Under His Stiletto (crossdressing discipline M/M romance)

by K. A. Merikan

  “You know, you did say you’d punish me.”

  Silence settled over the kitchen, suddenly becoming so loud it rang in Mike’s ears. Finally, Momma spoke in a low yet breathless voice.

  “Come here, you naughty boy!”

  Mike’s dick twitched at the sound of that, but he tried to keep it cool. “Yes, Momma?” He bit back a grin, walking up to this goddess in an apron.

  For a man, she was rather short and fine-boned, and as he approached her, excitement shot into his veins. Momma watched him, picture-perfect in her stripy dress and with a light flush to her cheeks.

  “Have you no shame, Michael? Saying such things to your momma?” she whispered and grabbed his ear, tugging him lower by it.

  Uh-oh. So they were down to full names. This was either going very well, or very badly. Hopefully both. “Sorry!” But he laughed, playing along, more excited by the second. Getting a hard spanking from a beautiful lady has always been number one on his list of kinks.

  Her blue eyes opened wider, and she backhanded him without much force. “Is this funny to you? Unbelievable! I want you to drop your trousers now!”

  Their eyes met, and it was as if thunder rolled through the house. Were it real, it would have made all of Momma’s porcelain poodles drop to the floor. There was silent communication between the two of them, and he could hardly catch a breath from the intensity of it. “Yes, Momma…”

  He turned to face the sink and unbuckled his belt. When he took too much time, Momma tapped her heel against the tiles.

  “I’m waiting, Michael.”

  Mike closed his eyes, indulging in the moment, but then shoved his trousers down to his knees. He’d worn his classy white Calvin Kleins, since he’d been hoping to get some action. It seemed like either way, he would.

  Momma exhaled in anger. “Look at that. Buys expensive underwear to impress all the girls but there’s not enough money in the house for a new washing machine. I cannot believe I raised you like this.”

  Mike’s cheeks flushed, and he put a lot of work into not breathing too loudly just yet. This was so weird. And so hot. He flexed his buttocks. “I’m sorry, Momma.”

  “So many years of hard work, and this is how you repay me? I will show you what I think of your transgressions, young man,” she exclaimed, walking off to a large cupboard.

  Mike’s head clouded with hot vapour that might have consisted of Momma’s perfume, because he was so enchanted he’d nod at anything she’d say.

  “I didn’t mean to be rude, Momma.” His voice came out hoarse, but when she picked up a carpet beater with her slender hand, his knees might have gone soft.

  “Words, words. You are a magician with them Michael, and your friends might fall for all the sweet lies. But not me, Michael, not your Momma.”

  The beater brushed against Mike’s buttocks gently, prompting him to lean forward, escaping the wicker implement.

  Mike huffed, unable to think with his brain so scrambled, and a raging erection already straining the front of his briefs. He could only apologize so much. Now, it was time to take his punishment. He braced himself against the sink.

  “Good boy. Lower your head,” Momma instructed, rubbing the beater over the back of Mike’s thighs before delivering the first strike. It was gentle and didn’t really hurt, but the shock of it made Mike bite his lips. Once the next one came, with a swish loud enough to imitate the wind, he pulled back as the pain spread around the pretzel-shaped pattern at the head of the beater.

  “I need you to understand this is for your own good,” she said as the steady flow of swats continued, making him squirm in place and grip the sink. “No son of mine will be catcalling ladies in the street. Is that understood, Michael?”

  The slap of the beater delivered after that made Mike yelp. There was some proper strength in Momma’s slim hands, and fuck if Mike didn’t love it. She was a woman in power, and yet with a dick to put him in his place. Was she hard under all those petticoats?

  Another harsh swat brought him back to reality where pain exploded under the skin.

  “I don’t hear you, Michael!”

  “Y-yes, Momma.”

  “What will you never do again?”

  “I will never catcall ladies, Momma.”

  “Good, and now take down those showy underpants. I need to make sure that my message sinks in.”

