Growing Into Diapers: Chapter 7

“Has my silly little girl learned her lesson…or do we need to take a more hands-on approach for your next punishment?” 

With his arms and legs bound to a desk, Edan squirmed within his loaded, cum-coated diaper as his teacher, Miss Aubrey, stood over holding a yardstick. As she smacked the stick against her hand, he could already feel the sting on his ass before she’d even landed the first blow. Deep inside his diaper, his vibrating butt plug purred loudly, causing his legs to buckle uncontrollably. 

“No answer? Punishment it is then,” said Aubrey as she cranked up the speed of Edan’s vibrator, causing him to lose all control. Drool spilled down his chin from behind the cock-shaped pacifier he was forced to suck on. Time seemed to stand still as waves of unadulterated pleasure shook his body to the core, “Now, let’s get you leaned over that desk so I can teach you how good little girls are meant to behave-” 

BEEP! BEEP! BEEP! 

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*BEEP BEEP! BE-” 

Slapping his hand down on his alarm clock, Edan groaned as he shifted the blanket over his head, wishing for his slumber to continue. Ever since he’d had that sexy work dream, not a night had gone by without him reliving the naughtiest moments. As fun as that would sound to most, it had made quite the restless sleeper out of him, meaning that he was constantly tired. At least Malorie’s CD put him to sleep almost immediately but that was only a small consolation prize. 

Lifting up his bed sheets, Edan winced as his used, lukewarm diaper squelched under his butt as he sat up. His morning wood pressed against his slippery diaper front, letting him know that his dream had ended in a creamy surprise yet again. At least Aubrey had been understanding about why he hadn’t been holding in his loads better. Not that it really mattered, though, since every time he climaxed, more and more semen seemed to come out. It was at the point where he threatened to overflow the front of his diaper anytime he finished. And while it certainly felt like heaven, the clean-up was anything but.  

“Alright, let’s get the over with,” Edan grumbled as he laid down on the change mat that was in the corner of his bedroom and got to work. He had another long day of work ahead of him and there wasn’t any time to waste. Grabbing two incredibly thick diapers, he flattened them out on the mat, feeling his heart flutter as he sat down on his plushy throne. This much bulk wasn’t necessary but he knew how happy it would make his Mistress to see him waddling around the office. 

The thought alone made Edan giggle like a little girl. As soon as he heard his cutesie laugh echoing in his ears, he slapped his hand across his mouth immediately. All these thoughts of diapers and buttplugs and girly outfits were getting to him. Maybe if he asked nicely, Aubrey would let him be a bit more manly in their play session. He quickly finished up his diaper change, excited to finish getting ready so he could see Aubrey and all of his friends at work. 

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Somehow, even walking into the office had become an erotic situation for Edan, due mostly in part to the new dress code that Aubrey had started enforcing on him. That being the set of silky lingerie that he wore under his button-up shirt. Having made the mistake of confessing to his Mistress the naughtiest details of his wet dream, she thought it would be fun to start incorporating elements of his dream into their play sessions. Specifically, the crossdressing element. 

In the week and a half since that dream, Edan had worn a maid outfit, a cheerleading uniform, a latex bodysuit, and, of course, a dreaded schoolgirl outfit. Having been made to wear girls' clothes for so many days in a row was definitely starting to mess with his head. He could still hear the comment Rita made a few days ago echoing in his brain, “Cute little butt wiggle you’ve got going on there, mi hijo. And I thought my hips swayed.” His face flushed as her words replayed in his mind over and over, causing him to walk in the most robotic of ways. 

DING! 

Stepping off the elevator, Edan made a beeline for the break room, hoping to make up for the fact that he’d run out of coffee this morning. However, just as he was about to enter the break room, a familiar face stepped in his path. “Sorry, Edan. No peeking until it's time for the party,” said Malorie in an unusually chipper tone.  

“Party? I’m just here for some coffee. I promise I’ll be quick,” said Edan, attempting to sidestep around his colleague.  

Malorie was having none of it, though, holding her arms out wide to create as large of a barrier as possible, “Nope, no exceptions allowed. Corporate wants the Grow-With-Me Diaper pre-sale party to go off without a hitch. I can grab you a coffee if you want, though. Two creams, two sugars right?” 

“Um, yes. Thanks,” said Edan, deciding it wasn’t worth the argument if Malorie was going to deliver his daily dose of caffeine directly to his desk. As he walked away, two other employees stuck their heads out through the break room doorway, snickering as they watched Edan unwittingly sashayed to his desk. 

