Dear Diary (Patreon)

Chapter 1 

"Listen, Sam, I get it. I've been through plenty of break-ups. I know how hard it can be to push yourself out of bed and be a fully functioning adult when you're this heartbroken but you have to. You're never gonna get over her like this."

Sam's friend Jacob rifled through a banged up cardboard box full of old video games. His words sounded genuine, despite how distracted he looked.

Sam scoffed. "Is this how you get over break-ups, Jacob? A yard sale?" He flipped through a couple books on the table next to him. "Are we sure this is a yard sale? There's no one even watching the stuff."

"Pretty sure, dude. And just so you know, smart ass, it's not just yard sales. It's getting out and doing stuff. Keeping busy and keeping your mind off the negatives."

A particularly old book caught Sam's eye. A diary. The pages had discolored from age but were mostly blank save for a few in the front of the book. "Easy for you to say. Girls obsess over you. When do you not have a new girlfriend hardly a month after the last." Sam glanced over the pages. Nothing too interesting it seemed. Just an old daily journal.

"Girls obsess over me because of my confidence." Jacob pulled a dusty cartridge from the box and looked it over. "You could stand to learn a thing or two from me, ya know." Annoyed, Jacob tossed the cartridge back in the box and made his way back out of the yard. "Let's just go before I regret trying to help you anymore."

Frustrated, Sam nearly threw the book at Jacob. He grimaced and let the book drop to the ground. "Whatever." The diary landed on Sam's foot. He looked down to see that the book had opened to the last written page. In large print it read: 'Sam picked up the diary and took it home.'

"W-What…?" Sam bent down and scooped the book back up. He rubbed his eyes and looked again. The words remained. The ink looked fresh.

"Come on! It's starting to rain." Jacob called.

"Alright already!" Sam responded. Curious about the book, he looked for a price tag. When none was found Sam looked around for the owner. And when they too were missing, Sam pocketed the book. 

"What's with the book?" Jacob asked.

"Just an empty journal. Figured it might help keep me on track."

Jacob smiled. "There we go! And here I thought you were hopeless."

The rain that had started as a trickle quickly turned into a downpour. As they lacked umbrellas, the two hailed a cab home and went there separate ways. Jacob to his girlfriend's place. Sam to his own home. The journal was all he could think about. He was determined to learn more.

---

'Sam picked up the diary and took it home.'

The ink was dry. A bit smudged from the travel but still legible. Sam sat at his desk, his eyes fixated on the page. In his right hand was a black pen. He had no idea how the writer had known his name and that he would be at the yard sale at that time. As far fetched as it seemed the only explanation that made sense to Sam was a supernatural influence. There was no other way. And so, Sam decided to test this theory. With a shaky hand he placed pen to paper and wrote the first thing that came to mind.

'Sam found a dollar under his desk.'

Sam slid his chair back and squinted at the dimly lit underside of his desk. There, under one of the desk's legs was a crumpled dollar bill. Sam's eyes widened at the sight. He couldn't believe it. In fact, doubt set in almost immediately. Was he really so foolish as to believe the book was magic? The dollar could've found it's way there at anytime. Especially with how often he lost his things. Another test was needed. One that could not be confused with coincidence. Sam put his pen to paper once more and wrote something he thought impossible.

'Sam's pants disappeared.'

Suddenly, Sam became acutely aware of the air circulation in his bedroom. "What the hell?!" He exclaimed. A quick look down confirmed that his pants were gone. To where, Sam had no clue. But this was of little importance to him now. He knew with one hundred percent certainty that the book was magic. "I don't fucking believe it." Sam laughed aloud. Ecstatic and bewildered that such a book had fallen into his lap. 

"Wait…" Sam said. His voice a low whisper. "Could I…?" His mind raced with all the things he might do with the book. What would he do first? What could he do first? Surely the book had limitations. Sam would test them.

'Sam became undeniably handsome.'

The strangest feeling then hit Sam like a truck. A shiver went from his toes, up the length of his spine, until it finished at the tip of his nose. When normalcy had returned, Sam stood and slowly walked to his mirror. Too nervous to be excited at what he might see in his reflection. 

"I-I don't believe it…" Sam whispered. The Sam that once was had disappeared. Replaced by a man that looked like Sam's perfect-in-every-way older brother. He stripped himself of his clothing and marveled and his chiseled features, toned body, and gorgeous hair. Even his below average dick had nearly doubled in size. Lightheaded, Sam stepped back and nearly collapsed on his bed. He slapped himself. It felt real. 

In a sudden burst of energy, Sam ran to the journal. He wrote sentence after sentence and changed his life for the better in every way he could think. New clothes, fancy house, and a fast car were the first things that came to mind. He even thought to see if he could make his old girlfriend, Katy, fall in love with him again but decided against it. He figured with his new looks and his magic diary he could do far better than her. In fact, he decided he would do far better at the club that night. 

Sam got dressed, grabbed the diary, made his way out of his house like a child on Christmas morning. He grinned at the thought of Jacob or Katy being there when he arrived. He'd love to see the look on their faces when they saw how good he was without them. He might even use the diary to put them in their place. The thought alone made him feel more alive than he had for years. Tonight would be a night to remember. 

---

The club was packed. Sam had forgotten it was a Friday. He hadn't anticipated the sheer volume of people that would be inside. Thanks to his fantastic new looks he was able to get inside without too much of a wait. The only issue that remained was his severe lack of confidence. The breakup with Katy had done far more harm to his ego than the diary could repair. Sam did his best to psyche himself up. He placed his hand on his thigh. A weak attempt to calm his nerves. 

"You, uh, okay there?" A voice shouted over the cacophony. "Handsome?" Her hand traced the length of Sam's bicep.

Sam looked over. His face was flushed from the attention. "Y-Yes?" Their eyes met. It took a moment for Sam to put together that the redhead in front of him was the captain of the basketball team, Rebecca. She looked several inches shorter than she used to be. Of course, a change in height was part of Sam's drastic transformation. It would take some getting used to. "You're Rebecca, right?"

"Yeah!" She replied. Her breath smelled of alcohol and her speech was slurred. "You look so familiar. Do I know you?"

"No. I mean…I don't think so."

Rebecca leaned in close and offered her drink to him. "You look way too stiff for a cute guy in a club like this. What's your name?"

"Sam." He took the drink and finished it. 

"Sam?" She asked. "You honestly look like that loser. That's really weird that you have the same name. Are you related?" Sam nearly choked. He stumbled over his words, desperate to think of an excuse, but she didn't seem to care. "Oh my god, you are!" She grabbed his arm and pointed to one of the tables near the bar. "My friend Katy used to date that guy. You should say 'Hi.' It'd be so funny. Like what are the odds?" 

He could see her across the crowd. His heart rate quickened at the sight. Unsure of how to react, Sam said the first thing that came to mind. "How about I meet you in the bathroom instead?" Sam had no idea where the words came from. Was it stupidity or a sudden burst of confidence that moved his lips.

Rebecca laughed aloud. Loud enough to cause heads to turn. "What am I to you? A dumb whore? I'm the captain of the basketball team. I have a reputation. Who the fuck are you, Gross-Sam-Number-Two?" She turned and stormed off, a look of disgust on her face.

Embarrassed, Sam made his way to the men's room and locked himself in a stall. "Even with this damn book I can't get a girl to sleep with me. I really must be stupid…" Sam held the diary in his hands. He flipped it open to the last written page and stared at all that he had written. A few lines were left on the page. "Wait a minute…" He whispered to himself. "I really am stupid!" Sam then pulled a pen from his pocket and placed it to the page. How had he not thought of it before? In bold, sloppy writing Sam wrote his next entry.

'Rebecca went to the men's room and begged Sam for sex. She did whatever he wanted.'

He waited. Every few seconds Sam would peer out from the crack between the stall and its door. After nearly a minute the door opened and Rebecca entered, a lewd look upon her face. 

"Sam?" She asked. "You in here?"

Sam couldn't believe it. He opened the door and tried to look as casual as he could. "Couldn't turn me down, could you?"

For a moment, it looked as if she might slap him. The fierce glare was quickly replaced by a glazed-over expression. The magic of the diary kept her on track. "How could I, stud?"

Sam grinned devilishly. "Then do you have something to say?"

Rebecca paused. Her cheeks turned a bright shade of red. She squeezed her hand between her thighs and let a breathy moan escape her lips. "Please fuck me, Sam."

Sam's cock twitched at the response. He felt the front of his pants grow tight as he imagined all the things he'd do to her. But he enjoyed the sounds she made. He wanted to hear more. "That's a good start. But what about your reputation? Are you the captain of the basketball team right now? Or are you a dumb whore?"

"I'm a dumb...fucking...whore…" Rebecca pushed Sam back into the stall and slammed the door shut behind herself with her foot. "Now fuck me like one." She slipped her hand down the front of Sam's pants and gripped the base of his cock. "Please fuck me. Please."

Sam was in disbelief. The diary did far better than he could have imagined. He wanted to savor it and so he pulled Rebecca's hand out of his pants and snapped his fingers at her. "If you're a whore, you need to dress like one. Lose the dress, slut."

Rebecca gladly complied. She stripped the tight red dress free and stood still in front of Sam as he inspected her body. "Now the underwear." Again, she obeyed. As one would expect of the basketball team captain, she had a very muscular build. Sam was sure Rebecca could've easily taken his old self in a fight if she had wished. His new body could handle her easily, but he didn't need to. Thanks to the diary she was little more than a plaything. 

"You want my cock, whore?" He asked.

"Please…" Rebecca whimpered. Her thighs glistened with a combination of sweat and sexual fluids. The diary even made her legitimately horny. Sam was ecstatic.

"Get on your knees and pull it out then."

"Yes, sir." Rebecca dropped to her knees and unzipped Sam's pants. She pulled his semi-erect cock free of his underwear and held it in her hand. She looked up to him for her next command. 

Sam sat down. "Put it between your tits."

Rebecca walked forward on her knees and pressed Sam's cock between her ample D-cup breasts. She used her hands to raise and lower her breasts while she spit down her cleavage. When it was good and lubricated she kept a gentle rhythm and looked up at Sam, ever eager to please. It was a drastic change from the woman who had scorned him so readily before.

Sam gripped her by her hair. "Not so tough now, are you little miss captain?" He teased.

"No, sir." She replied.

"Good." He pointed behind her. "Bend over and put your hands against the stall door. It's time I gave you what I promised.

Rebecca's eyes lit up. "Thank you!" She stood and quickly did as commanded. She bent her back and stuck out her ass. She wiggled her butt playfully. "Use me, sir. Put this dumb whore in her place."

Sam cackled. "Gladly." He ran his cock back and forth along her pussy lips and took delight in the sounds she made. With a grunt he pushed himself in. His left hand firmly gripped Rebecca's hair while his right played with her ass. He moaned and whimpered from pleasure. It had been months since he had sex last. The pleasure was almost too much for Sam to bear. "Fuck…" Sam gasped. His cock twitched and he pulled out just in time to shoot his load on the bathroom floor. For all his new looks, his premature ejaculation hadn't gone away. Thankfully, In her current state, Rebecca did not seem to care. 

Embarrassed, Sam commanded Rebecca to get dressed and leave. He left the bathroom shortly after and lingered in the club for a bit. Rebecca and Katy were nowhere to be seen. Perhaps Katy left earlier and Rebecca took her last command too literally and went home. Sam didn't care. He was tired. He felt unhappy. The diary didn't seem to have helped his situation at all. So, that night, when Sam couldn't find it he felt little concern. 

"I must've left it at the club." Sam muttered to himself. He lay awake in his new king-sized mattress, his eyes fixed on the ceiling. "I'll just get it tomorrow. Not like things can get any worse...or any better." He rolled over and closed his eyes. Within minutes he had fallen asleep. Ten minutes later his phone's text notification sounded off. It was a text from Katy. 

---

"He looked like this?" Katy held up her phone to Rebecca. It showed a picture of Sam back before he had the diary. Back when he was still with Katy. 

Rebecca groaned. She pushed the bright screen out of her face. "I've seen your ex, Katy. This wasn't him." Sobered up somewhat from earlier, Rebecca regretted the amount of alcohol she drank.

"But his name was Sam? And he looked just like him but...as you said: better in every way." 

"Yeah," Rebecca replied, "but like, they can't be the same person. This dude was jacked. You really think he changed that much in such little time?" 

Katy didn't respond. She picked up the journal Rebecca had found and flipped through a few of the first pages. "You went back and found this? Are you sure it's his?"

Rebecca nodded. "Yup. Had it clutched to his side all night. Except for when he was fucking me. Guess he got embarrassed and left it in the stall."

"Cumming early definitely sounds like a Sam thing." Katy flipped through some more pages. "Whoever wrote this wasn't Sam. Seems like these entries were maybe written a decade ag-oh...wait a minute."

"What?"

Katy leaned over and pointed at an entry. "Sam picked up the diary and took it home."

"Weird. Is he talking about himself in third person?" 

"Look! Look! Everything after this point refers to Sam. And...oh my god…"

Rebecca groaned. "What, Katy? My head is pounding. That dumb fuck pulled my hair way too hard."

"It is Sam. My Sam. Every one of these entries is something about changing him. His body, a new car, his house. I can't believe I'm saying this but I think this diary is magic."

"Are you still drunk, Katy? Or did you like, smoke when I wasn't looking?"

"Look, Rebecca!" Katy grabbed her friend by the chin and forced her to look at the last page. "It wasn't the alcohol that made you fuck that dumbass. He wrote that you'd do it and you did."

Rebecca stared in disbelief. "Did you slip something in my water or is this making more sense all of a sudden?"

Katy grabbed her phone. "He is so fucking dead." She started to text him. Her fingers flew across the keys but stopped abruptly. "No...no I'm gonna make him wish he was dead."

"Oh?"

"You and me are going to use this diary. We're gonna give Sam the life he deserves and we're gonna have a front row seat to the carnage."

Rebecca's eyes lit up. "Now you're talking. Guess we're going to be seeing Sam again tomorrow night then, yeah?"

"Yup! And a lot more after that too. The dumbass has no idea what's in store for him."

---

[Hey. I miss you. Heard you really turned yourself around. Come hang out with me at the club tonight and tell me all about it? The one I always go to.]

Sam couldn't help but be surprised at the text. What were the odds that Katy would message him after last night. Had Rebecca said something? How else would she know about his new appearance. He was unsure, but he had to get his diary from the club anyway. Might as well entertain the thought.

[Yeah i'll be there at 11. Miss you too]

Sam regretted that last bit. He hated that it was true. Thankfully, he was much better off than he was before. Katy didn't have the advantage of looks to hold over him anymore. And if things went south he just needed to get his hands on the diary. He could fix anything with that book. It gave him the confidence he needed.

Distracted by the invitation, Sam's day went by in a blur. Before he knew it, there was hardly an hour left before he needed to meet Katy. He briefly wondered if Rebecca would be there and if things would be awkward if she was. It had only occurred to him later that he had never given the diary and direction about Rebecca's memory of the event in the bathroom. Had she realized what he did? Sam couldn't linger on the thought. He was nervous enough. 

---

'Sam would arrive five minutes early and lock his keys in the car on accident.'

