the tale of how Kayleigh Marie Barnes went all the way.

Kayleigh's Story, Chapter 2: Nights of Silence

Author: 

  • kayleigh01

Audience Rating: 

  • General Audience (pg)

Publication: 

  • Novel Chapter

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Fresh Start

Permission: 

  • Posted by author(s)

Five months following the events of “All The Way...”

The June night was quiet, almost seeming to gnaw at Jared as he rocked back and forth on his porch, staring out into the darkness illuminated only by his small town’s streetlights.

Grace was there with him, but remained respectfully silent, as it was clear he was thinking very hard. He was on the precipice of a life milestone, but seemed nervous. Grace stood up from her rocker, strutted over to Jared’s, and patted her brother on his back.

“It’s your last night as a boy, Jared,” she told her brother. “You should enjoy it.”

“I’ve never enjoyed being a boy, so why should I start now?” Jared had a far-off look on his face when he uttered these words.

“As soon as we get to Pittman I’m burning all these,” he continued, gesturing to his drab outfit. “They’re incredibly ugly. I’m going to the store and buy every single pair of short-shorts there is.” He resumed his dour stare into the night.

“Jared,” Grace sighed, “we should at least do something. Come on! We can do whatever you want. It’s your night.”

“Darden’s gonna be here in ten minutes!” Jared exclaimed. “Let’s just sit here and wait for him.”

Grace nodded knowingly. She could see Jared was anxious, oh-so-anxious, for a fresh start, which he would get in seven hours, when the Barnes family, Dad, Grace, and Jared, skipped town in the middle of the night, crisscrossing the state in the wee hours of the morning, where a father, a daughter, and son would get a fresh start as a father and two daughters, far from the town they knew and loved but knew they had to leave behind.

For Dad, it meant a new job in the field he dearly loved. For Jared, it meant a new life in the gender he so adored. And Grace - well, Grace would be there as well, supportive of her soon-to-be new sister every step of the way.

“Well, I do have something planned, after we help Darden load the boxes,” Grace finished. Mr. Darden, a longtime friend of Mr. Barnes’, was in on the “plan” and was going to help with the moving process, as well as explaining to the Longwood townsfolk the family’s sudden departure.

Silence again, and Grace looked her brother over. It suddenly dawned on her that everything she took for granted about being a girl, things that she did every day - applying makeup, fixing her hair, trying on dresses - Jared was longing to be able to do, and psyched out of his mind to be able to do, when finally given a chance.

Grace couldn’t help but smile. She remembered the first time Jared had greeted her at the front door in her clothes. Her jaw dropped, and, admittedly, she was caught off guard. But she embraced it, and was there for her brother/sister from the moment Jared decided this was something he wanted.

Looking ahead to Pittman, her excitement only increased. A twin sister to laugh with, cry with, dance with, and - hopefully - double date with. She was overcome with joy. Out of nowhere, she started to cry.

“What’s wrong?” Jared’s face turned on a dime from apathy to sympathy. He was clearly very concerned for his twin sister. Grace saw this, and saw the sincere look of concern on her brother’s face, and was again overcome, only descending further into tears.

In between sobs, Grace recounted her train of thought to Jared, and soon they were both crying. Jared had been thinking of laughing with, and crying with, dancing with, and double dating with his sister for so long - and now, here he was. His attitude changed from somber and reflective to joyous.

“I can’t wait to double date with you!” Jared whispered after their joint crying jag had subsided. “Maybe we can wear matching outfits! We’ll have to go dress shopping as soon as possible.”

Jared and Grace just smiled, at peace with themselves and one another. No more anxious silence - the kind of silence that filled the muggy evening was anticipatory and hopeful.

A black car crawled slowly into the driveway, obscuring the moving van that had already been parked at the Barnes household earlier that night. A door slammed, and the tall, friendly figure of Mr. Brian Darden appeared on the porch, greeting Jared and Grace.

“Evening, Grace. Evening, Jared,” he said warmly. “Your father told me there’s some more boxes in the living room?”

“I’ll get them,” Grace announced. She motioned Darden into the living room and signaled for Jared to stay put.

Jared grinned as he sat on the porch, still looking out into the night, and still longing, now more than ever, for a taste of girlhood. To know it was so close - that he was on the cusp of a new life, in a new city, with new friends, in a new body - was mind-bending. He drifted away, filled with dreams, of the teenage girlhood that had long eluded him but was now so close...

He was awakened shortly thereafter by talking - it was Jared’s father, Mr. Barnes. It was now eleven o’clock, and Jared realized his family would be leaving soon. He left the porch and conversed with his father and Darden briefly, before helping to load the last of the boxes into the van and Darden’s car, the two participants in the convoy that shortly before midnight would set off into the cool Midwestern night.

Suddenly a voice - Grace’s - cried out from the front door. “Jared! Come here!”

Curious, Jared followed his sister into her empty room. She beckoned Jared to her closet, gestured toward a cardboard box, and implored Jared to open it.

Fifteen minutes later, Jared and Grace Barnes were standing side by side, in matching black dresses obscuring the top parts of clean-shaven legs, wearing black headbands and high heels and giggling uncontrollably.

“I look silly!” Jared snickered. “I can’t wait to grow my hair out! And hopefully I can start the transitioning process right away!” He looked down at his chest. “These rolled up panties just aren’t doing much for me.”

A knock sounded on the bedroom door. “Girls! Can I come in?”

Grace opened the door and saw her father’s mouth fall open. Mr. Barnes was stunned, and as he looked upon his son dressed impeccably as a pretty girl, he began to cry.

“Jared, you look so beautiful,” he sniffed. A group hug ensued, and in the midst of the cryfest, Jared’s father shoved a piece of paper into his hands.

