sissy - Diaper Sissy

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 […]

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

There is one A Pretty Doll in this photograph.

Published by Diaper Sissy at December 4, 2015

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Mommy Got You a Surprise

Mommy tells you that she has a surprise. There’s something she’s holding behind her back, just out of sight. Can you guess what it might be? It’s nothing naughty or kinky. She has a big smile and is so eager to show you what she picked up special for you. It’s a dolly! Oh no! You try to smile, not wanting to disappoint your excited mommy. “What do you think? Isn’t it just beautiful? What will you name her?” You stumble over your words. She’s really pretty, mommy. Umm.. I […]

December 3, 2015

This photograph depicts Pioneer Park in San Diego, California, which is a lovely park.

Published by Diaper Sissy at December 3, 2015

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I love taking my little sissy to the park and showing her off to all the other Mommies. They’re always so jealous of me because my little sissy is so pretty and well behaved and obedient. They know that I could ask my sissy to do absolutely anything and she would do it right away. One of the mommies didn’t believe me though, so I decided to show her. I told my little sissy to get down on her knees and open her mouth. I told the other mommy she […]

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 21, 2015

The image shows a unicorn plush toy that appears to be a soft stuffed toy.

Published by Diaper Sissy at November 21, 2015

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Sissy’s Stuffed Toys

Mommy Lauren knew you were a sissy when she caught you playing with Barbie dolls. You knew that Mommy knew when she started buying you cute and cuddly stuffed animals! No more hard plastic trucks and wooden logs for you- now it’s all velvety soft dolls! What would you friends think if they saw your room now, with bright pink bunnies and fluffy unicorns? They’re so nice to play with! You can hug them as you fall asleep, lay back on them as a pillow, and have them dance around […]

November 19, 2015

The image contains brrrrr letters, which look nice.

Published by Diaper Sissy at November 19, 2015

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It’s Getting Colder!

The weather has started getting cooler so it’s about time that I update my abies’ wardrobes to make sure that all my sissies stay warm this winter! I like to start by pulling out my long sleeved dresses, ones that are usually made of thicker warmer materials like fleece or heavy cotton. Then, I like to pull out fleece stockings with cute patterns (like snowflakes or flowers) along the legs. Usually that’s enough to keep my sissies nice and warm, but just in case, I like to have a few […]

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 […]