"How do we know it'll work?" Rebecca asked. 

"I told him to be here at eleven. He always ran late when we dated so I figured I'd make him punctual for once." Katy unlocked her phone and looked at the time. "If he walks through that door in six minutes then we'll know we can use the diary."

"Gotcha. But why make him lock his keys in the car?"

Katy rolled her eyes. "We're gonna ruin his life, Rebecca. Not having his car keys is going to be the least of his worries." 

Rebecca's phone vibrated. It was a text from their friend, Maxine. "Maxine's on her way." Rebecca looked over to the diary. "Is it the best idea to try and get her to hook up with Sam? What if she doesn't find him attractive?"

"Already taken care of." Katy smirked. "So long as the diary works then they'll all be putty in our hands."

Rebecca raised an eyebrow. "They? Don't tell me you have beef with Maxine. Are you really doing this right now?"

Katy scoffed. "He's my ex and Maxine could stand to be taken down a peg or two. I'm not going to ruin her life or anything. Just have some fun. That's not bad is it?"

"Alright well--shit! They're both coming in right now. Have your fun but please don't do anything drastic. She's co-captain of the cheer team. People are gonna notice if something's off."

Katy brought her finger to her lips and shushed her friend. "Just relax and have fun." The two watched as Sam and Maxine approached the table together. They laughed and joked as if they knew each other. Rebecca looked surprised.

"Wait...don't tell me you know these two too?" Maxine asked. Her face was flushed.

Sam grinned. "Yeah so Katy's my ex and uh…" He stammered for a moment. His eyes met Rebecca's and it looked as if he wasn't sure how to react. He hadn't anticipated her being there. 

Katy nudged Rebecca under the table. Through a forced smile, Rebecca put Sam's mind at ease. "Glad to see you two. Don't mind me. Gonna try and not drink so much tonight since I got way too trashed last night. Hardly remember the evening."

Sam's entire body seemed to relax as he listened to Rebecca. "Yeah maybe take it easy. Never know what might happen."

Rebecca fought not to roll her eyes. "I'm gonna go dance. Y'all have fun."

"So," Katy began, "you two look pretty chummy for people that just met."

Maxine giggled. "I found poor Sam outside yelling at his car door. He locked his keys inside. Felt so bad for him I just had to see if I could help."

Maxine and Sam continued to recount the story and flirt. Katy didn't listen nor did she need to. She had orchestrated the entire thing. All so that what happened next would hurt Sam even more. "I'm gonna go join Rebecca on the dance floor." The two hardly seemed to react. Which Katy preferred. She walked on and past the dancefloor to a table in the corner of the club with a decent view of their old table. Rebecca already sat there, a glass of rum and coke already half empty next to her. 

"Those two still fawning over each other?" Rebecca asked.

"Yup! All I did was force their meeting and have Maxine be a little more horny than usual. The rest is all them." She pulled the diary back out and opened it up on the table. "Let's get started."

Rebecca peered over. "Whatcha gonna do first…"

"Now you're interested?"

"I forgot how much of a douche that guy is and Maxine is...kind of a lot. Don't be too mean to her though."

Katy uncapped her pen and brought it to the page. I'm not gonna do anything to Maxine...kinda. You'll see. But first, let's get things moving a bit faster."

'Maxine and Sam both become incredibly horny.'

Katy looked up to see that her writing had worked. Sam had sat down in one of the stools and pulled Maxine on it with him. She grinded against him and let him fondle her breasts. 

Rebecca faked a gag. "That thing really does work. She's practically pushing her massive tits in his face. Why'd you have to make 'em be so gross about it?"

"I didn't." Katy replied. "They're both just animals I guess. Let's give them some privacy next."

'Sam and Maxine head to the men's restroom to have some fun in a stall.'

"What? I thought you were gonna humiliate him? Wouldn't public be better?"

Katy shook her head. "This is just to start. Don't be so impatient Rebecca. We'll know exactly what they're doing anyway. I have all the control, remember?"

---

Maxine pushed Sam into the stall, closed the door behind her, and leaned back on it. "You know, I'm not usually this kind of girl. There's something about you that's got me…" She lifted the front of her tight black dress until her lacy pink underwear peaked out. "...so fucking horny." Maxine pushed herself off the door and pressed into Sam. She ran her hand along his chest and lowered it slowly until her fingers slipped under his shirt and danced along the flesh underneath. "You want me, don't you?"

Sam nodded. He was speechless. It had only been a day since his last fuck in a bathroom stall. This time he didn't even need the diary. At least, that's what he thought. Little did he know that the diary controlled the entire situation. 

"When did you get so shy?" Maxine teased. "Don't worry. I don't bite." She let her hand slip down into his pants. Sam could feel her fingertips gently move down his shaft and cup his genitals in the palm of her hand. "Oh…" Maxine's expression drastically changed. "I didn't think you'd be soft at a time like this...and so small." 

Sam turned a bright shade of red. "W-What? I'm not small!"

Maxine laughed aloud. She squeezed Sam's cock and balls a couple times before she pulled her hand free and lightly patted his crotch. "I've changed the diapers of little boys with bigger dicks than you."

"No that's not true! I'm supposed to be really big." He lifted his shirt and tugged his pants down to get a better view. When he saw it Sam could hardly believe his eyes. The massive cock he had given himself with the diary was now reduced to a shriveled little dick that looked barely three inches long. "H-How did this happen?! I-I promise I'm big. I'm a grower. Here I'll get it up."

Maxine snickered. "I mean...if you couldn't get it up for me grinding on your dick then maybe you can't get the little thing up."

Sam whimpered. He stood there in the stall, his pants and underwear around his knees as he furiously rubbed his dick. "Come on…"

---

Katy and Rebecca were beside themselves with glee. "Oh my god he must be panicking!"

"He may look hot but he's not gonna be able to get anywhere with that pathetic little soft dick you gave him."

Katy nodded. "Yup! Told you I knew what I was doing."

Rebecca grinned and leaned in close. "What next?"

"Hmmm...how about we emasculate him further…" Katy put her pen to the page.

'Maxine calls Sam a sissy. Sam likes it.'

"Good start!" Rebecca remarked. "How 'bout we add this…"

---

"Aww can the little sissy not get his dick up in front of a hot girl?" Maxine teased Sam. 

Sam felt horribly embarrassed at the word. But he also felt something more. He had dropped his hands at the insult and only then had his cock began to move. "I'm not a sissy." Sam replied. His voice shaky. "See? I'm horny."

"And still just under three inches...really disappointing. Not to mention you only got horny when I called you a sissy. Is that what you like? Hmm? Do you wish you were the one in the tight dress and panties?" Maxine bent forward and reached under her dress. She tugged her panties down, stepped out of them, and dangled them in front of Sam. "You wanna put these on don't you?"

Sam couldn't help but stare at the overly feminine underwear. Why was he so fixated on them all of the sudden? Did he really want to wear them? "No…" He replied. Unsure of whether or not he lied. 

Maxine cackled. "No of course not. You want me to force you to put them on." She stretched the frilly panties out in front of her. "Lose the pants and boxers. A limp-dicked little girly girl like you needs to be in panties."

Sam froze. He looked down to see his cock fully erect. It twitched at the end of each of Maxine's statements. He really did want to wear panties. What happened?

"Alright then. I see. You like not being in control, huh?" Maxine knelt down. She tugged Sam's pants and underwear down around his ankles. "Step out of your shoes and lose the underwear, sissy. Now."

Without another thought Sam did as he was told. Maxine looked up at him, a satisfied smirk on her face. "That's what I thought." She held the panties out and Sam placed a shaky foot through one of the leg holes. Then the other. His breath quickened and his heart raced as the silky panties were pulled up his legs and around his ass. Maxine slipped his erect cock under the lacy waistband and took a step back to admire her work. "And here I thought I was going to get dicked down in the bathroom like a slut." She gripped Sam's cock through the panties and squeezed. "Instead, I taught a sissy his place."

Sam gaspex at the stimulation. "P-Please…" He whimpered. "I'm gonna cum in your panties…"

"No you're not. You're gonna squirt your pathetic little load out in your panties like the sissy you are. But you're not gonna do that yet." Maxine pointed at Sam's belongings on the floor. "Put your big boy pants back on."

Sam bit his lip. "What are you gonna make me d-"

Maxine snapped her fingers. "Now. Before I drag you out of this stall and let everyone see how horny you get in frilly girl panties."

"Okay okay…" Sam reached down to grab his boxers but Maxine stepped on them. "Ah ah. You lost your men's underwear privileges."

Sam swallowed audibly. He could only wonder what she would force him to do next. Once he had his pants and shoes back on Maxine grabbed him by the hand and led him back out into the club. "What're you doing?"

"Exactly what you want, sissy."

---

"She's gonna bring him out here?" Rebecca asked, a wide grin on her face.

"Oh yeah. Time for Sam to really regret his shit attitude and what he did to you."

"Here they come!" Rebecca said. "What are you gonna make them do?"

"Just you wait…"

---

Sam followed behind Maxine, far more obedient than he thought himself capable of being. How low had his horniness caused him to sink? "W-Wait! We're not going to see Rebecca and Katy are we?" 

"Oh yeah we are." Maxine replied. "I wanna show off my new sissy bitch."

Sam tried to stammer a reply but couldn't. He was incredibly horny. The more Maxine said the harder it was for Sam to think. All he wanted was release. To do exactly as Maxine said and squirt his load in his panties like the sissy he was. 

"Rebecca! Katy! Guess what?"

The two looked up from the table. Katy appeared to hide something under her purse but Sam didn't notice. He looked down at his feet from embarrassment. 

"What?" The two asked in unison.

Maxine looked back at Sam. "Sam, why don't you tell your ex and her friend what you really are, hmm?"

Sam's vision blurred from the shock. He hadn't thought Maxine would have been so forward about it. "Uh...um I should really go." He turned to leave but a hand on his waistband stopped him dead in his tracks. A slight tug upward pulled the fabric taut against his cock and slightly wedgied the soft fabric up his backside. "Guh…"

"Are those panties?" Rebecca asked, louder than she needed to be.

"Wow. I don't even own a pair that girly." Katy commented. "You've got pretty girly taste, Sam."

Sam wanted to run but Maxine kept a firm grip. Any movement caused the panties to wedgie further. The friction on his dick was nearly too much to bear.

"Look at Sam stay perfectly still while I show off his pretty pink panties. Good sissy."

The women all laughed. "He's actually staying still because he's about to make cummies in his girly underwear. I can feel him twitch every few seconds. All I have to do is yank upward and Sam will moan like a little girl and make a sticky mess in his panties." More laughter. "Now be a good sissy and turn around so you can face the girls." Left with no other options, Sam did as commanded. "Good sissy." Maxine praised. "Now tell them all about how you wasted my time with that sad little cock of yours."

"Oh!" Rebecca chimed in. "Did Sam cum early again?" 

Maxine tugged up on the panties and Sam gasped. "Hnng...n-no. I couldn't get it up."

"Wow really? With a hot girl like Maxine in front of you?"

Another tug. Sam whimpered. The crotch of his panties were soaked with precum. "Uh huh...I only got horny when s-she...treated me like a sissy."

Katy and Rebecca were in hysterics. "Poor thing!" Katy teased. "A tiny dick like yours belongs in panties though, doesn't it?"

Sam nearly moaned aloud. Panties wedgied up his ass were more than enough to get him off. The teasing only made things worse. Sam stumbled forward and placed his hands on the table. A shiver went up his body and he felt nearly ready to burst.

"Ah ah ah!" Maxine chided. "Sissies need permission to make a mess in their pretty panties."

"Puh-please!" Sam begged.

"Only if you admit to how you're a pathetic, limp-dicked sissy that loves her panties."

Sam had no dignity left at that point. He only wanted release. "I'm a limp-dicked little sissy that loves his panties! I wanna squirt my pathetic load...please…" A few women at the next table looked over. Looks of disgust and amusement plain on their faces. One even had her phone out and pointed at Sam. 

"Tug your pants down."

Sam's eyes opened wide. "What?"

"Your panties and your tiny little dick are too cute to hide. Tug your pants down so everyone can see them or I'm going to do it for you."

Sam looked around to see all the faces that looked at him expectantly. As if he lacked all control, Sam obeyed and exposed his leaky panties to the room. "Please…" He again whimpered. 

"Good sissy...now mewl like a good girl for me." Maxine yanked upward and forced Sam to his tiptoes. In less than a few seconds Sam was reduced to grunts and moans. His cock twitched once, then twice. A few small squirts of cum coated the crotch of his panties as he orgasmed. Unabashedly he fell to his knees and gasped as he convulsed. It was the most powerful orgasm he had ever felt. And it was from being wedgied in panties at a club. 

As the endorphins left his body and his breath returned to him so did his shame. He could hear the laughter and ridicule clearly. His face turned a deep shade of crimson and he desperately worked to pull his pants up so that he could leave as quickly as possible. He hardly even noticed the ridiculous whale tail that he now sported as he ran from the club. What had he become in just a few hours?

---

Maxine, Katy, and Rebecca stayed at the club for a few more hours following Sam's humiliation. They mostly discussed the events that had unfolded with regards to Sam but as the conversation switched focus to Maxine things got a bit heated. 

"So you stole his 'magic diary' and used it to make us do all that?" Maxine asked.

Katy tapped the book absentmindedly. "Uh huh. Well it was more than making you do things. It made you feel and think things too."

"You expect me to believe that? I was completely in control back there. And that Sam guy is clearly into some weird shit."

Katy looked at Rebecca then back to Maxine. "I could show you."

Maxine scoffed. "Alright. Wow me."

Rebecca put her hand on Katy's arm. "Let's not do anything too drastic, Katy."

"Oh please, Rebecca. I'm just having a little fun." Katy then put pen to paper and wrote her next entry: 

‘Maxine stood up from the table, exclaimed to the world “I love cocks!”’

Rebecca, despite her concern, couldn’t help but burst into laughter as she watched Katy write. “Oh my gosh, Katy. You are just the worst.”

Maxine leaned over to get a clear view of what Katy had written. “What? What is i--” She stopped mid-sentence, her eyes glazed over, and stood up from the table. In the loudest yell she could manage she exclaimed to the world, “I love cocks!” A second later her freewill returned. Her face turned a bright shade of red once she realized everyone stared at her. “Oh god...don’t tell me…”

“What,” said Katy, “that you love cocks?”

Maxine buried her face in her arms. “Fine! I believe you! Just never do that again.”

Katy placed a hand on Maxine’s shoulder. “Of course, sweetheart.”

“So we’re done with Sam for tonight?” asked Rebecca.

Katy tilted her head and thought for a moment. "Yes...and no. Sam's got some big changes in store for tomorrow, let's give him a sneak preview tonight!"

---

Sam laid in bed with his face buried in the pillow. He couldn't believe what had happened. To make matters worse, he couldn't shake the feelings he had felt earlier. Part of him wanted to go grab the sticky panties off the floor and put them on again. Since when had he had such strong feelings? Between the sissy desires and his tiny dick, Sam barely felt like a man anymore.

