Permanent Chastity Sissy Stories

27,304 results
Orientation
Length
Source
Infinite Scroll

Becoming Missy

by hottiehunter on Sep 16, 2017
Transsexuals & Crossdressers

It all started back in 1973 in Seattle, Washington. I was 21, living on the south side with a couple of buddies while we were all stationed at area military bases. One Friday night we had a party at our apt. I was standing outside by my car smoking a joint when this guy pulls up in his pick-up. "Hey, how's it hangin?" he asked "Long and loose." I replied tr...

A Slut's Triangle Pt. 05

by Kantarii on Sep 19, 2017
Transsexuals & Crossdressers

It's 3:30 am. By the time I reach the I-85 southbound overpass, I'm an emotional wreck. Tears stream down my cheeks as I speed down the interstate, heading home from Atlanta. All I care about is getting as far away from Kryss as I can. Despite my enduring love for Kryss, those feelings are growing cold. Things really need to change for the better between us...

The Correction of Debbie Donovan Ch. 13

by RoryOmore on Sep 19, 2017
BDSM

Chapter 13: Hung DEBBIE "What are you waiting for girl? Strip!" Mrs Hammersmith demanded. "Can't you see everyone is waiting for you?" The gym at Silvermill wasn't like any gym I'd ever seen before. It was half the size of the one at my school, but instead of being dark and gloomy, it was bright and airy. Late afternoon sunlight came streaming through tal...

Fairy Tale Life Ch. 01

by petitelove on Sep 16, 2017
First Time

Breanna felt like the luckiest ex-secretary in the whole world. Staring at herself in the bathroom mirror, she just couldn't believe so many wonderful things were happening to her. A petite brunette in her early twenties, Breanna was wearing a very expensive white satin nightgown, cut low to show off the cleavage of her luscious high-riding tits. As she whi...

Sodomy in Santorini

by gomorrah on Sep 14, 2017
Fetish

I first met Soula seven years ago whilst on my way to do archaeological fieldwork at Akrotiri on Santorini. I had caught the Blue Star ferry from Piraeus (Athens Port) via the Greek islands to Santorini. The whole trip takes about 17 hours and goes via some beautiful islands - Parros, Naxos, & Ios - but takes so long there is not much to do. As the sun set...

Shooting The Moon Ch. 02

by SEVERUSMAX on Sep 15, 2017
BDSM

Apparently, I fell asleep drunk and tired, which wasn't too surprising, given how much Jameson I drank the night before and how much I had fucked my three playthings. I didn't wake up alone, however. I was in my studio apartment, lying on the sofa, with Dana planting kisses on my cock and balls. Oh, yes, Dana ... the pizza girl, who had been so passionate an...

First Time Out

by Fairy_Nancy on Sep 14, 2017
Transsexuals & Crossdressers

I'm so excited and want to relate this 100% true story quickly while it's still fresh. Please forgive any typos. [My background: Age 48. Closet dressing in earnest for 15 years. Began with slips stockings and nighties but have collected extensive full wardrobe and accessories over time. Boobs, wig, jewellery etc. Slim with shapely legs, dress size UK 14. Se...

Inaugural Crossdress Sexfight Ch. 02

by danidhotcd on Sep 16, 2017
Transsexuals & Crossdressers

CXSFL – Match 2: Dani vs Jamie With my first match under my belt, albeit a humiliating lopsided loss, I felt better prepared and even more excited to try another match. I was hoping to be on the giving end for my next match and felt I had learned some valuable lessons that would increase my chances of getting a win. Although it's difficult to complain about...

Does He Really Want That? Ch. 06

by goamz86 on Sep 18, 2017
Loving Wives

Note from the author: This is a continuation of a story with five previous chapters. This chapter win not make a lot of sense without reading the previous chapters. Furthermore, this is a cuckold, Femdom, sissyboy story. If you don't like thos kind of stories, please move on. Don't read it an leave senseless comments at the end. I love feedback, as...

Halloween Party

by cuck2serveU on Nov 26, 2017
Interracial Love

Trish and Brent hosted the Halloween bash this year. Once again Jennie was still busy with her new vanilla man so she opted to send a replacement for me to service. Once again it would be a surprise because that's how she rolls. As always, this party is the most expensive of the year because it's held at a hotel in Vegas and there is an entry fee for all cou...