Caught Sissy Stories

167,051 results
Orientation
Length
Source
Infinite Scroll

Slave History

by timeagain93 on Sep 17, 2017
BDSM

These are my recollections of my slave history. Four Goddesses have dominated me. I'm writing this to let my current Mistress understand my story. Mistress D read "Variations" magazine and spanked me with a wooden spoon. She tied me naked to a chair and blindfolded me. She made me sit there in silence. I was wearing her panties while talking on the phone w...

Madame Jenoix

by Candour on Sep 26, 2017
Transsexuals & Crossdressers

Chapter 1 --------- A young looking and slight 18-year-old boy sits outside the Headmistress's room, obviously feeling anxious. His legs kick back and forth under the chair and he keeps looking up at the door. His uniform looks unkempt, like he has just thrown it on after Games. After some long, countless minutes elapse, he hears a loud, slow "Come!" from...

Samantha Meets a Dom Master

by SamanthaSatine on Sep 16, 2017
Transsexuals & Crossdressers

A true story - I am the main character and all the various activities described were undertaken with my consent...no harm came to me in any way... ***** The date was fixed. The room was booked – neither of the willing parties could accommodate, a not unusual event in the world these two inhabited from time to time. The morning of their meet had now arriv...

Julie's Collaring Ceremony Pt. 02

by julieaugust72 on Dec 25, 2019
BDSM

Welcome to my branding ceremony...Part 2 At this point I have just been branded. When my Master branded me I passed out and shit myself. I woke up with 2 women, Sue and Barbara, cleaning me and explaining the same thing happened to them when they got branded. What follows is the next part of the story. Enjoy and please send me comments. That is how I will l...

Pimped Out Sissy Bitch

by Gemsissy on Jan 12, 2018
Fetish

My phone vibrated softly signaling a text. I almost didn't look at it. I was at a meeting of the board of the corporation I work for, trying to steel my nerves for a presentation I was scheduled to make. This was my first time and instead of running through my presentation in my head I was focused on what I was wearing under my suit. I glanced at the phone....

How I Got My Sissy Name

by allourdesires on Jun 5, 2019
Transgender & Crossdressers

The thing was that He had presented me with the earrings, on my birthday, in front of my wife and innocently enough I had accepted them with embarrassingly gushing sissy enthusiasm, being my first pair that weren't clip-on. The very next day she dragged me along to the local mall, where all of my friends and neighbours shopped, to get my ears pierced at a ce...

Becoming a Sissy Maid & Slut Vol. 13

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Twenty Two: Satin, Ruffles and Lace, Sissy Maids contracted out to Work. Monday morning and I arise as typical at 7:30am, enema, shower, shave do my makeup and put on a maids dress for the day. Today it's back into a black satin one. Master told me though to put on black back seem pantyhose for today which I dutifully do and make sure the seems are...

Sissy Boy Secretary Ch. 04

by Hotenuf4u on Sep 19, 2017
Fetish

Arriving at the office 15 minutes early, walking past three of the other secretaries, noticing them smiling and giggling when they glanced my way. Elaine must have told them of my secret desire to wear panties. Today's choice was the white lace thong pair, which felt good as they rubbed against me as I walked. Feeling my face turning red, I walked faster to...

Becoming a Sissy Maid & Slut Vol. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Title: How I became a Sissy Maid and Slut for a Dominant Master. Preface: I would like to begin by thanking all who will read my story here. This is a sissy story based on many thoughts I have imagined, many times throughout my life. These erotic thoughts have been enjoyed for a long while in my life. Like many sissy girls, stories like the one I will wri...

A Prom Queen Fantasy

by bluesbirds on Jul 15, 2020
Transgender & Crossdressers

"Aww, isn't this little blue number cute?" Tanya squealed from the other side of the rack. I flinched hearing her voice; we had been shopping for almost 3 hours without a break. This was the first time I had gone shopping with Tanya since she found out about my crossdressing fetish. "Come to this side - let me hold it up to you," she demanded. I meekly co...