Sissy Roommate Stories

20,331 results
Orientation
Length
Source
Infinite Scroll

Bubble Bath

by SexGenie on Sep 12, 2017
Sci-Fi & Fantasy

As she was running into the apartment, she picked up her roommate's newspaper from the front step. She noticed that the headline read: "SCIENTISTS DISCOVER STRANGE BACTERIA-LIKE CREATURE IN WATER SUPPLY; THOUGHT TO BE HARMLESS" Although tired from work, she glanced at the next few lines as she headed into the kitchen to set her stuff down: "Scientists exa...

Tuition Doesn't Pay Itself Ch. 01

by TheLooseCannon on Sep 16, 2017
Toys & Masturbation

I drew my jacket tighter around me, shivering from the cold. I felt the few hundreds in one pocket, and my keys in the other. Whenever a car drove by, I'd grimace and open the jacket to reveal my too tight shirt and too short skirt. I knew I screamed prostitute, but that was kind of the point. Once the car passed, I'd cover myself back up. I shifted my weig...

Hitchhiker Van Gang Bang

by Daisy_Dean on Sep 18, 2017
Group Sex

This story features rough language and even rougher play. Proceed with caution ;) ***** I hate that fucking town. I hate my drunk parents and their constant nagging for me to make more money so that they can continue to collect welfare and fuel their alcohol addiction. I'm only 18 and just graduated high school. I should be looking forward to college, not...

My Roommate Dilemma

by Deptydog90 on Mar 20, 2018
Erotic Couplings

What's a fella to do? I have found myself in a situation that both appeals to me as well as fills me with dread at the same time. I don't know how to resolve it, or even if I want to. Let me explain. I have been married to my wife for almost a decade. I love her very much, but our sex life has diminished quite a bit. When we first met and were married, we...

College SPH

by J902213 on Dec 3, 2017
Fetish

I was never the biggest ladies man in high school but when I got to college I saw an opportunity for a fresh start. To give you guys a picture I'm 5'10 and I weigh about 140 lbs. Just an average dude who's kinda skinny. My roommate was a guy named Alex, super friendly dude. Athletic type, muscular, 6 ft and a good looking black dude. He grew up next to the U...

CFNM College Ch. 04

by Jreforma on Dec 5, 2017
Fetish

On Saturday afternoon, James decided to go for a swim at the school pool. Sarah and Charlotte were off with some of the other freshman girls, but Diane had volunteered to join him. As they walked to the pool, James was already imagining her in a bikini, wondering how her breasts would look in it, whether they would bounce as she walked around. They arrived...

Colleague becomes Roommate

by DeanOfSexEd on Jan 8, 2018
Erotic Couplings

My first attempt, I'd love some feedback, but please be gentle! ;) Disclaimer: None of these stories are real, they are figments of my imagination, based in very small parts on real experiences, but warped in my mind toward how I would have liked them to play out. A dream-sex-diary of sorts, if you will... ***** She was a newly appointed receptionist at...

Granny's Delight

by Wordmate on Jan 15, 2018
Mature

Billy, like any college student before him, spent spring break partying with friends, girls, and ingesting quarts of beer and booze. He was having fun, but somewhere along the way his spring break got a little more exciting. Her name was Carol, a lonely widow who lived by her lonesome; a tank full of tropical were what kept her company. They ran into each ot...

Criminal Affair Pt. 02

by CaffeineFetish on Feb 6, 2018
Novels and Novellas

I do the initial sweep of my zone with my guys, tell them to sweep another zone before I head back to the station. On my desk in my office as promised is the case file which I open and read, primarily the subjects last known whereabouts. Derek is right, there is no reason for us to be sweeping where we are. Monica Lowe, twenty year old college student who...

T-Shirt Weather

by JacquesD on Jul 31, 2018
Exhibitionist & Voyeur

All through high school and most of college, I never felt good about my body. Objectively I knew it was fine—a little flabby at worst—but I could never shake the insecurities of the chubby kid I had been before puberty evened out my baby fat. Junior year, I decided to do something about it. I started copying the exercise and diet regime of my track star room...