Sissy Roommate Stories

20,331 results
Orientation
Length
Source
Infinite Scroll

Nymphette

by Brookell on Sep 2, 2017
Erotic Couplings

1985 "They call you what?" "Nympho!" She said proudly. "I'm half afraid to ask why?" "Why the hell do you think?" I laughed at the whole situation. An 18 year old girl telling me her nickname in order to get me to fuck her. It was such a crude way to drop a hint. But as I thought about it, it made a weird sort of sense. I had been working closely with h...

Cougar for College Cock

by ISawYourMommy on Sep 19, 2017
Mature

When she crossed over I-80, Nancy snuggled her lean frame into the soft leather that was wrapped around the driver's seat and kicked off her heels. The countryside and farms blurred beside her and she day-dreamed as the car continued its course, almost on autopilot, down I-57 towards Champaign, Illinois. She enjoyed these drives. They represented the only t...

You've Got Mail

by Slickman on Sep 14, 2017
Erotic Couplings

Note: Just a warning that this story has some gay, lesbian, and minor incest between in-laws. Some wife swapping as well. Didn't miss much. All rights reserved. Enjoy...Slick. * "Do you think they will go for it?" Jim asked his room mate Cliff as they sat by the computer in the small cabin. "I doubt it," Cliff grinned. "Connie will never send us back a...

Chosen of the Fertility God

by shimm2 on Aug 7, 2019
Sci-Fi & Fantasy

Editor's note: this story contains scenes of incest or incest content. ***** At age 21, Eric and I got married. Eric had the rest of our life planned out from there. We were aiming to have our first child around the time of our first anniversary, which would be the summer after graduation. So a month after the wedding, we had an extravagant three month hon...

TFTC

by CopyCat13 on Aug 19, 2017
Exhibitionist & Voyeur

TFTC Michael was a bit weird. He was awkward and overweight and had a dark sense of humor. Despite that he was fairly popular. He was a member of the most popular fraternity on campus and he had dozens of friends and hundreds of good acquaintances. Almost everyone who met Michael seemed to like him. Unfortunately for him that never seemed to equate to a rom...

My Unwanted Transition Ch. 09

by Terrafic on Sep 14, 2020
Transgender & Crossdressers

(Two years transitioned ) With my second anniversary just having passed since I came home, I went out with Andy and Leslie and celebrated. They called it a celebration, but I didn't see what the big deal was. To me, that part of my life was long over now. I got rid of nearly everything from then, and what I didn't trash or donate, I packed away. My house re...

My Private Bathroom

by Bizarre_Consent on Jul 9, 2019
Fetish

Author's note: This is largely a fetish story about people using the bathroom. *** My name is Emily. I'm an anxious, awkward person who has trouble making friends. In my mid-20s, I finally moved out of my parents' place. I ended up in a cheap, roach-infested apartment on the outskirts of New Rochelle. Two other girls were already living there. I paid m...

Lost Love Pt. 01: The Reunion

by StarsAligned on Mar 2, 2020
Erotic Couplings

Part I - Reunion Alyssa stared quietly into the mirror. She took in how her naturally auburn hair was braided to create the effect of a crown on her head before cascading down her back. The make up was delicate, he had called in a favor from a friend who was a makeup designer who had done a fantastic job, accentuating her creamy white skin. Alyssa loved how...

New Family Rules Ch. 06

by HStoner on Nov 18, 2019
Exhibitionist & Voyeur

This story is the sixth in a series. I recommend reading the prior "New Family Rules" stories in order because this story is a continuation of those. I hope that you find my characters as interesting as I do. Any similarities to any real person or entity are entirely coincidental. Whether you like the story or loathe it, comments are welcome. All characters...

Katie's World is Rocked by a Coat

by LuckyDave1066 on Dec 2, 2019
Exhibitionist & Voyeur

BZZZZZT "UPS!" came blaring over the entrance intercom speaker in Katie's apartment. She knew from previous experience that the driver wouldn't wait more than a few seconds before heading back to his truck, and since this was the third attempt to deliver her shiny new Mac Book Pro she'd need to make a highly inconvenient trek to the UPS distribution center i...