Stepmother Knows Best, Pt. 3
“Oh, he is just going to look so precious in these!”
“Please tell me you got the biggest you could find!”
As Rachel and Deloris fawned over the contents of the bags that Sara had ferried into the walk-in closet, Ryan’s dreadful anticipation only grew. At first, his concern had remained mild, assuming whatever Sara had brought over must’ve been an extra girly outfit or something. However, as time stretched and the girls kept digging and digging, his concern began to rise slowly and steadily until it was so intense that he could barely stand still.
“I’m almost kinda nervous. I’ve never done something like this, “said Rachel, fanning her flushed face as all the excitement had sent a wealth of blood to her cheeks.
Rubbing her hands together, Deloris did not share Rachel’s anxiety in the slightest, “Relax, I’ll take care of…that part. It’s been a few years and he’s a bit bigger than I’m used to but I’m sure I can still manage.” She turned her head back to look at Ryan, making sure her words were deliberately vague enough for him not to understand.
Perhaps the anticipation that Deloris was setting up for Ryan was a tad too much, though, as a very frustrated Ryan finally got fed up with waiting for the big reveal. Stomping across the closet with his green velvet dress only half on, he shoved an unprepared Rachel out of the way before tearing the bags open. “Will you quit it with the theatrics?! Let’s just get this over…with…” said Ryan, his words petering off as he stared into the void of the bag, terrified of what was staring back at him.
Without hesitation, Ryan made a break for the closet door. It didn’t matter how he was dressed or what his dad saw anymore. It would be a cold day in hell before he’d willingly let the girls put him in something so fundamentally psychotic. Where did Sara even find that stuff?! Grabbing onto the door handle, he was instantly accosted by all three women, who gleefully dug their claws into his body with every intent of restraining him for what was to come. In spite of Ryan’s best efforts, three against one was not a fair fight. His fingers held onto the little, golden knob for as long as he could but eventually, his digits gave out and he was forced to the ground on his back. “N-NO! I-I did everything you wanted me to! You can’t do this to me!!!” he screamed, writhing around on the carpet as the girls did their best to pin him down.
“Deloris, go get the package! We’ll keep him down,” said Sara, placing a knee on Ryan’s chest as she used her entire body weight to keep his arms at his sides.
Simultaneously, Rachel was being thrown around by Ryan’s legs as she rested her body on top of them with her arms hugging his lower appendages to her chest. In a way, it was a lot like riding a mechanical bull, only much bonier. “P-Please hurry! He’s killing my boobs!” she groaned Rachel as Ryan slammed his feet against the floor, sending shockwaves up through Rachel’s poor, defenseless mammaries.
Rachel’s words only encouraged Ryan to thrash harder. He didn’t like the idea of hurting a woman physically in any way but since he was essentially a hostage, desperate times called for desperate measures. Sadly, thanks to being kept in Rachel’s closet all afternoon, the last meal Ryan had eaten was breakfast, which at his point was nearly seven hours prior. Additionally, he’d also been made to cum multiple times today, weakening his body tremendously. Because of this, it only took about 45 seconds of jerking his body around for the exhaustion to kick in. With no more gas left in the tank, his body went limp all at once as his breathing became haggard and weary.
“So much for all that big man strength,” said Sara, giggling at her own poor impression of Randy Savage. Having taken care of Ryan, she turned her attention to Deloris, sinking her teeth into her bottom lip as her grand revenge scheme began to unfold. Since there was nothing he could do now, she leaned in close to his ear, wanting to make sure he understood precisely why this was happening, “Looks like Soggy Sara is the one who gets the last laugh.”
While Sara may have been on cloud 9 after revealing why she’d been harboring vengeful feelings for so long, Ryan’s confusion only grew as he had zero memory of her birthday party wetting accident or the cruel nickname that he coined that day. Tragically, it mattered little what he did and didn’t remember because he was going to pay the price for his past self’s actions whether he wanted to or not.
“Alright! Time to say goodbye to those big girl panties you love so much,” said Deloris, snickering as she sat down on Ryan’s thighs, taking the pressure off of Rachel a little. She wrapped her fingers around the waistband of the lacy, vibrating panties and pulled them down, maneuvering them through her legs before passing them off to Rachel to do the same.
Then came the moment that made Ryan’s heart stop as Deloris raised an unfolded adult diaper for Ryan to see. “At least we won’t have to worry about you making sticky accidents in Mommy’s dwesses anymore,” she said, cooing at Ryan with a babyish affect like any good mother would.
