sissies - Diaper Sissy

June 7, 2020

For the photo session, a Diaper Sissy is positioned on the ground while standing.

Published by Diaper Sissy at June 7, 2020

Categories

You Need To Be Turned Into A Sissy Baby

It’s time to get you dressed to go out for the day, little sissy baby. I want you to be so sweet and adorable that all the other mommies will be green with envy! I’m thinking that a pink and white dress with the poofiest little hem is exactly what I want you in, right along with your diaper and a pair of sheer tights. Of course, the dress is short enough to show your diapered sissy bottom to anyone that takes the tiniest glance in your direction. Oh, and […]

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

Categories

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

Categories

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

Categories

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 […]

June 30, 2019

Stepmother wearing pantyhose while waiting for dig Bick boy

Published by Diaper Sissy at June 30, 2019

Categories

Showing Off Sissy

“Come on out, dear!” You can hear her calling you from the living room, followed by a bunch of excited giggles from her friends. Running your hands down the front of your short, pleated skirt you wonder how much more of this sissy humiliation you can stand. Here you are, dressed in an adult baby diaper, plastic pants, and oh so short pink skirt and matching blouse, about to walk down the hall and present yourself to your sadistic girlfriend (now your Mommy!) and her attractive female friends, the kind […]

June 15, 2019

He rubbed his thighs together as Mommy Tawny approached

Published by Diaper Sissy at June 15, 2019

Sissy Fucked in Diaper

Andrew rubbed his thighs together, barely hearing the crinkle from his plastic backed abdl diapers as he squirmed on the bed laid out on his back, watching Mommy Tawny walk towards him. Her strap-on was swaying in front of her, and he didn’t even try to look away, the thought of how good that dildo was going to feel inside him made his sissy pussy clench down on the plug inside it in eagerness. It felt so good that a needy moan slipped past his lips and his hips rocked […]

April 25, 2019

She felt warmth on the inner of her thigh and precum dribble down her clottier.

Published by Diaper Sissy at April 25, 2019

Sissy Babies Should Be Embarassed!

Judy couldn’t stop the blush popping up across her face and neck, her skin burning with humiliation as she listened to the clicks that came from between her legs as Aunt Brenda took pictures of her plastic adult diaper covers with her camera app. She squirmed a little bit, her tights rubbing against her legs, her eyes clinching tight while Aunt Brenda laughed at her! She couldn’t hold back a squeal when a hand smacked against her thigh, and she was told to stop moving…. She barely managed, but all […]

March 24, 2019

solid black leather on one side & red padded garment leather on the other side

Published by Diaper Sissy at March 24, 2019

Categories

Sissy Spanking Needed!

You have misbehaved and been a naughty diaper sissy, haven’t you? Running around, flirting with all the men, flipping your skirt up around them like a little cock tease! That is simply not acceptable, and you know that you are going to be punished for your behavior. Go ahead and kneel next to the bed, resting your arms across it to get in position for your well-deserved paddle spanking. You will count out loud every time I bring the paddle down on your bottom and at the end of your […]