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.

“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 color 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 behavior. 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.

“Why me?”

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 dismissive words.

“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 behavior 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.

 

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