New Clothes, New Life, New Sissy (Patreon)

Nothing left Chase so unnerved as the feeling he got when he was alone in his building's laundry room. The cramped room was tucked away in the basement level. The moisture and lack of windows made for a dangerous combination. It was rare that Chase didn't smell something terrible when he was down there; but something was different. That fateful day, when Chase went downstairs, the basement looked brand new. Which was odd given how Chase hadn’t seen any construction. The laundry room looked state of the art with new machines, clean counters, and even a few vents to help with the moisture. He was surprised to find someone else down there as well. A woman with a short black bob stood with her back to Chase when he entered. She had a shapely figure, well displayed by the short skirt and tight long-sleeved top that she wore. She turned when Chase approached and looked at him through a pair of thick-rimmed glasses with a smile on her face. 

“Hello, Chase. Good to see you using the new facilities,” the woman greeted Chase.

“Do I know you?” he asked in reply.

The woman looked him up and down. Chase was a man of average height and build with dirty blonde shoulder length hair. His blue-green eyes were very pretty in the right light and the woman before him stood in such a way that she would very much agree. “You should. I own the building. My name is Candice.”

Chase felt a chill go down his spine. Candice was beautiful, but something about the way she looked at him made Chase feel as if he were in danger. She either wanted him, or wanted something from him. Chase couldn’t help but be intrigued too. It’d been a while since he had last been with a woman. He wasn’t one to jump the gun on stuff like that, but the feeling in the air was palpable. 

“Hey, Candice,” Chase replied. He did his best to appear calm. “So you own the building, huh? Must have been a lot of work fixing...this place...up…” Candice approached as Chase spoke. She eventually grew so close that Chase had trouble concentrating. Her breasts were incredibly large and very near his face. It was hard not to stare. 

Candice took notice. “Wish yours were this big, little girl?”

Chase was taken aback. He hadn’t expected such a question. The laundry detergent in his hand dropped and stained down the front of his pants. “Dammit. I’m not a little girl! I’m a grown man…”

“A grown man, huh? You can’t even do your laundry without spilling something. It looks like you peed yourself…” Candice teased. She then gently grabbed Chase by the wrist and pulled him toward herself while she stepped back at the same time. They stood in front of what looked like a laundry machine with no accessible door. 

Chase was unsure of what it could be for, but he didn’t care. He didn’t even care too much about Candice’s attitude. All he cared about was the intensity he felt in that moment. “You’re so pretty…” he told her. 

“You’re sweet. You really think so? Do you wanna fuck me? Is that why you’re tinting your pants right now?”

Chase blushed profusely. He had not thought his erection noticeable. “Uh...I mean yeah…”

"Perfect!" Candice exclaimed, "So then it's time we began. We can't have you dirtying up anymore clothes now, can we?" She reached into the curtain next to her. With some effort, the attendant managed to lower a lever hidden out of sight. A loud clunk followed and Chase found himself struggling against several white-gloved metal arms. They dragged him backward to the strange machine. The door on the front, once seamless, split open down the center to reveal a sizable conveyor belt. 

Chase gripped either side of the doors with his hands. He weakly kicked the arms with his free leg. "What the fuck?! S-Stop this! Let me go!" Chase pleaded.

"You let go first," Candice replied casually. "Nothing bad is going to happen. It's just going to take care of you and your little problem."

"Wha--?!" Chase's breath was taken from him in an instant by a firm hand to his chest. Candice pushed him further back past the doors until Chase's ass dragged against the moving conveyor. "No no no! Puh…Ple--" Chase tried to stammer out a plea but lost his strength mid-sentence. The arms won out and he was dragged backward until he was flat on his back on the conveyor. 

"Have fun, Chase!" Candice shouted over the cacophony of metal. "You can thank me later."

"Fuck you!" Chase yelled in reply. Candice missed it. The doors had already sealed shut. Chase was helpless but to ride along the conveyor. He was pinned to it, unable to do little more than strain against the hands. "Let me go!" He shouted at them. Chase knew it to be a fruitless act, but it felt better than nothing. He continued to shout as more hands appeared. Many of them carried scissors. For the first time in years, Chase screamed. 