After a bit of finagling, Deloris managed to slide the soft padding under Ryan’s rump. This triggered him to begin wagging his hips around in a last-ditch attempt to make this as hard for the girls as possible. Unfortunately, Deloris had seen this coming and had already thought up a perfect solution. As his hips were moving around, she reached down and clutched his dick and balls tightly, forcing the emasculated Ryan to let out a sharp yelp as his body went stiff and rigid. “That’s enough of that. There’ll be no more fussing about until Auntie Deloris gets you changed. Is that clear?” she said, giving his boys a test squeeze to show Ryan she meant business.
Wincing in pain, Ryan once again went limp under Deloris’s very serious threat. He felt his pride shatter to pieces as he willingly let his butt rest atop the fluffy diaper. “Th-This is the last one, right?” he asked, praying that this would all be over soon.
“Of course,” said Deloris, her condescending smile filling Ryan with little hope that she was being true to her word. Sadly, as much as he didn’t believe her, it was the only form of hope he could cling to at this point.
Squirting several long streaks of baby lotion into her hand, Deloris pressed the gooey substance against Ryan’s cock, smothering his sore penis in creamy goodness. Her fingers ran down the length of his shaft and balls, ensuring a thick, even coating. She then added more lotion to her hand before applying coverage to the rest of his front diaper area, running her hand between his upper thighs and across his budding pubic hairs. “I’m almost kind of shocked his bikini area is so well groomed. I half-expected to find a forest,” she said, lightly pinching at his curly hairs with her fingertips.
“I can answer that one,” said Sara, her chipper voice striking fear into Ryan’s soul over what she might say next, “I think I mentioned to Ryan like a year ago maybe that only virgins don’t keep their pubes trimmed. Guess he took that to heart.” The three women all cackled at Ryan’s attempt to appear experienced, further fueling the blush in his cheeks.
“Well, I certainly appreciate you making this easy for me, Baby Ryan,” said Deloris, giving his actively swelling shaft a final once over before turning to Rachel, “Alright, we’ll need to lift his legs to cover the booty. One, two, threeeee-Ugh!” With a soft grunt, Deloris and Rachel pushed Ryan’s legs into the air to expose his smooth buttocks. Knowing they couldn’t keep him held in this position for long, she pushed the bottle of lotion close to his butt and began slamming down on the pump, exploding a plethora of lotion onto Ryan’s ass. She then used her free hand to rub it into his skin, spending an extra amount of time running her open palm through his butt crack.
As a parting gift, as Deloris finished getting him all lotioned up, she let her middle finger slip inside Ryan’s puckered anus. The reaction was instantaneous with his body convulsing wildly from the rear intrusion. His body may have been weakened but having his back door played with was enough to wake his muscles up momentarily. He twisted his legs free from Rachel and Deloris's grasp as he crashed back down on top of the open diaper, panting heavily.
“Well, at least that part’s over,” said Rachel, chuckling as she wiped the moisture from her forehead, “So what’s next?”
Looking around the nearby area, Deloris let out an annoyed sigh. “Shoot, I must’ve left the baby powder in the bag. Keep him held while I go grab the bottle,” she said, helping Rachel shift so that she was sitting atop his legs again facing his feet with her hands clutching his ankles tightly.
Left alone with Ryan’s upper half, Sara ran her fingers along his chin as she whispered, “See? This isn’t so bad, is it? I’ll bet all that lotion feels extra soothing.” She reached across his body and brushed her hand against Ryan’s lubricated cock, enjoying the way his body quivered from her touch.
Lightbulb!
Looking back and forth between Rachel and Deloris, Sara realized that this was the perfect opportunity to kick Ryan’s humiliation up to the next level. Tucked away in her pocket was a special tool that she had picked up from the CrissBaby store along with the diapers. She pulled a small vial out and held it up to her eyes. Its label read, “CrissBaby Diaper Aphrodisiac - Rose Scented.” Just a couple drops of this would keep him as hard as a rock for hours. Unscrewing the cap, she set the dropper aside, opting to pour the entire bottle onto his slightly stiff member instead. She quickly spread the liquid all over his naughty bits, rubbing it into his skin so that Rachel and Deloris would be none the wiser.
Ryan, meanwhile, had no clue what Sara was up to. From his perspective, she had randomly decided to start playing with his penis. Over the course of five seconds, his mind ran the gamut between having his wildest fantasies realized with Sara and the fact that he was still wrapped up in a green velvet dress with a fresh diaper under his ass. Unsurprisingly, his dick was nowhere as conflicted as his brain was as it expanded to a full erection in no time. His moment with Sara didn’t last long, though, as she quickly pulled her hand away before Deloris could return with the lotion.
