diapered sissy - Diaper Sissy

May 16, 2021

The yellow frill gown-clad Sissy With Diaper lady is standing in the garden.

Published by Diaper Sissy at May 16, 2021

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Aunt Brenda’s Diaper Sissy Training Starts! (part 1)

Brenda listened to a car door slam in the driveway, and nearly squirmed in excitement but simply crossed her legs, determined that Ethan would see only what she wanted him to see. He would see that she was in control of him, of the situation that she placed him; he wouldn’t know just how wet her panties were, not until she decided to let him know. The front door opened, and she knew the second he saw the pink sissy dress she had hung off the coat hook for him, […]

November 29, 2020

Standing on the ground in a frill baby gown and donning a white stocking and diaper

Published by Diaper Sissy at November 29, 2020

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Naughty Sissy Baby Humiliation

Sissy Baby Tammie shook and cried while Mommy and her friends laughed and teased her, talking about what a stinky baby she was. It wasn’t her fault! She had been just a little cranky earlier (she may have talked back to Mommy, but it wasn’t that bad), and Mommy started being so mean! She wasn’t even told before why she was pulled down onto Mommy’s lap, never even saw the thermometer, but she sure felt it when Mommy slipped in it her bottom while she was laying over Mommy’s lap […]

September 21, 2020

A pretend adult girl is posing for the camera while donning pink shocks and a stocking.

Published by Diaper Sissy at September 21, 2020

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Turned Into Silly Sissy Baby!

Leonard walked out his front door for the grocery store, his belly full of coffee and some tasty banana nut bread that his neighbor Brenda had brought over to him the other day, saying that it would make him an excellent light breakfast. He thought it was a little odd, considering that they had gotten into a pretty heated argument just a few days ago, but she apologized so he supposed everything was back to normal now. He saw her blinds twitch a bit but paid little attention to it […]

July 18, 2020

A Pink Butt man is posing for shots while standing on the ground and donning the pink attire.

Published by Diaper Sissy at July 18, 2020

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Forced To Be A Sissy Baby

You really should try to remember to wipe your browser history on a more regular basis, dear. At least when you have been looking up things that you might not want me to find, anyway. I’m sure you didn’t want me to find out that you’ve been searching terms like ‘diaper humiliation’, ‘sissy baby’, and ‘forced sissification’. I personally thing this is one of those situations where fantasy is a whole lot more fun than reality, but I’m willing to give it a shot for you, whether you actually want […]

June 14, 2020

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

Published by Diaper Sissy at June 14, 2020

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Plastic Lovin’ Little Sissy!

I’ve got one caller, sweet Sissy Baby Judy, that absolutely loves plastic anything when it comes time to dress up. I mean it when I say anything. Everything from the plastic baby bonnet on top of her head to the plastic baby booties. Dresses, elbow length gloves, baby mittens, and definitely can’t forget the plastic diaper covers! The crinklier they are the better they are as far as Judy is concerned. And I have to say that I agree, I love being able to hear her coming down the hallway, […]

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

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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 […]

January 31, 2020

A Diaper Sissy is posing for pictures while seated on the crib and dressed in a violet costume.

Published by Diaper Sissy at January 31, 2020

Sissy Princess Pottypants Gets Fussy

ohnny wanted to get up, wanted to spring out of the crib Aunt Brenda just placed him in and yell at her, tell her that she couldn’t tell him what to do! He really wanted to tell her that she couldn’t turn him into a sissy baby and call him Princess PottyPants… but last time he tried that all he got for his trouble was being put over her lap to get a spanking that still had his bottom sore from two days ago. He couldn’t believe that all this […]

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, […]

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 […]