The Sissy Box

Stanley, a third-year undergrad student, slammed his front door shut as he entered his apartment on a breezy Thursday evening. Slumping his backpack on the floor by his desk, he laid down on his bed and smiled. This weekend was going to be one to remember. 

Kicking off tonight, Stanley had made plans with a few of his pals to hit up Thirsty Thursdays at Mickey’s. Sure their beer tasted like piss, but it was dirt cheap and they didn’t card, so beggars couldn’t be choosers. Then, after remedying his hangover tomorrow, he had plans for a three-day binger with his fraternity, where he had his very prestigious beer pong win record to uphold. 

Now, most students would be worried about Friday classes before diving into a Thursday night bar crawl. But not Stanley. He’d specifically planned his schedule to give him Fridays off. And with Monday being a bank holiday, he didn’t have to worry about classes until next Tuesday. Needless to say, he had it made and felt like a king in his college town. 

However, before Stanley could begin his much anticipated weekend, he knew he had to take care of business. Slipping his phone out of his pocket, he slid off his jeans and began to scroll through all the porn he had saved. While he knew there would certainly be several opportunities to get his nut off during a three-day frat party, that didn’t stop him from diving into one of his favorite pastimes. 

Squeezing some lotion into his hand and grabbing a few tissues, Stanley placed his right hand on his cock and began to slowly knead and prod at his flaccid self, getting it to a fairly erect state. Unfortunately, just as he was starting to get into a good rhythm, his jerk session would be interrupted. 

BUZZ BUZZ BUZZ BUZZ 

Suddenly, a call popped up on Stanley’s phone. The unexpected vibration of his perma-silenced cellphone startled him and caused him to drop it on his chest. With the mood now ruined, he lifted up his phone. “Of course,” he scoffed under his breath as who else would suck the fun out of a period of personal reflection than his ex-girlfriend, Amber. 

About a week ago, Stanley had put the kibosh on his relationship with his girlfriend of two months. Things started off hot and heavy between him and Amber but quickly grew cold after she accused him of cheating, which he vehemently denied despite being totally guilty of sleeping with another girl. It’s not his fault that women were always throwing themselves at him when he was drunk. In his mind, sometimes, charisma could be a curse too. 

Having no interest in digging up old dirt with his ex, Stanley let the call go to voicemail, hoping that Amber had somehow butt-dialed or something. Sadly, this was clearly not the case, as seconds after the call ended, a message popped up: “Look, you don’t need to dodge my calls. I don’t wanna talk to you either. I just want the rest of my shit from your apartment. Do you mind grabbing the cardboard box I left in your closet and putting it in the hall? I’ll pick it up in a bit. PS, whatever you do, don’t open the box!” 

Rolling his eyes, Stanley was honestly just happy that it wasn’t another one of Amber’s “talks.” He quickly responded with a brief, “Sure,” before making his way over to his closet, where the box was waiting for him tucked in next to the wall. He slid it out and picked it up, surprised by how light it was in spite of its near watermelon-length size. Additionally, whatever was in it wasn’t very big, as the few objects that existed rattled about in the mostly empty box. 

With a smug expression, he grabbed his box cutter and cut into the tape that kept the box closed. Not only did he want to piss off Amber and peek at whatever she didn’t want him to see, but he was also just curious about what she could’ve sealed inside. As he parted the cardboard, however, he was disappointed to see that it was what looked to be a bunch of stereotypically girlish items with a pink take top draped over top of them. 

But, as he reached inside and lifted the tank top up, he soon discovered that the objects in this box were far from stereotypical. 

Under the shirt, there were several items that caused Stanley to pause and wonder if he ever really knew Amber all that well. The first and least objectionable was the wireless wand vibrator that he could only assume was used some private sexy time, a thought that made him giggle immaturely. 

From there, though, things took a quick downturn. The next two things that Stanley pulled up off the box were a set of frilly socks and a bright pink pacifier. He tried to think hard if he remembered Amber mentioning if she had a young sibling or cousin, but that was mostly the denial talking, as he stared down at the final object in the box. 

A light pink and soft-looking plastic rectangle sat at the bottom, resting ominously in the middle of the cardboard. Given the size of both the binky and what he could only assume was a diaper, he knew there was no way these were designed to be worn by a child, no matter how much his brain tried to rationalize that they were. Deep down, he realized he’d just stumbled upon Amber’s biggest and most embarrassing secret, and he wasn’t sure if he should be jumping for joy in eagerness at having something to lord over her, or if he should be slightly disturbed that he’d wasted his time plowing some diaper lover.  