“Read it,” he implored his son.

The old note, in impeccable handwriting, read:

May 15th, 2001 - Names Decided!

For boys, it’s Jared Anderson and Brian Nicholas! For girls, it’s Grace Anne and Kayleigh Marie! More excited than ever!

“This is for you, Kayleigh,” Mr. Barnes said, welling up.

Kayleigh almost collapsed, she was in such an emotional state. Mrs. Barnes had died shortly before the twins’ first birthday, and their father had raised a son and a daughter alone. Little did he know he was just getting started, as now he would raise two, twin teenage daughters. Mr. Barnes was apprehensive but ready.

After weeping, as Mr. Barnes gushed over how proud his wife would have been of her two daughters, it was time to go. And after saying goodbye into the house in which she grew up, Kayleigh Barnes strapped herself into the moving van and prepared to grow up again.

It was just Kayleigh and Mr. Barnes in the moving van, as Grace had opted to ride with Mr. Darden. Both cars wound carefully through the country roads, finally reaching the highway as a half-hour of their five-hour journey lapsed.

It was quiet. Neither Mr. Barnes nor his daughter spoke for a while. Kayleigh looked at the window at all the familiar sights she may never see again, and fingered at her dress, reflective all the while.

“You know I’m proud of you, Kayleigh.”

She turned her head. Her father continued.

“I mean, you were so brave - and you’ve been so brave through the whole thing, having the guts to be your true self. Few people in this lifetime - have your courage. Be proud of yourself.”

Kayleigh gulped. She was literally starting over and there was no turning back. She was going to be a girl. She had left all her old friends behind, cutting off contact with people such as Dan and Nick and Earl - Earl, who had set her on the journey she was now undertaking. This was a new frontier.

“I can’t wait,” she said out loud.

“Neither can I,” Kayleigh’s father said. “Neither can I.” He admired his courageous daughter as she drifted off into a peaceful sleep.

---

The sun peeked over the horizon as Kayleigh stirred. It was the first thing she saw as she looked out the window, into a new town a world away from her old one. Tucked in Northern Michigan, it was an idyllic setting for the raising of a young woman such as herself. Half-asleep, Kayleigh mustered a smile.

The van rolled into the driveway of their new house, where Darden and Grace were already unpacking. Kayleigh hopped out of the car, hugged her sister, and inspected her new residence.

“It’s beautiful,” she said to Grace, as she helped her unload her clothes in her room.

“It really is,” Grace agreed, as she stared in unbelief at the homely arrangement of the three bedrooms, as well as the pretty entryway. After hanging up some of her clothes, she called Kayleigh into her room.

“We should go shopping tonight!” Grace exclaimed.

“Already? It’s our first night in town!”

“Yeah, but you need some clothes! We can’t keep sharing!”

“Daddy says we’ll have a whole week dedicated to shopping as soon as we get settled in, and I get fitted for a wig,” Kayleigh said matter-of-factly. “I’m not going out until then.”

“Come on, we’ll just walk to a thrift shop or something. I’ll put a headband in your hair and I’ll drench you in makeup. It’ll be fun!”

Kayleigh thought for a minute, but not that long. After some convincing of Mr. Barnes and a lot of unpacking, the sisters were on their way. It was a short walk to Anna’s Goods, and the weather was unseasonably cool. Both girls wore leggings with sweatshirts, Grace blue and Kayleigh pink. Kayleigh’s hair was done in a girly style and featured a headband, and she wore a relatively large amount of makeup.

“Are you sure I don’t look like a boy?” Kayleigh asked for the umpteenth time as they neared their destination.

“No, no, and no again!” Grace was indignant. “For heaven’s sakes, Kayleigh Marie. You are girlier than me!”

“Yeah, yeah.” Kayleigh wasn’t reassured, and continued muttering, all the way to the store. Once in there, Grace was incensed.

“Will you stop whining?” Grace nearly shouted, stopping as the girls approached the dress section.

“What?”

“You are not a boy, so why don’t you just drop the subject! Okay?”

Kayleigh was speechless, deep in thought, when she made a plea both to herself, to Grace, and to the world simultaneously.

“Prove it.”

Grace was unsure of what to make of her sister’s comment - for but a moment. Looking at the rack of dresses, she pulled one down. It was something a bridesmaid would wear, a romantic looking gown with a tulle skirt and sequined bodice.

“Go buy this.”

Kayleigh eyed the dress. “This?”

“If the cashier thinks you’re a real girl - which you are - she won’t bat an eye.”

Kayleigh clutched the dress nervously, and sauntered over to the cashier. Eavesdropping intently, Grace heard nothing but silence. When she came back, she was crying.

“What is it, Kayleigh?”

“She didn’t say a word!” Kayleigh was sobbing. “I am a girl, aren’t I?”

“Yes, you are,” Grace said. And as her pretty twin sister zipped herself into the dress, she couldn’t help but think that with a new hairdo and some curves - real or fake - Kayleigh might be the most popular girl in school.

But she remained silent.

Kayleigh's Story, Chapter 3: Welcome to Her World

Author: 

  • kayleigh01

Audience Rating: 

  • General Audience (pg)

Publication: 

  • Novel Chapter

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Fresh Start

Permission: 

  • Posted by author(s)

Four months following the events of “Nights of Silence...”

The bell rang, once softly, and then louder, bringing down the curtain on another day in the life of the most popular girl at Pittman High School.

Kayleigh was more than ready to go home, after taking care of a few things. She was worn out and cranky, just wanting to take a nap, like any other teenage girl.

Jenna, a girlfriend of Kayleigh’s, met her at her English class desk.

