Stepmother Knows Best, Pt. 1 (Patreon)

DISCLAIMER: This story contains diaper usage, humiliation, domination, crossdressing, masturbation/diaper sex, and other ABDL themes. I hope you enjoy!

Commissioned By: Anon

-------------------------------------------------------------

*Clink!*

“Mmmmmm…that’s delicious!” said Rachel as she let the subtly sweet flavor linger on her tongue. Raising the teacup to her lips again, she took in the heavenly aroma before taking her second sip, “If I’m not mistaken, I believe I taste black tea vanilla and…coconut.”

Nodding her head with a pleased expression, Deloris was thrilled by how far Rachel had come in her tea education. “Spot on, Rachel! Today’s tea is Orchid Vanilla Tea, which is a black tea infused with coconut and vanilla,” she said, lifting her teacup to Rachel as the two toasted Rachel’s acquired prowess.

If you had asked Rachel to tell you the specifics of whatever fancy tea she’d been served only six months ago, her answer would’ve been a blank stare and a passive shrug. That all changed when the 40-year-old former dress shop owner fell in love with and married a wealthy film executive. Tossing away the grind of owning a small business for the lifetime of luxury that came with marrying a billionaire, she’d found herself as a tiny fish surrounded by the viciously endless pond that was “the upper class.”

Thankfully, Rachel was lucky enough to have been carefully guided in the ways of affluent behavior by Deloris, who was a legacy member of the Hollywood elite. Descended from a long line of filmmakers, she’d made her name as the lead make-up and hair stylist on numerous major motion pictures, bagging multiple Oscars over her illustrious career. Known as one of the friendliest people to work within the industry, it’s no surprise that she and Rachel immediately hit it off when Rachel moved into the mansion next door with her new husband, the two women bonding over their love of femininity. Having no siblings of her own, it didn’t take long for Rachel to fill that void in her life, becoming the younger sister she never had.

“More tea?” said Deloris in a mockingly regal voice, offering the fine-china teapot forward to Rachel.

Holding up her glass to the teapot’s spout, Rachel graciously accepted a second serving. “Why thank you,” she said, mirroring the refined accent that Deloris was using, causing the two women to giggle in unison.

“Ugh! Do you two have to do this every day?!”

Rachel’s joyous laughter came to an abrupt halt as the prickly stem of her rosy new life reared his ugly head. “Like seriously, don’t you have anything better to do than gawk over this same girly shit? Get a life,” said Ryan, Rachel’s “loving” new stepson.

Raised as a member of the wealthy elite from birth, Ryan had entitled and cocky as one would expect a spoiled brat who’s only gotten everything he’s ever wanted might behave. Unlike Deloris, he was far from receptive to Rachel’s arrival, viewing her as no more than just another gold-digging floozy looking for a meal ticket. Beyond the judgment he held for Rachel’s financial status, he also had a deep disdain for how overtly feminine she was with him having grown up idolizing his father’s inherent masculinity.

Sinking in her chair, the last thing Rachel wanted to do was make waves with her father’s temperamental son. “I’m sorry. We’ll be done by two, I promise,” she said, forcing a smile.

“Good. I’ve got Sara coming over then and I don’t want you two turning the whole house into a lame fest,” said Ryan, walking away feeling good after having the final word. As much as he hated the way his stepmother oozed femininity, it only made her weak in his eyes. With how much of a pushover she was, he often fantasized about her being so desperate to please him that she’d offer to suck his cock on a daily basis. While the thought was tantalizing, he lacked the cojones to ever demand something like that, only able to dream about a scenario like that.

“What a sniveling twat,” said Deloris, appalled by Ryan’s nasty behavior, “You really shouldn’t show your neck and apologize like that. He’ll never take you seriously if he thinks you’re too meek to fight back.”
Placing her head in her hands, Rachel was so frustrated by the constant mockery she received from Ryan that she felt like she could cry at any second. “I just don’t know what to do anymore. Do you think I want to let him “alpha male” his way into getting everything he wants? I’ve tried everything and it’s never enough. How could the kind and caring man that I married raise such a cruel son? It’s like he has blinders when it comes to Ryan,” she said, blowing her nose into the silk hanky at her side.

