Bully Roommate Sissy Stories

23,222 results
Orientation
Length
Source
Infinite Scroll

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."...

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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...

Barbara's Binoculars

by CarrieQ on Mar 21, 2018
Transsexuals & Crossdressers

A bit about the house I grew up in. It was one among many rows of identical boxes built after the war; an anonymous place with no obvious character, in an estate on the outskirts of a town in sharp industrial decline. My favourite room was the attic! I'd climb up there and pull the ladder up behind me, guaranteeing I wouldn't be disturbed. Mother liked to...

2035 - The Year of Male Chastity Pt. 07

by Longjohnsilver30 on Sep 17, 2017
Fetish

The day finally arrived that my wife and that bully were due to arrive. There I stood in the hall awaiting their arrival. To save my wife from being anally destroyed by that bully I stood in my new uniform like he demanded in exchange to protect her virginity in that department. I looked so silly. And frilly. I had heard stories of some chastised husbands...

Proud Beta

by Sissyhalo on Mar 13, 2018
Transsexuals & Crossdressers

All parties are over 18 years of age. *** I'm a beta. And yeah for those that get what that is, we're real. I was a white kid that was on the skinny side and I was born and grew up with a little dick. And I was everything that came with being a small dicked little loser then. Bad at sports because that meant dressing rooms back in high school and never...

Heidi’s Submission

by TimT1972 on Sep 19, 2017
Transsexuals & Crossdressers

Eighteen year olds are the same the world over. The handsome, tough and sporty are nearly always the most popular. Adam was none of these, he was rather effeminate, of slight build and definitely no sportsman. As such, he never had that many friends. His home life wasn't much better; his father was dead, he had no siblings and his mother worked every hour Go...

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...

Alexa's Journey Ch. 01

by sj_53 on Dec 17, 2017
Transsexuals & Crossdressers

Authors note: This is an edited version to correct the error of changing from a first person account to a third person account in the middle of the story. All characters in this story are totally fictitious. They are not based on real people. All sexual acts are between adults over 18 years of age. I have no experience with transsexual people and any misrepr...

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...

It's For Charity

by Tomsparty on Sep 12, 2017
Transsexuals & Crossdressers

You gaze dreamily at the little black dress in the charity shop window. It's Christmas, it's party season and you'd do anything to wear the delicate feminine dress. You shrug your shoulders and gaze further into the shop. The company Christmas party is tomorrow and you've no idea what to wear or who to take. You stare once more at the dress in the window and...