Sissy Roommate Stories

20,331 results
Orientation
Length
Source
Infinite Scroll

The Adventures of Madi Ch. 04

by sexualrelief7191 on Sep 25, 2017
Fetish

"Hi, my name is Madison, or Madi for short. I'm about 5 foot and 3 inches, brunette, cute, and like to have a good time. I'm not exactly like other girls, because I'm bi and have a foot fetish. Yes, a girl can have a foot fetish too. I love feet, and I'm always looking for chance at another girl's beautiful feet." Summer was less than 4 weeks from being ove...

Sammi's Place in College

by Sissy_Sammi_ on Dec 17, 2017
Transsexuals & Crossdressers

Sammi was up at seven AM, as usual, fully dressed and dolled up and tidying up the suite. Something had broken in her brain at this point, she had been re-wired. Her life had taken some drastic turns, and who she was and what drove her had been completely replaced by something new. Sam, in the past, had been at the helm and would occasionally allow Sammi he...

Caught in Her Panties Ch. 03

by Knightofround on Sep 16, 2017
Transsexuals & Crossdressers

As we walk down the street I wink at some of the men walking past us. Alex and Mary giggle as they see the men checking me out. I even smile at the women too. "You are such a tease Krystal!" Alex says noticing some of the women blush as I check them out. We find a nice sidewalk coffee shop and take out seats. As I sit, I feel someone smack my ass. I jump a...

Cindy's Humble Servant Ch. 09

by humbleservantbeijing on Sep 14, 2017
BDSM

About a week later, Peter was at Brian's apartment that Saturday at 9:00 am. He was on his knees in the living room cleaning the grout between the marble tiles with a toothbrush. He could hear Brian in the other room playing a computer game. He heard a key in the front door, and then Cindy entered the apartment. She took off her jacket and hung it on a hook...

Making of a Sissy Whore Ch. 03

by SecretAgentFun on Oct 21, 2019
Loving Wives

Pimped Out If you haven't read the first 2 chapters, it might be a good idea so that this makes more sense. Your call, and I hope you enjoy either way! *** Jeff stepped off the bus feeling defeated as he walked the five blocks back to Brad and Kayla's place. He couldn't even think of it as home now, since Kayla was sure to kick him out tomorrow. He was jo...

Sharing the Wealth

by whoamireally on Jun 1, 2020
Fetish

I am submissive to my wife, Helen, who is an evil genius. She enjoys experimenting with ways to display my submissiveness to other women for her amusement and to humiliate me. She is extraordinary and I love her completely. Over the past year she has instituted periodic "Share the Wealth" evenings during which I am to seduce a strange woman and then submit t...

Sissy Prince: Origin Ch. 03

by SatinSlip on Feb 13, 2018
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** Olivia pulled off his scratchy wool tunic. It had covered him to just below his cute girly ass. It was uncomfortable to wear, made by Orcs. Yet for some reason it turned him on. His tiny sissy bump was now revealed to the world. It was erect, yet not quite two inches long. He...

The Molly Virus Ch. 04

by Sissyhalo on Nov 14, 2017
Transsexuals & Crossdressers

*Jackie... I used to be called Jackson and I had Jeri as my roommate and she or I thought at first was transitioning. I was never much into being a homophobe and stuff so it was just me kinda leaving things alone. Until Jeri and I started fucking. She's really fucking great in bed too and it was pretty hetero too with me the guy fucking this trans black g...

Panty Posers Ch. 03

by EROTICbearscribe on Sep 14, 2020
Transgender & Crossdressers

It was early on Sunday morning. I awoke needing to pee and slipped out of bed, doing my best not to wake Daphne. I could hear him breathing deeply next to me most of the covers on his side as usual. My roomie was lying on his stomach, his head under his pillow. He looked so sexy lying there. I felt the warm rays of the sun on my back as I breathed in his cu...

Briefs No. 03: My Wife's Friends

by PatriciaFCartier on Jul 15, 2019
Transgender & Crossdressers

While sliding my silk stockings up my newly shaved legs, I thought about what got me here. My wife, Madison, told me after I'd been transformed that she'd planned this since before we married. She said she'd dated a boi in college for a while until the boi had been stolen from her by one of their professors. Said she'd liked the concept, if not the result. S...