“Oh my! Someone seems to be having more fun than they’d like to admit” said Deloris, her eyes falling on Ryan’s pulsing hard-on. Her words prompted Rachel to look behind her before flopping to the floor in hysterics.
Knowing his arousal was all Sara’s doing, Ryan wanted to argue that he wasn’t enjoying a second of this. However, after the number of times he’d been made to climax from the vibrating panties, it wasn’t likely his words would hold any water anyway. Instead, he furrowed his brow and looked away from the three giggling girls. “J-Just do it already,” he said, unaware of how much his anger looked like bratty pouting.
“Worry not! One last step and we’ll get your lil’ buddy swaddled up in something nice and cozy,” said Deloris as she got to work sprinkling powder all over Ryan’s crotch. Thankfully for Ryan, the powdering process was much more expedient than the lotioning had been. The girls pushed his legs up again and scattered the linen-scented substance across his bottom before pouring some directly onto the diaper. Laughter was once again jump-started as she lowered his butt back onto the diaper, causing a poof of white powder to waft into the air. It was all over from there, as she unceremoniously lifted the diaper up between his legs and taped it down tight over Ryan’s stiffy.
With his diaper now secured, Ryan went numb, unable and unwilling to accept the crinkly plastic that his hips were wrapped up in as reality. Unfortunately, the numbness was soon replaced by an odd tingling sensation that began to emit from his privates. It wasn’t unpleasant but it was unnaturally hot. He began repeating the word, “No,” over and over again in his head as the pleasurable warmth induced his inflating cock to strain against the fluffy confines of his diaper, something that did not go unnoticed.
“Well, would you look at that,” said Rachel, finally lifting herself off of Ryan’s legs as she honed in on his tented padding. She gave the tip a tiny poke, amazed as just the slightest touch nearly sent him over the edge, “I don’t believe it but I think he’s even more turned on by this than the vibrating panties! Did we accidentally stumble across your secret fetish?”
Hell was starting to look like an all-expense paid vacation compared to the unreal humiliation that was being inflicted on Ryan. What was happening to him? He stabbed his teeth into his tongue and scrapped his fingernails against the flesh of his hands, doing anything he could to lessen the euphoric tingles that were enrapturing his dick.
While Ryan was fighting a war of attrition against his own arousal, the girls moved in with the final piece of Ryan’s sissy baby wardrobe. “Since you couldn’t get enough of all those fuzzy, girly feelings, I figured this would be right up your alley,” said Sara, holding up a powder blue, taffeta party dress with poofy sleeves, an extremely short skirt, and a built-in petticoat. Unlike the other outfit that Ryan had been coerced into wearing, this one was by far the shortest, looking more as though it had been made for a ten-year-old, “Of all the outrageously girly things my mother made me wear as a kid, this was the one dress that even she couldn’t force me into! So don’t worry about returning it! It’s all yours, Baby Ryan!”
“Wow, thanks,” said Ryan with a heavy dose of sarcasm. Feeling utterly defeated at this point, he allowed Rachel to lift his arms up so that Sara could slide the dress onto him. It was by far the softest and smoothest thing he had worn so far. The buttery fabric hugged his torso from every angle, pinching his waist a bit due to the fact that the dress barely fit past his fairly broad chest. As the dress’s delicate petticoats brushed against his sensitive thighs, he could swear he felt his penis growing even harder inside his diaper. What was happening to him?! He didn’t enjoy this…right?!
Elated by the conflicting emotions that Ryan’s face was zooming through, Deloris stepped in behind him and took hold of his extended hair. “It’s okay if you’re starting to enjoy this, ya know? You’re one of the girls now, Riley” she said, gifting him a feminized version of his name to match his appearance. She suppressed her giggles at Ryan’s expense as she began shaping his hair into a pair of adorable pigtails.
“You sure about Riley?” asked Rachel, pondering over if Deloris’s new name for Ryan was precious enough, “What about Raelynn?! Then we can call him Lynn for short!”
Placing her thumb and forefinger on her chin, Sara chimed in, “I’m more partial to Rain if we’re being honest. It sounds like something a trendy girl would pick out for herself.
