November 6, 2015
In Mommy's Slutty Outfit, a woman is shown walking along the street while sporting a miniskirt.
Published by Diaper Sissy at November 6, 2015
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Mommy’s Sexy Clothes

Your fetish for slutty clothing started at a young age and you know exactly what started it all. Your mother was always strutting around in tight skirts, low-cut tops, and high heels. Your friend’s parents would comment that the way she dressed made her look like a whore but you always thought she was the prettiest woman you’ve ever seen. Imitation is the sincerest form of flattery, isn’t it? So you think she would be happy to see how hot you look when you wear the same type of clothing […]
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November 1, 2015
A Domination of Role Playing The thoughts on the wall are all black in colour.
Published by Diaper Sissy at November 1, 2015
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Bend Over for Mommy

You know what always makes mommy soooo happy? I think you might have an idea of what inside that naughty little mind of yours.. When mommy has had such a long and stressful day, nothing would be enjoyed more than coming home to see an obedient and willing little sissy on their hands and knees on the bed, bent over and waiting for mommy to come stuff a big strap-on deep into your ass. I can see you look back at me from where you kneel. You look so submissive […]
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October 25, 2015
A girl's gown is shown in the image, and it is very pretty in light pink.
Published by Diaper Sissy at October 25, 2015
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Perfect Sissy Boy

I got the chance to play with the most well behaved little sissy boy the other day! He told me that he just loved to be put in adult baby diapers. They got him so excited! Well knowing that, I made it my personal mission to have him make a big mess of a certain sort in his diaper for me. He listened to everything I said, and when I had him lay across my lap and give him a few hard spankings just because I can, he could hardly […]
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October 15, 2015
A Hot Lady The woman was dressed in a pink western attire.
Published by Diaper Sissy at October 15, 2015
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Dirty Diary

Hello Eric, your mommy had to go away for the day so I am going to watch you. My name is Mr. Zuni, but you will call me daddy. Your mommy trusts me to watch you so you will not tell her anything that happens today, you can write about it in your dirty diary I want to be able to watch you all the time. I love how you look in that sissy outfit. It’s so short I can see everything when you bend over. Those panties look so […]
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October 11, 2015
Boy is laying in bed while attractive girl is dressed in Penis sexy material.
Published by Diaper Sissy at October 11, 2015
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Smelling Stinky Diapers

You are usually a very obedient and well behaved adult baby. Sometimes though, you make huge stinky messes in your adult baby diapers! That is not the problem, of course. I am a mommy and am always well prepared to get you out of that messy diaper and into a fresh and clean one at a moment’s notice! The real problem lies in the fact that you have figured out how to put off me finding out by not squirming around when you mess in them, and even making sure […]
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October 4, 2015
The boy was dressed in a pink sissy adult dress, high-heeled slippers, and stocks.
Published by Diaper Sissy at October 4, 2015
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Sissy Slut

It is always so funny to me when little sissies try to deny that that is what they are. They will try so hard to convince me and other beautiful MILFs that they are men! Can you believe that? With their tiny little cocks, all they deserve is to have it hidden away from the rest of the world in a thick adult baby diaper. They come to realize and accept it once I have done my motherly duties and told them what is best for them. Eventually they come […]
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September 27, 2015
A Nude Breast Nipple lady is sitting on the bed, showing off her nude boobs while wearing a sexy porn toy. The man is also nudely lying on the bed.
Published by Diaper Sissy at September 27, 2015
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Seductress Mommy Candy

I am 36 and what I love best is seducing a man much younger than me. You will grow to love everything there is about fantasy milf phone sex. It’s one of the hottest experiences you’ll ever have! I love stealing the virginity of a young boy because virgins are so cute and very eager to please! My neighbor has a gardener who just turned 18 so I told her I needed some yard work done. I just wanted to have him all to myself. When he came over I […]
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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 […]
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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 […]
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