Diaper Sissy Chastity Stories

13,981 results
Orientation
Length
Source
Infinite Scroll

Alexis' First Time Ch. 01

by alexis19901 on Apr 13, 2020
Transgender & Crossdressers

I've never attempted to write a story before, but while stuck inside I thought I'd give it a go! First off let me say that this story is pure fantasy, any names that might be used aren't real people. I'll start off with a little of my back story before I get into the story. I started crossdressing when I was younger, and it started with the usual story of...

Naughty Pictures

by DeborahC on Jul 2, 2019
Transgender & Crossdressers

The gallery was as quiet as you would expect on a Wednesday morning, a few lonely souls wandering around enjoying the peace and visual treats that hung on the white walls. The exhibition of WWI war artists mainly Nash, Bomberg, Dix and Lewis drawing its particular audience, contemplative, those that were given to calm observation. The smell of coffee and ba...

Enlightening M Ch. 02: Key Lime Pie

by busymonsters on Jul 3, 2019
Loving Wives

It had been about a year since we last invited another man into our bedroom. During that time, I had a major surgery that definitely took something out of me and worried about fulfilling M's very high sex drive. As I recovered, I noticed it taking longer and longer for M to reach orgasms and sometimes she would even fake them to try to spare me the embarrass...

Teacher Takeover

by redwolf555 on Aug 5, 2019
Fetish

How did it start? You ask. I'll tell you. Let me introduce myself. My name is Gregory Sellers and I was a high school teacher at a private school. I had been divorced for two years from my wife, Taylor. It all started when one Friday after school was over, I was in my office when I dropped a box of paperclips. I was on my knees picking up the mess, when she...

Mommy's Naive Sissy Ch. 02

by Subone1 on Dec 24, 2019
Transgender & Crossdressers

Note to reader: This is pure fantasy, take it for what it is. Don't try in to inject realism into this story, it won't work! Just enjoy! ***** A few months after my 18th birthday, Mommy told me we were having a guest over for an afternoon cookout. She wanted to wait until I had fully recovered from my boobie surgery! I was sore from my surgery for a few w...

My First Hotwife Experience

by Iloveclubo on Dec 9, 2019
Loving Wives

I knew that the day would come, and now the opportunity to act on it, when I would tell Mike, my husband, how much I really did want to experience another man's cock. It makes my pussy ache when I would fantasize about holding a new cock in my hands and using my moist lips to make it grow and become rigid in my mouth, my hands slowly stoking its length while...

Ginger and Cinnamon

by Cal Y. Pygia on Jul 15, 2020
Transgender & Crossdressers

Studying my reflection in the full-length mirror, I like what I see, mostly. For me, the appearance of a woman's face falls into one of six possible categories: ugly, plain, ordinary, cute, pretty, and beautiful. At one time, I put a celebrity's face with each category, but I've removed the faces, deciding that including them with such labels was tacky at...

Are You Kidding Me?

by Paniolo Boy on Feb 26, 2019
Erotic Couplings

"Are you kidding me?" I told Niki! Whoa! This was too much to handle. "Now James, I know it sounds kinky and weird, but would you do this for me? Puulllleeeeeaaaaassseeeee?" "But Niki ..." "Please James? I would be forever indebted to you. Puleeaase?" Shit! How can I refuse her? "Niki ..." I replied with a worried look, "this is going to be embarrassi...

Shadow Dance Ch. 01

by tame_goddess on Apr 10, 2019
First Time

I close my eyes as I grant the cherry at the end of my joint its vitality, letting the smoke billow around my head while the comforting scent of nature's medicine caresses my nostrils. Sitting cross-legged on my bed and topless, I lean forward slightly and rest one arm on my lap, the elbow of the other rested on my stocking covered knee as I pull the joint a...

Hotwife, Her Daddy, and Her Cuck

by fallstaffer on Jun 4, 2019
Group Sex

I come up behind Angie and gently slip off her thick Turkish terry cloth robe, letting it fall to the floor by her feet. Her husband sits on the gray pleather couch watching my hands kneed deep into his wife's large round breasts. They are thick and soft and heavy and her flesh craters as my fingers press into her. When I kiss her neck, she arches her back a...