“It doesn’t surprise me that Daddy’s pride and joy never got the discipline he’s had coming to him for a while now. If he was my kid, I would’ve dropped his pants and spanked him right here and now. I don’t care how old he is,” said Deloris, angrily sipping her freshly poured tea before recoiling from the steamy cup, “Mhmm, too hot.”

Sighing, Rachel let her undignified sideshow as she placed her elbows on the table and leaned her chin against the backs of her knuckles. “I’m so jealous of you. You have three lovely little daughters while I got stuck with a man’s man for a son,” she said, scrunching her face into a pout as she allowed her mind to wander, “What I wouldn’t give for Ryan to have been born a girl.”

Lightbulb!

Sitting upright, Deloris's brain was suddenly set ablaze by Rachel’s passing comment. While she’d never acted on it or even told anyone about it, Deloris had always harbored a deep, seemingly-unattainable fantasy: to take a quote-unquote “alpha male” and turn him into a prissy little girl for her own amusement. She’d stay up late fingering herself to fictional stories of men being put in their place as they fell into permanent feminization, dreaming about the prospect of putting her hair and make-up skills to good use and transforming them into a quivering sissy. With the deeply-held belief that everything happens in life for a reason, she truly believed that was the chance she’d been waiting for her whole life. “Hypothetically, if we could make Ryan into a girl…would you want to?

Stopping mid-gulp, Rachel paused as Deloris’s fateful words began to take root in her mind. For a brief moment, she pictured Ryan dressed up in one of the frilly gowns she used to labor over, the thought causing her to snicker. “Hypothetically…” she said as she and Deloris stared into each other's eyes knowingly.

“Yes…hypothetically…” said Deloris, nodding to Rachel with an ear-to-ear grin growing on her face as she raised her teacup to her lips, “Ah, still too hot.”

-------------------------------------------------------------

“What the actual fuck?! That was a fucking headshot, you cheap fucking game!” shouted Ryan, slamming her fist on the desk in a flash of aggression. His leg began to bounce impatiently as he waited for the respawn timer to tick down.

*KNOCK KNOCK!*

Inching Ryan’s bedroom door open, Rachel gingerly poked her head in. “Um, hey, Ryan, you got a minute?” she said, powering through the anxiety that was telling her to turn and run.

“Shhhjhhjhsh!” shouted Ryan as he focused back in on his game. For the next two minutes, he played out the rest of the match without saying another word to Rachel, culminating in a glorious comeback victory by the end. Slamming his fists on the counter in victory this time, he jumped up from he said and screamed, “WOOOOO! GET FUCKING REKT, KID! DID YOU FUCKING SEE THAT SHIT?!” He looked back at Rachel and gestured to his accomplishment, too amped to hate on his stepmother for once.

“That was…quite something,” said Rachel, having no clue what on Earth just happened in his game despite watching over his shoulder for two whole minutes, “Listen, I wanted to apologize for earlier. Deloris and I have agreed to move our tea time to her house from now on so we won’t disturb you. Oh! And I’ve got some cookies cooling on the stove downstairs to make it up to you. Wanna join me for some?” In the back of her mind, she prayed that she hadn’t rambled through her rehearsed dialogue too quickly so as not to tip him off that something was up.

Mercifully for Rachel, Ryan thought nothing ill of her offering, instead letting a smug expression sink into his face as he believed this was finally trying to kiss his ass like she should’ve been doing this whole time. Exiting the cue for his next match, he got up from his desk and stretched his arms, taking his time before responding, “I suppose it couldn’t hurt. Hopefully, you’re a better baker than you are a decorator.” He smiled wickedly, watching for any sign of reaction from Rachel over his dig at the updates she had made to his father’s house.

However, Rachel remained stone-faced, biting down hard on the inside of her bottom lip to keep from flinching. She could taste the small amount of metallic blood leaking onto her tongue and washing away the delightful flavor of her tea. As annoying as the pinch of pain was, it was all worth it to keep from letting Ryan get to her again. “Excellent. They should be finished cooling so let’s head on down,” she said, leading Ryan out of his room and down the hall toward the stairs. As she reached the staircase, though, she stopped and lowered her posture before turning to look at Ryan with pleading eyes, “Actually, before we head down, would you mind doing a small favor for me? There’s this box that the movers placed on a really high shelf in my closet that I’m neither tall enough nor strong enough to get. I would be super grateful if you’d help me out.”