  Mike swallowed and sucked cool air into his burning lungs. The movement of fabric came as a shock to his battered ass, but he did as he was told and pushed the Calvin Kleins halfway down his thighs. He moaned when Momma moved behind him, and the long skirts brushed his bare flesh in passing. He spread his thighs wider and shut his eyes, holding on to the old-school sink, ready to be mastered.

  On bare skin, the beater was like a bite taken out of his flesh, and the swish of the upcoming smack--like the growl of a lioness about to chew through Mike’s flesh. The movement of air had his balls pulling closer to his body each time. He was torn between the illogical fear for his family jewels and the visceral need to expose himself, to entice Momma’s dick with his snug asshole that was already pulsing with anticipation.

  “It hurts too much, Momma,” he whined, squirmed, but stayed put, with his thighs parted.

  Dominate me. Fuck me. Show me my place.

  “And so. It. Should,” Momma said, delivering blow after blow until Mike couldn’t even keep his body still, trembling and rolling his hips between the sink and Momma’s cruel hands. So sweet in her dress, so pretty, such a good baker, and yet she beat him harder than any of his past mistresses. She had no mercy for him at all.

  There was something about this kind of punishment that kept Mike coming back for more, hungry like a dog whenever the time between spankings stretched too much.

  He bent over the sink, panting, hot-cheeked and with a dick as hard as ever. When Momma dragged her long nails over the aching skin of his arse, he actually whimpered.

  “I’m so, so sorry, Momma. I truly am. I will come back tomorrow and fix those bushes,” he whined.

  “There. That’s true remorse,” she said and hit him so hard he couldn’t keep a scream in and howled, briefly losing his balance and falling forward.

  His head spun, but the force pulled on the thread of his need and coaxed it to the surface, leaving him with a twitching dick and an asshole that longed to be filled. He didn’t care how big Momma’s cock was. He just wanted it inside him, her skirts teasing his bruised skin while their bodies clashed over and over.

  He heard movement to the side, and when he pried his eyes open, he saw Momma’s elegant hand putting down the carpet beater.

  “I know my place now, Momma,” he whispered hoarsely, staying put with his thighs open in invitation. “Would you comfort your boy? Please?”

  She exhaled and gently brushed her fingertips over his battered skin. It was delicious and painful all at once, like the hottest sweet chili sauce. “Oh, Michael. When you’re dressed again, I can comfort you with something nice. How about that?”

  “I need to come, Momma. Don’t do this to your boy,” he used his most needy, pleading voice, looking straight into the blue eyes that were so pretty yet so cruel.

  She watched him with her lips parted, and he saw, not without satisfaction, that she must have eaten most of her red lipstick, biting her lips as she watched Mike’s ass dance for her. “If you come on the floor, Momma will clean it for you. This one time. I know it can be difficult for a boy your age.” She sighed in exasperation, as if this really was a tedious task, but her eyes glistened.

  Mike couldn’t grab his cock fast enough. He turned around, leaned his aching ass against the cupboard that held the sink, and rubbed against it as he furiously jerked off, straight onto Momma’s black and white tiles. His cock was rock-hard in his hand even seconds after he’d come. He was a panting mess, but Momma watched his undoing without blinking.

  She ripped off two pieces of a paper towel and gingerly lowered herself right in front of him, wiping the cum off t
he floor.

  “At least we know you’ve got a healthy appetite in those matters,” she commented before dumping the towels into the bin.

  Mike had no framework to comprehend what was going on, but he didn’t even care. He slowly pulled his trousers up, spent, happy, and cleansed of the guilt of having made her uncomfortable with the catcalling in the first place. He now realized just how wrong it had been. A lady like Momma deserved respect, not dumb comments.

  “Every day, Momma. Sorry you gotta do all that extra laundry because of me.”

  She toyed with her belt, staring at him with an unreadable expression before clearing her throat. “It’s late. Maybe you should get ready to sleep if you’re working tomorrow.”

  Mike stepped closer, enticed by her perfume, as if it physically tugged by his collar. She was so small, and yet had so much authority. He fucking loved it.

