March 19, 2026
a diapered sissy goes to the store with mommy
Published by Diaper Sissy at March 19, 2026
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Sissy diaper training, sissy mommy takes me shopping

I woke up in my crib wearing the cutest baby pink satin dress Mommy picked out. It’s all poofy layers of chiffon and tulle that swish and rustle every time I toddle, with tiny white lace hearts sewn along the hem like they’re giggling at me. Underneath? My thick, crinkly diaper, the kind with the little teddy bears on the front so everyone knows I’m a little sissy baby, and the frilliest pair of panties ever, pure white with rows of baby pink ruffles that peek out no matter how […]
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March 13, 2026
sissy shows off her training to mommy and her friends
Published by Diaper Sissy at March 13, 2026
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Sissy showing off training

It started with Mommy calling me into the living room, her voice like warm honey. “Come here, my precious rose bud,” she cooed, and I waddled over in my fluffy pink dress, the one with layers of lace that swish swish against my thighs. The fabric is so silky, hugging my curves in all the right places, making me feel like a dainty doll ready for tea time. Underneath, my lacy panties peeked out just a bit, all frilly and white with tiny rosebuds embroidered on them, but today Mommy […]
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June 22, 2025
diaper sissy assignments
Published by Diaper Sissy at June 22, 2025
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Mommy’s Assignments After Our Phone Call Together

One thing a lot of new callers don’t realize is that the fun doesn’t have to stop when you hang up the phone. Some of our best mommies love giving assignments that keep you in sissy mode long after the call ends. And trust me, they will follow up to make sure you did what you were told. The assignments vary depending on your mommy and what kind of session you had. Maybe she tells you to stay in your diaper for the rest of the evening. Maybe she wants […]
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July 25, 2021
Near the wall, a Diaper Man is standing and sporting a white baby girl suit.
Published by Diaper Sissy at July 25, 2021
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Abdl Retreat For Abdl Training!

My current boyfriend, Greg, isn’t really boyfriend material, so I’ve decided to go out and get myself a new one, someone that better fits the mold of a grown man. Greg definitely doesn’t do that! Between his small dick and his natural submissiveness, he’s more of a sissy baby than a real man. I don’t want to just drop him, though, it’s not like the poor thing can help it. Also, I would feel bad for the next female that he’s able to lure in through pity and lies. Best […]
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September 22, 2019
Colored diapers White is more attractive and usable.
Published by Diaper Sissy at September 22, 2019
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Naughty, Messy Sissy!

  Diaper sissy Amanda was crying harder than she ever had before; fat, round tears streaming down her face as she fussed in her diapers. “Mommmm-yyy pwease change meee!” She whined and whimpered between body wracking sobs, her sissy diapers stretched to gargantuan proportions behind her. “Aww, what’s the matter, baby wetsy pants?” Her hypnosis mommy mistress mocked her, tugging at the back of the over filled diaper stack. “Don’t you remember your sissy rules, princess?” The pathetic sissy baby struggled to choke back her tears long enough to gulp […]
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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 […]
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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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June 20, 2013
Published by Diaper Sissy at June 20, 2013
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Panty Boi Phone Sex

Well, well. What have we here? A little panty boy who’s been playing around in Mommy’s panty drawer again?  I thought I’d already told you several times to stay out of here. You know you’re not supposed to be putting on Mommy’s panties like this. Ooooh noooo – don’t you sit there and try and tell me you’re sorry. Clearly, you aren’t very sorry, or else you would not have done what I specifically told you not to do. You’re only sorry that you’ve gotten yourself caught again.  Do you […]
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May 3, 2012
Published by Diaper Sissy at May 3, 2012
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Sweet sissy girl

Be my sweet sissy abie girl and mommy will make sure you get everything that you need to be a happy sissy girl! I hope my sweet little sissy boys are doing good? i have a great story to tell you about a 2 girl call i had with my friend Kita, she played the mommy and i was the auntie, and abie Damon was our sweet little sissy girl. sissy Damon wanted to be a very good girl for both mommy and auntie phone sex Crissy. we changed her […]
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