Under His Stiletto (crossdressing discipline M/M romance), page 1
Table of Contents
Under His Stiletto
--- No discipline until you’ve had your greens! ---
Mike doesn’t like overcomplicating things. At thirty two, he’s nowhere near settling down and divides his time between his construction job and the pub. Then his life becomes everything but simple when his coworkers catcall the wrong person, and Mike ends up punished for it. Which doesn’t seem all that bad, since he loves punishment and discipline.
Loves it so much in fact, that he will do anything for more licks from the sexy crossdresser’s belt.
Living in a state of perfect domestic bliss where he does as he’s told, and in turn gets freshly baked cookies and his laundry done, lines blur all too quickly, and it might just be Momma not Mike who is skittish about relationships.
Despite all the hoops he has to jump through, nothing can scare Mike away, because he is a good boy and he will prove it no matter what punishments Momma has him endure!
Themes: commitment issues, discipline, crossdressing, role-play, dirty talk, punishments, identity, spanking, bullying
Genre: M/M contemporary romance, BDSM
Length: ~22,000 words (standalone story)
WARNING: Adult content that might be considered taboo role-play. Explicit content, strong language, discipline. Reader discretion advised.
This is a work of fiction. Any resemblance of characters to actual persons, living, dead, or undead, events, places or names is purely coincidental.
No part of this book may be reproduced or transferred in any form or by any means, without the written permission of the publisher. Uploading and distribution of this book via the Internet or via any other means without a permission of the publisher is illegal and punishable by law.
Text copyright © 2018 K.A. Merikan
All Rights Reserved
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Other books by K.A. Merikan
“Hey, pretty bird! Flown here all the way from the tropics?”
“Come on, won’t you talk to us for a second, lovely thing? We don’t bite!”
The woman would have turned any man’s eye. Walking with a sexy wiggle in a tight dress that revealed long, shapely legs up to the knee, she was a drop of colour against the background of the town’s genteel beige architecture. Her pink skyscraper-tall heels matched the outfit and her face had an ageless quality that placed her somewhere between late twenties and early forties. Despite it being springtime, she wore white gloves, as if she were too genteel to touch any dirt the world around her held. Her hair was a statement in itself, one of those retro styles Mike had seen women wear sometimes at parties. Rolled up high on both sides of the head, with loose ginger curls at the back, the hairdo wouldn’t have been out of place in Mike’s nan’s knitting catalogue.
Dave, one of Mike’s co-workers stepped out of the restaurant they were redecorating and whistled loudly. “Don’t be like that, girl! I’ve got what you need!”
She stopped, her high heels perfectly aligned on the pavement, the full ass so firm under the tight pink fabric. Mike might have salivated when she turned and rushed their way, keeping her tiny crocodile skin bag close.
Dave looked back at Mike and their two co-workers, proud of his success, but the smile dropped off his face when she slapped his chest with her handbag.
“How dare you harass me in this manner? Don’t you have anything better to do than bothering ladies who mind their own business? Nobody owes you their attention!” she reprimanded him, shaking her finger at them.
Mike’s blood dropped to his feet as he stood in the open shop window, staring at Dave taking the woman’s anger for all of them. Only she didn’t sound like a woman. Her voice, while soft and high-pitched, was definitely on the masculine end of the scale.
“This is unbelievable. I will make sure your boss hears of your behaviour. And if he can’t make it stop, I will take things further, mark my words. Good day.” She swiped her blue gaze over the three of them before turning on her heel and walking off in that same sexy gait that had Mike staring after her like a puppy after its mistress.
Roger, another one of Mike’s co-workers glared at Dave. “She can’t do that! Fuck, mate. If my missus finds out, I’m dead!”
Mike stood frozen, blood curdling in his veins. Did these two clowns even realize that this woman was possibly transgender, and they’d have a shitstorm on their hands if she decided to pursue this further, with people assuming the three of them had been mocking her?
Dave made a miserable face. “Mike, go talk to her,” he whisper-shouted.
Roger grabbed the few hairs he still had left before dropping his arms in a display of frustration. “Because you’re the heartthrob. If we were One Direction, you’d be Harry.”
Dave raised his eyebrows, so Roger went on.
“What? I’ve got a teenage daughter.”
Dave snorted and grabbed Mike’s shoulders, pushing him to the door. “Yes, you’re the hot one, Mike. My mum said so too. Come on, mate. Take one for the team!”
Mike rolled his eyes, begrudgingly pocketed the manipulative compliments, and sped out of the restaurant. The last thing they needed was their asshole of a boss coming down on them for harassing someone while on the job, but truth be told, the opportunity to talk to that bombshell of a woman had its own appeal.
“Hey! Hey, babe! Wait up!” he called out, once he spotted her in front of a picture-perfect flower shop.