“Ready to go, Kay?”

“Just a minute.” She riffled frantically through her purse, searching for pink lipstick.

“Again, Kayleigh? Come on!”

“It’ll take one second!”

About two minutes later Kayleigh left the classroom with Jenna trailing behind. She swished her butt as she put one Ugg-boot-covered foot in front of the other. “Walking girly” almost came naturally to her now.

She had blond hair, long and wavy, all hers, with no extensions whatsoever. She’d pierced her ears and, as evidenced by her frequent digging into her purse, she wore a lot of makeup.

She wore a frayed, denim jacket over a white tube top, complementing denim jeans. The outfit came tantalizingly close to revealing her belly, but didn’t, much to many a boy’s disappointment.

Kayleigh still expressed shock, often, of how well she’d fit in. She had three guesses as to how she’d risen on the social ladder of the small school, and has she trudged to her locker, she ruminated about them in decreasing order of probability.

First was the simple explanation. Shortly after arriving in their new town, Kayleigh and Grace had started into ballet lessons at the Pittman Dance Academy. Kayleigh had risen incredibly quickly and wound up nearly on Grace’s level. There, they hit it off with three other ballerinas - the aforementioned Jenna, as well as Emma and Breanna. They’d become fast friends, and when it was brought to light Jenna, Emma, and Breanna were the three most popular girls in school, it was only natural the Barnes girls joined their small clique.

Second was the fact that, because Kayleigh and Grace were pretty outgoing, they’d slid in to the popular lunch table fairly quickly.

And the third could be summed up in one word: hormones. Kayleigh had always, for whatever reason, preferred this explanation to all others.

The fact is, when Kayleigh started onto small doses of estrogen, she’d basically become a stereotype of a girl - mood swings, crying and laughing jags, boy-craziness. And, although they were moving at what the doctor described as a “glacial” pace, she was gradually getting boobs and a butt as well. When she removed the pads she hid under her bra and panties, she could actually see, beyond the padding, an inkling of little boobies just starting to bloom.

Angered when the doctor had told her how abnormally slow her breasts were growing, when she had a chance to shop online for padding, she’d chosen the biggest pads she could find. So it went without saying that Kayleigh had the biggest bust and butt of any of her friends by far. And that, perhaps more than anything else, will make you popular in high school.

Kayleigh arrived at her locker and threw herself dramatically against it, venting to her twin sister all the while.

“I’m SO tired,” she mustered all while muttering obscenities. “I wanna go home and sleep, and get out of these jeans.”

“Why did you even wear those jeans?” Grace asked, incredulous. “Your yoga pants were clean, they’d go fine with your top and jacket.”

“I know, but...” Here a blush and giggle crossed Kayleigh’s face. “I caught Dean Bassett checking me out in these jeans about three weeks ago, and I thought if I maybe I wore them, he might...”

“Dean Bassett the senior? Dean Bassett the baseball star who is dating cheer captain Kirstie Hayes?”

“I suppose you’re right,” she sighed, thumbing through the waves in her hair. “I guess we’d better head home now.”

“Home? Didn’t you forget?” Emma and Breanna had now joined the trio and the latter spoke.

“What?”

“We got ballet this afternoon, remember?”

“You’re kidding me!” Kayleigh yelled, and punched her locker several times - only stopping to smile at a boy looking her over.

“I don’t know how you forgot, Miss Clay reminded us about twenty times last week,” said Emma matter-of-factly.

“I’ve never listened to anything that idiot says and I won’t start now,” Kayleigh sniped as she hiked up her jeans to accentuate her curves. “Why can’t Miss Melnik teach us all the time? I can’t understand it.”

The group split up briefly as the Barnes twins went to run an errand. “What is it with you and Miss Clay anyway?” Grace asked, confrontationally.

“She’s always criticizing me. Can’t stand it, is all.”

“Well, if you spent more time practicing and less time twirling randomly around in the tutu from your last recital she’d have more kind words for you.”

“Shut up! What would you have done if you’d never even gotten to wear a tutu before?”

“Never my ass! You told me yourself you would sneak into my room and try on all my recital costumes, sometimes in one day!”

Kayleigh tried to grasp a comeback but quickly resigned. “Yeah, I guess you’re right.” Both she and Grace giggled.

Suddenly there was a great commotion coming from above the twins, on the tiny second floor of the school. Against Grace’s wishes, Kayleigh went to check out what was going on, climbing the staircase to the upper level while Grace stayed below and spoke with a teacher.

At the end of the hall, two short freshmen - Kayleigh recognized them from what some of her guy friends derisively labeled the “geek” table - stood over a stack of books that had fallen all over the hall. They’d been carrying them on a cart, headed toward the library, and apparently had taken the turn wrong.

She picked up a few books and handed them to one of the freshmen, a bespectacled boy about half Kayleigh’s size. “Believe these are yours?” she said.

The boy said nothing, content just to stare at Kayleigh’s chest. Normally put off by this, she just laughed. The other boy was more conversational and appreciative.

“Thanks, Kayleigh. That’s real nice of you.” Everyone, somehow, knew everyone in this small school.

“Anytime,” she responded politely.

Finally, the first boy spoke, blurting out, “You’re a lot hotter than your sister!”

His friend scolded him while Kayleigh chuckled. “That’s the best compliment I can get!” She left laughing but deep down made a mental note to tell Grace, knowing it’d tick her off.

She thought little regarding the fine deed she’d just done. Because take away the girly clothes, the hair and makeup, the bra, the panties, and the real and fake boobs and curves, and you still had Jared Barnes, who thanks to Earl Green’s spontaneous kind gesture was able to receive a fresh start...