  “Next time you can fuck me,” he whispered, never breaking eye contact. “I love penetration. I’ve mostly been pegged, but it’d be hot to take Momma’s dick.”

  Momma swallowed, standing stiffly in front of him, hands tapping her stomach. Eventually, she smiled. “As tempting an offer as this is, I must decline.”

  Mike nodded, taking his time to process that. “You want me to do the fucking? Help your son with his growing teenage libido?” He stroked his knuckles over her apron. This time, Momma took a step back, escaping his touch. She clasped her hands at the front of her chest and cleared her throat.

  “Listen, we might have gone a bit overboard here. I enjoyed giving you the punishment, but I’m not comfortable with sex with someone who isn’t my partner.”

  Mike stayed put, knowing that his size could be overwhelming even to the most dominant of ladies. “I’d love to have a thing with you.”

  Momma took a deep breath and exhaled. “I’m flattered, but I don’t do things, Mike. I’m a relationship kind of gal.”

  Mike groaned and wrapped his arms on his chest. “You can’t cocktease a man into a relationship. That is so unfair.”

  “I beg your pardon? I never set any expectations of being in a relationship with you. This is just not the way I do things. As dashing as you are, I just met you.”

  Mike’s arse throbbed with red hot disappointment. “So what? We have to go on three dates or something? Old-fashioned way?”

  Momma shook her head and pointed toward the door. “Goodnight, Mike.”

  Mike huffed, but there was no point arguing this. At least she’d let him come. He bet she wore all those petticoats to hide just how excited it had all made her.

  “‘Night.”

  He walked out with extra swagger, to show her just how much he didn’t care.

  At all.

  Fucking bullshit.

  He hadn’t even stolen any biscuits for later.

  He was not getting roped into courting this insane retro creature just because she knew how to give a good whacking.

  He wasn’t ready to commit to someone and be responsible for them and all that. He was only thirty-two, for fuck’s sake.

  And yet when he sat in the driver’s seat of his Toyota, the insistent throbbing reminded him of just how hot the spanking had been. And the type of role-playing that had organically developed was both confusing and so fucking hot he could barely handle it. She’d managed to get him in a headspace where she had complete power over him.

  When he drove off, he glanced to the inconspicuous house once more, and he saw Momma skittering behind the curtain.

  No.

  Just no.

  Chapter 3

  Mike couldn’t get Momma out of his head. Even when the redness and bruises on his arse faded, he found himself fantasizing about her hands--larger than the average woman’s and yet so perfectly manicured, with long nails that could scratch him until he bled. Before meeting her, he’d thought of himself as heteroflexible and had had experience with transvestites, transwomen, and even a few men, among the usual fare of cis women, but he couldn’t remember anyone affecting him quite like this.

  It had to be the contrast between her feminine old-fashioned behaviour and the strict punishment that had turned him into a wreck. Several times since, he’d found himself driving by her cottage, in hopes of spotting her tending to the garden, but with zero success.

  His mates at work teased him about the fact that he’d been invited to her place to ‘trim her hedge’, but he hadn’t exactly told them the whole story. He’d even slapped the back of Dave’s head when he suggested she was a cougar. Because Momma deserved respect.

  To find a woman willing to take such ultimate control of him had always been a turn on, but people rarely fit the bill, whereas Momma lived this full-on lifestyle. He’d even toyed with calling the number on Momma’s card to commission a dress ‘for his sister’, but she would have seen right through him.

  Restless, he decided to spend his lunch break alone and drove to the largest local supermarket to get himself a meal deal and eat it in peace. With a chicken salad sandwich in the basket, he progressed to the fridge containing drinks and contemplated them when something bright yellow passed down the aisle visible between two rows of shelves.

  The smell of perfume hit him like a splash of cold orange juice, and he knew it was Momma before he even saw the ginger updo tucked under a fascinator. Was it stalking if they just happened to be in one place by accident? Surely not.

  So Mike followed.