"Could this day get any worse?" He said, his voice heavily muffled by the pillow. Almost as soon as he had uttered the words, a strange sensation caused him to sit up suddenly. He looked down at his naked body. Something had changed, but he wasn't quite sure what. He stood and walked to his mirror to examine himself. "I look the same...right?" Except he didn't. His body hair was now gone and his muscle definition reduced. His skin felt and looked softer as did some of his facial features. "What the fuck is happening?! Is it this house? Was the diary cursed?"

Sam ran to his closet and tossed a shirt on. Next, he went to the dresser and pulled a pair of boxers and gym shorts free. He wasn't sure what did but he knew he needed to stop whatever happened to him. "M-Maybe there's something or someone at the yard sale house. I gotta go there and…" Sam had passed by his mirror only to see that his clothes had changed as well. The once baggy black t-shirt had begun a tight pink crop-top. The ill-fitting gym shorts had turned into white and pink tight dolphin shorts that hugged his new bubble butt all too perfectly. His hair had changed too and had become shaggy and soft. He almost looked like a girl going out for a jog.

Sam paused for a moment and stared blankly at the mirror. "What was I just doing? Was I going for a jog? I-I was. That's right. A late night jog." Slightly bewildered, Sam sat down on his bed and slipped a pair of athletic shoes on. They were way too big at first but quickly shrunk down into a pair of comfortable pink sneakers. "That's weird...right? Were my feet always this small?" The thought left as quickly as it came and before Sam knew it he had grabbed his phone (now in a sparkly pink case) and put a scrunchie in his chin length hair. He nearly skipped outside and stretched on the sidewalk. His mind was blank. He was unsure of where he planned to go but his body seemed to know. So he set off, unaware of the minor changes that affected his body with each step. Just how different would Sam be by the time he reached his destination?

Chapter 2

Too drunk to drive and too close to campus to bother with a ride, the girls decided to walk home together. A long walk in the dark might have scared the women before, but in their drunken haze with a magic book in their hands, they hardly felt any concern. They were carefree, for the most part. Only Maxine looked a little worried. 

"Don't you think this is maybe, like...a little too much?" Maxine asked. Rebecca and Katy walked on either side of her. They both turned at stared at her with more intensity than she was ready for. "I know you say he deserves it. It's just a lot for anyone I guess."

Rebecca sighed and motioned for them to stop. "That's very kind of you to say, Maxine, but this guy's an ass. He doesn't need magic powers to do shitty stuff to his girlfriend or other women. This isn't the first time Katy and him have broken up."

Katy frowned. "Ugh. Don't remind me."

"Well, remind me then." Maxine replied.

"Alright," Katy agreed, "but don't say I didn't warn you. You're probably gonna want a go at the book after this." Katy paused. She seemed to think hard on what she would say. 

"Why I ever got with him I'll never know. He seemed fine enough from a distance. Could make me laugh. Looked pretty alright. We started dating and he only seemed to get more enjoyable. But after those few months he started to slack a bit. I started to see what he was really like." She sighed audibly. "As you know, he cheated on me multiple times. Only found out when some of the girls he had been with found out I dated him. A few were more 'just to let you know' but some told me he had promised to date them or that he had been overly rough during sex. Found out he was into some hardcore stuff. Tried to get me into. I don't kink shame but it wasn't for me. Don't think he liked that one bit. Wanted to call it quits several times but I kept on. And it just got worse and worse. One day I walked in on him with another girl. He was choking her. I had assumed with consent but when he saw me he just dropped her and she looked like she might have passed out if I hadn't shown up."

"So...yeah," said Rebecca. "The guy's an ass. And an awful one at that."

"I'm so sorry, Katy. I had no idea it was that bad."

"Now you know why I'm not inclined to give a shit about his feelings. Of course, the first thing he'd do with a thing like the diary would be to abuse his new looks and wealth."

"Well, consider me all for whatever you have planned. He has it coming."

---

The three had started to walk again during the course of the story. They had nearly reached campus by the time they had nearly finished their discussion. They were thankful for the lights that lined the campus adjacent roads. For the first time in twenty minutes they could finally see properly.

"Can't believe I ever wanted to hook up with him," said Maxine.

"Yeah," Rebecca chimed in, "the guy sucks. Not to mention the shitty stuff he did to both you and me in the past couple days."

"Yeah..." Maxine looked across the street. Her eyes widened and she pointed in the direction of a petite figure jogging down the street. "I-Is that Sam? He looks even girlier than before."

Katy grinned from ear to ear. "Sure is. Looks like the little sissy is working on his girly little form."

"Looks like he's looking for something…" Rebecca's voice trailed off. She honestly couldn't believe what a sight Sam made in his cute jogging outfit. 

Katy raised an eyebrow. "Maybe he's looking for his precious book?" She raised the book and wiggled it. "Tell you what Maxine. I'll do it. I'll give him a fourth chance he definitely doesn't deserve." She knelt down and opened the diary on her knees. With a shaky hand she pressed her pen to a page and scribbled some things her friends could not quite see. "We'll need some insurance of course." When she finished she abruptly stood, closed the book, and stuffed it into Maxine's hands. "You wanna help him so bad, why don't you go give this to him."

Maxine was shocked. "Give him the book? Really? He's going to turn on me immediately!"

"Not if you pretend like you feel bad for him. Don't worry, I've made sure he can't turn on us. Just don't let him know that." Katy turned Maxine around and pushed her in Sam's direction. "Good luck!"

---

Sam took a moment to break and regain his breath. He bad spent the past hour jogging around his neighborhood. For some reason he just couldn't find that house where he got the book originally. Everything looked familiar but the house couldn't be found near anything. It didn't help that he kept forgetting what he was doing. Every few minutes he'd stop to catch his breath only to start jogging in a random direction. His brain grew warm and fuzzy and all he could think about was how toned his butt would look if he could just run a little longer. Just as he was about to give up hope, he turned to find Maxine just feet away with the magic diary in her hands. "Hey…" She said with a nervous smile. She offered the diary to him. "I'm so sorry about what happened earlier. I wasn't really feeling like myself and I was horny and drunk...you know how that is."

Sam looked down at the diary. He almost didn't know why he wanted it anymore but he took it nonetheless. "That's okay." He replied. His voice was light and sweet. His hair had grown long since Maxine had last seen him. It even looked as if he had formed little breasts in the time they had been apart. She couldn't help but wonder how much more he would've changed had they not intervened. "Thanks for bringing it back." He opened the book and thumbed through the first few pages. Realization dawned on his face as the fog that clouded his mind seemed to dissipate. "Really. Thank you." He looked around for a second before he closed the book then made his way back down the road.

Maxine stood there bewildered. She hadn't expected such a response. A minute later, Katy and Rebecca appeared. "So? Was he an asshole?"

Maxine shook her head 'no.' "He just seemed really confused then really not confused. Maybe he's learned his lesson?"

Katy and Rebecca looked at each other. "Maybe." Rebecca replied. 

"Could be a trick. We'll have to keep an eye on him to make sure. Though some part of me thinks he'll come to us."

---

A few days after Sam had regained the book, the girls were surprised to find that they hadn't run into him at all. It was a good sign, or so they thought. Katy, eager to keep tabs on her ex on the off-chance that he was back to his old ways, decided to stake out the drive to Sam's new multi-million dollar home. Some part of her regretted having given Sam the book back. It could clearly do incredible things; useful things that would've been far better for her to do than to give a guy like Sam a second chance. That's why she kept such a close eye. She just knew he'd slip up eventually. It was in his nature and with such an incredible book on the line, she would need to make sure things didn't get out of hand. Dependent on one's view of when things get out of hand, of course. He had already made himself a mansion and has people working in the yards. Though Katy knew that she would probably be just as decadent if she had the magic book instead of Sam, she couldn't help but be annoyed. She knew how he could be. Katy worried for any women that worked for him. 

On the second night that Katy kept watch she managed to see something out of the ordinary. A black SUV drove up the drive and parked in front of the house. A few girls exited the car without a word and made straight for the front doors. Sam exited shortly after. He was also silent but he was clearly busy with the book. He wrote furiously. One sentence after the next. A smirk on his face.

"So this is what you've been up to?" Katy said to herself. "Decided to pick some playthings up at the bar? Disgusting...they're completely expressionless. How much are you changing them?" Katy set down her binoculars and texted Rebecca and Maxine right away. She hoped they would be able to stop him in time but it was unlikely given the security he had setup. She had an idea, but Maxine and Rebecca might not like it. 

The two of them arrived about thirty minutes later. Rebecca had dressed as if she had planned to pull off some kind of heist. She wore a tight all-black getup with minimal makeup. Maxine, on the other hand, was dressed as if she planned to go clubbing. She sported a tight red top and a short black skirt with a pair of tall heels.

"Well. One of you is dressed appropriately. But surprisingly it's not Rebecca."

Rebecca looked disappointed. "Really? Aren't we sneaking in? Get the jump on him before he does god knows what to those girls."

"Honestly," said Maxine, "I was like this close to heading to the club so this is what you get."

"No. It's perfect." Rebecca pointed over to the front gate. "We aren't spies or burglars. We aren't getting through all that. So...we're going to walk up and ask him to let us in."

Rebecca and Maxine looked at each other. Their mouths were wide open in disbelief. "You're fucking with me." Rebecca replied. 

Maxine shook her head. "And you think he won't turn us into brainless cumdumps as soon as he knows we're here?" 

"Nope!" Katy smiled. "I told you I had some extra insurance in place in an event like this. We're going to be totally fine. We just have to play our parts." 

"Which are…?" Rebecca looked incredulous. 

"Come on." Katy urged. She grabbed them both by the hands and crossed the street. "Just follow my lead." There was just the slightest bit of resistance from the other girls. Rebecca especially. But they followed along nonetheless. Once they arrived at the gate Katy made a gesture to her friends to be quiet and pressed the call button.

"Hello?" Katy called. Her voice was light and innocent. "Is Sam there?" 

As she expected, a strange voice answered in place of Sam's. It was gruff and not at all what her ex-boyfriend sounded like.

"We're not expecting any other guests tonight. You ladies are going to need to leave."

"We're friends of Sam's. Just tell him we're here."

The line went quiet for a moment. Unsure if he would come back, Rebecca began to devise a backup plan. "Think he's got security cameras over there by the thick brush. I'm sure we could get in unnoticed."

"If only we had the book." Maxine murmured. 

"If we had the book we wouldn't be here." Said Rebecca, annoyed. 

Before the two could continue continue to squabble a familiar voice crackled from the call box. "Girls! I'm surprised. Figured you'd be avoiding me." It was Sam. His voice sounded smoother than before. Even through the static of the speaker it sounded far more appealing than it had before.

Katy looked over at Maxine, suddenly unsure of her own plan. In a hushed voice she spoke to her friend, "You speak to him."

Maxine glared at Katy but spoke nonetheless. "Hey Sam! We were just in the neighborhood and figured we'd come by and apologize for the other night. We were drunk and getting crazy and--"

"You had the diary and you wanted to humiliate me. Yeah?"

Maxine bit her lip. She looked at Rebecca, unsure of what to say. "We were wondering if there was anyway we could make it up to you." Rebecca followed up.

Once more there was silence from the call box. The girls waited there for a few minutes before the gates began to open. "How about you come in and we can talk more."

Katy nearly jumped for joy. He had taken the bait. "Yeah. Sure thing!" She said. "We'll be right up. 

---

The walk up was a short one. Sam waited for them at the entrance. None of the girls were surprised to see him in the doorway, a sly grin on his face. "Never thought I'd see this. All three of you having some manners for once."

Katy stifled a grimace. She knew him well enough to know he purposely sought to rile them up. Part of her wondered if he knew what they had planned but she tried to remain confident. "You know me, Sam." She replied. "Always full of surprises." 

"Now more than ever." He stepped to the side as they approached and waved them in. "Follow me." Sam stepped forward and led them down a spacious hallway to the northside of the house. The girls were surprised to find they had been led right to his bedroom. He sat down on the edge of his bed and motioned to the floor in front of him. "Alright well get to it."

Maxine scoffed. "I'm sorry?"

"You wanted to apologize so...you can each get on your knees and give me what I want or I can write a few sentences and make you do it. Got a couple of girls in the next room that decided to take the hard way if you'd like to see what I can do." He unbuttoned his pants as he spoke. All the while his eyes never left Katy's. 

"Not happening, asshole." Katy replied. Her disdain extremely apparent. She then nodded to her friends. Maxine and Rebecca looked at one another. They knew there would be no going back. Despite their misgivings, they jumped into action. Maxine slammed the bedroom door shut while Rebecca made a dash for the diary.

Sam's eyes widened as he realized what had happened. He jumped across his bed and snatched the diary from his nightstand before any of the girls could get anywhere near it. "I thought that maybe this was too good to be true. Are you girls back to get revenge? To teach me a lesson?"

"I fucking knew you couldn't change. Once an asshole, always an asshole." Katy replied.

Sam scoffed. "Guess you were right on that one. But I have bad news for you girls. I have the book, and you don't. You know what that means?" Sam paused, as if he waited for an answer he didn't want. "It means, I've got three playthings in front of me. Three puppets I can control however I want."

Rebecca and Maxine looked to Katy. They were both terrified, unsure of what Katy had planned if anything. 

"Tell you what. Rebecca, Maxine. You two can get on your hands and knees and suck my cock. Be good, obedient little cumdumps and I won't use the book on you. Katy, however...you need to be taught your place." Sam opened the book and started to write. "Let's see...what's something fun and fitting for a bitch like you. Oh! I know. Let's make you cum at the slightest touch." He laughed to himself. "You could try and run and all I'd have to do is smack your ass and you'd fall over, cumming like the dumb slut you are." Sam closed the book and stood. At his new height he towered over all three of them, a smug look plain on his face. "Not running, huh? Do you wanna get on your knees with your friends and be a good girl for once?" Sam grabbed Katy, abruptly turned her around and smacked her ass full force. Katy yelped from the pain but did not react any further. Sam was puzzled. "Why aren't you cumming?"

Katy smiled to herself. She turned ever so slightly and gripped Sam's cock through his pants. "I'm not cumming because you're the one learning their place."

Sam gasped. His eyes bulged outward and he moaned through gritted teeth. Katy could feel his cock grow hard and ejaculate all within a moment. He fell to his knees the pleasure was so great. "H-How?"

"This was a test, Sam." Katy explained. "Did you really think we'd just give you that much power back?" Sam tried to stand but Katy stopped him completely with a firm grip on his underwear's waistband. 

"S-Stop it."

Rebecca and Maxine both laughed aloud. "Awww does someone not like being on their knees?" Rebecca teased.

"Ah ah! You gotta be obedient if you want us to not use the book on you remember?" Maxine joined in.

Katy gently tugged at the waistband. She took delight in the small, ragged gasps that escaped Sam's lips. "So does cumming like this make you a dumb slut?"

Sam, still confident as ever, scoffed. He made to stand only to have Katy give him massive wedgie. He whimpered helplessly as his cock unloaded in his underwear again. "Puh-please...it feels too good…"

This got a good laugh from all the girls. "Awww does little Sam like cumming in his undies?"

"Does he need girls to give him wedgies just so he can whine and cum all over himself?"

