sissy - Diaper Sissy

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

Categories

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

Categories

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

Categories

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

Categories

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

Categories

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

Categories

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 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

Categories

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

A Magnificent Dress It was blue in colour, and the gown itself was of the size of a small child's gown.

Published by Diaper Sissy at October 25, 2015

Categories

Mommy Spoils Her Baby

Good morning my little adult baby. Mommy made you a big yummy breakfast downstairs. Mommy lifts you and sits you up in your high chair at the table. I strap the little belt across your waist so my sweet baby doesn’t fall out. Mommy made you a supper nummy breakfast to start off a super fun day. I made you some pancakes! Some are heart shaped because I love my little baby. Some are diaper shaped. And some are dress shaped. Mommy knows how much her sissy baby loves their […]

October 25, 2015

A girl's gown is shown in the image, and it is very pretty in light pink.

Published by Diaper Sissy at October 25, 2015

Categories

Perfect Sissy Boy

I got the chance to play with the most well behaved little sissy boy the other day! He told me that he just loved to be put in adult baby diapers. They got him so excited! Well knowing that, I made it my personal mission to have him make a big mess of a certain sort in his diaper for me. He listened to everything I said, and when I had him lay across my lap and give him a few hard spankings just because I can, he could hardly […]