The hands zipped toward his body. The metal of their blades touched his skin, but did not cut him; instead, they cut him free of his wet clothing. Each article was removed until Chase was left completely naked. Chase stopped his screaming the moment he realized what happened. His wall of manly bravado reappeared and he cursed at the hands as they cut his clothing to pieces. "What the fuck kind of laundry room is this?! You're supposed to wash those! They're expensive!"

"Goodness!" said a familiar voice, "Do you curse like that always? That's no way for you to behave!" Lights flickered on around Chase and Candice could be clearly seen from a viewing window back toward where Chase had first entered the machine. "Well don't worry. This machine can do far more than just handle your clothing situation. It's also great at behavior correction."

Chase stared at Candice through the glass. His mouth was wide open in shock. "I'm sorry…? Behavior correction? What the fu--" Chase's words were cut off but the sudden insertion of a large pink bar of soap. He tried to spit it out but it was far too large and his teeth felt stuck. Suds formed around the corner of his mouth as he tried to complain and plead for help. It all sounded like garbled nonsense. Next, Chase was flipped over on the conveyor. His face and knees were pressed into the belt while his bottom was raised into the air. Several of the hands took turns spanking his bare backside. Chase babbled around the soap. His face was beat red and he clearly couldn't stand a single second of the punishment. 

"Such naughty language!" Candice scolded him. "Looks like your clothes weren't the only things that needed cleaning." She watched Chase get spanked with great interest. Much to Chase's dismay, Candace had some amount of control over the machine. She flipped several switches as she watched him. A devilish grin appeared on her face. "Don't worry. I'll make sure you learn how to properly behave."

Chase looked back to see several more hands had appeared with various implements in hand. A hair brush, a paddle, a pink flip flop, and more. The hands took turns spanking Chase. Each tool hurt more than the last. Humiliated and in horrible pain, Chase was quickly reduced to crying around the soap. His chin was covered in a soapy mixture of tears and drool. He pleaded around the soap for it to stop, but neither the machine nor Candice seemed to care. It wasn't until his bottom was beet red that the hands finally relented. Unfortunately for Chase, it did not mark the end of his ride on the conveyor. 

The hands that had spanked him so intensely dropped their implements and retreated back under the conveyor. Chase looked back, relieved, only to spot a hand that approached his backside with an old-fashioned rectal thermometer in its grip. "Nuuuuuuuh!" Chase portested, but it was too late. A lubricated finger had already inserted itself into his bottom. It roughly massaged his insides until Chase's bottom was thoroughly lubricated. As soon as the finger left, the thermometer was inserted. Chase grimaced and grunted loudly in discomfort, but could otherwise do nothing but lay still as the machine took his temperature. 

After what felt like an eternity, the hand removed the thermometer and inspected it. The relief Chase felt when it left, seemingly satisfied, was immense. So much so that when the hand returned with an enema kit, Chase was in shock. He had not expected that things could get any worse. Surely being stripped naked and spanked in front of a beautiful woman was bad enough? The machine thought otherwise. Though it's intention was not to humiliate. That was only a by-product of the process Chase found himself stuck in.

Same as before, Chase struggled against the arms in vain. He clenched his cheeks and wiggled around as much as he could, but the machine won out. The enema was inserted into his backside and his bottom was filled with lukewarm water. Chase cursed around the soap. The humiliation was bad enough, but the discomfort grew with every second and threatened to overwhelm him. 

"What was that you said earlier, Chase?" asked Candice. "'I'm not a little girl', huh? That's cute for someone who's on the verge of messing himself."

"Eh jus wahder…" Chase protested weakly. He was right. It was mostly just water, but the pressure in his lower stomach made it feel like so much more. His cheeks burned a bright shade of red as the pressure continued to build. The hand had only just finished and already it felt as if he might burst. Desperate for help of any kind, Chase looked around the conveyor room. To his dismay, he spotted a bright pink princess training potty coming up on his right. "Nuh! I'm nah gon-na" Chase babbled.