Parking himself down at his desk, Edan lowered his head, silently praying for a boring Friday morning. Thankfully, his wish appeared to be granted as the hours ticked by leading up to lunch. While uneventful, he couldn’t shake the feeling that he was constantly being watched. Several co-workers who he rarely saw seemed to keep strolling by his cubicle and giving him extended glances. In the end, he chalked it up to paranoia brought on by the sexy lingerie, completely unaware that the more time that ticked by, the more urine was let out into his diaper. It wasn’t even noon by the time his two diapers had swollen to nearly the size of a beach ball. Despite their outrageous growth, not a single drop of urine leaked out. Nothing was more reliable than CrissBaby diapers, after all. 

Speaking of his lingerie, the silky undergarments were doing a number on his nipples which had been fully erect throughout most of the morning. Even the slightest movements ran the risk of causing the smooth, flowy fabric to graze against his sensitive chest, which had recently been a bit softer and poofier. He did his best to put it out of his mind and focus on work, making a mental note to hit the gym again soon. 

“Edan, hey! I’ve got something for you,” said Aubrey, surprising Edan by setting a medium-sized box on his desk. Before he could even ask what was inside, she tore open the cardboard flaps and proceeded to show off the pair of pink, silk mittens for Edan to see, “Looks like corporate is turning our little celebration for the Grow-With-Me Diaper into a fancy dress party. Don’t worry, everyone else is going to be wearing the same thing, so you’re free to be your blushy self all afternoon!” 

Edan could feel his heart beating up in his throat as he stared at the padded mittens Aubrey was holding out for him. It didn’t matter if everyone was wearing the same thing. This was going to be his first time dressing like a sissy baby in front of his co-workers. He could feel his stomach doing somersaults over the possibility of Aubrey doting on him in plain view of the entire department. 

“Is that really all you’ve gotten done today,” said Aubrey, bringing Edan back from the void he was spacing off into. Sure enough, displayed on his computer screen was an empty excel document with nothing but gibberish typed throughout a few dozen columns. 

This was merely a highlight of Edan’s recent concentration issues. Much like how he was spacing off mid-conversation with his boss, his attention span had almost fully evaporated in recent weeks. Not knowing what to say to Aubrey, his face turned bright red and his breathing became panicked. 

“Awww, it’s alright. We all have days like that,” cooed Aubrey, wrapping her arms around Edan’s torso from behind his chair, “Why don’t we head to my office early today? That way we can take our time getting you all dressed up.” 

Sniffling and wiping a lone tear from the corner of his eye, Edan nodded and allowed Aubrey to take him by hand. He kept his head down as she led him through the office, knowing how inherently embarrassing it was to be walked through the office like a snotty toddler with his ultra-saggy diaper squishing between his legs with every step. And yet somehow, deep in the pit of his stomach, it felt so right for him to let Aubrey treat him this way. 

Upon entering Aubrey’s private office, Edan was greeted by Malorie and Rita, who were already waiting for him with a fresh diaper and bottle in hand. “You’re gonna look so cute in your party outfit,” said Rita as the trio of domineering women guided him to his usual changing spot on the desk. 

“W-Wait, why are Rita and Malorie here?” asked Edan, his mind flashing back to the horny dream he’d had in this exact spot with all three of them. His cock rose in response within his soggy diaper, mooshing itself against the swollen padding. 

Placing both hands on Edan’s cheeks, Aubrey put Edan’s focus directly on her. “They’re just here to help you get ready. It’s not like these two have never changed your diapers before,” she said, prompting the brigade of milfs to descend on him. 

Everyone had a role to play. Moving from his head down to his diaper, Aubrey got to work changing Edan into his latest diaper. The moment his butt touched down on the plushy surface, he knew something was different. Craning his neck up, it was clear as day that whatever diaper they were placing him in was significantly less thick than any they had put him in before, much to his surprise. 

Before Edan could say anything about the size of his new pamper, Malorie stepped in with the milk bottle. She lifted his head onto her lap and plopped the rubber nipple into his mouth, relishing in how glazed-over his eyes were. “She's practically a real baby now,” she said, knowing he’d traveled too far down the rabbit hole at this point to fight against anything they were doing. 