---

“What time’s Daddy picking us up?” Kayleigh asked Grace when all five of the girls were together again.

“Fifteen minutes,” Grace responded, thumbing through her phone.

“Good, I’ll be right back.” Kayleigh had one more errand to run - and it was an important one.

Just because she was wearing skirts and tights didn’t mean Kayleigh didn’t have designs on pursuing her favorite hobby - managing her school’s basketball team. And Pittman, according to the papers, had a young one that had the potential to contend. To Kayleigh, potentially being a manager was a can’t miss. She only hoped the coach/athletic director/teacher Mr. Hull would agree.

Kayleigh slunk into Coach Hull’s office and slumped into a chair. A boy, who Kayleigh barely looked at, was waiting outside as well. Speaking from the room told the pair the coach was in a meeting.

Almost unconsciously, she pulled lip balm from her purse and layered it yet again. She inspected herself carefully, using her phone as a mirror, and then smiled, satisfied.

“You’re getting awfully dolled up for a meeting with Coach Hull.”

The boy was buried in a notebook, writing something down, not looking up at Kayleigh as he spoke those words.

“And you would be?” Kayleigh was most annoyed.

“Connor Cox, sports editor, Pittman Trumpet. Here to interview the Coach,” he said politely. Kayleigh found him a bit pompous. “You’re Kayleigh Barnes, right?”

“I am,” she said, tossing her hair. “What’s it to you?”

“Nothing, nothing,” he said. “It’s just that, I was wondering if you could help me.”

“With what?” Kayleigh raised an eyebrow, suspicious, but interested - especially now that she’d seen Connor’s face.

“Well, you see, I’m the sports editor. And since the ballet is so prominent around this area, we’ve always covered them in the sports section, kind of lumping it in with the arts. And the girl I used to talk to about ballet, Lydia Bowdry, graduated last year. So I kind of need a new contact. Would you be willing to come talk to me now and again, about what’s going on at the academy?”

Kayleigh eyed Connor seriously but soon giggled. “You talk too much,” she laughed.

“Oh, sorry about that. Unusual for me.” Connor blushed and Kayleigh laughed harder. They both smiled.

“I’ll do it. Here,” Kayleigh said, “why don’t you text me?” She scribbled her number down on his notepad. She had never done that for any boy before, but she didn’t tell Connor that.

“Alright, I’ll text you, Kayleigh. Thanks!”

The five seconds they smiled at each other felt like an eternity - an eternity interrupted by Coach Hull’s throwing open the door.

“Alright, who’s going first?” The coach seemed irritable.

“I’ll go,” Kayleigh said, taking charge. She sat in a chair, crossed her legs, folded her arms, and prepared to turn on what she called her “princess charm.”

“So what can I do for you, Miss Barnes?” Coach Hull asked detachedly.

“Well,” Kayleigh said in a high-pitched voice, one that she only used when kissing up to adults. “I was wondering I could be of any assistance to the basketball team.”

“Kayleigh, Kayleigh, Kayleigh,” the Coach sighed, shaking his head. “I think you’ve made a mistake. If you’re interested in cheer talk to Mrs. Berkeley.”

Only mildly offended by Coach’s presumption, Kayleigh continued. “No, no, no!” she stated. “I want to help out as a manager, with the boys’ basketball team.”

Coach Hull pushed his glasses upon his old face and breathed carefully. “You, Kayleigh Barnes, want to be a manager with the boys’ basketball team?”

“Yes,” Kayleigh nodded.

“And how,” Coach Hull said as he paced anxiously behind his desk, “do I know that you won’t just use the position to talk to boys?”

Now Kayleigh was fully offended. “Excuse me?”

“Come on, Miss Barnes,” Coach Hull said snidely, shaking his head and grinning simultaneously. “You’re in my gym class. I’ve had to silence you several times because you’re constantly flirting! And how do I know you won’t do that when you help me out?”

“Coach Hull, that is...” Kayleigh just shook her own head. “I know basketball and I know I’ll do a good job. Please. Just give me a chance.”

“Lemme think about it.” Coach resumed his detachment.

Kayleigh stood up, straightened her jacket, hiked up her jeans, and fingered her hair. Her eyes were drawn to photos on Coach’s wall.

“Is that Bob Lanier?” she asked, referring to the Detroit Pistons great.

Coach stopped, and smiled a wry smile. “I knew I’d regret not letting you do this than vice versa, Kayleigh. Sorry I questioned you. Tryouts are Monday and you’re free to join us.”

“Thanks, Coach,” Kayleigh said. “See you then.”

A handshake and they parted.

Connor was still outside. “How’d it go?” The boy piped up.

“Well, Coach is a nice guy when he’s not being a bit of a sexist,” Kayleigh proclaimed.

“Ah, I see,” Connor chuckled. “Well, I guess I’ll see you around.”

“Not if I see you first!” Kayleigh needled him. She turned, made an effort to shake her butt, and left.

Connor thought for a minute, shrugged, and went back to his writing, thinking little of his run-in with the Most Popular Girl in School.

Kayleigh did the exact opposite. She’d seen something she liked in Connor - something more than the “Crushes-of-the-Month” as Grace derisively labeled the Dean Bassetts of the world. She grinned ear-to-ear as she met her girlfriends in the bathroom as they changed into their leotards.

“What are you smiling about, Kayleigh?” Grace piped up.

Kayleigh gulped. “The geeks think I’m hotter than you!” She announced, as she wove her hair into a pretty bun.

Laughter echoed through the bathroom, audible in the hallways of the school that Kayleigh Barnes had taken and made her own. This was Kayleigh’s world. The whole wide world. A girl’s world. At last.

