Getting onto the pantyhose ladder (Monthly tale - 15) X

(Man into woman)*

Five minutes before the coffee store opened, Rupert was already there, waiting outside the door.

The very tall and skinny pale looking guy was, just like every day since he had got his new job three months ago, diligently enthusiastic about his mostly menial work.

Wearing his office clothes - a clean white shirt without a tie but with black pants, he was the first to enter the store to get the orders for his entire department.

Satisfied, and carrying plenty of coffee, the intern headed back to Thermal & Co’s office building, while whistling the whole way.

It wasn’t even close to being a big company, but it was by far one of the countries best.

The oddity?

Nothing too special, it was just that the proportion of male to female employees was seven women to every man.

Rupert didn’t care much about that, or at least not as much as he had when he started working there, it was a bit weird, but nothing too worrying and he was happy with his job, Thermal & Co. was a fantastic stepping stone in the business world or maybe even as a permanent position.

The women didn’t treat him too badly, outside of the usual jokes and teasing, and for a guy that tended to prefer ladies, working in a place full of girls was quite the plus point.

There were some other odd things that he also hadn’t considered much, like how such gender disparity could be maintained despite most of the interns being men... but he was sure there was a good explanation... probably...

But that day, as he pushed open the entrance door with his foot and stepped inside with a big dumb smile, Rupert, like many of the men working for that company, didn’t have a single concern on his mind... yet...

...

Three women sat in the bosses office.

Miss Vaugh, was sitting in the big chair behind the desk, just like the boss she was.

Flowing curly dark hair and a gray business pants suit, wearing a pair of earrings with purple stones, she exuded control, dominance and security.

In front of her sat Amaya and Mildred.

Mildred was that girl in the office, you know the one, there’s always one, the one that remembers everybody’s birthday and also bakes a cake.

Wide, with short blond hair, blue eyes and a perpetually cheerful expression, with a thin woollen scarf across her shoulders.

At her side, Amaya was and seemed like the exact opposite of the blond woman.

Amaya was a dark skinned woman, you might have said of Indian ancestry, her long dark hair tied in a very tight ponytail, all serious and businesslike, just like her clothes and her very, very round pregnant belly.

She was a little annoyed at having been called into Miss Vaugh’s office, and didn’t even attempt to hide it.

Miss Vaugh tapped her long fingernails together in front of her girls.

“Girls!” she announced, smiling widely as she looked at Mildred and then at Amaya. “It’s time to promote another guy!”

Mildred clapped with the enthusiasm of a little child.

“Hurray! Hurray!”

Amaya gave a sigh that sounded like a grunt.

“Can’t the lazy asses in Human Resources handle it?” she asked.

Miss Vaugh shook her head.

“No, Amaya, they did it last time and this lucky guy is going to be promoted into the accounting department, and as the heads of that department it’s your responsibility.”

“Hurray!” said Mildred again. “I love it when we get a new chick in our nest!” she gave Amaya a happy puppy look. “Isn’t it great?”

Amaya gasped, rubbed her forehead and crossed her arms below her ample breasts brimming with milk.

“OK... so, who’s the poor idiot this time?”

Her question seemed good enough to Miss Vaugh.

“Rupert A. Taylor” she said.

Amaya made a poker face.

“That name doesn’t ring any bells...”

Mildred gave her companion’s shoulder a gentle push.

“Don’t be silly, silly, he’s the nice boy from the second floor! Skinny, pale, tall, with a short beard, buys the coffee for everybody every morning, very polite, but gets super shy around women, his birthday is in September, twenty-five years old, got hired in May, likes nerd stuff, lives in...”

“OK! OK!” shouted Amaya lifting her arms, interrupting the long stream of mostly irrelevant information about the guy. “One of the interns, I get it!” she looked at Miss Vaugh. “Why him?”

Miss Vaugh leaned back in her chair, taking the question with a wide grin.

“Isn’t it obvious? He’s just a total pussy.”

