Chained Sissies Stories

7,675 results
Orientation
Length
Source
Infinite Scroll

Becoming a Sissy Maid & Slut Vol. 14

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Twenty Three: Sissies at Work, Sissies as Sluts at the Farm. 4:00am and the alarm clock goes off. We three sissies must wake and begin our day of long, hard labour of degrading sissy maid and sissy slut work. Off comes our sleeping lingerie and soon three naked with only our chastity devices dangling on our sissy dicks we must quickly and together s...

Sissy Chantel, New Reality Ch. 05

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Five: Oh, Oh, My Surprise. "Ohh, Ahhh...Wha...what." I say as I wake up and am lost with where I am and what is going on. "What the... What the Hell? Where am I and what is this? Huh, what the Hell? Why am I chained and padlocked around my waist?" I'm groggy and very confused as I look at the room, dimly lit with a single hanging light bulb, I'm on...

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...

Like a Dream

by Scotsdude on Oct 15, 2017
Fetish

As I arrived at work that Monday, I knew that it would not be a normal day. My throbbing head was a distinct reminder of how my weekend had been. Saturday night was a blinder. It was my friend Kevin's 30th birthday, and as such, we decided to make it a bit of a blinder. It started out with paintball, went on to karting, dinner, and a strip club. Prague's st...

Becoming a Sissy Maid & Slut Vol. 12

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Bonus chapter added to keep this story moving forward. I felt it should be told and enjoyed. ***** Chapter Twenty One: Sluts at a Party. Our Masters always looking at ways to get the word out about us three sissy sluts all to make sure we become looked for and hunted street walking sluts for sex starved and horny males leads them to putting us out in very...

A Sissy Fantasy

by Sissy_Jeanette on Mar 30, 2020
Transgender & Crossdressers

My darkest fantasy has come true. I'm now a slave to a dominant couple. My ex-wife and her new boyfriend have taken me in, and in return I am dressed as a girl always and their maid and sex slave. Frilly panties, stockings and skirts, babydoll t-shirts, and a blonde wig are parts of my new uniform. Also I now wear a stainless steel chastity cage now encasing...

A Sissy Maid's Tale Ch. 01

by Erotictales4u on Sep 19, 2017
Transsexuals & Crossdressers

All characters in this story are over 21 years old. This is a fictional fantasy in the femdom niche, it is focused on male submissive humiliation and has a Sissy theme running through it. Is set in an imaginary future. ***** The cool air licking at my almost bare ass cheeks enhanced the feeling of nakedness, but I wasn't naked. In fact, it would have been...

How To Be A Boi Bitch Lesson 03

by gothicboibitch on Sep 13, 2017
Fetish

Did you enjoy our first fuck together, my darling bois? I know I did. I'm still thinking about it. Are you? Of course you are. And with that excitement, still, such shame. Making your cheeks burn. Making it difficult to look into your wife's eyes. To meet your girlfriend's gaze. You are no longer afraid. You are ashamed. Of what you are becoming. Of her fi...

A Week End with Mistress Pt. 03

by gasissynora on Nov 6, 2018
Transgender & Crossdressers

Dear readers this is part 3 of my first story and I hope you enjoy it. Your comments and suggests will be most helpful. I am planning on continuing the story if the feedback is positive. ***** Once we are on the way I feel a wonderful vibration in my ass. I then realize that the device Mistress inserted in my ass is remotely controlled. I sit back and enjo...

A Week End with Mistress Pt. 04

by gasissynora on Oct 8, 2019
Transgender & Crossdressers

This is a continuation from part 3 of this series. To understand what is happening you should read the previous parts of the story. I hope you enjoy this and would welcome your comments. * Mistress Nikki grabs our hands and leads us to a room behind the stage. There are some lockers in the room, a bed, some bondage equipment and other kinky paraphernalia....