Katy grinned, a brilliant idea had suddenly come over her. "Katy, Rebecca, pull Sam's pants down." Sam wanted to fight it but Katy kept a firm grip on his underwear. Like a taut leash it kept him firmly in place lest he risk another powerful orgasm. 

With his pants pulled down, his cumsoaked and wedgied boxer shorts were on full display. Sam's face turned a shade of crimson as the girls continued to mock him. "J-Just leave me alone! Take the book an l--"

Katy didn't let him finish. With a heave she yanked his underwear harder and harder until she was able to pull it up and over his head. With each yank he came in his underwear. By the time he was left in an atomic wedgie, cum dribbled out his boxers and down his thighs onto the floor. Stuck as he was Sam had no hope of running. Instead, he could only cim again and again from the stimulation the wedgie gave his crotch and backside. The girls looked down at him with glee as he whimpered and moaned.

"Awww look, girls. Sam couldn't make us his cumdumps so he made himself into one." Katy teased. She went over to the bed and picked up the diary. She placed a foot firmly on Sam's back and read what she had written earlier. "'Whatever Sam writes in this journal about Maxine, Katy, or Rebecca will happen to him instead.' I wrote that on the back page. Figured you'd never think to look there."

"I don't even think he can hear you, Katy. As embarrassed as he is, he's cumming so much. I don't think he can even think straight anymore."

"Yeah," Maxine chimed in, "and he's making such a mess."

Katy looked down at Sam. She never felt so much satisfaction in her life than in that moment. "You're right. Guess we'll need to put him in something to help with that, won't we?" Katy turned the pages in the diary, found a blank one, and started to write. "First off, for some added insurance, let's get rid of Sam's ability to read and write." She scribbled a few words. "And now that he's illiterate and making such messes, it makes all the more sense that we put Sam back in diapers."

"Oh my god. That's so perfect." Rebecca said with a laugh. "What girl would ever want to be with a guy cumming in his diapers all the time."

"Yes! We should make it really thick and embarrassing. Too big for him to wear big boy pants. He'd have to waddle or crawl!"

The mere mention of something that embarrassing managed to shock Sam out of his stupor. He tried to reach back and remove the wedgie only to have Katy do it for him. "Good boy. Are you that excited to be put back in diapers that you wanna help?"

"N-No! You're not going to do that!" Sam tried to snatch the diary only to have Rebecca spank him. He gasped and came on himself again. He fell onto his back and remained there as the orgasm finished. He could barely fight as his cum soaked shorts were removed. Any movement from him and the girls would force another orgasm. Positioned as he was, each load shot out onto his stomach and chest.

Katy knelt down beside him and started her handiwork. "Let's see. No more big boy undies for you. Let's go ahead and turn all your underwear into diapers."

Sam was shocked to watch his cum-covered shorts slowly puff up and turn into a large, heavily cum-soaked, pink diaper. "N-No…"

"Oh yes, Sam." Katy teased. Then to Rebecca she said, "His bottom dresser drawer should be full of diapers now. Grab me one would you?" She looked back down at Sam. She kept a firm grip on one of his nipples. She lightly teased it whenever he'd get too aggressive. "Aren't you so excited that your ex-girlfriend and her friends are putting you in diapers?" Sam fumed. He was furious but there was nothing he could do but cum on himself as Rebecca unfolded the diaper and helped Katy slide it under his butt. It crinkled loudly as he squirmed on it. 

"Go ahead and tape Sam into his diapers you two. I have some changes to Sam I need to make." 

'Sam could not remove his own diapers.'

Katy watched with glee as Sam struggled to move. His expressions were perfect she decided. How helpless and upset he looked once he had been taped into the thick, humiliating garment. 

'Sam's cock shrunk each time he came in his diapers.'

'Sam's bladder and bowel control weakened each time he used his diapers.'

Rebecca and Katy stood to admire their handiwork. Sam laid there. His legs spread, his eyes red, and his stomach covered in cum. He had never felt so utterly humiliated. He tried to stand but quickly fell back when his cock rubbed against the thick padding. The stimulation was too much. With a whimper he ejaculated into his diapers. Katy couldn't help but laugh aloud. "Aww did the little baby cum in his pampers? Is it too hard to walk? Maybe you should crawl, little boy."

Sam grimaced. "C-Change me back! I-I don't deserve this! I'm not a baby."

Katy leaned knelt down beside him and gripped his chin firmly with her hand. "Oh? And what was that about teaching me my place? Or all these unfinished sentences in here?" Sam's face turned pale. "Let's see...this one says 'Rebecca, Katy, and Maxine become my personal sex…' Was 'slaves' the next word that you were going to write as soon as you could?"

Sam looked away. His lip trembled. "N-No…"

"I'd say being an illiterate, small-dicked, little diaper humper is a far better fate than being someone's obedient slave. Wouldn't you girls?"

Maxine and Rebecca both nodded. "It's not that bad." Rebecca said. "I mean, girls love babies right? Maybe you could find some girl that likes changing your cumsoaked diapers."

"He'd probably have to pay for it." Maxine joked.

Sam's face burned a bright shade of red. He sat up and reached for the diaper's tapes. The girls all watched him struggle, amused. "Why won't these come off?!"

"Because you'll make a mess when you take them off." Katy explained. "Babies don't change themselves. If you want out of your diapers, you're going to have to behave yourself and ask nicely."

"Ask nicely?!" Sam yelled. "There's no nice about this!"

Maxine groaned. "Can we get the baby a pacifier or something?"

"Yeah seriously. Is it naptime yet?" Rebecca added. "Should we make him a crib so he can't leave?"

For the first time, Sam looked as if he might actually cry. It was hard not for the girls to gush over how cute he looked then, diapered and whimpering as he was. "Poor thing...he's completely helpless now, isn't he?" Rebecca pointed out.

"Yeah...I mean. His dick is locked away in his cum-soaked diapies. He's never going to be seen as a man again."

Katy smirked. "Is little Sam sad that he can't be a shitty person anymore? That he has to crinkle around in his diapers and do as he's told." She looked at him square in the eyes. "Go on. Tell me how sad you are and I might go easy on you."

Between sniffles Sam managed to say what Katy wanted. "I'm s-sad that I can't be a shitty person anymore. Puh-please go easy on me. I-I'll do what you want." 

Katy patted his head. "Good boy. You will do what we want but it's good to hear you say it. Now that we're on the same page, let's discuss what's going to happen next." Katy reached under Sam's arms and helped lift him so that he stood. "You've been a very naughty boy. You're going to walk over to the corner and stick your nose in it like a misbehaving toddler while we think about what to do with you."

The three laughed as he did just as he was told. Sam, as tall and muscular as he was, was quite the sight. To think that such a physically strong man could be put in diapers and made to stand in a corner. Sam was painfully aware of this too. He had so many chances for this not to happen. He could've moved away or made sure not to interact with Katy or any of her friends. There, with his nose stuck in the corner he could only feel stupid after all he did.

The three did not bother to keep their voices down when they discussed Sam. They were completely in control and took great pleasure in seeing him squirm. 

"The tough guy look has got to go." Rebecca began. "He needs to be easily controlled. Like, even if he got the book back it should be easy to just pull him over my lap and make him regret it."

"We could sissify him again." Maxine added. "I mean, his dick is already shrinking anyway. It'd be all too fitting." 

"Just what I was thinking," said Katy. She held the book up and wrote a few more lines.

'Each time Sam asks for a diaper change he becomes more girly and helpless.'

'Sam quickly develops a thumb sucking habit.'

'Sam becomes more obedient each time he is spanked.'

"There. That should make things more interesting." 

While Katy wrote, Maxine walked around the room. Rebecca had left to go check on the girls Sam had mentioned. Sam was left to sniffle in the corner. He was too scared to move. Even the slightest bit of movement in the padding was enough to cause an audible crinkle. The diaper was thick and snug. His semi-erect cock pressed against the soft interior of his diaper and threatened to elicit a moan from his lips. The thought of cumming in his diapers again was too much to bear. 

Maxine couldn't help but laugh at Sam's misfortune. She could see how much he struggled to hold it in. "Awww...is the little baby upset 'cause he's in timeout?"

Sam grumbled under his breath and turned away. Maxine just giggled and approached him from behind. She quickly reached around his waist and grabbed his diapered crotch. With zeal, she pressed herself against his back and gave his dick a good squeeze through the padding. Almost instantly Sam ejaculated in his diapers. He gasped and whimpered as he did so.

"Did you cum in your diapies again, little baby?" Maxine playfully spanked Sam on the butt. Unknown to Sam, the simple act of a slap to his rear had just made him more obedient and submissive. The change was small at first, but would get more drastic with each slap. 

"N-No…" Was Sam's weak reply.

Maxine laughed. "Is that so?" She grabbed the front of Sam's diapers by the waistband and pulled it back to expose his cock within. It was far smaller than Sam remembered and still sticky with cum. "Well you're still bigger than last time I saw it, but that won't last long." 

"What's that supposed to mean?" 

Maxine grabbed Sam by the back of the head and gently guide his nose back to the wall. "It means, baby, that everytime you squirt your pathetic loads into your little girl diapers your cock gets smaller. It'll keep happening until you've got a cute little baby-dick between your legs. Perfect for the little sissy baby you're going to become." Maxine released Sam and turned back to Katy. "His house is way too big and nice. Oh! You know what? How 'bout it's our house now. We can turn Sam's room into a big pink nursery while we have the rest of the house to do whatever we want with."

"Wonderful idea! We'll need to keep an eye on him of course. And while we're at it, we should probably get a high chair and a training potty for our little sissy. Not that he'll ever be allowed to pee in it." Katy then walked over to Sam and spanked his diapered butt. "Hear that, Sam? Your days as a big boy are over. No more potties and no more girls. From now on you're wearing those diapers twenty-four seven. You'll piss in them. Cum in them. Even poop yourself. Like the sissy baby you are."

Sam didn't answer. He kept his nose firmly against the wall. He couldn't explain why but it seemed to him that he had gotten more used to the idea of doing what he was told. He would, of course, never let the girls break him in. He knew he would always try to escape as soon as he could. But it seemed that some part of him thought it best to behave. 

"Hey, Katy." Rebecca stood in the doorway. A couple of women next to her. Semi-familiar faces. They went to the same college. Katy had seen them around campus from time to time. They were naked save for the collars around their necks. The collars each had a tag and they read 'Cumdump' and 'Cocksleeve' respectively. Their eyes were somewhat glazed over and dried semen was seen around their lips and chin. "Looks like these were Sam's 'playthings'. Sick fuck." 

"They wanted me to do it." Sam grumbled from the corner."

"Shut it, sissy, or I'll bend you over my knee and give you something to whine about," replied Rebecca.

"I'll see if I can undo whatever Sam wrote about them earlier." Katy thumbed through the pages. "Ah! Here we go. Looks like their names are Karley and Melissa. I think they're on some sports teams at college. I'll get them back to normal." Maxine wrote a couple more sentences and the two girls regained their senses almost immediately. 

"Where am I?" asked Karley.

"We went with that guy, Sam right? We're at his house...but...who are they." 

Katy spoke up first. "Sam's ex and her friends. Sam did some awful shit and we're going to punish him. You two want in?"

"When did I get naked? And...collared? 'Cumdump'? What the fuck." Melissa grew more furious by the second.

"Oh my god. Is that him in the corner? Wearing diapers?"

"He's in timeout for misbehaving. It's hard to explain but let's just say that Sam won't be trouble anymore. So...if you wanna help us get revenge, you're welcome to join."

The two girls looked at one another. They agreed to it almost immediately. Katy was ecstatic. She and Maxine approached Sam to get him ready for his next humiliating experience while Rebecca helped the two newcomers find their clothes.

"Time for more fun, potty pants." Katy teased. "It's going to be very humiliating, so I'll give you a chance to make it less bad."

"O-Okay…" Sam replied. His voice was hopeful.

"I want you to suck on your thumb and wet your diapers in front of all the women here. You do that and I'll go easy on you."

"There's no fucking w--"

THWAP

Maxine spanked Sam square on the butt. "Language, sissy."

Again Sam felt the odd desire to comply. Without thinking he mumbled out a pathetic "I'm s-sorry."

Karley, Rebecca, and Melissa reentered the room. Karley and Melissa were now fully dressed and cleaned up. All three of the women had devilish grins on their faces. "Is the baby going to put on a show for us?" Rebecca asked.

"Depends," Katy replied, "Does little Sam wanna do what I asked?"

Sam looked down at his feet and said nothing. 

"Suit yourself. This will be much more fun anyway." Katy opened the book and began to write again.

'Sam cannot spit out a pacifier if someone else puts it in his mouth. He will suck on it like a baby until someone removes it for him.'

'Sam can't help but wet or mess his diapers when commanded to.'

With another few words Katy produced an oversized pink pacifier with the word 'Princess' written on the front in sparkle letters. "Here you go Princess." She stuffed it in Sam's mouth and watched with glee as he sucked on it in a nice even rhythm while his face grew red with embarrassment. He tried to tug at the pacifier but it was no use. "Awww...such a good sissy baby sucking on your paci like that." She lightly patted Sam's butt and pushed him out in front of everyone. "Show everyone what a cute sissy baby you are Sam."

Sam stood there with tears in his eyes as the group full of women he had wrong mocked him.

"Look he's crying!"

"Does baby need a diaper change?"

"Does someone need a nap?"

Katy let this go on for sometime before she raised her hand. "Hold on girls. I think Sam has something to show us. Don't you?"

Unable to speak while he sucked on the pacifier, Sam could only stare. 

"Wet your diapers like a good little baby."

Sam thought Katy's demand ridiculous. She'd have to force him to do something so humiliating. It took him a few seconds to realize what had happened. The laughter in the room increased as the warmth in his diaper did. He watched helplessly as the crotch bulged outward and sagged between his thighs. "Mmph!"

At the same time, Katy's other diary entry began to take effect. As he wet his diaper his features grew softer and his muscle mass decreased. By the time his diaper was soaked he looked like a slightly more effeminate version of his old, original self. 

"Good sissy! Now, since you decided to be a bad little sissy and not do what I asked I'm going to go hard on you." Sam waved his arms and whimpered. He clearly couldn't take much more. "Time to make a mess. Poop yourself like the helpless little baby you are."

Immediately, Sam squat where he stood and grunted. Helpless to the command, he continued to grunt and strain until he managed to poop himself. With his hands pressed against the wall to balance himself, the girls got a clear view of Sam's shame as the back of the diaper bulged outward. The diaper crinkled loudly from the sudden additional weight and Sam gasped as he finished. 

Same as before his features softened further and he lost even more muscle mass. His body hair all but disappeared and his voice started to go up in pitch. His whimpers were far more girly than just a few minutes ago. 

With his diaper heavy and sagging, Sam began to openly cry. Any hope he had of escaping had disappeared. If they could make him do that on command then they'd never let him leave. Just like Karley and Melissa, he had been turned into a plaything. 

"Wow, he really is just a big baby now. Crying in your messy pampers, sissy? Do you wanna ask nicely for a diapie change?" Karley teased. Momentarily defeated, Sam nodded and lowered himself to the floor at their direction. 

