sissy - Diaper Sissy

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 […]

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 27, 2015

a pair of sissy pants in pink and white The lady was dressed in a frilly sissy panty that was pink and white in color and did not have any designs on it.

Published by Diaper Sissy at October 27, 2015

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Dressing Up My Little Baby

My little boy is so much better as a sissy in a dress. Brian turns into Briana like magic when I slip him into a lacy skirt and top. Briana squeals with delight at anything pink and loves to play with mommy’s makeup. I see how Briana looks enviously at my painted nails, but I can’t let her use my nail polish on her own fingers like she wants- she would make such a mess! My makeup is fine though. She’s darling with a bit of barbie pink lipstick on […]

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 […]