March 24, 2019
solid black leather on one side & red padded garment leather on the other side
Published by Diaper Sissy at March 24, 2019
Categories

Sissy Spanking Needed!

You have misbehaved and been a naughty diaper sissy, haven’t you? Running around, flirting with all the men, flipping your skirt up around them like a little cock tease! That is simply not acceptable, and you know that you are going to be punished for your behavior.  Go ahead and kneel next to the bed, resting your arms across it to get in position for your well-deserved paddle spanking.  You will count out loud every time I bring the paddle down on your bottom and at the end of your […]
Do you like it?42
Read more
January 27, 2019
he is an adult baby sissy diaper boy; please humiliate him.
Published by Diaper Sissy at January 27, 2019
Categories

Forever A Silly Sissy Baby

You will always be a diapered sissy baby.  Everything that you wear will be lacy, frilly, super feminine and girly and sissified! You did try for awhile, and I know you wanted it to work, but there never was a chance that you could do it. So don’t feel ashamed about this, dear, it’s just your nature.  There’s no fighting who you are, so you need to embrace it!  Though you should always be horribly embarrassed with how your tiny sissy clittie always stays hard inside your diapers. I do […]
Do you like it?86
Read more
November 18, 2016
This image depicts a pink A Sissy Dress that is both adorable and coloured pink.
Published by Diaper Sissy at November 18, 2016
Categories

My Cute Little Sissy

  What would a good sissy boy like you do for his favorite abdl Mommy? Would you wear what I want you to wear, do what I tell you to do?  What if I want you to put on the prettiest, frilliest dress in your closet so I can watch you walk around all day long being the cutest little thing ever? I’ll put a bow in your hair, some lacy white socks on your feet, and a pair of shiny Mary Jane patent leather shoes on you to complete […]
Do you like it?83
Read more
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
Categories

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 […]
Do you like it?37
Read more
April 20, 2016
A girl is sitting on the edge of the bed and wearing black lingerie underwear.
Published by Diaper Sissy at April 20, 2016
Categories

Sissy Phone Sex

Are you a sissy boy phone sex lover? Don’t try and deny it now! I saw you wearing my stockings around the house  when I wasn’t home. I noticed all of my lingere was a little stretched out and even had some hair on it. That hair certainly wasn’t from me, so it had to be you. Still denying it? Well that’s alright because I have proof. I set up a little nanny cam in my bedroom before heading off to work this morning and sure enough when I came […]
Do you like it?56
Read more
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
Categories

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 […]
Do you like it?82
Read more
December 4, 2015
Published by Diaper Sissy at December 4, 2015
Categories

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 […]
Do you like it?44
Read more
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 […]
Do you like it?93
Read more
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 […]
Do you like it?14
Read more
1234
Call Now Button