sissification - Diaper Sissy

October 6, 2019

The man is sitting on a chair and wearing a lock, and there is a pink Sissy Chastity sex toy nearby.

Published by Diaper Sissy at October 6, 2019

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Sissy Locked in Chastity

All too often, a sissy will come my way with a grave misconception about just what they are permitted to do and what they are forbidden from doing. Too many sissies will assume that just because they may have been behaving lately, that they are allowed to take it upon themselves to decide to start playing with that little peepee. Sorry, sweeties! Wrong! That pathetic little thing belongs in one place and one place only: locked up tight in chastity! That look of disbelief and humiliation on their face when […]

June 30, 2019

Stepmother wearing pantyhose while waiting for dig Bick boy

Published by Diaper Sissy at June 30, 2019

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Showing Off Sissy

“Come on out, dear!” You can hear her calling you from the living room, followed by a bunch of excited giggles from her friends. Running your hands down the front of your short, pleated skirt you wonder how much more of this sissy humiliation you can stand. Here you are, dressed in an adult baby diaper, plastic pants, and oh so short pink skirt and matching blouse, about to walk down the hall and present yourself to your sadistic girlfriend (now your Mommy!) and her attractive female friends, the kind […]

March 24, 2019

solid black leather on one side & red padded garment leather on the other side

Published by Diaper Sissy at March 24, 2019

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Sissy Spanking Needed!

You have misbehaved and been a naughty diaper sissy, haven’t you? Running around, flirting with all the men, flipping your skirt up around them like a little cock tease! That is simply not acceptable, and you know that you are going to be punished for your behavior. Go ahead and kneel next to the bed, resting your arms across it to get in position for your well-deserved paddle spanking. You will count out loud every time I bring the paddle down on your bottom and at the end of your […]

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 […]

July 7, 2018

A hot boy is standing while sporting a diaper and sucking a baby's breast.

Published by Diaper Sissy at July 7, 2018

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Forced Sissy Phonesex

Are you upset about your outfit, dear? I did tell you that I wasn’t to going to put up with your cheating anymore, didn’t I? Yes, I did. From the way you kept right on, I assume you thought you were too clever to get caught. You aren’t, though. You are bumbling and inept, stumbling about while I watched and waited. And took lots of pictures while I waited! Goodness, imagine what would happen if these got posted online, the damage they would do to your life. Your job, your […]

March 16, 2018

Property Bondage Rose Collar Submissive Smooth Sissy Prostitute Wench Tart UK

Published by Diaper Sissy at March 16, 2018

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Forced Diapered And Publicly Humiliated!

So earlier this week I got a date planned for this guy and I met him at a fetish club and he was looking to try something new and was looking for a Mistress. So I invited him over to my house for dinner, I had something very exciting to try. He arrives and I let him and Immediately commanded him to take off all of his clothes and get on his knees. I place a hot pink Collar around his neck. A Bondage hood over his head that was […]

January 21, 2018

Girl undergoing forced feminization is resting on the bed and wearing a pink dress and a white diaper.

Published by Diaper Sissy at January 21, 2018

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Forced to be a Diapered Sissy

I really do hope that you aren’t too fond of your balls, dear, or your cock for that matter. Once I’ve started your forced feminization phone sex, you won’t have much use for them at all. I will turn you into a full-fledged sissy…and for an extra helping of humiliation, I’m going to tuck you into a thick adult diaper. It will be awfully funny to see you finally walking as if you have something substantial between your thighs! I will have you completely decked out in stockings, a frilly […]

August 26, 2017

Big Black Cock, The black dude reveals his Big Black Cock. Big Black Cock.

Published by Diaper Sissy at August 26, 2017

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Black Cock Craving Sissy

Now, you know that I’m going out with my friends tonight, but I’ve decided to get a babysitter for you! You’re not allowed to change your own diaper, after all. Being a diapered sissy like you are means that you need a sitter that can meet all your needs. Your new sitter is very hands on, very firm…and he has a big black cock to fill up that tight ass of yours, if you behave yourself. Or it could be if you don’t behave yourself. Whether it’s a reward or […]

June 19, 2017

A Little Porn Lock man is seated in the chair and wearing a pink pair of hand gloves and a t-shirt.

Published by Diaper Sissy at June 19, 2017

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Forced Sissy Punishment

How about we play a little game, dear? See, you’ve turned out to be an absolute horrible husband and an even worse example of a man. You expect me to wait on you hand and foot, and you can’t seem to help but leave tracks in all of your underwear! I shouldn’t have to put up with this from a grown man, but you know who else acts like this, and it’s expected? Babies! Which is why I’m going to dress you up like one, thick adult diapers and all. […]