Mathew wandered through the tall arching doorway that led into his Aunt Carol’s massive walk-in closet. She had left the house a little more than an hour ago for the airport, and he was glad to hear of it, too. He had been waiting for her to finally take the big trip she’d been talking about for months.
Each time he thought the weekend was coming, where he could be alone to wear all of the wonderful clothes he had collected over the summer, something would come up and she would have to reschedule.
But not this time. She was gone, and Mathew had the entire weekend to have a little fun of his own.
It got old fast, Mathew thought, hiding his cute little things and soft pantyhose under his jeans; he wanted to wear them under skirts and dresses. He wanted to practice his gait in high heels out on the open floor of the house, not alone at night in his room, pacing back and forth; he needed space. He tired of having to hide the fact that his entire petite little body wascompletely devoid of hair except for his eye browsers, and the brown bun on his head. He wanted to face his fear, and venture into public one hundred percent, head to toe dressed as a woman.
That was Mathew’s ultimate fantasy: to be invisible, yet seen, and accepted.
Mathew gazed at all of Aunt Carol’s expensive, and incredibly stylish clothes, and shoes neighborly arranged in the walk-in closet. He never liked to borrow his aunt’s things unless he absolutely had to, which wasn’t often because over the course of a couple months he had purchased a decent collection for himself off the internet. Plus, she was compulsive about her possessions so if needed to, like this morning, then he had to be extra mindful when perusing through her closet.
He needed a pair of her heels to borrow this morning.
Aunt Carol’s closet was full of classy items. She worked as a paralegal at some fancy law firm that Mathew could never remember the name of; so, her wardrobe consistent of sheer pantyhose, stockings, short skirts in dark blues, browns, and blacks, tons of blooms from the basic cotton to the more elegant silk, and she had a whole dresser dedicated to panties, thongs, brassieres, corsets, and bustiers; her own private lingerie store, really.
Mathew moved passed so many items he wanted to try, but he had to stay focused. What he most adored was along the back wall, where her high heel collection lined the tall case of shelves. His favorite heels she owned were a pair of black leather T-strap heels with little embroidery stitching on the rounded toes.
Mathew handled them like pretty little twins.
Aunt Carol hardly wore them, he thought, but he remembered when she did how he could not help noticing how wonderfully she moved in the heels.
Mathew remembered the first time he wore high heels…
It was just his luck that he born the way he was. It’d always been that way. Everything that was handed down to him from his brothers, or his cousins, was either two sizes too big, or down right made him look like a child in a grown ups t-shirt. He was born premature he had learned, and along the way he just never fully developed like the other boys.
Mathew stood at 5’5 tall, and that was after his growth spurt. He wore a size x-small in t-shirts, and a size 22 in pants and shorts, and his feet, like everything else on his body, were smaller than average; a size 6 in men’s footwear, but just like his aunt – a size 7 1/2 in women’s heels.
Mathew stumbled onto this feminine side of himself by accident more so than out of curiosity. And over the years it progressed into something he yearned for, satisfying the way he viewed himself both physically, and mentally.
Nothing could ever feel more liberating to him.
He’s twenty now, but was sixteen then at that time when he lived with his cousins in San Francisco around the summer of 2019.
It was a time, all of a sudden, when the new generations of young people embraced the new communities demanding representation from their own society.
Mathew was in the midst of all that, young, but unconsciously apart of a new wave of revitalized tolerance stoking the nation once again.
His cousins were hip to it, and one night they were drinking when they shouldn’t have been, and some of his cousins’ friends noticed how beautiful Mathew’s bone structure was, and how his hips had a natural feminine way about them.
Mathew would never have noticed this before.
The word they used was androgynous, and they had to explain to him what it means. And it made sense to him, he just never thought of it that way before.
Anyways, one of the girls, a cute goth girl he liked, dared him to wear some of her clothes.
“Of course,” Mathew laughed, and said, “Not gonna happen”.
But, she said, “It’s just for a prank that we want to play on one of the other girls, this stuck-up lesbian we can’t stand.”
Her friends and her wanted to bet how long it would take the drink lesbo to realize that she was talking to a man.
Mathew thought that might be funny, too. He knew which girl she was talking about, and he was buzzing pretty good and thought it would be hilarian to get her.
He said, “I’ll do it.”