Kayleigh's Story, Chapter 4: Best Laid Plans

Author: 

  • kayleigh01

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Novel Chapter

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

Permission: 

  • Posted by author(s)

Kayleigh still had the smile from her encounter with Connor pasted on her face as she crowded into her father’s car with her girlfriends, who bristled as she described her meeting with Coach Hull.

“I can’t believe he thought you were doing it to meet boys!” Breanna shrieked. “That’s so mean. What a sexist.”

“I mean,” Kayleigh giggled. “He wasn’t entirely wrong.”

The girls chuckled. “Did you manage the basketball team at your old school?” Jenna asked.

“Yeah, I did!” Kayleigh beamed. “But that was different...” She trailed off.

“How was it different?”

“It’s a long story,” Kayleigh shrugged, eager to change the subject. “Can you help me with my bun?”

“Sure.”

Anxious to reaffirm her girlhood, Kayleigh asked Jenna if she knew Connor Cox.

“Yeah! Nice guy, a little weird, kind of cute, keeps to himself. Why? You interested in him?”

“No, I just met him outside Coach’s office. Just curious, is all.”

“Yeah, curious.” Jenna giggled, knowing her girlfriend’s ways.

“Who’s this Connor?” Mr. Barnes piped up from the front of the car.

“Daaaaaaddddd,” Kayleigh whined as all the girls howled.

“Just asking, just asking!” he chuckled as he resumed his driving.

The car full of leotard- and tights-clad teenage girls was filled with chatter, as Grace debated what purse to buy, Jenna continually quizzed Kayleigh about boys, and Breanna and Emma whispered in low voices about - something. What were they up to?

“Emma, Bree, whatcha girls talking about?” Kayleigh loudly interrupted Jenna.

“Well...” Emma started. “Since you three are our best friends in the whole world...”

“We thought you should be the first of the forty people we invite every year..” Breanna continued.

“To our big Halloween party!”

All the girls were ecstatic.

“Daddy, can we go shopping after ballet class?” Kayleigh asked. There was a costume store near the studio where the girls took lessons.

“I suppose. Have fun.” He paused. “Wait a second, Emma, come here.”

Kayleigh and Grace paused on the sidewalk in front of the studio, cocking their hips in identical poses. What did their father want?

Emma motioned for the twins and ran to catch up with Jenna and Breanna. Mr. Barnes was left alone with his two daughters.

“What is it, Daddy?” Kayleigh asked.

“Look, there’s going to be boys at this party. Grace, you have to take care of your sister. Do you hear me?”

“Daddy!” Kayleigh whimpered. “I’m a big girl! I don’t need to be babysat!”

“I know, and I trust you,” Mr. Barnes assured his daughter, running a hand down her cheek. “But it’s just-” Mr. Barnes gestured haphazardly toward Kayleigh’s chest and crotch. “Let’s just say I don’t trust boys, alright?”

“I see,” Kayleigh grumbled, only half-agreeing with her father.

“Good, good,” Mr. Barnes smiled. “Now, I know the party is ten days away, and you have to head in and stretch soon, but I want to set two ground rules right now.

“First, Grace, I want you in the same room as your sister at all times. At least make an effort to keep an eye on her. More than anything, make sure she’s safe.

“Second, costumes.” Mr. Barnes stood up and gestured at his knee. “No skirts above here. Understood?”

“Yes,” the girls mumbled.

“I love you two. Go dance.” He kissed his daughters on the cheek and departed.

“Damn it!” Kayleigh shrieked as she held the studio door open for her sister. “That means no tutu!”

Grace laughed. “You probably still could wear leggings or tights. Daddy didn’t say anything about that.”

“Yeah, but...” Kayleigh faltered. “I kinda wanted to show some skin.” She fiddled a bit with her footless tights. “I have nice legs now, and, well,” she continued her strange monologue. “I don’t know.”

Something was eating at Kayleigh, but she wasn’t sure what. It bugged her all throughout her lesson and continued as she pulled on her jeans afterwards. What was it?

“Y’all ready?” Kayleigh asked, stepping out of her changing stall still in her leotard, but wearing it with jeans and Ugg boots. She’d let her hair down and retouched her makeup when she had a moment.

“Daaammmmmmmnnnnnn!” She heard Breanna cry. “When did you get so...hot?”

“Aw, come on!” Kayleigh blushed at the compliment from her girlfriend.

“No, really!” She looked Kayleigh over and smiled. “I thought you were pretty when I met you, but now - you look like a model!”

Kayleigh faced herself in the mirror and realized exactly what was bothering her - as she saw her boobs and curves fit against her leotard and jeans, she realized what got under her skin the most from her little chat with her father.

The girls walked en masse to the costume shop nearby and split off, Kayleigh and Emma going one way and Jenna, Breanna, and Grace scouring the other portion of the store. The two girls soon found themselves in the princess section. Emma’s eyes were drawn to a Belle dress.

“Oh! Beauty and the Beast was my favorite movie growing up!” she exclaimed. Her smile turned to a frown when she held up her dress. “It’s - pretty, but not my style. I want something short, like a tutu dress. It should show off my legs a little bit.”

“Have you ever kissed a boy?”

Emma dropped the dress in surprise. “Come again?”

“I’m just curious,” Kayleigh shrugged in her familiar manner.

“Well, if you must know, I have,” Emma said confidently, putting her hands on her yoga-pants covered hips. “I’ve kissed two boys. In fact, both of them were at my Halloween parties.”

“See, that just pisses me off.” Kayleigh kicked the rack of dresses in disgust.

“What is it?”

“My dad says I can’t wear a short skirt to the party,” Kayleigh seethed. “And it bothers me.”

“Why? That’s pretty reasonable.”