Even Mildred knew not to push when the boss was like that, Amaya nodded.

“When do we have to do it?”

With an even wider smirk Miss Vaugh leaned forward like a predatory beast and threw a ball of dark fabric that Amaya caught midair, then she softly said.

“Today.”

...

It was midday, Rupert was in his small cubicle on the second floor, the day’s work was advancing well and his brain was already happily thinking about lunch.

Until he turned around and saw Mildred standing in the entrance to his cubicle.

He was surprised by her presence, but the kind happy-go-lucky woman didn’t intimidate him too much, it was seeing Amaya behind the blonde that made him straighten up and gulp.

“Oh, god...” he gasped. “I did something wrong? Was it the last schedule? Am I fired?”

Mildred stepped in, calming the guy down with a rub on his shoulder.

“No, no, no, no, don’t worry, Rupert, dear, rather the contrary, you are doing great! We are here to propose something to you, something very, very, very nice!”

Rupert was still looking at Amaya, the pregnant woman had her arms crossed and was already frowning, clearly annoyed by his scary cat attitude.

“W-what?”

“Something nice, something nice, no worries! You look hungry, dear, do you want to come with us to get something to eat?”

Mildred’s wide smile was warm and reassuring, but the guy answered without taking his eyes from Amaya.

“S-sure...” he said. “Now?”

“Yes, of course now, it’s almost break time, isn’t it?”

“Yeah...”

“You can leave a bit earlier today, your mamas give you permission!” Amaya rolled her eyes when Mildred said the word mamas, Mildred put a finger on her lips. “But shhh! Don’t tell the other boys... they could get envious and discover that you are a favorite...!”

Rupert nodded, Mildred giggled.

“Cut the crap already!” grunted Amaya. “I’m starving and want to get finished with this already, let’s get moving!”

The guy immediately stood up, following Mildred as she followed Amaya, he followed her so closely that when Mildred stopped to theatrically put a hand on her forehead he hit her back with his nose.

“Oh, dang!” said the blond. “I forgot the makeup on my desk! Gonna pick it in a tick, wait for me in the break room!”

She quickly left before the other two could answer.

Amaya shook her head, then she began to walk towards the break troom, expecting Rupert to follow... which he did.

The break room was empty, Rupert sat in one of the chairs, near the microwave, Amaya stood against the wall with her arms crossed.

He didn’t even seem to have the courage to look at her face and that only made Amaya’s annoyance grow.

“Goddammit...” she growled. “Look, baby, I’m not gonna piss around the bushes with flourishes and cheap tricks and second meanings... like those bitches did to me...”

The pregnant woman was lost for a moment in her thoughts.

Rupert raised his head, curious about what his superior was saying.

“What do you mean...?” the guy asked.

Amaya came back to the world.

“Look, listen to me, you are being promoted, but to get promoted we have to transform you into a chick.”

“A chick...”

“A woman! If you don’t run away you are going to lose your cock and grow a pair of tits and will be a girly girl from now on, do you understand?”

The blunt, clear and harsh honesty of the pregnant woman made Rupert blush and blink as if he was already that girly girl.

“Heeem... no...?” he scratched his head, feeling warm and spit out the first question waiting in the front of his brain. “W-why?”

Amaya shrugged.

“It’s how things work in the company, it’s in the contract, but I bet you didn’t read it... If you sign this you give us permission to suggest and perform permanent gender reassignments... Sure you missed that part, didn’t you? I missed it too, probably it’s illegal as fuck, but all good jobs have their traps.”

Rupert’s brain gears were still having a hard time spinning.

“But I don’t get it... why me...?”

“Bosses orders, she says you are a pussy and her whims make balls drop...” she chuckled. “To be honest, you totally look like a soft cunt to me!”

The young man felt as if he should debate that mocking statement and perhaps re-emphasize his questioned masculinity, despite feeling his penis starting to... tingle, but he was left with an open mouth when the door of the restroom opened and Mildred stormed in.

