Age Play - 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, […]

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 […]

September 5, 2020

Male pornographer He was in his underwear and was standing on the ground next to another man.

Published by Diaper Sissy at September 5, 2020

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Sissy Slut Sierra

Sissy Slut Sierra, is the name that I gave to my neighbor’s husband. He had been coming around every time I had an issue with my house and he has always fixed it. It was by accident one day while he was bent over fixing a leak under my kitchen sink that I noticed a that he was wearing a silky pink panty with ruffles peeking up from his droopy jeans. Without warning I walked behind him and placed my hand in his pants and tugged on the panty then […]

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 […]

October 7, 2019

Changing Boy Domination boy is wearing a white diaper and is lying on the bed.

Published by Diaper Sissy at October 7, 2019

Diaper Daddy’s New Cock Sucker (part 1)

Brandon felt his mouth stretch wide around his new Diaper Daddy’s cock and couldn’t do a thing to stop a low moan from vibrating through his throat, making Daddy chuckle and grind his hips against Brandon’s face. Brandon wasn’t sure if he would have stayed away from his neighbor Brenda’s house if he’d known what was going to happen… or if he would have run over here. He had a party at his house last week and she must have taken a peek at his laptop. He hadn’t remembered about […]