“Yeah, but...” Kayleigh wanted to say how she felt like her father was trying to keep her still somewhat of a boy, by preventing her from spending time with boys, and a bunch of other complicated teenage girl stuff made even more complicated by the fact that she was hiding a massive secret from the best friends she’d ever had.

But, of course, she kept quiet.

“I don’t know. I don’t know.” She was drawn to an Elsa costume on one of the shelves. Kayleigh had always loved Frozen, dating back to her Jared days. She’d used to prance around the house in a sky blue leotard and tutu belting out “Let it Go.” Things had been simpler then.

Now she was wearing actual leotards to actual ballet classes and thinking about kissing actual boys. How times had changed. Kayleigh regretted nothing, though.

She tried on the Elsa costume in the changing room - it was different than the costumes she usually saw, which she liked. Instead of the usual dress, it was more of a tutu dress, with a sequined bodice and a tulle skirt that poofed outward at the waist and fell just below her knees.

“It’s nice!” Kayleigh smiled. She could learn to live with it, even if it was a bit longer than her liking. She’d compensate by wearing a lot of makeup. No harm, no foul.

Kayleigh paid for her costume and the girls departed. After all her friends were dropped off, and the Barnes clan had rode home, she modeled her costume for her father and sister. Mr. Barnes nodded approvingly. “Now that’s a pretty costume!”

“So cute,” Grace agreed. “Are you planning on wearing tights with it...” And so the girly-girl detail-obsessions began.

A few hours later, after Kayleigh had matched the dress with every possible accessory from tiaras to tights, she stripped down to her bra and panties and decided to take a bubble bath. She was about ready to step into the tub when she heard her sister’s voice.

“Kayleigh! Come here!”

She rushed into Grace’s bedroom in nothing but her skivvies.

“I didn’t know you had it in you, Kayleigh. You’re sneakier than me!”

“What do you mean?” Kayleigh was confused. And cold.

“Buying a costume with two skirts, one long and long short, so you could change on a dime! Sneaky!”

“I still don’t understand.”

“Here, let me show you.” Grace slipped on the Elsa dress and gave a little twirl.

“Okay, so the skirt is twirly, got that. What’s your point?”

Grace fiddled with the elastic, undid a few buttons, and revealed the full skirt was concealing a much shorter but equally fluffy tutu-style skirt underneath.

“Oh my gosh! I had no idea!”

Kayleigh almost tackled Grace, she wanted to put on the costume so bad. When she did she marveled at her body.

“Okay, princess,” laughed Grace. “You’re really gonna wear that short tutu to the party? Half your ass is showing!”

“Nah,” Kayleigh relented, thinking more and more how immodest it made her look. “I think I’m gonna stick with this.” She gestured to the full skirt.

“Suit yourself.” Grace left Kayleigh, who thought long and hard about life before falling into a dreamless sleep.

---

Ten days passed. Kayleigh’s excitement only increased. She could only flirt with boys so much in school. She could do whatever she wanted with them outside of it.

As she got dressed for school on Halloween - which, thankfully, fell on a Friday - Kayleigh kept wondering how she could circumvent her sister, who she knew would undoubtedly be watching her every move.

She knew Grace, despite her tendencies to “bend the rules,” deeply cared about her. So it would take a lot for Kayleigh to achieve her goal of being alone with a boy.

She wanted to get boys’ motors revving hours in advance, so she chose the shortest shorts allowed under the dress code, even though it was 30 degrees. She wore a tight tank top and let her hair down and made sure as much skin was visible as possible. Snowflakes fell outside her bedroom window as she did this.

“Kayleigh Marie, are you freaking kidding me?” Grace burst out laughing as she entered her sister’s bedroom dressed in jeggings, Ugg boots, and about five different coats.

“I thought you hated the cold.”

“Come on, it ain’t that cold. We’re northerners, for god’s sake.” Kayleigh made use of Jared’s old sense of humor for a moment, at which her sister smiled.

“I know what this is about, and I’ve been meaning to talk to you about it.” Grace sat on her sister’s bed and beckoned Kayleigh to do the same.

“Emma told me you asked her about kissing a boy. She found it strange. First that a girl with your looks had never been kissed. Quickly got off of that subject.

“Second your whole tangent about skirts. She thought it was odd. I thought it was odd. Even for you.

“You are going to wear the full skirt tonight, correct?”

“Over leggings, too,” Kayleigh smiled wryly. “It isn’t that bad. I’ll go for anything frilly.”

“I know that.” Grace took a deep breath. “Okay, don’t tell Daddy about this conversation, because he’ll get mad, and he won’t understand, because it’s kind of a sister thing.”

“Cross my heart.”

“If you try to kiss a boy tonight like you told Emma you wanted to, I’m not going to stop you.”

Kayleigh’s mouth fell open. A billion emotions cycled through her brain. “But why?”

“Because I think-” Grace lowered her voice, making sure what was said next was just between the two girls. “I think Dad still can’t get his head around the fact that his only son his now his daughter who is wearing dresses and painting her nails and checking out cute boys.

“He can’t stop you from wearing dresses and that kind of thing because you love it so much. So he’s trying to keep you from, well, being a normal teenage girl.

“It’s just my theory. Please don’t get mad at Daddy or me. I’m just letting you know, I’m there for you. No matter what. You’re my sister.”

Kayleigh bawled openly, which mandated she retouch her mascara, which delayed the Barnes’ ride to school already when Mr. Barnes stared down his daughter.

“You’re wearing that to school?”

Kayleigh simply shrugged. “The cold never bothered me anyway,” she grinned.

“Go put something longer on, Elsa,” her father said warmly but still stern. Kayleigh returned wearing the tightest yoga pants possible and glaring at her father, incensed.

