Sissy Stockings Stories

45,315 results
Orientation
Length
Source
Infinite Scroll

My Father, The Maid Ch. 02

by SissyOona on Oct 30, 2018
Transgender & Crossdressers

I awoke the next morning fairly early. My sleep had not been as restful as I would have hoped due to the revelations of the previous day. Eventually I pulled myself away from the supreme comfort of the bed and stumbled to the bathroom to take care of my morning business. As I exited the bathroom I could hear the sounds of breakfast being made from the kitche...

The Snow Sissy Ch. 01

by theonewhowas on Sep 16, 2017
Transsexuals & Crossdressers

Somewhere, in the frozen northern regions of our great globe, in the shivering mountains, there is a school of demon. Now, we all know what demons look like – they are creatures of immense, horrifying beauty. Even with their skin (which can range from Jet black, through fiery red, to the purest alabaster white) they possess inhuman and powerfully seductive b...

The Dominatrix Order Pt. 02 Ch. 04

by Jwwsmith on Feb 11, 2019
Transgender & Crossdressers

Protestors swarmed the streets of Femininus on what was the anniversary of the initial passing of the 23rd Law. It had recently been considered for repeal and been upheld by the Council of Goddesses. The protestors demanded that the 23rd Law be repealed and that same sex courtship be legalized. The predominantly liberal crowd congregated before the steps of...

Caught by the Lodger Ch. 02

by SuzieR on Sep 13, 2017
Transsexuals & Crossdressers

Over the next few months Rachel continued my training. She was determined to transform me, in her own words, into 'the perfect sissy slut girlfriend', and I was only too happy to go along with it. There are a strict set of rules that I have to follow. I am allowed to wear my male clothes when I'm out of the house but must also wear a pair of panties undern...

Sara and Steve... Again

by Sexy_SaraCD on Sep 16, 2017
Transsexuals & Crossdressers

Steve. The one man who was there when I first assumed the name Sara. The first man to make love to me. The first man I ever took in my pussy and in my mouth. The first man who treated me like a real woman. Steve. The first man I fell in love with. I often think about him, sometimes everyday and sometimes here and there. When we broke things off, the feel...

Job Interview

by britneyfan on Sep 11, 2017
Transsexuals & Crossdressers

I was interviewing for a new secretary and it had nearly reached the end of the day with no likely successful candidates. There was just one to go, a Tracy Class, whose CV certainly looked impressive and seemed as if she would do pretty well for the job, but I had to wait and see. The company's receptionist, Paula, put her head around the office door to tell...

Domination Ch. 02

by morenowagain on Sep 15, 2017
BDSM

Part I may be found here: http://www.literotica.com/s/domination-15 Chapter Four To be perfectly honest, I was a little overwhelmed by the possibilities. I mean, having another human being ready and willing to do whatever you ask? There are just too many things. Of course, my mind immediately turned toward the more sexual ends toward which I could put Jake...

Developing Emma

by Sputnik57 on Sep 13, 2017
Transsexuals & Crossdressers

Living alone since the age of 18, he could not hide his true feelings to be a girl; was so effeminate. As time went by, dressing up at home was not enough. He longed to go out as a girl; only then would he be free. Despite these longings, a strict conforming to the norm was adhered to, and even though now living independently, a veil was cast over 'Emma'; b...

His Sissy Bitch Ch. 01

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

It started after a transvestite walked into the bar. Sounds like the start of a bad joke but it's not, we were in a party bar after work, me and my boss. My boss and I were having a drink after work; he was more than a little high. An obvious cross dressed man with several friends came in and sat at the bar. 'She' was very cutely dressed, stylish and sexy. M...

A Wife Comes Around Ch. 03

by pinkpanteez247 on Sep 11, 2017
Transsexuals & Crossdressers

Part 3. Sorry it took so long but life gets in the way sometimes. Also had to get the creative juices, along with some other juices, flowing again. I'll try to get into more detail (foreplay), instead of just right into the action. It makes for better reading. * As I sat there and watched, my panties were getting wetter and wetter and I decided to do some...