Sissy Diaper School Stories

110,351 results
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Infinite Scroll

Private School

by FelineFiction on Sep 2, 2017
Erotic Couplings

My senior year in high school was only a month away. I was 18 and ready to get out of my dumb prissy private school. My Mom and Dad had made me spend 4 years at an all-girls private school and I hated almost all of it. Besides making it almost impossible to have a boyfriend the uniforms we had to wear were hideous. Dark blue pleated skirts that hung to your...

The One That Got Away

by LeCoach on Sep 13, 2017
Erotic Couplings

Do you believe in love at first sight? Well I sure do. Happened to me back in my last year of high school. I'd grown up in Los Angeles, California and was very comfortable in my neighborhood. I had lots of friends and interests. I fit in. Well, my parents decided it was time to "Move on" and sold our old two story home on the Angeles Mesa and headed out to...

The Bet

by cybele_13 on Aug 19, 2017
Exhibitionist & Voyeur

So, I get into trouble in school. What kid doesn't? I'm 18, about to graduate, so what's the big deal. How am I gonna learn if I don't make mistakes? Well, at least argument works on Daddy... I got caught after school today in one of the storage rooms with two of the guys from the football team. They literally had their pants down. I was jerking off the o...

Alternate Universe

by Thundertickler on Sep 17, 2017
BDSM

In 2020, I lived in an apartment in New York City in Queens by myself I was close to my 29th birthday and since my 25th birthday, I had lost close to 50 lbs and gained some muscle, had a flat midsection, and had the first beginnings of a six-pack. I was by then, 5'11" and weighed 150 lbs, which was my goal weight. When I turned 24 though I peaked at close...

Nothing to Lose

by J-Nite on Sep 13, 2017
Erotic Couplings

The summer had come and gone, without any memories or stories to share. All that mattered now was going back home; packing and getting my ass back to college for my last year. I had been away from home the entire summer, driving from town to town shopping around for a grad school that would suit me. I had two weeks to get home to Georgia, pack my stuff and b...

And So It Begins

by OhCrap on Sep 17, 2017
Non-Erotic

Just something I whipped up. It's non erotic since it deals with pre-coming of age. It's basically the premise for more post coming of age. Call it a background or prologue. Yes. Prologue will do. Imagine that. A prologue that was actually written prior to a story beginning. Being a fan of quite a few types of Literotica stories and authors and being creat...

Holly and Keith

by tnbnb on Sep 13, 2017
Romance

Holly - I first developed a crush on Keith Carter more than 15 years ago when I was seven years old. One day I was at the playground with my mother, Miss Carol and her twins, Brad and Tommy Jr. My parents were best friends with Miss Carol and her husband, Tommy Thomas Sr. I hated the twins. They were two years older than me and it was always two against one....

Morgana's Painful Lesson

by Morganauk on Sep 16, 2017
BDSM

Morgana stood outside the Headmaster's office, nervously holding the note in her hand. She didn't know the contents of the note, only that it was about her and that she was in some sort of trouble. At 18 years old she already had a woman's figure and somehow looked out of place wearing the compulsory school uniform. She was short with blonde hair and blue...

STRIP Ch. 15

by HarveyMarcus on Sep 26, 2017
Mature

Chapter 15 - The Return of Quinn's Quim WARNING: The following story is for the entertainment of ADULTS ONLY, and contains descriptions of explicit sex. If you are not an adult, or reading sex stories upset you, or you are offended by subjects of a sexual nature - do not read any further! This story is for entertainment only. It contains adult oriented...

The Sexual Adventures of Ben Washin

by afolabi70 on Sep 13, 2017
Interracial Love

My name is Ben Washington Jr. and I have a confession to make. While I might look like your average race-conscious, positive brother, I am not. I have a wild undercover sex life. I have had many crazy, sexual adventures that have taken me to unbelievable places. Like a lot of brothers, I grew up with a single mother. Mom had gotten pregnant with me when she...