Cringing at the thought of entering his stepmother’s ultra-fem walk-in closet, Ryan backed away, breathing in sharply through his gritted teeth. “Err…I dunno,” he said, raising both hands as if he could physically push away the idea, “If it’s all the same, I rather not-”

“Ah, darn, I figured you wouldn’t want to. Your father wouldn’t step foot in there either. If you ask me, it’s one of the few moments he’s ever appeared unmanly to me. I’ve never understood why men make such a big deal about a bunch of fabric. Don’t worry about it, though. Just forget I said anything and let’s go have some cookies,” she said, waiting for the inevitable as she turned to head downstairs.

Before Rachel could even take her first step, Ryan grabbed her by the arm. “Well, hold on now. It’s really no big deal to me. I uh…just didn’t want your cookies to get cold. If it’s only one box, it should be a problem,” he said, taking advantage of an opportunity to outdo his dad while simultaneously impressing his stepmother with his masculinity, “Lead the way!”

Traveling through the master bedroom, Rachel and Ryan entered a room that could only be described as the peak of feminine luxury. How a space this massive could ever be considered a closet was pure nonsense. It looked more like a high-end clothing boutique than someone’s personal wardrobe. There were rows upon rows of every type of female clothing imaginable, with an entire wall dedicated to shoe storage. Despite all the glitter fabrics and shiny shoes glimmering under the studio-grade lights, it was the solid gold vanity that stood out the most; its grand design and elaborate detail work being something to truly marvel at.

“Ugh! It looks like a spoiled princess threw up in here! There’s no way you could ever wear all of this useless crap!” stated Ryan, disgusted by the feminine opulence and the flowery scent that permeated the closet.

Brushing Ryan’s rude comment aside, Rachel simply shrugged. “It may seem silly to a strong man like you but there’s something so comforting about being engulfed by femininity,” said Rachel as she pointed to a massive department store box stashed high up on a shelf stationed above a rack of fur coats, “It’s that box right over there.”

Cracking his knuckles, Ryan readied himself to step up to the plate. “I’ll get that down, no problem,” he said confidently, hopping up on his tip toes as he reached up to grab the large, white, and pink box.

However, right as Ryan was about to pull the box down, Deloris stepped out from behind the rack of coats, surprising him with the self-defense spray that she kept in her purse at all times. The spray worked quickly, its sensory-depriving inhibitors causing Ryan to crumble onto the fluffy carpet. His vision became fuzzy and his hearing began to dampen as his stepmother and her tea buddy stood over him.

“Seriously, best $40 I’ve ever spent. Get yourself some. It works so much better than pepper spray,” said Deloris, tucking the self-defense spray back into her purse.

Kneeling next to Ryan’s limp body as his eyes slowly started to shutter, Rachel pinched his cheek and offered him a warm smile. “See you when you wake up, pumpkin,” she said, her words being the last thing Ryan heard as he passed out.

-------------------------------------------------------------

Ryan’s lip twitched, feeling a series of something light like a feather brushing against his cheeks. He contorted his face, trying to scratch the itch that just kept moving around on his face like a bug. Oh Goddess, please don’t let it be a bug. He went to wipe away whatever was ticking his face but found that he was unable to move his arms. In fact, after a brief moment of struggling, he discovered that he couldn’t move any part of his body. Even though his eyes were closed, he could tell he was sitting upright, making the lack of mobility even odder. Though, the oddest thing of all was the feeling of tight, smooth fabric hugging his torso from his chest all the way down to his hips. He didn’t know what was going on but something in his gut told him he was in danger.

“Oh, I think he’s finally.”

“Hehe, now the real fun begins.”

Instantly, Ryan recognized the voices of her stepmother and her tea party friend. All at once, a rush of memories filled back into his brain, recalling that he’d accompanied his stepmother to her walking-in closet before everything went dark. Sniffing the air, he could still smell the floral scent that wafted through the air, so he had to still be in the closet. That’s when it hit him. That crazy tea lady had sprung out of the collection of animal skins and blasted him in the face with something that made him pass out. It was no longer just his gut telling him that danger was present.