“I’m here! I’m here! Sorry for the wait! You’re sitting up already? Great!” she put the makeup tools on the table at Rupert’s side and began to get them out while humming.

Rupert looked at her and then at Amaya’s sharp smirk.

“Don’t worry, baby, just let her do her magic!” said Amaya, enjoying the scene.

Mildred picked up a moist skin-cleaning wipe with one hand and Rupert’s chin with the other.

“But... wait...!” mumbled the guy.

“Shh... Don’t move, little chick, it will take only a moment... and you are going to love it...!”

The damp cloth rubbed his face softly, too scared to protest and too intrigued to run away, he sat stiffly as the woman prepared him for a makeup session.

Mildred cleaned his skin, shaved his facial hair, narrowed his eyebrows.

Rupert thought it was over after that and he shivered when he saw Mildred pulling out a large lipstick.

A vivid coat of red painted his lips.

“Close them together, little chick!” ordered the blonde, he obeyed and his hard dick trembled. “Great! Just like that! Now close your eyes...”

He willingly embraced the darkness with his heart as Mildred’s soft fingers did their job and Amaya’s chuckling sounded in the distance.

Colour on the cheeks, mascara for the eyelashes, paint and brush, cream and perfume...

“And... done!”

Rupert opened his eyes and was met by Mildred’s and Amaya’s smiles, both leaning over him, the blond woman excited and the pregnant one satisfied.

“Not bad at all...” said Amaya will nodding.

Happy and cheery Mildred pulled out a mirror from her makeup bag.

“Here, have a look little chick!”

The guy lost his breath at the sight of his own reflection, his male fingers touched his female face, feeling the soft skin and he still found it hard to believe that the girl in the mirror could be him.

Puffy lips, tender skin, big blueish eyes...

“I’m... a girl... already...?”

Amaya laughed out loud.

“No, you idiot, but you are one step closer, that’s for sure!”

Mildred frowned like a child.

“You told him?! You meany!” she gave Amaya’s shoulder a very weak slap. “You ruined the surprise!”

Amaya stuck her tongue out.

“Who cares?” then she bit her lips after taking another good look at Rupert. “Dammit, the boss was right... you look like a freaking model or something... Shit, I feel kinda envious...”

Mildred quickly put her tools back inside the bag, Rupert continued to be dazzled by his own reflection like some sort of modern Narcissus.

“This is insane...”

The blonde woman giggled.

“Nah, it’s just some healthy cross-dressing!”

“Enough of that!” barked Amaya, cutting through the other two’s chat. “We still have to make a stop before the food and I’m starving, so don’t make momma angry and move your asses.”

Rupert blinked.

“Wait... I can’t go out looking like this!”

Mildred was already grabbing and pulling him towards the door.

”Of course you can!” she said. “You look fantastic!”

He found himself pushed out of the restroom into the wild office environment before being able to utter any other protests.

Blushing in shame he followed the two women as his brain and eyes spun, looking at his feet and feeling all the eyes of the company on his shoulders.

“Hey, who’s that cutie?” said a voice.

Rupert raised his eyes slightly and saw two of his male intern companions, Johan and Russell, they were looking at him as if he was a very desirable cupcake.

He wanted to die, they were two of his best friends, he worked with them and they were lusting and bragging over him as if he was the bosses new secretary.

The guy felt his building erection dying out, but his nipples began to harden, maybe because his heart was beating so hard.  

“YOU TWO!” shouted Amaya, looking back and pointing at the two horny interns. “Leave her alone and get back to work or I will kick your asses!”

Johan and Russell straightened up simultaneously and simultaneously they answered.

“Yes ma’am!”

The two guys hid behind their work and Rupert focused his attention back on his feet, but couldn’t get rid of the nagging sensation in the back of his head of the eyes of the guys on his butt.

They reached the safety of the elevator, Rupert moved into a corner, trembling like a doe, his chest feeling heavy, swollen.

Amaya look at him out of the corner of her eye and muttered.

“You can leave if you don’t like it, nobody will blame you, but this may be your last chance.”