"Wait a minute. Baby's first diaper change should be on a changing table. It's the perfect time to get started on Sam's nursery." Katy approached his computer desk and smirked. "Won't be needing this anymore." With a quick scribble the desk faded away and was replaced by a large wooden changing table stuffed to the brim with diapers and decorated with unicorns. 

With everyone turned to the changing table spectacle, Sam saw his chance. He stood quickly and quietly and made his way to the door. Within a second, a pair of hands gripped his diapers by the waistband and yanked backward. Sam yelped as the mess and soaked padding were suddenly pressed into his backside and crotch. "We need to get you a kid leash, don't we?" Rebecca held him firmly where she stood. She clearly noticed how messy Sam's diapers had begun. To hammer home her point she yanked the diaper upward into a wedgie. 

"Mmph!" Sam lost his balance and the wedgie became far more severe than intended. Almost his entire body weight was leveraged against Rebecca's strength. She held firm and the diaper was wedgied even harder. He started to cry again as the mush in the seat of his diaper was spread around further from the wedgie. All the motion was too much for his small dick. Sam whimpered as his cock spurted another warm load into his diapers.

"Oh my god. He came again," said Rebecca. "We're going to have to put him in thicker diapers. He's making such a mess."

"Of course he is. And deep down Sam loves it, don't you?" Katy yanked the pacifier from Sam's mouth. "Is that why you keep making stickies in your diapers?" Sam was too choked up to respond. He just shook his head and softly cried. "Do you wanna keep cumming in your diapies or do you wanna beg Mommy for a diaper change like the pathetic little sissy you are?"

"Please change my diapers mommy…" Sam begged. He sniffled between each word. Snot ran down his face and his diapers threatened to leak at any moment. 

"You'll get your diaper changed. But Karley and Melissa are going to do it and you're going to apologize for everything you did to them. Do you understand?"

"Y-Yes mommy…"

Katy smiled. "This is a much better look for you Sam. So much better than that asshole you used to be." With the help of Rebecca, Katy managed to lift Sam up onto the changing table and strap him down. "Now you be a good little sissy and do what I said for your 'babysitters'. Sam nodded. He wouldn't dare risk anymore punishments. He'd do anything they want so long as he could wear a clean diaper again.

"Well, well, well. Now isn't this a sight," said Karley.

"Did you ever think while you were throat-fucking me and Karley that you would wind up sissified and begging us to change your diapers?" Melissa reached down and untaped the diaper. His dick, far smaller than last time Sam had seen it was then exposed. Karley and Melissa howled with laughter. "Look how small it is!"

"Even if you could get your little dick out of your diapers a girl wouldn't even feel it."

"Any girl that gave him a chance would just put him back in diapers and bring him back home to mommy."

"It's barely any bigger than my pinky."

Sam endured their continued mockery as they wiped him clean. He turned his head to see that Katy went to each of his possessions and infantilized or sissified them in some way. His bed was now a crib, his wardrobe was full of frilly dresses and diaper covers, and all of his sports memorabilia had been replaced with a toy chest full of stuffed animals and dolls. 

Katy caught his stare and smiled. "Like your new room, sissy? I'm making sure to baby proof it so you won't hurt yourself or try to leave."

A light tickling feeling on his crotch made Sam turn back to the diaper change. They powdered his crotch profusely. The smell of baby powder filled the room. It looked and smelled like a glorified daycare. Sam grew more upset but was quickly distracted by his semi-erect cock. The stimulation from the powder was enough to excite him. He knew he was doomed as soon as the girls saw it.

"Look, Karley. The baby is getting excited."

"He's definitely not a grower." Karley lightly pinched Sam's cock. He whimpered in response and his cock completely stiffened almost immediately. Strapped down as he was there was nothing he could do.

As sensual as Melissa could be, she leaned in and stroked Sam's hairless face. "Would sissy like the babysitter to take care of his little stiffy?" She lightly stroked his cock from the base to the tip. It was just a couple inches, but it was more than enough for Sam. He gasped and spasmed as his cock twitched. His load shot out across Melissa's fingers and onto his stomach. "Oh my god. Girls. Sam just came in under a second. From just one little stroke!" She looked down at Sam and laughed. "You're staying in diapers forever, little baby. You can hardly go a second without squirting on yourself." She took a baby wipe and gently cleaned Sam's cock and stomach as if it were as routine as any other part of a diaper change. After that he was taped into the diaper and released from the table. He was lowered down to the floor so that his diapered butt was placed on the carpet. The diaper crinkled loudly and the faint scent of baby powered surrounded him. There, seated on the floor, forced to look up at the women that surrounded him he truly felt like the baby they made him out to be.

"Your days of mistreating women are over, Sam." Katy took a step forward and glared down at Sam. "After what you did to Karley and Melissa, I'm sure you'll go right back to your old ways if I decided to give you another chance."

Sam's eyes grew wet. His lower lip trembled. "Puh-please. I'll be good. If you let me go back to how I used to look before the diary. You could keep the book. Use it to make me behave."

Katy sighed. She looked as if she were a mother that had to listen to her naughty child's excuses. "That wouldn't be much of a punishment, would it? No, Sam. You're going to stay in diapers. You're going to wear pretty dresses and suck on your paci until you learn to love it. You're going to cum and wet and mess yourself until you completely forget how to do those things if we ever let you out of your diapers." With each word Katy spoke, Sam felt smaller and smaller. He began to cry again. His girlish sobs were music to the girls' ears. 

"He looks just like the naughty little sissy he is." Rebecca teased. "Maybe we should put him down for a nap."

"He'll need his bottle first. Then a burping. Maybe some spankings to get him in a behaving mood." Karley added.

"A spanking?" Maxine asked. "He'd get nice and tuckered out after that considering he'd probably squirt in his diapies with each spank."

"You girls go on and take care of the rest of the house." Katy handed the diary off to Rebecca. "It should be apparent that a big baby lives here now and that he's a helpless little sissy named Sam."

Rebecca smirked down at Sam. She leaned and lightly patted his head. "You can say goodbye to all your fancy big boy things. What sissy baby needs a sports car. You'll hardly miss it when you're riding your rocking horsie."

"He'll need a playpen too. That way we can take him outside the nursery to keep a better eye on him."

"A baby bouncer too!" 

"And one of those toddler swings that have a seat he can't get out of."

Katy was beside herself with delight. "Doesn't that sound just lovely, Sam? You'll finally get to have that harem you've always wanted. Only now they'll be completely in charge of you."

With that the other girls left. They laughed and spoke amongst one another about all the things they had planned for Sam. They could be heard for sometime as they walked back down the hallway. Sam tried to shut out their words. The more he heard, the worse he felt. 

"Ready to go nap-nap, sissy?" 

Sam nodded. He was glad to escape his new life even if he had to endure a nap, diapered and pacified, in a bright pink crib. 

Katy knelt down and offered her hand. "Then let's go to the rocking chair and take care of some things first." She pulled him up and escorted him over to the large chair. It had more than enough room to fit Katy and Sam both. She sat down in the spacious chair and guided Sam next to her lap. "Go on, little baby. Bend yourself over my lap."

Sam could only grimace at the thought of being spanked over the knee by his ex-girlfriend. He had tried to do the very same thing back when they dated but she refused. She had claimed this was due to a lack of interest. He couldn't believe that he was the one that wound up across a lap instead.

At Sam's hesitation Katy placed a hand behind Sam's back and forced him down. She adjusted him until his diapered butt was positioned perfectly for a spanking. "You've been very naughty, Sam. You're going to spanked every day before your nap to make sure you've learned your lesson, understand?"

Sam nodded.

THWAP

With a firm hand she spanked his backside. "I want to hear you admit how naughty you were."

Sam bit his lip. His small dick had grown as hard as it could within the padding. Just as Maxine said, it was only a matter of time before Sam came in his diapers again. "I-I've been very naughty."

THWAP

A soft moan escaped Sam's lips. His lower body spasmed and he soiled his fresh diaper with a sudden burst of cum. Katy laughed aloud. "Did you really just cum again? You remember what was said earlier, right? With each little load of cum you pump into your pampers your already small dick will shrink. Keep it up and you're going to have a little clit between your legs."

"N-No...please!" Sam begged.

"You're the one coating your padding in semen. Control yourself and it won't get any smaller. Of course, this means you'll never cum again but something tells me you won't be able to stop it." Katy then grabbed the back of Sam's diaper and lightly tugged on the waistband. Sam squirmed in her lap as the thick padding pressed into his dick became almost too much to bear. "Are you going to cum again? So soon? Knowing your pathetic little baby dick will get even smaller. You probably have about an inch left now. Hardly anything to play with. Poor baby." She yanked the diaper up ever so slightly. Sam gasped through gritted teeth, determined to keep his manhood from shrinking anymore. "Struggling not to cum from a diaper wedgie? You really have become so depraved. I saw how much pleasure you were in when you were getting wedgied in your messy diapers. Your cute little moans were adorable."

"Please…" Sam paused for a moment. He knew she wanted him to humiliate himself. He decided to give in. For a chance to make things even just a little bit better. "...please...m-mommy. I-I'm gonna cum again."

Katy was delighted. "Good baby! Looks like you're starting to learn your place. Do you want mommy to go easy on you?"

Sam nodded.

"Then pee in your diapers."

"W-What?"

"I don't have the diary right now. I can't make you do it. You're going to prove to me how obedient you are and wet yourself willingly."

Sam hung his head low. He knew he'd do it. He just wanted off her lap. "Okay mommy."

"That's it. Be the obedient sissy baby you are."

Sam breathed deeply. He knew it would only make him feel worse but he had to start to give in. She'd go easy on him then. At least, that's what he hoped. With the last bit of his dignity gone, Sam made to wet his diapers. He strained for a second. He thought it would be hard to go. He worried that she'd spank him more if he couldn't go quick enough. But his bladder gave way almost immediately. Instinctively he tried to stop it. To wet just a little to appease her but he couldn't stop it once it started. He could only lie there, in Katy's lap, softly crying as he helplessly wet himself. 

"Oh my! You really had to go didn't you? Hardly ten minutes in a clean diaper and you nearly soaked them completely."

Sam felt awful. He wanted nothing more than his nap. The only thing that kept him from wailing like a baby was that he'd be put in his crib soon. Too bad for him Katy had other plans.

"Now that your diaper is nice and heavy and warm, it'll make your diapered wedgie feel even better."

"W-What?" Sam cried, panic in his voice. "But I was a good sissy, mommy!"

Katy ignored him. She yanked the waistband up as hard as she could and watched Sam's face for the exact moment he lost control. With a girlish moan he came again. He hated to admit it, but it did feel better to cum in the wet diapers. The warmth and slick padding felt incredible compared to before. It felt so good he couldn't contain his ecstasy. He moaned with each spasm of his cock. His mouth hung open and his eyes rolled back slightly. "Now you're a good sissy." Katy replied. "And didn't it feel so much better? Don't you just love your wet diapers?"

His mind nearly blank, Sam agreed without a second thought. "Yeeeees. I love my wet diapers so m-much."

Katy lovingly stroked Sam's hair. He was so much better then than he ever had been. "Do you want to be an even better sissy? Do you want to cum even harder?"

Sam's orgasm had ended at that point but the fog in his mind refused to lift. Between the spankings and his multiple orgasms he had begun to lose his free will. "Y-Yes mommy."

Katy leaned in close. "Poop your diapers. You know you want to feel that good again. You know you want to be a good little sissy for your mommy."

"Uh...ummm…" Sam wanted to. He couldn't help it at that point. But he still knew that he shouldn't. 

"Don't fight it. It's getting easier to go in your diapies each time you wet or mess. All you have to do is relax and you'll mess your diapers like the little sissy baby you are."

Sam was curious. Ever so slightly he relaxed and just as Katy said he felt his bowels release. "N-No...I can't stop. I-I'm gonna poop myself!"

"That's it, baby. Mess your diapers and mommy will take such good care of that tiny little stiffy that we both know is already threatening to squirt."

Sam grunted and his breathing grew ragged. More and more gas escaped his backside until the warm mush of his shame began to fill the seat of his diaper. He started to cry again. He had never felt so pathetic as he did then.

"Shhh shh, little sissy. You'll get used to it. Besides, mommy has just what you crave. A nice...messy...wedgie." Without warning Katy yanked the diaper up again. The thick bulge from his mess quickly spread out in Sam's diaper as the pressure forced it into a stinky mush against his rear.

Sam's mind went blank once more. He moaned loudly as his cock started to twitch. Katy was right. It was just what he wanted. "Guh...guh…" He babbled. The intense pleasure he felt was incredible. Some part of him knew then and there that he'd beg for it to happen again at some point. That he'd never have an orgasm so good as the ones he'd have in his messy diapers.

"That's it, sissy. Pump out all your happy juices. Enjoy how good your messy poop feels spread around in your diapies. Tell mommy how much you love it. Go on." Katy yanked him even higher. The diaper looked as if it threatened to leak or rip open at the tapes. And Sam had never looked happier.

"Bah...buh guh…" Was all he could manage as he orgasmed again and again. Each one forced him further into obedience. Each one made him hope he'd never escape his fate.

"Awwww...did baby forget how to speak? That's alright. Mommy will get you to say it soon enough." At that she lowered Sam back onto her lap. She then flipped him over and gently pulled him up to her chest. "Since you were such a good sissy, mommy's going to give you a nice little treat." She unbuttoned her blouse and exposed her breasts. Sam blinked slowly. His dull brain hardly recognized what was before him. "This will be the only time you'll get to be near a girl's breasts ever again. Hope you savor it, Sam. You'll need to be a very good sissy to get this again."

Sam perked up as his post-orgasm brain started to clear up. He remained perfectly still and quiet as Katy guided his lips to her nipple. With the thumb sucking habit he had developed he latched on with ease and suckled in a consistent and gentle rhythm. Katy smiled down at him. Sam was almost completely unrecognizable now. He had sissified further over the course of his punishment. He might have been mistaken for a girl if someone saw him from across a room. With her free hand, Katy massaged Sam's diapered crotch. She couldn't even feel his dick through the padding anymore it was so small. What she could feel was the sudden warmth in his diaper and the small breaks in Sam's suckling as he orgasmed again and again. By the time Katy pulled him back, Sam looked ready to pass out. 

"Looks like someone needs a nap in his cute sissy crib." She pulled him off her lap and guided the sleepy sissy over to the crib. Katy lowered the bars and helped him lay down. She strapped him in with some pink restraints that were stored at each corner of the crib. She had no need to but she enjoyed the sight nonetheless. "Looks like my little sissy gets to sleep in his messy, cum-soaked diapers. You wouldn't have it any other way would you? Such a little mess-maker." Katy reached down and pulled a diaper free from the drawer. By the time she slid it under his butt he was fast asleep. Double diapered and restrained, Sam would awake to find himself completely helpless. As an added humiliation, Katy put his pacifier back in his mouth. Almost immediately he suckled on it just as he had with Katy's breasts. "If there's any bit of your old self left in there Sam, then you're just going to hate when you wake up. We've got a lot in store for you and by the time we're done you're going to love your new life as our cute little girl.