The hands and his bowels both did not seem to care. Chase was in so much discomfort that he did not fight when the hands lifted him from the belt and placed him on the training potty. So desperate to hold onto his dignity was Chase that he clenched as tight as he could. He refused to be brought so low. Unfortunately for him, the hands were used to unwilling participants. A white-gloved palm pressed into his lower stomach firmly. Chase whimpered, then released his bowels into the training potty. He stared down at his shame only to realize that the potty was decorated as well. Words on the front, between Chase's legs, declared the potty to be 'For Big Princesses Only'.

Several pairs of hands clapped for Chase and his embarrassing act. They then immediately lifted him into the air and gave his backside a painfully thorough inspection. He was dangled with his back turned to Candice. The thought that she had a clear view to his humiliation was enough to make Chase's bottom lip tremble. He squirmed in the arms, teary-eyed, as one particularly eager hand used a speculum to further inspect Chase's bottom. The dangling man kicked and squirmed as the cold metal pressed its way in and spread him wide. 

After a few more minutes of inspection, Chase was unceremoniously dropped back on the conveyor. Before he knew it, more arms grabbed him yet again and dragged him down into a tub of sweet smelling water. Chase wriggled free, the soap in his mouth finally gone, and gasped for air. He was surrounded by pink bubbles. Any attempt to escape was immediately met by hands grabbing and spanking Chase. They forced him to sit in the tub as they scrubbed him clean. The hands washed his hair as well. They used flowery products that left Chase smelling like perfume. By the time he noticed that his hair had been dyed it was too late. The hands kept him far too busy to bemoan his new pastel pink hair too much. 

Hands carrying razors, shaving cream, and baby oil quickly surrounded Chase. Even with him being wet and resistant, the mechanical arms kept Chase under control easily. A firm hand kept Chase's face perfectly still as a couple more got to work ridding him of any facial hair. More hands did the same across the entire length of his body until he was left completely hairless save for his pink hair. Not even the hair of his manhood was spared. Chase looked almost like a doll. 

"No more!" Chase begged, "Please!" 

The hands would not listen and Candice was nowhere to be seen. Chase was forced back onto the conveyor and sent further down the line feet first. Positioned as he was, Chase was unfortunate enough to witness his next humiliation from a distance. A large, pink-and-white rocking horse would be Chase's next endeavor. As they neared it, Chase thought to escape, but the hands were quicker. They did not bother to punish him and instead placed him square onto the saddle of the massive rocking horse. 

Heavy, metal clamps popped out of the horse and secured Chase to the seat by his wrists, waist, ankles, and neck. A large, pink pacifier was brought before him. The guard was modified so that a tube could be inserted through the front. The nipple was far larger than normal and was shaped like an erect cock. Chase clamped his mouth shut. There was no way he'd endure such humiliation. In retaliation, something beneath the seat shifted. Chase felt something round and hard press up against his anus. It waited there as if to see what he would do. With no desire to test the machine, Chase opened his mouth. The cock pacifier was stuffed in immediately. Chase almost gagged. He tried to spit out but it had already been secured to his head like a gag. The horse started to rock back and forth slowly beneath Chase. A strange concoction then filled the paci-gag's tube and started to drip from the tip of the cock into Chase's mouth. It tasted alright and he was thirsty, so Chase decided to drink some. Just a little. As soon as he did, several monitors appeared from the wall before him. The cock started to spasm in his mouth. It flooded Chase's throat with the sweet liquid until he was forced to guzzle it down. Before long, Chase actively sucked on the cock as if it were a pacifier's nipple. With a rhythmic timing he suckled the seemingly endless formula down. Chase's eyes grew heavy and his nipples erect. Words started to appear on the screen before him but it was difficult to read. It was difficult to do anything other than suck.

Estrogen Levels - 85%

Testosterone Levels - < 0.1%

Bladder Control - 72%

Bowel Control - 86%

Arousal - 64%

Willpower - 45%

Physical Strength - 10%

The numbers changed with each passing second as more and more of the special formula poured down Chase's throat. Before long, Chase drooled all over himself. His cock was painfully erect and stood at attention as the machine entered its next phase.

