Permanent Chastity Sissy Stories

27,304 results
Orientation
Length
Source
Infinite Scroll

Fear!

by gentle_man on Sep 14, 2017
Erotic Couplings

He awoke with a start. Had he been having a bad dream? It seemed so real. He dreamed he had been wrapped up tightly in a sheet and carried away. Somewhere. He tried to think. It was all a blur, as if seen through a drug haze. "No matter," he thought, "a warm shower will clear my head." Tensing his muscles, he stretched out his arms, only to find he couldn't...

The Music Teacher

by justincbenedict on Feb 12, 2019
BDSM

Serendipity looked at Trevor, her student, smiling. "You keep making the same mistakes, and I don't think you are truly devoted to the piano." "No, really, I love the piano, and I want to play-" "Trevor, you like the idea of playing the piano." "Really, please, Serendipity. I can pay more-" "And all these excuses, Trevor? One week you told me your metro...

Lust During Quarantine Pt. 02

by ClosetSissy2020 on Apr 13, 2020
Transgender & Crossdressers

Thank you all for the ratings and comments. It seems like you all like the story so far, so as promised, here's part 2. Again, I hope you all enjoy and let me know what you think as I work on editing the next installment! ************** Pt 2. Soft light filtered into the second story room and Nico didn't yet feel like getting out of bed. His head hurt a l...

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...