sissies - Diaper Sissy

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 […]

November 5, 2015

A Mmmys Boy Adult Caption this is caption is relevant to adult users. And this is mature words.

Published by Diaper Sissy at November 5, 2015

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Obedient Sissy

My sissy and I went shopping earlier, and we got a lot of cute skirts for him to wear. I let him sit down on the bus ride home, with our bags at his feet, and I stood in front of him. The bus was very crowded, and there was a man behind me staring at my ass the whole time. I glanced back for a moment and saw him rubbing himself through his jeans. I got a very wicked idea and told him my sissy would gladly take care […]

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 […]

November 1, 2015

A Sweet and Seductive Lady The woman was just partially clothed. And she has the appearance of a candy doll.

Published by Diaper Sissy at November 1, 2015

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Sissy Whorehouse Halloween

Oh man did I have the best halloween ever. There’s never a bad time to add humiliation phone sex to your holidays! This year I got to dress up my little sissy sluts and boy did we have some fun. Instead of a little haunted house we decided to turn our garage into a little Halloween sissy whore house. Instead of passing out candy we passed out blowjobs! My little sissy sluts all stood in a line on their knees as one guy after the other started coming up and […]

October 29, 2015

The lady had a pair of sexy bosoms and was dressed in a western attire.

Published by Diaper Sissy at October 29, 2015

Strap On Training

I think it’s about time for some good ol fashioned pegging phone sex. You lubing up that ass for me you little pegging slut? Mmm I’m going to stand behind that little ass of yours and put on my nice thick strap on. It’s the big black one just like you like it. I’m going to rub my big mushroom head all over that little puckered hole of yours. Are you ready for my cock? This is your training you little slut. You need to learn how to take my […]

October 27, 2015

A Sissy Barbie Girl the lady was dressed in an extremely deluxe version of a traditional white southern belle attire.

Published by Diaper Sissy at October 27, 2015

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Halloween for Sissies

It’s that time of the year! That enchanting smell that comes with fall weather, pumpkin spice lattes, and Halloween. What better opportunity is there for a sissy to go out on the town in the frilliest of gowns? Imagine how much fun you can have just preparing for the event. Going to the store and finding a Barbie pink dress with a full skirt so that you can wear a diaper underneath with no one the wiser. A trip to the makeup counter for a bright lipstick to match. After […]

October 27, 2015

a pair of sissy pants in pink and white The lady was dressed in a frilly sissy panty that was pink and white in color and did not have any designs on it.

Published by Diaper Sissy at October 27, 2015

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Dressing Up My Little Baby

My little boy is so much better as a sissy in a dress. Brian turns into Briana like magic when I slip him into a lacy skirt and top. Briana squeals with delight at anything pink and loves to play with mommy’s makeup. I see how Briana looks enviously at my painted nails, but I can’t let her use my nail polish on her own fingers like she wants- she would make such a mess! My makeup is fine though. She’s darling with a bit of barbie pink lipstick on […]

October 26, 2015

Back to school time is a special occasion for everyone. Back to school is still written on the blackboard in the image.

Published by Diaper Sissy at October 26, 2015

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A Fun Weekend with Mommy

Just this weekend, I finally followed through and taught my son how to suck his daddy’s thick cock so that he can be a good little sissy slut. First, I told him his daddy likes his girls to be very pretty, and that if he wanted to be like mommy, he would have to be very pretty too. I had him strip down and put on a pair of lacy, black panties and a pretty bralette. My baby boy’s pretty clitty is so little it fits nicely into the panties, […]

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 […]