With a hearty chuckle, Stanley reached inside and placed his fingers around the crinkly, plush surface, unaware that in doing so, he’d just signed away his life as he knew it. Not even a second after his hand made contact with the diaper, his body began to move on its own. Grabbing onto the hem of his shirt, his arms raised up and flipped it off of his body, leaving him standing in the middle of his room butt naked.  

Internally, Stanley was screaming, trying to get his body back under his control, but as he sat down on the floor with the diaper in hand, he realized just how futile his efforts were. Slowly, he unfolded the pink monstrosity and laid it out flat on the floor. He then proceeded to lift himself up and place the diaper underneath his butt, before settling back down. 

Turning his head to the side, Stanley looked under his bed, finding two bottles that he knew shouldn’t have been there. Positioned in arms reach was a container full of baby powder and a pump bottle filled with baby lotion. Mentally, he was scrambling to figure out not only why this stuff was hidden under his bed, but why his body knew exactly where to find it. 

Stanley’s body, however, did not have the same reservations that he did, as his hands quickly seized the bottle of lotion and began to squirt copious amounts onto his genitalia. With expert precision, he spread the baby lotion around as if he’d been doing this for years as he made quick work of coating both his front and rear in a hardy layer of lotion. His antics with lotion, though, didn’t stop there as he then squirted out a large amount of the bottle onto the front of his diaper, knowing well and good how his penis would react to such slippery confines. 

Setting the lotion down, Stanley’s hand pounced on the baby powder. As he picked it up, a small poof came out the top and wafted into his nose. The smell was so strong and was certainly a nostalgic one, even if it was very much unwanted, but it was nothing compared to the feel. Wasting zero time, his body dove right in, sprinkling so much powder over his crotch and butt crack that he could no longer see even a speck of skin. 

Then came the moment of truth. Stanley grabbed the front of the diaper and slowly eased it forward, his penis making contact with the girthy pile of lotiony goo that rested in the diaper. The cold of the lotion caused him to shiver but was soon replaced with feelings of unparalleled euphoria as he rested the hem of the diaper on his stomach. Soon after, he was quick at work, grabbing the side tabs and taping himself into the diaper with such ease that it scared him. He didn’t even have to reapply the tapes to get the perfect fit. 

Placing a hand on the front of his bulky diaper, Stanley shook and bucked his hips as if he could cum at any second. Every slight movement reminded him of the lotion that smothered his cock in moist softness. Somewhere deep in the back of his mind, he wanted nothing more than to sit on the floor and lean into what was building itself up to be perhaps his most intense orgasm ever. 

Once again, though, Stanley’s body had other plans. Picking himself off of the floor, Stanley winced as the baby lotion shifted around, caressing his diaper-swaddled dick. It was insane how much he wanted to reach down and rub himself silly. Mercifully, his body appeared to be holding back, at least for now. 

Stanley’s heart dropped as his attention moved from his diaper to the bed, where the crumpled-up tank top was stationed. Crawling onto the bed and picking up the top, a tear fell from his eyes as he witnessed himself placing a girl’s form-fitting shirt onto his torso. As the tank top was unraveled across his chest and tummy, he was mortified to find that he had failed to notice the glittery text on the front of the shirt that read, “Sissy Baby Bitch!” He was so shocked by those simple three words that his mind went blank while his body placed the two dainty, frilly socks onto his feet, completing his new ensemble. 

“WHAT THE FUCK IS WRONG WITH ME?!” screamed Stanley in his thoughts as his body looked over at the mirror with an expression of pure bliss on his face. Too focused on what was happening to him, he hadn’t even realized that all the while, he’d been grinning like an absolute idiot with his docile eyes glazed over. Sadly, “Sissy Baby Bitch” was turning out to be far too befitting a title given his atrociously infantile appearance. 

After staring at himself in the mirror for an embarrassing amount of time, Stanley’s eyes glanced down at the pacifier in the center of the bed. Rolling over with his arms and legs flailing haphazardly, he clumsily took the pacifier and plopped it in between his lips. 

The feeling of suckling on a binky was more satisfying than Stanley cared to admit, but damn did it feel good. He couldn’t explain it, but a buzzing in his teeth had been building since the beginning. And now that he was nursing a rubber nipple between his gums, that buzzing had seemingly transformed into an erroneous zone that only fueled his overwhelming desire to rub himself until he climaxed. A wish that was on the horizon, as he set his sights on the final gift from Amber’s box of fun. 

Nestled near Stanley’s pillows was the key to his orgasmic salvation. Laying himself out across the bed, Stanley took hold of the Magic Wand that only minutes ago he was smugly imagining Amber using on herself. A memory that felt like a lifetime ago at this point. 

Pressing the on-button, Stanley relaxed his head on his pillow and bit down hard on his tongue with shivering anticipation. Slowly, but steadily, his hand raised the vicious vibrator and gently lowered it onto the pointed tip of his diaper. 