  He stuck his head from behind the shelving unit, and there she was—casually walking down the aisle in brown high heels that had some kind of pattern, her skirts floating gently as she moved ahead with that delicious wiggle to her hips. He didn’t even know when he’d started following her scent, eyes focused on her shapely back and the petticoats that hid her figure.

  He couldn’t explain why, but he didn’t actually approach her either, at some point leaving his shopping behind and making sure he remained unseen.

  He wasn’t the only one to stare. Eyes swept over her colourful form, so out of place in the gray walls of the modern supermarket, among all the cheap plastic and loud packaging. It was as if she’d stepped out of a different, better world to grace Sainsbury’s with her charm.

  She was careful choosing her groceries and spent lots of time in the home baking section before heading off to the area that contained clothing.

  Mike could only imagine what glorious biscuits and pastries she’d bake with the flour and sugar she’d selected. And she’d chosen some classy organic butter too. A part of him itched to offer his help with the basket that by now was likely heavy but then wouldn’t that be creepy? Or would it? It would have been a favour to a person he knew. Nothing weird about that.

  Momma passed through the registers making conversation with the cashier and headed off, leaving Mike with his tongue so dry only that tea she’d made for him could have satisfied his thirst.

  He ran, following the canary yellow beacon all the way outside. She didn’t see him yet, dragging two jute bags with both her hands. At least she was wearing gloves to protect those gentle fingers.

  “Let me help with that,” he said as he rushed up to her and grabbed one of the bags, using the opportunity to touch her hand. From up close, the scent of her perfume hit him hard, but he stayed still, catching the shopping when she rapidly let go of it.

  Momma stepped back, her eyes wide as she focused on him. “Oh, it’s you...”

  “Sorry, did I scare you?” He gave her his best smile, pretending he hadn’t gotten kicked out last time for throwing a big baby tantrum.

  She pursed her lips and held the other bag at the front of her body with both hands. It too pulled her to the ground, obviously containing some heavy items. “It’s not polite to just grab people’s things. You could have been after my purse.”

  And there she was again, with that stern fifties mum act. Mike was getting hot under the collar already. “Nah, just wanted to help. Those bags look too heavy for you, Momma.”

  She licked her lips, which we
re deliciously pink this time, as if she’d just had a whole bowl of raspberries. “I can take care of myself, young man.”

  “Let me just take them to the car for you?” He held out his hand for the other bag. She wasn’t rushing away, and that meant she didn’t actually mind his presence. Mike just needed to put himself in her periphery for long enough, and she’d crack.

  Momma studied him for several moments but eventually handed him the bag. “I am only doing this because I believe in gentlemanly manners.”

  He nodded and let her lead the way. “That’s me. My lad days are long time gone.” That holiday in Magaluf a few years back? Never again.

  Not just because only Dave had gotten some throughout the week.

  She shook her head at him and led the way through the car park. Mike knew where they were heading the moment he spotted the mint green exterior of a beautifully restored Ford Anglia.

  “Are they now? I hope it’s not only your Momma you’re treating with respec--” she stopped when a young bald guy in a tracksuit stuck his head out of his own vehicle across the car park aisle.

  “Hey, mate! Are you blind? It’s a tranny!”

  “Yeah, run while you still can,” his friend joined in, both of them in fits of laughter, as if they hadn’t ever seen anything funnier.

  Momma sighed in exasperation and shook her head at them. “How about you mind your own business?” she asked and opened the trunk of her car with the key.

  A red hot volcano of fury erupted in Mike so violently he couldn’t wait to spew lava at the fuckers. No one was gonna speak like that to his Momma!

  He dropped the bags into the trunk, and turned around to them in an instant. “You got something to say, shitstain?” he walked their way with his shoulders tense and his fists craving violence. Oh, well. Maybe he wasn’t over his Magaluf days after all.

  “Just a fair warning, man,” the bald idiot laughed.

  Mike walked up to the car and looked down at the asshole, grabbing his side mirror. “My warning to you is that you better get the fuck out of here, or I’ll wreck your fucking car. Worth more than your teeth.”