“W-Weaw baby?” stuttered Edan just before sweetened milk was squeezed into his mouth, causing him to moan in ecstasy at the marvelous flavor. What were they even talking about? He didn’t really care so long as he got to slurp down this delicious nectar. 

Meanwhile, Rita was moving around the desk, placing each of his limbs into some babyish bondage. “Mittens are secure! Let’s get these cutie booties on you next!” she cooed, pinching Edan’s cheek before rotating to the edge of the desk. 

SLOOOORP! 

“MMMMMMMM!!” 

Edan’s hips bucked upward as Aubrey took hold of the butt plug he’d gotten so familiar with and unceremoniously removed it from his anus. “Shhhhhh, it’s okay, baby girl. Calm down. Auntie Mal’s got you,” said Malorie, stroking Edan’s hair to calm him down as he continued to feed from her hand. 

“Brace yourself, Edan-baby,” said Aubrey, prodding Edan to focus his attention on her again. This time, she made sure to show off what she was planning to do. In her hand was a larger, vibrating butt plug that Edan was all too familiar with. It was the plug that lived in infamy within his own head. How on Earth did Aubrey manage to find the exact same vibrator that he’d dreamed up? 

Sadly, Edan had no time to figure out the answer to his own question. All conflicting thoughts were jettisoned from his brain the moment that the longer and thicker toy was shoved inside of him. His bottom lip quivered as Aubrey pulled the diaper up over his rock-hard phallus, causing the plug to push further into him as the diaper tightened around his waist. 

“Time to sit you up,” said Aubrey, prompting Malorie to set aside the mostly finished bottle and replace it with a large, pink pacifier as she helped her boss move Edan into an upright position, “I’ll bet that plug feels even better with all your weight on it.” 

A mixture of drool and baby formula trickled down from Edan’s lips as his new plug invaded previously unexplored territory. “Eheh…dat feews goods,” he said, causing the women around him to giggle at his docile state of mind. 

“Arms up, mi hija,” said Rita, encouraging Edan to lift his arm all on his own, “That’s it! Such a smart baby! Yes, you are!” Reaching over Edan’s head, she pulled the top over his head and slowly slid it down his body, making sure to smooth out any wrinkles along the way. Once the outfit was over his diaper, she stepped back, allowing Aubrey to handle the rest. 

“Thank you, girls. I’ll handle her from here. Can you both go gather everyone in the break room?” asked Aubrey, sending Malorie and Rita out into the office and leaving Edan all alone with her, “Alright, my baby. We’ve got one last thing to do.” Taking Edan by the hand, she stood him up off the desk and crouched down to snap together the bottom buttons of his new ensemble. 

Once the buttons were in place, Edan was ushered toward a full-body mirror that he’d never seen in Aubrey’s office before. That was the last thing on his mind, though, once he caught sight of his reflection. A flurry of lace ruffles curled around his upper body and wrapped around his diaper-covered booty, their light pink shade perfectly complementing the hot pink fabric of the onesie. If that wasn’t bad enough, adding to the humiliation this outfit filled him with were the words, “Mommy’s Princess”, which were written in bold across his chest. There was no way anyone could look at him and see an ordinary office worker. Heck, they wouldn’t even see a man. He’d been fully reduced to the status of a baby girl. 

Before Edan even had time to reconcile with his feminine appearance, Aubrey scooped him up off the ground, showing off her strength as she cradled him like a newborn infant. “Okie dokie, my sweet cupcake. Let’s go have some fun,” she said, throwing open her office door and stepping out into the bright, fluorescent lighting. 

For Edan, this was the first time he’d ever left her office while wearing a girly outfit. While he took comfort that everyone else would be dressed similarly, it didn’t make the experience any less nerve-racking…wait a minute…why wasn’t Aubrey dressed up like he was? “M-Mistwess, awen’t chu gonna get dwessed up to?” he asked, his realization coming far too late. 

As Edan and Aubrey stepped into the break room, the palpable atmosphere weighed heavy on Edan’s heart. With his head resting on Aubrey’s shoulder, he couldn’t see what was happening in the room, but that didn’t stop him from hearing murmurs and stifled chuckles all around him. Something was very wrong. 

Setting Edan’s feet back on the ground, Aubrey rotated him toward the wider landscape of the break room. This brought him face to face with the collective of his fellow employees, all of whom were dressed like normal adults in business casual outfits. In an instant, every ounce of oxygen in his lungs disintegrated. 

“SURPRISE!!!” 

TO BE CONTINUED…