As the ladies argued over what Ryan’s new girl name should be, Ryan could only stand in place and gawk at his own reflection. Gone was his father’s wealthy slob of a son, replaced by a little diaper girl who didn’t even look old enough to drive, let alone take over his father’s company someday. Speaking of his father, he knew based on the way the sun was hitting the master bedroom window adjacent to the closet that it was pretty late in the afternoon. “H-Hey, c-can we please be done now,” he said, cutting off the girls in the midst of his renaming summit. He choked back tears as he pleaded for mercy, “My d-dad’s gotta be getting home soon.”
Looking back and forth between Sara and Deloris, Rachel spoke up. “Oh yes, I’d say we’re done. This’ll be perfect. Thank you for being so patient with us today while we figured out your new wardrobe,” she said, stepping toward Ryan slowly like a predator stalking its prey.
“That’s right! It took a bit of trial and error but I’m with Rachel. This is the perfect basis for your new look! Now we can pick you out a bunch of new clothes and accessories!” said Deloris, positioning herself so that she was in the way of Ryan’s most direct escape route.
Circling around to Ryan’s side, Sara pressed her fingers together, unaware of how much her posture was akin to a cartoon villain. “I have plenty of old dresses just like this one that you’re free to wear whenever! And don’t worry if Daddy cuts you off! You can always come stay with me and be my 24/7 dress-up dolly,” she said, closing in on Ryan and placing an arm around his shoulder, “Doesn’t that sound sooooo fun?!”
Shaking his head, Ryan reacted much like any cornered animal would. He broke from Sara’s casual hold on him, making a mad dash for the door. To his surprise, the ladies allowed him to break through the closet door. He sprinted around the bed as fast as his diapered legs could waddle. If he could just make it back to his room then this whole nightmare would be over. Racing down the hallway, he approached his bedroom door at the far end. “Hahaha! Go fuck yourself, Rachel!” he screamed at the top of his lungs as he grabbed the handle to his bedroom door victoriously.
Rattle!
In an instant, the cheerful and relieved expression on his face disintegrated as he jiggled the doorknob, only to find that the girls had locked it from the inside. “N-No! Nonononono!” he shouted as he desperately rammed his shoulder into the door multiple times.
“Oh, Raelynn!” said Rachel in a sing-songy as she and her two cohorts stepped out into the hallway, cornering Ryan in an even tighter space, “Did I hear you say a potty word about Mommy? That’s a big no-no.”
Folding her arms with a satisfied smirk, Deloris was more than happy to respond in Ryan’s place, “Sounds like someone earned herself a big punishment! And we were just about to get you changed too.” Both she and Ryan knew she was lying but teasing Ryan with his failed escape attempt was too delicious to pass up on.
Turning around slowly as if he was a final girl in a horror movie, Ryan’s heart filled with dread as he saw the three women slinking toward him side by side, ensuring that the entire hallway was blocked by their bodies. “Y-You three are fucking insane-HEY!” he yelled as the girls easily wrestled him to the ground before lifting him in the air, “Put me down! W-Where are you taking me?!” His fingers scraped against the pure white balusters, hoping to grab hold of anything to halt the girls’ campaign, even if only for a brief moment. Sadly, his arms were too constrained to do any real damage to their plans, allowing them to carry his body downstairs to the living room without much of a fight.
“Let’s get him tied down right here,” said Rachel as she and the others sat Ryan down in front of the tea table. The girls then proceeded to use a set of Rachel’s silk scarves to bind his ankles and waist to his seat.
Meanwhile, Sara and Deloris got to work subduing Ryan’s arms. “Keep a hold of him for a sec, Deloris! I’ve got the perfect way to keep him pinned,” said Sara, making sure Deloris had a good hold on Ryan before racing back up to the walk-in closet, only to return in a matter of seconds with a fluffy, pink teddy bear in her arms. “Remember, Mr. Fluffles? You made fun of me for having him in my bed the one and only time I let you into my room. What was that you said? Only toddlers sleep with stuffed animals? Guess he’s perfect for you now.”
Nestling the plush bear into Ryan’s lap, Delrois and Sara forced Ryan to wrap his arms around the stuffy before tying them into place, binding him in much the way a straight jacket would. With his arms, legs, and waist fully bound to the seat, the most he could do was wiggle in place, unable to shift his body more than a handful of inches in any direction. “What?! Are you bitches gonna make me have a stupid tea party with you now?!” he said, his mouth existing as his only source of defiance.
“Such rude language for such a proper lady,” said Deloris, who by this point was done with Ryan’s foul words. Thankfully, she’d done some digging through Sara’s goodie bags and found the perfect solution to this problem. Pulling out a pink pacifier with a massive ball in place of a mouthguard and four laces attached to it, she stormed up to Ryan and plopped it into his mouth before tying the laces around his head to keep it secure.
