wittlesissybaby

Season's Greetings

“How’s your diaper? Is it nice and wet yet?”

Drew kept tugging on his ruffled skirt, but no matter how much he tried, he couldn’t get it to cover the poofy pampers underneath.

Penny smirked as she leaned over to peek at the indicator line. “Well it’s nice and blue, but the...

Baby's First Step (Custom Caption)

“Hi sweetheart, why don’t you sit down for a second? Now that we’re back from our Honeymoon, I think it’s time we have a chat about how things are going to go around here from now on…

As you know, I have this incessant need for control. I know you like it when I tell you things to...

Damp Pamps

They say when potty training, it’s best to put their undies inside the diaper. That way, when they pee, they can feel the wetness more before it gets absorbed by the padding. The revolting feeling helps program them to want to use the potty.

I took that to heart.

Billy came to me a ...

Daddy Keeps Me Docile

“Someone's being much more docile today. Did your little talk with Daddy earlier help? Hmm? Sounded like somewon was getting quite the spankies in there. Is that why your bum bum is so red? Awww!! Don’t worry baby, Mommy’s got a cream for that.

You keep trying to say you’...

Vote for a Cover Photo of "Damp Pamps"

I have a caption/short-story coming up about a submissive who has to wear undies underneath his diapers. The undies get soaked first, and then the diaper. I was having trouble finding a photo on the web to use, so I asked you guys for help, and boy did ya'll deliver!!

I expected to get 1 or...

Big Daddy

“Shit. Shit! SHIT!” Layla shrieked, bustling through the living room, then the kitchen, then the playroom. She tripped over one of my blocks, which only made her more frustrated.

“What’s wrong?” Rob asked, rushing in like there was a fire.

“I forgot to get a present for Ci...

Last Call for Panty Pissing Pics!

I'm going to try to do a poll with all the pictures on Thursday. So if you want to send a picture of you in wet undies under a diaper, send them in! Email them to wittlesissybaby@hotmail.com or message me with a drive link!

Love you all!!

Custom Caption For Emilie

I’m such an idiot. I shouldn’t have been so anxious, so impatient, so…horny.

Martine from work dropped by to get some notes on the project we’re working on. It was a relatively quick transaction. She’d set her purse down, accepted the glass of water I offered, gathered up the note...

December Updates

Hello everyone,

Just wanted to let you know what I have in store for you this Holiday season.

First off, I am continually trying to make this blog more active and interactive. I will never be able to post as much as I do on tumblr for a few reasons: my Patreon content requires a lot m...

What Sissy School House Would You Be In?

In celebration of the release of the new chapter of Sissy School, I'm curious, which House would you want to be sorted into?

Maidenlaw - for those who seek to serve in the home as a caretaker to their owners every need. They pride themselves on keeping a clean house, and a ...

Sissy School Chapter 9 - Moaning Mannie

Note: There is a trigger warning for this story, but it might be a spoiler. So if you need to see the warning, scroll to the bottom. Otherwise, enjoy :)

“It just doesn’t make any sense…” Henry said with a mouthful of toothpaste.

He seemed to handle ...

Picture Request, anyone want to help out?

I need a picture of a wet diaper. But not just any wet diaper, one that you had to wear with your 'big boy' or 'big girl' undies underneath.

You read that right.

I want you to have your undies on, and then your diaper over your undies. Both need to be soaked (but, obviously, ...

STUFFED

I never should have said it. I never should have said anything. It was so stupid. I didn’t even mean it. Or maybe I did? Whatever. Even if I thought it, it’s not something I should have said about someone close to me.

Amy and I had been friends since high school. We were in homeroom tog...

Ralfi's B-Day (Custom Caption)

Trigger Warning: The "F" slur is used. It's done in a vengeful sort of way, but I still wanted to put that out there. Enjoy!

Guess what today is, sissy! What...you don’t know? It’s your 2nd birthday, of course! Obviously you’re much older than that, but today marks 2 ...

Diaper Cuck - Part 2

*clap* *clap* *clap*

“Unnhh…unhhh…oooOOOhhh!! Yea!! Right there!!”

She was on her hands and knees now, driving her hips back into mine.

God damn she could take a dick. Usually I have to go slow or be careful not to penetrate so deep that it hits their c...

Diaper Cuck - Part 1

Trigger warnings: Lots of humiliation and degradation in this one. I removed the ‘F’ slur as it probably wasn’t necessary. I think the story is just fine without it. Hope you like it.

“Hi,” she said when I opened the door.

God damn she was looking f...

Sorry for the Lack of Content

I had quite a dip in subscribers recently and most of the exit surveys cited that I "don't post enough."

As some of you know, my Tumblr got taken down a few weeks ago, which kind of threw a wrench in my workflow. I've been hard at work trying to rebuild that blog and it's unfortunately suck...

How do you feel about me using the term 'faggot'?

Sometimes I think about using it as a way to demean sissy/cuckolds, but I don't want to offend or trigger anyone, let me know how you feel.

MAW

Daniel awoke with a jolt. His head was spinning. Was he hungover? How much did he even drink last night? Where did he drink last night? In his daze, he couldn’t remember the last few weeks, much less the last 24 hours.

He reached a hand up to his groggy forehead, tried to rub his...

Meet the Parents - Chapter 4

“Ow! Ow!”

“What?” Jan asked, applying cream to the rash and welts still present on Phil’s buttcheeks and thighs. “I’m hardly even touching you!”

“No no…it’s the cage…” Phil hissed in pain.

“Really? You’re getting hard just from this?” Jan laughed,...

My Tumblr got deleted...again.

Tumblr seems adamant to get me off of their site. Unfortunately it happens to be the easiest to use. I wish I could go to other things, but I have made so many friends and enjoy the community too much to let it go.

So, if you will, please go to 2022-10-16 17:58:28 +0000 UTC View Post

The Satin Sock (Part 2)

Simon gulped as the curtain opened. The bright lights bore into his eyes, the heat blazing into his cheeks, or was it just the blood rushing to them?

Miley Cyrus’ “BB Talk” started playing. The crowd went wild, but it did nothing to calm his nerves. If anything, it just emphasized how...

The Satin Sock (Part 1)

As soon as Claire stepped into the dorm room, the girls knew something wasn’t right.

“What’s wrong??” Kim asked as Kendall rushed to greet her.

The emotions Claire had bottled up on the drive back started spilling out. “Brad and I got in a really big fight…” she said thr...

The Check-Up

Author's Note: I was inspired to write this story after a doctor's visit I had a few weeks ago. Hope you like it :)

“Is this really necessary?” Stephen asked when Mallory pulled into the parking garage.

“Of course it is.” His wife explained, turning the wheel ...

Wanna know how to get me to continue stories you like?

Let me know that you like them! It's hard for me to gauge how you guys feel about the things I put out. Other than the polls, I don't really know if you're liking a particular story and want to see it continued. 

Messages/comments like this are really helpful to let me know not only th...

And the winner of the poll is...

Well...No one. Haha. Sissy School and Meet the Parents both tied for the top spot. So I am going to have to make an executive decision: because I most recently released a chapter for Sissy School, I will do a new chapter for Meet the Parents in October, and Sissy School in November. I still ...

New World Order - Chapters 1 & 2

Warning: This story, by its very nature, is going to piss people off. So if you’re someone that is easily offended, or tends to take works of fantasy/fiction seriously and get triggered, please don’t read it. None of the views expressed in this story are necessarily my own, I’ve jus...