Sissy Diaper School Stories

110,351 results
Orientation
Length
Source
Infinite Scroll

Mother Dear Pt. 09

by keptsissy on Sep 13, 2017
Fetish

"I love this place, baby boy. Every time we dine here I think back to that one fateful dinner, the dinner where this all began. The dinner after I came to your home unannounced innocently enough, wanting to take you out to eat only to find you dressed like a girl and on your knees doing what we bad girls do, delightful." She winks at me over her wine glas...

The Diaper kiss curse

by dennstar on Oct 9, 2019
Fetish

(((This is a survivor story, can you survive and keep your teenage or adult minds or will you be cought and brought back to babyhood... will you survive.....)) Jill packed up her books in the library where she was finishing up some of her homework on her free period, she left the library on her way to art class, being in her last year of high school, there w...

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Our Steven, Our Stephanie Ch. 03

by Johnboy9 on Sep 15, 2017
Fetish

This is part 3 of my second story on Literotica, Our Steven, Our Stephanie. I want to thank all those readers for their words of support and encouragement to continue this effort. I hope you enjoy this chapter and future installments. * The next night after dinner, Steven hesitantly approached his Mother, trying to collect his thoughts and words to make hi...

Monica's Downfall

by cloudylez on Feb 21, 2021
BDSM

Monica is an 18 year old high school student living with her mother. After getting an F in two of her classes, her mother decides to punish her for it in the most horrible way possible. Now Monica must work on getting her grades up while dealing with all the stares and laughter from the other students because of that punishment. *****************************...

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Cleaning Out Kelly Ch. 03

by Clausimotto on Sep 15, 2017
Fetish

Later that morning, Kelly called two of her school buddies. Kelly invited Susan and Debbie over for the day and to spend the night. Kelly went to her mom’s room to how she was holding up. “Doing ok, Mom?” Kelly asked. “I’m ok. I’m just a little worn out from all the events of the last day. I had no idea that I was even capable of this. I can’t believe how...

Ms. Marca Ch. 63

by Ms. Marca on Sep 15, 2017
Loving Wives

My name is Marca. I am mid 30’s, 5'10", thick dark hair and a very womanly figure, with 40D breasts (for those of you who need to know, big round nipples silver dollar size) and 38, but very firm, athletic hips. I have been told that I have a perfect complexion. Large dark nipples cap my very creamy gold brown breasts and I have a shaved pubic area. I have a...

Supernatural Exhibitionism

by throwaway0709 on May 25, 2019
Exhibitionist & Voyeur

Natalie Lawmaker is our main character. She loves to be exposed, and has done so thousands of times while getting away with it. The reason she never got into any trouble was because she was always "special". At a young age she found out she could wipe peoples mind, and started playing with it. As she got older she also managed to make people behave...

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Postscript: The End to PIG

by fexhominum on Jul 27, 2020
Fetish

Goddess Ashley met me outside of a Panera Bread for the ostensible reason of returning my credit cards to me. She was sitting alone at a small table, drinking a mango smoothie. She wore a white halter top, black shorts, and white high-heeled sandals. Sunglasses stylishly perched atop that luxurious blonde hair. As I approached, I could see her ruminating on...

Dinner Date with Mommy Pt. 01

by SissyStoryTime on Nov 20, 2018
Transgender & Crossdressers

This is Part 1 of an update on the sissy Sophie and her cruel but loving Mommy, Amanda from the story Meeting Mommy (https://www.literotica.com/s/meeting-mommy) It contains numerous perverse and offensive themes that I'm sure you'll all eat right up. This story includes the following: Femdom, strap-on, implied forced-bi and cucking, enemas, butt plugs and...

Winning Big in Las Vegas

by marykay9 on Feb 6, 2018
Transsexuals & Crossdressers

I was in Las Vegas staying at one of the "lesser" hotels, playing the slots to kill time waiting for a "Shemale" show to take place. I thought that the review would attract other transvestites like myself and hoped that I might get up the nerve to wear my feminine clothes and mingle with other genetically challenged ladies. Unfortunately, a normal crowd surr...