Diapered Phone Sex - Diaper Sissy

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 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 […]

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, […]

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 […]

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

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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, […]

April 9, 2019

Published by Diaper Sissy at April 9, 2019

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Mommy’s Leaky Sissy

My naughty little diaper sissy just cannot get the hang of potty training! I’ve tried spankings, teasing, humiliation, and even the promise of some sissy phone sex with Mommy but nothing has worked to make her control her leaky ways. It is totally embarrassing for her when I dress her up in a big dirty diaper and take her out to see my domme friends. She whines and whimpers about how she can be a big girl this time and that she doesn’t need her princess diapers but we both […]

January 27, 2019

he is an adult baby sissy diaper boy; please humiliate him.

Published by Diaper Sissy at January 27, 2019

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Forever A Silly Sissy Baby

You will always be a diapered sissy baby. Everything that you wear will be lacy, frilly, super feminine and girly and sissified! You did try for awhile, and I know you wanted it to work, but there never was a chance that you could do it. So don’t feel ashamed about this, dear, it’s just your nature. There’s no fighting who you are, so you need to embrace it! Though you should always be horribly embarrassed with how your tiny sissy clittie always stays hard inside your diapers. I do […]

December 25, 2018

He wears pink clothing and the Swedish Diaper.

Published by Diaper Sissy at December 25, 2018

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Diaper Check for a Cuckold Husband

Do I smell something stinky? You went poopy in your diaper already, little diaper sissy? Well, shuffle yourself over here to I can give you a diaper check, see if that horrible smell really is you. I don’t care that my new boyfriend is here, I already told him about how you were my husband before, but you were horrible at it, so I had no choice but to turn you into my diapered sissy baby! So you are going to walk on over here, get your diaper checked, and […]