And soon as Mathew said, “Yes.” The girls cheered in excitement, and didn’t waste any time rushing him upstairs to the bathroom.
A couple of their girlfriend followed them upstairs, wanting to see if this was actually going to happen, or not.
The first thing they did was ask Mathew if they could remove all of his leg hair. They had a soap that did all of the work so he didn’t have to worry about cutting himself with a razor.
What the hell, Mathew shrugged. Nothing really matter to him When he was feeling that drink anyway.
They gave him the soap, and told him to hop in the shower, and rub it all over his legs, then rinse it off. But being as drink as he was, Mathew rubbed it all over his body as if it were regular body wash, like he was taking a regular shower.
The goth girl, the main girl, walked in, and asked, “How it was going in there?” Mathew shouted back, “I’m just about to wash my face, and then I’ll be right out.”
She freaked. “Don’t’ wash your face! That’s hair remover. It’ll take your eyesbrows off.”
Mathew stopped. Thank God she said something.
In the end, after he rinsed off, and dried off, Mathew’s entire body ended up being as smooth as silk.
The girls came in to check him out. They thought it was funny, cute as hell, but funny. He didn’t mind them seeing him naked, either. The booze, he figured.
Mathew got a kick out of it too, but he felt naked-naked, like new born naked.
The hair would grow back, he told himself, but when he looked in mirror, and saw that every inch of his body, from his neck to his arm pits, his arms, his pubes, his asshole, his legs and feet, everything except for his eye browsers andhair, was gone; he actually liked it.
Mathew felt wildly exhilarated by how sensitive his skin was to everything.
Even the slight breeze rushing in from the bathroom door opening and closing as the girls handed him a few thongs and bras to try on, felt delicious against his skin.
At that moment, Mathew felt like he was all in.
He tried on the thongs until he found one that he liked and set the other ones aside.
It was a soft, lacy white thong, and he pulled the strraps up high on his hips like he’d seen models do. The front covered his small penis okay, he thought, but it started to bulge against the thin fabric by that point. The bra he chose to match the to because that’s what he thought women did. Either way, he felt amazing, and the fabrics caresed his skin with the slightest movement. It was really turning him on.
Mathew turned his back to the mirror, and felt himself blush that he actually had a pretty cute looking butt.
Right then, atthat moment, something awakened deep down inside of Mathew, and he was instantly hooked on women’s underwear.
The girls knocked on the door, and begged to see what he looked like in the thong. Mathew had no shame in showing them. They smiled and giggled to each other, adoring how cute his plump little chefs looked in the thong. They complimented his smooth skin, his flat stromach, and legs.
“He’s a natural,” they said.
And they almost seemed jealous, thought Mathew, but how could that be?
The girls hurried him into the bedroom, and closed the door.
There were five girls in the room now, digging through the closet for something for him to wear, something to highlight his natural features, they had told him.
They showed him a few skirts, and Mathew said, “I’d wear all of them, if I could.”
He was into it, big time. But the girls wanted to see which one would look the cute.
After a dress or two, and a few tight skirts, it turned out thatThe one Mathew liked the most was the simplest. It was a navy-blue pleated skirt that was short, and showed a lot of Mathew’s long legs.
The girls grinned to each other, and quickly caught onto his style.
“He likes the school girl look,” one of them giggled. “How cute. I have just the thing, too.”
They held out a tight white t-shirt to tuck into the skirt, and pair of black thigh high socks.
It was true. Mathew was very much into anime, and the idea of dressing up like a Japanese schoolgirl thrilled him.
After that it was simple. The girls sat him down. One of them helped slide the black thigh high socks over his legs, rolling them all the way to up his mid-thighs.
For his small feet, one of the girls suggested a pair of T-strap heels like the one’s in the movie Sucker Punch. Mathew agreed at once. They fit perfect, and looked adorable thought Mathew, who suddenly felt his cock bunching up against the panties.
The girl who helped with the shoesFelt it poke her. She giggled, and whispered to the others. But they said don’t say anything. They didn’t want to ruin the fun. They knew Mathew was enjoying himself, and was losing lost sight of why they were doing this in the first place. It was for a joke, but for Mathew it was getting real, real fast.
Mathew’s hair was not long enough for the style he had envisioned, but it did have enough length to bow-clip a side-part in place, and let the hair sweep across his browser and give him the sense of having bangs.
