Stepmother Knows Best, Pt. 2

“Soggy Sara! Soggy Sara!” 

The cruel chant of a dozen small voices encircled the 10-year-old dressed in a fluffy party dress with a small, yellow puddle growing around her. She squeezed a large, pink teddy bear in her arms for whatever comfort she could get from it. It was her birthday and she had just reached double digits; a momentous achievement for any child. Sadly, her celebration of that accomplishment was dashed when at her birthday party, a little too much fun and a little too much fruit punch led to disastrous results. 

Kneeling beneath an unbroken piñata, tears ran down Sara's chubby cheeks as she waited for her mom to rush over and rescue her from this mortifying scene. All the while, the kids who she’d once seen as her closest friends continued to pile humiliation onto her, especially Ryan, who at this time was also only ten. He and Sara had been best friends since the two of them could crawl, and yet, despite their closeness, he still took the opportunity to laugh along with the rest. 

Looking around at every kid pointing and laughing at her, Sara began taking a mental revenge list. And at the very top of that list was her dear friend, Ryan. 

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DING DONG! 

Now entering her 20s, Sara had almost completely forgotten about the horrible experience that her tenth birthday turned into. However, that didn’t mean such a traumatic event left her without any scars. Even if she couldn’t remember all the details, she couldn’t stand being made fun of or being laughed at for any reason, something Ryan had found out the hard way through years of continuous, yet sometimes strained friendship. If it wasn’t for the fact that her dad and Ryan’s dad were business partners, she would’ve ditched his lazy ass long before now. At least she wasn’t forced to make googly eyes at him, especially with how obvious it was that he was into her. 

Dressed as if she was a mid-2000s punk rock girl who had just discovered Hot Topic, Sara was far removed from her ultra-girly roots. Gone were her days of striving to be a pageant queen, replaced by black clothes and way too much eye shadow. While the transition from fem to goth may have felt natural to Sara, anyone keeping track would’ve seen the dramatic shift in her desire to be feminine happen not long after that birthday party. Not that she ever felt the need to dress up to go to Ryan’s house. 

After waiting for almost two minutes, Sara began to grow restless. “Let’s go, Ryan! You knew I was coming over,” she shouted, bringing her fist to the door and slamming it against the hardwood door. 

Click! 

“Heyhey! Sorry about-EEEP!” said Rachel, lurching back in shock as her face came within inches of meeting the business end of Sara’s fist. 

Retracting her hand so soon as her fist swung through where the door should be only to see a milfy, middle-aged woman in its place, Sara leaped back after narrowly avoiding knocking the block off her best friend’s stepmom. “Oh, my Goddess! I’m so sorry, uh…Rachel, right?” she said, a bit exasperated. 

Laughing off her near-death experience, Rachel nodded. “Yes, Rachel, yes. That’s…me,” she said, her mind still reeling from how close she came to being punched for the first time in her life. Gathering her thoughts as quickly as possible, she knew she needed to get Sara upstairs promptly, “Um…inside…you…ugh! Sorry! Would you like to come inside?” 

Chuckingly under her breath at Rachel's word salad, Sara welcomed the arbitrary invitation and stepped inside. “Thanks and sorry again,” she said, making a B-line straight to the living room, discovering that the TV was turned off and Ryan was nowhere to be found, “Hey, where’s Ryan? We were supposed to watch the Chargers game together.” 

Sashaying over to Sara in a forced-casual manner, Sara placed an arm around Sara’s shoulder, “Why don’t you join me upstairs for a sec? I’d be happy to show you what Ryan’s been up to.” Ushering Ryan’s lifelong friend upstairs, she placed both hands on Sara’s shoulder in a comforting way. “I will ask that you keep an open mind. Ryan’s going through something of a transformation right now and he needs all the support he can get.” 

“Um…okay?” responded Sara, too confused by whatever Rachel and Ryan were doing to even question it. Her confusion only grew as she was led through the master bedroom to a closet door she’d never entered before. Though, as Rachel opened the door, her confusion instantly melted away, replaced by stunned amusement and a slack jaw. 

