Sissy Boy Phonesex - Diaper Sissy

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 25, 2015

The lady was dressed in a white western costume dress with panty, and she was showing off her ample assets.

Published by Diaper Sissy at October 25, 2015

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Sissy, Sissy

Well what have we here? A big whinny sissy boy! Do you really think that I will let you get away with this naughtiness? Bad behavior does not get rewarded! You will come over here right this minute. Stop that whining now. Where ever did you get that dildo from? Don’t try and pretend that I didn’t see you in the corner with your hand in your diaper, and playing with that big dildo. I saw it and now you will pay for it. Come here! Where did you get […]

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 […]

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 […]

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 […]

September 11, 2015

The boy was dressed in a pink sissy adult dress, high-heeled slippers, and stocks.

Published by Diaper Sissy at September 11, 2015

Teacher Takes Control

It was a normal day for me; I was in my classroom and working on the last of my paperwork when one of my students knocked on the door. I waved him in and couldn’t help but laugh when he entered the room wearing a frilly pink dress. He slowly walked up to me and started fumbling through some excuse about how he had lost a bet but I knew better.. He was a sissy, and no doubt, he was sent here for the humiliation he would endure walking through […]

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 […]