Diapered Sissy - Diaper Sissy

December 6, 2015

A Sexy Girl is standing in the background for the photoshoot, wearing black lingerie drees.

Published by Diaper Sissy at December 6, 2015

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Diapered Sissy

Feminized By Mommy

Hi there sissy fags! I’m calling out to all the naughty little sissy phone sex lovers. Are you ready to be sissified like mommy? Maybe your girlfriend is at work and you’re feeling a little girly? Such a naughty sissy boy aren’t you. Pretty soon your girl friend is going to wonder where all her panties have gone! Poor thing. Has no idea that her boyfriend whos supposed to be man of the house is a panty wearing sissy boy. Which one of her panties are you going to try […]

November 22, 2015

A Nude Boob During the showing, the lady was completely naked. In addition, the panty she is wearing is white.

Published by Diaper Sissy at November 22, 2015

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Step mommy

This step mom role sure has its perks, I get to have all the young men hanging around our house and occasionally I even get to teach them a thing or two. They also like to have fetish parties which I have to say is a huge bonus. Since my husband travels so much for work, it keeps me from being lonely. We made sure to have all these arrangements in place before I ever even considered marriage. Oh it benefits him as well he has fun while he is […]

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 18, 2015

A Spanking Image Instructions for mature users are included in this image.

Published by Diaper Sissy at October 18, 2015

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Naughty Aby

I found out recently that my aby has been having sex before marriage. I decided to punish him for his naughty behavior, so I decided he deserved a taste of prostate milking. When he came home from work today, I ambushed him in his room. He was very surprised to see his sexy mommy naked except for a pair of thigh high boots and a strap-on. I locked his hands into a pair of handcuffs and pushed him onto his knees. I bent him over so he was on his forearms, […]

October 12, 2015

A girl is punishing her boyfriend, and a man apologises to her, and the girl is using sexy products.

Published by Diaper Sissy at October 12, 2015

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Naughty Diaper Sissy

My sissy baby likes to pee while I change him. As soon as I take off his soiled diapers, he pisses from his little sissy clitty, and I am tired of it. Today, I showed him what it felt like. I took off his diaper earlier, and when he started to pee, I grabbed his pee-pee and angled it up, so his piss sprayed all over his chest and face. He was very surprised, but not as surprised as he was when I took him off the changing table and […]

October 9, 2015

A Hot Lady The woman was dressed in a pink western attire.

Published by Diaper Sissy at October 9, 2015

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Canadian Thanksgiving

Do you know what this Monday is? It is Canadian Thanksgiving. And since mommy Susan is Canadian what better way to spend the day with my little sissy then to have a wonderful turkey dinner. You will wear your new sissy dress mommy bought for you. The one with the pink bows. And your new wig as well. I love how long and brown it is. My family can’t wait to meet you. I have told everyone about my little tiny cocked sissy. I may even let uncle Marv spend […]

October 3, 2015

Published by Diaper Sissy at October 3, 2015

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Diapered Sissy

Sissy

Diaper Sissy weak and Frail, Hanging off her mommy’s tail. ABDL in fancy dress, not allowed to make a mess. Hands and knees mouth open wide, fills her mommy with so much pride. Takes a cock so big and thick, while stroking on her tiny dick. Bent over my leather couch, take the cock but don’t say ouch. Diaper sissy tries to cry, Mommy says don’t even try. Friends of mommy cum to play, Sissy says no go away. Sissy tied up nice and tight, Sissy try to escape and […]

October 1, 2015

A Magnificent Dress by a Renowned Designer It was a very pleasant sight to behold, and the dress was looking so lovely.

Published by Diaper Sissy at October 1, 2015

Training My Sissy

I’ve got something special planned for you tonight, so why don’t you start by coming over here and sitting on the bed? I’m going to make you feel like such a pretty girl tonight, and you’re going to love me being your Mistress. It’s time to start the feminization process of your Sissy training; and I want to begin with getting you into these cute little panties and matching bra! So pull off your clothes.. and hurry up, or you’re going to get a hard spanking. Once you’re completely naked, I’m going […]