Sissy Boy Phonesex - Diaper Sissy

August 30, 2016

A fetish woman is posing for a picture while standing in a public area while donning a black stocking.

Published by Diaper Sissy at August 30, 2016

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Sissy Baby Phone Sex

Who all out there can say they’re ready for some sissy baby phone sex? Sissy adult babies are already fun to begin with but when they want to also be a lurks sissy slut with their mommy it makes them twice as fun to play with. Mommy loves pimping out her sissy adult baby slut to daddy and all of daddy’s friends too! Maybe you can be daddy’s good little sissy adult baby bitch and come out in nothing but an adult diaper and plastic panties that barely cover it. […]

August 16, 2016

Published by Diaper Sissy at August 16, 2016

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Pretty in Pink for Graduation

Look at the way you sway in that pretty pink dress. I just bought you so much new sissy stuff for the play room. You’re gonna love it. You know I’m so proud of you for graduating Sissyfication college. I know it’s all you wanted. Now you’re the perfect little sissy slut mommy had always dreamed of you to be. I bet you can’t wait for our after party celebration just you and I. Mommy is gonna teach you how to use some of these toys. Oh but I’m sure […]

April 20, 2016

A Barbie Sex The lady was dressed in a barbie outfit complete with stockings and was walking around in pink high heel slippers.

Published by Diaper Sissy at April 20, 2016

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Small Penis Humiliation

I saw what you were doing the other day and I think it’s going to make for a great small penis humiliation and sissifacation phone sex story. You thought I was out at work didn’t you? Well I came home early and boy did I come home to a sight to see. I was about to walk into my bedroom when I heard something in there. I saw the door was cracked when I clearly remember shutting it when I left for work. I peeked my head in only to […]

April 20, 2016

A girl is sitting on the edge of the bed and wearing black lingerie underwear.

Published by Diaper Sissy at April 20, 2016

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Sissy Phone Sex

Are you a sissy boy phone sex lover? Don’t try and deny it now! I saw you wearing my stockings around the house when I wasn’t home. I noticed all of my lingere was a little stretched out and even had some hair on it. That hair certainly wasn’t from me, so it had to be you. Still denying it? Well that’s alright because I have proof. I set up a little nanny cam in my bedroom before heading off to work this morning and sure enough when I came […]

January 18, 2016

In this image, a lovely girl stands in the room, wearing a lizabeth print dress and looking cute.

Published by Diaper Sissy at January 18, 2016

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Sissy Baby Fun

I love spending time with my favorite little sissy baby. Do you want to spend the day with Mommy? Lets get you dressed first. I pull out a pretty pink babydoll dress and you raise your arms so I can put it on you. I pull out a blonde wig and place it on you and a pink headband to match. You tell me you want to look pretty like mommy so I place some pink blush on your cheeks. I put on your shoes and socks and we’re ready […]

December 10, 2015

There were numerous Christmas presents on the ground for the people.

Published by Diaper Sissy at December 10, 2015

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Christmas Surprise

Mommy was so excited Christmas morning. She and you had spent a lot of time putting strings of bright lights and pretty ornaments on the tree, and now there were big boxes wrapped in paper sitting beneath it. Mommy pulled out one of the boxes, one covered in long curls of ribbons, and handed it to you. Her face was radiant as she waited for you to tear off the paper and see what she had for you inside. You tried so hard to smile when you looked at all […]

December 4, 2015

Published by Diaper Sissy at December 4, 2015

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You Big Sissy

You are a big sissy aren’t you? Always wanted to wear dresses, but never told anyone or ever tried one on until that first day in December. You saw me getting dressed for my Christmas party and I saw you peaking at me through the half opened door. I asked you if you liked my pretty, pretty, party dress and your eyes got real big and you nodded your head yes. You walked over to me and started feeling the pretty red satin material with your hands rubbing up and […]

November 28, 2015

A Pink Princess Dress The doll was dressed in a pink princess gown. It's standing close to the window.

Published by Diaper Sissy at November 28, 2015

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You’re Mommy’s Little Girl

Oh no! Mommy caught you trying on her pretty bra and panties set and now she’s decided that she’ll turn you in the baby girl that she’s always dreamed up. What started as a bit of curiosity is now going to become a lifestyle. Everyone is going to find out that you’re a big sissy! You only wanted to try on her sexy pink bra and panties once. That’s all! You liked looking at mommy as she got dressed because she looked so pretty with her big, milky white tits […]

November 12, 2015

He is a handsome man wearing a black clothing and wearing makeup.

Published by Diaper Sissy at November 12, 2015

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Forced To Be Pretty

You’re in big trouble now! Mommy Lauren caught you in the bathroom, playing with a lipstick she had left on the counter. She had always thought you were a big sissy and now she knows for certain. She’s not going to let you off the hook so easily. Mommy Lauren tells you to sit down on the toilet and stay still, she’s going to make you so pretty. She takes the lipstick out of your hand and tells you to pucker your lips. She applies a thick layer of hot […]