Sissy Boy Phonesex - Diaper Sissy

March 26, 2026

Published by Diaper Sissy at March 26, 2026

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Sissy Training

Sissy Diaper training Alone: Naughty sissy doesn’t finish her assignments

Hiii, my sweet sissy sisters and diapered darlings! Oh my goodness, I just had to sit down in my fluffy pink diaper, the one with the little unicorns and extra thick padding that makes me waddle so cutely, and tell you what happened to me today. I’m still blushing and squirming just thinking about it! Mommy gave me my special weekend assignment list before she left for the day. You know the kind, those yummy rules that make my tiny clitty tingle just reading and hearing them from mommy. “Lacey, […]

March 19, 2026

a diapered sissy goes to the store with mommy

Published by Diaper Sissy at March 19, 2026

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Sissy Training

Sissy diaper training, sissy mommy takes me shopping

I woke up in my crib wearing the cutest baby pink satin dress Mommy picked out. It’s all poofy layers of chiffon and tulle that swish and rustle every time I toddle, with tiny white lace hearts sewn along the hem like they’re giggling at me. Underneath? My thick, crinkly diaper, the kind with the little teddy bears on the front so everyone knows I’m a little sissy baby, and the frilliest pair of panties ever, pure white with rows of baby pink ruffles that peek out no matter how […]

March 13, 2026

sissy shows off her training to mommy and her friends

Published by Diaper Sissy at March 13, 2026

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Sissy Training

Sissy showing off training

It started with Mommy calling me into the living room, her voice like warm honey. “Come here, my precious rose bud,” she cooed, and I waddled over in my fluffy pink dress, the one with layers of lace that swish swish against my thighs. The fabric is so silky, hugging my curves in all the right places, making me feel like a dainty doll ready for tea time. Underneath, my lacy panties peeked out just a bit, all frilly and white with tiny rosebuds embroidered on them, but today Mommy […]

March 6, 2026

Published by Diaper Sissy at March 6, 2026

Categories

Sissy Training

Diaper Sissy training tasks

Hello my sweet sissy baby sisters and fellow diapered ones It’s me, your shy little Sissy Baby Rosie, coming to you straight from my frilly play corner with a heart full of sparkles and a very crinkly bottom. Today I want to share the softest, most amazing day I had following Mommy’s special tasks she gave me. She never scolds or hurries me, she’s always so gentle, like she’s tucking a tiny doll into bed. Even when I’m all by myself, her words make me feel safe and small, and […]

July 25, 2021

Near the wall, a Diaper Man is standing and sporting a white baby girl suit.

Published by Diaper Sissy at July 25, 2021

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Abdl Retreat For Abdl Training!

My current boyfriend, Greg, isn’t really boyfriend material, so I’ve decided to go out and get myself a new one, someone that better fits the mold of a grown man. Greg definitely doesn’t do that! Between his small dick and his natural submissiveness, he’s more of a sissy baby than a real man. I don’t want to just drop him, though, it’s not like the poor thing can help it. Also, I would feel bad for the next female that he’s able to lure in through pity and lies. Best […]

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 22, 2019

Colored diapers White is more attractive and usable.

Published by Diaper Sissy at September 22, 2019

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Naughty, Messy Sissy!

Diaper sissy Amanda was crying harder than she ever had before; fat, round tears streaming down her face as she fussed in her diapers. “Mommmm-yyy pwease change meee!” She whined and whimpered between body wracking sobs, her sissy diapers stretched to gargantuan proportions behind her. “Aww, what’s the matter, baby wetsy pants?” Her hypnosis mommy mistress mocked her, tugging at the back of the over filled diaper stack. “Don’t you remember your sissy rules, princess?” The pathetic sissy baby struggled to choke back her tears long enough to gulp […]

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 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 […]