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February 20, 2026

Published by Diaper Sissy at February 20, 2026

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New Year New Rules for Mommy’s 2026 Sissy Training

Well here we are in 2026 and Mommy has been busy putting together some new rules for all her sissy babies. If you thought last year was intense, you haven’t seen anything yet. The mommies at Diaper Sissy have been talking and planning and let’s just say there are some exciting changes coming to how we train our little ones. First up, we’re getting even more personal with our sessions. A few of our mommies have started keeping detailed notes on their regular callers. That means when you call back, […]

June 22, 2025

Published by Diaper Sissy at June 22, 2025

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Mommy’s Assignments After Our Phone Call Together

One thing a lot of new callers don’t realize is that the fun doesn’t have to stop when you hang up the phone. Some of our best mommies love giving assignments that keep you in sissy mode long after the call ends. And trust me, they will follow up to make sure you did what you were told. The assignments vary depending on your mommy and what kind of session you had. Maybe she tells you to stay in your diaper for the rest of the evening. Maybe she wants […]

January 15, 2025

Published by Diaper Sissy at January 15, 2025

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Mommy’s Humiliation Playground Where Sissies Learn Their Place

There’s something about picking up the phone and hearing that nervous little voice on the other end that just makes my whole day. You know exactly what I’m talking about if you’ve ever called one of our mommies here at Diaper Sissy. That moment when you finally admit what you really want and Mommy starts laying down the rules? Pure magic. Our humiliation playground is where real transformation happens. It’s not just about being told to put on your diapers and frilly panties, though that’s definitely part of the fun. […]

December 26, 2019

Standing on the ground wearing the white diaper is a feisty grandmother.

Published by Diaper Sissy at December 26, 2019

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Sissy Baby Turned Into Sissy Puppy!

Michael eased down on all fours, leaning forward so that his bottom lifted up into the air, his sissy dress falling down a bit to his waist. He started to lap at the dog bowl full of baby formula that Auntie Brenda had put down for him, licking it clean, then switching over to doggie bowl with pureed baby food right next to it and gave that one the same treatment. He had been a naughty sissy baby, and his auntie decided that some humiliation punishment would be just want […]

December 1, 2019

She is wearing a white diaper and a Sissy Faggot diaper man is seated on the bed.

Published by Diaper Sissy at December 1, 2019

Cock Lovin’ Sissy Faggot

I am always surprised with just how many diapered sissy faggots there are. Most of them walk around all day fooling people, having them convinced that they’re regular men, instead of cum hungry little faggots that love to get fucked in their diapers! They even try to fool themselves for a little while, but those thoughts of thick cocks, thicker diapers, and getting fucked properly are never too far from the front of their minds. They love the humiliation of being dressed in pretty feminine things with a diaper underneath, […]

October 6, 2019

The man is sitting on a chair and wearing a lock, and there is a pink Sissy Chastity sex toy nearby.

Published by Diaper Sissy at October 6, 2019

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Sissy Locked in Chastity

All too often, a sissy will come my way with a grave misconception about just what they are permitted to do and what they are forbidden from doing. Too many sissies will assume that just because they may have been behaving lately, that they are allowed to take it upon themselves to decide to start playing with that little peepee. Sorry, sweeties! Wrong! That pathetic little thing belongs in one place and one place only: locked up tight in chastity! That look of disbelief and humiliation on their face when […]

September 5, 2019

She's approaching the car with a diaper and pink sissy dress.

Published by Diaper Sissy at September 5, 2019

What Type Humiliation Is Your Favorite?

I certainly know that for quite a few sissy babies getting humiliated can be a highly sexual experience for them, and there is not a thing wrong with that. It can be a lot of fun for me to tease, let me tell you! But for others, it’s never sexualized. Whatever embarrassing and mortifying things the sissy is told to wear or do, it’s solely about the humiliation and shame that comes along due to those actions. Sometimes it’s done publicly, other times in private, but either way the sissy […]

July 17, 2019

The white diaper-wearing Dildo fetish man is resting on the ground.

Published by Diaper Sissy at July 17, 2019

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Naughty Sissy Baby Fun

Sissy Baby Penelope wiggled back on her knees a little bit more, giving herself another inch or two to rock back on the suction dildo attached to the back of her crib. Her pussy was extra tight since her abdl diapers were down around her thighs so she couldn’t spread her legs out wider and that extra bit sliding deep inside, filling her pussy up even more drew a filthy moan from her mouth. She heard Auntie Brenda giggling a bit from where she was sitting in the nursery rocker, […]

July 5, 2019

There is neither a ruffle nor a diaper sissy on the light pink ruffled panties.

Published by Diaper Sissy at July 5, 2019

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My Sissy Baby Girl!

I have a pretty pink dress, a lace bonnet with a wide ribbon to tie underneath your cute chin, a pair of shiny white leather buckle shoes, lacy anklet socks, some ruffled pink diaper covers, and of course, a pink princess diaper. It’s all for you! You, silly thing, are going to be by sweet sissy baby girl and that means that around the house you don’t wear a thing that is cute as a button. Some days I might want you to waddle and crawl around, a pacifier in […]