Sissy Machine Stories

38,061 results
Orientation
Length
Source
Infinite Scroll

Samantha Finds a Dom Online

by SamanthaSatine on Jun 19, 2018
Transsexuals & Crossdressers

A true story - pre-chastity episode from this sissy slut.. It's Friday... It is 9.30am... Text message received "Are we still on for today" her reply "Yes, I believe we said 10am" Bag packed she takes the short journey across town to the meet. Samantha checks in for the final directions having been once before but it is a secure address with locked a...

Candi is a Sissy Cam Girl Ch. 01

by CandiCumminz on Jan 15, 2019
Transgender & Crossdressers

This is the 6'th story in Candi's tale. Please read the Candi's conversion series and Candi Gets an Upgrade for the full picture of what's happened so far. - Hi! My name is Candi Cumminz and I'm your new favourite bimbo sex-doll. My camera's always on and I'm always horny so stop by any time for a good time! I love dressing up for my fans and putting o...

Recruiting of a Sissy Maid Ch. 04

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Four: Chantel, Fitting Into Her New Lifestyle. Master Holt says, as the two of them walk out from the elevator on the 2nd floor, "This will be the floor that you will begin your life in servitude to us Chantel. Lets go find your head maid Penny and then get you to your room." Chantel grows more and more resigned to this new life as she see's a very...

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...

First Multiple Sissygasm Today

by JessC on Sep 16, 2017
Transsexuals & Crossdressers

I had my very first multiple sissygasm. I own a fucking machine. It has been the source of much pleasure since I bought it. I decided recently to try for a really great sissygasm. For those of you that don't know, a sissygasm is having an orgasm with a soft cock from ass/prostate stimulation. Well, I decided that I was going to prep myself to have a nice la...

Sexy Slut Fantasy Ch. 04

by pdavis616 on Sep 15, 2017
Transsexuals & Crossdressers

The story continues with Sasha and Nicole heading to the sex shop As I sat in the car waiting for Sasha to start driving I pulled the mirror down to take a look at my face. As I glanced in the mirror I saw the strange beautiful woman staring out at me. I licked my lips and gave her a sly smile and I was really surprised to see how good it looked. God I can'...

A Night For Romance

by maggie2002 on Sep 14, 2017
Romance

The night was beautiful as only spring nights can be when winter loosens its harsh hold and the soft winds blown and flowers grow. "Damn, I'm a poet and I didn't know it," laughed Sissy Littleton the Editor of the Littlestown News, as she sat at her computer trying to come up with a short story as filler for the Sunday Magazine. She had to be done by tomor...

Ultimate Sissy Fail

by cdbrittany4bbc on Feb 12, 2019
Transgender & Crossdressers

This is the story of the perfect sissy getaway. This story contains subjects of crossdressing and interracial male sex acts if this offends you please don't read. Everything except one or two events happened, Now, there is some embellishment. I had to tell someone. I decided to tell everyone. A little bit about myself. I am in my late 50s. My adventures in...

Adult Bookstore Whoring

by nancyvasquez on Oct 15, 2017
Transsexuals & Crossdressers

Crossdressing sissy Terilyn Bardot arrived at the adult arcade around 6:10 p.m. The city was having some kind of carnival on the waterfront, and so most of the parking spaces were gone. Teri went in and stripped to just a 2 piece bikini and her high heels. She freshened up her hot red Revlon lipstick and greased up her anus with Vaseline. Then she waited. An...

Sissy Chantel, New Reality Ch. 06

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Six: On My Way to My New Life at The Agency. Well the day has come for my transition in my life to becoming another sissy maid and sissy slut (aka: comfort girl) to 'The Agency'. Over the last two hard and humiliating weeks Master Camron and Sir Gage now as paid agents to my joining the team at 'The Agency' have helped me sell, give away or toss o...