Chapter 3

Sam was in an office building he had never seen before. He sat in a leather rolling chair in front of a crowded room of professional looking people. He couldn't see their faces but he knew they all admired him. They all saw a confident and successful man capable of anything. It felt right. Sam had worked hard for everything he had, hadn't he? Suddenly he felt unsure. A heavy book appeared in his lap. It looked different than he remembered but he knew it was the diary. That's right, he thought, I didn't earn this. I--the diary made this happen. It was then that Sam noticed the three women that stood amidst a crowd of blank faces. A blonde, a redhead, and a brunette. They were all beautiful and oh so intimidating. Sam couldn't help but get an erection. He used the diary to hide his shame. His face turned a soft shade of red as he nervously looked about the room. The three women knew he had not earned it. They approached him slowly, their eyes locked in on the book. Sam wanted to flee but he couldn't. How embarrassed he would be if the whole office saw his erect penis. 

"Hi Sam," said the redhead, "I think you have something that doesn't belong to you." She pointed to his lap. She pointed to the book.

Sam couldn't speak. He could only shake his head as the three women surrounded him. The rest of the office looked the same as before, faceless and unmoving; but Sam could feel a scrutinizing glare. As if the whole room had suddenly become aware of his secret.

"You're saying that it is your diary?" Asked the brunette.

Sam nodded.

The blonde giggled. "That's so cute! To think we'd been calling you Sam…"

Sam was confused. He looked down at his lap to see that the plain journal had turned into a sparkly pink diary with the word 'Sissy' written in big bubble letters. In a panic Sam tossed the book to the ground and inadvertently revealed his erection to the room. 

The entire office burst out into laughter. The three women laughed the loudest of all. "What's the matter," asked the blonde, "does Sissy not like her diary?"

Sam shook his head profusely. 

The red-head picked up the diary and opened it to a random page. She giggled behind her hand and showed the rest of the room what she had found. With a mocking lispy voice, she read the passage aloud. "Dear diary, today I've been a naughty little sissy. My mommies decided to punish me by showing the whole office what a big baby I am."

Sam's perception shifted seamlessly and suddenly his erection was nothing more than the bulge of a thick diaper. The leather rolling chair had been swapped out for a wooden highchair. His wrists and ankles were snugly restrained with a set of soft pink restraints. They looked easy to break but Sam was far too weak to do so. He tried to beg for help from his spectral coworkers only to have his speech turn to infantile babble around the large pacifier stuffed in his mouth. 

"Awwww...does the little sissy wanna say something?" The brunette teased him. "Does it have to do with how happy you are in your diapies?" She reached down to Sam's crotch and suddenly the zipper to his slacks were the snap crotch of a frilly pink onesie. She unbuttoned them and the thick padding of his diaper was fully exposed. The faintest outline of a bulge could be seen. 

"Baba hmmph gaaa!" Was Sam's response.

The women fawned over him. The blonde was especially eager to toy with him. "Aren't you gonna use your big boy words? Go on, spit your paci out and show everyone you aren't a silly little sissy baby."

Sam tried his best to do just that but each time he tried the pacifier would just go right back in. He knew he wanted to speak like the man he was but to everyone else it looked like he sucked on his pacifier, too shy to speak like a big boy. The longer it went on, the more Sam's perception changed until he believed he didn't want to speak. Drool dribbled down his chin as he noisily sucked on the pacifier. It made him feel calm despite the utter humiliation he suffered.

The redhead lightly tickled his chin. "Looks like he is a little sissy baby!" 

"Is that what you are," asked the blonde, "a good little sissy that does everything she's told?" She placed a hand on his diaper and gently squeezed. 

Sam moaned around the pacifier. He was incredibly aroused. His feelings of embarrassment faded away as his desire to orgasm peaked. Without a second thought he nodded.

"Then he a good little sissy baby and fill your diapies. Make the nice big mess I know you're just aching for. Then, once you show everyone what a good little pamper pooper you are, you can squirt your pathetic little load out while everyone watches."

Sam was conflicted for a moment. The briefest moment. He hadn't realized it earlier but his stomach hurt. The desire to poop was already there but there had been no toilet in sight. Stuck in thick diapers as he was, Sam couldn't help but let his bowels relax. His small flaccid cock gently pressed against the thick fabric of his diaper and he knew he couldn't take another second. With a grunt he gave the smallest push and messed his diapers. He leaned forward in the seat and gasped in pleasure as he felt his diaper sag from the stinky mush that threatened to overflow the thick padding. The entire room watched with glee but Sam's eyes were firmly fixed on the blonde. She smiled back at him.

"That's my good girl. No real man would ever dress up in pink and willingly poop himself. You're just a silly little sissy, aren't you?" The blonde pushed Sam back so that he sat in the mush. It spread to his crotch just in time for Sam to ejaculate into the messy padding. He gasped and whimpered around his pacifier in a very girly voice. "Awwww...did squirting in your diapies make you extra silly? No big boy left in you. Just a helpless little baby. Can you say mama widdle baby? Ma...ma?"

"Mmmmmph...ma...ma…" Sam gasped as he rocked back and forth in the sticky mush. Drool dripped down his chin onto his onesie and he looked every bit the silly sissy baby the women made him out to be. 

---

"Ma...ma...mama…." 

A soft mewling voice called out from the fading darkness. As his dream faded away into a distant and vague memory, Sam's vision adjusted to the dimly lit room. He groaned aloud and was shocked to hear the same girlish voice that had woken him up. He tried to sit up only to be quickly reminded of the straps that held him nearly spread eagle in the oversized crib. The faint scent of talcum powder wafted through the air but did little to cover up the overwhelming stench of the mess Sam had just pushed out into the thick princess print diapers taped snugly around his waist. 

"Mmmmph...ga...ba…" Sam could barely say more than a syllable at a time around the large nipple in his mouth. As far as he could tell there was no strap that held it in like a gag. He kept the pacifier in his mouth and sucked on it all on his own. One reminder among many of how much control Katy and her friends had over him now. "Ba…" Sam cursed under his breath. The events of the past night came flooding back to him. Just as the mess in his diaper was real, so was his orgasm. His already tiny dick must've gotten even smaller. Much like his petite and feminine body, his cock would only get more pathetic with each use of his diaper.

"Good morning, sissy." Katy's silhouette was in the doorway. "Mommy heard you making cummies over the baby monitor. Smells like you went boomboom in your sleep. You really don't have any control anymore, do you?" She flicked on the princess lamp next to the door and illuminated the room. The sudden brightness caused Sam to squint and look away. Katy approached the crib as his eyes adjusted to the light. She smiled down at him from behind the crib bars. "You're even cuter than I remember. Makes sense with how full and squishy your diaper looks." Katy lowered the crib bars. She then unbuttoned the crotch of his onesie and gave the crotch of his diaper a firm squeeze. 

"Mmmmmph! Na--nuh…" Sam had never felt so helpless. The crib, diapers, restraints, and pacifier in his mouth all helped to cement his new life as Katy's sissy baby but the worst part was that he felt a growing desire to give in. The mere squeeze of his diapered crotch threatened to make him cum. He couldn't even feel his cock press against the padding anymore. Could he even get hard or did his cum just dribble out his cock like the drool down his chin? He didn't want to think about it. It was bad enough that his body had become so feminie and petite. His small breasts and puffy nipples were plain to see under his pink onesie. His girlish whimpers not only gave away his arousal but also served as a constant reminder that he was more girl than man at that point. Though he'd never admit it, Sam couldn't deny it any longer: he was a sissy in every sense of the word. 

"Aww...did little Sam almost make cummies in his diapies? Do you love your mommy that much?" Katy leaned in and gently tugged Sam's onesie up to his lower stomach so that the full diaper was exposed. "Look at the mess you made! There's no way I'm ever letting you back in big girl panties." She ran her hands down Sam's smooth, feminine thighs and smiled. "Though I might let you wear some over your diapers so you can pretend you're a big girl. That is if you admit you're a diaper dependent little baby first...but we'll get there. For now, why don't we take care of this." Katy lightly patted Sam's crotch. She reached under the crib and grabbed a container of baby wipes, a bottle of talcum powder, and a thick pink diaper. She made a show of retrieving each one. One reminder after the other that Sam was a big baby and needed to be treated like one. "Oh! I forgot to ask. Mommy knows how much her little sissy enjoys a nice messy diaper. Did you want mommy to leave you in them for breakfast? I bet they'll be extra squishy and fun when you're all snug in your high chair."

Sam's eyes widened. He felt a flush come to his face at the suggestion, as if some small part of him secretly craved it. He pushed the feelings down and did his best to dissuade Katy. "Nuh! Nuh na!" He babbled. 

"What's that sweetheart? You need to take your paci out and use your big boy words if you wanna act like one. Keep babbling around your paci like a little baby and mommy's gonna treat you like one." She leaned forward as she spoke so that her face neared his. Her right hand slipped back down between his thighs and pressed against his squishy crotch while her left slipped a finger under the ring of his pacifier. "Tell mommy what you want. Go on…" As her right hand gently massaged the crotch of his diaper, the left lightly tugged at his pacifier. She smirked down at Sam as his body betrayed him. The thick crotch of his diaper rhythmically pressed into her hand as he closed his eyes and sucked the pacifier back in his mouth.

"Buh...ba ga…" Sam could barely form a single word as his arousal peaked. He wanted to cum so badly, but Katy kept the pressure on his dick light and purposely moved her hand so that he had to make his intent known. As humiliated as he was, Sam couldn't help but desperately hump the air.

"What did mommy say about using your words? Aren't you a big boy? Didn't I see you acting like a big strong man the other day? Using women like playthings…" She pulled the pacifier free from his mouth with an audible pop. "Tell mommy what you want. Are you a man that wants to keep his dignity…" she removed her hand and motioned to the changing supplies, "...or are you a little sissy baby that wants mommy to keep him in his messy pampers?" She placed her hand back on his diaper and gave his crotch another firm squeeze as if to emphasize her point."

Sam had no sense left in his brain. He could barely think straight and wanted nothing more than release. In as hoarse a whisper his squeaky voice could manage he stammered out, "M-Messy puh-pampers…"

Katy grinned devilishly. "Speak up, sissy. Tell mommy what you want."

"K-Keep me in my messy p-pamp...pampers please, mommy!" He was so close. Any illusion of dignity he had tried to maintain was gone. All he wanted was to cum. He'd say whatever she wanted. Unknown to him at the time, those words were just what he craved too.

Upon hearing those words, Katy removed her hand and stood up straight. She popped the pacifier back in his mouth and smirked down at him. "You're such a spoiled little princess getting what you want. But mommy doesn't mind." Katy tucked the powder, wipes, and diaper away and then retrieved an ever thicker diaper. "Those messy diapers are looking a little full though. I'll double diaper you just to be safe."

Sam could only whimper and stare up at the rainbow mobile that slowly rotated above his crib as Katy made a slit in the crotch of his diaper and then slipped the second, even thicker diaper under his bottom. He closed his eyes and tried to strain his muscles against the restraints but his was too weak to even get the cheap restraints to budge. His crotch tingled slightly as the second diaper was pulled up between his thighs and taped in place. The thick padding forced his legs apart and smushed the mess he had made even more. 

"Looks like your diaper is too thick to let me button your onesie back up. Guess you'll have to eat in just your diaper for now. But don't worry, sissy. Mommy has plenty of cute little dresses to put you in after nummy nums. You're going to be such a darling little princess!"

---

Maxine and Rebecca had joined Katy and Sam in the kitchen once Sam had been stripped of his onesie and strapped into the pink plastic high chair. They all regarded him with varying degrees of interest and amusement. Long gone was the man who had forced women into doing whatever he wished. Sam's ideal male form had been changed so much that he now had the body of a flat chested college age girl, and a petite one at that. His hair reached well past his chin and his features were soft and sweet. His thighs and waist were as feminine as could be and his breasts had developed even further into a modest pair of A-cups. His soft pink nipples just barely poked out from underneath the frilly bib they had put him in and were hard in the chill of the kitchen. He quietly sucked on his pacifier as they watched him. 

"He doesn't even look like Sam anymore," said Maxine, "I almost feel bad gendering him as male."

Rebecca chuckled. "Does he even have a dick anymore? Last I saw it was barely half the size of my pinky." She held the finger aloft and bent it down. "Maybe even smaller."

Katy nodded. "You heard him on the baby monitor. Squirming and gasping for his mommy." She opened the fridge and pulled out a jar of pink paste. "He definitely squirted in his diapies. Probably can't even get hard anymore."

Sam tried his best not to cry. Every time he thought he had reached rock bottom, his captors managed to make him feel even more pathetic. Thanks to their use of the diary, he could only sit there in his messy diaper and suck on the pacifier. Not that he could move if he wanted to. He had already tried to work the baby-proof locks on the seat but was too weak to work his fingers past the thick padding of his diapers to get to it. They'd made him completely helpless and dependent on them and now they spoke about him as if he weren't even there. In their eyes he wasn't an equal anymore. Not in any sense of the word. 

"Did he really beg to stay in his messy diapers?" Asked Rebecca.

Maxine giggled. "Oh yeah. I started recording the baby monitor while you were out. Listen to this." She pulled her phone from her back pocket and pressed play on the recording app. Sam's new, effeminate voice rang loud and clear as he begged Katy to keep him in his diapers. All three of the women laughed hysterically. 

"Oh my god! If only we got video of this." Said Maxine.

"We could use the diary to fill this place with cameras," mentioned Katy, "I'm sure there's plenty of people online that would pay to see our little sissy here fill his diapers."

"Not that we really need the money," said Maxine, "thanks to the diary we've got our own baby-proofed mansion." 

Rebecca grinned. "That's right! Sam hasn't even seen what we've done with the place yet. What we did with all his fancy appliances and that stupid sports car."

Sam started to cry as they continued to mock and shame him. He had hoped the sight might cause them to ease up but it only emboldened the women. They all laughed at his pathetic display.

Katy approached Sam and gently stroked his cheek. "Poor baby must be hungry. Girls, why don't you both give Sam his nummy nums while I see to adding some finishing touches to Sam's new home." She handed off the jar to Rebecca and left the room with the diary in hand. The two girls grinned from ear to ear as they approached the high chair. 

"What's even in this?" Rebecca asked. She opened the jar and stuck her pinky in the paste. She licked her finger and looked over at Maxine. "It's so bland. Surely we could make this tastier for our little princess?"

"I have a few things in mind…" said Maxine. She gave Sam an evil look before she ran to the cabinets and searched through them. "Let's see...castor oil...hot sauce...anchovy paste. All the essential items in a little sissy baby's diet."

Sam watched in horror as the two women mixed the paste and their collection of horrid ingredients into a large jar. He could smell the putrid mixture as they approached. His eyes watered as they yanked the pacifier from his mouth and pushed a heaping spoonful to his lips. He kept his lips firmly sealed. To his surprise the two seemed to be thrilled by his resistance. They whispered to one another before Rebecca quickly left the room. 

"Come on, sissy. Open wide for your num-nums!"

Sam refused. He turned his head with his lips tightly closed. He didn't care how infantile he looked. He refused to put the mixture anywhere near his mouth. 