“See what I mean?” Grace whispered. “It’s not about the clothes. It’s about what they represent.”

Kayleigh nodded at her sister’s unexpectedly deep statement. She piled into the car and headed off to school.

An informal survey of the cute boys revealed a lot of them were coming to the party. Kayleigh was excited beyond belief. She was sure kissing was in store - and maybe more. She made sure to take breath mints throughout the day, just for practice.

Kayleigh was anxiously hurrying toward her locker, eager to bring the school day to a merciful end when, for the first time since their meeting ten days ago, she bumped head-on into Connor Cox.

“Connor! I’m so sorry,” Kayleigh gasped, helping him pick his books up. As she did so, her eyes met his for but a moment.

“Hey! You coming to the party tonight?” she asked, remembering seeing his name on a guest list.

“Thorry, I can’t,” Connor stuttered. “I have a bery, bery bad cold.” Kayleigh was suddenly very aware that his subtly handsome face had a nose as red as her party dress.

“Bethides,” he mumbled. “Partieth aren’t really my thing.”

“Okay, I’ll see you at basketball tryouts on Monday!” Connor would be there to cover the team.

“Yeth! Can’t wait!” Kayleigh caught sight of him banging his head on his locker and giggled. If her plans tonight went to hell she knew she had a backup option. Or maybe if they didn’t go to hell. Many things remained to be seen.

“Ready for tonight, sweetie!” Kayleigh whirled around to face Jenna, who already had cat’s whiskers and a headband on. She planned to wear her ballet leotard with leggings and one of Kayleigh’s black tutus, which the pair had devoted last Saturday to decorating with glitter.

“As I’ll ever be! Don’t you look hot!”

“Not nearly as hot as you,” Jenna shot back in her usual friendly manner. “Heard you plan on, tonight, well...” Jenna did an eyebrow flitting motion.

“Nah,” Kayleigh brushed her friend off. “We’ll see.” Kayleigh really had no idea what to expect.

Two hours later Kayleigh and Grace each stood in front of the latter’s mirror in only bra and panties.

“Are you ready to do this?” Grace asked, echoing Jenna’s words.

“Let’s do it!” Kayleigh was ready to burst now, with some combination of teenage angst, sexual energy, and a general enthusiasm for being a girl.

They set about taking turns doing each other’s makeup. Grace was dressing up as Tinker Bell; she had a light green leotard and tights and she’d made her own tutu, which extended past her knees. Both girls wore wearing special princess makeup they’d seen in tutorials.

Grace put on a wig, while Kayleigh braided her natural hair for her Elsa costume. Now came the moment of truth.

After readjusting her breast and butt pads, Kayleigh stepped into her leggings, and finally zipped herself into her dress. To give herself a “street” look she wore tennis shoes, and punctuated the whole outfit with a tiara. After admiring herself in the mirror, she presented herself to her father. Wanting to emphasize her girlhood, she spoke in a cutesie voice.

“Hey, Daddy! Don’t I look like a princess?”

“You look very pretty, sweetie. Now, you and your sister remember my rules?”

“Yes, Daddy!” Kayleigh exclaimed exasperatedly. When her dad had turned, she grinned devilishly. No, Daddy. Screw your rules. She was a big girl. She didn’t need her Daddy to protect her.

She and Grace were the first to arrive, joining Emma, dressed cutely as Belle in a costume similar to the twins’.

“Here, help me get some stuff out of my room,” Emma said as she waved the girls upstairs. “I’m behind on my decorating and need a ton of help.”

Kayleigh and Grace skipped upstairs and set to work moving boxes frantically around, helping to hang decorations and set up food tables.

When Kayleigh bounded upstairs to grab the last box, she couldn’t help but look around Emma’s room. There was no room she loved being in more than a girl’s bedroom. It was a belief that had been nurtured by years of standing inside them in boy's’ clothes, just marvelling at all the endless possibilities that could be held within, in terms of clothes, makeup, dolls, you name it.

The first time the girls had gone over to Emma’s house, after they’d already become fast friends at ballet class, she’d given the girls one instruction.

“This is something I tell only my closest girlfriends,” she had said that hot day in late August. “I’ve only ever told Jenna and Breanna and this. I call it my ‘Standing Order.’

“If you’re ever sad, or ever uncomfortable, or just in need of somewhere safe, you come in my room. And whether I’m here or not, you feel free to paint your nails or try on any outfit or whatever. Understand?”

Kayleigh and Grace had nodded, just as they found themselves nodding now when Emma asked if they were sure they didn’t need anything to eat.

“Alright. I gave you first choice. You’re going to have to wait in line now, though, because it’s party time!”

Emma opened the door and all of the girls’ friends came trickling in. Virtually every notable sophomore was there, and some notable freshmen, along with select juniors and seniors the girls knew. Kayleigh put names to faces: Joe Hammond... Callie Stewart... Shelby Dunbar... Kirk Doyle... they all blurred together after awhile.

The first boy Kayleigh tried to hit on was a cute baseball player named B.J. Sample, who Kayleigh had gone gaga over in English earlier in the year. She tried to goad him into brushing against her, but she just ended up annoying him. Dejected and sad, she gave up on that adventure.

She tried moves on a few other boys, flirting with them, hiking up her skirt (at which Grace scowled), being nice, teasing them, even touching a few she knew well. But nothing was going for her. Meanwhile, much to Kayleigh’s chagrin, Jenna and Emma were in massive lip-locks with Braden Sampson and Tom Powell. Lucky, she thought, as she was simultaneously revolted and fascinated by their public displays of affection.