Several devices and tubes appeared from the ceiling and the rocking horse. A pair of milking devices attached themselves to Chase's puffy nipples and suctioned themselves to him. A similar looking device attached itself around his cock. Together, they worked as one to milk Chase of his cum and the breast milk he had started to produce just moments prior. What little of Chase remained in his fogged over mind was horrified to find that the tubes that led to these devices also led to a large baby bottle that sat on a table next him. He was too weak and stupid to realize just what was in store for him. What Chase did notice was the massive growth his nipples had undergone. His once flat chest had grown into small breasts that continued to grow in size as he downed more of the formula. Even knowing that, Chase did not stop drinking. He couldn't. The cock in his mouth spasmed every few seconds and threatened to drown him if he didn't obey and drink every last drop. Of course, the machine would not let him die. Chase was too stupid, too horny, and too obedient to stop. The formula threatened to change him completely and some part of him now craved it. That same part nearly moaned aloud when the hard, round pressure on his anus suddenly burst upward and filled his ass. Once inserted all the way, the massive dildo began to vibrate. A secondary tube from the milking machines fed the mixture into it and soon the large cock was spasming in Chase's ass just like the pacifier in his mouth. 

Chase's body seemed to move against his will. His ass bounced up and down on the cock, eager to take in as much of the vibrating shaft as it could. His head moved back and forth as if he was giving his pacifier oral. The motions combined cause the large horse to rock back and forth. Tears formed at the corner of Chase's eyes as he tried to fight his increasing urge to give in and let the machine use him as it pleased. Not that he had a choice. There was no escape. He wasn't strong enough to break free and his urges got worse with every second. Just when it seemed he might be able to muster the strength to stop himself, headphones descended from the ceiling and were placed on his ears. Monitors appeared in front of him. So many that he could not look at anything but a screen with his head stuck forward as it was. Words were whispered into his ears and slowly grew in volume as the screens turned on before him. Swirls of pink were introduced to a flat white image. This continued until all of the monitors displayed a hypnotic pink swirl. 

Chase fought against the machine mentally as he did physically, but it was a losing battle. The words grew in volume and his eyes were fixed forward. Chase did not look at any particular screen; instead, he simply let the swirling images fill his then empty mind. The swirling pattern reflected in his eyes as a lewd, blissful expression overcame him. Chase knew then what it had in store for him. His mind was already so corrupted that he listened eagerly to every single word the sissy baby hypnosis track told him.

You love your diapers. You want to use them. 

You love your paci. You'll always need something to suck on.

You're a silly little sissy. You're not a man and you never were.

You're a dumb, drooly baby. You couldn't put a square peg in a square hole if you tried.

You're a bimbo slut. You love pleasing cock and being a cum dump.

Your name is Samantha. You're a diaper-dependent sissy bitch and you absolutely love it.

The humiliating reprogramming continued on without pause. All the while, the numbers on the 'Progress Monitor' changed until it was clear that the transformation was nearly complete. Chase, now Samantha, took in every word, unable to do anything more than rock on her horse and let the machine use and change her as it saw fit. As she rocked, a couple hands approached her head and did her pink hair up in a pair of childish pigtails with lacy ribbon. 

Once the headphones were removed and the swirling monitors were put away, Chase was completely gone. Samantha couldn't even remember being a respectable adult. All that floated around in her near empty head were the words put in there by the machine. It had completely reprogrammed her. Defeated and more helpless than ever, Samantha did not fight the hands when they removed her from the horse and placed her back on the conveyor. Samantha laid still on her back with her legs spread and her arms at her side. She sucked on her fingers, almost in tears over having lost her paci-cock and vibrating dildo. The relief she felt was so intense when the hands returned with diapers and a plug in tow, that Samantha's cock twitched eagerly and threatened to ejaculate then and there. The plug, a large pink one with the words 'Sissy Paci' written on the top, was put to the side as a particularly large hand approached Samantha's backside with its pointer finger covered in vaseline. Samantha let loose a throaty moan as it inserted itself into her bottom. The finger made sure to inspect her thoroughly before it removed itself and inserted the large plug. Samantha, so excited to have something so thick and degrading in her ass, ejaculated all over her tummy from her constantly hard cock. The hands around her wiped her clean then covered her diaper area in baby oil, powder, and lotion; before taping her into a big fluffy diaper. The disposable diaper was just as humiliating as the plug. The thick, pink diaper was decorated with hearts, princesses and unicorns. It was quickly followed by a bright pink pair of lacey rubber rhumba panties. As a finishing touch, a pair of vibrating clamps were attached to Samantha's puffy pink nipples. Samantha moaned and wriggled on the conveyor as it started to move forward again. She babbled and whimpered to herself while she came in her diapers again and again.