“MMMMMMMMMMMMM!!!” Stanley moaned into his pacifier as the Magic Wand squashed down on his lotion-loaded diaper. His body pulsed as if he was going to cum on first impact. However, for some reason, even though he felt so close to the edge, he couldn’t seem to climb his way over. At least, that was the case, until another, far more sinister sensitivity rippled across his tummy. 

Puzzled, Stanley’s weakened, but still conscious brain naively wondered if he’d eaten something foul. Regardless, his focus had very suddenly shifted to his aching gut, feeling the matter inside sloshing around with every thrust of his hips. 

Suddenly, the two contrasted, yet connected sensations began to build with one another. Stanley could feel that his body was at the point of no return as neared orgasm. Simultaneously, he could also feel a strong, ever-growing pressure in his bowels, which were begging for relief. 

In an instant, Stanley’s vision went black and his ears went numb. The only sense that he could recognize was touch. Powerful electric waves shot forth from his cock and spread throughout his entire body, causing him to convulse in a state of pure ecstasy.  

At the same time, in spite of how much willpower he was putting into holding his sphincter closed, his body could no longer restrain itself, lost in the pleasure that racked his body. 

BLOOOOOOOOOOOOOOOOORRRRRRT!!! 

“MMMMMMMMMMHHHHHHH!!!!” 

Stanley’s hips jolted into the air as his body evacuated bodily fluids from both his penis and anus. Wave upon wave of extreme pleasure enveloped his entire body as his cock refused to let up, pumping a bucket’s worth of cummies into his nappy. A feeling that was only amplified by the pressure that his near hypermessing was putting on his prostate. It felt like his body was churning up semi-soft mush faster than he could get it out.  

By the time his body had finished expelling all the spunk and poop that it could, Stanley was left paralyzed on his bed with his hips submerged in his own waste. He was beyond horrified with his own actions but could do little more than pant heavily as he came down from the mountain top of orgasms. 

RATTLE! 

Stanley’s ears suddenly perked up as he heard someone just outside of his apartment fiddling with his doorknob. He wanted to jump up from his bed and hide, but his body wouldn’t even so much as look in the general direction of the door. All he could do was wait for the inevitable. 

CLICK! 

The door creaked open and Stanley heard footsteps near his bed. He stretched his peripheral vision as far to the side as he could, but his eyes couldn’t get a good enough focus on the figure moving towards him. Soon enough, though, he wouldn’t have to guess who it was as their familiar voice was the only hint he needed. 

“Well, well, well,” said Amber with a gleeful smirk on her face, “I told you not to open that box, didn’t I? Too bad I knew for a fact that you’d be far too tempted to listen to even one simple request I made.” 

On the inside, Stanley was fuming. “Amber did this?! How on Earth was she able to pull something like this off?!” he thought, wanting nothing more than to jump up from this bed and berate her for treating him so cruelly. Sure, he wasn’t the world’s greatest boyfriend, but this was humiliation on a whole other level. 

Unfortunately, on the outside, Stanley couldn’t get the stupid, excitable grin off of his face. It was like it was sewn onto him. Even though his cheek and jaw muscles were on fire, the smile wouldn’t subside. 

Sitting on the bed next to Stanley, Amber finally came into view, dolled up in a short, sexy party dress. No matter how many times Stanley had asked her to wear less revealing clothing so other dudes didn’t gawk at her, she never listened to him. 

“Why so glum, sweetie? Mommy knows how much fun you were having before I came in,” said Amber, delighted as she watched Stanley’s face color deepen by several shades of red. Reaching down and petting his hair she continued, “That’s right! Mommy Amber heard all of your adorable squeaks and noises you made. These aren’t very thick walls, after all. I bet you’re still super confused about what’s going on, aren’t you?” 

stanley couldn’t nod his head in confirmation, but the look in his eyes was all Amber needed. Taking a remote out of her pocket, she pressed the button, causing a very calming sound to echo throughout his room, clearly sourced from under his bed. She giggled, “After I suspected your unfaithful ass of cheating, I did some digging and found out you’ve not only cheated on me but several of my sorority sisters as well. So, we devised a plan. During the last few days before we split, I set up your room to be a regression dungeon for you. It was so easy to do and you took to the hypnosis tracks like a fish to water.” 

Amber grazed her fingers across his face before homing in on his binky and pushing down on it slightly. The forcefulness of her actions, as little as it was, caused him to let out another woefully horny moan. She’d really done a number on him. 

“Eeeeee! You turned out even better than I expected! I knew creating that tether in your brain between diapers, pooping, and cumming would be the real kicker,” gloated Amber as she watched the front of Stanley’s diaper slowly rise, “Not only that, but I made sure to add something extra special to your subliminals.” 

