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wittlesissybaby

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Inside These Walls (Custom)

Andre felt so lucky to have found a dominant woman that was akin to his interests. They had only chatted online, but she knew exactly how to push his buttons. Sure, she was a professional Dominatrix, but he could swear it seemed like she understood him on a much deeper level.

He eventually ...

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Chapter 5 - Ding Ding Dingaling

“How’s the water, queer-bait?” Caleb asked.

But the boy didn’t answer. Just gurgled and floundered for air in the toilet water.

Caleb pressed his foot on the back of the boy’s head, hitting the lever to make it flush. “I’m sorry, f@gg0t! I can’t hear you…”

Ad...

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It Grows on You

"Why's your little guy so pointy? I thought you didn't like your diapers? But now your little acorn is growing into a...well, it's certainly not a tree, but a tiny twig might be the proper term!

You can stop pretending honey. It's okay. I'm sure when we first started your diaper punishment ...

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New Sorority Boys Chapter is Coming

Sorry for the delay, but the poll results showed most of you would like a new Chapter of Sorority Boys!

I have been working on it over the past few weeks, but I haven't had very much time to sit down and write, and the chapter is involving more than I originally anticipated. 

We'...

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Know Your Role

“Umm, you can wait!” She said with a harsh tone to the man on the couch.  “My husband needs his diaper changed.”

Stacy gripped the front of Mark’s pampers. “You see? He’s soaked.” She said matter-of-factly.

“I just don’t see why it can’t wait.” Jeremy said...

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Honey, I’m Home

Most men hate being bombarded by their wife as soon as they walk through the door. Asked to help with the laundry, help clean, or for something that needs fixing. But I think they would take that any day over what Toby has to endure.

“Hi, honeyyy!” Laura calls as he walks in. She doesn...

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Haunted Mansion

“See?” Annie said, squeezing Luke’s diaper beneath the frilly skirt. “No one even notices!!”

Luke had begged to differ. He felt like every single eye was on him, even the fake ones from the animatronics and masked decorations.

The party was lively though, so maybe the group ...

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Which Story Would You Like to See Me (Try) to Continue?

These are some of the ones I have ideas for. With everything going on right now, I can't make any promises, but I'll do the best I can!

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Diners, Drive-ins, and Diaps

“Dry your tears, little one.” Karen said to her husband as she unsnapped the buckles of his oversized car seat. “You need to get used to these sorts of things. If you’re going to wear diapers 24/7, we’re gonna have to eat at a restaurant eventually.”

The binky dropped from Guy...

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Trying not to lose my mind…

Things with my (ex)wife are getting ugly. I’m trying to not let it affect my work but it’s getting incredibly difficult. The last thing i want to do is write right now, but I know I owe you guys to put something out. The next story i have is not great. I’m not gonna lie. I hate it. I don’...

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What lengths do you prefer?

With me rolling out more captions and mid-length stories, I just wanna get an idea of what you guys enjoy most!

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Slurpies

Now I know this is hard for your wittle baby brain to understand, so let me paint you a pwetty wittle picture:

You’re going to give him a—hmmm—let’s call it a…’slurpie’. Yes, a slurpie!

That means you’re going to pull down his pants and those big boy undies you used to...

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Right here. Right now.

“You want him right here?” She asked, bending the little bitch over.

“Yea, right there.” I said, trying to contain the excitement dripping from my voice. I paced back and forth, my big black dick swaying to and fro. It was so throbbing hard it almost hurt. I dunno, man, something ab...

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Patron Only AMA

Hey guys,

I’m bored at work today so I posted an AMA on tumblr but I thought it would be fun to do one here too. You guys know my online persona probably better than anyone, and are most familiar with my works. So do you have any questions you’d like answered? I know things with this bl...

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DREAMS Daycare - Chapter 5

Naptime went off with only a minor incident.

The sissies were all arranged on their mats that were way too close to each other, and given blankies much too small for them. They were grouped according to the ‘Relief’ schedule on their charts. Those with strict chastity/orgasm restriction...

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Permanent Potty

Do you miss it? Being able to use the big boy potty?

Awww! I know you do, honeyy, but you don't have to cwy!!