Kayleigh grew more and more desperate as the night progressed. She wanted to have a guy. A guy that was hers. A boyfriend. And most of all, to prove wrong what she saw as her father’s subtle idea that his daughter was still somewhat of a boy.

Now Grace had a boy as she saw her sister cuddling with Henry Dowling on the sofa, looking upon each other with those eyes unique to lovers. Jenna was the only one left standing, although she seemed to be making eyes at Darius Graham as she doled out food.

Perceived peer pressure pushed against Kayleigh’s soft skin and fragile ego. She wanted something to happen. She wanted to prove she was a real girl. But to whom? The answer, she refused to admit but would later, was herself.

The desperation mounted until she made a drastic move. Kayleigh excused herself to the bathroom after another conversation with a boy went nowhere. Once in there, she ripped off the long-skirt portion of her costume and stomped on it. Then, readjusting the tutu-like skirt that remained, she slipped off her leggings and cut them with scissors into short-shorts, which barely covered her padded panties.

After this scene transpired, she sauntered over to a chair in the main room and sat smiling with her legs open. Visibly freaked out, Jenna called Kayleigh aside.

“Is something wrong? You’re acting very, very weird and it’s scaring me.”

“You girls all have guys to be with. I want one too. That’s all.” Kayleigh smiled and maintained her open-legged position.

“Well, you look just plain creepy right now. Here, I have an idea that will get you with a boy. Emma!” She called her over from her makeout session with Tom. “It’s time.”

Emma stood in front of her fireplace and gathered everyone’s attention. “Hey, everybody! Thanks for coming! Hope you’re having a good time, but I thought maybe now we could play a game!”

The throng of twenty-odd people gathered in the room nodded half-heartedly. They significantly increased their attention when Emma announced they were going to play “7 Minutes of Heaven.”

Emma held up two bowls, with boys’ names in one and girls’ names in another. Kayleigh was anxious. Her heart pounded. She trembled. The moment of truth drew near.

Suddenly, Kayleigh had a minor anxiety attack. She had had her palms on her tutu, and found that the tulle had sagged from all the sweat. In disarray, Kayleigh told Jenna she needed a moment alone.

“Take my name out of the bowl!” Kayleigh whispered loudly. “I-I can’t do this. I need to get out of here.” After frantically searching for Grace for a moment, and seeing her holding hands with Luke Masters, she sprinted upstairs.

The Standing Order. Kayleigh, anytime she felt sad, was to go into Emma’s room, and do within reason whatever she needed to make herself feel better. This was the nuclear option. She was using it.

Able to see fine, Kayleigh didn’t turn any lights on. She slunk into Emma’s walk-in closet, and stripped to just her bra and panties.

She found a little white dress that Emma often wore as a pick-me-up on bad days. It had a cute sash, a flared skirt, and it gave a relatively generous view of her breasts. Since she didn’t need to worry about anyone seeing her fake boobs, she picked it out without thinking twice.

After zipping herself into it and twirling in the closet mirror, she cracked open the door. She was extremely startled at what she saw.

Sitting on the other side of Emma’s bed, facing the front wall (as in, Kayleigh was looking at his back) was a boy. He was rather tall, muscular, and he was making nary a sound. Kayleigh was about to turn back and hide in the closet but thought better of it.

“Who the hell are you?” She asked.

The boy spoke without turning around. “I thought I was confident in myself enough to play that game, but I wasn’t. I chickened out.” He didn’t give a name and wouldn’t throughout their entire conversation.

Now he faced Kayleigh; darkness had descended outside the room and made the two unable to see one another. The boy’s silhouette was just visible. Neither bothered to turn the light on. Neither expressed a desire to do so.

“I did the same thing,” Kayleigh said, sitting on the bed, knowing the two were now facing each other. “I don’t know what it was. I just couldn’t bring myself to play the game.” It was like the two were speaking to each other’s consciences.

“I just flat-out couldn’t do it,” the boy continued to muse. “Too damn uncomfortable. That’s not me. I don’t just go around kissing girls.”

“And I don’t go around kissing guys,” the words poured out of Kayleigh’s mouth. “Hey, at least now we can be uncomfortable together.”

“That’s right.” The creases of a smile were detectable in the dark.

Kayleigh leaned across the bed and approached the silhouette. She put her hands on its shoulders, and soon she and the boy were kissing.

Kissing was just the beginning. Soon their tongues were rolling over one another, and then Kayleigh felt a zipping sound as the boy undid her dress.

“This can go,” Kayleigh concurred with the boy, and using some acrobatics she rolled out of her dress and kicked it off the bed. She successfully removed the boy’s shirt and had lost all sense of time and place as she embraced him in only her bra and panties.

This continued for some time, the two kissing and running their hands down each other’s sides, until suddenly the boy stopped. Slowly, he dislodged his tongue from Kayleigh’s mouth, and she could make out him pulling back.

“What’s wrong?”

Kayleigh looked down and could just make out the reaching of a hand. Suddenly, she saw a solitary finger poke her breast at first, and then, a hand reach out and cup the edges of the breast. Her eyes widened. She’d been found out.

Slowly, she saw the boy withdraw from her, and stand up. He moved unsteadily, and finally stammered, “I-I have to go.”

And go he did. Yes, the boy went right out Emma’s bedroom window, unlatching and slithering out all in one motion, landing on his feet, and sprinting into the moonlit October night. Paralyzed, Kayleigh waited a moment before apprehensively slipping on her dress again.

The emotion was too much. Confounded by the surrealism of what had occurred, Kayleigh tucked her bare legs into a blanket before falling fast asleep.

Chapter 5 will be released in two weeks, on February 12th, rather than next Sunday in the middle of the Super Bowl. Hope to see you all then!


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