Sissy Boy Phonesex - Diaper Sissy

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 […]

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 31, 2015

A girl stands for a photoshoot, and the background is filled with Pink Flower Standup.

Published by Diaper Sissy at August 31, 2015

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Dressing up

Small pink dresses are among the things I love most in the world. With puffed little sleeves and ruffled edges and dainty bows, they become the definition of cute. Cute, small, and feminine. When I’m done changing a well-behaved abdl, my favorite thing is to find the daintiest and sweetest of outfits to subject him to. His cloth diaper is bulky, but the rubber pants I pull over the fabric makes it seem less bulky and transforms it into a sweet representation of infancy. With his rubber pants snugly around his […]

August 30, 2015

A girl is dressed in a small black gown that is both hot and sexy.

Published by Diaper Sissy at August 30, 2015

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Cuckolding My Sissy

I know you’ve been waiting for this all night; I heard you creep out of your bed, tip toe quietly to the bathroom, and crack open the door, and I knew just when to start undressing to make sure you got see everything. I started slowly, sliding down my skirt and revealing a tiny pair of panties, barely big enough to hide my pussy. Then my top came off to reveal my big, soft tits, my nipples barely hidden beneath a thin black bra. It got me so wet knowing that […]

August 24, 2015

Unclothed during the photo shoot, the blindfolded boy looks incredibly attractive and seductive.

Published by Diaper Sissy at August 24, 2015

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Don’t Tell Mommy

You have been such a good little sissy, that I’ve decided it’s time for a surprise. Your mommy and daddy are going to be gone for a while, so your wonderful ABDL babysitter went out and picked up a special outfit that I want you to wear tonight! After I strip you naked, I’m going to put a cute little diaper on you and help you into your new, tiny, lacy maid dress. I’ll help you slip into your new white stockings, slowly pulling them up on each leg, before […]