sissy boy - Diaper Sissy

October 18, 2020

A beautiful baby drawing of a girl wearing glasses in black colour stood out among the others.

Published by Diaper Sissy at October 18, 2020

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Diapered Sissy

A Sissy Boy for Mommy

Would you believe it if I told you that I got the most wonderful package delivered on my doorstep the other day? Now, I am not sure what exactly I did in order to get blessed in such an amazing and special way, but boy did I ever! I woke up and was having a hard time dragging myself out of bed. I just felt like I was in a funk or feeling kind of blue, so this little blessing could not have come at a better time for this […]

June 15, 2019

He rubbed his thighs together as Mommy Tawny approached

Published by Diaper Sissy at June 15, 2019

Sissy Fucked in Diaper

Andrew rubbed his thighs together, barely hearing the crinkle from his plastic backed abdl diapers as he squirmed on the bed laid out on his back, watching Mommy Tawny walk towards him. Her strap-on was swaying in front of her, and he didn’t even try to look away, the thought of how good that dildo was going to feel inside him made his sissy pussy clench down on the plug inside it in eagerness. It felt so good that a needy moan slipped past his lips and his hips rocked […]

February 10, 2013

Published by Diaper Sissy at February 10, 2013

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Diapered Husband

Your wife called me today. And yes YOU know who YOU are. lol She was pretty hot with you. I bet at this very moment she has you over her knee and is reddening that little tush,LOL! She warned me that you will be calling me later tonight for some AB sitter punishment after she is done with you. You are also to confess and to tell me what punishment she doled out so that I can come up with something suitable to go along with it. So apparently you […]

January 27, 2013

Published by Diaper Sissy at January 27, 2013

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Mommy is just not going to have this silly nonsense anymore. Little AB boys DO NOT put their hands in their diapers. And they DO NOT look at naughty pics on the computer when Mommy or the AB sitter are not looking. Mommy has had quite enough. It is time for drastic measures. I have a few ideas in mind to punish you and deter you from sneaking a wank in your wet diaper. Yes, that means diaper chastity. Locking diapers and chastity devices will need to be employed for […]

January 20, 2013

Published by Diaper Sissy at January 20, 2013

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From sissy maid to sissy AB

This is what a proper sissy maid does. I expect you to show up on my door step, fully dressed and ready to WORK. after I have put you through your paces and shown you what real house cleaning is, then I will reward you with some mommy/sissy AB play time. But first you are going to be a big girl and clean mommy’s house properly. You will clean the toilets, vacuum, dishes, trash and you will take care of some of mommy’s most prized possessions. My extensive shoe collection. […]

July 5, 2011

Published by Diaper Sissy at July 5, 2011

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sissy whore

I know of an adorable sissy slut who we’ll call Janine. Janine is not her real name, or his real name, but using the name Janine protects the whore. Janine always wants his Mistress to expose him, to humiliate him and to turn him into an owned whore. What I am hoping is to break Sissy Whore Janine and to turn her into a Tgirl Cock Sucking Jizz Junkie before he knows what hit him. She has the look,s my god she is gorgeous. Now she just needs a push […]

March 16, 2011

Published by Diaper Sissy at March 16, 2011

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Forced Feminization | A sissy’s post

Today I have another guest blogger. A sissy who is taking another step in girl sissy boy training wanted to let me know (and everyone who reads this) how forced feminization has changed him. Today my newest adventure with Miss Scarlet began. I thought I would take some time to write about what forced feminization has felt like for me. I’ve always been the timid type of guy around girls and even around other men. Now I feel like I fall somewhere between man and woman though. I’m not quite […]