“OW! G-Get off me!” shrieked Ryan, trying and failing to wiggle his head free from Deloris’s grasp. Unfortunately, his neck muscles were nowhere even close to strong enough to shake off an entire person. 

With several lengthy extensions in hand that matched Ryan’s hair color almost too perfectly, Deloris continued to stick the strands of fake hair to her subject’s pretty little head. “Oh, pipe down! Girls have to do this stuff all the time,” said Deloris as she clipped another extension into place. Noticing the door opening in her peripheral vision, she looked up and smiled at Rachel and her guest, “Oh, good! You’re back! I went digging through my bags after you left and found a bunch of hair extensions that were too good not to use. You did say you wanted him to have a girlier hairstyle.” 

Seeing Sara’s reflection in the mirror, Ryan’s thrashing efforts doubled. “N-NO!! Sara! Don’t look!” he screamed as he felt whatever small chance at a future relationship with his childhood bestie disappear like the sands of time. Having already been doted on enough by his stepmother, bringing his near-lifelong crush into this whole situation was like a wet dream but in reverse…a wet nightmare if you will. 

Covering her mouth with her hands, Sara was at a loss for words. Even at the best of times, Ryan wasn’t the most masculine of guys. But even then, she never once pictured him gussied up with big hair and a slathering of make-up. “Wowie, Ryan. That’s uh…quite the look,” she said, struggling to restrain her laughter with every syllable. 

“Please! Just make them stop!” begged Ryan, hoping that the arrival of his best friend would bring an end to Rachel and Deloris’s fun, even if it did come at the high cost of letting his crush see him in such a feminized state. 

Before Sara could respond in any way, though, Rachel stepped in between them to put a kibosh to any hope of escaping. “Oh, give it up, Ryan. You’re amongst sisters now,” she said, placing her hands on each of Ryan’s shoulders and squeezing them together lovingly. She then turned back to Sara and waved her over, “Don’t let him fool you. He’d been begging me to do this for weeks. If you want proof, just look at the state of his pretty panties. 

Rounding the chair to get a better look at Ryan’s full ensemble, Rachel nearly exploded when she saw the dripping tip of Ryan’s penis, which was swaddled in a very damp pair of silky lace panties. “I-I think I see what you mean,” she said, dropping to her knees before rolling over onto her back in hysterics. She wasn’t even aware of it at the time but a deep feeling of catharsis had taken a heavy weight off of her shoulders that she’d long forgotten was there. 

“I-It’s not funny!” yelled Ryan, his protests causing the girls’ laughter to raise in volume and intensity. Frustrated beyond a reasonable point, he finally blew up, “FUCK ALL OF YOU! UNTIE ME RIGHT NOW OR I’LL-” 

Grabbing both of Ryan’s cheeks with one forceful hand, Rachel was done with Ryan’s vulgar tongue. “You’ll what, Ryan? Run to daddy to tell him what your meanie stepmom did to you? We’ve already gone over how well that’ll go,” she said, reminding Ryan of what’s at stake should the girls decide to leave him tied up in this state. She allowed a wicked smile to curl across her lips as Ryan’s struggling ceased, “Good girl.” She released her grip on his jaw, giving him two light slaps on the cheek as she pulled her hand away. 

Taking a knee behind Ryan’s chair, Deloris began untying Ryan’s restraints now that his hair and make-up were in place. “We’ll have to wait to style his hair until his dress is on,” she said, still in command of the technical aspects of Ryan’s sissification. With Ryan’s wrists and ankles fully released, she took him by the hand and forced him to stumble across the walk-in closet on shaky legs, “Come on, Ryan. It’s time to get ready for your big day.” 

“B-Big day?” Ryan stuttered as he was moved from his seat at the vanity to an area of the closet with three floor-to-ceiling mirrors organized in a half-hexagon shape. 

