cuckolding - Diaper Sissy

February 28, 2021

There is a Diapered Cuckold adult poster with a man seated with a black coat.

Published by Diaper Sissy at February 28, 2021

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Be A Good Boy For Mommy

Mommy has plans for the night. So after your bath and fresh diaper, mommy will put your jammies on and tuck you in for the night. Mommy lays you in your crib in the abdl nursery. Now be a good boy for mommy and close your eyes. Muah! Sweet dreams little one, mommy will be back later. Mommy comes home with a man she met at the bar earlier in the evening. Mommy opens your door slightly, peeking into check on you before heading to her room across […]

June 17, 2017

Standing on the ground, a hot and seductive naked woman removes her clothing to reveal her nude boobs while sporting a black porn sex toy.

Published by Diaper Sissy at June 17, 2017

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Cuckold Mommy Phone Sex

Calling all cuckold phone sex lovers. It’s the first of the month again. That means that rent will soon be due so I hope you plan on paying it because a hot fem dom like me shouldn’t ever have to lift a finger for anything. Besides I treated myself to some new heels so once again you’re going to have to do and suck every cock needed until we’ve finally payed it off. That mouth will be working in over drive while your little hole gets plowed. I just got […]

February 13, 2016

The woman was dressed in a western costume, like a Sexy Clamor Lady.

Published by Diaper Sissy at February 13, 2016

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Just Another Cuckold

Well what do we have here? Oh it’s a cuckold. What a shocker. Let me guess you’re sitting there right now with your hand between your legs tugging on that pathetic chode of yours. You’re probably thinking about how hot it would be if you were here with me right now watching in the corner as I get fucked by real men with big cocks who actually know how to use them. Yeah your little useless pecker can’t compare to the thick hard throbbing rods needed to fill up this […]

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 7, 2015

A Sissy Pegging woman can be seen standing in front of a man while she is pegging him while wearing the sex porn toy.

Published by Diaper Sissy at October 7, 2015

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Sissy Pegging Phone Sex

If you have any lube I suggest you use it now! I want you to bend over for me and spread em. It’s about time for some strap-on phone sex! Being a closet fag such as yourself, you don’t have many options as far as sissification training, so I’ve decided to take a step and be your guide. My strap on is going to open up that little ass of yours so that it’ll be taking all sizes of cock in no time! I’ll use my big black strap on […]

September 10, 2015

The woman was wading while in black stockings and had a naked sex. She is currently seated on the sofa.

Published by Diaper Sissy at September 10, 2015

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Small Penis Humiliation

Mommy is finally home from work and you know what that means! It’s time for mommy to have some fun with her abdl! We play lots of games together don’t we? Well today mommy is going to play her favorite! It’s called find the pee pee! That’s right you have a tiny little peeny weenie don’t you? Aww it looks so cute nestled between your legs. I bet mommy could find it if she started rubbing it like a little clitty huh? That’s exactly what it is! A little clitty […]

September 6, 2015

A Hot Girl is in a nude pose and she appears to be hot and sexy.

Published by Diaper Sissy at September 6, 2015

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Mommy’s Dirty Panties

Well what do we have here? I was just about to finish putting your laundry away like the caring mother I am. But then I got to your underwear drawer and I was in for a surprise. I moved some of your briefs to the side to make more room when the back of my hand brushed up against something silky. I closed my fingers around the fabric and low and behold there are my pink panties I wore last night. I’m certain this isn’t a mistake because I put […]

August 22, 2015

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

Published by Diaper Sissy at August 22, 2015

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Cuckold Sissy Hubby

I bet you think your dick is great… well its NOT! It’s a tiny, little pee pee, and you are a pathetic little cuckold bitch! I’ve eaten fries BIGGER than your puny little pecker. And I KNOW you touch it a lot. There you are diddling your dick in the corner, how PATHETIC!!! But what I can’t understand is how you find the fucking thing! What do you use for a jock strap? A thimble and some thread? Oh wait… you have to be a jock to use a jock […]