Opening his eyes, Ryan was greeted by the piercing studio lighting that made up Rachel’s closet. As his eyes adjusted, he saw a strange girl he had never met before sitting across from him wearing nothing but lingerie. From the nose down, she had perfect, ruby-red lips that shined against the flattering lights, with a plethora of foundation and contour caked on to soften her chin and jawline while accentuating her cheekbones and petite facial features. Meanwhile, her eyes were still having work done, with the peachy eyeshadow being left half-done. “I’m sorry, do I…” he muttered, raising an eyebrow in confusion as the girl across from him moved her mouth at the time he did. As he did so, the girl raised her eyebrow as well, mimicking him once again. After a few more seconds of staring, it finally clicked, “W-What the FuCK IS GOING ON?!”

Looking down at his body, Ryan began frantically pulling against his restraints as he gazed upon the same lingerie that he had seen in his reflection. Pathetically, he snuck another glance at himself, slightly amazed but also horrified by how much like a girl Deloris had managed to make him look. “Untie me right fucking now! You think my dad will stand for this?! Your ass is going back out on the street where he found your money-grubbing ass,” he said, thrusting his height upward and causing the chair to bounce in place.

“Oh, you think so?” said Deloris, crossing in front of Ryan and stepping over his legs to straddle them. She made sure to tease him a little, wiggling her butt on his pointed lap as she settled into place on his thighs, “Because what do you think he’s more likely to believe? That your new mother and I overpowered you and forced you to dress up like this, or that his sissy son snuck into Mommy’s closet for some private dress-up time? If you ask me, one of these seems far more plausible than the other.”

Left in stunned silence at how bold Deloris was acting, Ryan’s eyes darted to Rachel’s reflection, hoping that his stepmother would reign in her far more domineering friend. Sadly, she did nothing more than flash him the same sadistic smile that Deloris was sporting. Realizing he’d never be able to intimidate them into letting him go, he lowered his head and began sniffling, “P-Please let me go. I promise I w-won’t say anything,” he said, hoping to appeal to a woman’s kind heart.

Sadly, there was no kindness to be found. “Oh, don’t worry, we fully intend on letting you go…so long as you play nice with us girls, that is,” said Rachel, showcasing a much more confident attitude now that she didn’t have to bend over backward to please her misogynistic stepson as she let her arms drape over Ryan’s shoulders. She slowly ran her finger softly along his chin, relishing in the sheer feeling of his freshly-shaven face, “If you sit still and let us finish our makeover, we promise to get you back into your old clothes before your old man gets home from work. However, if you keep being lippy with me and your Aunt Deloris, then we’ll have no choice but to leave you like this for your father. Do we have an understanding?”

As much as Ryan wanted to tell Rachel and Deloris to go fuck themselves, he knew there was little choice so long as he didn’t want to tarnish the manly image his father had of him. Shakily nodding his head, he stuttered out a small, “yes,” sealing his feminized fate.

Given the green light from Ryan, Deloris resumed her work as she added a heavy dusting of eye shadow. Not that she needed a green light, per se. It was more of a courtesy than anything. “See, it’s not so bad, right? Plus, it really brings out the blue in your eyes. All the boys are going to be hypnotized by your beauty,” she said purely for her own satisfaction.

Groaning from behind his pouty expression, Ryan had less than zero interest when it came to attracting guys. As much as he hated to admit it though, Deloris was right. Each time he caught sight of himself in the mirror, a tiny flutter filled his heart, one not too dissimilar from the feeling he got when looking into Sara’s dreamy eyes.

As Deloris put the cap back on the peach eye shadow, Ryan hoped that this would mean an end to his make-up session. Sadly, the eye shadow was only the beginning. Next, came eyeliner and mascara, both of which put quite a strain on his eyes as he struggled to keep his eyes from watering. Not that it would have mattered since Rachel was quick to comment, “Tears of joy over finally seeing the real you? Go ahead and let it out all you want to. Your make-up is waterproof for a reason.”

Following the eye torture that came from the pitch-black products, Ryan was introduced to perhaps the most unique form of agony that he’d ever been subjected to. “Now, hold very still. I don’t want to prick you,” said Deloris as she brought a pair of tweezers close to Ryan’s eyebrows. He wanted to protest but it only took a single time of him flinching and being stabbed by the sharp point of the tweezers to keep him still. Every hair that was pulled from the pair of fuzzy wigglers over his eyes was akin to going through Chinese water torture. By the time his first eyebrow was finished, he didn’t even care how feminine he looked. He just wanted Deloris to finish as fast as possible.