Bending down by Ryan’s feet, Rachel placed a pair of three-inch high heels on the floor and gently grabbed one of his ankles. “This is going to be a long process, so do your best to hang in there for us, okay? Normally, brides could take breaks when they need to, but you’re such a big, tough man that doing it all in one go shouldn’t be a problem. 

BRIDE?! Ryan began to feel faint overhearing the word, “bride,” used on him so casually. They couldn’t do something as embarrassing as making him wear a wedding dress, right?! Tragically, it wasn’t long before that question was answered in the form of a massive, poofy ball of fabric being carried into the walk-in closet, followed by another, and another, until half the room was taken up by five white orbs, each one bigger than the last. He wanted to run, to hide, to fight, anything to get out of this. But between the high heels and the threat of his dad finding out, his feet may as well have been encased in cement. 

“Arm’s up, girly,” said Sara, stepping in behind Ryan and pushing his arms up while Rachel and Deloris approached from the other side with one of the puff balls. Before he could even muster the strength to sneak in a final objection, he was sent hurling through a cloud of white fabric. It was only a few seconds but to Ryan, it felt like it took him a hundred years to reach the other side. 

Clapping her hands together, Rachel quickly moved to Ryan’s side to allow him the chance to see himself fully. “This dress took me almost four months of labor to complete. Tell me, how does petticoat number one feel? Are all those girlish emotions hitting you yet? You couldn’t stop looking at me on my wedding day, so I assume this must be a dream come true for you,” she said, snickering as she and the other ladies admired the first step of Ryan’s wedding outfit. 

Standing in place with the mirrors each reflecting a different angle of him, Ryan’s lip quivered as he caught sight of the massive petticoat that was hugging his lingerie-covered hips. He rotated in place slightly as he struggled to stay on his feet, watching with horror as the petticoat followed his every movement; its soft, heavy fabric swishing back and forth in a display of pure girliness.  

As Ryan’s right ankle finally collapsed, he was sent falling to his side, only for Sara to catch him mid-descent. “Hey, now! Can’t have you slack off so soon! You’ve still got three more petticoats and the big dress to go!” she said, enjoying herself immensely as she watched the life drain from Ryan’s eyes. 

For the next hour, Rachel, Deloris, and Sara worked in tandem to fix the rest of the fluffy petticoats to Ryan’s body, observing gleefully as the width of his wardrobe quickly ballooned to seven feet in all directions. By the time the final petticoat had been settled into place, he felt like his lower half had been plopped inside of a hollow cupcake. 

“Almost done! Time for the big finale!” said Rachel as the girls lifted the outrageously heavy, pink satin wedding dress into the air before tossing it over Ryan like a massive, silky comforter. It took many minutes more to push Ryan’s head and arms through their respective slots before they could twist the fabric into place and smooth out the wrinkles, completing his wedding day attire. For Ryan’s part, it felt akin to being trapped in a washing machine as the swirling fabric assaulted his senses, leaving him very disoriented. By the time his head poked through the top, he was seeing double everything around him. 

While the dreadful process of getting the over 20-pound dress over his already bulky outfit may have been, little solace was offered to Ryan’s masculine soul as he stared helplessly at his hyper-feminized reflection. Perhaps the most terrifying thing of all was that he almost couldn’t see himself behind the hair extensions, make-up, and poofy dress. From his perspective, all he saw was a dainty bride waiting for her moment to waltz down the aisle. 

As a finishing touch, Deloris made sure to pin his hair up in a perfect bridal bun before placing a stunning, white veil on him to cap off his darling wedding ensemble. Meanwhile, Rachel went searching through the myriad of boxes she had stored in her closet until she came up for air with a bouquet of fake flowers in her hand to add to Ryan’s growing list of accessories. “Honestly, this may have been more fun than getting dressed for my own wedding!” she declared, earning another round of rapturous cackling from her cohorts. Taking Ryan by the hand, Rachel spun the poor boy around in a semi-circle, making sure to give him plenty of support since he didn’t have his sea legs with heels yet.  

