Humiliation - Diaper Sissy

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 26, 2019

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

Published by Diaper Sissy at December 26, 2019

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 […]

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 […]

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 […]

February 3, 2017

A Spanking Phone Sex: she was naked and wearing a pink hair band ribbon.

Published by Diaper Sissy at February 3, 2017

Ty loves sissy fag phone sex pt 2

Here’s the rest of the email my sissification phone sex lover Ty sent me. Check for part one here Then, at the ceremony, I would be taken to the altar, and have to say my vows, that I was a sissy, and that mark was a real man, that I would always call him DADDY or Master, that I would promise to obey him always, clean and cook and bathe him, and that he could do anything with me. I would have to go to the bondage store and buy […]

October 7, 2015

A Sissy Pegging woman can be seen standing in front of a man while she is pegging him while wearing the sex porn toy.

Published by Diaper Sissy at October 7, 2015

Sissy Pegging Phone Sex

If you have any lube I suggest you use it now! I want you to bend over for me and spread em. It’s about time for some strap-on phone sex! Being a closet fag such as yourself, you don’t have many options as far as sissification training, so I’ve decided to take a step and be your guide. My strap on is going to open up that little ass of yours so that it’ll be taking all sizes of cock in no time! I’ll use my big black strap on […]

October 1, 2015

A Magnificent Dress by a Renowned Designer It was a very pleasant sight to behold, and the dress was looking so lovely.

Published by Diaper Sissy at October 1, 2015

Training My Sissy

I’ve got something special planned for you tonight, so why don’t you start by coming over here and sitting on the bed? I’m going to make you feel like such a pretty girl tonight, and you’re going to love me being your Mistress. It’s time to start the feminization process of your Sissy training; and I want to begin with getting you into these cute little panties and matching bra! So pull off your clothes.. and hurry up, or you’re going to get a hard spanking. Once you’re completely naked, I’m going […]

September 11, 2015

The boy was dressed in a pink sissy adult dress, high-heeled slippers, and stocks.

Published by Diaper Sissy at September 11, 2015

Teacher Takes Control

It was a normal day for me; I was in my classroom and working on the last of my paperwork when one of my students knocked on the door. I waved him in and couldn’t help but laugh when he entered the room wearing a frilly pink dress. He slowly walked up to me and started fumbling through some excuse about how he had lost a bet but I knew better.. He was a sissy, and no doubt, he was sent here for the humiliation he would endure walking through […]