At her next stop on the conveyor, the hands zipped over to Samantha with tons of various pink and frilly clothing. They seemed to debate amongst themselves as to what to dress samantha in. Eventually, they settled on a particularly provocative outfit. The hands started with a pair of bright pink fishnet leggings that came to just below her diaper. A corset was then added that, when pulled tight, made Samantha's new D-cup breasts look even bigger. A pink, frilly miniskirt was then yanked up her legs. The hands had some difficulty getting the skirt over the diaper, but eventually managed. The pressure against her diaper was enough to cause Samantha to nearly cum again. As if on queue, her Sissy Paci plug started to vibrate and Samantha could do nothing but shoot another load into her already sticky diapers. Some of the semen escaped from the top and a small semen stain appeared on the front of her skirt. Next, a tight pink shirt covered in hearts was then pulled over Samantha's head. The low cut top just barely managed to keep her nipples covered and left little to the imagination. Especially when the hands gently tugged down the shirt so that her vibrating clamps were left on full display. Another paci-cock was introduced to the outfit by a pink ribbon attached to her top. Samantha immediately took the paci into her mouth and sucked on it eagerly. She was sad to discover that it would not ejaculate in her mouth like the old one, but was just happy to have a cock to suck on again. The hands, pleased to see Samantha acting so depraved, then added a small bib around her neck that read 'Sissy Cum Guzzler'. It was too short to hide the majority of her cleavage and the vibrating clamps, but was just big enough to make sure no one would mistake her from anything but the sissified cum guzzler that she was. Finally, as a finishing touch, the machine slathered her face in whorish makeup and painted her nails bright pink. 

With the sissy baby dressed, the conveyor started again. Samantha had reached her final stop: a large crib filled with soft blankets, sex toys, and stuffed animals. She was deposited into the crib and tucked in like the tired rugrat she was. Restraints clamped to her wrists and ankles. They were pink, plastic, and more toys than actual restraints. Weak and horny as she was, they were all that were needed to keep the sissy baby in line should she somehow remember her old self. A hand entered the crib with a vibrating wand. It inserted the wand into her fishnet leggings and pressed the vibrating head hard into Samantha's diapers. It then switched it on to high and Samantha was left a moaning mess. She came again and again. Each time she squirted more semen into her diapers and occasionally stained her skirt even more until it was abundantly obvious that she had cum all over herself. Her pacifier was then removed and the bottle of breastmilk and cum from before was stuffed in her mouth before she could grow upset. Hearts appeared in her eyes as she happily downed the 'special' formula. There, stuck in the crib and blissfully guzzling down her own breast milk and cum, Samantha slowly drifted off to sleep. Even in her sleep her cock continued to spasm and soak her diapers. 

Around Samantha, the conveyor was retracted and the room transformed. The hands went to work meticulously placing various pieces of nursery furniture and toys around the room. Her rocking horse from before was added along with a mobile decorated in toys both childish and adult in nature. Anal beads and vibrators dangled above her as the last bit of formula was drained from the bottle. The empty container fell from Samantha's mouth and clattered to the floor just in time to be picked up by her new mommy, Candice. The older woman looked down at Samantha through the bars with a smile on her face. The smell of baby powder and urine filled the air. Samantha's skirt was plenty short enough to make it clear that she wet her diapers in her sleep. Candice was beside herself with delight. Her first transformation was a success and, while she had intended to trap more in her web, she decided to keep Samantha as her baby rather than sell her off as she had intended. Chase made an adorable sissy and would make her happy as Samantha. Candice was sure to have some fun and she couldn't wait to get started.