Rushing up behind the duo, Deloris was quick to grab the back of the wedding dress, holding it up so that it didn’t snag on the carpeted floor too much. “As part of the wedding day package, we’re gonna walk you through your wedding day,” said she as she and Rachel began escorting Ryan across the walk-in closet one step at a time, “Just try to imagine your future wedding day and you’ll find how easy it is to move in all this stuff. 

For Ryan’s part, he did his best to keep up with his stepmother and her friend as they inched their way through the closet, stumbling several times thanks to the effect that plush carpet had on high heels. It didn’t help that he was forced to stare at Sara waiting for him at the opposite end of the room much like a groom waiting for his bride would. From the way the silky dress brushed against his arms as they swung to how the wealth of petticoats brushed against his buttery lingerie, it was all too much for him to handle. His face turned redder than a tomato as the damp, sticky panties began to stretch once again to accommodate his reemerging hard-on. 

Feeling Ryan’s grip on her hand tighten and hearing a soft whimper under his breath, Rachel had a feeling that she knew exactly what was going on under all those puffy layers. As they neared the end of the walk-in closet, she reached into her pocket and pulled out the remote for the vibrating panties again, rubbing her thumb over the on-button deliciously. “Now Ryan, the biggest thing for a bride to maintain, under any circumstance, is her composure,” she said teasingly as she pressed her thumb down on the button with vigor. 

bzzzzzzzzzzzz! 

“EEEEEEEEP!” yelped Ryan, his knees instantly going weak as his cock was accosted with the pleasurable vibrations that only his lacey panties could provide. Zap off all his strength, he dropped to his knees, creating a mushroom cloud of silk as the dress poofed out around him. Between the buzzing panties and the swaths of satin he was trapped within, he hadn’t even fully settled to the floor before streaks of murky jizz shot from the tip of his cock, through his tight panties, and onto the innermost layer of petticoats. 

“Well, so much for keeping a lid on your composure,” said Rachel, encouraging even more laughter at Ryan’s expense. She pushed her way through Ryan’s inflated dress to give him a motherly hug,  “How many times has that been today? Two? Three? At this point, we may have to trade those panties of yours out for some pull-ups!” 

Lightbulb! 

Suddenly, Sara was struck with inspiration. “Hey, guys, I need to head out really quick and grab something. Is it alright if I come back in, say….45 minutes?” she asked with so much unfettered excitement that she was talking a mile a minute. 

“Of course! Don’t worry, the fun’s not stopping anytime soon,” said Rachel, her devilish grin sending mixed signals of fear and arousal to Ryan’s fragile and horny male brain. She clicked off his panties, allowing him to relax, if only for a brief moment.  

Still reeling from his latest orgasm, Ryan watched as his only hope of salvation disappeared, leaving him alone again with Deloris and Rachel. Not that Sara had been much help up to this point anyway. Viewing her as an option for salvation was mostly wishful thinking on his part.  

Helping Ryan back to his feet, Rachel and Deloris guided him back to the center of the closet. They then took their time to posture him so that he could stand on his own two feet without falling down again. “Perfect!” said Deloris, slapping her hands together so loud that it caused Ryan and even Rachel to jump a little in surprise. Pulling out her phone, she quickly switched over to her camera, “You’re going to be a good girl and model for us while we take some lovely photos.” 

“Ph-Photos?!” said Ryan, his heart rate accelerating over the prospect of his current appearance becoming immortalized in picture form. He looked at his stepmom, hoping she’d talk some sense into her friend. However, he should’ve known better than to expect empathy from either of them as he watched her pull out a cell phone as well. He wanted to object with all his being but he knew he needed to behave if they were going to help him take all this crap off before his dad got back, “Just p-promise me you won’t post them, okay?” 

“We promise, Ryan. Now, go on and give us a smile. It’ll make you look ten times better,” said Rachel, her condescending tone giving Ryan very little hope that she was being honest. Still, it wasn’t like he had the option not to believe her. Gritting his teeth, he obeyed his stepmother’s request and forced a painful smile onto his face. 