Her eyes snapped toward him, and she quickly made her way farther down the street, set on ignoring him, even though that only offered Mike a better view of her shapely backside and the long legs that moved faster and faster as the woman ran from him.
“I don’t mean any harm!”
She stopped in her tracks and raised her hand, turning around. “You’ve done enough!”
Mike jogged a bit closer, hoping not to cause a scene, though a few people were definitely staring from the wine bar on the other side of the road.
“Hey. Sorry, the boys just like a bit of banter--”
“That was no way to speak to a lady!”
Mike licked his lips. Yep, he definitely spotted an Adam’s apple. Navigating this kind of stuff had never been his strong suit, but he’d met enough trans persons in his life to know a thing or two. “They know. If you came back, they’d surely apologize too. Please don’t make it a big deal to our boss. He’s a hardass.”
She rolled her eyes and hugged the bag to her chest. As she moved her head, a subtle pearl earring glinted in the light, beckoning Mike to look closer, and closer. He couldn’t see any traces of facial hair. The illusion of feminine physicality so complete he wouldn’t have thought her anything but a regular woman wearing fashions from the mid-twentieth century. Her lipstick was a cold red, and her eyes, winged with black eyeliner, watched him with such temptation despite the
“I don’t see why I should do you any favours. If your only motivation is fear of your boss, then you don’t deserve my forgiveness.”
Fuck. Mike hadn’t thought through his arguments. “No! No, no, no, it’s about much more. The guys, and me too, we’ve realized our behaviour was wrong.”
She pouted at him, and the way she squinted promised nothing good. “And this is the kind of bullshit women have to put up with. Sucks for you that I’m not one. What time do you finish work?”
Mike got so thrown off, he just stared, unsure how to proceed after that declaration. No trans woman he knew would have ever said that she wasn’t a woman.
The beautiful yet confusing creature in front of him snapped her fingers.
“S-six,” he choked out.
The lady exhaled and opened her bag. After a moment’s rummaging, she handed him a business card illustrated with women in retro-style clothes. The business was called ‘Momma approved’ and involved custom outfits.
Mike couldn’t help himself and swept the lady with his gaze from the tips of her toes to her beautiful, androgynous face. She raised her brows and tapped her finger against the card.
“Address is on the back. Come over at 7 pm sharp, and I’ll see what I can do,” she said, meeting his gaze.
“S-say again? I don’t really understand.” He stared, hot and cold all over, cooking in the sauces of his own confusion.
The lady shook her head. “Young man, you need to be punished for your actions. I will not let you off the hook just because you said sorry. Be there, or face the consequences of your actions,” she said and walked off, without waiting for an answer.
Mike squeezed the business card and bit his lip like a schoolboy told to pull his pants down.
So. Fucking. Hot.
Mike’s life took an unexpected turn and he was now entering a new dimension where his wet dreams were reality, and a hot, feminine person who wasn’t a woman wielded power over his life or death. As he stood in front of the cottage with a perfectly groomed lawn, he half-expected the lady to open the door for him wearing black latex and holding a whip.
He couldn’t get over how she’d managed to put him in his place despite being half his size, wearing a wiggle-inducing dress, and heels that were fit to punch through people’s skulls if she wished to.
And yet, her house was the most perfect tiny thing built with local stone and buried between green hills, a fifteen-minute drive from the nearest town.
Once the work had finished for the day, Mike barely had managed to take a quick shower and dress at the hotel where he and his co-workers lived for the duration of the restaurant renovation. And he’d still picked up some flowers despite having to speed down the narrow lanes.
It was surreal.
What did she even want from him? The dirtiest, sexiest images tumbled through his head as he walked through the garden and knocked on the door.
It soon opened, and he was once again treated to the sight of her. She’d changed since morning and was now wearing a flared dress with a print of red and white stripes under a clean white apron. Like before, the neckline of her dress was rather high and only revealed elegant collarbones.
“You came,” she said approvingly and stepped aside. The broom in her hand made Mike conjure images of it hitting his bare arse, but it was soon replaced by the flowers that she accepted without comment.
“My mum told me never to say ‘no’ to a lady.” He gave a sheepish grin, eager to find out what he was in for.
“Your mother is a wise person,” the lady said, leading Mike into a parlour that, at first glance, seemed to be a recreation of the style prevalent several decades back. But the longer he looked at the faded colours of the interior, he realized that the furnishings weren’t just inspired by the 1950s but the real thing. He said nothing as his hostess herded him to the flowery sofa and made him sit in front of a coffee table that could have been an item from his grandmother’s attic.
Asked what he wanted to drink, he settled on tea and was left alone with a whole cabinet of tiny china and glass poodle figurines.