"I suggest you do it before Rebecca gets back."

The threat caused Sam to raise an eyebrow. He could guess what would happen when Rebecca returned but he'd sooner be forced into eating it than willingly doing it. He remained steadfast and kept his mouth closed as Maxine tried to force the spoon in. He kept this up until Rebecca returned, diary in hand. 

"I see the sissy isn't wanting to eat his food still. Some even got on his bib. You look more and more like a big baby with every passing second Sam." Rebecca teased him. She opened the diary to a fresh page and started to write. Maxine stood up from her seat and watched over her friend's shoulder. They both laughed as Rebecca finished and closed the book. 

"Would you like the honors?" Maxine asked Rebecca. 

The redhead nodded and sat down in front of the high chair. She produced an even bigger spoon and scooped a heaping helping of the smelly mush. Rebecca then pressed it to Sam's lips and gently prodded. "Come on, sissy. Last chance to pretend you're a big boy in front of the two women that once thought you were a man. Just open up and get it over with."

Sam shook his head profusely. 

"Oh well. This will be more fun anyway." With a flourish, Rebecca lifted the spoon high in the air and made a whooshing noise as she mimed an airplane with the utensil. "Here comes the airplane! Open up for landing little sissy."

Sam's mind went blank and he became utterly delighted by the sight. He clapped his hands together and giggled as he opened his mouth. "Airpwan--mmmph!" Completely lacking any control he obeyed the wishes of the diary and swallowed the disgusting mush. The smell and taste revolted him to no end but his body betrayed him and happily asked for more. "More airpwane!" He asked, a stupid grin on his face. Spoonful after spoonful of the mush was forced down his throat while he giddily begged for it like a little baby girl being fed her favorite food. With no regard for his appearance or anything else aside from obeying the diary, Sam smacked his as the mush dribbled down his chin and onto the bib. This continued until the jar was completely empty at which point Sam returned to his normal self. Almost immediately he felt sick to his stomach. Between the utter compulsion to act like a brainless sissy and the disgusting baby food mixture, Sam felt as if he might throw up. Unfortunately for him, the food was staying down.

"What a good baby eating all your food!" Rebecca praised him in the most sickeningly sweet tone. She cleaned his face and neck with the clean side of the bib and then freed him from the chair. He tried to get his footing and run but his diaper was too thick and he fell down to his hands and knees. "Ah ah ah! It's not playtime yet! You've got a full tummy. You know what that means?"

Sam looked up at Rebecca and Maxine with a look of fear plain on his face. "N-Nuh uh."

Maxine leaned down and grabbed him by the waist. With ease she lifted him from the floor and placed him on her hip. She lightly tickled his tummy and kissed his cheek. "It means it's time for burpies!" The two women escorted him into the living room where a princess movie played on mute in the background. Maxine sat down on the couch and gently began to pat Sam's back. Despite it's innocent nature, the act felt like one of the more humiliating things he had experienced. Especially since he faced the back wall of the living room. The majority of which was taken up by a large mirror. For the next thirty minutes he was forced to watch himself be burped like an infant while Rebecca and Maxine talked about their days like he wasn't even there. It felt like some awful dream. The person he saw in the mirror looked nothing like himself. They looked and sounded like a girl in every sense of the word. Even his burps were feminine and cute. To make matters worse, his stomach felt worse by the second. Even while the gas dissipated the pain grew until Sam started to audibly show his discomfort. 

"Aww! Does the little sissy have an upset tummy?" Maxine teased him. "Here, baby. Let auntie Maxine take care of that for you." Sam was turned around in Maxine's lap and placed on her knee facing the TV. His pacifier was stuffed back in his mouth as his arms were pinned behind his back. He was left helpless but to watch the princess movie and suck on his pacifier as Maxine bounced him up and down on her knee. "Does this feel good, baby?"

Sam remained silent aside from the occasional whimper. Rebecca turned the TVs volume on and Sam was left to learn about the power of friendship from some cartoon ponies while the women he had humiliated only days prior laughed and teased him. With each passing second his stomach felt worse and worse until Sam couldn't take it anymore. With no strength of shame left in him, Sam was powerless to fight as his bowels released and his diaper was filled to the brim with the smelly aftermath of the hot sauce and castor oil concoction. 

"Rebecca! Rebecca look! The sissy baby is filling his diapies!"

Rebecca didn't need to look. Sam's mess was smelly and noisy enough to be painfully apparent. The redhead plugged her nose and waved her hand in front of her face. "Oh my god what a stinky baby! No wonder he needs diapers if he makes messes like that!"

Sam started to cry as the two women mocked him further. He was helpless but to let his body do what it pleased. He filled his diaper to its limit and helplessly soaked the crotch of his diaper in the process. Tears and snot poured down his face as he sobbed around his pacifier. And to make matters worse, as his stomach pain and the shame of his accident receded, his arousal rose. The rhythmic motions of Maxine's knee bouncing combined with the diaper's thick padding and the diary's conditioning meant he was mere moments away from cumming in his messy diapers. He couldn't bare to humiliate himself even further but it was all he could do to control himself with each bounce upon Maxine's knee. He desperately tried to focus on anything aside from the pleasure emanating from his crotch but his willpower faded fast. Drool coated his chin and dribbled down his neck to his breasts. His erect nipples felt incredible as his spit coated them. The cooling liquid sent shivers down his spine until he was mere moments away from cumming.

"Oh my gosh," cried Rebecca, "I think the little sissy princess is getting off to this! Look at how hard his nipples are. And the lewd expression on his face!"

Maxine giggled with glee. "Is that so? Well he was such a good sissy eating all his food like that. And he was so obedient during his burping. Didn't even try to fight it. I guess our sweet pamper princess deserves a little fun!" Maxine grabbed the waistband of Sam's innermost diaper and yanked it upward as hard as she could. 

Sam gasped. The pacifier fell from his mouth and a girlish moan escaped his lips. He couldn't feel himself ejaculating underneath all the padding. All he knew was that the mess being wedged against his backside from the diapered wedgie was one of the most amazing things he had ever felt. His back arched in pleasure as he came again and again until he eventually collapsed backward onto Maxine. He basked in the afterglow of his depraved pleasures. He rocked his hips back and forth in the mess as Maxine lightly massaged his developing breasts.

"What a display, you depraved little thing." Rebecca squeezed the front of his diaper and Sam came again, not as hard as before, but it didn't matter. Each time he came the diary changed him further into the depraved baby girl they wanted him to be. In that moment Sam didn't care. He felt no shame in how much he loved his messy diapers. He even mumbled it under his breath as his vision faded. There, in the messiest diaper he had ever made, Sam passed out. Maxine and Rebecca fawned over their pathetic pamper princess. They were eager to share what had just happened with his mommy.

---

Sam awoke nearly an hour later to the sound of hushed conversation. Rebecca and Maxine had placed him in a playpen full of toys and stuffed animals in a room Sam had never seen. The pacifier he had grown so used to could not be found. He tried to act as if he didn't need it but quickly caved and scoured the playpen, completely unaware of the changes that had occurred to him since his multiple orgasms in Maxine's lap. The increased weight on his chest, his more petite body, and the distinct lack of something between his legs. That last one was difficult to notice thanks to the two thick diapers he had been snugly taped into. He had been changed in his sleep. The brief nap had been a fitful one and Sam wanted something for comfort. He didn't care how ridiculous he looked. When he eventually couldn't find it amidst all the stuffed animals he tried to escape only to fall back on his pampered butt, too weak to swing over and too clumsy to work the child locks. In a fit of desperation he sucked on his thumb and clutched a stuffed animal to his chest. It was in that pitiful position that the three women found him. 

"I see our little princess is awake," said Katy, "you're becoming such a good girl, aren't you?"

"All that talk and misuse of the diary and yet here you sit sucking your thumb like a helpless little baby." Rebecca teased him.

Maxine held aloft a large pink pacifier and dangled it over Sam's head. "Is this what you want, little girl?"

Sam reached for it without thinking. Maxine yanked it away at the last minute and left him painfully irritated. "I'm nah a widdle girl!"

"Look how cranky the baby gets without her paci. That's the first bold thing she's said all day." Katy grabbed the pacifier from Maxine and leaned in to get a better look at Sam. "You are a little girl. Did you not notice your breasts or the cute pigtails we put your hair up in? You even sound like one. The only people that know you used to be a man are in this room."

Sam scowled as best he could. A hard task given the thumb he had stuffed in his mouth. "I'm nah a girl…"

Rebecca and Maxine looked at one another. "Did you forget what you did before your little nap?" Rebecca asked.

"And how many times you did it?" Maxine added. "Remember what your mommy said about going in your diapers?" 

Sam looked at them confused as they laughed down at him. Katy just rolled her eyes. She opened the playpen door and gently pushed Sam onto his back. He tried to resist but the woman was far stronger than him and held him down easy. She then untaped his diapers and motioned for him to look. Sam couldn't believe his eyes. His cock was gone.

"Wuh-what?" He whimpered.

"Little sissies that use their diapies have their dick shrunk to match how pathetic they are. You kept using and making stickies in your diapies so you lost yours entirely…" Katy slipped a hand down his lower stomach and gently started to massage the mound of flesh that was left. Sam gasped at the sudden realization. His cock had been replaced with a pussy. 

"No! B-But--"

Katy shushed him. "Too late. Like it or not, you're a girl now. You won't ever use that pathetic dick of yours to violate a woman ever again. A fitting punishment for you." Katy stood and left Sam with his diaper still open on the floor. She bit her lip and looked back to her friends. "Why don't we get our little girl up on her special rocking horse?"

"Wha-what are you doing?! Let me go!" Sam kicked and struggled but the women just laughed it off. It was like holding an unruly child and nothing more. He was far too pathetic and weak to be taken seriously. 

"We're going to show you what it was like to be one of the girls you had fun torturing," said Rebecca, "only you're going to actually love this, unlike those poor girls."

Sam looked around the room to see where they would take him. In the far corner of the room was a large rocking horse with its head down as if it were eating grass. The three women placed him atop the piece of furniture with his butt and pussy just off of one end while his head rested at the other. Straps and restraints were used to hold him firmly in place. Once he was secure the three women went to the front of the horse and looked down at him with sneers on their faces.

"It's fitting, isn't it? You spent all your time with the diary harassing women and now you're the woman being harassed." Katy slipped her fingers under the waistband of her skirt and tugged it down until it fell to her feet. This left Sam mere inches away from the massive cock that strained against the thin fabric of her red lace panties. Maxine and Rebecca followed suit and together they all slipped down their panties so that their massive erect cocks stood at full attention. Sam couldn't help but stare. 

"Look at the little girl!" Rebecca teased. "She's practically drooling over your dick, Maxine."

Maxine giggled. She placed her petite hand at the base of her cock and approached Sam. "Does baby want her paci?"

Sam snapped out of his stupor at the mere suggestion of him giving her oral. He hated how strange it all made him feel, how the lack of pacifier had caused him to feel petulant and make him drool. "Get that away from me!"

Maxine pressed the swollen head of her cock to Sam's lips. He kept them sealed and turned his head but it didn't keep Maxine's precum from getting on his face. "Oh! I know what she wants." Maxine winked at Rebecca. She wagged her cock back and forth and made a whooshing noise with her mouth. "Open up! Here comes the airplane." Sam immediately opened his mouth with an excited expression on his face. Maxine slid her head past his lips until a quarter of her length was in his mouth. Once there she gripped him by one of his pigtails and laughed. "Worked like a charm! Okay girls, fight over who gets to cum in our little princess's pussy."

"Mmmmmph!" Sam couldn't speak with Maxine's giant cock in his mouth. And between the airplane bit and his growing need for a pacifier the swollen member almost made him feel at ease. Not that he could resist. They had rendered him completely helpless but mentally and physically. All he could do was lay still on the horsie as she gently started to thrust herself in and out of his mouth. 

"I can see why you liked this," said Maxine, "it feels so good to have this much power over you. You look so cute and helpless as our little cumdump."

Tears had started to form in Sam's eyes as his gag reflex kicked in. Maxine's cock was huge and the biggest thing he had ever had in his mouth was his pacifier. It didn't matter how he felt though. Maxine would get what she wanted, just as Katy and Rebecca would. They were just as large and twice as eager. The feeling of their hands spreading and lubing up his other holes was enough to remind him that the cock in his mouth wasn't his biggest concern.

"You want a go at her pussy?" asked Katy.

"I think her mommy should have her virginity," replied Rebecca, "You hear that, little girl?" She slapped his ass. "Your mommy is gonna be the first cock to penetrate your new pussy. Be sure to thank her once we're done with you."

"Mmmmph!" Sam flexed against the restraints but it was no use. They would get what they wanted. All he could do was just lay there and take it. He resigned himself to it as Maxine picked up speed. The taste of her precum coated his throat as the head of Rebecca's cock pressed its way into his butthole. He would've gasped in pain if he hadn't already been blubbering around Maxine's cock.

Katy's dick was next. The massive member pushed its way in a couple inches and picked up a rhythmic pace with the other two. Sam's face was covered in tears and drool as Maxine slid in and out of his mouth. His ass ached as Rebecca picked up speed with little regard for his comfort. Slowly, Katy pushed her way in further and further until all three of the women were thrusting the full length of their shafts in and out of Sam's holes. All Sam could hear was the wet slapping of their cocks sliding in and out as a feminine voice gasped every couple seconds. The gasping turned to soft and ragged moaning as Sam's soft feminine body gave into his base desires. There was no pride or manliness left in him as they all penetrated him. His mind was empty save for the desires and pleasures of a man completely broken down into a girly cock sleeve. 

Maxine came first. She gasped and gripped Sam's pigtails as tight as she could as she left the full length of her cock in his mouth. Load after load was emptied into his throat and he took it all until it started to spill past his lips, down his chin, and drip down to the floor. Once finished, she released him and fell back on a chair. Sam was left with his mouth agape. His quiet whimpers turned to loud moans as his full focus turned to the utter destruction of his ass and pussy. Maxine's cum spilled past his lips as his eyes rolled back in his head. He had never felt such incredible pleasure.

Rebecca was next. Sam could hear her moan loudly as her thrusts picked up speed. Katy's cock left him for a moment as Rebecca gripped his hips and thrusted full force into his ass. Sam, with no sense left to him, moaned with his mouth agape. He gasped and grinded his hips into the wooden horse as Rebecca gripped his pigtails and took full control of him. When she came Sam did too. His entire lower body shook as he squirmed and begged for more pleasure. Rebecca laughed aloud as she slammed into his ass. Never had she felt so in control as she did then. When her cock left Sam's backside, cum started to pour from his ass. Katy took the liberty of stuffing a massive plug into Sam's ass just before putting herself back into Sam's pussy with the same speed as before. 