SNAP! SNAP! SNAP! 

As soon as they got the arbitrary go-ahead, Rachel and Deloris showed zero restraint as they bombarded Ryan from all sides with snapshot after snapshot to make sure that every last inch of their blushing bride was captured, including crawling up under his dress from some more “candid” photos. Mercifully, after the ladies had their fill of bridal shots, they began to help Ryan out of his dress, giving him hope that he was near the light at the end of the tunnel. He sighed with relief as the petticoats were removed from him one at a time, letting up on the weight that had been pressing down on him. Sadly, what he thought was light turned out to be nothing but a mirage as the girls wheeled out another dress for Ryan to try on, trading out the ballgown wedding dress for a red, skin-tight evening dress. 

“I hope you like it, Ryan! This was the dress I wore when I met your dad and it worked exactly how it was designed to. He couldn’t stop drooling over how hot I looked,” said Rachel as she and Delories forced the form-hugging dress over Ryan’s head and slid the stretchy material down his body. 

It was all downhill from there as the girls ate up every dress Ryan tried on, gleefully snapping dozens of photos. From cutesy sundresses to leather jumpsuits, he was given a crash course in female attire. For a guy who’d only worn simple male fabrics, every new texture and textile that was placed on him felt like being force-fed the richest foods you’ve ever had in your life non-stop. Unable to process all the feminine feelings that were swarming around him, his body continued to react against his will, causing the panties around his waist to go taut with embarrassing stiffy after embarrassing stiffy and leaving a slime trail behind on the crotch of each outfit he tried on. All the while, he did his best to keep track of the time based on the conversations between Rachel and Deloris, deducing that he only had about an hour before his father came home. If they were going to live up to their promise, then he didn’t have much more torture to live through, allowing him to power through in spite of the neverending shame pageant he’d been made to endure. 

“Hey, guys! Sorry, that took me way longer than I expected,” said Sara as she burst through the walk-in closet doors having a waltz right into the house without even knocking, “I’m so, so happy you guys are still at it. I was worried I might be too late.” She set two large tote bags down on the ground and let out an exasperated breath. 

Leaving Ryan in the midst of getting changed out of a green, velvet cocktail dress, Rachel and Deloris rushed over to greet Sara, as well as find out what goodies she’d returned with during her outing. Left on his own for the first time since he’d entered the walk-in closet, he was afforded the time to scoff at his own reflection. Never, at any point in his life, did he stop to think about what it would be like to wear women’s clothing. And now that he’d been given a first-hand experience, he was happy the thought never crossed his mind. Why did girls demand the most luxuriously soft and silky fabrics if all of their outfits felt like their body was being mangled inside of them? 

And then there was Ryan’s make-up and hair. Thanks to Deloris’s diligent work, his make-up remained perfect throughout each and every wardrobe change. Heck, he could be drenched in sweat in the middle of a torrential downpour and his foundation still wouldn’t run. Whatever crap these Hollywood bigwigs used certainly was the real deal. His hair, meanwhile, had gone through several transformations, from a tight bun for his wedding look to a pair of twin tails for the schoolgirl outfit they’d forced on him; an outfit he could only assume had to be a fetish costume that Rachel wore for his father during intimate bedroom scenes. Presently, his hair and the extensions attached to it had been put into a trendy updo style that one might see genuine model wear in a fashion magazine. It was almost too surreal how a change of hair could feminize someone’s face so much. 

“BWAHAHAHAHA! Sara, you are a flipping genius,” screamed Deloris, rolling over onto the floor in a fit of laughter that brought tears to her eyes. Rachel soon joined in as well, unable to continue digging through the bags from how hysterical she became. 

Hearing his stepmother and her bestie’s vicious mockery sent chills through Ryan’s entire body. While his back was turned to the girls, he was vaguely able to see them sifting through the large bags Sara had brought before cackling maniacally over their contents. His heart rate instantly picked up again, knowing deep down that whatever Sara had come back with was certain to be a humiliating endeavor. 

TO BE CONTINUED…