Rupert blinked a couple of times, the doors of the elevator opened and the two women left and... he followed them, avoiding the security guard’s glances.

Maybe because he had so many things dancing around inside his skull, he didn’t realize that the street was going to be even worse, more eyes, more people.

Mildred held one of his arms as Amaya lead the way.

He could have melted, especially when a group of young girls made comments about his lipstick.

The guy was feeling so small, in a literal sense, he looked at Amaya’s back and at Mildred’s reassuring smile, they were now taller than him and he was sure that wasn’t just his imagination.

“I really am melting...?” he wondered.

The stop before food made his balls shrink: A female underwear store.

“I can’t...” he began to say.

“Yes you can!” said Mildred, dragging him inside.

Amaya yawned.

Rupert found himself shivering in the middle of the store as the two women looked around the shelves.

“I have to buy some new panties...” explained Amaya, picking up a pair of elasticated ones and giving them a look. “But maybe it’s a waste of money... I’m going to pop any day...”

“That’s a terrible way to imagine the wonder of giving birth!” proclaimed Mildred. “And you should totally buy those ones with the cute ducklings!”

“Not in a million years!”

Rupert glanced shyly around as the two women kept chatting and shopping, just the sight of underwear for women, all those panties and bras and fancy nightclothes, so soft and sexy, made him gulp.

He put a hand on his chest and felt the slowly swelling mounds, pressing his shirt against his erect nipples, he had known since before they left the restroom that something was changing, not mentally, but physically, he felt it... and it felt good... he didn’t want to run away and yet...

“Hello, miss?” one of the smiley female store clerks as she approached Rupert, catching him by surprise, which made him let out a small squeak. “Looking for something specific? Do you need any help?”

“No... I am... fine...” he mumbled and had to put a hand to his neck when he heard his own voice. “I’m just... waiting for my friends...”

The store assistant nodded.

“OK, if you do need anything just ask!”

Rupert nodded back as she left, he was expecting that anybody who had looked closer at his face would notice it, that there was something wrong... but the girl didn’t... maybe because there wasn’t anything wrong...

He returned to rubbing his shirt against one of his small but growing tits, it was so soft... he kept shrinking as his hips widened... the warmth in his crotch...

“Look, girl!” Mildred called to attract both Amaya’s and his attention and they both looked as the blonde showed them an incredibly sexy set comprising a satin corset with stockings - fishnets, open at the chest... and at the groin... Mildred smoothly asked. “Can you imagine yourself wearing this?”

The perhaps devilish question coincided exactly with the moment at which Rupert’s pants decided to drop to his knees.

Rupert squealed and quickly ducked, grabbing the pants and pulling them up, he ran away, outside of the store, and from the eyes.

Once outside he stopped against a wall, with tears in the corners of his eyes, pulling his pant’s belt tight so they didn’t fall down again, he didn’t have any hair on his arms or legs but if any was left if was too sparse to be noticeable... and the bulge in his briefs was... pretty lacking...

He just stood there, trying to hide, trying to keep his mind blank as his slow burn metamorphosis progressed, erasing masculinity for something sweeter.

The automatic door of the store opened and closed a couple of times before Amaya and Mildred came out, carrying numerous bags containing a lot more clothes than just a pair of panties.

“That was pretty funny, baby face!” said Amaya, clearly mocking the confused guy. “I thought you were a pussy, but you are more of a scared mouse!”

“Not... funny...” mumbled Rupert, his tears having made his makeup run a little.

Mildred, stoked by Rupert’s girly cuteness, quickly hugged the intern, almost intentionally making sure that her more ample bust touched his small forming one.

“Shh... it was just an accident!” she said tenderly, tapping his head, feeling the hair grow a little. “Don’t listen to bad momma Amaya, she’s just a meany!”

Amaya shook her head.

“You are going to spoil her...!” she scratched her belly. “I’m even more starving now if that’s possible...”

“Shopping does make us ladies hungry, isn’t that right?”