Sam dutifully licked Maxine and Rebecca's cocks clean as Katy took her sweet time fucking his pussy. The pleasure was so intense that Sam nearly forgot how to properly lick. Maxine and Rebecca were more than happy to show him how to properly do it and before long, Rebecca's fully erect cock was thrusting into his mouth as Katy neared her own climax. Sam came again as Rebecca finished on his face. She demanded that he beg for it but his words had turned to infantile babble as Katy thrusted into him even harder. Sam came two more times before Katy finally ejaculated inside of him. His body spasmed just as her cock did. He could feel each time her cock twitched inside of him. The pleasure was so intense that he nearly passed out. Cum coated his face, ass, and thighs. Even more dripped from his new pussy. Drool and cum dribbled from his lips as he tried to recollect himself. It was no use. They had fucked Sam silly. He could hardly see straight as Katy brought her semi-erect cock to his mouth. Like Rebecca and Maxine before her, Sam dutifully cleaned every inch of her dick. She smirked down at him as he did so. 

"Good girl."

---

After their fun on the rocking horse, Sam was officially broken in. They all knew it and relentlessly teased him for it every time he would whimper and beg to be given back his potty training. Katy, Rebecca, and Maxine had taken a liking to not only their power over Sam, but everything else that came with the diary's influence. Katy and Rebecca both had decided to keep their cocks and all three women had grown rather fond of fooling around with one another. Each new day was a chance to find new ways to further humiliate Sam. Often times they'd give him the illusion of a chance at freedom only to pull the rug out from underneath him. Katy especially loved to tease him; in fact, she loved nothing more. 

"Awww...what's the matter, baby?" Katy teased him. She held him aloft by the waistband of his diaper. The thick padding was wedgied firmly up his backside. "I thought you loved your messy pampers?" The diaper sagged heavily from use. Sam had grown used to using them. Sometimes, he'd try to hold it. He'd try to waddle to the bathroom and take off his diaper when his captors weren't looking, but no matter how hard he'd try they'd find him and he'd wind up messing or wetting himself in whatever humiliating way they deemed fitting. "I've got you in two of the thickest diapers I could find. You shouldn't be shy to use them." She yanked the waistband up further and Sam whimpered. His new pussy was far more sensitive to wedgies in his used diapers. The wet and squishy padding felt incredible. He could only hope that it was the diary's doing and not that he actually had developed a craving for messy diaper orgasms. 

Sam had managed to make it just outside the bathroom. Katy had found him trying to work the baby proof door with his mitten covered hands. "P-Pwease...muh-mommy…" 

Katy grinned from ear to ear. "Such a polite little girl to beg to use the potty like a grown up." She yanked the waistband up again and Sam's hands dropped to his crotch. 

A soft moan escaped his lips as his body betrayed him. He felt his willpower falter. It was only a matter of time before he couldn't hold it anymore. 

"I'm surprised you can even hold it anymore. You already poop yourself in your sleep. Why don't you just give up already?" Katy asked him.

Sam whimpered and stuffed his thumb in his mouth. He had dropped his pacifier on the floor when Katy surprised him. He felt on the verge of crying. "N-No…"

Katy scoffed. "Well that won't do. We're just going to have to teach you a lesson then, aren't we?" Katy walked down the hall with Sam's wedgie pulled so high that he had to follow on his tiptoes. They entered the living room where Rebecca and Maxine relaxed on the couch. "Rebecca, would you help me teach our little girl a lesson?"

Rebecca clapped her hands together. "Gladly! What'd she do now?"

Katy pushed Sam forward so that he was between her and Rebecca. "She seems to think she can just hold her poopies like a grown up."

Rebecca raised an eyebrow. She bent at the waist and looked into Sam's eyes. "Naughty girl! You're wearing diapies for a reason." Rebecca looked to Katy and they both nodded. Sam yelped as they each grabbed a side of his diaper and wedgied him as hard as they could Sam gasped in a mixture of pleasure and pain as the thick, messy padding was pulled up so high that the front of his diaper covered his face. He weakly swung his arms to try and stop them but they just laughed as they pulled harder. 

"Nuh! S-Stop id!" Sam was helpless to fight as his arousal heightened from the increased pressure to his crotch. The slick padding slid against his already wet pussy and he orgasmed as Katy and Rebecca pinned the wedgied diaper together above his head. Stuck in his diaper, the smell of his own mess was unbearable. Even then, he still couldn't help but be aroused as Rebecca teased his pussy through the padding. 

"The only way you're getting out of your poopy diaper wedgie is if you mess yourself like a baby," said Rebecca.

Maxine laughed. "Look at how her thighs are shaking. She's loving every second of this!"

Sam tried to protest but could only babble incoherently as his pussy continued to be stimulated. He would never admit it but the pleasure was incredible. How low had he sunk that a messy atomic diaper wedgie got him off? He had never felt so pathetic as he did once he let his hands fall to his crotch and massage his pussy through the padding. 

"My god you're right Maxine," exclaimed Katy. "The depraved little baby likes her messy diapers." Katy spanked Sam's messy bottom and he fell to his knees. "Go on. Make a bigger mess. Show us how much you love your poopy diapies. Show us how big a baby you are."

Sam didn't want to. He chose to believe that his depravity was all the diary's fault. That he didn't really love how the mushy padding felt wedgied into his ass. He told himself that he just couldn't hold it anymore and that the girls had forced him to do it but deep down he knew that he craved it. Diary or no, Sam had sunk so low that when he pooped his wedgied diapers, he came harder than he ever had before. So much so that he fell forward as he orgasmed. His body shook as he pushed more and more of the smelly mush into his diapers. His already weak bladder gave way and he soaked the front of his diaper. He gasped and grunted as he humped his hands. He even continued to do so until the girls finally relented and freed him from his diapered wedgie.

Sam hid his face in shame as they changed him out of his messy diapers. Maxine and Rebecca teased him with a rattle and baby talk as Katy, his mommy, wiped him clean. 

"Face it Sam, you love your messy diapies," said Katy, "but that's not what I want. I want you to be so helpless you can't even control yourself." Maxine and Rebecca giggled to themselves as Katy revealed a few things from her diaper bag. Sam looked up to see an enema and a large butt plug. "It's time we trained you to be the big baby you were meant to be."

"W-Wait! Mommy pwea--" Katy silenced Sam with a pacifier in his mouth. Thanks to the diary he was helpless but to shut up and suck on it. He could only watch as Katy gave him an enema and stuffed the plug into his ass. 

Katy pressed down on Sam's stomach and he whimpered. He had just voided his bowels but he already felt like he needed to go again. His discomfort grew with each passing second as he was taped into a couple of thick princess diapers and brought over to his high chair. They stuffed spoonful after spoonful of laxative laced baby food into his mouth. Helpless to their airplane trick, Sam just giggled and acted like a baby as he gobbled down the disgusting mush. 

While Maxine and Rebecca handled his feeding, Katy picked up the diary and started to write. "I've taken away everything that compels you to act infantile. From now on, you're going to be completely in control of yourself. Which means every babyish thing you do will be of your own free will."

Sam felt incredible relief as he realized he no longer would be forced to suck on the pacifier or open his mouth to the airplane. That relief was immediately gone as Rebecca held his nose and stuffed another spoonful of laxative laced food into his mouth. 

"This means you'll need to be a baby or be punished. Just like the plug will train your butthole, we're going to train you mentally." Katy leaned over and grabbed Sam by his chin. You're going to lisp, crawl around, and play in your playpen like a baby or we're going to make things much worse for you. Understand?"

Sam swallowed down the mush and nervously looked away from Katy. He had hardly felt free for more than a second. 

"Do I make myself clear, little girl?"

"Yeth mommy…"

---

Over the course of the next week, Sam was trained to be and act like the little girl he had been forced to be prior. Every humiliating act became all that worse as he was forced to willingly do it all with a smile. Whenever he'd misbehave they'd bend him over their knee and spank him. The act was humiliating, not painful. Except for when the plug in his bottom would get moved. Each day they'd feed him more and more laxatives, give him an enema, swap out his plug for a bigger one, and make him beg for release only to deny it to him. Before long he didn't need to be prompted. His stomach ached and his butthole felt as if it were on fire. He didn't care how he looked anymore. All he cared about was release.

"Mommy…"

Katy turned to see Sam at her feet. The front of his diaper sagged from how much he had soaked his diapers since his last diaper change. He tugged at her dress and sucked on his thumb. He knew how to play the part of a pathetic little sissy baby. Even though they both knew that was all he was anymore. "Yes, little girl?"

Sam's face burned a bright shade of red. Every day he'd beg to be allowed to poop his diapers and everyday Katy would say no. His only hope was that if he degraded himself enough she might finally relent. Today he had drooled all over himself and the chest of the frilly pink dress he had been put in. He picked his nose and bounced up and down in his sopping wet diapers. "Mommy can I pwetty pwease make a big poopy in my diapies? I wuv going poopy in my diapies wike a siwwy baby."

Katy watched him humiliate himself with delight. The longer his training had gone on the more eagerly he had given in to his new role as their willing sissy baby. She bent down and lightly tousled his hair. "I dunno...are you a big dumb sissy baby that loves her pampers?"

Sam nodded enthusiastically. 

Katy smirked. "Open up the front of your diaper."

Sam knew what was coming. He had gotten used to it at this point. "Yeth mommy. Fank you mommy."

Katy pulled her panties down and pointed her cock at Sam. She aimed for the opening between the diaper and Sam's stomach and peed into it like a urinal. 

Sam openly masturbated while she did it. They had never asked him to do it, but he knew they liked seeing him as pathetic as possible. It was hard to get off at first but Sam eventually started to get used to it. The squishy padding felt amazing being pressed into his pussy. 

Once Katy was finished she grabbed Sam by his ponytail and pushed her semi-erect cock into his mouth. He continued to masterbate as she grew stiff against his tongue. He gladly let himself be used while he masturbated. "You've become such a good girl. Maybe I'll let you do it today. Would you like that?"

Sam looked up at his mommy with joy in his eyes. "Uh huh…" His stomach was in such pain. He had never wanted something so badly as to fill his diaper with poop. He'd do whatever they wanted. Say whatever they wanted.

"Rebecca? Maxine? Would you give me a hand getting our little girl's diaper ready for her poopy?"

Rebecca and Maxine entered the room. Rebecca pulled her own cock out and waited for Sam to willingly pull back the waistband of his diaper. Maxine watched gleefully with another diaper in hand as Rebecca pissed into the back of his diaper. Even as thick as both of the diapers were, it looked as if they were full to bursting by the time Rebecca had finished. Sam happily bounced up in down in the squishy diaper as Katy gripped the back of his head and thrusted down his throat. 

Katy smiled. "Oh I think our obedient little baby is finally ready." She pulled her cock free of Sam's mouth and pulled Sam's hands free of his diaper. "No more masterbating." She motioned to Maxine who then pushed Sam on his back and diapered him. With three thick diapers taped around his waist, two of which full of pee, Sam had no hope of even waddling around like a toddler. He had to crawl like a baby as the three women escorted him into the bedroom. Once his office, it now served as Katy's room. Just another part of his life that had been taken from him.

"Why don't you two have some fun while I get our little girl ready," said Katy. She sat down on a rocking chair and lifted Sam up into her lap. She lifted the frilly dress off his head and lightly pinched his exposed nipples. "Remember what I said, sissy. No touching your princess parts."

Sam nodded. He would never disobey. Not when he was so close. 

Katy continued to tease his nipples while she bounced him up and down on her knee. They both watched as Rebecca climbed atop Maxine and started to thrust into her waiting pussy. The two moaned and writhed on the bed. Their bodies rose and fell in unison. They moaned and gasped sweetly. Rebecca played with Maxine's breasts as Maxine wrapped her legs around Rebecca's waist.

The sight stirred something inside Sam. Something he hadn't felt in weeks. For so long he had gotten used to cumming from using his diapers, being spanked, and even having his diaper pissed in. He had forgotten how hot women's bodies were. The sight stimulated him in ways he hadn't been in weeks. He whimpered, wishing he could touch himself. To make matters worse, Katy's teased his nipples relentlessly. She used the drool collecting on his chest to moisten them. The sensation was incredible. He started to whimper and grind his hips but the knee bouncing prevented and thick diapers prevented the stimulation he so craved. "Mommy…"

Katy laughed. "What's the matter, baby? Remember what it's like to be a grown up? To have your parts played with by someone else?" Katy continued to tease his nipple with one hand while her other hand inched down to his diapered crotch. 

"Hnnng...yeth mommy…" Sam watched intently as Katy massaged his crotch. He waited for the stimulation to start but it wouldn't. He whimpered.

"Looks like your diaper is so thick you can't even get off with someone touching you. Poor baby…"

"Nuh...no...b-but…"

Katy laughed. "Don't worry baby. Mommy has what you want." She then pushed Sam forward and reached down into his diaper. 

Sam's eyes widened as the plug was pressed in further and the pressure in his bowels reached new heights. "Buh…" A pacifier was stuffed in his mouth and Katy removed her hand. She carried him a few feet over to the crib she kept in her room and placed him down in it. 

"Babies aren't allowed to play like that," said Katy. She reached back down and removed Sam's plug. He gasped at the sudden removal. "Babies fill their pampers and hump their stuffies, hoping that their full diapies will be enough for them to get off." She then lifted the crib bars back up and approached the bed.

Sam could barely focus. He tried to watch Katy strip and join Rebecca in fucking Maxine but his eyes forced themselves closed as his bowels gave way. He gasped and grunted around his pacifier as he lost all control and pooped himself. His hands clenched the crib bars as he filled his diaper. Sam wished so badly that he could be on that bed. That he could be with them. Too bad for him that the thick diapers he filled to the brim were too thick for him to even stand up tall enough to free himself. He started to cry as his trained desires came flooding back. He pinched his nipples and sucked on his pacifier as he straddled a teddy bear that had been left in the crib for him. He grinded his crotch into the bear as he watched the three women have sex. Drool dribbled down his chin and coated his erect nipples as he watched and wished that he could join them. "Buh...ga..ma…" His diapers continued to fill up as more and more of his laxative and enema induced mess was pushed out. The disgusting mush filled his diaper so much that even the front of the padding had grown sticky with the mush. Sam babbled and whimpered as his old habits took over. He bent over and humped the teddy bear harder and harder, desperately wishing he could cum but it just wasn't enough stimulation. He continued this pathetic act until his diaper nearly overflowed and the three women had long since finished. Tears streamed down his cheeks as he realized that his old life was over. He could feel how stretched his asshole had become. His days of holding it in were over. Katy had what she wanted. 

"Aww...look girls. Our little baby is upset that she can't get off in her messy pampers."

"Poor thing. She loves cumming in her poopy diapies."

"Oh well. She's just a dumb baby after all. She shouldn't be able to cum without her mommy's permission anyway."

"Should we change her?"

Katy stood from the bed and approached Sam's crib. Cum dripped from her cock as she rubbed his back through the crib bars. "No...it's nap time for her and she looks so happy in them. She can sleep in her poopy mess and think about how much she loves her diaper dependency. Maybe if she's a good girl mommy will piss in her diaper one more time before her diaper change. Would you like that princess?"

Sam nodded weakly from his position curled up in the crib. "Yeth mommy…" Much like his stretched asshole, Sam had no hope of ever recovering. 

"Of course you would. And why do you love it so much?"

Sam sniffled. He knew what they wanted and no longer had a shred of dignity left. "Cause I'm your pamper pooping widdle sissy pwinceth baby."

"That's right, Sam. And don't you ever forget it."