Diaper Sissy Chastity Stories

13,981 results
Orientation
Length
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Infinite Scroll

Stuart's Psychologist

by justincbenedict on Sep 13, 2017
BDSM

"Take them down, Stuart...like the shameful little boy that you are!" Stuart couldn't believe Dr. Townsend was talking this way. And right in front of Moira, too. She looked horrified at Stuart's therapist, a muscular silver haired, pinstriped John Forsythe look-alike--yes, he looked very much like Forsythe's "Blake Carrington" character on Dynasty. Dr....

Maltese Penis

by Jenny _S on Sep 1, 2017
Humor & Satire

Someone knocked on glass door of the Spade & Archer office. From under his dark brown fedora, Sam Spade pried open one eye then placed the half bottle of Old Sweat Sock in his desk drawer while he shoved the cock he had been stroking back in his pants. Rising, he straightened his trench coat, drawing the belt tight around his waist and tied it in a knot. "Co...

My Date

by corsetheelscollar on Sep 16, 2017
Transsexuals & Crossdressers

Chapter One The first date went well. I met Francesca outside the cinema. She looked exactly as she had described herself. Tall, particularly in the incredible black boots, athletic, with long auburn hair. I was attracted to her straight away, and loved the way she took my arm, smiled and walked with me into the cinema. We had a few minutes before the fi...

The Secret is Out Ch. 01

by erinssilence on Sep 16, 2017
Transsexuals & Crossdressers

This story is not based off a true story. It is about a crossdresser who chooses to go to a conservative christian college only to be found out by their roommate. The story is a bit slow going at first but is necessary to set up the remaining chapters that are to come. **************** My name is Kelsey. Well, actually the name I was born with is Kevin but...

On the Bike

by Cat_Fantastic on Sep 13, 2017
Erotic Couplings

The knock on the hotel door sounds so loud in the empty room. Taking one last look in the mirror, I move towards the door, tucking a short strand of hair behind my ear. Hair braided, tank top and bra, jeans, and Harley boots complete my outfit...I hope it meets your approval. A nervous breath and I open the door to see you standing in the hallway, mischief l...

Crime Doesn't Pay

by Virgil_Assad on Sep 14, 2017
Transsexuals & Crossdressers

::A note for the readers. I came upon the idea for this story some time ago. Most forced feminization stories are told from the POV of the subject being forced. I decided to change the format a little and tell a story from the other side. Special thanks to Anelle for help in editing.:: I had originally intended to move straight from one apartment to the...

Stuart's Secretary

by justincbenedict on Sep 17, 2017
BDSM

Stuart thought dreamily of his days at the firm in Chicago, and the two male Masters he'd lived with... One of them deaf. The rich 26 year old Stuart had loved and feared the two men. Now he watched BDSM porn... The way that model has his cock whipped reminds me... Of the day Master Pietro caught me with the Frederick's of Hollywood catalogue that I'd...

A Slow Night in Possum Holler

by oneiria on Sep 16, 2017
BDSM

Professor Walter F. Larsson awoke from his nap with a start. The TV was still on, the silver-haired commentator deploring the most recent depravities in this godforsaken wasteland that his wife of four months called home and in which he had so unwisely chosen to spend his sabbatical.. He heard the sound of motorcycles revving up and then shutting down. His...

Las Chicanas

by AnnabelleRaven on Sep 17, 2017
Non-Erotic

17 year old Alicia Garza lay cradled in the arms of her new boyfriend Tony Torres. Since Alicia and her mom had moved across town before the school year, she quickly became one of the hottest young coeds at the affluent Palm River High School, and she was very interesting in finding a guy that would give her attention, affection, and comfort. Palm River was...

Nature Takes Over

by MistyMorgan on Sep 16, 2017
Exhibitionist & Voyeur

My cuckold boyfriend, James, and I were walking in the woods in the mountains where we were camping. We came upon a couple of hunters who had been in the woods for a couple of weeks. They had been alone all that time and had no pussy for that entire period. They looked at James and said, "Hey there man, you have just want we need, a woman that looks hot an...