This is what you wanted!! Remember?

You wanted to be 'diapered 24/7'. Those were your words, not mine. So I'm sorry that this isn't as fun as you thought it wou...

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Virgin Vagabond

“Lift up that skirt, slave.” Master said. “Let’s see that diaper of yours.”

Devin whimpered as he lifted the hem of his dress. Three months ago he was wearing normal boy clothes, he was using a toilet, and his dick was free to use as he saw fit. Not that he ever really used View Post

Men Rule, Sissies Drool

"Should we give him a bib?"

"Na..." Jason laughed, "I kinda like the look of the drooly baby getting his shirt all soaked with spit and cum."

He walked closer to the sissy, stroking his hefty, 8-inch cock. The sissy recoiled in fear, whimpering and moaning something inaudible with the...

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Taking Turns

I stared at the wall, knowing I was next, listening to the dull thuds of the cane against Cameron’s diaper. Mistress would move to the thighs soon, she always did. But she liked to give a few thwacks of the dirty diaper first just to remind him of what he was wearing and therefore of his proper...

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More Captions! More Content!

As I grapple more and more with my new life and try to navigate its twists and turns, I know I have an obligation to all of you that have supported me along the way.

While I may not be able to churn out as many stories as usual, I am going to start exclusively posting captions to this site,...

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The Belt

I love strapping the belt across their tummy. It doesn’t really do anything. It’s not like they’re going to roll off the changing table. They could easily unstrap it as their hands are free, but they know not to unless they want a very different type of belt.

Instead, it just...

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DREAMS Daycare - Chapter 4

“Silly sissy!!” Casey reprimanded, smacking Peter’s wrist. It wasn’t hard, it hurt his pride more than anything, but it certainly sent the Crayon in his hand across the room. “You don’t color with that hand! You use the other one, remember?”

Annoyed, Peter rolled his ...

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Soak it in

“What are you doing?” I asked.

Her lip crooked into a devious smile as she rubbed the generous glob of lotion back and forth into her hands. Slick. Slick. Slick. “I’m going to give you the best handjob of your life.”

I blinked in disbelief.

She said it so firm...

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Roomies - Chapter 6

One Week Earlier

“I think you should start cleaning up around here.” Max said.

“Huh?” I muttered, barely looking up from my computer.

“Well, if you want to earn rent you’re gonna have to do more than just…suck my dick.”

“Aww but you seem ...

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Where the Fuck is Andre?! (Custom)

I was concerned!

I mean, who wouldn’t be if they hadn’t heard from one of their best friends in over a week? So after 8 days of radio silence, I decided I needed to pay Andre a visit. Who knows what’s happened to him. Did he have a random stroke at 34? Was he suicidal and I j...

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Switch - Chapter 2

“Get down on the fucking floor.” She snarled after another slap to my face. Immediately I dropped into bitch mode. The waves of submission coursing through my veins. I was trembling, not in fear, but in giddy excitement. I trust her more than anything, and she knows my limits more than anyone...

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Changes

(This is a custom caption continuation of "Bouncy Bouncy". Artwork credit goes to @Allezkook)

“Come sit down, little one.” Alyssa said to Eric after she helped him out of the bouncer. He’d made quite the mess from squishing around in his dirty diaper while Alyssa and ...

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Say It With Your Cheeks (Custom Caption)

“Bend over, bitch. Lift that fucking skirt and show me what I made your wife write on that dumbass diaper.” Marcus ordered.

“Y-yes Master.” The prissy sissy squeaked in that pathetic little voice Marcus makes him use.

Jeremy could hear Marcus and his wife cackling with laughte...

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Am I trying to do too much?

I've had a few people tell me that my quality of work has gone down, and that's a hard criticism to take. I really have been trying to put out the best stuff I possibly can. I understand my home life has been getting in the way of things a bit, but I really put a lot of effort into Roomies and Wh...

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Stairway to Hell

Jesse knew he should have found a new apartment complex after he and Lauren broke up. Few would advise staying in the same building as your ex, but the place was affordable and it was  close to work.

Luckily, he’d managed to avoid bumping into her despite several months of living in ...

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