She looked at Rupert, expecting an answer.

Rupert nodded softly.

“Yes... I am hungry too...”

Amaya nodded as well.

“Nothing else to talk about then!”

The three women moved towards the tastiest restaurant in the shopping centre to get a well deserved meal and as they walked Rupert’s shoes just became looser and looser.

They sat near a window, the waiter soon came over to take their orders, Mildred quickly asked for a salad and then it was Rupert’s turn.

“Hmm...” he looked at the menu, pursing his lips, thinking too much about an insignificant decision.

Amaya, tired of waiting, gave her command.

“A large well done steak, with potatoes and something cold to drink.”she gave the menu to the waiter and looked at Rupert. “She will have the same, won’t you, babe?”

Rupert nodded.

“Yes... but with extra potatoes, please...”

She also gave her menu back and the waiter left with red cheeks.

As the girls ate their food Mildred brought a new intriguing topic to the table.

“So... what are we going to call you?”

The blonde was looking directly at Rupert and made him freeze with his fork of potatoes in midair.

“Heeem...” she lowered the fork. “Ru... Ruperta...?”

Amaya slammed her fist in the table, scaring the other two.

“I knew you were going to say something stupid like that!” she said quite loudly despite being in a public space. “Not in a million years! You need something fancy... something soft...” she took a long look at the girl, making her slightly uncomfortable, in much the same way that her hard nipples peeking under her shirt were making her feel. “Jazmine... with a zee...”

Mildred clapped.

“Uuuuh! I like it! I like it! Do you like it?”

Jazmine thought about it for a moment as if she hadn’t yet decided.

“Yes... I like it...”

The three women toasted that and Mildred then had to go to the bathroom.

“I still scare you?” the pregnant woman asked.

“A bit...”

“Hmph... you are coping with it very well... way nicer and quicker than when I transitioned...”

“You were a...?”

“Yup, I was, long ago...” Amaya put a hand on her pregnant belly “It isn’t like it mattered much for a long time...”

“If you don’t like... don’t like this, why didn’t you leave?”

“Because I’m a big titted idiot?” she chuckled. “I didn’t run away for the same reason as you, I love it... like you are loving how your balls are slowly shrinking right now.”

Jazmine lowered her eyes.

“Mildred too...?”

“Mildred? Nah, she was pussy from birth. Were you thinking that all the women in the company were once guys? That would raise way too many questions, dummy, just a few guys per year receive your privilege.”

“As if it didn’t already raise questions...” mumbled Jazmine, watching as her own nails grew longer in front of her eyes.

“You will get all the answers that matter, eventually.”

“You got them...?”

“Some of them.”

“I have one question...”

“You don’t have to do it with guys if you don’t want to, you probably still prefer the ladies, I know I sure do.”

“You do?”

“Of course I do, but I wanted to try all the possibilities, I’m sure you’re thinking about getting a bun in the oven already, am I wrong?”

Jazmine looked directly into the satisfied pregnant woman’s eyes.

“...no, you aren’t...”

Amaya didn’t lose her smirk.

“Getting pregnant doesn’t mean that you can’t go around chasing skirts, baby... Oh, before I forget...” Amaya pulled a ball of black fabric from her pocket and put it on the table, close to Jazmine’s hand. “Miss Vaugh wants you to have this, a little gift, a tradition, if you want to climb the ladder you have to wear them.”

The girl pulled open the cloth ball, it was a pair of very sheer dark pantyhose that felt amazing against her fingertips.

As she inspected the pantyhose Mildred came back and complained again.

“NO WAY! You gave the gift before I came back!”

Amaya shrugged.

“If you didn’t have to go pee like a toddler you would have seen it.”

Mildred dropped into her chair, puffing out her cheeks.

“You are being the worse today!” she snarled.

Jazmine got up, with the pantyhose clutched against her chest.

“I’m... going to the bathroom...”

The other two understood, they watched with a certain sense of silent pride as Jazmine left for the bathroom, the women’s bathroom, and nobody seemed to find it weird.