The girls then worked together like a team of salon girls, curling his lashes, applying mascara, and lipstick, dabbing powder on his nose and cheeses, and touching him up with a little rouge.
Mathew sat patiently, anxious to see the results.
“We’re all finished,” they said, each stepping back to marvel at their handy work.
“Have a look,” the goth girl said. “You’re such a natural. Soooo cute.”
Mathew stood up, feeling his posture straighteningout like a board. The heels elongated his legs, and arched his back, causing his butt to jut out, and the skirt to lay freely.
He stepped in front of a tall mirror and he was in absolute shock to see himself all dolled up like a schoolgirl. He didn’t even recognize himself. It was bizarre. A beautiful girl stared back at him in the mirror, a cute round face girl with big curious eyes, dark bangs, ruby lips, and long shapely legs and feminine hips.
“I’d ask her out,” he said, smiling.
The girls all giggled at his little joke; happy that he was happy.
“You ready?” The goth girl asked.
“Ready,” Mathew said, and blew a kiss to himself in the mirror.
The music had stopped bumping downstairs.
That was strange, thought Mathew, as he and girls descended the stairs to go and play the prank on the girl, but they stopped in shock.
The girls turned and ran back upstairs.
Several police officers were there, rounding up the stairs at the party.
“You,” an officer bellowed, pointing at him. “Get down here.”
Mathew looked around.
Most of his friends were gone. They either managed to hide, or escape somehow, but Mathew didn’t know what to do. He was still new at wearing heels, and certainly not prepared to outrun the cops.
The police said, “Weren’t going to arrest anyone. We’re going to call your Parents, and have everyone taken home. Chances were we’d all get tickets.”
Mathew started getting mouthy with one of the cops.
Now, this cop may have been into schoolgirls, or just liked being a hard ass, and or liked being a hard ass to schoolgirls, but some sort of fetish within him existed.
He dragged Mathew outside, pushed him up against a squad car, and asked, “Are you holding any drugs on you, miss.”
Miss? Thought Mathew. The cop thought Mathew was a girl, and was extra careful not to search every nose and cranny.
As the cop cuffed Mathew’s wrists behind his back, Mathew felt the cop’s bulge push through the pleated skirt into his buttocks. The cop held it there for a long moment, grinding his hips into Mathew.
Mathew said nothing that night, and he never told anyone about that, not even his cousins, or the girls, who became some of his best friends, because, truly, being handcuffed and manhandled by that cop turned Mathew on beyond anything else in his life. The fact that the cop had no clue Mathew had a cock, only tantalized Mathew further. It was the most erotic thing he had experienced thus far in his life.
The cop stuffed Mathew in the back of the squad car. He didn’t know it, but under the tented pleated skirt, the front of Mathew’s white lace panties was soaked with come.
Fast forward to now, as Mathew held the beautiful black leather T-strap heels in Aunt Carol’s closet. The memory was getting him hard all over again.
Mathew retired from the closet back to his room down the hall.
He showed quickly, washed with Nair, and lavender soap, then dried off, and went to the bottom drawer of his dresser, where he kept all of his personal things.
He pulled out a fresh pack of nude thigh high stockings, and opened it carefully, laying each nylon leg out on the bed.
From the same drawer, he pulled out a thin knitted white body suit with a turtle neck, no sleeps, and a thong back. His lithe body fit into This like a glove. A rush of excitement filled his heart as he pulled the body suit up, and the thong slide up between his pump cheats. He loved the feel of it on his body, the way it accentuated his unnatural natural curves for a boy.
At once he felt himself getting hard, but that didn’t stop him.
Mathew went to his closet, rummaging behind some heavy coats until he found the purple pencil skirt and the broad brown leather belt on a hangar, and went back to his bed.
He stepped into the skirt, pulling it up high over his waist.
The tight stretchy material clung toHis hips, and lifted his bare cheats up higher, shaping his figure. He cinched the belt tight around his waist to emphasize his curves.
To complete the look, Mathew pinned silver hoop earrings to each ear, and clasped a thin gold chain around his turtle necked neck.
Last, but not least, was his favorite item of all – the heels.
No outfit, Mathew believed, could ever be complete without the Right set of heels. For this outfit, the knitted white turtleneck body suit tucked in and belted over the tight purple pencil skirt, the soft nude nylons, and Aunt Carol’s black T-strap heels feel like the perfect pairing.
