Sissy First Stories

313,352 results
Orientation
Length
Source
Infinite Scroll

Neighbourhood Terror to Sissy Pt. 15

by Fibaro on Dec 23, 2019
Transgender & Crossdressers

Chapter 17 "If you don't mind watching over the sissies for a bit, I will go look around for the exact outfit I have in mind. I don't trust Stephanie to get it just right. You will be fine watching over the sissies, right? If not, you can always call out for me, but I am sure you are going to do great." Linda said to Lisa who was still getting her feet wors...

Ultimate Sissy Weekend Ch. 02

by SissyTwinkleToes on Dec 24, 2019
Transgender & Crossdressers

It had taken a good half an hour via taxi to get to this postbox, across the city from Sissy Susie's home. All so Sissy Susie could post five keys to herself, containing the keys that keep her and Sissy Tinkerbell locked in their ridiculous sissy dresses, locked in handcuffs to each other, and locked in the clitty cages that have kept them chaste for the las...

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...

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...

From Husband to Man's Sissy Wife

by Pantypansy on Jul 8, 2019
Transgender & Crossdressers

I was pulling up my white panties and smoothing the tops of my stockings when I heard the doorbell, and my wife welcoming somebody at the door. He had a deep, Scottish voice. Lucy welcomed him into the living room, then closed the door and came into the stairwell and beckoned for me to come down. I felt a chill of fear, but tottered down the stairs in my...

Alt. Queen of the Left-hand Turns

by maxdname on Sep 16, 2017
Romance

See that beautiful girl in the poster? When I first met her she was a simple hillbilly girl from Appalachia sleeping with stock car drivers in order to get a pit pass. Look at her now: she's a blond and a model with her own TV show that earns her more in a year than most stock car drivers will earn in a lifetime on the circuit. A national racing magazine i...

Finding Claire

by Sissyhalo on Nov 26, 2017
Transsexuals & Crossdressers

*Before... I get cleaned up and instead a drink I have a big mug of coffee and a long, long shower. Thinking on all of it a lot. Then I check my bank accounts twice online. I go outside after slipping into sweats and walk around my house and the yard and the garage, the big barn one out back. It's my second house here actually with Roxanne getting the f...

Domina Katarina Goes Shopping

by pbs444 on Sep 17, 2017
BDSM

Several days ago, there was an e-mail in my inbox. It was of course from my Domina, Katarina, because the e-mail account is for her exclusive use, when she wishes to communicate with me. Because I am her sissy slut, and from time to time she finds ways for me to prove my usefulness to her. The e-mail read: "Hello, sissy slut, I have decided I wish to go...

Daddy's Sissy Staircase Ch. 03

by SissyLoniOR on Sep 28, 2020
Transgender & Crossdressers

This is part 3 of a 3-part series, to understand better, go back and read parts 1 and 2. Thanks for everyone's comments, this has been my first story here at Literotica, and I have ideas for many more. Please feel free to contact me with ideas for future submissive sissy slut stories! My visits to Daddy now typically involve more time than just during the...

Turned So Totally

by gbr2004 on Oct 8, 2019
BDSM

It was our first actual meeting. We had emailed back and forth about what we were both looking for and found we had similar interests. He wanted to take a straight acting guy, take his masculinity away and turn him into his submissive sissy bitch. That is what I had been thinking and fantasizing about continually but could I actually do it? From our email ex...