Sissy Roommate Stories

20,331 results
Orientation
Length
Source
Infinite Scroll

X-Change

by Noah_Peal on May 15, 2015
Miscellaneous

Pills Pink pills change males to females. Blue pills change females to males. Purple pills (X-Trans) change males or females into transgenders, can be combined with pink or blue. X-Change (Formula subject to change) Acquired from unlicensed "street" vendors. Changed (defective/in testing) formula. Cheapest. High pregnancy risk. Can lead to mental a...

Open in Reader

The Roommate Pt. 07 - Miranda

by ValoryG on Sep 16, 2017
Transsexuals & Crossdressers

The next day, when Josh returned home from teaching college students (who were only around six years younger than him), Miranda met him at the door. She seemed in a fine exuberant mood and gave him a smile. Sometimes he didn't know which personality he'd find - the friendly, mother-like woman who helped him become Lori, or the controlling figure who could...

A new city a new life

by Lonelysub on Nov 13, 2020
Fetish

As you enter a small appartment building, you see a woman with long dirty blonde hair waiting by the elevator. She's wearing a white top and some sweatpants. It's clear to you she's been working out and she has a toned body to prove it. As you are checking out her fine ass the woman suddenly turns around. "Oh hi there, you must be the new arrival."...

Open in Reader

Tinder Pt. 02

by TwistedPanties on Jan 22, 2020
Transgender & Crossdressers

I appreciate you all asking me for more of the story - It would be hotter if you begged ;) Sissies can be so over-eager... (Keep the feedback coming please, Sweeties) Background: Bryan's roommate Caitlin has just discovered his crossdresser girl Tinder profile, while her friend Allison was swiping for a new girlfriend. Bryan is in the kitchen with a baby...

Made a Maid Ch. 01

by JosieCD on Sep 12, 2017
Transsexuals & Crossdressers

(This is my first story. I love feedback! Enjoy!) So there I was, handcuffed, gagged, blindfolded, in full drag, with my panties around my ankles, bent forward, and unable to move. My mind was racing, when is she coming back? What if someone see's me like this? Oh God, what have I gotten myself into? While I stood there, my heart jumping out of my throat, I...

Lesser of Two Evils

by Andi_Lembke on Sep 25, 2017
Transsexuals & Crossdressers

[So to update you all. I'm sorry I haven't completed any more chapters of NWTBYG or Porn Princess. They're in the works, but creation, and good storytelling takes time, something I have less of now. I left my receptionist job to take a writing gig, and all my writing energy is going into that, but my passion for hot stories smolders intensely under the surfa...

My roommate new sissy maid

by Carterdruzba on Dec 29, 2020
Interracial

I been living with Gina who happens to be muscular and stronger than me I haven’t paying my rent for 2 months so one day when I meet her in the living room “you been not paying for months so I have idea for you to repay me so I got this” it was a pair of pink panties heels and black stockings and a maid dress “I decided to should be my maid until you paid me...

Open in Reader

Panty Posers Ch. 02

by EROTICbearscribe on Jul 6, 2020
Transgender & Crossdressers

NOTE: This is a work of fiction. The characters appearing in this series are consenting adults over the age of 18. Any reference to past experiences by any character appearing in this story are intended to define that character. * It was almost 3 when I woke up in my roommate's double bed. Sunlight streamed between the broken slats of his plastic blinds...

My Master

by SissyKaty on Mar 26, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** I pulled into the driveway to my house and I was disappointed to see my future mother-in-law's car in the driveway. "Oh great" I think sarcastically. I'm not looking forward to interacting with her so soon after getting off work. I had just come from a long day working in IT for...

A New Adventure... Ch. 04

by johnjinglez1 on Nov 19, 2018
Transgender & Crossdressers

This is the fourth installment of my "Sex Diary." For the better part of a year and a half I decided to try some new things in the world of CD / TS / Sissy boys. All stories are 100% real. After my last encounter with Mia things really started to cool down on the TS/CD front for me; I'd met a couple of girls who really interested me and were satisfying my s...