Mathew bent, and fastened the thin little ankle straps, and then stood up straight. The heels stood four inches tall, and Mathew did have some practice walking in heels before, but he wanted to master his strides throughout the house, and become as natural and as poised as possible.
Mathew strolled to the bathroom. He unwrapped his bun, and combined hishair part to the right, shaking his head to loosen the brown tempers so that they draped in a rowdy fashion to his shoulders. He leaned into the mirror, and applied some deep maroon lipstick to his wide mouth, added a few strokes of mascara to his lashes, and then walked back into the room.
He grabbed a pair of thick rimmed glasses of his dresser, and put them on.
In a standing mirror in the corner of his room, Mathew saw a well to do professor of some sort, well-dressed, long, and sexy, smart, but with a mischievous side lurking beneath.
Mathew entered the hallway, and basked in the sound of his heels on the wood floor. It was like music to his ears, evenly timed, just the right infection, he thought, as he strode further and his hips began to recall their fluidity.
Soon he was strutting with ease on the darling four-inch T-strap heels, balancing his gait with one foot in front of the other, as if he’d been trained to walk in heels his entire life.
Incredible, thought Mathew, the beauty of the high heel, so easily abused, and yet so easily misused, but what a power they could wild for those who understand.
Mathew felt alive, and so alive in fact that he decided, descending the stairs, that he today he would step outside, walk to the end of the driveway and grab the mail from the box.
Aunt Carol lived with a tall gate surrounding her home so onlookers were never a problem, and the mailbox was just outside the gate. Nothing but a few brief moments in public, and then back to the house, he thought.
Mathew opened the front door, and stopped. Suddenly the end of the driveway felt like a mile away. He hesitated. His legs shook uncontrollably. This happened before. When he got really nervous; when he felt completely exposed, and had a feeling that he would be caught, and made fun of, or talked about, exploited and ostracized, and even worse to him… Humiliated.
He clammed up, stepping back into the house, and closing the door. He wasn’t ready for that yet. Maybe another time, he thought. His mind was too full of bad thoughts, and emotions bringing him down. He was brave a moment ago, but now – he was terrified.
He suddenly wanted to change back into his normal self, and… Mathew sniffed the air; something smelled pungent, like old wet cigarettes, or mildew wafted in the foyer.
A gun clicked behind Mathew, and quiet voice, hoarse like a smoker said:
“Turn around and don’t make a sound.”
Mathew stiffened, and slowly glanced back over his shoulder.
A man in a ski mask held a pistol on him.
“I said turn around, and don’t make a sound,” he repeated. “Do you understand me?”
Mathew stared at the man, eyes wide, his body frozen stiff.
The man easily stood over six-feet tall, built like a refrigerator, with dark, narrow eyes blazing with intensity behind the mask. The type of man who probably never lost a fist-fight, thought Mathew.
“Nod your head ifyou understand me, little girl,” he barked.
Mathew nodded.
“Then turn the fuck around!” he bellowed. “What’re you waiting for? You wanna get shot?”
Mathew shivered. He carefully turned around, instinctively raising his hands.
The man stared at Mathew for a long while, taking in the woman in the skirt and tight turtle neck standing before him. He grinned. “Tell me your name, sweetness.”
Mathew cleared his throat; his legs trembling in the high heels. He suddenly wished he wasn’t wearing them, but like it would matter. It was like the cops all over again; he couldn’t out run this man.
“Tell me your name,” the man repeated. “Now.”
Mathew didn’t want to say that his name was Mathew. Even in this moment of a hold-up, he still Didn’t want to reveal that he was a crossdressing fairy. The man might actually shoot him.
Mathew raised the pitch of his voice to a perfect female imitation, the one he practiced for years when he was alone.
“Maddy,” Mathew said with a slight quiver. “My name is Maddy.”
“Is there anyone else in the house?” the masked man asked, keeping his pistol on Mathew, well… Maddy from now on.
Maddy shook her head no, there wasn’t.
“Don’t lie to me,” he said. “I don’t have time for your shit right now.”
“I’m alone,” Maddy plead. “There’s no one here.”
“Anyone coming home soon?”
Inspiration hit. “
Leave a Reply