Bully Roommate Sissy Stories

23,222 results
Orientation
Length
Source
Infinite Scroll

Proud To Be A Sissy Ch. 01

by Kary_M on Sep 11, 2017
Transsexuals & Crossdressers

I had just turned eighteen and only had two months of high school left. My marks were good and already had a possible placement in a university where I hoped to get a new start. I was so looking forward to getting away from all the shit that life had forced on me in this little hick town. Usually one of my parents insisted driving me back and forth to schoo...

Sissy Crissi Ch. 03

by sissycrissi on Sep 19, 2017
Transsexuals & Crossdressers

Chapter 3 -- Leroy's Turn But Leroy had been left out for too long. Eager for his turn, I had no sooner finished pleasuring my Mistress when I felt his hands reach up under my skirt and start pawing my panty covered ass. Standing behind me, Leroy bent down and lightly held the back of my thighs in the palms of his large hands. He slowly slid his caress upwa...

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...

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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...

Dog Kennel Ch. 04

by Dylan987 on Sep 19, 2017
Fetish

Background to previous chapters: After answering an advertisement to become a human dog, and then being seen at a 'dog show' by Kevin, the nerdy, ginger haired guy I work with at the local sports store, I was 'sold' to Kevin and now find myself being blackmailed by him, but also strangely enjoying being his 'dog'. ------------------------------- I woke u...

Runt of the Litter

by grimbous on Oct 9, 2017
Transsexual

(This story involves a lot of humiliation of the main character, futa on male action, incest, and other fringe fetishes. If these aren't your thing turn back now. I also wanted to give credit and thanks to the artist Mafen for the above picture which helped inspire this story.) The hall is quiet. You were pretty sure nobody was at home. You creep carefully d...

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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...

The Writer's Secret Ch. 07-08

by AnnMichelle on Sep 16, 2017
Transsexuals & Crossdressers

Synopsis: Loren had no idea what he was getting into when his agent suggested he write transvestite fiction. Nor did he realize how eagerly his wife Stephanie would embrace the idea of feminizing her husband. How far would they go? Chapter 7: Laura Buys Shoes. . . Lots of Shoes Loren rolled out of bed the following morning. He yawned. Despite having sex w...

Black Man One Ch. 21

by Weak_White_Wimp on Sep 19, 2017
Interracial Love

It was apparent from the start that we had not rehearsed what we wanted to say to one another. It was more obvious that Julie didn't want to be there at all. I had not expected to be having this embarrassing opportunity to speak to her at this time. Nor, did Julie expect to be speaking to me. The conversation began rather slowly and tentatively as we "danced...

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...