---

"Tell mommy what you want, sissy." said Candice. She stood in Samantha's nursery, her massive cock straining in her panties. Samantha knelt on the floor next to her, dressed as her sissy bitch. There was a noticeable bulge in the front of her diaper. Drool dribbled down her chin as she stared at her mommy's cock.

Samantha whined softly. She massaged the front of her diaper and tugged on Candice's dress. "C-Can I pwease fuck you mommy?"

"Does the little sissy want to act like a big man again?"

Samantha shook her head profusely. "No mommy! I'm a horny little sissy that wants to squirt in her mommy. A dumb sissy baby that likes squirting with her plug in!" Her voice was high pitched and she occasionally spoke with a babyish lisp. It was something her mommy often praised her for. Candice liked using positive reinforcement.

"Show mommy your dick, sweetie. Show me how bad you want it."

Samantha raised the skirt of her tutu even though it did not hide anything. She tugged her diaper down around her thighs and freed her erect cock. "Pwease mommy!"

"Alright, sweetie. Mommy will take care of your little problem." Candice lowered herself onto Samantha's pastel play rug with her butt raised. She tugged her lacy black panties down just below her cheeks and spread her asshole. Samantha eagerly climbed atop her and pushed her cock in. Candice was used to anal, the sheer amount of precum that coated Samantha's cock was more than enough to lubricate her hole. 

Samantha grunted and whimpered as she fucked her mommy. Candice remained silent for the most part. She spoke only to tease and encourage her little sissy. She made sure to make it clear that it was purely for Samantha's benefit. Her cock was too small and sissified to truly pleasure her mommy. It was no surprise that she came within a couple minutes. "Fank oou...mommy…"

"You're welcome, sissy," said Candice. "Now get on all fours so mommy can show you what a real dick can do."

Samantha shivered from head to toe. Getting fucked by her mommy had been her goal all along. She enjoyed being used more than anything. It's why she loved her rocking horse so much. Samantha rode it daily, and it stretched her plenty big enough to fit her mommy's massive member. She let Candice guide her to the floor and press her face into the carpet. After a moment of playful teasing, Candice was on top and inside her. Not ten seconds later and her cock was dripping cum into the crotch of her diaper. The saggy, soggy padding swung back and forth with each forceful thrust. Samantha was in heaven. She still couldn't believe she had ever been a man. Her mommy told her as much, but she still didn't believe it. Samanatha was a sissy bitch through and through. She knew this. And when her mommy came inside her, Samantha drooled all over herself as she begged her mommy to keep going and keep using her like a sex toy. 

Candice was all too happy to oblige. "Of course, sweetie. You know I love spoiling you rotten."

Eventually, once they were finished. Samantha's diaper was yanked back up just in time for her to soil herself heavily. The diaper sagged profusely and Samantha happily bounced up and down in her cum-soaked, messy padding. Candice then picked her up and put her on the changing table. She cleaned Samantha thoroughly with wet wipes and made sure to get deep in her butthole just like her little girl liked. The sissy baby then got her special paci back. She moaned softly as the large plug was inserted and stared blissfully at her mommy as she was lathered in baby oil and powder. 

"It's almost time for little sissies to nap," said Candice. "Are you a little sissy?"

Samantha nodded with excitement. "I'm a little sissy!"

Candice smiled. She gently lifted Samantha up from the table and brought her over to a rocking chair. Candice sat down and placed her sissy in her lap. She then tugged her top down and exposed her nipples. Samantha latched on immediately. Her eyes glazed over and she looked off vacantly as she suckled from Candice's breasts. Candice lovingly doted on Samantha and gently rubbed her diapers. The sissy in her lap clearly ejaculated multiple times before it was over. She even wet herself as they neared the end. An absolute sissy baby through and through. It was then that Candice carried Samantha to her crib. As usual, a vibrator was strapped to her thigh and turned on the highest setting. Candice cooed and gently stroked Samantha's hair as the sissy came in her diapers again and again. Only once Samantha's breath slowed and her eyes drooped to Candice remove her hand and take her leave. She smiled at Samantha as she walked away. Candice still couldn't believe how lucky she was. Samantha had turned out to be the perfect sissy baby.