Sissy Boy Phonesex - Diaper Sissy

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 […]

November 1, 2015

A Sweet and Seductive Lady The woman was just partially clothed. And she has the appearance of a candy doll.

Published by Diaper Sissy at November 1, 2015

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Sissy Whorehouse Halloween

Oh man did I have the best halloween ever. There’s never a bad time to add humiliation phone sex to your holidays! This year I got to dress up my little sissy sluts and boy did we have some fun. Instead of a little haunted house we decided to turn our garage into a little Halloween sissy whore house. Instead of passing out candy we passed out blowjobs! My little sissy sluts all stood in a line on their knees as one guy after the other started coming up and […]

October 29, 2015

The lady had a pair of sexy bosoms and was dressed in a western attire.

Published by Diaper Sissy at October 29, 2015

Strap On Training

I think it’s about time for some good ol fashioned pegging phone sex. You lubing up that ass for me you little pegging slut? Mmm I’m going to stand behind that little ass of yours and put on my nice thick strap on. It’s the big black one just like you like it. I’m going to rub my big mushroom head all over that little puckered hole of yours. Are you ready for my cock? This is your training you little slut. You need to learn how to take my […]

October 27, 2015

A Sissy Barbie Girl the lady was dressed in an extremely deluxe version of a traditional white southern belle attire.

Published by Diaper Sissy at October 27, 2015

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Halloween for Sissies

It’s that time of the year! That enchanting smell that comes with fall weather, pumpkin spice lattes, and Halloween. What better opportunity is there for a sissy to go out on the town in the frilliest of gowns? Imagine how much fun you can have just preparing for the event. Going to the store and finding a Barbie pink dress with a full skirt so that you can wear a diaper underneath with no one the wiser. A trip to the makeup counter for a bright lipstick to match. After […]

October 25, 2015

The lady was dressed in a white western costume dress with panty, and she was showing off her ample assets.

Published by Diaper Sissy at October 25, 2015

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Sissy, Sissy

Well what have we here? A big whinny sissy boy! Do you really think that I will let you get away with this naughtiness? Bad behavior does not get rewarded! You will come over here right this minute. Stop that whining now. Where ever did you get that dildo from? Don’t try and pretend that I didn’t see you in the corner with your hand in your diaper, and playing with that big dildo. I saw it and now you will pay for it. Come here! Where did you get […]