For Ryan’s effort, he attempted to spit out the pacifier or at least dislodge it in some way but without his hands, there really wasn’t much he could do. “D-Dish ish shtoopid!” he screamed, muffled by the wide bulb of his shiny, new binky.
“That’s enough out of you,” said Deloris, grabbing the pink orb that was attached to Ryan’s paci and giving it a hardy squeeze. This caused a rush of liquid to push out of the bulb in Ryan’s mouth, coating his mouth in a thick, berry-flavored syrup. With nowhere for the liquid to go, he was forced to swallow it, much to Deloris’s delight, “CrissBaby makes so many fascinating things. Who would’ve ever thought to make a pacifier with a dispenser attached to it?”
Nodding in agreement, Sara was feeling quite proud of the purchases she had made. “I know right?! You filled the bulb with that oral numbing agent I bought, yeah?” she asked excitedly.
“Of course! That should keep our little girl sounding sweet for the foreseeable future,” said Deloris, relishing in Ryan’s agony, “The bottle says not to leave it on too long unless you really, really want it to be permanent. Funny how they worded it that way. It’s almost like they know it will be used to turn sissies like you into lispy, little pwinceshesh! Hehehe!”
Sure enough, it was only a matter of seconds before Ryan could feel the light prickles of numbness invading his mouth and tongue. “D-Dish shtuff betta wash off!” he said, uncertain if it was the pacifier or the numbing agent causing his lisp at this point.
“Oh, hush. Your mouth may say one thing but your body is saying something completely different,” said Rachel, who had finished with Ryan’s ankle restraints just in time to grope his diaper-encased hard-on for dramatic effect, having no idea that his unending erection was the direct result of Sara’s sabotage.
Whimpering as he wiggled his hands and feet fruitlessly, Ryan was utilizing every ounce of resistance left in him to keep from enjoying his stepmother’s loving touch. Why did diapers have to feel so good on his cock?! “D-Dat doesn change…nuffin! I neva wan-ned any of dish!” he shrieked, his voice cracking under the pressure of perverse pleasure.
“Sorry, sweetie but it doesn’t matter what you want anymore,” said Rachel, giving Ryan’s diaper front one last good squeeze before reaching into her pocket and pulling out his favorite lacy, vibrating panties, “This is your new life now, so get used to it.” Without warning, she pulled open the waistband of Ryan’s diaper and shoved her hand with the panties inside before carefully wrapping the silky undergarment around his stiff pecker. Standing up with a smug smirk imprinted on her face, she pointed the vibrator’s remote at him and clicked it on to full speed. She then let the remote fall from her hand to the floor before lifting her heel and crushing it, making sure the panties would stay on until the battery was drained.
Ryan’s eyes went cross as his dick was engulfed in unmitigated pleasure. Everything from the way the dress moved against his skin to the thick diaper that soaked up every ounce of seed that dribbled out of his penis was designed to ramp up his horny femininity. He bellowed out a deep moan into his pacifier as he began to mount another climax.
RUMBLE!
Suddenly, the sound of a garage door opening captured everyone’s attention. “He’s home! Quick, girls! To your positions!” said Deloris, circling around the table hastily and taking a seat at the tea table directly across from Ryan.
Rachel and Sara both joined her, placing themselves in the two seats neighboring Ryan’s so that all four were now taken up. “Care for some tea?” said Rachel, lifting the teapot and pouring the warm liquid into her glass before doing the same for Ryan’s teacup.
“Yes, please,” said Deloris, lifting both her teacup and saucer and holding them out for Rachel to pour into. As her cup filled with tea, she glanced over at Sara, “And Sara, you should join us for tea more often! We’d love to let you in on all of our juiciest gossip.”
Snagging a couple of cookies and setting them on her plate, Sara nodded to Deloris. “I’d love to! Besides, I’m sure I’ll already be over here a lot to babysit,” she said, turning her attention to Ryan and giving him a soft pinch on the cheek, “We’re gonna have so much fun together from now on. I’m so happy that you’ve decided to be my prissy sissy baby forever.”
Watching his adult male life slipping through his fingers like grains of sand fluttering in a warm, summer breeze, Ryan shed one final tear for his manhood, knowing his life as he’d come to know it was officially over. His wrists and ankles twisted in place as a hot load of cum was squirted into his diaper right as his dad opened the door.
“Honey, Ryan, I’m…home…”
THE END.