What had he gotten himself into? Whatever it was, he could only hope it would end with his dick out. “Like the place, love!” he yelled from the sofa, unable to stop himself from stirring in his seat.
“I am most definitely not your love,” called back the lady, but nothing about her demeanour changed. Mike found himself intently listening to the clicking of her heels against the floor. Did she always wear those kind of shoes at home, or was it because she was interested in him, and the whole thing was an elaborate way to get him into bed? Why else would she have asked him to come over?
A loud whistling sound tore through the air, but it was cut short, and just moments later she returned to the front room carrying a tray containing a vintage teapot with matching cups, and a plate of biscuits.
But there was no Hobnob or Jammie Dodger in sight. This domestic goddess was serving him homemade biscuits. This was happening. He was in.
He grinned and ran his hand over his short hair. “I don’t deserve all this.”
“Correct. You’ve yet done nothing to deserve my gratitude, so let’s call this an advance for your future efforts,” she said, all dignified in the way she picked up two biscuits with long fingers adorned with a bright red manicure.
“I will put in so much effort.” Mike smiled even wider and dipped his biscuit into the tea that was the perfect strong brew with just a dash of milk.
He didn’t care that he didn’t understand what the person in front of him was about. She was so hot he wanted to dive under her petticoats right then, right there on the Moroccan carpet that smelled of lavender.
She smirked. “Words, words. Now eat. My conscience won’t let you start before you’ve had a bite.”
There was much more he wanted to taste, but he’d settle for a homemade biscuit. “So…excuse me if this is too intrusive, but you said you’re a lady, but then you said you’re not a woman? Can you help me get my head around that?” Was he being polite enough? He had no idea, but fortune favoured the bold.
She thought about it for a second, dunking her biscuit before having a taste. “Well... I’m not. I always liked to look like one, and perhaps even live a bit like one, but I still am a man,” she (he?) eventually said.
Mike squinted, and took his time sipping tea. ‘He’ definitely didn’t suit her. “So you’re not transgender?” He couldn’t get his eyes off the mysterious person in front of him.
She swallowed and offered him a pretty smile. “I like to think of myself as a full-time transvestite. Aren’t you a curious one?”
Mike gave a nervous laugh and munched on the delicious biscuit that had bits of sea salt and caramel. Fucking A. “I’ve lived a little,” he said smugly.
His hostess watched him from behind the cup, flirtatiously wiggling her foot in the air. “Men. Always wanting to appear like they know it all.”
“I still don’t know your name.”
She laughed and winked at him. “I don’t think you deserve it yet. If you insist, you may call me Momma. That’s my female persona.”
“So are you crossdressing as an… older lady? Doesn’t show.”
She rolled her eyes playfully and rose, waving at him. “Up. I can see you’ve finished your tea. I’ve got some garden work for you to do to repent for your rudeness.”
Mike bit his lips. Garden work? “I can be useful in many other ways…”
Momma cocked her head. “I think we don’t understand each other. You owe me a favour for being disrespectful, and I need a male hand in my garden. If you’re eager to fix the sink too, I will not stop you.”
Mike sighed. If he was to do any gardening, he needed to hurry, because it was getting dark already. Momma led him into her backyard and set him to work on shearing the bushes that had overstayed their welcome.
Half an hour after he’d started, Mike’s initial disappointment had
Still, he continued with his work even as the evening truly settled, and he needed to rely on lights tucked inside flamingo statues scattered around the garden. Despite the late hour, it was still so hot and humid Mike ended up taking off his T-shirt. He worried Momma would think he did it to impress her, but the truth was that if he were to impress her, he couldn’t be all sweaty by the end of this.
The tap of heels against concrete sent a shiver down Mike’s spine and he looked back at Momma, whose figure loomed against the dark background. She switched on a flashlight, stepped out of her high heels and continued through the garden barefoot. As she reached the sheared bushes, she proceeded to study the plants in detail.
Mike frowned. “What? Not good enough for ya?” So he’d done a bit of a half-arsed job at the end. Big deal. It was cut, just like she’d asked.
She exhaled loudly and glanced at him across the lawn. “For all your big words, you did a very sloppy job. I must admit I’m bitterly disappointed.”
Mike raised his arms in frustration. “Well that makes two of us.”
“I wouldn’t know why.”
“Maybe ‘cause you invite me over to your house in the evening. What’s a guy to think?”
She crossed her arms on her chest and turned so fast her skirt floated over the petticoats. “How insolent! I don’t know you, and I see no reason why on earth you’d have come to this conclusion. I should spank you for talking to me like this!”
Mike’s heart filled with heat that soon drizzled to his balls as he followed Momma into the house. “Maybe you should,” he muttered under his breath.
“What was that?” she asked sharply.
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