Amaya’s eyes opened wide...

Mildred looked at her.

“What...?”

The pregnant woman leaned back in her chair and put a hand on her belly, something leaking onto the floor.

“Oh, oh...”

...

Jazmine entered an empty stall.

As soon as the door was closed she kicked off her shoes and unfastened her shirt, then she sat on the toilet and looked down.

Perky boobs topped with puffy nipples were the first things she saw, tender like cupcakes she grabbed one and bit her lips.

Then her waist, hourglass shaped with well formed hips, a tiny round behind.

She ignored her crotch for a moment and looked beyond that, to her long shaved legs.

The girl felt fuzzy and happy, her body still changing, not much left of the guy she was this morning, only the thing between her legs.

A perfectly feminine body.

Jazmine spread the legs and gave her attention to the remains of Rupert’s dribbling masculinity.

The small flaccid penis hung down, flaccid under the bush of pubic hair, her trembling fingers thought about touching it for a moment, but she tossed that idea away.

Instead she grabbed the pantyhose, put them on her feet and began to smooth them up her legs.

She pulled them firmly until they reached her groin and keep pulling, squeezing her previous genitalia with the translucent fabric, compressing it.

An earthquake of pleasure as her sex morphed - trapped in the pantyhose, moistening the cloth, shrinking, being sucked inside her pelvic area.

Jazmine moaned loudly, not caring about who might have been listening, tasting every second of the sculpting of her petite and needy vaginal lips.

A succession of waves of orgasms she fell back in the stall, gasping and rubbing one of her breasts, pinching it’s cute pink nipple.

She couldn’t help but laugh as the changes ended and the pantyhose, even if they were now a bit ripped, moist and warm, fitted her more than perfectly.

The girl rose up, fastening her shirt over her hard nipples and leaving her pants and shoes behind she left the bathroom in her pantyhose, and the sock she was still wearing, covering her feet.

Later she would realize that she had left her wallet in those pants, along with a few other things, but, overall, she wouldn’t be bothered about that.

Jazmine came out from the bathroom to find herself in front of a scene of ruckus and chaos.

In the middle of the large dining area there was a group of people surrounding Amaya and Mildred, who were both on the floor, Mildred kneeling and Amaya lying down.

Amaya wasn’t just laying down, she had her pants and panties down, her legs spread and panting with a red face like a locomotive engine while giving birth.

Lucky for her there was a doctor in the restaurant that was taking care of the situation.

“You are doing great, miss, it’s going to be a quick one!” said the doctor.

“FUCK YOU!” yelled Amaya.

Jazmine ran towards her companions and knelt down on the other side of Amaya, her hand was immediately grabbed by the soon-to-not-be pregnant woman who yelled loudly.

“AAAAAAAAAAAAAAH!”

“Just... just keep bre...”

“If you say keep breathing I will strangle you!”

Jazmine looked at Mildred.

“Where’s the ambulance?!”

The blonde was holding her cellphone to her ear with the hand that wasn’t being gripped by Amaya.

“They are on their way, they will be here in ten minutes!”

Amaya squeezed both the other two women’s hands.

“WE DON’T HAVE TEN MINUTES! GYAAAAAAAAAH!”

“Just one more push!” said the doctor from between her legs. “It’s almost out!”

Holding her breath Amaya put all her will into that final struggle... after a moment of heavy silence and a cutting sound the cries of the baby began to resound around the restaurant.

“Congrats, miss!” said the doctor, putting the newborn in his mother’s arms. “It’s a boy!”

Amaya was crying only slightly less than Mildred as she held the small, noisy thing with it’s wrinkled red skin, her eyes sparkling with motherhood.

Jazmine thought it was pretty ugly, but she didn’t say anything when Amaya looked at her with a wide smile.

“Yeah, well... at least for now... hey, Jaz?”

The girl smiled back at her friend and nodded, embracing the warmth of the moment and of her bright future.