Mommies - Diaper Sissy

January 3, 2016

A Boob Sex with a Nude Lady the lady was nude.

Published by Diaper Sissy at January 3, 2016

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Leave Naughty in 2015

As sweet as I am, it just breaks my heart to have to dish out punishment to even the naughtiest of adult babies. And let me tell you… some of them are SO naughty! I sat down with them after the new year and had a long talk about leaving all of that bad behavior behind us as we move forward together! Most of them reacted like the little sweeties that they are. All of my diaper sissies smiled and nodded, promising to be good! As much as mommy loves […]

December 3, 2015

This photograph depicts Pioneer Park in San Diego, California, which is a lovely park.

Published by Diaper Sissy at December 3, 2015

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I love taking my little sissy to the park and showing her off to all the other Mommies. They’re always so jealous of me because my little sissy is so pretty and well behaved and obedient. They know that I could ask my sissy to do absolutely anything and she would do it right away. One of the mommies didn’t believe me though, so I decided to show her. I told my little sissy to get down on her knees and open her mouth. I told the other mommy she […]

September 13, 2015

Boy Sissy Sex The boy was dressed in a sissy outfit with high-heeled slippers and tights.

Published by Diaper Sissy at September 13, 2015

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Pretty Little Diaper Sissy

I am a loving, nurturing MILF. I do not like to have to repeat myself or raise my voice. Unless in a sexy role play, my typical demeanor is one that commands obedience and a submissive attitude. The perfect little sissy would know their place and acknowledge my full dominance over every aspect of their life without me ever having to utter a word. That is a tell-tale sign of a perfectly trained sissy slut. When mommy comes home from a long day and is tired, do you think she […]

September 6, 2015

Wearing a pink dress, a fetishistic back girl flashes her bare butt.

Published by Diaper Sissy at September 6, 2015

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Be Mommy’s Perfect Sissy

It is so nice when I have a good little submissive to play with however I see fit. When they do not talk back or fight the things I say, I am one happy MILF. I have a big, lonely house. One thing I have been wanting to get into the house lately is a pretty little sissy girl to do everything I say without giving me any lip! I have all sorts of plans for her, mainly letting her know that no matter what, mommy is in charge! When […]

August 25, 2015

Published by Diaper Sissy at August 25, 2015

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Sissified by Mommy Barb

Turning a naughty adult baby into a sissy girl does not always have to be done with domination as the motivation for them to be submissive to the idea. In fact, as my own mother always used to tell me, “you catch more flies with honey”. When you are sweet as pie, the babies often are sweet right back for you, making you taking care of them become much easier. I do my best to practice that method most of the time! I love getting to fill their nursery with […]

August 23, 2015

Published by Diaper Sissy at August 23, 2015

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Taboo MILF Phone Sex

Something that I have been coming across more and more often is cuckolding. Men seem to absolutely go crazy for the idea of their wife, girlfriend, or other intimate partner taking advantage of them and fucking other men. One thing they really love is when their woman takes their affair right before their partner’s very eyes… They seem to just absolutely love the thrill of seeing this other man fucking his wife right in front of him. Things can get heated and take an even sexier turn when we bring […]

August 3, 2015

In this picture, there is a t-shirt with the words "little cocks make me laugh" printed on it. The t-shirt is purple.

Published by Diaper Sissy at August 3, 2015

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Small Dick Humiliation – My Specialty

I am a strict mommy that trains naughty boys and loves small dick humiliation phone sex. Just look down between your legs, you know who you are. I am a perfect mommy to use you and make you feel pathetic. I will measure that useless penis of yours in front of my lady friends and we will all laugh at you. I will show you what you are good for, to use your eager tongue to become my ass whore and pussy slave. You really must understand that a tiny […]

July 30, 2015

A Nude Ava Lady is posing for the photographs while sporting a stunning black attire.

Published by Diaper Sissy at July 30, 2015

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Mommy for Diaper Girl

I have so many wonderful sissy boys in my nursery and I just love getting to play with them. I think it would be fun to have some time playing with a sweet diaper girl. She can join us while we play dress up and with all the toys I have for us. I can buy new outfits for my adult babies, the pair of them will look so pretty in their dresses and adult baby diapers! I would hold them to my chest and have them each latch onto […]

July 23, 2015

Published by Diaper Sissy at July 23, 2015

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Adult Baby Diapers from Mommy

My ABDLs love their nice cozy adult baby diapers. I have so many stacks of cute diapers for you in the nursery I made just so you could be safe and have fun with me. I would love to spend some quality time playing dress up and dollies with a sissy boy. Maybe you just need someone to love on you while you suck on some big tits and take in the warm milk to fill you up when you’re hungry. Your crib and changing table are all ready for […]