The moment she finished her sentence, Amber reached down and grabbed onto his stiffening cock, forcing a gasp out of him. She snickered, “Any girl that makes you make cummies in your diaper will instantly become a Mommy Mistress in your mind that you must obey until she graduates from university. Doesn’t that sound like so much fun, Stacey?!” 

If Stanley could scream, he would’ve shattered every window and piece of glass in this building. Sadly, his internal reaction made no difference, as his body nodded his head delightfully.  

Setting down the duffle bag that she had slung over her shoulder, Amber opened it up and pulled out a massive, pink ball of fabric and frills. Staring at the mass in his ex’s hands, Stanley couldn’t make out what she was holding, though the evil look in Amber’s eyes told him whatever it was couldn’t be anything good. 

Lifting up Stanley’s legs, Amber inserted both of his feet into the round, cushiony orb that, to Stanley, felt like he was being fed to a silky pillow. She then slowly moved it up his calves and thighs, allowing the sensual fabric to tempt his impending orgasm even more. 

By the time it had reached Stanley’s pelvis, it had become all too clear what he was wearing. It was some sort of giant stuffed diaper that was designed to mimic a real one. Only this thing was far bulkier than an actual diaper, jutting out nearly a foot in every direction. As his hips rested back on the bed, his back was forced into an awkward, slanted position, thanks to his new cloth nappy. 

“How do you like the waddle spreader?” asked Amber, patting him on the front of his diapers, “It’s one of the expensive ones from CrissBaby, so you’d better be grateful! It’ll certainly keep you crawling on all fours with how ungodly thick it is.” 

With a sinister expression, Amber crawled up onto the bed and sat down on Stanley’s diapers, squishing him tightly within his mushy, cushy prison. She then took hold of the still buzzing vibrator, forming a sadistic idea in her brain. “Why don’t I show you just how easy it's gonna be for every one of my sisters to make you their widdwe sissy bitch!” she said with a weighty cackle as she lifted the front of Stanley’s waddle spreader and shoved the vibrator in between the silky cushion and his tremendously full diaper on full blast. 

Stanley barely had even half a second to react, his mind being driven up to the brink of melting in an instant. Just like before, he could already feel pressure building in both sides of his pelvis as the need to cum and the need to shit were intertwined so seamlessly. Making matters worse, Amber began to bounce up and down on his diapers, humping the wand against his insanely sensitive member. He didn’t even last half a minute before the inevitable happened for a second time. 

SPLUUUUUUUUUUUUUURRRRRCCH!!! 

Gasping for air, Stanley’s body quivered involuntarily as he filled his diaper up from both ends, emptying a gargantuan amount of feces and sissy stickies into the safe confines of his pampers. Prolonging his mind-breaking climax was the Magic Wand, pleasuring his impossible to satisfy penis even after he’d hit his point of no return. 

In an act of mercy, Amber only let Stanley endure another two orgasm-fueled messes before plucking the vibrator out of his waddle spreader, “That’s enough for now. Don’t want you blowing out in my car after all,” she said as she reached into her back pocket and pulled out a pink collar with the name, “Stacey,” written in bold, gold letters on the front. In no time at all, she had it wrapped around his neck and snapped shut, reinforcing his brand new name. 

Defeated, Stanley resigned himself to his sissified fate. There was nothing he could do. He was a prisoner of his own body, which offered him zero autonomy over his words or his actions. It was as if his body was on auto-pilot. And no matter how much he tried to claw his way back, whatever Amber had done to him had a firm grip on him. 

Attaching a leash to the collar, Amber guided Stanley to his feet, his body trembling with every movement. She was almost surprised that he was able to hold himself up, though couldn’t help but giggle at how far apart his legs were. With the leash in hand, she marched towards the door with Stanley toddling behind, still with a sweet smile stitched onto his face. 

“I’m glad you’re so thrilled about these new developments, Stacey. You’re gonna have a blast at my sorority’s weekend-long slumber party!” said Amber, pinching his cheek as they stepped into the hallway, “Maybe you’ll fit in with my sisters so much that they make you the house sissy, and new members each year could become your Mommy Mistresses. Then you can be the sissy you were always meant to be for generations to come!” 

Stanley’s body reacted with extreme jubilation at the idea, regardless of his true mind’s actual thoughts. As he heard his apartment door shutter closed behind him, he internally offered a sorrowful goodbye to the alpha male life that he’d cultivated over the last few years. No longer would he be attending Thirsty Thursday and hanging out with his bros. His future now was filled with dresses, diapers, and female domination; a thought that he could already tell was pitching yet another tent in his diapers. 

THE END.