sissy - Diaper Sissy

December 6, 2015

The banner for "Naughty Sissy" looked lovely and was pink in tone.

Published by Diaper Sissy at December 6, 2015

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Mommy Barbie’s Naughty Sissy

My sissy was so naughty the other day. I was changing her diaper and putting on a nice little dress and she just wouldn’t stop squirming. I know she was anxious because I was taking her to the park for the first time in her sissy dress, but that’s no excuse for being so rude while I was trying to make her pretty! I told her to relax the first time, the second time I told her that she really needed to calm down, and the third time I told […]

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 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 22, 2015

A Sissy Dress This is the adult dress for the little girl. Adult users are the ones who make use of it.

Published by Diaper Sissy at November 22, 2015

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Dressing Up Sissies

The holidays are upon us and as the time goes by and we get closer to Thanksgiving, Christmas Eve and Day, and New Year’s Eve, I keep thinking about how many pretty outfits and dresses I can put my little sissies in. Most of them are so very loving and obedient and they are always sure to be completely submissive to everything that I say or tell them to do. They never talk back or fight me on it when I tell them that I will be putting them in […]

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 […]

November 6, 2015

In Mommy's Slutty Outfit, a woman is shown walking along the street while sporting a miniskirt.

Published by Diaper Sissy at November 6, 2015

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Mommy’s Sexy Clothes

Your fetish for slutty clothing started at a young age and you know exactly what started it all. Your mother was always strutting around in tight skirts, low-cut tops, and high heels. Your friend’s parents would comment that the way she dressed made her look like a whore but you always thought she was the prettiest woman you’ve ever seen. Imitation is the sincerest form of flattery, isn’t it? So you think she would be happy to see how hot you look when you wear the same type of clothing […]

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 […]