Plucking the last tiny hair from the far side of his left eye, Deloris stepped back to get a full look at his face, a malicious smirk growing on her face. “Goddess, I am good. I don’t even think his father would recognize him now,” she said, prompting Rachel to join her in admiring the rebirth of her new stepdaughter.

“Heck, I don’t even recognize him and I watched you do it!” shouted Rachel as both girls fell into a fit of giggles.

As the ladies laughed, Ryan could only grimace at his reflection, not wanting to see what had become of him but also unable to look away. As Deloris moved back in and began spritzing a setting spray on his face, he could actively feel the grip he had on his masculinity slipping. To make matters worse, the silky fabric and constant humiliation in combination with seeing his new form completed caused an unfortunate chain reaction in his loins. Feeling the tingling sensations creeping throughout his shaft, he bit down on his tongue hard, hoping to quell his heightened arousal.

Tragically, Ryan’s efforts were all for naught as Rachel got sight of the tiny point sticking out of his satin and lace panties. She quickly rushed over to Deloris, who was halfway through her finishing touches on Ryan’s make-up and whispered into her ear.

The two girls began laughing once again, causing Ryan’s heart rate to elevate and, in turn, his hard-on to pulse slightly faster. “What devious scheme were these two planning now?” he thought, far from excited to find out the answer.

Stepping out of Ryan’s direct line of sight, Rachel reached into her pocket and pulled out a small remote. From the second she and Deloris had gotten Ryan fitted into lingerie, she’d been chomping at the bit to reveal the big surprise to her stepson. And now that he was properly stiffened, it was the perfect opportunity to further shove him down the path of permanent sissification.

While Ryan assumed he was just wearing regular-degular lingerie, the truth was far more sinister thanks to the Valentine’s Day present that his father had bought for Rachel only a handful of months prior. Wrapped delicately around Ryan’s waist and prodding pecker was a pair of remote-controlled vibrating panties with five glorious settings to bring any good girl to her knees. With her thumb on the remote, she made sure to watch every inch of Ryan’s body for a reaction as she clicked the vibrator on.

*bzzzzzzzzzzzz*

An instant shiver was sent up Ryan’s spine before spreading across his body in a series of chills. His eyes went wide and his lip started to quiver as the low rumble of his vibrating panties worked to egg on his cock’s growing need for attention. And the attention he did get as Rachel stormed back up to him and cupped her hand tightly around his dick and balls, increasing the sensations felt from the panty’s internal vibrator. “Your dad was so nice to buy me these but they're not really my style,” she said, wiggling her fingers on the underside of Ryan’s testicles as her palm brushed against the head of his penis, “Do you think your father ever would allow me to put these on him? Of course, not. But you don’t need to worry about that anymore since you’ll never be the man he is.”

It was all too much. The ceaseless vibrations of the panties. The aggressive tightness of his restraints. The sheer sensuality of his silky lingerie. The cruel taunting from Rachel. The overwhelming feeling of femininity ensnared his heart and soul. All of this added up to send his pleasure receptors well past the point of no return. Rachel had only been gripping Ryan’s privates for thirty seconds, but that was all it took for his cock to start spurting out semen. He uttered a squealing moan as his body convulsed, raptured by the most shameful and glorious orgasm of his life.

Pulling her hand away, Rachel grabbed a make-up wipe and cleaned off the droplets of spunk that clung to her fingers. “I don’t think there’s any way you could argue now. You are officially as sissy as sissy can be,” she said, tossing the used wipe aside and returning to Ryan’s side to stroke his shoulder-length hair, “You sure we don’t want to give him a girlier hairstyle? I agree that the mid-length is good but we could give him bangs or something.”

Shaking her head without looking away from Ryan’s face, Deloris responded, “Seldom few people can pull off bangs properly. Besides, if we cut his hair any shorter, they’ll be less to play with.” The two girls chuckled once again, imagining the variety of precious hairstyles they could give him once the make-up game ended and the dress-up game began.

*DING DONG! BING BONG!*

Suddenly, Rachel, Deloris, and Ryan all froze as a fancy doorbell sounded off, alerting the trio to the presence of a visitor. “It’s not his father. He would’ve just come in,” said Rachel, who wasn’t aware anyone else would be stopping by today.

Ryan, however, was well aware of who was downstairs. A droplet of sweat ran down his neck as he realized this situation was about to go from bad to worse now that his childhood friend, Sara, had arrived for their two o’clock hangout.

TO BE CONTINUED…