December 26, 2019
Standing on the ground wearing the white diaper is a feisty grandmother.
Published by Diaper Sissy at December 26, 2019
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Sissy Baby Turned Into Sissy Puppy!

Michael eased down on all fours, leaning forward so that his bottom lifted up into the air, his sissy dress falling down a bit to his waist. He started to lap at the dog bowl full of baby formula that Auntie Brenda had put down for him, licking it clean, then switching over to doggie bowl with pureed baby food right next to it and gave that one the same treatment. He had been a naughty sissy baby, and his auntie decided that some humiliation punishment would be just want […]
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July 5, 2019
There is neither a ruffle nor a diaper sissy on the light pink ruffled panties.
Published by Diaper Sissy at July 5, 2019
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My Sissy Baby Girl!

I have a pretty pink dress, a lace bonnet with a wide ribbon to tie underneath your cute chin, a pair of shiny white leather buckle shoes, lacy anklet socks, some ruffled pink diaper covers, and of course, a pink princess diaper. It’s all for you! You, silly thing, are going to be by sweet sissy baby girl and that means that around the house you don’t wear a thing that is cute as a button.  Some days I might want you to waddle and crawl around, a pacifier in […]
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January 27, 2019
he is an adult baby sissy diaper boy; please humiliate him.
Published by Diaper Sissy at January 27, 2019
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Forever A Silly Sissy Baby

You will always be a diapered sissy baby.  Everything that you wear will be lacy, frilly, super feminine and girly and sissified! You did try for awhile, and I know you wanted it to work, but there never was a chance that you could do it. So don’t feel ashamed about this, dear, it’s just your nature.  There’s no fighting who you are, so you need to embrace it!  Though you should always be horribly embarrassed with how your tiny sissy clittie always stays hard inside your diapers. I do […]
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April 10, 2017
A woman is standing in the room wearing a diaper and white stocking socks, and her legs are showing.
Published by Diaper Sissy at April 10, 2017
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Brenda’s Sissification Phone Sex

Now that you’re home, dear, it’s time for you to get comfortable! Take off all those horribly masculine clothes and slip into these lovely clothes I have laid out for you! It is definitely time for some sissification phone sex. I want you to put on the white thigh stockings with the bows, that pretty Catholic school girl skirt, the gloves, the lacy shirt, all of it!  Yes, of course the diaper!  That is why I laid it out on the bed, and why your skirt is so short.  I […]
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October 11, 2015
A stylish girl is posing for the photoshoot, and she is lovely. She displays her sexy hips.
Published by Diaper Sissy at October 11, 2015
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Sharing Mommy’s Pet

Tonight’s a big night for you, Little Miss! I’ve picked out lots of pretty Sissy dresses that I think you’re going to love, and a bunch of frilly panties and bras to match! We’re going to get you all dressed up and then some of Mommy’s friends will be coming over to help me take care of you. We’re all going take turns breastfeeding you, holding you close to us as you suckle away on our big, squishy tits. Once you’ve had enough of that, then it will probably be […]
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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
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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 […]
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September 9, 2013
Published by Diaper Sissy at September 9, 2013
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My litte girl

Hi sissy bois. I just love feminizing and cuckolding young men.  Feminization phone sex is an art and I am the artist and you my little one are the canvas.  I have been sissyfying and feminizing men for a long time, but it still has the same thrill for me as it did the first time I made my baby brother wear my panties and clothes. Are you a sissy baby? A panty boy? Sissy fag? No matter what the title if you enjoy being feminized and humiliated by a […]
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June 7, 2013
Published by Diaper Sissy at June 7, 2013
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Mommy Gets a New Baby Girl

Timmy, my 15 year old son had known how sad Mommy had been because I was never able to have a baby girl. Some one I could dress in pretty things, gossip about boys with, and pass on all my beauty secrets to. After much thought, I devised a plan that would show my boy how he could make me feel better. I had went shopping all day, and it must have been kismet,  because I was able to find everything I needed for my new little girl all in his size! […]
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March 9, 2012
Published by Diaper Sissy at March 9, 2012
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Manipluative Mandy

Being a Sitter can be a great deal of fun for a manipulative gal such as myself. These little ones I sit for are so very curious and most are willing to please, the ones that are a bit more defiant well, let us just say that I am skilled in the art of persuasion. The last little one I sitted for, just last night a matter of fact, was very curious about the difference between him and I. He kept touching my skirt as we sat on the couch […]
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